Ever wonder what stand-up comedy and venture capital have in common? Both require guts, storytelling, and the ability to face rejection head-on. Whether you're delivering punchlines or pitching investments, success boils down to knowing your audience and perfecting your narrative. And just like a comedian, a first-time fund manager learns resilience the hard way—one silence or failed deal at a time

There was a time I seriously thought about trying stand-up comedy. I’ve always admired the guts it takes to get on stage with nothing but a mic, a few jokes, and the nerve to make a room full of strangers laugh. Recently, a few old friends of mine started hitting the open mic circuit, and watching them bomb and bounce back got me thinking—what is it about comedy that keeps people coming back for more, even after those painfully awkward silences? Why would anyone willingly put themselves in that position, hoping for laughs but bracing for dead air?

As I watched them struggle through their sets, it hit me: this isn’t all that different from what I do as a first-time, emerging fund manager. At first glance, stand-up and venture capital couldn’t seem further apart, but they have a lot more in common than you’d think. Both require insane amounts of risk, the ability to tell a story that resonates, and a talent for taking feedback (whether it’s audience silence or market rejection) and turning it into something better. Whether you’re testing jokes on stage or trying to convince investors to back your fund, success in both worlds depends on knowing your audience, constantly refining your approach, and—most importantly—mastering the art of the narrative.

The Art of Storytelling

For me, the storytelling part has always stood out. My mom is a few families removed from being a Navarrete, and I’ve been a fan of my distant cousin Rex Navarrete for over 20 years. If you don’t know Rex, he’s been a pioneer in the Filipino comedy scene since the early 2000s, touring the world, selling out shows, and putting out comedy albums. Growing up, I’d see my aunt (Tita Virgie) and Rex’s mom, Tita Goya, talking for hours over tea, while I’d hear about Rex’s latest performances. We even exchange messages now and then. During the 2000s, I got to introduce him as an emcee at festivals and shows—a definite highlight for me.

Rex is a master storyteller. He doesn’t just toss out punchlines; he pulls you into a world that feels both familiar and fresh. He brings his personal experiences, Filipino culture, and everyday struggles to life in a way that not only makes you laugh but also makes you feel like you’re part of the story. His ability to connect with his audience is unmatched. He knows exactly who they are, what makes them laugh, and how to keep them coming back for more.

That same storytelling ability is critical for a first-time fund manager. When you’re pitching to potential investors, it’s not just about the numbers or financial models. It’s about the story you’re telling—about where the market is going, why you’re the one to lead them there, and why your startups are the ones to bet on. Just like Rex pulls his audience in with a relatable narrative, a fund manager needs to create a story that makes investors lean forward, see the vision, and trust you’ll deliver. And, like Rex on stage, it’s often the strength of your story that determines whether you succeed or crash and burn.

Testing and Refining

Stand-up comedy is all about trial and error. Comics try out new bits in front of live audiences, and it’s the room’s reaction that tells them whether they’ve hit the mark. If the crowd laughs, great! But if the joke falls flat, back to the drawing board. Comics adjust the timing, rework the punchline, or scrap the joke altogether. It’s an ongoing process of testing, tweaking, and improving.

For a first-time fund manager, the process is similar. You start with an investment thesis—a hypothesis about a specific sector or type of founder you think will succeed. Then you test it. You make a few early investments, gather feedback, see how the market responds. If the initial investments don’t perform as expected, you pivot. Maybe you shift to a different sector, refine your strategy, or start targeting a different type of founder. Like a comedian fine-tuning a set, you’re constantly iterating, learning from failure, and adapting your approach.

In both worlds, resilience is everything. The ability to take feedback, whether it’s in the form of an audience not laughing or a market that doesn’t respond to your portfolio, and keep going is what separates those who make it from those who don’t.

Segmentation and Knowing Your Audience

One of the biggest lessons in both stand-up and venture capital is this: not everyone is your audience. Rex knows his core crowd—Filipino communities—and his stories are tailored to them. His jokes about growing up with immigrant parents, eating Spam, and navigating Filipino family dynamics hit hard because they resonate so deeply. But his humor also crosses boundaries and connects with a broader audience because it’s grounded in real, human experiences.

A fund manager has to know their audience in much the same way. You can’t just invest in every startup that crosses your path. The best fund managers know how to segment the market, focusing on founders and sectors that align with their expertise and values. If your focus is on diverse, mission-driven founders, stick to that. Over time, you refine your approach, learning which sectors perform best for your fund and which founders are the best fit—just like a comic knows which jokes land with their crowd.

The Differences: Risk and Feedback

But there are some important differences. The stakes for a first-time fund manager are often much higher than for a comedian. If a comic bombs on stage, it hurts, but they can always tweak the material and try again the next night. For a fund manager, the consequences of a bad investment are far more significant. You’re managing other people’s money, and one wrong move can do serious damage—not just financially, but to your reputation.

And while comedians get immediate feedback (either the room laughs or it doesn’t), fund managers are often working with a delayed timeline. It could take years to know whether your investments pay off. That requires a whole different level of patience and long-term thinking. In both cases, though, you have to learn to handle uncertainty and keep pushing forward even when things don’t go as planned.

Resilience and Adaptability

Whether you’re on stage with a microphone or sitting across from investors with a pitch deck, resilience is the name of the game. Comedians deal with constant rejection—whether it’s hecklers, silence, or worse, indifference. Fund managers face their own hurdles—investors who pass on their fund, founders who turn down offers, or deals that fall apart. In both worlds, you have to learn to roll with the punches, adapt, and keep going. It’s the only way to survive.

The Punchline

After watching my friends test out their stand-up chops, I’ve realized: bombing in front of investors is tough, but bombing in front of a room full of strangers is brutal. At least when a startup doesn’t perform, no one’s booing you off the stage. Then again, maybe the venture world could use a few hecklers—it might speed up the due diligence process and cut down on bad pitches!

So, whether you’re delivering a punchline or pitching a new fund, it all comes down to knowing your audience, telling a killer story, and refining your craft through trial and error. Both comedians and fund managers need resilience, adaptability, and the ability to connect with the right people at the right time. And in both worlds, the risks may be high—but the rewards are definitely worth it.

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In both stand-up comedy and venture fund management, success requires more than just skill—it’s about resilience, storytelling, and the courage to keep pushing forward, even when the audience (or market) doesn’t respond. Whether you're delivering a punchline or a pitch, it’s the ability to adapt, connect with your audience, and learn from setbacks that sets you apart.

And who knows—maybe next year, Rex will bring his talent to the University of San Francisco’s campus, and I might even step back into the spotlight myself as an emcee. After all, whether on stage or in the boardroom, the show must go on.

xxoo,

Maximillian Diez

GP, Twenty Five Ventures

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