🍿 Blockworks: Raising the Stakes (Part II)

CHAPTER 6
The Money, Raised, Eyes, Strained.

By early 2023, Blockworks had reached a crossroads. For six years, Jason and Mike had bootstrapped their way to success, reinvesting profits from their media business to fuel growth. But the landscape was changing. Crypto was in the depths of a bear market, and competitors were faltering under the weight of over-expansion and unsustainable business models. Blockworks had weathered the storm better than most, but Jason and Mike saw an opportunity to do more.

“Everything was falling apart,” Jason would later reflect. “We had left growth on the table during the bull market so we could remain solid in the bear market. But we knew if we wanted to accelerate, we needed capital.”

Their decision wasn’t taken lightly. Raising money meant making promises—to investors, to their team, and to themselves. It was a commitment to scaling the business in ways that bootstrapping simply couldn’t sustain.

On a particularly gray February afternoon in 2023, Jason sat at his desk, laptop open, preparing for yet another fundraising call. He adjusted his camera, ensuring everything looked professional. The call started smoothly enough. Jason outlined Blockworks’ vision, walking through their growth strategy and their plans for expansion. But then, mid-sentence, he felt it—the telltale signs of an oncoming cluster headache.

A sharp, searing pain began behind his right eye, radiating outward with a force that made his breath hitch. His vision blurred slightly, and his eyes started to water uncontrollably. Jason gripped the edge of the desk, willing himself to stay composed as he finished his point.

Mike glanced at him, his expression shifting from focus to concern. He could see Jason’s face beginning to droop on one side, the visible marker of what was coming.

Jason muted his mic and texted his wife, Dana: “I need the injection. Now.”

A moment later, Jason's wife Dana appeared silently at the door. She knelt beside him, just out of the camera’s view, syringe in hand. Jason kept his face turned toward the screen, forcing a smile as he nodded along to the investors’ questions. Dana worked quickly, injecting the medication into his thigh with practiced precision.

The pain began to ease, but Jason’s focus had already shifted to a new kind of challenge—finishing the call without betraying the ordeal he had just endured.

“Having her there saved me,” Jason would later admit. “It’s impossible to fight through that pain without help.”

After the call ended, Jason leaned back in his chair, the adrenaline of pushing through the meeting finally wearing off. His right eye still ached, and his face felt heavy from the residual effects of the headache. For Jason, this wasn’t an isolated incident; cluster headaches had been a part of his life for over a decade.

“They’re called suicide headaches for a reason,” Jason once explained. “It’s not that you want to end your life—it’s that the pain is so overwhelming, you’d do anything to make it stop.” Cluster periods could last weeks or even months, with two or three attacks per day. During these times, Jason relied on an arsenal of treatments: nerve blocker injections, oxygen tanks, and prescription medications. Yet even with these tools, the attacks were often debilitating.

“The worst period I ever had lasted three or four months,” Jason said. “It was like entering this state of extreme desperation. There’s no way to fight through the pain—you just have to endure it.”

And endure he did, even as he managed the high stakes of running a rapidly growing company. Jason’s ability to juggle the relentless demands of his work with the physical and emotional toll of cluster headaches was a testament to his resilience and the support of those around him. Despite moments like that, the fundraising process moved forward. Blockworks raised $12 million in May 2023 at a $135 million post-money valuation. But getting there required meticulous planning.

Their lead investor, Dan Tapiero of 10T (now 1RT), approached valuation with a structured approach. He divided Blockworks’ revenue into three buckets: conferences, digital media (podcasts and newsletters), and subscription-based research. Each bucket was assigned a different revenue multiple based on market norms.

“It was fascinating to see it laid out like that,” Jason said. “We realized $20 million in conference revenue might be equivalent to $2 million in subscription revenue in terms of valuation.”

The raise itself was highly targeted. Jason and Mike didn’t want a chaotic “party round” with dozens of investors. Instead, they chose three trusted groups: Santiago Santos, Jason’s Empire podcast co-host; Michael Anderson and Vance Spencer of Framework Ventures, Mike’s Bell Curve co-hosts; and Dan Tapiero, a long-time supporter who had been speaking at their events for years. 

“We wanted people we trusted,” Jason explained. “This wasn’t just about money—it was about having the right partners for the journey ahead.”

Taking external capital changed everything. “When you raise money, you immediately raise the stakes,” Jason said. “It’s a promise to someone else that you’re going to deliver a massive return on their investment.”

