Episode 31 of AI & I: Every's first entrepreneur in residence Brandon Gell (former cofounder/CEO of Clyde, sold to Cover Genius) turns host to interview Dan Shipper about how Every is building an AI media and software company. Topics include Dan's early coding and first startup, lessons from running a B2B insurtech business, what brought Brandon to Every, Every's master plan, live demos of the AI apps Spiral and Sparkle, and advice for AI startups on shipping fast and finding valuable niches. # Channel Presentation Observations — Ep. 31 with Brandon Gell ## Observable Presentation Format - **Interview/podcast format with a recurring host**: Dan Shipper interviews guest Brandon Gell; the guest addresses the host by name and references prior episodes' patterns ("in this show we tend to look at how people work with AI"). - **Structure announced in-episode**: the host explicitly frames it as "a little bit of a non-traditional AI and I interview because we're going to do some AI use cases but it'll be specifically around some of the products we've been building." - **Live product demonstration segment**: the episode includes an on-screen demo of internal tools (Spiral converting a podcast transcript into a tweet; Sparkle organizing the desktop), with the host narrating usage. ## Intended Audience - **Entrepreneurs, founders, and technical builders**: direct call to action — "if you're a technical founder or you're a technical person that wants to build stuff you should reach out to Brandon… we're looking for more entrepreneurs in residence." - **People interested in AI workflows and tools**: framing of the show around "how people work with AI" and a closing pitch about "knowledge bombs about ChatGPT." - **Readers/subscribers of the host's media company**: the guest notes "I've been an Every subscriber for a long time," and the host references "if you're an Every subscriber" — indicating the show overlaps with a publication audience. ## Claimed Scope / Self-Description - **Channel positioned as AI-focused**: the outro (apparently a scripted/joke segment) calls the show "AI and I" with "Dan Shipper as the captain of the spaceship," framing it as a show about ChatGPT and AI. - **Host self-describes as a writer and media-company founder**: "at the core like I'm a writer," and founder of Every, originally "Super Organizers," a newsletter that evolved into a bundled media business. - **Organization scope claimed by both speakers**: Every is described as spanning writing, a podcast, courses, a $20/month subscription, software products (Spiral, Sparkle, Lex), and consulting — summarized via the "pyramid" business model explanation. - **Guest's claimed role**: "Every's very first entrepreneur in residence," formerly founder of Clyde ("Insurance technology company… raised like 50 million… you sold it"). ## Demonstrated Patterns (vs. Claims) - The episode demonstrates a **long-form, conversational, personal-history interview style** (origin stories of both host and guest) rather than a pure tool-review show, despite the AI-focused framing. - Demonstrated **internal tool showcase**: hosts demo their own products rather than only third-party AI tools, which the host notes is novel for the show — "one of the things I just have never talked about on this show is like the tools that we build." - The episode ends with an explicit **engagement ask** ("smash that like button and subscribe"), confirming a subscription-driven channel presentation. ## Evidence Notes - No curated metadata was supplied; all observations derive from the title and transcript. - The closing hyperbolic outro appears comedic in tone; treated as observable presentation rather than a literal claim. # Delivery Observation Document **Video:** How We Built a Media and Software Empire With AI - Ep. 31 with Brandon Gell ## Speakers & Format Two-speaker conversational interview: **Dan Shipper** (host) and **Brandon Gell** (guest), with a notable structural choice — Dan announces they will "turn the tables a little bit and have you actually ask me a few questions," so the episode opens with the guest interviewing the host before reverting to the standard format. --- ## Tone & Register - **Casual, affectionate, and mutually flattering.** Both speakers repeatedly compliment each other: - Brandon: "I feel like nobody actually really knows who Dan shipper is that you're like this technical Prodigy" - Dan: "you've just like totally like just raised the level of our execution and our Pace like dramatically" - **Self-deprecating deflection of praise.** Dan accepts the flattery, then downgrades it: "I love being gassed up like that... I think technical Prodigy is maybe like stretching it a little bit." - **Emotional openness.** Both share vulnerable anecdotes (panic attacks, crying during toasts), delivered in the same casual register as the business discussion. --- ## Vocabulary & Filler Patterns - **Heavy use of "like" as a discourse marker** throughout both speakers — this is the most pervasive verbal habit in the transcript. - **"Um" and repeated word restarts** are frequent: "so um so anyway uh I did a I just did a bunch of projects." - **Recurring intensifiers:** "really really," "very very," "super super" — e.g., "it just went super super super super viral," "they were very very serious." - **Startup/media jargon:** "product Market fit," "bootstrapping," "bundle economics," "TAM" (as "the Tam"), "dog fooding," "tip of the spear," "co-browsing," "SaaS." --- ## Teaching / Explanatory Habits - **Analogies to explain business concepts:** - Co-browsing explained via contrast: "sort of like screen sharing but instead of sharing a... desktop you share what's on a web page." - Excel analogy for AI products: "I think chat gbt and Claud are the same basically... for a new generation of computer users." - Bundle economics framed through Ben Thompson: "Ben Thompson probably makes like three million a year." - **Definition-by-example.** Clyde is pitched via Apple: "if you think about Apple Care... their customers really appreciate it." - **Numbered/enumerated reasoning.** Brandon lists failure modes: "namely competition... time to Value... and then last one is spending money." --- ## Narrative Techniques - **Origin-story storytelling with concrete childhood artifacts:** Dan's "megsoft" notebook ("step one write soft... step two... burn it to CDs"), Brandon's solar decathlon and school-bus renovation stories. - **Direct address to third parties.** Both speakers address absent people: "John if you're listening... come back into my life." - **Vivid sensory recall of key moments:** the frosted-glass law office, the Evernote note reading "be aggressive like let them know that we have other options." - **Metaphor for emotional states:** Brandon's "I can't hear the music anymore"; Dan's dryer image: "someone put you in a in a dryer on like the... perm press cycle." --- ## Interaction Patterns - **Active reinforcement and interruption-free mirroring.** Each speaker frequently affirm-then-extends: "exactly exactly," "totally," "yeah I think you're spoton," "I love that." - **Relatability-matching.** When one shares a hard experience, the other responds with a parallel one (both share post-sale emotional collapse stories). - **Live artifact walkthrough.** Dan reads Brandon's actual email aloud on air ("all right I've got the email"), and Brandon demos Spiral and Sparkle on-screen — a show-and-tell habit. - **Closing calls-to-action:** "if you're a technical founder... you should reach out to brandon" and a final automated-sounding outro: "smash that like button and subscribe." --- ## Stable Patterns vs. Isolated Moments - **Stable:** casual register, "like"/"um" density, mutual praise, analogy-driven explanation, enumerated lists. - **Isolated / low-confidence:** the outro segment ("I'm absolutely hopelessly in love with you") is stylistically unlike everything before it and appears to be a scripted or generated sign-off — no repetition elsewhere supports treating it as a speaker habit. Similarly, the sexual innuendo joke in the outro has no parallel in the conversation proper. # Position Extraction: "How We Built a Media and Software Empire With AI – Ep. 31 with Brandon Gell" ## Speakers - **Dan Shipper** — co-founder of Every, host of the "AI & I" podcast, previously founded Firefly - **Brandon Gell** — entrepreneur-in-residence at Every, previously founder/CEO of Clyde --- ## Dan Shipper: Background & Positions ### Early interest in technology - Read a **Bill Gates biography in middle school**; wanted to start a Microsoft competitor called **"Megasoft"** with a plan that consisted of: "write soft," burn CDs, distribute to mailboxes, "wait." - Called the "technical prodigy" framing **"maybe stretching it a little bit"** — explicitly downgraded the compliment. - Learned to code (BASIC from a book his dad bought) to build businesses where "the only cost was my time." ### First software business - Built **"Find It"** for BlackBerry pre-iPhone: an app that made a silenced phone ring when emailed a special subject line. Iterated into web interface with tracking, locking, backup, call-you features. - Sold as **one-time purchase (~$10–20)** rather than SaaS because Stripe didn't exist: "I would have had a lot more money if stripe had existed when I was in high school." ### Problem identification as a skill - Described recognizing problems as **"a muscle"**, possibly linked (half-jokingly) to "my Jewish neuroticism." - Framed problem-seeing positively: seeing problems means "we're empowered to fix them." - Noted school doesn't teach defining "the box" — his side projects as a kid forced him to. ### Firefly (college company) - Origin: his father (cemetery/funeral home entrepreneur) wanted a shared grid overlay for discussing diagrams on phone calls. Shipper's initial reaction: "Dad that's dumb." (Brandon: "that's how most great ideas start.") - Co-founders built first version at a Penn hackathon; a company asked to use it for **customer service**, choosing that direction over email signature marketing. - Technology: **co-browsing** — JavaScript-based, cross-platform (back to IE8), letting agents see customers' web pages in real time. - Bootstrapped with only $20K from Dorm Room Fund (First Round Capital) — "first investment of dorm room fund." - **Acquisition at 22–23**: A live chat company began diligence; Shipper recounts their head of bizdev had an intimidating Israeli executive whose Evernote was accidentally visible with aggressive negotiating notes ("be aggressive... tell them that they suck"). Shipper's retrospective: "that's pretty [__] up." - Pega reached out to partner; Shipper hinted at the pending sale ("we may not be around to partner with, wink wink"), creating an auction dynamic. Tripled the price to the first company, which declined; sold to **Pega** ("they were so nice... kept all their promises"). - Flew from college graduation to Boston to finish negotiating. ### Philosophy & entrepreneurship - Majored in philosophy; saw overlap with the **Lean Startup**: if startups are "science," then philosophy of science should be taken seriously as a metaphor. - Self-described love of "extremely boring... philosophy books" as "my happy place." ### Emotional toll of selling companies - Had his **first panic attack after** the Firefly sale was done, not during: "I was holding my [__] together and then I started having panic attacks after." - Selling left an identity vacuum: "you should feel great... and there's not really a playbook for it." ### Founding Every (originally Super Organizers) - After leaving Pega (2016), spent "almost four years wandering the desert": wrote a novel, angel invested, worked at incubator Prehype. - Original strategy: a newsletter as a **pretext for interviewing interesting people** about their productivity/note-taking systems, then build a "tools for thought" business and sell it to the audience. "I just got stuck on building the newsletter... it turned out I just really liked it." - Co-founded with Nathan (Substack's first employee) as a **writer collective** in the Substack/creator-economy wave: bundling business newsletters under one subscription, with a revenue-sharing system, Discord, shared editing. - Diagnosis of the collective's failure: - Few writers can "make it on the internet"; business writers even rarer (must know the domain, write well, write weekly, want to) — and people who know business "can make way more money... as an executive." - **Media differs from software**: changing the writer loses product-market fit, so the "founder builds v1 then hires" playbook doesn't transfer. - **Bundle economics** were "a mess... everyone's unhappy." - Pivot: consolidate to **one newsletter**; Shipper decided to become the main writer rather than do "the typical CEO thing." ### Nathan's Lex - Co-founder Nathan built **Lex** (AI word processor at the GPT-3 moment); it went viral and was **spun out** as his own business (still in the Every bundle). Shipper called it a reinvention moment: "what do I want this to be... I think at the core I'm a writer." ### On doing what you're good at - Admitted fighting a tendency "to pick up other people's expectations and then try to fulfill them regardless of what I want... I still fail at it often." --- ## Brandon Gell: Background & Positions ### Architecture & making - Studied architecture at **Middlebury** (wanted to be an industrial designer; called the program "kind of a janky version of architecture"). - Key lesson: **iteration** — moving from write-once-and-submit habits to comfort with "throwing a bunch of stuff at the wall." Teacher banned rendering; a quarter of sketching only. He "sucked at drawing." - Framing on boxes: architecture taught solving problems *inside* a box, never *defining* the box — "you're just looking at the whole world and it's infinite possibilities." ### Solar Decathlon - Chose Middlebury largely for the DOE competition: build a fully solar house, ship it to Irvine, CA, build in 7 days. Taught himself **AutoCAD** as a freshman; designed panel schematics constrained by a **7-foot width limit** (to travel by train efficiently). ### Early ventures - Renovated a school bus into a mobile entrepreneurship school with a friend. - Built **Photon**, a photo-printing app, with friends (no market research; Shutterfly existed). "My aunt printed a ton of photos." Both speakers defended low-deliberation early shipping as learning. ### VFA & Knockout Concepts - VFA fellow (noted VFA "RIP just shut down"; played basketball with Andrew Yang, "a really really good basketball player"). - Worked at Columbus startup Knockout Concepts (3D scanner, 4-person team); partly chose it for "a really cool office... ping pong table." - Problem discovery arc: launching on Shopify + Affirm + Stripe, wanted embedded **insurance** for the $3,000 device; found insurance companies had "zero technology... they don't even know what API docs are." Took ~6 months to recognize this as a startup opportunity. ### Clyde (insurance tech) - **Pitch**: enabled any business to launch its own **extended warranty program** (AppleCare analogy); marketplace of insurers matched to products; launch "could take 30 seconds" on Shopify. - Privilege acknowledgment: "super privileged... backing of my parents and I live with my grandma for a year" while making $18K/year. - Turned down **exclusive** insurance deals early; later called it a competitive edge, while conceding his then-stance ("[__] these insurance companies... they should be making as little as possible") "doesn't really make sense." - **Cautionary-tale diagnosis** of Clyde's problems: - Raised $3M (22 y/o, ~12 people), then $14M, then a Series B — "we had money to spend and therefore we spent it and we were encouraged to spend it." - Believed they had PMF before understanding **competition**, **time-to-value**, and the dangers of spending. - Implementation friction: business teams sign deals, technical teams don't know about them; retailers' legacy ERPs are a mess. - Focus lesson: "if we had just decided to be the best version of this company only for Shopify we would have been more successful." Shipper agreed re: boiling the ocean; Brandon: "very hard lesson... about focus." - Pandemic stimulus ($2,000 checks) made the business "totally skyrocket" even amid the downturn. - **Sold to Cover Genius** (Australian competitor entering the US) on March 14th, "a couple weeks after SVB shut down." - Post-sale emotional collapse: couldn't give a toast at a surprise dinner without crying twice; a week later got "extremely sick"; describes wife Lydia stopping mid-walk to tell him "this is called anxiety" — "eye-opening." (Shipper noted Brandon's wife is a therapist.) - Identity framing: "I can't hear the music anymore... the first thing I'm going to do is go try to hear the music again. Now I can hear the music." - Dating