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Charlie Songhurst

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2025-06-27
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2025-06-27
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  1. “Backgrounds, often in deep tech and PHDs, they're sort of like generals fighting the last where they think of prestige as the currency because it is in academia. And so they just think if we do amazing work and we tell the world about that amazing work, good things will happen. Because as a holistic, that did work, but it means they don't engage with the revenue. They don't get quite product market fit. It's too much a sort of ivory tower intellectual exercise. Or conversely, do they just sort of think we get momentum, we get revenue, we get traction, it all work, and they haven't really thought about the microeconomics and unity economics of a scaling company. And so I almost inverted and say, don't study greatness. Study failure and work out how not to be that. If you're sort of thinking of history, trying to be a sort of good Oman Emperor as Augustus would be really, really difficult, not being as incompetent as a Caligula seems really easy. And so as a packed good advice, not making the catastrophic mistakes.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “You can find a commonality in their mistake. Maybe they all, I don't know, offered their chin to the opponent or something. And in startups, I think there are common mistakes. There's an original sin about capital raising. I see so many startups three to five years in still haunted by bad capitals at the beginning, some investor they don't want, some valuation that was hopelessly dilutive and puts VCs off now. Often one of the things that I see fairly well with success is how quickly they exit their first employee that doesn't fit. And I think what that's actually showing is are they willing enough to be disagreeable to make the company what they want? And so the willingness to cross that chasm and often you're dealing with young founders, that's a major infraction point. And if you don't do it, that often leads to a toxic culture and bad results, then there's sort of more subtle maladies like turning things into an academic project, particularly with founders with very strong academic.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “Seen the commonality. And so, how much of that is sort of booking in an athlete at the peak of their performance and not seeing the 10,000 hours of practice that got them there? And I could almost argue you could invert it and say, what are actually the causes of mortality? And how do we just avoid suffering that mortality this year? And if you survive long enough, maybe greatness of entry becomes you. So one of the things I think that sort of is perhaps underestimated is if you want to live forever, maybe don't start thinking about studies centenarians, instead work out how to not die of a DUI or drink driving or any of the smoking 20 cigarettes a day. And to some extent, the same in entrepreneurship is, it would be amazing. And of course, the problem with sort of the observation of the world is people spend a lot of time studying greatness. They don't study failure. They study Mohammed Ali, they don't study all the heavyweight boxes that faked out after losing their first match. But maybe if you study all of those,”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “I will maybe, for the socratic sake of it, sort of take the opposite argument and say, I think one of the mistakes it's put into is just sort of seeing evavescent genius because you're seeing people at the height of their powers, you're not seeing them on the way up. There's that famous quit of Bezos, I think, in 1999 with Amazon sprayed and spray paint on the back of the office. It would be really interesting if you talk to him whether he is similar to the Bezos of today. Because in the intervening 20 years, remember, you've got this incredible training program for the mind. They're working every hour in the startup. They're talking with the smartest people. They're constantly getting new information. They're hiring, they're firing, so their pattern recognition of executives gets so much better. They've got a million failed initiatives. So they have all these learnings of what not to do. They've got all the things that have worked and they've seen what scale they've done.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “And connect with them. And so it's fairly hard to find people that are stars in all three parts of those careers. And I think it's the same with entrepreneurship. The street smart entrepreneur at sort of pre-seed who can raise money with a good narrative and get energy and recruit people and sort of create a sort of sense of momentum and esprit de corps is often very negatively correlated with the sort of personality that wants to put in quarterly HR reviews and QBR reporting and really make sure that the finance team is taking at a later stage. And then conversely, often the entrepreneurs do very well later find the early stage capitalizing hell and earth because in some ways they're so tightly gripped to reality and they're slightly pessimistic, which makes them fairly good at sort of avoiding chaos, often makes them very bad at pitching.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “Between sort of VP leaders and functional heads, defining those well and managing through that transition is just so important. And there's nowhere where someone learns that through the process of entrepreneurship. One of the things that's, I think, very interesting about people's careers in general is the early stages and the personalities go into them often of negative correlation with the later stages. So if you look at a sort of McKinsey or Goldman Sachs analyst, often what they need is attention to detail, strong work ethic, high diligence, high conscientiousness and sort of by factors, all those sort of things. If you look at middle management of those companies, they need good project management, good ability to abstract and structure problems, good ability to pull a team together and create team morale, and the sort of being costs of detail and the technical knowledge matters less. And then if you look at the sort of partner level in those firms, often all that matters is relationship building and sales and charm and the ability to empathize with the client.