jurgen van de Vyver - launchpad capital

“After more than 160 job rejections, I learned that success often boils down to resilience and resourcefulness.”

February 19, 2025

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In a venture landscape often constrained by pedigree and insular networks, this week’s featured investor stands out for their grit and determination—160 job rejections did not derail Jurgen’s resolve.

That spirit not only defines his journey but also shapes his investment ethos: bet on founders who may not fit the traditional mold but possess the resilience to thrive when the odds seem stacked against them.

Why should you care? 

Because this is precisely the kind of underdog story that embodies the new wave of venture capital: nimble, daring investors who don’t just follow the pack but chart their own paths. 

It’s a mindset that recognizes talent and grit over “perfect” résumés—opening the door to transformative ideas that might otherwise go overlooked. At VC Uncovered, we believe this approach is the future of venture, reflecting our manifesto’s call for bold risk-taking, diverse perspectives, and active partnerships that do more than just write checks.

If you’ve ever felt “outside” of the venture bubble or wondered how to break in without a famous last name or Ivy League degree, this story proves that perseverance and authenticity can reshape your trajectory—and maybe even the trajectory of entire industries.

Meet Jurgen

Q: You’re in a city, eating, drinking, and reading something. What is it?

A: Cape Town, Aperol Spritz and doom scrolling X to make sure I don't miss anything in the US :)

“After more than 160 job rejections, I learned that success often boils down to resilience and resourcefulness.”

“Lightning doesn’t always strike twice. Each opportunity must be judged on its own merits.”

“We get paid to say no—don’t fall in love with deals.”

“Never rush diligence, even in a ‘hot deal.’ No amount of FOMO replaces real understanding.”

“VCs often only truly see the vision once exceptional founders lay it out for them.”

Original Responses (Lightly Edited for Clarity and Flow)

Background and Personal Journey

Experiences Shaping My Investment Approach
My approach to investing today is deeply influenced by my personal journey, which taught me to value resilience and adaptability in founders. I look for people who show grit and find ways to “zig” when life “zags.”

In 2015, I came to the U.S. for a six-month secondment with every intention of returning to South Africa, where my professional path was already laid out. However, after going back home, I realized I wanted to challenge myself and pursue something bigger. Coming back to the U.S. was a leap into the unknown. The next two and a half years were tough—my background and education weren’t easily recognized or transferable for venture or finance roles in the U.S., which was the field I aspired to break into.

After relentless hustling, networking, and more than 160 job rejections, I applied for a venture analyst role and noticed a portfolio company whose founder I had briefly met. That connection led to an introduction to one of the firm’s partners, who, like me, was from South Africa. He understood my story, determination, and potential and ultimately gave me the opportunity to run finance and operations. Working with a small team taught me how to manage a venture fund’s operations and evaluate companies effectively, and ultimately equipped me with the foundational tools for investing from 2021 onward.

This experience shaped my belief in identifying underdogs—those who punch above their weight, overcome immense challenges, and dare to aim big. It’s this mindset that guides how I approach investing today.

Moment Inspiring Venture Capital Career
There wasn’t a single defining moment, but I always envisioned myself doing something in finance. Once I experienced the thrill of making my first investment, I knew this was the path for me. The idea of investing in exceptional people with bold ambitions, working alongside them, and contributing in some way—even if it’s simply as a sounding board—was incredibly fulfilling. Seeing them progress from point A to point B and knowing I played a small part in that journey is what makes going to work so rewarding.

Influences on My Worldview
From a personal standpoint, my parents have had the most significant influence on my worldview. They were the perfect yin-yang in my life—my mom was my biggest supporter and the backbone I leaned on during tough times, while my dad never accepted excuses for failure and always pushed me to do better. Together, they created a powerful balance that shaped who I am today.

Professionally, my brother played a significant role in my earlier years, but without a doubt, my partner, Ryan Gilbert, has had the most profound impact on my career. I’ve been fortunate to work alongside him to this day, and I’ve learned too many lessons from him to list. Having him as both a mentor and a partner has been an invaluable privilege that continues to shape how I approach decision-making.

Unconventional Belief
I have two unconventional beliefs that shape how I assess opportunities:

  1. Lightning doesn’t always strike twice. Founders who achieved great outcomes in the past don’t necessarily replicate that success in their next venture. Each opportunity must be evaluated on merits rather than on past achievements.

  2. Never rush diligence, even in a ‘hot deal.’ Just because a deal is oversubscribed or backed by tier-1 VCs doesn’t mean it’s a sure thing. Relying solely on external judgments can lead to overlooking critical risks—and we’ve seen far too many examples where that approach hasn’t ended well.