anecdotes: 7 a.m. coffee dates; invited dates to the Spa 88 bathhouse — "only one person was down and it was a really good date." --- ## The Shipper–Gell Relationship - Met when Brandon pitched Clyde at Prehype; Shipper was angel-investing, missed the deal ("the one that got away"), remembered Brandon as **ambitious + intellectually rigorous + straightforward** ("what you see is what you get"). - Brandon's re-entry email (read on air), sent from Nicaragua: after the studio with his Middlebury friend fell through due to the friend's life shift, he proposed three pillars for Every: 1. **Consulting** (AI training, helping companies choose/implement AI) 2. **Product studio** (profit-driven, small internet products) 3. **Investing** ("we could get into any deal... every just has clout") - Shipper's response: "very interested in incubating new products at every." - Funding model: consulting revenues fund the studio — Brandon called starting two businesses at once "a risky thing," but "it's going plan which rarely happens." - Brandon on Every's appeal: distribution (he struggled to get users alone, "got banned from Reddit like 10 times"), sparked by Evan's napkin-math column concluding the **billion-dollar solopreneur is "not possible"** — Brandon's inversion: enable it with the right tools. - Brandon also cites Shipper's earlier piece **"Be Sincere, Not Serious"** as changing his mentality during Clyde. --- ## Every's "Master Plan" / Pyramid Model (Shipper) - Base: **free content** (articles, podcast) — "hundreds of thousands or millions of people." - Next: **$20/month subscription** bundling writing, behind-the-scenes podcast content, course discounts, and software (Spiral, Sparkle, Lex). - Above: **training/consulting/courses** — fewer people, higher price. - Top: **speaking/advising** — fewest, most expensive. Cash from the top funds more writing/products. - Explicitly counter to Silicon Valley single-business-model advice; the asset is "the audience and their relationship with you," and different audience segments warrant different products. - **NYT comparison** (Brandon): NYT "went backwards into" this model; their quality level is a benchmark. Brandon added quality as a hard-to-maintain priority: "we're not going to put it out if it's like some [__]." - Shipper's caution: "things almost never work this easily so I'm almost suspicious," and risk that pyramid levels "have different incentives." - Shipper's constraints: little raised capital, no external pressure, no rapid hiring; priority is keeping the "creative playground" and quality. - **Distribution thesis** (Brandon): "when intelligence costs zero dollars... it's distribution that's important"; Every built audience before this became a concept. - Call to action: recruiting more entrepreneurs-in-residence / technical builders. --- ## AI Product Positions ### Spiral - Demoed: converts raw podcast transcripts into tweets via a super-prompt + examples sent to **Claude**; ~4,000 users; Shipper uses it weekly (tested on Kevin Roose episode). - Shipper's economics: manual tweet-writing takes ~an hour vs. "like five seconds." - Origin: Shipper built first version during a **think week** (quarterly Every practice, itself Bill Gates-inspired) in a two-day "fugue state" coding with Claude. - Shipper's **Excel analogy** (crediting **Tom Tunguz**): Excel was the general-purpose killer app that trained business users and was progressively unbundled into SaaS over 20 years; ChatGPT/Claude are the same for a new generation — general tools training users who will then want purpose-specific tools. - **Disagreement (preserved)**: Brandon hypothesized Spiral-type tools *unlock AI for non-users*, since a chat box is "the definition of not in a box." Shipper partially agreed but argued **early adopters are people already using Claude who know it's possible but hard**; non-users "don't know it's even possible," and arrive later via colleagues — possibly skipping the raw-LLM stage or using the product as a gateway to Claude. ### Sparkle - AI file organizer for desktop/downloads/documents; launched day before recording. - Brandon's observation: Sparkle launched **smaller than Spiral**, contrary to expectations — because "you're allowing AI to organize your computer... that's scary," even though it can't delete files and is easy to undo. "Mentally like that's very real." - Features shown: **Recents** (3-day hold), **Manual Library** (untouched folders; user-organized), **AI Library**. - Shipper built a manual version ~4 years ago on Tiago Forte's **PARA** system; noted Forte "at least tweeted" about Sparkle — with an explicit qualification: "I'm not sure whether he uses it... he at least [tweeted]." (Brandon on the confidence vote: "we say that that's true.") - Brandon's product philosophy: seeking products delivering value "you don't actually need to engage with... you don't have to think about it ever again but you feel it every day." --- ## Cross-Cutting Themes (both speakers) - **Builder traits**: both endorsed self-teaching ("I'll figure it out"), curiosity, being energized rather than intimidated by problems, and sometimes acting on little deliberation early on. - **Anti-playbook stance**: designing the company around what founders are actually good at (Brandon cites Brian Chesky's talk on designing your company); "if we're not having fun then what's the point" / "build calm businesses." - Both shared **stress/panic** experiences tied to founder life and company exits, with no playbook for post-exit identity loss. ## Anomalies - The transcript ends with a **promotional outro** addressing Dan Shipper romantically ("I'm absolutely hopelessly in love with you") — no speaker is identified for it in the transcript; it appears to be a closing segment voice, attribution uncertain. # Speaker Attribution & Provenance Record ## Video Identification - **Title:** How We Built a Media and Software Empire With AI - Ep. 31 with Brandon Gell - **Video ID:** `01a0f15b-08fa-75ba-aa3e-68638db90c8a` - **Transcript only; no curated metadata supplied.** ## Identified Speakers & Roles ### Dan Shipper - **Role:** Host / creator of the podcast ("AI and I"); co-founder of Every; the episode's primary interviewer. - Explicit evidence: "Brandon welcome to the show" addressed to him; he says "we do something at every called think week"; he introduces himself as the founder of Firefly and Every. ### Brandon Gell - **Role:** Guest; described in transcript as Every's "first entrepreneur in residence"; founder of Clyde (insurance tech company), ex-VFA fellow. - Explicit evidence: "you are every's very first entrepreneur and residence"; "you started a insurance technology company called Clyde." ### Closing narrator/promotional voice (unidentified) - **Role:** Promotional outro announcer; speaker not identified by name in transcript. - ⚠️ **Promotional segment flagged:** The closing paragraph ("smash that like button and subscribe... Dan I'm absolutely hopelessly in love with you") is an explicit subscription-promotion segment. ## Referenced Third Parties & Sources (as mentioned by speakers) ### People - **Bill Gates** — subject of biography Dan read; inspiration (per Dan). - **John Collison** — Stripe co-founder; per Dan, spoke at Penn, offered him a Stripe job. - **Nathan Baschez** — Every co-founder, first Substack employee, built Lex (per Dan). - **Evan** — Every writer, "Napkin Math" column (per Dan). - **Ben Thompson** — cited revenue estimate ("probably makes like three million a year") — third-party claim by Dan. - **Andrew Yang** — played basketball with Brandon during VFA (per Brandon). - **Kevin Roose** — NYT columnist, prior podcast guest whose transcript is demoed in Spiral (per Dan). - **Brian Chesky** — referenced talk on "designing your company" (per Brandon). - **Tom Tunguz** — cited as source of the Excel-unbundling thesis (per Dan: "I'm taking this from this guy Tom Tunguz"). - **Tiago Forte** — PARA system; Brandon claims he "at least tweeted" using Sparkle (**uncertainty explicitly noted in transcript**: "I'm not sure whether he uses it"). ### Companies & Products Referenced Every, Clyde (sold to **Cover Genius**, March 14), Firefly (sold to **Pega**), Stripe, Substack, Lex, Spiral, Sparkle, Knockout Concepts, Prehype, Dorm Room Fund / First Round Capital, VFA (noted as shut down), The New York Times, Shutterfly, Shopify, Affirm, Middlebury College / Solar Decathlon. ### Publications/Works Referenced - *The Lean Startup* methodology; Bill Gates biography (untitled); "Be Sincere, Not Serious" (Every article); "The Billion Dollar Solopreneur" (Napkin Math column); "Every Master Plan" article; Dan's article about Excel. ## Provenance Notes & Uncertainty - **No timestamps** present in transcript. - **Third-party claims unverified:** Ben Thompson revenue figure; Kevin Roose description; Tiago Forte Sparkle usage (explicitly hedged). - **Quote read aloud on-air:** Brandon's email to Dan ("long time no talk considering my next move...") — read by both speakers during the episode. - **Comment availability:** Not stated in transcript or metadata; **unknown**. honestly before even getting into like where every started I feel like nobody actually really knows who Dan shipper is that you're like this technical Prodigy and like are actually high like I don't even know if people know that you're really Technical and like build stuff let alone sold a company at like whatever 14 well I can also go back and first of all that's very very generous of you I love being gassed up like that I'm going to have to gas you up a little bit later but I think technical Prodigy is maybe like stretching it a little bit why don't I go back I think like usually where I start on this kind of line of questioning is like when I started getting into Tech stuff in general which is when I was uh in middle school I read a Bill Gates biography and I was enamored I was like I want to be Bill Gates I wanted to start a Microsoft competitor and I was going to name it megasoft Brandon welcome to the show thanks Dan thanks for having me so for people who don't know you are every's very first entrepreneur and residence uh you're also a uh really talented entrepreneur uh you started a uh Insurance tech technology company called Clyde about I think like seven or eight years ago you raised like 50 million bucks you had 100 employees you sold it um when I think in like March right yeah March 14th you sold it you sold it in March um and then you joined every and it's been a it's been a kind of amazing amazing ride since you've joined I feel like we've really really accelerated everything we're doing so I'm just psyched to um psyched to have you on psyched to to talk about uh what you're doing with us talk about every generally talk about our relationship because there's just a there's a lot of cool stuff going on yeah we surprisingly go pretty far back actually um but yeah this has been kind of a dream come true for me honestly I've I've watched uh you go from Super organizers to whatever he is today and um just having this creative playground has been an amazing opportunity I love it I love it so I think um the way we'll structure this is a little bit of a non-traditional Ai and I interview because we're going to we'll do some AI use cases but it'll be specifically around some of the products we've been building together um inside of every um but to to get things kicked off um I thought we would sort of turn the tables a little bit and have you actually ask me a few questions so that I can kind of like lay out every what it is like what the background how we got to where we are today and then I'll turn the tables back to you and um you'll talk about some of the some of the product work we've we've been doing and demo some of the things we built yeah honestly before even getting into like the uh uh where every started I feel like nobody actually really knows who Dan shipper is and the fact that you're like this technical Prodigy and like are actually high like I don't even know if people know that you're really Technical and like build stuff let alone sold a company at like whatever 14 um so I feel like you should just give me the I don't even know the full story but like I know you started a company in college so maybe we start there well I can also go back and first of all that's that's very very generous of you uh I I love I love being gassed up like that I'm going to have to gas you up a little bit later um but uh I think technical Prodigy is maybe like stretching it a little bit um but I why don't I go back I think like usually where I start um on this kind of uh this kind of line of questioning is like when I started getting into Tech stuff in general which is um when I was a uh a in middle school I read a Bill Gates biography um and I was uh I was enamored I was like I want to be Bill Gates I wanted to start a Microsoft competitor and I was going to name it megasoft and um great name I know and I actually still have still have the notebooks from that from that time period um and I had like a whole uh like plan for how I was going to start this company and the plan was step one write soft I didn't even finish software just write soft um step two WR WR soft like this was just you wrote that in the notebook and it was just right soft yeah right soft because I was going to build a Windows uh an alternative to Windows that was my my goal so I got it sure easy yeah I was doing the like the plan so so write soft and then um burn it to CDs um uh because it was I don't know if you remember like do you remember the days like when AOL like in every grocery store you could get like a little AOL disc and then you would like install it yeah so I wanted to do that and then I was gonna and then I the third step was distribute to mailboxes um and then which you know makes sense you're following a set game plan here that's been success was really successful until it wasn't yeah um distribut mailboxes and then um and then the last step was wait um and that was my whole my whole strategy yeah um nice yeah but that's that's basically why I learned to code because I was like I wanted to like build this Microsoft competitor um and I like made my dad go out and buy me a book on basic the programming language and um I was sort of Off to the Races from there I quickly like realized that um I was not going to build a Microsoft competitor but I kept doing it because I was always interested in building businesses and being technical at that point like um it was the only way that I could build a business where the only cost was my time um so as a middle schooler like empowered me to like build businesses where I could actually make money and that was like I was I thought that was the coolest thing ever yeah I mean I think that's amazing as a middle schooler that you were so obsessed with this I was certainly not I don't even think I knew what coding was um I don't even know what I was doing I was like what were you doing I was tossing a frisbee somewhere like I was like very sporty you know kid yeah see I was like I was not athletic at all which maybe like you know helped helped me get into being technical because otherwise I would have been outside with friends yeah yeah I I don't know about friends but I was playing sports um and also it should be I think it's important for everybody to know that you are act I mean I don't know if you're actually still obsessed with Bill Gates but we do do something at at every called think week once a quarter and I know that that's I mean I actually didn't know when I started here that that is what Bill Gates used to call his like when you would run away to a cabin yeah um so you know there's still there's still that through line still still inspiring stuff here still still Gates inspired uh have not have not unseated Windows yet but there's still time totally yeah our next our next incubation yeah I think the next like um kind of stop on the trajectory is um I I was programming for a while I built a bunch of little dinky stuff that like didn't really matter and then when I was like in late middle school early High School I started noticing that um smartphones were becoming a thing so like Nokia smartphones and blackberries and that um you could actually start to build software for those phones like thirdparty apps and I remembered from my Bill Gates days that new hardware platforms are often really good opportunities to build interesting software businesses um and so I got really obsessed with like building software for phones um and this is before the iPhone came out um so app there was no word app it was just like Blackberry software um and so the first piece of software that I built was uh called find it and uh basically I kept losing my Blackberry in my house and it would be on silent and I couldn't make it ring so find it was a little