This isn’t the first time we’ve sat down with Matt McDonnell. We first crossed paths in "Navigating Complexities," where we traced parts of his story through seas of introspection and adventure—an accumulation of pivots and internal realignments that only resemble instinct in hindsight.
Like many stories, it began with a kid in a small town—watching his mom hold the family together, feeling the quiet weight of ambition before he knew its name, and carrying questions he hadn’t yet learned to ask.
What does it mean to be a man? What does it mean to be whole?
In the early chapters, he thought the answers might be found in sports. Then academics. Then the pressure cooker of private equity. But no title gave him what he really wanted: peace.
Then came sailing.
Not metaphorically—literally. He was building a career in professional sailing, chasing wind across oceans, pushing his limits at sea. There’s clarity in open water, but also isolation. And eventually, Matt realized he was steering toward a life that looked impressive from the outside but felt hollow within.
He stepped away. Not because he failed, but because he listened. And in doing so, he made space for something else to emerge.
Today, he’s an investor. A partner. A voice behind founders who are often still trying to find their own.
The pattern changed when he finally stopped to ask:
What do I actually value?
Do you remember the first time you asked yourself that question?
Take a moment—ask it again. As it changed?
For Matt, that question opened the door to a journey that looked less like a ladder—and more like a compass pointing him towards people.
Not just backing them with capital, but with belief. With patience. With presence.
Matt talks about investing not as a transaction but as a relationship. One that requires just as much personal evolution as professional skill. He doesn’t want to work with founders who have it all figured out. He wants to walk alongside the ones who are willing to ask better questions.
And that requires a lot of unlearning. About masculinity. About success. About the false certainty we wrap around ourselves to feel safe.
He speaks to the generation coming up now—the Gen Z’ers raised on algorithms and always-on ambition. He reminds them that self-awareness isn’t fluff; it’s strategy. That presence is a muscle. That purpose isn’t found—it’s built.
Matt didn’t arrive at these insights quickly. Or neatly. Or without pain. But he kept going. Kept paying attention.
And now, he helps others do the same.
Because at some point, we all discover the map we were handed doesn’t match the terrain.
And that’s when the real journey begins.
Listen to Matt's story on Uncharted Your Sidekick For Life Podcast
Matt McDonnell is the Co-founder and Managing Partner of Stellifi Venture Capital, where he invests in early-stage PropTech and ConTech startups. A former pro sailor turned entrepreneur and investor, Matt also co-founded The Geyser Group and previously worked with Notley, Springdale Ventures, and Famigo. He teaches at Acton School of Business, guest lectures at UT Austin, and supports the arts and education through various nonprofits. Matt holds a J.D., an MBA (Valedictorian), and a B.A. in Philosophy—and splits his time between Austin and Steamboat Springs with his family.
Natalie Peyton studied theatre and film in Australia, New York and LA and performed stand-up on the “three coasts.” She honed her podcast executive skills over the last 4 years developing and producing dozens of podcasts and even hosts a children’s mindfulness bedtime program
Leon Vanstone: Leon brings his curiosity and sharp interviewing skills to the table, facilitating insightful discussions with our mentors, extracting valuable lessons and insights to empower listeners on their own path to growth and achievement.
Dan Dillard: Dan, with his thoughtful approach and engaging style, delves into the minds of our mentors on the podcast, crafting compelling interviews that uncover the wisdom and experiences driving their success and impact.
This blog was written by Anais Schmidt, one of the hosts of the Uncharted Podcast. Anais is also an aspiring musician. When not in her studio, she tours Europe with Monte Mai.
If you would like to join the conversation email us at anais@foundingup.com
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