We launched Hyperplane in early 2015 with two founding convictions: pre-seed and seed would become institutional financing rounds and artificial intelligence was ready for real-world applications.
In 2015, U.S.-based venture capital firms managed roughly $400 billion in assets which grew to $1.4 trillion by the end of 2024. The number of full-time tech investors swelled from approximately 8,000 to over 30,000 in the same period. In 2015, the “Magnificent Seven” combined market cap stood at $1.7 trillion compared to $17 trillion by the end of 2024. Nvidia’s market cap was a mere $11 billion—yes, $11 billion—versus over $3 trillion a decade later and one of the biggest hurdles raising Fund I was “What’s AI?”. Podcasts and blogs such as OpenLP, Invest Like the Best, Venture Unlocked, and other invaluable resources for emerging managers didn’t exist. Apart from my co-founder John Murphy, we were all new to venture investing; in fact, I started speaking English only 10 years before my first tech investment in 2013 where John and I initially met. We learned on the fly, got lucky with our early mentors and LPs, and relied on our hustle and relentless determination to pursue and invest around our founding convictions.
Ten years later, we’ve deployed over $100 million in 72 companies—including six new investments in 2024—with these portfolio companies collectively raising over $1 billion in follow-on funding and achieving 18 exits for a total exit value exceeding $825 million.
As we celebrate and look back at our first decade, we’re deeply grateful for the support of our LPs, founders, and community who bet on us in the early days. We wanted to share some key lessons learned—and where we’ve stumbled—while building our firm from the ground up.
1. Culture is the Foundation
We win our most competitive deals because founders vouch for us. While our track record and domain expertise open doors, our culture is our greatest edge. We operate like a startup, fueled by hustle, grit, and an underdog mindset. As founders first, we bring empathy, curiosity, and tenacity. Our offsites aren’t just about celebrating wins; we dissect mistakes, challenge assumptions, and refine our approach. We invest most of our “building” energy in helping each other succeed, knowing this drives long-term returns and strong partnerships. For a decade, our brutally honest and direct quarterly Roast & Toast dinners have kept us grounded while sparking personal and professional growth. Culture isn’t hired—it’s forged. We can’t overstate this enough to new managers and founders: your culture journey must begin on day one.
2. High Ownership and Selective Follow-On
In a power-law world, prioritize high ownership early—even if it means delaying investing after your first close. Pair this with a disciplined, milestone-driven follow-on framework where metrics—not syndicates or gut feelings—guide decisions. Venture capital blends art and science; neglecting the science—waterfalls, dilution, and process—from day one can turn strong picks into losses.
3. Post-Investment: Solve the Hardest Problems First
At seed stage, we’ve seen time and again that sales and culture are the toughest—and most critical—challenges and where we focus first. Sales is the lifeblood—revenue validates your idea and fuels growth. Building product in a vacuum, without customer feedback or market traction, risks wasting time and money. On the flip side, culture is the glue—it keeps your team motivated, aligned, and resilient through the inevitable ups and downs. A mission-driven culture with openness and a hunger to win isn’t just feel-good stuff; it’s a practical edge for hiring top talent and outlasting competitors.
4. Focus on Process, Not the Outcome
We started as dreamers, fixated on the distant impact of our companies’ products. We’ve learned that great outcomes come from consistently executing the small stuff. Success hinges on robust processes—structured follow-on decisions, proactive post-investment support, and engaged board work. Founders are the visionaries; we focus on the present to help them execute and grow.
5. Geography Matters
Boston offers founders a top-tier ecosystem—elite universities, groundbreaking research, and abundant talent—but scaling a tech startup outside Silicon Valley or New York is more challenging on many levels. Boston has incredible founders starting more consequential companies than ever, with strong advantages for AI’s second and third innings, though speed to market and financing risks remain high. Early on, we overcommitted to one geography, betting on Boston’s early AI potential. We were wrong. From those hard-earned lessons, we’ve forged a framework guiding every investment we make outside the Bay Area and New York to drive success.
6. Founder-Problem Fit
From the start, we chose to back vertical AI companies—those building end-to-end solutions, often integrating hardware, targeting specific, high-stakes enterprise or industrial challenges. In vertical AI, market dynamics are everything. A stellar founder in a bad market will struggle. A stellar founder in a great market—that’s the magic. For founders, we’re drawn to ambition, grit, curiosity, self-awareness, energy, and an unrelenting obsession with the problem they’re solving. We can’t overstate obsession—it’s the fuel for building iconic companies. We’re obsessed with finding founder-problem fit: a deep, instinctive alignment with the challenge at hand.
7. Failure
For founders, failure is the ultimate nightmare. For early-stage investors, it’s a constant companion, built into the system and also the source of your deepest lessons. Building a seed-stage venture firm from scratch is an incredibly humbling journey, and humility becomes your greatest strength. Not every entrepreneur thrives as an investor and not every investor thrives as an entrepreneur. But to forge a lasting firm that you can one day hand to the next generation—we believe you need both.
8. Hustle & Patience
One of the biggest mistakes we’ve observed—and one of the most valuable lessons we’ve learned—is how other GPs often pit hustle and patience against each other, abandoning companies that don’t “pop” quickly. In our view, persistent hustle and patience are not opposites but perfect complements. Some of our most successful portfolio companies today are those where we’ve gone against the herd, stepped in when impatient capital bailed, and partnered closely with founders through rough patches—one such company has generated over 70x returns and continues to grow. Clear milestones guide our follow-on investments, but pragmatism and flexibility remain essential.
9. Be Prepared for Cycles
Venture runs on boom-bust cycles with sharp drops from every peak. In ten years at Hyperplane, we’ve faced three hype waves, a global pandemic, and a macro downturn. We slowed investing drastically in the 2020 – 2022 frenzy when valuations and speed defied gravity laws. Don’t lose sight of the big picture and fundamentals—we’re here for the long-term. Timing and strategy for bulls and bears are non-negotiable—too much, too fast spells trouble. Discipline, particularly deployment discipline, is vital.
10. EQ > IQ
Smarts matter, but empathy and intuition win when the future’s still foggy. In early-stage investing, emotional intelligence often trumps raw intellect because pre-seed and seed is less about crunching numbers and more about navigating people and uncertainty. Startups at this phase are chaotic, unproven, and driven by founders’ vision and grit. IQ can analyze a spreadsheet, but EQ reads the room—sizing up a founder’s resilience, adaptability, and ability to inspire a team through the inevitable ups and downs. Markets shift, tech evolves, and plans fail—EQ spots the human signals that predict who’ll persevere.
Life Starts At Ten
An LP recently told us at our annual meeting, “Life starts at ten.” We see it, and in many ways we believe we’re just getting started. In the first 10 years, your first fund fully matures, you weather hype and macro cycles, and navigate team growth and change. The true win lies in adapting to an ever-faster changing world and discovering who you are—and aren’t—as a firm. Venture’s a long game; ten years is just the starting line.