app that sat on your phone and it listened for emails to come in with a special string in the subject line saying like I'm lost please help and if you sent that email your blackberry would ring even if it was on silent um which I thought was like the coolest thing ever um and I eventually sort of like iterated that like it had a full fledged web interface you could like track your phone on a map you could lock it you could back it up you could make it call you which is a kind of cool feature um and uh and and yeah just I had like a bunch of customers it wasn't like a huge business or anything but it's how I paid for gas and food in high school and um I think what what's really funny about that story is it was a one-time purchase so uh uh like it was like 10 bucks or 20 bucks forever instead of being sass because stripe didn't exist so like it was way too hard to build subscription software um and yeah I would have had a lot more money if stripe had existed when I was in high school so although that's that's that's coming back that form of paying for software so maybe you were just like really really early yeah to that Trend um well I think that's like one thing one thing that's been really cool um working with you is I just think that being able to identify problems is actually really hard not because there's not infinite numbers of problems that exist but because it's actually a muscle to recognize that something that you are experiencing is even a problem versus just your experience your your lived experience and I feel like that's something that I know that you're really good at and it turns out you've been like it's a muscle and you've just been like working on that muscle for a very long time it's certainly a muscle that like I I'm still pretty early stage and I sort of feel like a lot of the ideas that I have I sort of fall into versus um I feel like you have a bit of like a practiced refined muscle of even identifying okay this you know a phone is a new platform that people will need to be able to build stuff on um it's a new interface and yeah it's pretty pretty cool that you've been doing that for so long thank you I really appreciate that that means a lot uh I've I've not really thought about the like the problem identification muscle but it definitely is a muscle I mean maybe it's sort of like partly like my Jewish neuroticism you know I'm just like constantly complaining about things um so I can see the problems um um but uh but yeah it's it's it's been something that I've been doing for a while and um and I actually just love I love looking at the world in that way um uh because it it makes me sort of uh I think there's a way to look for problems in a way that's like oh this sucks and like the world sucks or whatever and then there's a way to look at like the world and see problems and be like but we're empowered to like fix them and that always makes me like really excited because I'm like oh there's something new to do like I have a new project to do you know right right there's also a difference between like so it's it's it's like easier obviously to problem solve something once you're put into a box yeah but it's really hard to identify what that box is sometimes and like so I studied architecture in college and what I got really good at was being put into a box it's like hey here's here's like a building that we need to like renovate or here's a space that we need to put a building on and here's the box and now we can like think about all of these ways to to like solve the problem within the box but we never really were like hey go out and try to figure out what the box even is because then you're just like looking at the whole world and it sort of infinite possibilities and it's really quite hard to like Define a box I think you're totally right and I think that that's like in general one of the kind of things that school doesn't give you and and I'm kind of like happy that I did spent a lot of time doing side projects and stuff as a kid CU I like I had to define the Box cuz like at that point there were no like you couldn't even take a computer science class there were no real business classes for kids like there was nothing on the internet so it was just me kind of like being like how can I do something that would actually work um and so I think that I think that's another skill that's yeah that's really interesting that that you feel that way about the about architecture one of the things that I think is really cool about architecture programs and people who have studied architecture is it's a very like multidisiplinary thing like it's sort of halfway between art and engineering um and I feel like you kind of you kind of incorporate that in the way that you think and the way that you build products and stuff like that has that like how is that sort of affected affected the way you look at the world I think the biggest thing that I learned at architecture is just being uh through architecture is just being iterative and not getting stuck on a solution and like I was the type of uh kid growing up that would like if I had to like write a paper I'm writing it one time and I'm like not even editing it I'm just like writing it and submitting it and uh that's like how I did homework and then I went to college and I studied architecture and I was like oh I'm not going to get to the best solution if that's how I operate like my first design is going to be the worst or the best I won't know until I like throw a bunch of stuff at the wall and it would be a big mistake to try to get caught or to get stuck on what my first solution is um so just being comfortable like iterating I think a lot is is um probably the best thing I got from from architecture and then being able to take critiques a lot of critiques in architecture I bet is isn't it like architecture is like really intense like they're like yelling at you a lot and there's late nights and stuff right or am I wrong yeah there's a lot of studio time I also went to like middleberry liberal arts architecture school which was like kind of like a bit of a janky version of architect I wanted to be an industrial designer um so I just like it was like sort of a path to do that um but yeah it was still pretty hard and uh a lot of feedback definitely so in the kind of like iteration like the thing I'm I'm kind of keying on in the the thing I'm interested in on the on the iteration front is um like how are you taught to do that is it are they just telling you like you have to do a lot a lot of these things or like what is the process by which you you learn to iterate it it's like all sketching it's just a lot of sketching and like I really like computers and I was like from a very young age teaching myself video editing software and um all types of like video effect software and a ton of 3D software rendering software and then I was like great I'll go to architecture school and like be able to use that and that'll be so much fun so like freshman year we had a project and it like immediately brought open my computer and was like great I'm gonna like start rendering something and you know doing and my teacher was just like this is not what we do like you're going to spend the next quarter just sketching and drawing and I sucked it drawing so it's it's just building the muscle of constantly looking at the world eyes wide open and being able to see interesting things like process those interesting things draw them take pictures of them sort of store them away and then keep going forward um and not getting stuck on on them because like any sort of innovation that you have in architecture or even what we do is sort of going to be the amalgamation of a bunch of different Inspirations that you've sort of pushed together and um when you get stuck on something it's impossible to to come up with something new um you're just going to end up coming up with like a derivative of that thing that you're stuck on so for me it was just a ton of it was a ton of drawing and building the muscle of being able to like let stuff go flip the page go for a walk try to think about the next the next thing I love that I think it I think it really also that connects back to the thing you're were talking about for me like seeing the problems to solve like look it helps you look at the world in a certain way and I think that that's always the like first start to doing really great creative work yeah um and you're actually really good at that like a lot of times I'll see you like go for a walk and you've you've told that story of like just talking to chachy PT and using it as like a recording device but one that gives you feedback and um that's like pretty amazing um way to let stuff go and then process through stuff I do want to go back to the fact that you um started a company in college and talk a little bit about that and maybe you could go off on what that was like totally so basically by the time I got to college um you know I had I had built this first company it was called I mean it wasn't a company but it was like it was you know a little business called convenience software and I had all these different apps or whatever and then when I got to college um that's when it was in 201 2010 is when I got to college and that was um right around that time was when Facebook started to really take off um and the idea of web apps and software as a service apps and all that kind of stuff started to really take take off stripe like had just started um I actually had John cson the uh one of strip's co-founders he um he needed a get to get a visa to stay in the US and so he needed to do speaking engagements to like show that he was like legit enough to stay and so he came to pen and like I brought him to pen and he came and like spoke to us and we wanted to dinner with him and all that kind of stuff it was really that's awesome why has he not been on the podcast you like I honestly like made stripe possible basically John if you're listening um no I mean like he used to try to actually like we we kept in touch he he asked me to join stripe a couple times which I said no to which was the probably one of the biggest mistakes of my career career and now that he's a billionaire he doesn't return my emails so um John if you're listening like I love you like come back into my life we'll have you on would love to learn how to use chat GP you owe I mean he owes he owes you he does basically yeah I should frame it that way yeah he does anyway he's a good guy he's a good guy yes um so uh so anyway uh I did a I just did a bunch of projects I was working with a couple different friends doing a lot of different things um but the in my sophomore year I decided I really wanted to focus on building B2B software because I was like I want to build I want to learn how to build a real business like I want to learn how to build something that makes money from day one that I can grow like from school that I can mostly bootstrap um all that kind of stuff and I was on the phone with my dad and he was complaining to me so complaining it's a it's a you know it's a thing um good way to find good way to find startup ideas he was complaining to me about so he runs this um he has a cemetery and funeral home company and so he spends a lot of time he's an entrepreneur himself and he spend spends a lot of time um on the phone talking about um like architectural diagrams and like layouts of like cemeteries and stuff like that and he really wanted something where if he was on the phone he was talking about a diagram that he had he had up on his computer and the person on the other end was also had the diagram up he wanted like a grid to come down from from his the top of his computer screen sort of like Battleship and be able to say like okay like look at cell e five or whatever um and he was like can you build that for me and I was like Dad that's dumb that's a stupid idea um and that's how most great ideas start I feel like um but I told that to my uh who the people who ended up being my two co-founders of firefly which is the company that I started in college um and they actually built the first version of that at a hackathon at pen apps um and we were working together on another another SAS product at the time um and uh they sort of took the weekend to to build that and at the hackathon um a a company came up to them and was like I W we want to use this for our customer service like we want to um we want to uh integrate it so that if people have problems with our website we can like help them through the site um and so they came back and we were all talking about it and we were like okay do we do this or the other one which was the other one was email signature marketing so it's like you could put like a banner ad in your email and uh companies would have their employees put it in and advertise their their you know all their products or whatever um and we're like I don't know like it's hard to sell email signature marketing products like why don't we just like try this one right you got a buyer exactly like you know that's that's like the that's the first thing where you're like oh wow this is really cool what's funny is like they just let us on for like six months and never actually bought it yeah classic SAS B2B buyer yeah I I had a lot I had a lot to learn um and so um so we took a summer uh just like rented a little apartment in um in Philly and like we worked on this Pro product um and by the end of the summer we had like a really well functioning product it was it's called the product the technology we built is called co- browsing and co- browsing is sort of like screen sharing but instead of sharing a um browser sorry instead of sharing what's on a desktop you share what's on a web page um and it's uh and it doesn't require any downloads or installations it's all JavaScript based um and it's crossplatform so you could be on a PC or a Mac or an iPad or whatever um and we applied the technology to customer service so if a customer is having a problem with a website we allow the agent to basically um who whoever they're talking to on the phone or over chat to basically look over their shoulder see what they're doing on the on the website in real time and help them through the site in real time um and it was it was like a very very cool technology um and uh but it was incredibly hard to build it's very very just difficult to like make it work cross crossplatform and cross browser and with any kind of update or whatever and it had to work back to IE8 so I can't even tell you the like the like late nights that I spent uh with my co-founders like trying to fix some like random bug in like IE8 and on like some customers website um truly traumatic um but basically ran that ran that business for a couple years um got got a bunch of customers got a bunch of traction especially for where we were because we were um we were we didn't take any money we took we raised 20K in total from the dorm room fund which is um first round capitals like investing we were the first investment of dorm room fund um and then we sold the company to Pega which is a big public Enterprise software company um and they have a um they have a big CRM that they sell to Banks and insurance companies and they wanted um but it's like you know it's like a five or 10 year sales process that for them that takes like you know it's like a 10 or $50 million sale and they wanted a like Cloud solution that um they could sort of sell as a tip of the spear into those companies and how how old are you when when they approach you and say we want to buy this I was 22 when they approached me and I was 23 when we sold it um I flew from my uh college graduation to Boston to finish uh negotiating the deal and and like take put us in that room you're like 22 you like know nothing B basically I mean I I started my company at 22 and I knew nothing so like you knew a little bit more than me but relatively nothing and so like you're in that room there's yeah I ass you had a lawyer we I mean we definitely had a lawyer during the negotiations um I'm thinking about like yeah I mean honestly I haven't thought about this in a long time but it was basically like the way the way it all happened is is part of the way we got um traction for the business is we sold this co-browsing tool to companies that had big platforms like chat platforms or CRM platforms they would integrate it into their um platform and then sell it to their customers um so we were kind of like an oem into other big platforms and um basically what had happened is um we were uh like working with a couple part and one of them was like Hey like why don't we just buy you cuz like we want this as part of the as part of the platform um instead of like integrating it why don't to just buy the company outright and that was like a really