From Immigrant's Son to Venture Capital: Max Diez's Journey and Lessons for the Next Generation of Entrepreneurs
In our entrepreneurship and innovation class at Meredith College, we recently had the privilege of hosting Maximillian Diez, founder of Twenty Five Ventures and the 25V Diversity Fund. Max's journey from the son of an immigrant to a successful venture capitalist offers powerful insights for aspiring entrepreneurs, particularly those from underrepresented backgrounds.
"Don't be afraid to start small. It's okay if you start small—only great things will happen. And I always say to people that start small, there's only one way up, right? If you're already super small, the growth to get to medium and get to large is only a short few jumps."
-Max Diez
An Unexpected Path
Max's story is not one of privilege or predetermined success. Growing up as the child of immigrants who came to America in the 1960s pursuing the American dream, Max took the bus "like anybody else" and watched his parents work multiple jobs to make ends meet. As the oldest child in his family, he balanced responsibilities at home while working 20 hours a week as a high school sophomore, commuting 22 miles to school, and still finding time for sports.
What's remarkable about Max's journey is how unplanned his path to success was. After high school, without plans for college, a chance meeting with an older attorney who saw potential in him changed everything. This mentor relationship (which Max compared to the book "Tuesdays with Morrie") led to his first opportunity to manage investments—turning $1.5 million into $3.1 million and setting him on a path toward finance and entrepreneurship.
As Max reflected, "If you were going to say to me, this is where my life would have been... back when I finished high school in 1995, knowing that I wasn't going to college, I would have said you were obviously dreaming."
The Evolution of an Investor
Max's career has included being an early employee at Redfin.com (which went public), founding UpNest (which he sold to Realtor.com in 2022), and acquiring and selling Movoto.com. These experiences gave him valuable insights into what makes businesses succeed.
What struck me most was how Max's personal experiences shaped his investment philosophy. Standing at around 5'6", Max noted he was always conscious of his height in business settings. During the pandemic, when meetings moved online, he realized "nobody cared how tall I was when I was sitting across from them," which helped him expand his network beyond what might have been possible in traditional settings.
This experience directly influenced his desire to create the 25V Diversity Fund, focusing on underrepresented founders including Black, Latinx, and female entrepreneurs. Max explained that he saw tremendous talent in diverse founders who weren't getting funding, which represented both a moral imperative and a market opportunity.
What Max Looks for in Founders
For students considering entrepreneurship, Max offered clear insights into what he looks for when investing:
Grit and Character: "I look for founders that have a little bit of grit, have a little bit of tenacity, have a little bit of fire in their belly, have a little bit of character, because I think that matters."
Subject Matter Expertise: "You have to have somebody that knows a little bit of what you're doing."
Clear Vision: Founders need to articulate exactly what they want to build, which comes from experience and understanding the industry.
Metrics and Management: How many users do you have? How much revenue? How well have you managed available resources?
The X-Factor: What makes you different? When Max asks founders "Why you?" he's looking for high conviction—do they truly believe they're the right person to solve this particular problem?
Practical Advice for Young Entrepreneurs
Max shared several practical insights that resonated strongly:
Capital Efficiency Matters: He cited examples of companies that raised millions but burned through cash without building viable businesses. For service-based businesses especially, bootstrapping is often the better path.
Daily Improvement Compounds: "If there's one thing that you take away from this talk today, it's just be comfortable challenging yourself and think about how you can improve your business or your idea even a small percentage each day... whether that means connecting with someone on LinkedIn... or doing more research on a specific topic. All of those incremental improvements will only help your chances of being successful."
Leverage Technology: When discussing contracts and legal matters, Max emphasized how technologies like ChatGPT have democratized access to knowledge that once required expensive experts.
Find Your Community: "Build your crew, your community. Find some people that believe in you," Max advised, noting that these relationships provide crucial support on the entrepreneurial journey.
A Message for Women in Business
Speaking directly to our class at Meredith College, Max emphasized that for too long, women have been pushed aside in financial management and business leadership. He encouraged students to take advantage of the opportunities created by technology, regardless of external factors in the world.
His final advice was particularly powerful: "Don't be afraid to start small. It's okay if you start small—only great things will happen. And I always say to people that start small, there's only one way up, right? If you're already super small, the growth to get to medium and get to large is only a short few jumps."
The Impact of Representation
What makes Max's work through the 25V Diversity Fund particularly meaningful is his focus on wealth creation for underrepresented communities. By focusing on PropTech (property technology) and FinTech (financial technology), his investments touch two areas that directly impact household wealth—housing and financial management.
As we wrapped up our session, Max highlighted that beyond investing, one of his fund's most significant impacts is accessibility. Twenty years ago, underrepresented founders wouldn't have had access to venture capitalists willing to take a 15-minute call to discuss an idea. By creating those pathways and educating the next generation of entrepreneurs, Max is working to ensure that talent and innovation can emerge from all communities.
Max Diez's journey reminds us that entrepreneurial success doesn't always follow a predictable path. His commitment to supporting diverse founders, emphasis on capital efficiency, and belief in incremental improvement offer valuable lessons for anyone charting their entrepreneurial course.
Perhaps most importantly, his story demonstrates the power of authentic relationship-building in business. As he noted about our work together, "Sometimes you just never know where a relationship will evolve." Our professional relationship began with a branding project and evolved into a board position and friendship.
That lesson—that connections built on trust and mutual respect become the foundation for future opportunities—may be the most valuable insight from his talk. Success isn't just about the business plan or funding strategy, but about the genuine relationships we build along the way.
Maximillian Diez is the founder of Twenty Five Ventures and the 25V Diversity Fund, focusing on investing in underrepresented founders in the PropTech and FinTech sectors. With over two decades of experience in finance and technology, including multiple successful company exits, Max leverages his background as the son of immigrants to create opportunities for diverse entrepreneurs while serving on the Board of Trustees at his alma mater.