Raising at Racecar Speeds: My Conversation with Greg Mark
Anyone who’s been through the grind of raising capital knows that fundraising isn’t just a transaction—it’s a relationship, a process, and, as I learned from this week’s guest on Raiser’s Edge, sometimes it’s an F1 race. Greg Mark, founder of Markforged and Backflip, is an extraordinary fundraiser. He has raised over $550M, and piloted his companies through public markets, industry crashes, and moments of breakneck success (and near-total disaster).
In our discussion, Greg revealed his radically strategic approach to fundraising—and how having survived the hard times where he had to be “a stone cold killer” allows him to look back with wisdom, empathy, and humility now.
Here are some of the insights from my conversation with Greg:
1. Fundraising Is a Race—And You’re the Driver
Greg compares founders to Formula 1 drivers—coming into corners at life-or-death speed, with only seconds to make decisions. And that speed and control also extends to the raise. He taught me the value of going all in when you’re raising: compress your raise into just two or three weeks of focused, relentless momentum. If you try to stretch a raise out over months, you lose that heat and urgent energy that makes investors lean in, and you waste valuable time that should be focused on building and strengthening the business. Greg lines up all his meetings for a tight window, not just for efficiency—but because that’s the only way you turn a spark into a fire.
2. You’re Not Selling an Egg. You’re Selling the Golden Goose.
One of my favorite analogies from Greg: your investors aren’t buying a golden egg - they’re buying the golden goose. Founders often obsess about the brilliance of their product—the “egg”—when investors are buying a system, a team, a company, a way to repeatedly produce outcomes—the “goose.” In his pitches, Greg reframes his founder story, his team, and his company as a machine that creates great products, shifting from “here’s what I built” to “here’s the engine I built for creating value—again and again.” That’s the insight investors actually bet their careers on – and it tells a story of repeatability that makes the founder themselves backable.
3. The Most Expensive Mistake Is Choosing the Wrong Investor
Greg has lived both the pain of “painfully dilutive” rounds, and the pain of choosing the wrong board members for his companies. His lesson: it’s always worth a compromise on valuation to bring in the right investor. You’re not just picking a check—you’re picking a co-pilot for the wildest ride of your life. Optimize for alignment and trust as the first priority.
4. Hard Work Now Allows Empathy Later
Greg’s final wisdom is as honest as it gets: Early on, you need to be tough, compartmentalize, and protect your company’s future at all costs. But as you grow, your effectiveness as a leader—and fundraiser—comes down to your ability to empathize with your colleagues and investors who took the journey with you. After years in the trenches, Greg has learned that the people matter more than the products - and that empathy makes him a better fundraiser.
Greg’s playbook is a reminder: capital advantage comes not from a magic phrase or pitch deck template, but from the relentless practice of being focused, being relentless, and caring about every relationship—not just the outcome they produce.
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Stay sharp,
Ben