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “Tends also to be capable of politics. And because the world is not composed of saints, as an organization scales, the level of internecine politics increases exponentially. Someone once said to me, the difference between a great company is one where the exec spent only 25% of their time playing politics and a bad one is where it spends 50% of their time paying politics. And that delta is the entire Gaussian bell curve from the best fortune 500 company to the worst. And I think one of the things that really matters as a founder is acting as a dampener on politics. So reducing Internet warfare, reducing the tendency for marketing to try and take control of the sales funnel, reducing tendency for the head of sales to want to take over sort of inbound marketing, trying to stop the CFO controlling spending so tightly that you don't get positive return capital investments by sales, trying to stop sales, get in so much control over spending that your margins go out of control. All those boundary conditions.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “Think the irony is it is absolutely something that can and should be coached but often isn't. So often the people that get it intuitively are the people that survive. But there's no need for that. It can just be coached in. And I think a lot of it is you get this very strong transition when you're a very small startup. Most of the people you're employing just come in and do their job and go home. And the drawback of that is you tend to end up having to do type management, a lot of micromanagement. And the beauty of it is you tend to get a very low level politics within the organization. Then you get this transition to where you're hiring people that are sort of execs would be the sort of headhunter's description, VPs, senior people. And the beauty of these more senior people is you can give them much more complex tasks, build me a product division doing this, go open European markets for me. And the drawback is it, anyone capable of those complex conceptual abstractions necessary to do that.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “Department Strong HR Department, that again is a big filter. And so those are sort of filters by stages. What's interesting is some of those you can do when you meet something preseed. One interesting thing is I sort of close my eyes and think, can I imagine this person on a public company conference call remembering the Microsoft in the Microsoft earning schools? And I'm thinking, can I imagine them sitting as a sort of CEO next to their CFO talking with all the sort of Austrian Ecti analysts and the buy side on the phone and just be incredible enough and deep enough mature enough to pull that off.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “By chance or by skill, they're just intuitive by third. Then when you get beyond that sort of series B and beyond, I think it's institution building. And one of the interesting problems is the sort of people that become entrepreneurs are often full of energy and sort of flexibility, almost a sort of combination of street smart and book smart. But there's a point where they've hit product market fit, where actually what they're doing is repeating a process at scale. And to repeat a process at scale, you need to build an institution. And often that sort of is almost anathematic to their personality. If you're going to take a revenue from 42 countries, you really need a well-developed finance department. Once you get to a certain size, you will always be in court cases because of being sued by ex-employees. You have patented infringement suits. You'll be debt collecting customers that didn't pay. Like the shift to sort of building an institution with institutional norms and institutional values and institutional culture and all the boring stuff of building strong finance departments, strong legal...”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “In the labour productivity per person. There's a term in microeconomics called managerial diseconomies of scale. And I think in some ways the angle of the decline of productivity per person is the difference between the sort of the stripes and great startups and the failures. And maybe if you're a great startup as you go from 10 people to 100 people, output per person drops 15%. And if you're a bad startup, it actually drops over 90%, with the result that often 100 people's startups produce less than they did when they had 10 people. because the managerial collapse has been so extreme. And one interesting thing is if you look at the companies get very big, maybe there's a sort of interesting explanation where more than the shared attributes was an instinct for the sort of structures and processes of management that were shared between Gates, Zuckerberg, Bezos, the Carlitons, all these sort of super talented people. Because my guess is they didn't receive formal instruction on it. Their VCs and advisors weren't that helpful on it. It may be either”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “Most intelligent strategy sometimes just won't find it, and someone will just fall asleep, put the pan in a Then, when you move to Series A, it's really all about labor productivity, but in a different form. It's can the manager scale? And one of the fallacies is most early stage startup founders think they're managers, and they're actually not. What they have is a team that's actually managing them. Because when you're managing, say, 10 or less people and you're spending time with them every day, what's actually happening is them managing you by influence because they know you well enough and they talk to you enough to work out what your desires are. So as long as you're articulate and energetic and sort of engaged, you actually don't have to manage the team manages you upwards. But when you scale to 30 people to 90 people or above, you no longer have those personal connections and you have to move to formal management techniques. And that's like a sort of Fermi paradox great filter. It wipes out an amazing amount of startups. And the way that's divinced is a collapse.