Alone Together: The Story of Solo Venture Capitalists

This week’s episode is a little different. I sat down with my friend James Oliver Jr. , founder of Kabila, and this is one of the more honest conversations I’ve had on the podcast. James and I go back a bit. I had the chance to contribute a chapter to his book Burn Bright, Not Out , which focuses on founder mental health. That work is personal for him, and this conversation really shows why. We ta...

We’re back for Season 2 of Alone Together, and I could not think of a better guest to kick things off than Ben Freeberg of Oncology Ventures. Ben’s story is one of the most distinctive in venture. He started in finance and venture, was diagnosed with cancer at a young age, and turned that experience into a deeply personal investing mission. Today, through Oncology Ventures, he backs companies work...

“[My dad] took me down to Child Protective Services and dropped me off and said, you can't come home .… What it made me do was prove that he was fucking wrong about me.” To say I was floored by my conversation with Martin Tobias, founder of Incisive Ventures, would be a mild understatement. In this episode, Martin tells this traumatic story, and how that chip on his shoulder became fuel: from...

"I just keep showing more and more of me until they either invest or say no.” Banana Costume Fundraising Tips ... that was honestly what ChatGPT labeled the memory when I uploaded this podcast transcript, and I thought that was the absolute perfect name for this episode. I’ve admired Ethan Austin , founder of Outside Ventures , ever since I was his Lyft driver out of Camp Hustle. We had half...

What happens when a snowboarding VC does a podcast with a surfing VC?  I don’t have a good punchline, but it sure was an amazing conversation. I’ve admired John Gleeson, founder of Success VP, for a long while. He has taken an overlooked part of the ecosystem—founder-led customer success—and turned it into a powerful competitive edge. Just as I am obsessed with coaching, John is dedicated to empow...

“When people are around, things will be more okay.” In this heartfelt episode of Alone Together, I sit down with my good friend Mike MacCombie, founder and GP of Generous Ventures (disclosure: I am a very small LP in his fund). Mike opens up about the profound impact of losing his mom at age eight and how that formative experience shaped his unwavering commitment to building communities that ensur...

Patriotism isn't exactly a comfortable topic in venture. Faith often feels equally off-limits. But Andy Will—managing partner at Willpower VC—is unafraid to embrace both openly, believing deeply that venture capital can indeed be a fundamentally patriotic act. In this candid, thoughtful, and at times provocative conversation, Andy unpacks what patriotism means to him: not flag-waving or chest-...

"Algos scale. Artisans don't. But maybe that's the point." — Charles Hudson In this episode of Alone Together, I sit down with Charles Hudson—the OG solo GP, the founder of Precursor Ventures, and one of the most thoughtful voices in venture capital today. Initially, I invited Charles to talk specifically about supporting solo GPs and to share his stories and practical advice. Ho...

“Harlem is really who I am, my ethos .... and so when I was thinking about my fund, what inspired me, it's my roots." As a huge sports nerd and a New Yorker, I am so excited to bring you this chat with, Lorine Pendleton , founder and managing partner of 125 Ventures . In this episode of Alone Together, Lorine and we dive deep into her inspiring journey—from Harlem kid, watching Yankees ga...

“Don’t tell me 90% of the industry does it this way. I want to know what the 5% are doing—and why.” Those were the words of my good friend—and one of my very first compatriots in venture—Virginie Raphael, founder of FullCircle. In this episode of Alone Together, we explore her bold, refreshing take on raising a permanent (evergreen) fund, how her upbringing in France shaped her perspective on work...

"Holy S!#&! That's the model! That's what I've been looking for my whole life." Those were Nick Tippmann's exact words when he first discovered the world of startups and venture capital—and from that moment, everything changed. In this episode of Alone Together, I'm joined by my good friend Nick Tippmann, founder of TipTop Ventures. Nick has been one of my earlies...

This episode of  Alone Together  is  special —because when LPs ask me,  Who do you look up to as a solo GP? , my answer is  immediate :  Chingona Ventures . Samara Hernandez isn’t just one of the most impressive investors in the game—she’s been an inspiration, a blueprint, and, I’ll be honest, a bit of a North Star for me as I build Sidecut Ventures.  From the moment I started my journey, I’ve adm...

Summary For my very first podcast, I couldn’t think of a better guest than Kevin Moore. From the moment we met, I’ve always admired Kevin’s ability to see the world differently—and act on it. We’ve co-invested together (shoutout to SoLo Funds!) and bonded over our shared belief that the most successful ventures often start where others aren’t looking. In this conversation, we dive deep into what i...

Welcome to Alone Together , the podcast dedicated to the journey of solo General Partners (GPs) in venture capital. In this trailer episode, we introduce the mission of the show—deep, candid conversations with solo GPs who are navigating the challenges of raising, deploying, and managing funds on their own. What drives someone to go solo in VC? How do they build conviction, source deals, and scale...