While Blockworks had always operated with discipline, the influx of capital brought new pressures. It also brought new opportunities, particularly with their Research & Data business.

For years, Jason and Mike had been frustrated by the quality of research and data platforms in crypto. “No one was doing it at an excellent level,” Jason said. “We just thought we could do it better.”

Their approach was methodical. Instead of building a standalone research platform, they integrated it with their media business. “Our podcasts, newsletters, and editorial site already brought in over a million unique readers each month,” Jason explained. “That’s our top-of-the-funnel. If even a small percentage of those readers move into the research platform, we’ve got a colossal business.”

Unlike their competitors, Blockworks didn’t need a sprawling sales team to drive subscriptions. Their media brand did the heavy lifting, funneling engaged, educated users directly into the research product. “We own the relationship with our audience,” Jason said. “That’s our superpower.”

The synergy between the media business and the research platform became the cornerstone of Blockworks’ strategy. Media generated cash flow, which was reinvested into the capital-intensive research and analytics side.

“It’s like building a SaaS product on top of a media company,” Jason said. “The two sides feed into each other perfectly.”

Their approach was sequential by design. “Other research companies started with data but didn’t prioritize media, so they don’t own the distribution we do,” Jason explained. “You need both to truly scale.”

By mid-2023, Blockworks had transformed into a hybrid powerhouse: part media company, part research platform, and entirely driven by a vision to reshape how crypto professionals consumed information.

But the journey was far from over. With new capital in hand and a clear strategy in place, Jason and Mike were ready to take Blockworks to the next level.

CHAPTER 7
The Blockworks of Today 

Blockworks wasn’t built by accident. By 2024, the company operated across four distinct but deeply interconnected business lines: Digital Media, Events, Research & Data, and a newly launched Advisory division. Together, these segments formed what Jason Yanowitz referred to as the Blockworks Flywheel—a system where each piece reinforced the others, creating a business that was far greater than the sum of its parts.

“None of these segments would work on their own,” Jason often explained. “But when you bring them together, you get something powerful. The media side builds trust and distribution. The events generate cash flow. The research and data bring enterprise value. It’s all designed to work in sync.”

At the core of this flywheel was Blockworks’ media business, which connected millions of people to the brand. Conferences fueled growth with cash flow that could be reinvested into high-value projects like Research & Data. Advisory services leveraged insights from the media and research arms to provide tailored guidance to clients. Everything fed into everything else.

The digital media business was the beating heart of Blockworks, providing a direct connection to their audience. Through podcasts, newsletters, and a robust news/editorial site, Blockworks reaches millions of people every month, building trust and credibility across the crypto industry.

“The media business is all about trust and distribution,” Jason explained. “Pageviews are going to zero. Nobody is going to visit a website one day. That’s why we focus on delivering value through podcasts and newsletters.”

Their podcasts, which formed the largest network in the crypto space, operated much like Barstool Sports’ model, offering a mix of expertise and relatability. Meanwhile, newsletters like their flagship Blockworks Daily kept subscribers informed, driving loyalty and engagement.

But it wasn’t just about content—it was about connection. The media business laid the groundwork for everything Blockworks did, from attracting conference attendees to converting high-value subscribers to their Research & Data platform.

If media was the foundation, events were the engine that kept Blockworks running. Their two flagship conferences—DAS (Digital Asset Summit) and Permissionless—targeted distinct audiences but shared one crucial function: profitability.

“Conferences make a really large amount of money and at a really good margin,” Jason said candidly. DAS, with its suit-and-tie attendees from firms like Goldman Sachs and Citadel, was a buttoned-up B2B affair. In contrast, Permissionless had a more relaxed, crypto-native vibe—think t-shirts, shorts, and a mix of 24-year-olds managing multimillion-dollar portfolios.

But even conferences came with risks. Blockworks had learned this the hard way in its early years, betting the farm on large events and narrowly escaping financial disaster. “The only thing that could kill Blockworks at this point is getting overextended on a large conference,” Jason reflected.

This realization led to a pivotal shift. Blockworks decided to pivot Permissionless into a smaller, more focused B2B event, avoiding the dangerous trap of chasing ever-larger audiences in an unpredictable market.

While media and events provided trust and cash flow, the Research & Data business was Blockworks’ key to building long-term enterprise value.

