Keaton Nankivil on the Reality of Venture Capital (and Where Athletes Go Wrong)

The former pro basketball player turned VC investor breaks down what venture actually looks like and where athletes have an edge.

May 27, 2026

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Venture capital has a branding problem.

From the outside, it looks like a game of big checks, fast wins, and headline investments.

From the inside, it’s something else entirely: a grind built on repetition, pattern recognition, and a kind of invisible work that rarely gets talked about.

That gap between perception and reality is where most new investors struggle, especially athletes.

Keaton Nankivil didn’t come into the industry with a finance background, a business degree, or a traditional network. He started as an intern at Alumni Ventures after a professional basketball career in Europe.

Nine years later, he’s a Senior Principal leading the firm’s sportstech thesis.

In this conversation, he breaks down what venture capital actually looks like, where athletes can experience challenges, and the lesser known skills from sports that can make athletes exceptionally valuable.

This Q&A has been lightly edited for clarity and length.

Venture capital is often described as a game. What do people, especially athletes, misunderstand about how it’s actually played?

Keaton: The first thing is understanding what venture capital is.

It’s a part of the financial stack that’s historically been hard to access, but it’s also where a lot of value creation is happening now, in private markets. If you’re looking for asymmetric upside, this is one of the best places to find it.

But it’s not for everyone.

The biggest mistake I see is people entering the space without understanding their role in it.

“I’m an athlete, but more specifically I’m a basketball player. My skills don’t necessarily make me a good soccer player, so I won’t be all that useful on that field. Investing is like sports. You need to figure out where you have an edge and show up there.”

You don’t need a formal degree. But you do need to understand how returns are generated and be honest about your risk tolerance. It’s high risk and high reward. You should have a genuine capacity to take some risk with your money knowing that there is potential upside.

Because the reality is: a small number of investments actually create returns.

Before you entered VC, what did you think the job was? And what does it actually look like day to day?

Honestly, I had zero context going in.

My perception was mostly from what I heard - aggressive, sharp-elbowed, the “vulture capital” stereotype... And to be fair, parts of that exist. Luckily, most of the people I’ve met in this field are genuinely motivated by helping founders build extraordinary companies.

But the bigger disconnect is the work itself.

It’s a lot like professional basketball. From the outside, it looks like a glamorous job.

In basketball, you see the three-pointers, the dunks, the game-winners. What you don’t see is the warmups before practice, the repetitive drills during practice, and the post-game rehabs.

VC is the same. You hear about the headline investment. But the day-to-day grind before and after the investment is the actual job.

I still cold email founders every week. I take hundreds of calls a year to find a small number of opportunities that fit our fund strategy. And a lot of the job is tracking companies, supporting founders in moments no one hears about, and maintaining LP relationships over long periods of time.

It’s repetitive. And that’s the point. Because every now and then, that repetition compounds into something meaningful.

Very few people are willing to start from the bottom when they transition careers. You chose to start as an intern at Alumni Ventures. What gave you the conviction early on to commit to this path before you had any real proof it would work out?

Honestly, I think “chose” is such a generous word. I didn’t have a clear path after basketball and kind of just stumbled into it.

The internship opportunity at Alumni Ventures came through people I trusted, and that mattered more than anything else. I believed in the people before I understood the asset class.

Looking back, that was enough to get started.

“Sometimes conviction follows commitment.”

There’s this idea that you need conviction upfront. I don’t think that’s true, especially for athletes transitioning into something completely new.

A lot of this was just showing up, doing the work, and stacking reps until things started to make sense.

The hardest part actually wasn’t the lack of conviction early on. It was accepting that while I was a high-level operator on the court, I was a beginner here. I had to earn the right to compete and win in this space.

How did your experience as a professional basketball player shape the way you think as an investor today? What skills transferred over well to the investing world? Was there anything you had to unlearn?

The biggest thing that transfers is an appreciation for the dirty work that doesn’t show up on the stat sheets.

I remember a game in Spain where I wasn’t playing well, and a coach pointed out that a screen I set created a key three-point shot for a teammate. That really stuck with me.

“A three-pointer is really the sum of all the little things that came before it - the screen, the cut, the pass at the right moment.”

VC works the same way.

A successful investment might trace back to a cold email, a relationship built months earlier, or internal work that helped the team move faster. It’s the result of invisible, dirty work that happens long before a check is written.