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “In some ways, it's too tied together. So I think the dominant sort of failure mode for startups is the same at each different stage. So sort of precede to seed, you basically have a failure to achieve labor productivity, which is just a polite way of saying the team doesn't come together, doesn't gel and produce good output. Usually a team that just produces good work will generate enough sort of kinetic energy to get continuing funding. Once you're sort of going from seed to series A, it's another single cause, which is failure to get product market fit. You're basically on the search for demand curve and you either find one or you don't find one. And this is where you've got the highest element of pure chance in a startup. It always feels akin to sort of gold perspecting in the California Gold Rush, which is you can be good or you can be bad, you can do the right thing, you can do the wrong thing, but there's some ill-adducible amount of chance. The wisest perspector with the best maps and the”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “There's so many memories working with amazing people. The hostile acquisition of Yahoo as an attempt was just unbelievably intellectually fascinating, trying to buy a company in a hostile position for, I think, $47 billion. And just the drama and the soap opera and realizing how much path dependency matters on big deals, how much a casual comment misinterpreted by one side or the other actually changes the outcome. It's remarkable how little system theory there is in the sense of if you an experiment again and again, I think you would get a lot of different results in M&A activity. Whereas in things like product usage, good products and bad products would probably be the same in each experiment.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “Studied politics fast and economics at Oxford, ended up very brief in McKinsey, then at Microsoft, and then sort of bumbled my way into becoming an investor and do a lot of angel investing. So I think I've done about 500 Angel investments. I think the actual number's 483 and about 300 in the portfolio at the moment.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “I think what you're looking for is founder market fit. I think there's a sort of mistaken concept that's a platonic ideal of an entrepreneur. And I think maybe there's two very basic things. There's energy and there's sort of cognitive ability. But after that, you're really looking for fit. So if you take the sort of prototypical consumer founder, they tend to have more empathy for how people behave. Whereas if you take the classic enterprise founder, they tend to be more national because in some ways you can just go and ask your customers what features do you want and go build them. And so you go down those different lines. And I think there's a lot of fallacy in that sort of platonic ideal. What you're actually looking for is someone who's a good fit for a business.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “Of the above. The founder one is fascinating because you actually end up going down different lines in helping them depending on whether they answer the power and the money. Founders that answer power tend to need help more on managing their startup capital efficiently. They tend to be the ones that spend more. They tend to be the ones that over-expand. They're often too aggressive. Conversely, the ones that answer money tend to be vent efficient, but are often slightly too cautious, slightly underaggressive, sometimes not willing enough to stamp their authority on the company and make it the culture that it needs to be to be successful.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “A lot of people have negative utility from fame. A lot of people start with power and then when you push them, it's actually money, but they don't want to say it. And that's more true outside of the US culture than it is in the US. It's particularly true with Europeans. And so a lot of it is trying to get people to actually say what they truly believe as opposed to say what they think they should say.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “Utilitarian impacts in the world. Whereas if you're working Sen FinTech, you're less likely to sort of have that utilitarian positive impact.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “So it's a two part question. One is the virtues, which is working with people you like, working on amazing problems and having impact, and then the three vices, power, money, and fame. And you can't avoid them. They have to be stacked separately. And it's really trying to get at the differences between, there's no good answer, but there are definite good fit answers. So someone who's interested in power tends to be better at execution. Someone that's more interested in money tends to think more about some capital efficiency. I tend to avoid people interested in fame. But if you are doing something in showbiz, it would presume to be the number one criteria. If you think about the difference between sort of impact, intellectual interest working with people, you really get impression of where people are going to be happy and where they're not going to be happy. You also start to understand why certain organizations do so well. So SpaceX, if you think about it, stacks high on all three. It's intellectually interesting. You're working with amazing people and you're huge.”

    2025-06-27 · Invest Like the Best · Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] · IDENTIFIED FROM THE TRANSCRIPT · source