Nov 3, 2022 · 1h 28m · my-first-million
Kevin Rose: His $100M/Year Watch Blog, Money From Digg.com, & Web3 Business (#382)
Kevin Rose · 51m spoken Shaan Puri · 16m spoken Sam Parr · 12m spoken HubSpot Ad Customer · 10s spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Tech entrepreneur and investor Kevin Rose joins Sam Parr and Sean Puri on the My First Million podcast to discuss his prolific entrepreneurial journey, from building Digg and angel investing in Twitter to scaling Hodinkee into a $100M luxury brand and pioneering Web3 ventures. Throughout the conversation, Rose shares hard-won insights on startup incubation, mental well-being, emerging technologies like AI, and his pragmatic approach to personal finance.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The hosts hold 36% of the talking time here. How this is scored →
The hosts as informed peer 4.6 Guest teaching 4.9 Guest disagreement 1.6 The hosts pushing back 2.3
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 58:46 Rejecting Dogmatic Decentralization Maximalism
Kevin meets Sam's critique head-on by disavowing dogmatic Web3 maximalists, arguing that forcing total decentralization where it provides no structural advantage is absurd.
Hardest push from the hosts ▶ 57:45 Calling Out Web3 Circular LogicSam forcefully pushes back against the Web3 movement, calling it an insular circle jerk that pushes unnecessary decentralization and ignores functioning Web2 solutions.
Biggest teaching moment ▶ 1:12:38 Physical Asset Provenance and Vaulted RedemptionKevin provides a masterclass on non-speculative NFT utility by walking through how high-end wine provenance eliminates secondary market fraud and storage degradation.
The host holds their own ▶ 1:19:04 Bitcoin's Failed Inflation Hedge TestShaan presses Kevin on Bitcoin's 50 percent drop during record macroeconomic inflation, challenging the primary narrative promoted by crypto advocates.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| A Lifetime of Tinkering and Entrepreneurial Philosophy | 5 | 3 | 1 | 1 | Sam opens by rattling off Kevin's extensive resume across Digg, Hodinkee, Zero, and Oak. Kevin clarifies that his newest venture is Proof, framing his career path around playful tinkering rather than a grand calculated master plan. | |
| Early Exits and Angel Investing in Twitter | 4 | 5 | 1 | 2 | Kevin details how selling secondary stock during Digg's peak gave him the capital to write early angel checks into Twitter and Facebook. He explains how secondary share sales functioned and shares an anecdote about Gary Vaynerchuk paying a higher price for Twitter shares. | |
| Early Conviction in Social Graphs and Square's Seed Round | 4 | 5 | 1 | 1 | Kevin recounts his thesis behind investing in Twitter, contrasting its asymmetric follow model with bidirectional social networks like MySpace and Friendster. He also explains how recording a viral demo video secured his spot in Square's oversubscribed seed round. | |
| Meeting Young Mark Zuckerberg and the Power of Saying No | 5 | 4 | 2 | 1 | Kevin shares his impressions of meeting a 21-year-old Mark Zuckerberg, highlighting Zuckerberg's willingness to ask basic questions without insecurity. Shaan connects this to Jason Citron at Discord rejecting expansion features, emphasizing the discipline of saying no. | |
| Frameworks for Starting and Killing Projects: Zero and Tiny | 4 | 4 | 1 | 2 | Sam asks whether Kevin employs rigid funding rules like Kevin Ryan or Atomic Labs when spinning up projects. Kevin explains his criteria for putting apps like Zero into maintenance mode versus shutting down brief fad experiments like Tiny. | |
| Finding Fun in Startups and the Web3 Blue Ocean | 3 | 4 | 1 | 1 | Shaan asks which chapter of Kevin's career was most enjoyable. Kevin admits that traditional startups are grinding operational rollercoasters and explains why the open blue ocean of Web3 and digital art provides genuine creative fun. | |
