Breaking Into VC: Built With People, Not PedigreeBona's Alum, Fund Advisory Board Member, Shares His JourneyBy Denzel Gregg

When I first stepped into venture capital, I didn’t know what to expect. I didn’t come from Wall Street, consulting, or a startup. My background was all over the place: professional athlete, a stint in politics, back into college athletics, and then law school. The closest thing I had to VC on my resume was a finance degree I earned nearly ten years ago and never really used.

So, I walked in with no experience, just curiosity and the willingness to learn. Eighteen months later, I’ve realized that venture capital isn’t just about numbers, valuations, or exit multiples. At its core, it’s about people. And that’s something anyone, from any background, can learn if they’re willing to.

​The Paperwork Only Gets You So Far

One of my earliest experiences as an intern in VC was dealing with the fund paperwork—LPAs, subscription agreements, governance language. To be honest, it was overwhelming at first. I was still a law student learning how to parse dense documents, and suddenly I was looking at contracts that determined how millions of dollars would be governed.

But the deeper I got into it, the more I realized the real lesson wasn’t in the fine print. The paperwork creates the framework, but it doesn’t create trust. A Limited Partner doesn’t invest because the clauses are airtight. They invest because they believe the people running the fund will honor those words.

That process felt familiar. In law school, you quickly learn that it’s not enough to recite rules; you also have to apply them in a way that gives people confidence. A client doesn’t hire you just because you know the statute. They hire you because they believe you’ll use that knowledge to protect their interests. The same is true with LPs. They’re not investing in the document. They’re investing in the people behind it.

What I found is that the paperwork process is actually a relationship test. It forces you to explain things clearly, to be transparent about risks, and to show humility when you don’t have every answer. If you handle that process with openness, the documents become a safety net. If you handle it with arrogance, the documents become walls.

One of my earliest lessons in VC was simple: the documents set the rules, but the relationships set the tone. The trust you build in those conversations lasts longer than any signature.

Founders Are Betting on You Too

I used to assume the dynamic in VC was one-sided. Investors had the money, founders needed it. But after sitting with dozens of founders, I realized it’s more mutual than I ever imagined.

When a founder takes your capital, they’re not just accepting a check. They’re making a bet on you. They’re asking themselves hard questions: Will this investor stick around when things get messy? Will they make introductions that actually move the needle? Will they believe in me when the numbers don’t tell the whole story?

Some of my most meaningful experiences in venture haven’t involved spreadsheets or valuations at all. They’ve been the moments when a founder called after running dry on capital and we worked together to develop strategy and a path forward. Or when we connected them to someone in our network who helped accelerate their sales process by months. Or when we simply listened, no agenda, because sometimes that’s what a founder actually needs.

It reminded me of my time as an athlete. A great coach isn’t measured only by how they celebrate wins, but by how they respond to losses—what they say in the locker room when the scoreboard looks bad, how they instill belief when momentum feels gone. Founders, like athletes, need people in their corner who believe in them not just when they’re winning, but when they’re fighting uphill.

Writing a check is the easy part. What founders really remember is how you showed up when there wasn’t a clear win on the table. Money is transactional. Belief and support are relational. And in the long run, founders gravitate toward investors who invest in both.

Markets Move, People Endure

Markets are fascinating to study. I’ve spent hours digging into sectors like broker connectivity and fintech infrastructure, trying to understand what felt like the most nuanced product-market fit. But the longer I’ve been in VC, the clearer it’s become that markets are fluid. They expand, contract, pivot, and sometimes vanish altogether.

What doesn’t change is how people respond when the market turns. Some founders freeze when conditions shift. Others adapt and use the turbulence as fuel. The best don’t just ride the wave. They build boats sturdy enough to weather storms.

I saw this firsthand working in municipal government through COVID. Overnight, the playbook went out the window. Budgets collapsed, businesses shut down, and citizens looked to leadership for stability. In those moments, it wasn’t about having the perfect policy on paper. It was about staying composed, communicating clearly, and finding solutions when none seemed obvious. Some leaders froze; others adapted. The ones who led effectively weren’t necessarily the most experienced, but the ones who had the grit to keep moving when the pressure mounted.

Venture works the same way. The founders worth betting on aren’t always in the hottest market. They’re the ones who steady the ship when the water gets rough, who don’t panic when deals stall, and who find another way forward when the first plan fails.

You can learn market dynamics from a book. You can model growth curves in a spreadsheet. But character under pressure? That’s something you only see in people. And in venture, that’s where the real bet is.

Learning Is the Real Job

Coming into VC, I didn’t have the traditional toolkit. I wasn’t a banker or consultant with years of deal experience. I had to build it on the fly, asking what felt like “basic” questions, poring over financials, and learning how to spot red flags in governance documents.

What surprised me most was how open people were if I just admitted I didn’t know something. Instead of pretending, I asked. Instead of assuming, I listened. Over time, the questions got sharper, the instincts more reliable, and the confidence more natural. What I thought was a weakness—starting from scratch—actually turned into a strength, because it forced me to approach everything with humility and curiosity.

It reminded me of law school. On day one, no one really knows how to read a case or think like a lawyer. You stumble through, you get cold-called, you second-guess yourself. But slowly, the repetition builds discipline. You learn to ask better questions, to analyze differently, and to see patterns where you once saw noise. Venture has been no different, just with higher stakes and a different set of textbooks.

The real job in VC isn’t about already having all the answers. It’s about building the discipline to keep learning. Markets change. Deal structures evolve. Technologies shift. If you think you’ve “arrived,” you’re already behind.

And this lesson applies far beyond venture. You can break into any field, whether it’s law, politics, or venture, if you stay curious, humble, and willing to learn. The technical knowledge will come. The mindset has to be there first.

The Human Side of Venture

Eighteen months into venture capital, the biggest lesson I’ve learned is that this work is far less about money than it is about people. Paperwork matters, but trust matters more. Markets shift, but character endures. Founders need more than capital—they need belief. And no matter where you start, the real job is to keep learning.

I came into this field with no traditional background. Athlete, politics, law student—nothing on my résumé said “venture capitalist.” But that turned out not to be a weakness. If anything, it made me approach the industry with fresh eyes and open ears. I’ve learned that you can break into any field if you’re willing to do the work, stay humble, and connect with people in a real way.

The technical side of venture—valuations, diligence, structures—can be taught. What makes the difference is showing up as someone others want to work with. Because in the end, the cap table tells you who owns what, but it doesn’t tell you who showed up when it mattered. And that’s the part people never forget.