Sep 28, 2023 · 1h 9m · my-first-million
How Jason Yanowitz Bootstrapped Blockworks To A +$20M/yr Company
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode, host Sam Parr interviews Blockworks co-founder Jason Yanowitz about bootstrapping a profitable crypto media and analytics business to over $20 million in annual revenue. Jason shares his journey from early sales hustles to building flagship conferences, launching an institutional data terminal, and navigating startup psychology.
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 38.2% of the talking time here. How this is scored →
The hosts as informed peer 5.3 Guest teaching 4.2 Guest disagreement 2.4 The hosts pushing back 3.3
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 58:45 Nobody ever got wealthy through diversification
Jason flatly rejects Sam's conservative portfolio advice, arguing that true wealth is never built through diversified holdings.
Hardest push from the hosts ▶ 45:57 That's a shit businessSam bluntly interrupts Jason's ticketing software idea, citing Eventbrite and Splash to argue that ticketing platforms have terrible unit economics and low take-rates.
Biggest teaching moment ▶ 51:25 Protocols are real operating businessesJason walks Sam through how DeFi protocols like MakerDAO generate $100M in revenue and why institutional investors require governance analytics rather than simple news.
The host holds their own ▶ 1:02:35 Historical empire decline and index resilienceSam counters Jason's societal collapse theory by citing historical data on post-peak empires like Great Britain and long-term emerging market compound annual returns.
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 |
|---|---|---|---|---|---|---|
| The Genesis and Financial Scale of Blockworks | 4 | 3 | 1 | 2 | Sam establishes rapport by bringing up specific research on Blockworks' estimated $25M revenue and EBITDA figures. Jason confirms they exceeded goals while explaining their bootstrapped history and the split between ad slowdowns and subscription growth. | |
| Bootstrapping Through Hustle, Cold Outreach, and Podcasts | 5 | 4 | 2 | 2 | Sam compares Jason's path to his own experience launching The Hustle. Jason outlines his thesis on why creator-led media companies fail when they prioritize content over monetization. | |
| The Blueprint and Economics of Massive Live Conferences | 6 | 6 | 2 | 2 | Sam references Sheldon Adelson and Comdex to describe conferences as temporary real estate marketplaces. Jason extends the analysis, explaining why boutique events have poor business models and detailing the extreme financial risks of multi-year venue bookings in cyclical industries. | |
| Jason's Early Hustles: From eBay Cards to College MLM | 4 | 3 | 1 | 3 | Sam presses Jason to tell the full story of his college energy drink hustle. Jason candidly details building a 4,600-person downline and earning a BMW before realizing through Bill Ackman's Herbalife presentation that he was running an MLM. | |
| The Sam Ovens Influence and the Accidental Ethereum Pivot | 4 | 2 | 1 | 3 | Jason recounts how seeing Sam Ovens ads and attending a seminar led him to launch an Ethereum consulting business hours after learning what Ethereum was. Sam playfully teases him about falling for internet marketing schemes. | |
| Mid-Roll Break: Copy That Program and HubSpot CRM | 6 | 2 | 2 | 3 | Following the mid-roll ad read, Jason flips the dynamic by questioning Sam on his personal optimization drivers. Sam delivers an in-depth breakdown of pursuing fulfillment, avoiding obligatory tasks, and resisting the urge to build massive enterprises. | |
| Untapped Business Ideas: Event Software and Hair Transplants | 7 | 5 | 6 | 7 | Jason suggests building a Beehiiv-style platform for conferences, but Sam forcefully dismisses it as a poor business by citing Eventbrite and Splash's low take-rates. Jason counters by pointing to enterprise SaaS models like Bizabo and pitches the hair transplant market. | |
| The Mechanics and Vision of Blockworks Research | 5 | 7 | 2 | 2 | Jason educates Sam on the architecture of Blockworks Research, explaining how protocols like MakerDAO function as revenue-generating businesses and how they scrape decentralized governance forums. Sam admits unfamiliarity with traditional sell-side research terms. | |
| Personal Portfolio Allocation and Historical Macro Cycles | 7 | 6 | 5 | 6 | Sam challenges Jason's 100% liquid crypto allocation using portfolio theory and a barbell strategy. Jason counters with Peter Turchin's elite overproduction theory, while Sam pushes back using 30-year emerging market historical ETF data and empire decline precedents. |
Statements from this episode (21)
Yanowitz: Blockworks raised $12M at $135M valuation after exceeding $20M revenue
“Last year we had a goal of
twenty million in revenue, and we pretty decently exceeded that.
and we've been profitable since day one.