| Merging Watchville with Hodinkee to Build a $100M Brand | 5 | 6 | 1 | 2 | Kevin describes merging his aggregation app Watchville with Hodinkee and scaling e-commerce past $100M in revenue. He breaks down their editorial hiring strategy, noting that teaching horology experts how to write cleanly with editors is far easier than teaching professional writers watch mechanics. | |
| Sponsor Message: HubSpot CRM Platform | 3 | 4 | 2 | 2 | After a brief HubSpot sponsor spot, Shaan asks Kevin what triggers his competitive fire or anger. Kevin reflects on moving past early career hustle anxiety and neighborhood controversies by prioritizing mindfulness and mental peace. | |
| Radical Ideas, Palmer Luckey, and Canine Longevity Trials | 5 | 5 | 2 | 2 | The hosts discuss Palmer Luckey's eccentric zero-calorie synthetic oil food experiments. Kevin explains his philanthropic involvement alongside Jack Dorsey in funding University of Washington canine rapamycin longevity trials. | |
| The Looming AI Revolution in Creative and Engineering Fields | 4 | 6 | 1 | 2 | Kevin forecasts the massive disruption generative AI will inflict on creative marketplaces like Fiverr, creative writing, and interface design via prompt-based tools in Figma. Sam and Shaan ask for concrete software use cases. | |
| Subcultures of the Web: The Shift to Private Discords | 4 | 4 | 1 | 2 | Sam asks what obscure online communities Kevin monitors. Kevin describes spending his time in private Discords, DAOs, and Telegram groups rather than public forums, prompting Sam to lament the loss of open web discovery. | |
| Debating Web3: Pragmatism Versus Decentralization Dogma | 6 | 6 | 3 | 6 | Sam directly challenges Web3 as an elitist, circular economy that invents problems while promoting dogmatic decentralization. Kevin agrees with the critique of dogmatic maximalists and provides a pragmatic counter-argument showing how hybrid models improve financial efficiency. | |
| Tangible NFT Utility: Wine Provenance and Interoperable Gaming | 6 | 7 | 3 | 5 | Shaan challenges Kevin to present practical NFT utilities beyond digital art. Kevin illustrates high-end wine provenance and cellar storage redemption, while Shaan steel-mans interoperable gaming skins before agreeing with Kevin's core thesis. | |
| Bitcoin Macro Dynamics and Personal Asset Allocation | 6 | 5 | 2 | 3 | Shaan confronts Kevin with the failure of Bitcoin to act as an inflation hedge during high macro inflation. Kevin breaks down his pragmatic personal asset allocation, revealing that 90% of his liquid portfolio is anchored in conservative Vanguard index funds and short-term Treasuries. |
Statements from this episode (27)
Kevin Rose: 90% of his 10 to 15 ventures went to zero
“I've done that a handful of times. You know, probably at least 10 to 15 businesses of which, you know, 90% of them go to zero, and then there's a few that pop and become, you know, pretty big.”
Rose: Digg reached around 38M monthly users at its peak in 2006
“When I was in the middle of web two point O, which was the, when dig was at its peak, which was about a 2000, early 2006. You know, we were hitting around thirty eight million people a month using the site.”
Rose: Watch blog Hodinkee generates over $100M in annual revenue
“It's over a hundred million revenue a year now, which is nuts.”
Rose: Revision3 sold to Discovery Channel for $35M
“Revision three where I was the co-founder is a media company that became Discovery Channel's digital arm, and we sold that for a thirty five million dollars back in 2008 or something like that.”
Rose: Selling Digg secondary shares funded early Twitter and Facebook checks
“I sold a little bit of my dig stock enough to give me the ammo to go and do small C checks, you know, and put, you know, 25 K into, you know, Twitter's seed round and put, you know, 25 K and, or it was more into Facebook, but they're a little bit later stage.”
