The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 29 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Destin: Venture funds succeed through great founders, not aggressive terms
“And honestly, on top of that, I don't know of any fund that was ever returned on nasty terms. Funds are returned by backing the right entrepreneurs and exceptional outcomes.”
Destin: Emerging VC managers have no leverage if LPs default
“Especially if you're an emerging manager and you're a first time fund, are you going to go sue one of your LPs because they don't pay? The reality is like, you kind of have no leverage. You're just a sitting duck. And if people decide not to pay you, then they…”
Destin: Tier-Two VCs Struggle to Return $500M+ Funds
“But if you're a tier two VC running a five to eight hundred million dollar fund, you know, it's extremely hard to actually provide the kind of returns that really venture demands.”
Destin: Non-Strategic Startups Force VCs Into 40% Secondary Discounts
“Because if you're not strategic, nobody has to buy you. If nobody has to buy you as a VC, I'm going to sit on that position for 12 years and end up selling it secondary to a horrible secondary buyer who's going to take a 40% discount on my book value.”
Destin: Startup financial plans are a fiction, not reality
“The plan is a fiction. The plan is a framework for which to think about the future. You know, the moment you finish writing it, the conditions change, etc.”
Destin: Forcing startups to hit plans drives bad decisions
“In fact, even worse, if you force a company to hit plan, and they're not hitting plan naturally, you're probably making the wrong decisions for the business long term.”
Destin: Walking away from top deals over minor valuation differences is foolish
“Now, if you say no to a world-class deal because the pre-money is three million off what you thought it should be, you're an idiot. Because world-class deals don't come through your door every day.”
Destin: Founders picking investors over small valuation gains are short-term optimizers
“But if they're trying to get you to climb up a tree and kind of make their ultimate selection based on a couple of million bucks of pre-money, that to me is usually a signal that you're a short-term optimizer and not somebody who's going to build an amazing bu…”
Destin: Board members must fully back the CEO or fire them
“If you're backing the CEO and he's running the company, It is your job to be behind the CEO. If at some point you make a decision to remove the CEO, make a decision to remove the CEO. What you're not allowed to do is be like a fucking carpenter ant that's like…”
Destin: Europe penalizes startup failure far more harshly than the US
“And I think very often, especially in Europe, Founders are being made to feel extremely guilty when things don't work, whereas in the US you find these attitudes very different, which is like, hey, we tried, it was a big ambitious problem, you know, turns out …”
Destin: No one in venture capital will train or mentor you
“Nobody will train you, nobody will mentor you in a way that's really meaningful, and that from day one, what you have to do as a young person in venture capital is learn every aspect of the trade.”
Destin: Portfolio of 25 seed companies mitigates venture loss risk
“The reality is if you invest with a certain level of discipline across 25 companies, you own enough of them, you know, 10, 12, 15, 18%, you're actually really looking at a relatively spread risk and with odds of certainly returning a multiple of capital that a…”
Destin: Founder Mental Limits, Not Business Potential, Constrain Scale
“You can systematize your thinking around achieving large outcomes, and it's more a question of your own mental limitations than usually the businesses themselves.”
Destin: Replacing Startup Founders Destroys Company Magic
“When you replace founders, you lose the magic.”
Destin: Investors should test founder responses to conflict pre-investment
“Find a disagreement with the founder before you invest, because your conflict resolution mode is important, and actually the person's reaction to conflict or to pushback is also important.”
Destin: Early Market Sizing Top-Down or Bottom-Up Is Unreliable
“I think your ability to assess markets Either bottom up or top down at the beginning of a life of a new company or a new, new segment is extremely hard to do. And very often because the legacy industries are unattractive.”
Destin: Founders Should Never Take Investment From Toxic Investors
“My only recommendation, which I always tell entrepreneurs, is please don't ever take money from assholes. You cannot fire your board members. It is probably not worth it in your life in general. I'd rather not get funded than take money from people who are tox…”
Destin: Founder-Friendly Investors Prioritize Companies Over Their Fund Partners
“Founder friendly means I will leave my fear at the door of the boardroom because I will come in and do the right thing by the company. Not by my partners, you know, not whatever. I get roasted at the fund level because the company isn't doing well. Well, I wil…”
Destin: The best entrepreneurs require no VC help
“The best entrepreneur, like Alex Chesterman at Zoopla, for example, the best entrepreneur is someone you don't really need to help.”
Founders Get Fired Primarily Due to Boardroom Trust Breakdown
“Part of the reason why founders get fired in the process of scaling is, is one of is the reason, the primary reason is a breakdown in trust at the board level.”
Destin: VC is not intellectually hard; overly smart people make terrible investors
“There's nothing fundamentally difficult intellectually about being a venture capitalist. Like, it's not like you need to be a rocket scientist to do it. In fact, people sometimes who are too smart can be terrible investors.”
Destin: VCs earn a bad reputation by abruptly pulling founder support
“The reason why VCs get a bad rap is because typically they'll be like, founder, supportive, founder, supportive, love the company, and then suddenly from one day to the next, they're like, actually we're not backing you. And entrepreneurs fucking hate that wit…”
Destin: Detailed VC rejection emails systematically lead to founder arguments
“So I used to write these beautiful no emails that were very, very well grounded with a lot of feedback. You know what systematically happens is people come back and they're like, you didn't get this, you didn't get that. It's like, I'm actually not trying to b…”
Destin: Venture capital risk lies in exit duration, not investing
“I think we do have a risk is on duration. You know, when are the returns going to be realized? Because it's as we know, it's easy to invest. It's extremely hard to exit.”
Destin: Dysfunctional boards focus on reporting over forward-looking decisions
“Dysfunctional boards tend to be reporting boards where there is distrust with the entrepreneur, usually because they don't spend enough time with the company and, or they forgot, they lost the empathy of understanding what the, what journey the company is on a…”
Destin: Startups cannot afford hiring mistakes in their first 8 to 10 key hires
“Your core eight to 10 first key hires, especially at the executive level, need to be great. You really just cannot afford to make too many hiring mistakes”
Destin: Hiring wrong co-founders is top reason seed startups fail
“The number one reason why seed companies fail is because they hired the wrong co-founders.”