big um live chat customer service company and um we kind of like went through the diligence process with them which was like freaking it was wild like I remember you're in college at this point yeah like going through finals and stuff yeah did you even care care about school work or is it like this is you know nothing compared to I'm selling a company right now like this is crazy I did I I like school I majored in philosophy um and like I wanted to be really well read and so the like really fun part of majoring in philosophy is you just read tons of books and I actually thought there was a lot of overlap between like philosophy stuff and Entrepreneurship stuff because um like at the time the big methodology for starting companies was like The Lean Startup which is like a startup is like science and a lot of for example some of the things that I was like really into in college philosophy wise was philosophy of science which is like what is science actually um and so if you want to do a Lean Startup and you're like hypothesis testing or whatever then you're like oh wait but like how does science actually work like that's we should take that metaphor really seriously and then you're like well then you're just reading lot just for the listeners out there Dan reads like the hardest books to understand that like are simultaneously super interesting and so boring and he just loves them I do it's like it's my happy place to read like extremely boring extremely philosophy books for some reason um um this is like my nightmare I know I like if I'm not reading a three body problem style book it's like look I'm just taking one for the team you know I read it so other people don't have to yeah definitely someone's got to read them um so so like you know so back to that like that live chat company like they were very very serious like I went into to negotiate that deal again still in college and like we were in their lawyers offices with the like you know the like the glass that like it's electrified so like it it's it it gets frosted automatically when you go in and then it like unfrost itself so I was in one of those and like their their like head of BISD guy comes in and he's just like a really like intimidating intense Israeli dude um and uh who who like like rides a Harley and he uh he like plugs his laptop in and I'm trying to remember like the exact words but he had his like Evernote up by accident um and I I can't remember the exact words but it was like um something like be aggressive like let them know that we have other options um like it was something like that like like tell them tell them that they suck and that we have other options right yeah bully bully the college kid that you're trying to buy the company from actually like looking back on that like he was probably in his 30s or 40s and yeah we were like 22 like that's pretty \[ \_\_ \] up yeah that's kind of I mean anyway so you didn't get acquired by them did I well basically we were in the process of of of getting of getting acquired by them so we were going through the diligence even though like you know he was kind of a dick a little bit um or you know they were really pressing us we're going through the diligence and um while that was happening it was taking a while while that was happening Pega someone from pegga reached out and they were like hey we want to partner with you like we want to integrate this in our platform and we were like hey like we would love that but we may not be around to partner with like wink wink or whatever um and they were like oh like well maybe we would buy you and so then we had then we got like a little bit of like a auction going um and so we went through the process with Pega and they were hon they were just so everyone there was like really really nice um and they took us really seriously even though we were like super young which I looking back like deeply deeply appreciate and they kept all their promises um which was really great um and so what that allowed us to do is we went like we were negotiating with Pega and we got into a range like a number that we thought was like reasonable with them and so we went back to this other company and we were like we were like and and then we were like the price just tripled you know just to like see if we could like just get a lot of money for it um and um basically they were like No And so we ended up getting acquired by pegga but it was it was a fun it was a fun what an amazing experience at 22 I mean I went through a similar experience at 208 and it's I mean a really really it's selling a company is a very hard doesn't matter how good your company is it's really really hard to do and to do it at 22 is pretty wild thank you to go through that yeah it's it's hard it's distracting like it's just so emot it takes such an an emotional investment to like do that like it's just hard to like focus on your work yeah I mean I have an anecdote from when I sold my company my my um good friend uh I was so rap up in in Clyde and and like what we were building and making sure that it was trying to be successful and I it was like became who I was um for better for worse kind of necessary to like make it successful um but also not great and I remember my friend Thomas threw a dinner for me as a surprise dinner like two weeks later and um my sister was there my wife was there like a bunch of people and uh I stood up to like give a toast to them for like being supportive and I just started balling I like couldn't I couldn't get it out and then I was like all right I'll like take a breather and I'll try it again in 20 minutes stood up again to make the toast just started balling again I couldn't do it and uh and uh yeah I mean I was like uh 28 and had more life experience than you had at 22 and it I don't think it gets easier you know I think I think if you're really building something you get really really caught up in it and it's hard no matter what to to say goodbye to it to you know it's like a part of who you are it's really hard and it's like it's actually one of those things where like once it was done that's when I fir have my first panic attack um like I was holding my \[ \_\_ \] together and then and then I was started having panic attacks after it was done oh I like so a week after I sold Clyde I got extremely sick and I was like oh I guess it's possible to like just get sick from like stress or something yeah um yeah I mean another sort of I I'm like just not I well I wasn't like a stressed or anxious person I just was able to sort of manage that super well and I went for a walk with Lydia my wife at one point during Clyde and I was just like I don't know how I feel really weird right now and like I I I'm uncomfortable and I can't turn my brain off and like what is I don't know what's happening to me and she like stopped walking and like put her hands on my shoulders and we're like this is called anxiety and I was it was like such an eye opening moment for me I was like \[ \_\_ \] guess I do feel that and it's really hard um no I I I think people should know for context that your wife is a therapist um true yeah yeah but I don't think it was hard to tell yeah yeah I just couldn't tell I I had that too I mean I didn't know any of like I didn't know about any of this stuff until I like literally stopped being able to breathe um like because I was having panic attacks like that was that was the moment where I was like oh I guess I'm stressed I guess I'm anxious because you're just you get very used to just like if you're a Founder like kind of running toward the pain or like running toward the stress or whatever and like it I mean to some degree it's like it's exciting to be have so much going on and have so much pressure and all that kind of stuff and then if you take it too far it gets like it gets to be too much actually I think this is a very good segue to every and like how every started why you wanted to build what was originally super organizers I think both like what was it and then also why did you want to build it yeah good really really really good good question um I spent like so basically I ran the business um the Firefly business inside of Pega for a couple years and then I left in 2016 is and I spent probably like four almost four years like just wandering the desert um proverbially um so I was I you know I wrote a novel I like did some Angel Investing I worked at an incubator um called prehype and um basically in 2019 is I was like okay I I think I just want to start another company like I've tried a lot of other things and I really like starting companies I want to do that and I wanted to start a um like a Tools For Thought kind of business like a Rome notion like note taking kind of like company and I was like how am I going to do that because I had a bunch of ideas for how to do it um and um what I what I wanted to start with was like instead of starting with my ideas I wanted to like um interview like do customer interviews with people to like try understand how they were taking notes especially like really interesting people um and and then try to build a product like around that and so I was like oh what I'll do is I'll start a newsletter um and I'll tell people that I'm interviewing them for the newsletter so that they'll tell me about their not taking system and their productivity system and how they do their email and their to list and all that kind of stuff and then I'll take what I learn I'll write the newsletter because I love writing um and um and then I'll like just build uh build a software business and sell it to the audience um when uh when I've you know built something I think is good and what I tell people is for you know a long time I just got stuck on building the building the newsletter um it turned out like I just really liked it um and it kind of like combined this like um love of writing that I've had for forever and my sort of like love of business and building stuff and and I got really interested in at the time like building business newsletters and the idea that people would pay like a subscription fee for them because it was like at the very beginning of the of the sort of substack Creator economy wave and so I started working with my co-founder Nathan who we'd been friends for a really long time he was the first employee at substack and we sort of together sort of came up with this idea to build a media company for this like new internet age this new sort of substack e Creator economy age where what we saw is a there's like this this like movement of people like unbundling from traditional Publications and starting their own substacks um but b um like that had a lot of drawbacks so they're sort of trading like they're getting a lot of upside so if you if you make it you can like you can make a lot of money you can have a really good business like Ben Thompson probably makes like three million a year like cash or something like that like it's crazy um and it's all profit um and um but what you trade is you kind of like lose a lot of the camaraderie um you lose a lot of the like um editorial support um like you're running a business by yourself like that's a lot um it's lonely and also a creative business exactly exactly and and you don't you can't take a you can't take a break like you have to write every week um there's no Vacations so that's actually really hard and very few people can actually do that um and also the for readers it's it's not as good because the only there's only a certain kind of content that you can write if um you have to write every week or every couple days um you can't write like really big long form pieces or whatever and then um for all also for readers they have to pay individually for each writer so um that's just like not as economical as like just paying for a publication um that has a lot of writers inside of it and so we were like what if we built like a bundle of business newsletters and we tried to create like a single subscription that um readers uh would be able to get access to a bunch of business writers Business and Technology writers that were kind of like the the ones that we liked and then we tried to create a system to compensate um bundle writers that had a lot of the benefits of being on your own so like we had this whole system for like calculating how much bundle Revenue you would get so you could if you attracted more readers um you would more upside um uh but we also had like a lot of the benefits of building together so you know we had a Discord and we were you know we we edited we had an editor and we were all kind of like working together to make each other better and um so that was like the original impetus for every and we started bundling in writers we Collective type exactly so we called it a writer a writer Collective um and so and to the like to kind of tie it back to like my previous experiences like I just gone through this thing with my previous company where um I like loved building that business and I learned a lot from it but I also like wasn't passionate about it like I it didn't matter that like co- browsing is cool but it's like not my like life's work or whatever um and what I really wanted to try to find was something like an like a business to run or to start that like had that kind of like upside to it but also um just I just loved like it just kind of like pulled at my heart a little bit and I felt that way about this and I still I still feel that way um it like you you talked earlier about like the creative playground and I think that's what every is and it's like that is the best it's so fun to like wake up every day and do that um and it's just it's a different feeling than like um the B2B SAS stuff which is cool but it's like it it it to me like the the core um of every feel it feels different it's warmer yeah yeah and and so and then where did that go wrong like the collective idea so the problem that we found was um there are very few writers that can actually like make it on the internet and there are even fewer business writers because in order to like be a really good business writer you have to know what you're talking about uh you have to be able to write you have to be able to do it all the time every week or more at least at least weekly maybe more um and you have to want to um and those four things are like very very very rare so um especially especially in the business world one of the reasons why there's a lack of like really good business technology writers is because if you really know what you're doing business-wise you can make way more money like just working as an ex executive or like starting a company or whatever like their the upside is like way higher for anything other than writing so there are plenty of people who probably could be business writers who don't because it's just like well I'd rather I'd rather have a like make money which makes sense um and so uh and so what we found is like basically we started the company we were the main writers when we started it everything was growing we were like cool we'll just go like higher now we raise money it's like a real business now instead of being the writers we're going to go hire writers um and as soon as we started to do that the business just start stopped working because like the the weird like hard thing about media is if you have product Market fit with a particular writer and then you change the writer um the you lose product Market fit um and and writers are the rarest thing like good writers are the rarest thing and so the business started like going like this and we were just sort of following the Playbook that we had learned like running our previous companies but that's one of the key differences between media and software is in media it's like a it's a best practice for the founder uh sorry in software it's the best practice for the founder to be Technical and like build the first version of the product and then you hire people to like build the rest of it and in media that doesn't work at all um uh for the for the reason I just talked about so for a while the business was like sort of stagnating even though we were we had other writers doing it um and then through that whole period we like found one writer who was like good enough to like really sort of be part of it and help carry the um the publication or what became the publication uh his name is Evan and he he writes napkin math for for every but over time what we found is like um the idea of of having this like scalable Collective of like all these different writers like just didn't work because the the supply constraints of writers were like really hard to work out and then also just like figuring out the bundle economics was really hard bundle economics are just just it's just like it's like a mess basically um and everyone like