“I think DeFi will never work.” – Diogo Mónica, Anchorage’s cofounder on Entrepreneurship, VCs, and Crypto’s Next Chapter

In this episode of When Shift Happens, I sit down with Diogo Mónica, General Partner at Haun Ventures, the $1.5 billion firm known for backing category-defining projects in crypto and web3. 

Diogo brings a rare founder-turned-investor perspective, shaped by his years co-founding Anchorage Digital, America’s only federally chartered crypto bank managing more than $60 billion in digital assets. He also serves as President of the NEAR Foundation, giving him one of the most unique vantage points in the crypto ecosystem.

We talked about everything from the loneliness of entrepreneurship to the structural flaws in DeFi and why, in his view, the zero-to-one phase of a company is magic.

Is Life a Single-Player Game?

We started by exploring Naval Ravikant’s oft-quoted idea that “life is a single-player game.” Diogo sees the philosophical appeal: you’re born alone, you die alone, and how you interpret the world is ultimately up to you. But in practice, he believes the lived experience is much richer with others. “Family is one of the few things you’re willing to sacrifice your own happiness for,” he said. “And in entrepreneurship, having a co-founder makes the journey less isolating and far more sustainable.”

Diogo explained why solo founders have a much harder time. With co-founders, the emotional highs and lows tend to be “phase shifted” so that when one person is down, the other can lift them back up. “Doing it solo is much, much harder,” he said. “Everything I’ve done has always felt like a team sport.”

Why Companies Fail (and the Hidden Founder Struggle)

With nearly 150 angel investments and a growing portfolio at Haun Ventures, Diogo has seen plenty of patterns. He shared that the top three reasons companies fail are: Lack of product-market fit, running out of money before finding it and founding team conflict.

Founder burnout and co-founder misalignment are extremely common but rarely discussed openly. Diogo recommends building structural safeguards early, especially if you haven’t worked with your co-founders before: longer vesting schedules, clear re-investment expectations, and mechanisms that protect the company’s cap table if someone leaves. “It’s human relationships,” he said. “But you can preemptively design for the hard moments.”

Zero-to-One vs. One-to-100

Diogo lights up when talking about the zero-to-one stage of a company: small teams, no politics, pure speed. “The first 18 months are so special,” he said. “There’s no technical debt. You’re just trying to get to the next proof point.”

He believes that in-person collaboration is critical at this stage because iteration speed is all you have. Remote work can work for larger companies, but when you’re building culture and making rapid-fire decisions, “being in a room just makes you much likelier to succeed.”

Scaling from one to 100 employees, however, requires a completely different skill set. It’s about building processes and executive teams that function without you. “Running the process and building the machine that runs the process are two totally different muscles,” he explained.

The Founder vs. VC Mindset

We also dug into the differences between being a founder and being a venture capitalist. Counterintuitively, Diogo says that people who go straight into VC often deliver better returns than ex-founders. “Founders fall in love with products instead of businesses,” he explained. “Or they imagine themselves in the CEO’s shoes and fill in the gaps, instead of listening to what the founder is actually going to do.”

He also pointed out the accountability gap in venture. The nature of the job, i.e., long feedback cycles and the ability to switch funds every few years, allows underperformers to “hide” for years. “If you really want to make money and have no accountability, venture is a great place to hide,” he said bluntly.

That said, he loves the intellectual breadth of venture investing. “As a founder, you live with blinders on. As a VC, your job is the opposite: to meet the smartest people, see the coolest things, and understand how markets are evolving.”

The Crypto Ecosystem’s Incentive Problem

Diogo didn’t mince words about the structural flaws he sees in crypto, particularly DeFi. “DeFi will never work... Not unless we align founder incentives the way we do with equity companies,” he said. Too many teams launch tokens, enjoy early liquidity, and then lose the motivation to grind for years.

His prescription is simple: longer vesting schedules (four-year cliffs, seven-year vesting) and better alignment between token holders and builders. Without that, he believes we’ll keep seeing short-lived projects and “grifters” who cash out at the expense of their communities.

Predictions for the Next 12 Months

Looking ahead, Diogo is excited about the convergence of traditional finance and crypto. He predicts we’ll see the first true on-chain IPO within the next year—a tokenized security with the same rights as traditional equity, issued and traded fully on-chain without ever touching the legacy financial rails.

“All the pieces are in place,” he said. “The next 12 months could bring the first example of real, institutional-grade integration between TradFi and DeFi.”

Balancing Work, Family, and ‘Enough’

As a father of two young children, Diogo was candid about the toll of constant travel. He tries to be fully present when he’s home in Lisbon, taking his son to school on his shoulders and carving out quality time. “I think it’s possible to do both,” he said. “But it requires constant work.”

When asked if he’s reached “enough,” Diogo said the concept doesn’t resonate with him. “Knowledge is infinite. Wealth creation is infinite. There are so many cool things I can do with money,” he said, citing his dream of one day funding a chemistry research centre in Lisbon so his sister and brother-in-law can move closer to him.

“I feel extremely happy right now,” he added. “I’m doing the things I want to, at the level of quality I want to, with very few trade-offs.”

Entrepreneurship as the Default Path

We closed on a contrarian note. Diogo believes that in 2025, entrepreneurship should be the default career path. “There’s very little downside and primarily upside, especially when you’re young,” he said. The internet gives anyone the ability to access a global market and build meaningful wealth with relatively little capital.

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