On the flip side, what doesn’t translate as well is structure.

“The skills that make you successful in sports, like deferring to the coach and executing plays in a neatly-defined system, can actually hold you back in venture.”

In sports, there’s a clear chain of command. The coach calls the play. I would execute the play. And for a long time, that’s exactly what makes me valuable to a team.

In VC, the most successful investors tend to be the independent thinkers - the ones that can look beyond the status quo and push boundaries.

They generate alpha from challenging the general consensus, forming original ideas, and trusting their own instincts.

That’s something I’ve had to learn over time.

You now lead the Sportstech thesis at Alumni Ventures. Where has your background as an athlete given you a real, non-obvious edge when evaluating companies?

Context.

As an athlete, I’ve been fortunate to experience almost every part of the sports value chain.

I’ve played in youth sports. I’ve gone through the recruiting process as a college recruit. I’ve been part of teams at different levels. I’ve used performance technology as a pro. I’ve been a fan consuming sports from the outside.

So when I look at a company in this space, I’m not imagining the user. I’ve been the user.

That helps me quickly understand who a product is really for, where it fits, and whether it solves a real problem.

But there’s a trap in that too.

My experience might feel universal, but it usually isn’t.

What worked for me, or what I would have wanted as an athlete, isn’t always representative of the broader market.

So I try to treat my experience as an input. It gives me a starting point, but it doesn’t replace doing the work. If anything, it just helps me ask better questions and build conviction faster.

Athlete-investors tend to gravitate toward Sportstech and CPG due to familiarity. What’s the most common mistake they make?

“As an athlete, I’m wearing two hats every time I evaluate a company. My consumer hat might love it. My investor hat asks a completely different set of questions. The mistake is only wearing one.”

I love this quote from Mark Cuban on Shark Tank: “I’ll be a consumer, but I’m not going to be an investor.”

As an athlete-investor, the most common mistake is investing in products I would have personally wanted - a youth training app, a performance supplement, a fan experience product - and mistaking that for real diligence.

Just because I like something doesn’t necessarily mean it’s a good investment.

Take CPG as an example. You can build a great business there. But the structure of these companies can make it hard to achieve venture-level returns.

Margins are tighter. Growth is more linear. Capital requirements are higher.

That doesn’t make them bad businesses. It just means they may not fit the venture model.

The second mistake is ignoring portfolio construction.

The reality is, most investments won’t work. That’s just how the asset class works.

Venture is a portfolio of opportunities. You need to see enough deals to understand what “great” actually looks like, and then let the great investments balance out the ones that never reach escape velocity.

You’re building an apprenticeship model for athletes at Alumni Ventures. Why is that the right model for venture, and what does it unlock that traditional education doesn’t?

“The issue isn’t raw intelligence. I’ve seen it up close. The gap is access and exposure. Give athletes a structured environment to learn by doing, and the ceiling is very high.”

First, the trust factor. You meet a fellow athlete and the bond is almost immediate - there’s shared values, shared communication, shared experience. That’s multiple layers of affinity. It matters when you’re learning something hard and unfamiliar.

Second, and I say this with real conviction, is that athletes are among the smartest people I’ve ever worked with. A lot of my former teammates didn’t attend top business or finance programs. They are just as sharp as many of the people I work with today. The issue has never been intelligence. It’s been access and exposure.

Third, venture is a craft. Kobe Bryant used to talk about basketball as a craft - you are a craftsman, and you hone your craft over time. Investing is the same. You need feedback loops. You need a space to make mistakes safely. You need someone who has been through it to guide you.

Ultimately, my goal is to help athletes become a formidable part of the venture ecosystem. Venture capital shapes the future economy, and athletes deserve a seat at that table.

The capability is already there. I’ve seen it up close. What’s been missing isn’t the talent. It’s access, exposure, and the opportunity to prove it.

This dynamic shows up more often than people think. Athletes bring real context, especially in areas like sportstech. The challenge is turning that context into sound judgment over time.

That’s what Keaton is focused on, helping athletes build reps through apprenticeship. With the right guidance, the next generation of athletes won’t just participate in venture. They’ll play a active role in shaping it.

To learn more about VC and sportstech investing, connect with Keaton on LinkedIn.

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