“Media businesses don’t get high multiples,” Jason explained. “Research and Data, with its ARR and subscriptions, drives enterprise value.”

Blockworks had entered this space deliberately, leveraging their massive media funnel to attract subscribers to the Research & Data platform. Unlike competitors who relied on sprawling sales teams, Blockworks’ brand did the heavy lifting.

“We don’t need a 30-person subscription sales team,” Jason said. “Our media business brings in over a million unique readers every month. If even 0.1% of those readers convert to the research platform, we’ve got a colossal business.”

Their approach also gave them a competitive edge. While other research firms struggled to scale without strong distribution channels, Blockworks’ media arm provided a steady stream of engaged, high-value leads.

HOUSE OF BRANDS

By 2024, Blockworks had also embraced a “House of Brands” strategy, creating sub-brands tailored to niche crypto communities. Jason likened this approach to LVMH’s portfolio of luxury brands, where each label served a distinct audience.

“Inside crypto, there are all these die-hard factions of people,” Jason said. “These cult-like communities are incredibly passionate, and we’ve built sub-brands around them.”

This strategy allowed Blockworks to scale in ways that wouldn’t have been possible with a single monolithic brand. “If it was just Blockworks, we couldn’t hit $100 million in revenue,” Jason noted. “But with these sub-brands, that goal becomes attainable.”

The decision to pivot to the “House of Brands” wasn’t just strategic—it was a survival tactic. By January 2024, Blockworks had begun to encounter what Jason called the “messy middle” of the media barbell: too broad to be niche, too niche to be broad.

To avoid stagnation, they overhauled their editorial and content strategy, doubling down on their most engaged audiences. This focus kept Blockworks agile and positioned them to grow sustainably in a volatile industry.

Scaling conferences remained a delicate balance. Blockworks had seen how quickly large events could become financial sinkholes, as evidenced by CoinDesk’s $25 million loss in 2023.

“We no longer want to make bets on conferences that could kill the business,” Jason said. “Instead, we’re focusing more on Data and Research, where we see the greatest potential for growth.”

This disciplined approach ensured that Blockworks remained profitable and avoided the pitfalls of over-expansion—a rarity in the crypto industry.

Blockworks had evolved into a hybrid powerhouse, seamlessly integrating media, events, and research to create a self-sustaining business model. Each segment supported the others, creating a flywheel effect that set Blockworks apart from its competitors.

As Jason and Mike looked ahead, their focus was clear: doubling down on their strengths while exploring new opportunities. The next chapter would delve into Blockworks today—a thriving media and data business poised to lead the crypto industry into its next phase.

CHAPTER 8
The Jason Yanowitz BluePrint

Wouter here. Now that you’ve read everything that Jason did to go from flipping MLB cards to building a multi-million dollar business. 

But the title of this chapter begs the question, What is the Jason Yanowitz BluePrint? And while I do claim to be a genius, I’m not a wizard – and so this is merely my interpretation of the commonalities or interesting things in the Jason Yanowitz story that you and I (mainly I, I’m quite selfish) can use in our quests for… Well, wealth, let’s be honest.

Study what you want – Just choose the thing that interests you the most. Simple really

Whilst simple, I know. You know. We know so many people that do not follow this simple rule. Hell, you and I may even fall under that category. So to anyone still with the ability to have some influence on this, go study what you find interesting.

Curiosity keeps the mind sharp and is a great indication of your innate interests. Follow it and listen to that pulse deeply. If you’re a founder, don’t worry too much about the career prospects aspect – after all, you’re following a founder blue print. You’re going to start a company right? 

Target a niche – Nope not niche enough, even more niche than you’re thinking

Much of the success Jason had at blockworks early on was, and still is, consistently focusing products, content and services to a niche audience. Do not target young crypto adopters, target instead the young developers working on Solana, a specific crypto protocol. 

Always start a niche whilst thinking big, and acting quick. 

Bootstrap (until you can’t) – Get rich owning the pie, then strike while the iron is hot.

Blockworks bootstrapped to many many millions a year in revenue and profit. Not raising any outside money. This keeps you disciplined and ensures you’ve got a real fit and aren’t just lighting money on fire whilst throwing parties in your office without a real business model that is proven (however fun that does sound). 

Jason and Mike reinvested their cashflow (VC founders like: What is that?) consistently, and only raised capital when they needed it to scale their Research and Data platform which is more capital intensive. 