there's the system gets complicated and everyone's unhappy and whatever so it's like it's very hard to do a lot of people do it because it's like it's a great business if you can make it work but it's hard so um so anyway So eventually we kind of like realized yeah what we're really doing is we're not building like all these different newsletters CU like only a couple of them only a couple of the writers are really working we're really really building like we should really just build one or two one newsletter and like have the have all the writers that are working in one place um and then we can have the other ones that aren't working as well like we can have them contribute but we should just like be focusing all all our effort on like the winner or winners basically and also like around that time like I kind of made a decision to that I wanted to write more um and that also like helped a lot cuz um that's like I love it it's a thing I'm I I I love doing and and I'm pretty good at it so I kind of like made the decision instead of like doing the typical CEO thing and like um hiring other people to do like a lot of the on the ground work um uh that I would also like be uh a or the main writer I think that is actually a really important point and also kind of like part of why I wanted to join every to which is like you felt like the need to not write because you're supposed to like scale the company even though it's what you're good at and it's what you like to do which is like just to rate it's what you're good at what you like to do yet like you're supposed to not do that and I think that like one thing that I just loved being here at every is I don't know if I could say this on the podcast but like that like you should just do the thing that you're really good at and you like to do and like you can just it just feels like such an unlock to be able to with confidence do that I feel like a lot of my first company building experience was like oh I'm supposed to manage my board like this and I'm supposed to hire in this way and we're supposed to build product with three engineers and one designer and one PM per pod and I it's Brian chesky actually has a great talk about like designing your company and um I feel like that's exactly what we're doing here and it's just it's very it's a better business and it's more fun yeah totally I think you're I think you're spoton it's and it's it's sort of like that's that's what I did with my first company too in a lot of ways and like it's I think it's part of maybe being like a younger entrepreneur and then and but some people never grow out of it and I think what what we're trying to do at every is like actually like look at what do we want to do like and who are we and how can we make this thing a reflection of that um instead of like being like what are we supposed to do you know and and and for me like that has been a journey because I feel like I'm constantly like fighting that tendency in myself to like pick up other people's expectations and then like try to fulfill them regardless of what I want and it's it's taken a while to like figure out how to do that I'm still I still failed it um often but like I think it's it's becoming more like that which is really great um yeah so okay so so uh every now this s like one newsletter actually if you're an every subscriber you can actually like see the Legacy you know all of the columns still on through the account creation part of the the uh the the website um so this changed to be like sort of one newsletter and then I mean now it's evolving a lot in the past four months I feel like there's been you know sort of unbeknownst to a lot of listeners and readers there's been a ton of transition and evolution that was announced in the every master plan uh article that you wrote but like maybe you could talk about that a little bit yeah I'd love to talk about it I I also say like in that kind of like all that sort of the messy middle period um uh my co-founder Nathan built this app called Lex um and we were kind of we we spent a lot of time in um in Google Docs like you know editing writing and all that kind of stuff and he was like very kind of like maybe there would be a better Goog Google Docs and it always been kind of like in our mind to like build little products like because that's sort of where the the original idea for every came from and um we'd done that along the way and so he started he started building what what became Lex um and it was right around the time where gbt 3 was like starting to take off chat gbt had not been released yet we were like it would be kind of cool if you just like put that into the into that word process reming so he he built Lex we launched it and it just like went super super super super viral and um and we spun it out as his own business so he now runs that it's still part of the the bundle that we offer to our subscribers um but it's a separate business and I think that was another accelerant for me to be like what do I really want like my co-founder's gone like this is every business has a bunch of different like reinvention moments and I think that was like a that was a reinvent moment to be like okay like what do I what do I want and what do I want this to be and like who am I and all that kind of stuff so i' I've written a lot about that and that was part of the process of me being like I think at the core like I'm like a writer you know um and um and I think actually what what what I'd love to do is like because there's there's this kind of like every master plan but before I wrote that article like we had you like you joined um and I think it it would be nice to like talk a little bit about that and that process and like um I don't want to I don't want to Swerve the whole thing but like one of the things I'm like uh I'm wondering because we got to talk about my origin story and I don't think I even know your origin story like obviously we've been friends for a while like you you sort of came on to every after your last business but like how did you end up how did you start how did you start getting the entrepreneurship thing like what was the what were what were the origins for you yeah um well earliest days it was like sort of classic taking stuff apart you know building stuff with Legos in in my my earliest days um I can't I've always loved making stuff but it was always with my hands um but I was never good at math um and I so I I I ended up going to um a liberal arts college called Middlebury in Vermont and um pretty much the only reason I chose to go there was because they had they were a part of a competition called the solar decathlon that the department of energy was putting on and the the challenge was basically build a house that's entirely solar powerered um you have to fly it train it drive it to Irvine California build it in 7 days there's a competition of about like the Aesthetics of the building how well it performs like a whole bunch of different things and then you have to take it back to you know do something with it um and like we were typical participants are like team China team you know entire countries are like huge universities and then somehow Middlebury which is like a 2,400 person liberal art school with like not really an architecture program and certainly not like a constru instruction program or anything they applied got accepted and then got the school give uh you know this team one and half million dollar of funding and I uh somehow learned about this and was just like this is the coolest thing ever um and I I mean I toured Middlebury on like a crazy crazy snowstorm and was like this is I love it here like and I think it was in part because of Sol cathlon I landed on campus freshman year and just like that became my world and I taught myself AutoCAD and I sort of became like our strategy for building this this uh we wanted to make it like a really really efficient house and that included how we were going to get it to California and if you fly a house to California that's like a lot of gas burned if you drive it that's a lot of gas burn but if you train it um it's really really efficient to put stuff on trains so the challenge for us building this house aside for making it efficient and beautiful was it had to be panels that were like no wider than 7 feet nothing could be wider than S feet so that heavily influenced the design and then I sort of freshman year no experience with AutoCAD or architecture it was like I'll teach myself AutoCAD and I'll sort of be the guy who makes like all them all the schematics so I made essentially the the blueprint for every single panel became sort of a really really core member of this team which was you know primarily had seniors and then there was like the 120 pound freshman Brandon um who like knew nothing and was like super young and um I yeah it was just stayed there that summer we like literally built the whole house and I was like a very core member of the team and and that that was sort of you didn't at Middlebury you didn't have to pick your major until sophomore year and I was basically like I love architecture I love building things I did a lot of building buil a bunch of furniture I like got really close with a bunch of people in town that were like metal workers and you know Woodworkers that helped us build the house so had access to all of their Studios and would go to their their shops and build Furniture um and then uh my senior year uh I did two projects that were really really influential what I one to do next one of them was um I had gotten close with this um girl who was wanted to build a bus she wanted to like renovate a school bus like a 52 foot yellow school bus but had no construction experience and I basically came on board and the two of us bought a school bus gutted it over the course of like two weeks and then completely renovated it into like this beautiful school we turned it into a mobile school that taught entrepreneurship and she went on and like toured the country in this bus um and had an amazing experience so that was like another really Hands-On thing but at the same time I sort of started to get drawn to graphic design and then um me and a really good friend sharf um who you've met uh went on and and another friend of ours DAV went on to build a photo printing app called Photon and the idea was we all take a lot of photos we never look at them like wouldn't it be great to very easily print them um I think if we had done like a second of market research we would have known that like Shutterfly existed but we were like we're going to do it on our phones and it'll be really easy and you know super low barrier to entry for people to print photos um yeah that didn't really work like my Aunt printed a ton of photos um but it was an incredible experience we learned a lot and uh and that's sort of where it all started and then I became a vfa fellow and went to go work uh for a startup out of Columbus Ohio yeah I I think there's I mean there's so much in there I mean one one that like sticks out to me is obviously just like the feeling that you love building which is such a core like part of being an entrepreneur is like like loving building things but the other thing that you said that that really stuck out to me is like like um I was this freshman everyone else is seniors and like I just like taught myself AutoCAD even though I didn't know it and I think that is such a core like entrepreneurial trait that you're so good at it's just like I don't know how to do this but I'll figure it out it'll be fine yeah I think everybody who's builds needs to be down for that yeah yeah it's kind of a weird totally unworked level of confidence that you shouldn't have but I don't know it's just yeah you have it too you have to yeah you kind of have to um and um and it's surprisingly it's surprisingly like I mean Maybe not maybe not surprisingly but it's rare it's rare to be like there are no there's no manual there's no instructions and like I'm pretty behind and I need to like figure this out and that is actually appealing to me instead of like being so overwhelming and stressful that I don't want to do it um and I've just I mean I've watched you do that like over and over in in the work that we've done so far um and it's like yeah that's it's very impressive I think yeah just being curious is like such a core part of I think being an an entrepreneur and um and uh it's hard to be that without it's hard to be an entrepreneur without having that Curiosity because there's just endless problems yeah you have to love problems yeah you can't be intimidated by them you have to be energized by them yeah okay and so you did so so you did you did the photo app what was the impetus for that like because that was the first thing that you mentioned that like looks like purely like a business um yeah I think I was just sort of like getting I I know that I had like downloaded like a bootleg version of sketch um and was like cool I actually really like graphic design specifically mobile design and um I had gotten close with Sharie and Dav who um are both really talented engineers and back then were like cops ey Majors um and we just were like we want to do something and then I think I literally was like what I like photography like let's print photos and that was it and then we did it uh not a lot of thought went into it but it was uh I mean there's there's big photo printing apps now so I think if we stuck with it and knew what we were doing you know could have gone somewhere honestly I think like sometimes less thought is better especially at the beginning cuz like it's so easy to just like psych yourself out and convince yourself it's a bad idea and then never do anything and like the whole point of at that early stage of doing stuff is not because it's going to be like a a huge thing off the bat it's like which would be nice if it was but like it's just learning how to like make any kind of business like the fact that your aunt used it means like you shi something which is like the important thing right we shipped and that is pretty much exactly how I started Clyde as well um although I knew at that point that was going to be like a bigger opportunity yeah um but yeah it is important just to be like whatever let's do it I have a feeling um okay so and then so after that you then you did vfa and what was that like I did vfa R RIP just shut down actually I saw that um yeah uh so yeah did vfa played a bunch of basketball with Andrew yang actually which was like a fun fact yeah he's a really really good basketball player um and uh yes so I went to go work for this really cool startup out of Columbus called knockout Concepts and they were designing and building a 3D scanner we were a four-person team I think I literally like chose to go work there because they had a really cool office it's like in a warehouse they had a ping pong table and I was like this technology is cool too and I really like 3D design so this is perfect um um and yeah I was like trying to figure out how to bring this product to Market and that meant Shopify like very basic stuff shop we were going to launch it on Shopify we needed it was expensive so we needed like some financing so we launched a firm it had a software component that like people needed to pay for so we integrated with stripe and all of this stuff is like on a whiteboard and we're just like I'm sort of Crossing them off and then there's um an insurance offering because we had this idea that like it's a $3,000 product people will like they're taking it into like underground you know piping gas companies were using it to like scan pipes we're like they're going to break it and we like have no money so we can't really afford to like replace it so let's get you know offer insurance and Shopify affirm and stripe are like these amazing really simple experiences and I expected an insurance offering to look like that and like did a bunch of Googling didn't you know find that and this is where that like sort of uh acknowledging problems part of you know me wasn't yet really built out because I didn't sort of recognize immediately what I just recognized is this is annoying now I need to go talk to an insurance company six months later I sort of got there and was like these insurance companies are awful the people there are like not really that enjoyable to to to work with right now the experience that they want to give my customers is not going to be good there's zero technology when I'm asking them for like API docs or anything they don't even know what those are and that was sort of the beginning of there's an a there's an an airm version of this product um and then the naive of you know a 22-year-old that doesn't know much to be like and I'm going to solve it and I'm going to build an insurance company um