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The Full Ratchet

Investor Stories 461: Feast and Famine in Crypto, When to Take the Off Ramp, and Evaluating Founder Temperament (Simpson, Chaddha, Orthlieb)

6 min episode · 2 min read
·
Naveen Chaddha,Ariana Simpson,Ben Orthlieb

Episode

6 min

Read time

2 min

Topics

Personal Finance, Investing, Startups

AI-Generated Summary

Key Takeaways

  • Crypto Burn Cycles: Crypto founders face amplified feast-and-famine cycles, exemplified by 2021's excess spending, where companies that acted early on burn reduction advice survived while those that ignored it ran out of capital before reaching their next fundraising milestone.
  • Exit Timing Discipline: Naveen Chaddha of Mayfield identifies a $2-3B acquisition opportunity missed during 2021's peak multiples, where company valuation later compressed 120x. Investors should document explicit valuation bubble warnings in writing to founders, creating a record that supports future off-ramp decisions.
  • Founder-Investor Alignment on Exits: When founders reject secondary exit opportunities at peak valuations, investors face a structural tension between supporting founder autonomy and protecting employee outcomes. Chaddha estimates the missed delta represented life-changing wealth for thousands of employees across a multi-billion dollar gap.
  • Founder Temperament Threshold: Blue Moon's Ben Orthlieb references Emergence Capital's Jason Green framework: back founders who are 50x more brilliant than difficult, but explicitly calibrate tolerance for temperament before investing, not after conflict emerges, to avoid reactive decision-making mid-portfolio.

What It Covers

Three VCs from a16z, Mayfield, and Blue Moon share high-stakes conflicts around crypto burn management, missed multi-billion dollar exit timing during COVID-era valuations, and evaluating founder temperament at the investment stage.

Key Questions Answered

  • Crypto Burn Cycles: Crypto founders face amplified feast-and-famine cycles, exemplified by 2021's excess spending, where companies that acted early on burn reduction advice survived while those that ignored it ran out of capital before reaching their next fundraising milestone.
  • Exit Timing Discipline: Naveen Chaddha of Mayfield identifies a $2-3B acquisition opportunity missed during 2021's peak multiples, where company valuation later compressed 120x. Investors should document explicit valuation bubble warnings in writing to founders, creating a record that supports future off-ramp decisions.
  • Founder-Investor Alignment on Exits: When founders reject secondary exit opportunities at peak valuations, investors face a structural tension between supporting founder autonomy and protecting employee outcomes. Chaddha estimates the missed delta represented life-changing wealth for thousands of employees across a multi-billion dollar gap.
  • Founder Temperament Threshold: Blue Moon's Ben Orthlieb references Emergence Capital's Jason Green framework: back founders who are 50x more brilliant than difficult, but explicitly calibrate tolerance for temperament before investing, not after conflict emerges, to avoid reactive decision-making mid-portfolio.

Notable Moment

Chaddha admitted it took him a full year to emotionally recover from the missed exit, and he expects to repeat the same decision in future situations, prioritizing founder support over optimal financial outcomes.

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Episode Transcript

Today's episode of TFR is brought to you by .techdomains. The right .com is usually taken, and adding extra words weakens your signal. I see thousands of decks every year, and a clean domain still matters. That's why founders choose .tech. It's simple, modern, and sends the right signal. Secure your .tech domain early. And this episode of TFR is brought to you by the American Arbitration Association, where smart startups and investors turn for fast, efficient, and cost effective dispute resolution. Visit adr.org/tfr to learn more. Now here's the episode. Welcome to the podcast about venture capital, where investors and founders alike can learn how VCs make decisions and reach conviction. Your host is Nick Moran, and this is the full ratchet. Welcome back to TFR. On today's special segment, we discuss major conflicts that guests have faced and how they resolve them. Here's a special segment called high stakes conflicts. On today's special segment, we have Ariana Simpson of Andreessen Horowitz. Without revealing specifics, talk about one of the highest stakes conflicts you faced as a VC, why the issue occurred, and how it was resolved. One of the biggest categories of challenges is managing burn. And that is something that tends to be more of an issue in well, it's it's generally an issue for all founders, but I think it it is even more pronounced sometimes in crypto because you have these kind of feast and famine cycles whereby it's 2021 and everybody's raising a bajillion dollars. And so, everybody feels very rich and, like, they can hire a million people and do all these things and, you know, spend a million dollars on a party because they've just raised a $100,000,000 and so forth. But the flip side of that is that, you know, there are famine periods in which it's very difficult to raise money and users may have, you know, temporarily left the space or things like that. And so, you know, it it takes a lot of discipline and self control to be a founder who can, like, appropriately manage those different cycles. And so what those cycles mean is that I've had to have many difficult conversations about managing burn with companies. And the reality is some founders are willing to take that feedback and act on it early enough that there's still time to turn the ship around. And in other cases, they don't. And then the company ends up running out of money. So, I can think of you know, that's kind of the the general take. There are many specific instances that I can think of that, you know, I won't address by name. But I think what, as a founder, you have to remember is that, you know, your investor is on your team. Like, we don't want the company to run out of money. And making sure that, you know, you're managing the business in such a way that other investors are going to you're you're …

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  • by Emergence Capital

    Blue Moon's Ben Orthlieb references Emergence Capital's Jason Green framework: back founders who are 50x more brilliant than difficult, but explicitly calibrate tolerance for temperament before investing, not after conflict emerges, to avoid reactive decision-making mid-portfolio.

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