Balancing Intuition with Data
For me, it’s about recognizing the strengths and limits of both. Coming from an analytical background, relying on data feels natural—it’s part of how I’m wired. That said, I deeply value intuition, especially in the early stages of a company when data is often sparse or unreliable. At that stage, the investment is really about the founder, their vision, and their ability to navigate uncertainty.

Best Advice Received
The best advice I’ve received, specifically pertaining to venture capital, is, “We get paid to say no—don’t fall in love with deals.” While it’s tongue-in-cheek, the underlying principle has always stuck with me. It reminds me to stay objective and avoid letting initial excitement cloud my judgment. Rather than seeking information confirming my enthusiasm, I also focus on what I might be missing: “What am I not seeing?”

Philosophy and Insights

Investment Philosophy
I focus on investing in founders with grit, adaptability, and a clear vision for solving meaningful problems. I ensure a strong alignment between their ambition and the market opportunity. This approach comes from my personal experiences navigating uncertainty, where resilience and the ability to pivot were key to overcoming challenges.

Values When Working with Founders
When working with founders, I ask myself two key questions: “Can I trust this person?” and “Is there a clear path to a true partnership?” Those are my top priorities. At the end of the day, I’m investing not just in the business but in the people driving it. To overcome challenges, we need to align on goals, communicate openly, and collaborate effectively.

The Perfect Founder Pitch
I want to see a strong opportunity with significant upside potential and a clear path to scaling. That includes a well-defined distribution strategy—such as partnerships with aligned, enthusiastic players—that can accelerate growth beyond a labor-intensive, one-by-one approach. Ideally, the pitch would show initial traction, proving that the product works and that new capital will fuel acceleration rather than provide more runway to “figure things out.”

The team should also understand their market deeply and articulate how they’re uniquely positioned to win. Most importantly, I look for founders who are experts in their space and can be great partners—people I can trust and collaborate with to navigate challenges and maximize opportunities.

Approach to Risk
It comes down to the risk I can live with. I used to focus heavily on mitigating the downside, but over time, I’ve recognized that risk is inherent in uncovering outsized opportunities. Now, I weigh potential upside against the type of risk I can tolerate rather than trying to eliminate risk.

Measuring Success Beyond Returns
I look at the relationships I build and my personal growth. You end up sharing the stress and the successes with founders; while I’m not in their shoes, I’m still deeply invested in their journey. On a personal level, I can see how much I’ve grown professionally over the years—recognizing moments where I could have handled challenges differently and improving over time. That sense of continuous evolution is hugely rewarding.

Exciting Trends and Technologies
AI remains exciting; we see breakthroughs almost daily. However, as a fintech investor, I’m most interested in bridging the gap between cutting-edge innovations and the slower-moving, highly regulated institutions that dominate the finance industry. Traditional financial institutions often lag in adopting new technology at scale. The real opportunity is in companies that can build that bridge—helping institutions leverage AI effectively while navigating legacy systems and regulatory complexities. Those companies will play a critical role in shaping the next era of innovation.

Misconception About VCs
VCs know exactly what they’re looking for and are just waiting for the right company to come along. In reality, I believe more than 90% of VCs only see the vision once truly exceptional founders lay it out for them. The founders often drive innovation and show what’s possible, rather than VCs predicting it in advance.

Improving the VC Ecosystem
I’d address the unwritten culture of who’s “in” and who’s “out.” There’s a pervasive assumption that only certain types of people—those with specific pedigrees or networks—can build successful businesses. This notion creates unnecessary gatekeeping, excluding talented founders from different backgrounds.

Time and again, I’ve seen great businesses built by people who took unconventional paths. By breaking these biases and making the ecosystem accessible to a broader range of talent, we can achieve more innovation, diversity, and, ultimately, better outcomes. Venture capital thrives when it bets on potential rather than pedigree, and shifting this mindset would strengthen the entire ecosystem.

Challenges for Early-Stage Founders
Bad advice from early backers who speak in generalities. Often, founders operate under assumptions that might seem logical but prove disastrous as they near the end of their runway. Unfortunately, the people giving the advice rarely face the consequences, leaving founders to bear the fallout alone.

VCs can address this by offering tailored, context-specific guidance rather than one-size-fits-all advice. Every startup is unique, and VCs should invest the time to understand a founder’s vision, market dynamics, and particular challenges before giving recommendations.