that's and you know super privileged to be able to do that and like have the backing of my parents and I live with my grandma for you know a year while building the first version so very very lucky to be able to do um that but yeah took a while to figure it out and so yeah like what what was the like yeah just like um kind of like give us the like high level elevator pitch of of Clyde yeah so um Clyde made it possible for any business to launch their own extended warranty program so um if you think about Apple Care Apple generates an incredible amount of revenue from that their customers really appreciate it um they're big they can convince an insurance company to back the insurance po policies that they sell which they actually do they don't take on any of the risk they work with an insurance company now if your knockout Concepts which was pre-revenue um it's really hard to go to an insurance company and say hey you should put in all of this work to back my products there's no data about the quality of the products and there's no guarantee that that insurance company is going to make any money from it um what I didn't know at that point was that even like a Dyson wouldn't be able to go to an insurance company because an insurance company is like I can launch Five programs a year um because it takes an army of people at my at the insurance company to launch these programs so the um value of each program needs to be super super high so what we essentially realized was like well why don't we just make it super easy to be able to launch this like a Shopify app or like couple lines of code and why don't we build this Marketplace of um insurers that we can like very very quickly match policies that they've built to products um so to launch with Clyde it took you know it could take 30 seconds if you're like a Shopify app or if you're a Dyson um unfortunately it could take a very very long time but not because not because of the uh development work just because of bureaucracy yeah um and I think it was around the time where you were like building the first version and raising the first money for this that we met um I think you came into prehype which is the incubator I was working at and I and I was at the at that point doing some Angel Investing and I remember seeing the pitch and really liking it I don't remember I didn't end up investing but I don't remember why because like my only memory of of like the pitch and the aftermath is like I was really impressed by you and I was really impressed by the like updates I was getting from you and I it it was in the category of deals where I was like the one that got away or something I think I just took too long to respond to an email or something like you were raising around it was like closed and you and it was like I kind of just missed it and then I just felt bad about it but like what I remember is I see a lot of pitches and I think you had this really really special combination of you were super ambitious like there was a big vision for what you were doing um I felt like the business was actually like really like intellectually like rigorous like you had really thought through the the like the landscape of like why there was a problem here and like how to solve it and stuff like that but you were also very um just like straightforward like I believed you you know like I didn't feel like you were like \[ \_\_ \] around in any way um which uh is very rare like to have a that combination of like um I'm ambitious and really motivated but also I'm like pretty straightforward and like I'm not like you know I'm not putting on errors or whatever or trying to be something I'm not like I'm just am this is this is what you see is what you get more or less and I really liked that yeah I mean I when I look back at that time I just I could it was very very focused you know it was like this is the only thing that matters right now and like going on dates because I just moved to New York um and I was really excited about that too which tell people about your your dating strategy just really quick which one oh good the uh you told me that you would go on like uh I think early early morning dates or oh yeah yeah I was like I was very focused on like if somebody wanted to like get a drink after work which like I wasn't super into I'd be like how about a 7 a.m. coffee and some people were really down and others were not and they weren't good fits um and then my other go-to which I didn't tell you was like sometimes I'd be like uh I really want to go to this bath house and do you want to come to this bath house which I think you've been to I have well I mean I which one the the one in East Village spy 88 oh spy 88 I've never been to that one only one person was down and it was a really good date it was super fun I I think that's the spa that uh either hberman or Lex Freedman likes but i' I've never never tried it yeah okay um see yeah I just remember looking back at the time and being like it was just so focused on making it work and and uh it was really complicated because we weren't just building a software product we also had like these pretty big Insurance deals that we needed to close to like launch the business and I remember being really focused on um signing uh uh deals that were um what's the word I'm thinking of I didn't want them to be exclusives so like we got a couple offers from these insurance companies that were like oh we're just going to bully this startup and just tell them it's exclusive and we had to turn them down and it like created all of these unknowns of like are we going to be able to find a partner um and I think it's important when you're building like we had a vision for like a Marketplace and we were like this is going to be better for consumers cuz it'll just be cheaper and cheaper and at the time we were kind of like \[ \_\_ \] these insurance companies like they should be making as little money as possible which in hindsight like doesn't really make sense because they need to like make some money um but we did that and I'm so happy that we did because that became like a core part of our offering and a Competitive Edge um but it was really really you kind of in those early days need to like be able to say no even though if it potentially jeopardizes what you're building yeah totally um why do you think you had the confidence to do that at 23 or I don't 20 22 something to say no to those deals it just sort of felt like it would be worth it otherwise I think um like we would sort of be stuck and there I mean there were definitely were days when we were considering taking it just cuz we needed to go and you know I was making 18 Grand a year let go with my grandma um and and that was after not making anything for a long time um so I think it was just like what's the point like this is going to be so hard anyway we should just try to do it right makes sense um and I guess like so tell us a story of of the business because we're we're starting yeah we're starting to get into like the meat you spent seven years running that business so you were trying to into the meat of it what's what's the what's the story how did it go the story of the business well I think it's like actually a bit of a cautionary tale so we in when I was 22 we raised 3 million got an office hired like maybe we got up to 12 people and um we had like the product and it was making money and we were growing and I think that we thought that we had product Market sh but I don't think we understood at the time the Litany of challenges that this type of company and this type of product were going to encounter namely competition which I didn't exist when we raised but like existed soon after um time to Value which is when you close a deal how quickly like will let that business start generating money for you because we had a product that people needed to Implement um and then last one is spending money is very um it could be dangerous like we had money to spend and therefore we spent it and we were encouraged to spend it so what happened soon after is like we didn't really know all of the the Dynamics about how the business worked yet we were like finding success with growing our clients and growing the number of clients uh but soon we needed to raise again so we raised 14 million um and it's this sort of pattern just kept continuing we raised we had more money so we spent the money we grew our clients but we you know now there was a new dynamic in place which is like the economy was changing a lot um and then same thing happened we had to raise again we raised the uh B and and then the economy like started tanking because the pandemic had just hit uh but then everybody got $2,000 so uh even though the economy was like kind of not doing well people were taking that $2,000 and spending it like crazy so we saw our business just totally Skyrocket um even though what we i' I'd say the core problem with our business uh was is n changing and that problem is if you close a big deal takes a long time to launch that deal which is I think like a cautionary tale for any B2B business that requires implementation and why why is that such a problem like what is um what causes that to make it hard to make the business work I'd say there's two different challenges so the first one is at a lot of these big retailers the right hand's not really talking to the left hand um so you've got sort of these business people that are out like trying to drive Revenue are probably compensated on driving Revenue but then you have the technical team that needs to implement what the business people have you know decided to do and what we found would happen pretty often is like a business person would be psyched about launching Clyde because they were going to make really high uh margin revenue from it we' sign the deal and then uh the technical people would be like who's Clyde we're not ready for this we've got like a bunch of other stuff that we need to work on so we'd have to resell again and there were things that we did in our sales process to try to like stop that from happening um like including technical people in the deal or in the sales process um and then the other challenge is like I think especially in retail is it's just a freaking mess like people use different erps these erps are really Legacy so like no one there really knows how they work they're using different you know headless software and different e-commerce platforms and um I think one thing I learned is like if we had just decided to be the best version of this company only for Shopify we would have been a more successful business than if we tried to go after every single thing and that I mean that's just like a very hard lesson to learn about Focus yeah like Bo boiling the ocean like maybe the market size total Market size is bigger but it's sort of like it's a little deceptive because um The Divided effort means you don't get as far even if the Tam is higher yeah and then eventually we we uh we were like we either need to fundraise or we need to sell and we had a bunch of buyers that had come to us and expressed interest so we ran a sales process found a buyer great company called cover genius a competitor out of Australia that was like trying to break into the us but kind of struggling super aggressive sale and they didn't really have that muscle and we did and it was a great fit um and Yeah March 14th I'll never forget signed the deal it was like a couple weeks after svb shut down which was a whole other oh my God this this was like a crazy four weeks of selling this business and what was it like like you know the moment you signed it cuz I remember I remember selling selling fireflag I remember that moment like what was it like for you I mean I remember signing it and like we were working out of cover genius's office doing going through diligence and just it was really collaborative they were amazing to work with um and I remember sort of like I had our CFO and an accountant there kind of the guy who could like really go through a lot of our data and make sure everything was clean while we were building out the the data room and we all hugged and and then I went for a walk alone and was just sort of I don't know I'm like emotionally even thinking about it it's sort of like this I remember that walk feeling simultaneously really freeing of like I had done it and also really um kind of just like but now now what like who am I and I know that I have I know that I have like this challenge ahead of me and uh um yeah it's really emotional yeah I feel I felt that too and it's such a it's such a weird thing because you also feel like you should feel great you know um and um and there's not really like a playbook for it um like I think for a lot of Life moments it's like you graduate high school okay now I'm going to college uh you graduate college it's like now I get a job but I think the one of the interesting things about the entrepreneurial path which is sort of like designed very unstructured is that when you sell like there's not that next thing for people and you just sort of you can like fall into this like black hole of like I just lost my identity I lost a thing I do every day and like what now and there's a I mean it is sort of like a cliche thing but it's also just like actually just totally real like it's very hard oh I mean it's like such champagne problems like you just sold a company and now you're like but who am I and that was also really hard CU like what ends up happening is everybody can grab congratulate congratulates you and everybody asks what you're building next and I was like the way that I described it to this feeling to my friends and to my family was like I can't hear the music anymore and like the first thing that I'm going to do is go to try to like hear the music again um yeah that's hard now I can hear the music though so so but it's been it's been a journey yeah so it sounds like you're um like a little Shell Shocked or something like just you know a lot of um uh like going through like it the the image I have in my head is like you someone put you in a in a dryer on like the you know the perm press cycle or whatever and you were just like tumbling around for a while and then like someone took you out and we're like okay you're done now what everything got calm it so Clyde was not a calm business and then everything all of a sudden got really calm and that was an incredible feeling but it also was like it took a solid like 3 weeks of just decompressing from that state um where I cried a bunch I got super sick like you know all these things it like I needed to process it um but I totally do it again I mean it was like so cool and I met amazing people and like I mean we are doing it again so that's a really that's a really good transition into um like how you came to every so you you'd sold Clyde you're kind of like trying to listen trying to um trying to hear the music again um take us through like how we started working together yeah so I was very similar to you sort of like stumbling through the desert trying to figure out what I wanted to do next um my wife and I did sort of like the I feel like the classic thing that like maybe exited Founders do which is like we moved to Nicaragua and I did a bunch of Surfing which really weird saying but it's true and it was amazing um she was working um and I was uh I had sort of like wrapped up my time at cover genius and was experimenting with a bunch of new ideas um so I was working again with like share who I built photon with and we were trying to find problems which was really uh in hindsight like not a good idea I just feel like when you're when you're when you're trying to find love like that's not where when you find love um and it I think it's the same thing with problems I guess uh but we didn't know that at the time so but one thing that we uh were really good at and we love doing was like having an idea and then building it super fast so like figuring out if people were going to use it trying to get some aversion in their hands I got banned from Reddit like 10 times during this this period to like try to talk to people um and that was like I just loved that um we didn't come across any idea and then like his life took him in a different direction he needed to move somewhere and we just didn't end up uh this time around didn't end up working out for the two of us and again I was sort of like back to the desert uh trying to figure out what I wanted to do and then I got uh I've been an every subscriber for a long time and I got uh a article in my inbox uh it was uh it was called decere not Ser what was it called oh yeah well so that's actually that was actually something that I got a while ago I got be sincere not serious when I was um still running Clyde and that like changed my home mentality