As Gleb will be training the TOP 40 teams of sTARTUp Pitching 2022 on how to present their ideas to investors, we wanted to pick his brain about a few subjects. How did it go? Let’s say we managed to cover the first letters in the alphabet—leaving plenty of topics for future conversations.

Do founders make mistakes? The answer is a trope in itself. I don’t want to go into making another listicle on the seven deadly sins of pitching and how to atone for them.

In essence, it’s about how you think and approach fundraising meetings. It’s about your frame of mind and managing expectations. A founder needs to understand that raising capital is fundamentally a human-to-human interaction. If you come to a meeting expecting that you are just going to speak for three minutes, the VCs will ask you questions and then give you money in a few weeks⁠—well, it doesn’t quite work like that most of the time.

The classic metaphor is dating. If you come to a date with a stack of papers about your genetics, IQ test results, and Grade Point Average and are like, “Here’s my data. Please analyze it and get back to me if you’d like to have a second date,” it likely won’t work. Dating is not a perfect analogy, yet it’s a useful one. For example, if you don’t open up to some extent and show vulnerability, it’s hard to build the initial trust and get to the next meeting. But that doesn’t mean you must reveal every dirty laundry item on your list. 

Unfortunately, because of the public showmanship of Shark Tank, Dragons’ Den, and other competitions, people develop a misconception of the relationship dynamics and how to engage in conversations with investors. If you approach it as a rigid system where everything is deterministic and predictable, then it is not. Yet there are still patterns, best practices, and a science to it, much like in blackjack or poker.

It’s rough waters, for sure. But so it was during COVID. So it was during the financial crisis. It is always going up and down, like a rollercoaster. I believe it’s best narrated by Jeremy Irons in this scene from Margin Call.

I think the Stoics had the right idea. You cannot control outside events. What you can control, though, are your reactions and how you prepare for your date or meeting. How do you show a portion of yourself, or at the very least develop a trailer for your movie? Will I want to meet you again? Do you understand what my incentives are? Do we get each other? It’s not a one-way monologue.

Instead, it’s a conversation between human beings—and a very specific one. You will have many of them, and most of them will not lead to getting money. But you can learn from each one. You can open up, and maybe that person who said “No” in the initial round might say “Yes” two rounds from that.

You cannot control the outcomes—whether you get the money or win a pitch competition. But you can control the systematic process of preparation and building relationships with investors, leading to better outcomes over time.

What has shaped your thinking?

Here's a silly answer—books. Experience too, but you can go through 40 years in a profession and stay relatively the same if you don't deliberately process all that data to generate your unique insights.

So I've kept growing during the last ten years I've been doing this job. And about five years ago, I started investing a great deal into research and development. For example, I currently have an applied statistician on a retainer analyzing series A funding rounds. We're seeing whether a group listening to a short pitch can make predictive bets about the future and whether it's statistically significant.

So if you ask me what shaped my thinking: every darn book I've read and how I process my ten years of experience. It's not linear. It's sometimes additive and compounds, but at some point, you reach a point of criticality, which changes the way you think—you become a different person.

It's like you have a duality where you want to be accepted and appreciated for who you are but at the same time have a need for growth and discovery. If your need to change, or at least the pain of not changing, is more significant than your desire to stay where you are—that's the sweet spot where I can help.

Thanks for Feedback about the art and science of receiving feedback is a book I keep recommending. So is Scale by Geoffrey West about scaling in complex systems and networks.

About biology, Behave and Why Zebras Don’t Get Ulcers by Robert Sapolsky, a researcher who spent 30 years studying baboons in Africa.

Also, Why We Sleep by Matthew Walker. The book has issues, but it makes a good point for sleep. So, please sleep; your body is a cage and will obey you better.  

You’ll find more titles on my Goodreads account or my book recommendations in the Startup Wise Guys newsletter.

It’s like asking if I like gravity. Sure, I like gravity, especially when I’m lying down or running. In a nutshell, complexity is a fact of life.

Issues arise when people want simple answers to complex problems; I deal in complexity. What is ironic is that I work in a field that helps people communicate complex ideas in a short amount of time.

I care about teaching. A natural part of teaching is helping to shape how people think. The challenge here is that humans don’t like incomplete stories. They avoid uncertainty and attribute causes to fundamentally random events to make themselves feel safe and in control.

If someone says that I help founders with their three-minute pitches, then yes, I do that. My main job, though, is to nudge their thinking that can lead to better fundraising outcomes over time.

One thing that you may not know is that I used to play Magic: The Gathering. And now I'm gathering a group of people, together with an Italian friend of mine, to play Dungeons & Dragons, a fantasy storytelling game. We’re nearly full but still accepting party members.

E ‒ (Exciting) Entrepreneurs

You are meeting so many young, nascent startups. What exciting trends do you see on the horizon in the sector?

I’ve been in business as a pitch coach for a while now, so I’m pragmatic. Some topics repeat themselves: somebody is always doing cleantech, fintech, SaaS, marketplaces, or e-commerce. Sometimes a new keyword, like metaverse, pops up; some would say it’s just rebranded AR and VR. Some keywords come and go, some merge, some die.

But if you ask me on a human level, I hope that out of 1000 people, one or two can come up with meaningful solutions not to the low-hanging fruit but to the fundamental complex problems we face, like food security or CO2 emissions. Or at least that a large chunk of the people who did not build their companies can contribute their intelligence, resources, time, energy, and contacts to helping the ones who are trying to make sure that we will not run out of food, clean water, and air, or that the temperature will not go too high.

However, what do VCs chase? A 3x cash-on-cash multiple at the very least. You generally have to deliver that return in 10 years or less; if you don’t, you’re unlikely to raise the next fund. And you have a limited pool of projects that you’re competing for.

I’m simplifying this a great deal, and I am not a cleantech expert. It reminds me of an old saying, “Certain types of people like to create problems and then heroically solve them.”

Maybe it’s time to grow up and build something that allows us to survive, not just as a futuristic multi-planetary species. How about we ensure this spaceship we call Earth runs well enough in the short term for us to survive long enough to see that future?