So, yeah, we bootstrapped the business for the first five and a half years, and then back in April or May, we took we raised …”
Parr: Low barrier to entry causes most media creators to execute poorly
“Media is an interesting business because the barrier to entry is really low, particularly for the written word.
Well, even for podcasts, everyone can write.
Therefore everyone, the pool of people who think they're good writers is significantly higher than like…”
Parr: Blockworks has a crystal clear path to $100M in sales
“Whenever, like, you're telling me about your guys' business, I'm like, oh, I see a, well, from an outside, I see a crystal clear path to, like, a hundred million in sales.”
Yanowitz: Most media companies fail because creators cannot sell
“I would argue though, like the problem with most media companies and the reason they don't work is because they're started by folks who can't monetize. So they're usually started by a podcast host or a newsletter writer in 20, 23, and they're brilliant at cont…”
Yanowitz: Blockworks lost 80% of revenue overnight when COVID hit
“Then COVID hit, and 80% of our revenue got wiped out overnight because we were, 80% of revenue came from events”
Yanowitz: Blockworks generated over $10M from Permissionless conference in 2022
“Last year we did, like, well over ten million from permissionless.”
Yanowitz: Small events have bad business models; profitability requires massive scale
“The thing that a lot of entrepreneurs get wrong with events is the business model of small events is a really good experience for attendees. It's really fun. You bring people together, good community building. It is a shit business model. So the kind of secret…”
Yanowitz: CoinDesk event attendance fell 80% in 2019, nearly destroying the company
“CoinDesk almost died in 2019 because of that reason. They had like, I don't know, 10,000 plus people in 2018. And then in 2019, they fell to like 2000 people, right? They fell 80% and that almost wiped out their whole business.”
Yanowitz: Half of all conference tickets sell within four weeks of the event
“50% of tickets get sold in the four weeks leading up to a conference.”
Yanowitz: Built 4,600-Person MLM Downline In College
“Ended up having 4600 people in my downline had like a thousand people in France.”
Sam Parr: Jason Yanowitz will be worth $100M+ liquid by 2028
“You're gonna be worth at least a hundred million dollars in the next five years, I would imagine. Liquid. That, that's my prediction.”
Yanowitz: First-time founders almost never start with a grand vision
“Everybody thinks that founders had this vision from day one. But if you talk to founders who have built big companies, 99% of them do not. They do, they never did at the beginning. Second-time founders actually do, I've noticed. Like, second-time founders will…”
Yanowitz: Startups never get easier because founders constantly optimize for max pain
“This idea that it gets easier as you grow, right? That's I think anyone startups are like this weird or being a founder is this weird thing where like, I think what they, you kind of hold constant, the rate at which you can tolerate problems and Everything els…”
Yanowitz: Starting a business offers more safety and security than employment
“I actually think there's more Safety and security and doing something that you own and where you can like manage a hundred percent of the risk. Like you can be the best employee somewhere. And if all hell breaks loose and like the company's doesn't have a good…”
Yanowitz: Bizabo dominates enterprise events despite a terrible product
“It's an enterprise events platform. It's like, it's, they sell it like SaaS. It's like 20 K a year, 30 K a year subscription. You host all your platform, your events on them. They don't take a cut of the fee, of the ticket sales. I don't think it's just a, but…”
Yanowitz: MakerDAO will generate $100M in revenue in 2023
“So MakerDAO, for example. They'll do a hundred million of revenue this year.”
Yanowitz kept 100% of his liquid portfolio in crypto until recently
“Of my liquid portfolio, I'm, until very recently, I was a hundred percent in crypto.”
Yanowitz: No single person ever got wealthy through diversification
“No single person ever got wealthy through diversification.”
Yanowitz: The best way for Bitcoin to really work is US collapse
“The best way for Bitcoin to really work is for the U S to collapse.”
Sam Parr: 90% of Web3 and NFTs are 'total bullshit' and scams
“I think that 90% of the rest of the stuff is a complete scam. I think NFTs are, for the most part, total bullshit. I think Web Three, for the most part, is total bullshit. And I think that the people who entered into that space oftentimes are horrible entrepre…”