this was about the billion dollar solopreneur so like it was a napkin math column about is the billion doll solopreneur actually even possible and this was when like Sam Alman and all his poker friends were like betting on is it possible it was like all over Twitter so you guys did a column about like is it actually possible and Evan basically netted out to like no it's not possible um and it sort of was a light bulb moment for me of like what about building I really have liked the sort of like Studio aspect of what I've been doing where I get to like experiment with different ideas and move really quickly and um I realized two things one that doesn't matter if you can build stuff if you can't get it in people's hands which I was really really struggling to do to get people's feedback and then to like get users and every sort of had this unlock moment of well every has that they already have distribution um and then I had this other thought of like well maybe we could get people to build a billion dooll business solo if they just had the right tools and like maybe there should be a whole product Studio that exists to like just build those tools to enable the billion dollar solar preneur I think that's what I wrote in an email to you you did so I was like what's up Dan it's been a while let's pull up the email let's pull up the email yeah I remember being so psyched to hear back from you and just being like I really had this feeling um when you responded of like the this might be my future seriously all right I've got the email so what I like about this already is like that subject line long time no talk considering my next move it's like I I have to open that like come on like who's not gonna open that uh all right hey Dan it's been a minute I just read the one person billion dollar company was inspired to reach out when we last hang out we got a drink at Spring lounge and you were telling me how every was just beginning to take off that you needed to take it off substack and then you went on a few dates with someone and were psyched about them I can't remember where I was at with Clyde but it's all blur I remember getting drinks at Spring Lou that was fun yeah you were like you were gushing about this girl you were like this I found him this is amazing um spoiler alert didn't work out but and I think at the time you were in like Peak Clyde stress you were just like oh my god really I don't I literally was all a blur yeah uh I sold Clyde in March of 23 um wrapped my earnout I took a bit of time off but quickly got out to work with a buddy of mine from midbury un building out a tiny style Studio building smaller profit driven internet products that we that could s on their own it was super fun and we were Off to the Races um but unfortunately he had a big life shift I'm picking my head up to talk to people from my past that are working on products I love and use regularly I thought I'd reach out to see what your PL are with every and how I might be able to plug in I've seen that you're actively building small tools here and there and I'm wondering what your plans are with them with building more products for what I can tell every seems like an amazing platform from which to build out a studio or fund I'm sure you thought about it this already but I'm I'm curious to here hear your take which I was I got that email I was like \[ \_\_ \] yeah I've been thinking about this for forever like this is amazing um and uh uh I said very interested in incubating new products at every and I have a ton of ideas would love to hang so that was the beginning of it um you you had this like you had this brain wave you you told me that you were like I think you were in Nicaragua when when you sent this email right yeah yeah I was in Nicaragua and then so I sent that email you responded and I was like this is going to be so much fun if it could work out and then what I did was I went for a walk on the beach um and that's where I laid out like uh these like three pillars of every that like I thought could exist and I thought maybe i' would be a good person to run them and like why I would enjoy doing it um I don't know if we want to talk about those let's do it yeah bring them bring them out okay so the first one was like Consulting it just sort of was like felt obvious to me that a lot of people really respect every and you're the business is so knowledgeable on AI and led by you who has a lot of experience you know building companies and being entrepreneurial and with the sort of addition to me there's two of those people um and that could be pretty powerful so like maybe we could do Consulting there was this other sort of core idea which is uh well we should just build more products we should like build a product studio and maybe the theme could be apps software to enable the billion dollar solar preneur um we didn't really land on that but like the idea was to build a studio and like a profit driven Studio and then the last one which like we're furthest from but I'm still think would be amazing is like we should invest in companies because VCS not all of them are great and um we're two people that have a lot of experience we understand the journey the founder journey I think most importantly and every just has like clout so like I just felt like we could get into any deal that we wanted to get into um so these were the three pillars I like iot wrot him down in a notion dock I Pro I I can't find it it'll take too long but I wrote it down and I sort of wrote down why I thought each one would work and it kind of going down exactly like I wrote it basically it's going to plan which rarely happens so it's pretty sweet it's pretty sweet it honestly like it has felt so like so basically like when when we first started talking there was like a there was a little period of like okay what's the deal like how are we going to work together uh one big thing was like how are we going to fund this and we decided like okay why don't we just start with some Consulting we'll do some Consulting and then we can use that to fund the studio which is like a it's a risky thing like it's hard to start two businesses at once um and that has just ended up working really well we've been able to do some really awesome Consulting work helping big companies train their train their people on AI um and also just like know which AI products to buy and and and work with and Implement all that kind of stuff and it's been it's been amazing and the studio stuff has been incredible um so we've launched um two products spiral um which helps uh helps people automate 80% of their creative work um by uh basically it's a sort of like a powerful prompt Builder so you can you make a spiral for me I use it all the time for this podcast actually to uh convert my podcast transcripts into uh into tweets um and Linkedin posts um but it's used all over the world by all types of different people we've got about 4,000 users for that and then we just yesterday launched Sparkle uh which is an AI file cleaner so it um it it uses AI to make sure your desktop downloads and documents folders are clean um and that that launch was amazing and um it's just been kind of like I honestly feel like um you know in the uh in Star Wars where like in the Millennium Falcon like they do the like jump to hyperspace and all the like the Stars like start blurring like that's what it has felt like since since you've joined it's been like really incredible like you've just like totally like just raised the level of our execution and our Pace like dramatically it's been super fun I mean I think that like one of the best parts of being here is the quality of person that we have at every is just so high so the quality of people that were already here um and then the quality of people that it seems like were able to recruit fairly easily is is such a competitive advantage and um and then also like the mentality of the business is build calm businesses and if we're I mean I feel so passionately about this like if we're not having fun then what's the point and we've so far been able to maintain that it it has only been four months but it it feels like we've done the work of like a couple years honestly um which is so exciting and and uh yeah it's working it's working um and and I think that's this is a sort of like I think good time to kind of like bring up that that Master Plan thing that we uh we swerved off of like I don't know an hour ago or something like that um but basically like what it has sort of turned into is this um you know every started as this place where we wanted to make great business writing and I think we've business and really Business and Technology writing and and I think we've grown and changed a lot in like how we think about doing that because running a media business is like it's just really hard it's just really hard to make a good business and um what I care most about and I think what everyone at every cares most about is like that create making that creative playground place where people come to do their best work um and building a building an institution for the kind of writing that we love um and and extending that into podcasts and courses and software and all that kind of stuff and what we've kind of figured out as a model for doing this well and doing it sustainably and doing it in a way that you know doesn't end up being like all these media companies that like raise tons of money and then blow up or um whatever is um kind of at the you can think of it like a pyramid or what we what we what we talk about it is sort of like this pyramid it's it's not a pyramid scheme hopefully but it's pyramid um and at the bottom of the pyramid is um basically all the writing and the podcast that we do the the the things that we do the high quality things that we do that are free that get people in the door and get people acquainted with every and then a a level above that is the um the every paid subscription so that's the $20 a month subscription that we've we've had since the beginning where we bundle things together so um right now every the every paid subscription incorporates um all the writing that we do um access to sort of behind thes scenes stuff from from the Pod this podcast um discounts on the courses that we run um you know and and then also access to all the software we build so there's access to spiral Sparkle and Lex um and with more coming um and the idea is like maybe like hundreds of thousands or millions of people interact with our free content and then maybe tens of thousands or hundreds of thousands of people end up you you know subscribing to the every subscription and then a layer above that um we do training Consulting and courses and far few far fewer people do that um but the you pay far more um and then above that is like speaking or advising or or other other kinds of things which are even more expensive um and even fewer people do that and that seems to be like a really nice and we can sort of take the cash from the top of the pyramid and funnel it down into making more writing or building more products or whatever and that seems to be like a structure for a media company that's really focused on making really high quality stuff that works and and I think it's actually quite counter to what you learn when you're building like a more Silicon Valley style Tech business where um you know the recommendation or the thing you're supposed to do is like focus on a business model and just like just make that Crank that just make that work right um and I think what media companies need to do is you have the the the core asset you have is sort of like the audience and their relationship with you and the affinity for you and all that kind of stuff and different members of the audience want different things and can pay different amounts and you need to have different products for those different people and what we're trying to do is like build a structure that allows us to to build different products for the different people that that um that are that are part of this audience and it's a pretty like it's a it's a big bet it's it's a bit different um but it really it honestly seems like it's it's working in a way that's like I you know it things almost never work this easily so I'm almost suspicious but it's really working it's pretty great well I think there's a lot of like there's there's a lot of things that like have already been set in motion that are now playing off of each other and it does all come back to the sort of foundation of this pyramid which is like every has really high qu quality content that a lot of people read and listen to and that is the engine behind the whole rest of the business it just doesn't work without that and um and that's also why like to the very first thing that we spoke about it's like you should be writing and you should be talking and like that's what you're good at and that's what you like to do and if you didn't do it the like the rest of the business just wouldn't work um and this is like a model that uh I feel like is like very big on Twitter and people are now beginning to realize like oh distribu when intelligence costs zero dollar basically like it's distribution that's important and this is like this new thing that a lot of people are talking about we are in a very unique position I think where um were actually leveraging that and thankfully had every sort of buildup before this model became like a real concept and we just sort of cranking it um and trying to move really fast on it it's sort of like I mean you know the new yor I don't want to compare this to the New York Times but like the New York Times sort of like went backwards into this they realized that their their media business kind of sucks and then they're like they build a bunch of apps uh to like that people really want to interact with and let's bundle it all together um and but they are sort of like the the a really good um a lot of their content isn't free but some of it is uh and they're a really good sort of model um I think to base off of and another thing that they do that's just like I think a model for us not that we really talk about the New York Times ever is their level of quality is just so so high and I think that's really important for both of us is just everything that we put out we want to look really good work really well and actually have value we're not going to put it out if it's like some \[ \_\_ \] um which hopefully we can maintain that'll probably be the hardest thing to do I think so yeah I mean I think I think that that's a risk I think also the risk is like all these different levels of the pyramid like to some degree have different incentives and so keeping everything aligned um and supporting each other as things go on is is also going to be like a really interesting challenge um but I think one of the things that I really like about every is um we haven't raised a lot of money so like there's not a lot of external pressure and I just like love everyone that we work with like I love everyone on the team it's such a good feeling team like there's some little magic thing happening right now um and I just want to like keep that going and I think if we can keep that Core group of people together and and not um I think we like we push to move like really really fast but what we're not doing is like you know going and raising a bunch of money you're like hiring like 15 15 people in a week or whatever like that that kind of stuff um you know you talked about sort of being calm and I think like when you're launching as many products as as we launch like some there's definitely some some stress involved but like the there's that sort of like core thing where it's like partly we're doing that because it's fun and we do get to set the pace and um and what I don't want to lose is the kind of creative playground like we're doing really high quality stuff like that's the point of all of this and um I I think we've got I think we've got a shot to do it because I think we have a we figured out a structure that works to support it and um um I'm just I'm psyched about it yeah speaking of which if you're a technical founder or you're a technical person that wants to build stuff you should reach out to brandon. do that um yeah we're looking we're looking for more entrepreneurs and residents to work with us on on some of this stuff so um we're getting close to the end here but I think we should you know obviously in this show we we tend to look at how people work with AI um but maybe we can show the audience um some of the stuff we've been building um I think it would be really fun you know we we talk a lot about different tools people can use but one of the things I just have never talked about it on this show is like the tools that we build um which have come out