Rose: Viral prototype demo video secured allocation in Square's seed round
“Cause I hit Jack up and I was like, Hey, I heard you're doing this new credit card thing. I'd like to be an angel investor. And he's like, Oh dude, it's oversubscribed. I'm sorry. Like we've closed the round, like blah, blah. And I was like, damn it. I'm like,…”
Rose: Zero grew from tens of thousands to over 1M MAUs
“When I launched Xero, it sat at, you know, tens of thousands of users for the first eight months, and then fasting hit, and it became more of a household thing, and people were talking about intermittent fasting, it was all over TV, and different, you know, pl…”
Rose: Tiiny hit hundreds of thousands of downloads before collapsing
“We launched, and it just, it caught fire immediately, and we had, you know, hundreds of thousands of downloads in the first week, and then it just died off completely, and everyone was like, ah, that was a fad. That was a fun little fad, and that one we shut d…”
Kevin Rose: Crypto and NFTs are more fun because of blue ocean opportunities
“When I've kind of gotten into the art and NFT side of Things. That world and the world of cryptocurrency is probably the most fun because it is so blue ocean and there's just so much to be built there. It's not building yet another app and competing on, on CAC…”
Parr: The Hustle bootstrapped and sold for tens of millions
“Basically I started this company called the hustle. It was like a daily email and we sold it for, we bootstrapped and sold it for tens of millions of dollars.”
Rose: New luxury watch market exceeds ten billion dollars annually
“New, new, new luxury watches are double digit billions of dollars in a year in, in terms of market size.”
Rose: Hire technical domain obsessives and teach them to write
“The best way to do that was to find people that had the natural, organic, built-in, a love for horology. Like, just this, like, for all things mechanical watches. So, you know, we would have writers that if you take, for example, like, the Speedmaster, the wat…”
Rose: My controversial San Francisco house demolition was due to asbestos
“The historical building thing was definitely not true. That, that, that was a pretty funny one in that but that was that was just people wanting to keep an old house up in the neighborhood, and they called it historical, even though it really wasn't. We wanted…”
Rose, Jack Dorsey, and Brian Armstrong are funding dog longevity trials
“Myself and Jack Dorsey and Brian from Coinbase and a few others all have been putting money into funding studies at the University of Washington to really prove this out in dogs and canines, and then eventually move it into human trials.”
Rose predicts generative AI will make Fiverr completely non-existent
“Whether it be creative writing or I believe Fiverr as a company, it will just be non-existent. It's going to destroy the low end of the creative market initially and then work its way up the chain.”
Rose: AI will write 90% of a New York Times bestseller by 2027
“I have no doubt in the next five years we'll see a New York Times bestseller that was 90% written by AI.”
Rose: AI will perform 90% of Figma interface design work by 2025
“But this is like inning one, like two, three years from now, it'll be doing 90% of the work versus, you know, the first right now was probably 20% of the work.”
Parr: Web3 is a circular economy that rarely beats Web 2.0 solutions
“My opinion on the web three is basically, it's a bunch of like, it's just this kind of circular economy of a bunch of people making, making products to serve an industry that has yet to like truly figure out, or I don't know what you call an industry, a moveme…”
Rose: Uses safe deposit boxes to safeguard personal crypto keys
“I'm not in that camp. I do that personally and use safety deposit box and a whole slew of things to safeguard that for some things. But there's other solutions where, where a hybrid approach makes more sense.”
Rose: Rolex manufactures over 1 million watches annually but conceals the number
“Something you may not know about Rolex is they make over a million Rolexes per year. And so Rolex hides that number.”
Rose: Over 90% of long-term NFT users will not know they are using NFTs
“90 plus percent of people that interact with NFTs over the long term, I believe won't even know it as they're doing it as an NFT.”
Rose: Partnering with winery to launch physical bottle-backed NFTs in four months
“I'm working with A well-known, like very culty kind of wine producer out there... So one thing that is happening in the next Four months will be the issuance of NFTs to people that is going to be from a major well-known winery where it will represent one physi…”
Kevin Rose: Blockchain data persistence prevents loyalty program loss if startups fail
“The beautiful thing about it being decentralized, and this is one argument for decentralization, is that it's forever on the chain and you're not dependent upon a company being around for that to exist.
So if an artist is engaged with a startup,
That is workin…”
Shaan Puri: Secondary resale markets will increase gaming spending
“And the other one is that if I'm just done with the game, I could just dump it onto the next person who's really interested in Fortnite and I can recoup some of my investment, which will make more people want to spend in games because it's not just a money pit…”
Rose keeps the majority of his liquid portfolio in Vanguard index funds
“The majority of my, you know, personal holdings is, is still standard, you know, index funds that, that are pretty vanilla, the low cost index funds, you know, the Vanguard way”