By playing, you agree to uListen's Terms and Privacy Policy and YouTube's Terms of Service.
My First MillionKevin Rose: His $100M/Year Watch Blog, Money From Digg.com, & Web3 Business (#382)
Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.
CHAPTERS
- 0:00 – 5:16
Kevin Rose's Many Projects and the Common Thread
Sam Parr recaps Kevin Rose's resume, from Digg and Hodinkee to Zero, Oak and the newer Proof NFT venture. Rose says the thread running through it all is tinkering and building things he thinks should exist, knowing most of them go to zero.
- •Resume covers Digg, Hodinkee, Zero fasting app, Oak meditation app, True Ventures and Proof
- •Proof is about 10 months old and is his NFT venture
- •Rose says the common thread is exploration and building what doesn't exist
- •He's started 10 to 15 businesses, about 90% of which went to zero
- 5:16 – 8:34
Most Lucrative Ventures: Angel Checks and the Revision3 Exit
Rose says investing has paid best, helped by friendships formed when Digg peaked. He explains how selling a little Digg stock funded small seed checks, and that his biggest company sale was Revision3 at $35 million.
- •Digg hit about 38 million monthly users in early 2006
- •Investors buying some founder stock gave him money for small seed checks
- •Revision3 became Discovery's digital arm and sold for $35 million
- •Hodinkee is over $100 million in annual revenue
- 8:34 – 13:29
Getting Into Twitter and Square Early
Rose tells how he bought Twitter stock from a departing engineer and how Gary Vaynerchuk ended up paying a higher price. He explains why Twitter's follow model convinced him it would be big, and how a prototype video got him into Square's seed round.
- •Bought Twitter stock from engineer Blake after asking Ev
- •Twitter's follow model removed the need for mutual friend requests
- •Texting a short code made it simple enough for non-technical people
- •Square's round was closed until an investor dropped out after his prototype video
- 13:29 – 19:25
Meeting Mark Zuckerberg and the Power of Saying No
Rose recalls meeting a 21-year-old Zuckerberg in 2005 and being struck by how mature and open he was. Shaan Puri compares this to a Discord CEO who turned down his pitch, and both agree focus means saying no.
- •Zuckerberg asked pointed questions about hiring and scaling
- •His advice was to surround yourself with smarter people and ask questions
- •Rose had hidden his vulnerabilities as a college dropout
- •Shaan describes Discord's CEO rejecting expansion ideas in favor of one focused utility
- 19:25 – 23:21
When to Kill or Wait on a Project: Zero and Tiny
Asked about rules for starting projects, Rose says he has no fixed timeline. The fasting app Zero sat at tens of thousands of users for eight months before exploding, while the photo app Tiny went viral and died, which he saw as a feature rather than a product.
- •Sam cites other founders' rules like six months and $300K
- •Zero stayed in maintenance mode until fasting went mainstream
- •It later reached a million-plus monthly active users
- •Tiny got hundreds of thousands of downloads in a week then faded
- 23:21 – 26:12
The Most Fun Work: Blue Ocean NFTs and Crypto
Shaan asks which chapter of Rose's career was the most fun. Rose says he never starts things to make money but out of creative pull, and that NFTs and crypto are the most fun lately because the space is so open.
- •No startup is fun all the time; all are roller coasters
- •He builds what he's drawn to rather than chasing profitable niches
- •NFTs and crypto are blue ocean compared to competing on app-store CAC
- 26:12 – 32:33
From Watchville to Hodinkee: Building a $100M Watch Business
Rose explains his personal tie to watches through his father's Rolex and how his aggregator app Watchville merged with Ben Clymer's Hodinkee. They grew it from $1.5–2 million to over $100 million in revenue by adding e-commerce and partnering with watch brands.
- •Watchville aggregated watch content for mobile readers
- •He merged with Hodinkee, moved to New York and became CEO
- •Revenue went from about $1.5–2 million to over $100 million
- •An Apple contact described a $250,000 Apple Pay watch purchase as the largest known at the time
- 32:33 – 36:07
Trust, Curation and Hiring Writers
Rose says the Hodinkee playbook is curation with a point of view, which he is now applying to NFTs at Proof. Editorial depth built trust, which made high-priced commerce possible, and he preferred hiring passionate experts and adding an editorial layer.