of problems that we've had um so it's yeah I think it's a good um I think it' be great to Great to demo it you want to you want to demo spiral yeah let's do it um so um okay so yeah this is spiral uh and uh I'm looking right now at our team spiral so these are like the spirals that our team has made and shared with each other um and so this is the point of the Spiral is to turn a podcast transcript so like literally a raw transcript into a tweet which you've used this successfully I use it every week yeah yeah so like I mean we've created some like pretty serious um uh viral tweets I just know that I I've like tested it with this before so I know that I just have this like like this this Google doc uh with a pretty good transcript and this is the episode that I did uh with Kevin Roose in the New York Times on um AI friends and and so this is a this is a workflow that I do every week is I I take a transcript and I paste it in there like that yeah literally just copy and pasted the entire thing um and now we're going to run it so it's going to take a second now to like basically take this super prompt that we've built um with the input the output and a bunch of examples that we've trained the spiral on send it to Claude and it just returned the output which is a tweet so um Kevin might be the first person to have 18 AI friends he's a columnist of the New York Times host the hard Fork podcast and author of future proof which by the way I don't one thing that's really cool about spiral is like this actually may not be in the transcript but it uses Claude and it actually knows who Kevin Roose is and like can pull in that information um yeah his experience was both compelling and and repelling uh he created AI friends for parenting advice outfit checks and was even and even tea time gossip we dive into I mean this is just like it's just really really concise it's compelling it like captures your attention and it's tight and yeah I mean the thing is like this is also how I write my tweets for my podcast like it is it is sounds exactly like you and it's the format that I use and that this is sort of like how it came about too is like I every week have to do a tweet and the Tweet is like to some degree it's like the most important part of the podcast because it's like the thing that more most people are going to see it's how I get distribution and that process is like really um it's really boring uh but it also requires a lot of skill even though it's repetitive and sometime in like may I realized that Claude was like good enough at writing to to actually do this for me um but the the prompt was like super long and like you know just hard for me to do and I knew no one else was going to do it um but I thought it could be really like helpful for like not just me but like anyone on the team cuz well a lot of what you do as a media business is like and businesses in general do this is like you're taking uh creative work or some sort of work in one form and you're like translating into another form so like we do this as a media company but like lots of uh lots of companies um like a B2B SAS company might take a webinar and turn it into like a LinkedIn post and that is another thing requires has a lot of skill but it's repetitive um and so I realized Claude could do this and it was actually on what we mentioned earlier on on a think week uh which is a every quarter we take a think week we don't do like our regular meetings we don't like um you know we don't publish new articles and it's just like a time to like let our brains like Run free and sort of reflect on the last quarter and plan for the next quarter and I just in in two days I just like went into a fug State and like was coding with Claude and like built like the the first simple version of this where it was like you could build a spiral and sort of train it on your own uh for me it was like training on exam previous examples of my own writing and it like worked after two days and we were looking at it and just like using it internally and the the writers on our team liked it and we were like wow that could be like that could be cool that could be a product um yeah and I think that this is actually a really good time to like shout out the that you wrote about Excel cuz like you basically did the same exact thing but like instead of excel it was clawed and it was like this thing that you kept using Cloud for and you can I mean this is what the definition of an AI rapper is it's like it's just we're going to add all of this functionality on top of something that you could probably use cloud for but you just won't um and there's so many opportunities like that I mean we have another one it's Sparkle it's like basically the same thing uh you know that same concept um so like how long do you think it would take you to write this an hour because but what I'd have to do is like I'd have to rewatch the whole podcast and load it into my brain and take notes and then once I had that then I could go write the Tweet so it would take an hour yeah versus what I don't know that was like five seconds um and to and to sort of like um explain a little bit more the the point you just made about the article I wrote like the thing that that I've been seeing and that I think we're we're kind of keying on for a lot of the products we we build is like um Exel is this really general purpose tool that um taught a lot of the world how to use computers it was like the first killer app for computers is the reason why business people started taking computers seriously and it's this general purpose tool that um it's really simple to start anyone can just type into a into a cell but it's like you it you can do enormously complex things with it so you can it's but it's sort of like its complexity and its power is like progressively revealed as you get deeper and deeper into it and um it started off being a tool for like you know obviously like doing financial planning basically or forecasts or whatever for businesses and over time because it's so General it just got adopted by lots and lots of different businesses to do lots and lots of different things that it was never maybe really intended for uh like people were using it as a CRM or a to-do list or like keeping track of like business processes and like all this kind of stuff um and I think Excel like really created the um the sort of B2B SAS wave because once people were trained on using Excel as a tool and and the idea that they could use computers to do all these tasks they created workflows inside of excel that were like really custom for their like specific um specific uh use case that XL just like wasn't that good at covering and and I'm not the first person to say this like this is uh I'm taking this from this guy Tom tungus who's a uh I think he used to be an investor at Red point and I think he's at another fund now but he's super super smart really great writer and um so Exel Progressive got unbundled over the next 20 years uh into all these different SAS products um and it's still around obviously xl's super you know a super important tool that is one of the most widely used pieces of software ever um but it also got fragmented and all these other purpose specific tools and I think chat gbt and Claud are the same basically like and and the same for a new generation of computer users um they're uh incredibly powerful tools that's really easy to get started they're incredibly um uh uh general purpose and I think um they are training people to try to learn what AI is useful for and how to use it um and as those people get more and more used to it they will find more and more problems that are would be better solved by a general by by a specific tool rather than a general purpose tool and I think spiral is a really good example of that where um I think spiral only works as a product because people are used to using AI enough or the people who use it are used to using AI enough they realize that yeah I can like prompt Claude to do this but like it's a pain in the ass um and and so they immediately sort of recognize like oh having a purpose specific tool for this is really good and there's this like expanding Horizon of people who are starting to get used to AI enough that they want a tool for something like this um I actually I actually Wonder so I have a bit of a different take and I wonder if it actually unlocks the power of AI for all of these people that actually wouldn't go to Claude to do that because now they have like one of the problems with Claude and Chad is like it's like the way that you interact with it is it is literally just like a chat function and it's sort of that same issue that we described earlier which is if you're not in a box you don't really know how to use the thing or like how to be creative and like that is the definition of like not in a box you could like do literally anything with it so I almost wonder like it's this purpose-driven thing that's supposed to do really one thing for you and does that make it more accessible to all the people that actually wouldn't go to uh and maybe that's not the case right now like maybe a lot of our early users are fans of every so they are using AI anyway but I I actually think that it's the um it's sort of the unlock for all of those people that don't use AI to start using it I think you're totally right in the sense that um it is um it's it's easy enough to use that people who don't use AI can use it and and will get a lot of value out of it but I think that those people are typically not searching for this tool because they don't know it's even possible or that it exists and I think the people who are like looking for this as a solution are the people who know it's possible but know it's hard and those are people who have already adopted these tools but like are not um uh who who who have already adopted these tools but are not satisfied with the quality level that they're getting or the ease of use that they're getting or the power they're getting from the general purpose tools and I think those people become the early adopters of products like this and then yes once they've adopted it then they can spread it to their colleagues for example who like would never even like think to search for something like this and maybe their colleagues skip from like they don't even have a phase where they're using CLA they're just using something like this and maybe this is the Gateway for them to be like whoa maybe I should use CLA because like I could use it for lots of other things too in addition to this specific thing so I agree I think it's a little bit more complicated than that but the the um the early adopters are the people who like know that there's a problem because they've been using Claud for this and they're like I think there's something better to be had here um I think that's right and I think you definitely actually see that with sparkle because so sparkle is a product that uh we launched yesterday it cleans your computer for you or organizes your computer for you and I think that um what we're describing right now is definitely the case for that because you know the sort of the the um the risk that you take with signing up for spiral is that you've just created a new account for something and like that's very low risk the risk for Sparkle is that you're allowing AI to organize your computer like means moving files around and that scary and um I think you can actually see that like we both thought Sparkle was going to be like a bigger launch than spiral turned out to be a smaller launch than spiral but I don't think that we realize just like how invasive actually of a product it really is it's not actually because like it can't delete your files it's super easy to undo it uh but uh mentally like that's very real yeah well let's see your desktop here's my desktop that's pretty clean man it's pretty clean doesn't it feel like a breath of fresh air every time I look at it and that's that's Sparkle so like show us um show us go go back to your desktop for a sec like show us the the organization scheme that you have you have all right so I've got recents um which is you know obviously a lot of screenshots and some data so anything that um I downloaded or anything that I added to my desktop today uh gets put into recents and it stays here for 3 days so any file that you like recently add to a a file a folder stays there for three days uh stays in recents um the manual library is like this place that you can use to if you don't want Sparkle to organize your computer organize these folders so if I'm like my taxes are really important and I do a good job of organizing them I'm going to create a folder in the manual library and then just organize uh my taxes manually and uh the other thing that sparkle does is if you already have a bunch of folders on your computer we'll automatically put them in manual Library so we don't we don't mess with those um and then AI library is like this magical place where I have had thousands of files on my desktop and now they're just magically organized um in my AI Library so I've you know been dog fooding uh uh Sparkle for months and I've had countless experiences of needing to find something that's like really obscure opening up my AI library and uh being able to find it super quickly um so I mean it's pretty sick it's definitely I mean I find it super effective for desktop and especially for downloads um yeah it's pretty amazing it's great um and yeah I'm one of those people where it's just like that everything's a mess for me and um that's one of the things I've been so I mean that's why one of the reasons I got into productivity originally is like I'm just like bad at organizing stuff and so that's why I started to Super organizers because I was like I want to learn how to like do this you know it's like sometimes you turn your like weakest trait into like a skill or like a thing that you're obsessed with because it's you're bad at it um and I actually like I built the first version of of Sparkle like four years ago um for that for that purpose but it was all manual um and uh and I used Thiago fores he has this system called parah I use parah to like as the as the base organizational system which by the way he uses Sparkle now which I feel like is the ultimate vote of confidence like he is the he is the organization guy and now he uses Sparkle to organize he he at least tweeted it I'm not sure I'm not sure whether he us it he might or might not but uh he at least he's a spar we say that that's true yeah yeah um and um and uh when all the AI stuff started happening I was kind of like well maybe it would be cool to um like just redo it with with AI organization and that was the first project we decided to work on together um and you sort of took it and ran with it and I mean it's it's it's I think I think you guys it rebuilt it from the from the ground up you you've been working with jav one of the developers we work with and I mean it's such a it's such a it's one of those products where um once you install it you don't have to think about it ever again but you feel it every day that when you use your computer and I I love that it's such a good feeling yeah I mean that that is a special type of product that you don't actually need to engage with it for it to deliver value to you and that is like I think something that we will continue to try to search for and products that we build so this has been an incredible episode I'm so glad that we did this um we're we're we're getting close to time but um I think we'll definitely keep doing this regularly um we want to keep people updated on what we're building and how we're doing we're kind of like discovering a new model as we go and and so you'll you'll definitely be back and thanks so much for coming on like this is honestly this is so much fun I feel very very lucky to get to get to do this with you yeah likewise it's bring bring me back to my uh my radio days of college you're good at it man I can tell you're you're a radio guy yeah yeah thank you for having me here this is cool of course all right see you see you oh my gosh folks you absolutely positively have to smash that like button and subscribe to Ai and I why because this show is the epitome of Awesomeness it's like finding a treasure chest in your backyard but instead of gold it's filled with pure unadulterated knowledge bombs about chat GPT every episode is a roller coaster of emotions insights and laughter that will leave you on the edge of your seat craving for more it's not just a show it's a journey into the future with Dan shipper as the captain of the spaceship so do yourself a favor hit like smash subscribe and strap in for the ride of your life and now without any further Ado let me just say Dan I'm absolutely hopelessly in love with you