Build assbackwards –  Acquire the trust and clients first then ship 

Blockworks began by acquiring it’s future customers. It’s unorthodox but potentially one of the best things they did. 

“We built the company ass-backwards because we didn't know what we were building. We didn't know the endgame. We just wanted to make money in the crypto space and move the conversation about crypto forward in a responsible way.

Mike and I were both 23-24 when we started Blockworks. We weren't second time founders, we had never raised. All decisions we made early on were partly driven by lack of understanding of how big we could actually make this and also the fact that we didn’t have any money both personally and in the company meant we had to do things that only generated revenue” Jason (Sep 26, 2024)

Important Note – 

Note, it’s important to highlight how crucial Mike was/is to building Blockworks. Unfortunately there’s just a bunch less information / podcasts with Mike out there – perhaps in the future I can shed more light and create a V2 of this story… 

EPILOGUE
Wow that’s a fancy word, I wonder what this is..

What is this? Why do you care? Well maybe you don’t. The epilogue for a book is usually a short summary that adds a comment/conclusion to what you just read. Instead, I’m going to use this section to talk about the sources used and areas of the article that are embellished to some degree. I want to be as transparent as possible so this section serves as an overview for why I chose to write certain scenes or sections the way I did.

Chapter 1 – 

• The opening scene is likely to have happened, but there is no story about Jason being on the curbs of the streets holding his cards -- because of his nature of flipping the MLB cards at such a young age though, it's possible this happened.

• Jason was likely in Hungary during the 2015 migrant crisis, I only note this as a way to pin-point the time. Jason graduated in May 2016. Based on typical college semesters, if Jason was a senior in 2015, his study abroad program likely took place during either the: Spring 2015 semester (roughly January to May) - Fall 2015 semester (roughly August to December). I decided to assume it fell in the latter category, hence the scenery described is cold. Similarly, my comment on the ‘new year came and went’ is an assumption that Jason indeed had his study-abroad during the Aug-Dec window. 

• Similarly, there's no mention of Jason regularly visiting cafes or bars -- but as a student in the city it's likely something he did. And Jason has mentioned how the passion of the Hungarians about Bitcoin was his first real introduction to crypto. As such the words the “Hungarian student” sais to Jason aren’t verifiable, but likely to have happened.

Chapter 2 — 

• It's unclear if Jasons routine was early lectures and time afterwards to debate or sit in the library. But given his study, this isn't an unreasonable assumption.a

• The story about Jason selling Verve in the Van Dyke dining hall is unclear if it really happened. Jason has talked a bunch about specifically him NOT wanting to be the energy drink guy on campus, which is why he quickly found out about online marketing. This scene, whilst fictitious, could have happened and was used to show a transition to Jason learning about online-marketing.

• Jason did indeed stop with verve before he left for Hungary, I decided to include his Hungary - study abroad experience - in the previous chapter because of the link it had with Jason's family roots. Sue me (don’t), but I think that made for a better transition.

• Jason really did live that close to Michael in New York, there seems to have also been a third roommate who I reference in the writing later on briefly.

• The scene with Jason being barked at by older associates at his first job is made up, however the sentiment comes from several stories Jason has told about him being laughed out of the room in meetings that likely were to have happened as told here.

Chapter 3 — 

• The scene of Jason bursting through the door to talk about the conference he attended, whilst plausible may not have happened exactly that way. However, this was indeed the spark that pushed Jason to want to start a consulting firm with his roommates and several of the quotes by Mike and Jason are true. 

• The interaction between Jason and Mike at the conference they attended, whilst plausible, is not verified. Jason has talked about this feeling that these conferences were shady and they could do better, this is why the scene was written this way. To highlight these feelings. 

Chapter 4 — 

• Again the scene of Jason feeling tense as Mike walked onto the stage for their first event, whilst likely isn't directly tied to any stories Jason or Mike has shared. This note was meant to be a transition into how the atmosphere likely was, and to the true quote of Michael introducing the conference assuming familiarity between several attendees.

• They really did close a $8k sponsorship – inbound! Again just goes to show the power of brand and putting yourself out there, kudos.

Chapter 5 — 

• The scene with Mike, Julie and Jason in the room describing what they should do next is fictitious, but likely to have happened given Jasons' recounts of the three of them hustling to figure out what to do next with Blockworks.

Chapter 6 — 

• The scene with Jason getting an injection mid fundraise call truly happened, listen to the story Jason tells here

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