- •Proof applies the Hodinkee curation playbook to NFTs
- •Technical, serious writing built reader trust
- •Trust lets readers make $20,000–$50,000 purchases
- •He hired people with deep watch knowledge and had copy editors polish their drafts
- 36:07 – 44:10
What Fuels Rose: Creative Ideas, Rage and Taming the Mind
Rose says new ideas and creative, world-changing entrepreneurs energize him most. Prompted by the hosts' mentions of past controversies, he describes spending recent years trying to master his own mind, citing meditation and his constant-thinking tendency.
- •He's drawn to entrepreneurs flipping whole verticals on their head
- •He says the hosts' raccoon and historic-house controversies each had their own story
- •The old 24/7 hustle mindset created anxiety
- •Making the meditation app was partly a forcing function for his own peace of mind
- 44:10 – 48:21
Longevity Research and Funding Rapamycin Studies in Dogs
After a tangent about Palmer Luckey, Rose describes his interest in longevity. He and others fund a University of Washington study of rapamycin in dogs, with no financial payoff, and he gave his own dog the treatment.
- •Rose, Jack Dorsey, Brian from Coinbase and others fund the study
- •About another million dollars was added to power it to detect up to a 10% lifespan increase
- •There is no direct financial return, just furthering science
- •His 12-year-old dog still runs like a pup, which he partly attributes to the treatment
- 48:21 – 57:05
AI as the Next Big Wave and Where Geeks Gather Online
Rose says AI will change everything within five years, starting with the low end of creative work, and points to prompt-based design tools in Figma. He then explains that conversation has moved to private Discords and Telegram groups.
- •He predicts AI will upend the low-end creative market and Fiverr
- •Figma plugins already generate interface drafts from prompts in seconds
- •Engineering talent flowing into AI is a signal he pays attention to
- •He follows crypto Twitter and private Discords, Telegrams and DAOs
- 57:05 – 1:03:29
Sam's Web3 Skepticism and Rose's Response
Sam argues Web3 is a circular economy that is dogmatic about decentralization. Rose agrees that decentralizing for its own sake is silly, warns against maximalism, and describes hybrid approaches such as Coinbase.
- •Sam says adding Web3 to something doesn't mean there's a real problem
- •Rose agrees with critiques of maximalists, including Bitcoin-only views
- •Web2 logins are fine for low-value token-gated content
- •Hybrid models like Coinbase pair decentralized assets with centralized support
- 1:03:29 – 1:21:07
NFT Use Cases and the Bitcoin Inflation Debate
Shaan plays devil's advocate on NFT use cases, and Rose lays out art, loyalty and access, wine-bottle tokens and portable game items. Shaan then challenges him on Bitcoin's drop despite inflation, and Rose answers with its volatility and its role as a small portfolio slice.
- •Rose says art is the easy NFT use case, thanks to provenance, scarcity and programmability
- •He expects most people to use NFT-backed tickets and rewards without knowing it
- •A planned winery NFT would represent one stored bottle and cut fraud
- •Shaan's Fortnite example shows portable, resellable game items
- •Rose says Bitcoin's spikes hurt it and he dislikes that it isn't green
- 1:21:07 – 1:28:06
Rose's Personal Portfolio and Wrap-Up
Rose says his liquid money is about 80% Vanguard index funds and 20% bonds, with venture risk held through True Ventures. He covers T-bills, I bonds, crypto at roughly 10%, and owning his home, then the episode closes with praise for Tim Ferriss's influence.
- •80% index funds and 20% bonds outside his venture exposure
- •Partners at True Ventures invest their own money alongside the fund
- •Crypto is about 10% of his overall pie, split between NFTs and digital assets
- •He owns his home and favors borrowing against it when rates are low
- •Hosts say the Kevin and Tim shows were a blueprint for their podcast
