Alone Together: The Story of Solo Venture Capitalists

Burn Bright, Not Out: James Oliver on Venture, Mental Health, and Knowing When to Stop | Alone Together | S2E2

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 talk about his journey from building startups to raising a fund, and ultimately making the decision to pause that fundraise. Not because he couldn’t do it. Not because the opportunity wasn’t there. But because he could feel what it was doing to him. That’s not a story we hear often in venture. We spend a lot of time talking about pushing through. This is a conversation about knowing when not to. We get into: * Why founder mental health became James’s life’s work * The reality that none of it is personal, and all of it is personal at the same time * The emotional weight of raising a fund as a solo GP * The added burden many overlooked founders and managers carry * And what it looks like to choose the long game over short-term validation There’s a moment where we talk about the paradox: You are your startup. You are not your startup. Holding both of those at the same time is hard. And most people don’t talk about it. For me, this episode is a reminder that venture is still a people business. If we care about outcomes, we should care about the people doing the building. Not every GP story ends in a fund. Some of them pause. Some of them redirect. Some of them choose to protect something more important. Really grateful to James for coming on and being as open as he was. 00:00 – Intro and why this conversation matters Why this episode feels different and why James was the right person to have it with 02:00 – The origin story: startup failure and mental health James shares the story of his first company, personal challenges, and how that shaped his focus on mental health 08:30 – Founder mental health is not theoretical The reality behind the “72% of founders struggle” stat and why most people still don’t talk about it 14:00 – “You are your startup. You are not your startup.” The paradox every founder and GP lives with and why it’s harder than it sounds 19:30 – The GP journey and the weight of fundraising What it actually feels like to raise a fund as a solo GP and hear “no” repeatedly 24:00 – The decision to pause Kabila Ventures Recognizing the signs, protecting mental health, and choosing to stop before it becomes destructive 29:30 – Overlooked founders and invisible pressure Why some founders and emerging managers carry a heavier burden and how that impacts mental health 34:30 – Therapy, self-awareness, and doing something Practical ways founders can start taking care of their mental health without overcomplicating it 39:00 – Burn Bright, Not Out and the broader mission The book, the nonprofit, and why this is bigger than one conversation 43:00 – What comes next James on the long game, returning to venture when the time is right, and building sustainably Chapter Notes

Turning Cancer into Comedy & Conviction w/ Ben Freeberg & Oncology Ventures | Alone Together | S2E1

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 working to improve cancer care now, not in theory, not someday, but in ways that can make a difference for patients and providers in the near term. But this conversation is about more than fund strategy. Ben and I talk about the strange, human, very non-linear path that leads someone to build a fund around lived experience. We talk about what the healthcare system still misses, why emotion actually matters in venture, how authenticity beats performance in fundraising, and why Ben ended up using comedy as a way to process one of the hardest experiences of his life. This one felt like the right way to start the season because it gets at what this show is really about: the human side of building something meaningful in a business that often pretends to be all spreadsheets and certainty. What We Talk About • Ben’s path from banking and venture to launching Oncology Ventures • How his cancer diagnosis reshaped his sense of purpose • The real gaps in cancer care beyond drug development • Why early detection, navigation, and better incentives matter so much • How comedy became part of Ben’s healing process • The difference between genuine founder connection and manufactured storytelling • Why solo GP life is hard, communal, and often misunderstood • The role emotion plays in both fundraising and investing Why This Episode Matters There are a lot of people in venture who can talk about markets. Fewer can talk honestly about why they do the work in the first place. Ben is one of those rare people whose fund strategy, personal story, and operating philosophy actually line up. He is serious about outcomes, serious about building, and refreshingly unpretentious about the fact that this work is emotional, messy, and deeply human. For LPs, this episode is a reminder that the best emerging managers are not just assembling portfolios. They are often building from lived conviction. For founders, it is a masterclass in why authenticity travels further than performance. And for fellow solo GPs, it is a good reminder that despite the label, none of us are really doing this alone. Notable Quotes “Good luck to someone else trying to do this in a more genuine way.” “If that’s not funny, then this is going to be really, really difficult.” “People are literally dying today because of perverse incentive structures, lack of interoperability, and stuff that is so fixable.” Chapter Markers 00:00 [https://www.youtube.com/watch?v=EX_VqeG1xoE] Welcome back to Alone Together and Season 2 kickoff 01:00 [https://www.youtube.com/watch?v=EX_VqeG1xoE&t=60s] Ben’s background and the origin of Oncology Ventures 08:30 [https://www.youtube.com/watch?v=EX_VqeG1xoE&t=510s] What the cancer care system is still getting wrong 13:15 [https://www.youtube.com/watch?v=EX_VqeG1xoE&t=795s] Cancer and comedy, and why humor mattered 19:45 [https://www.youtube.com/watch?v=EX_VqeG1xoE&t=1185s] Selling yourself as a solo GP without overperforming 25:00 [https://www.youtube.com/watch?v=EX_VqeG1xoE&t=1500s] Emotion, fundraising, and the reality of venture 33:00 [https://www.youtube.com/watch?v=EX_VqeG1xoE&t=1980s] The solo GP myth and what support really looks like 38:30 [https://www.youtube.com/watch?v=EX_VqeG1xoE&t=2310s] How emotion can actually sharpen investment judgment 47:30 [https://www.youtube.com/watch?v=EX_VqeG1xoE&t=2850s] Fast Four: best day, worst day, shoutout, and legacy

“You Can’t Come Home” with Martin Tobias from Incisive Ventures | Alone Together | Ep. 11

“[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 teenage exile → Microsoft manager → IPO → prolific VC. But this isn’t a fund-size story. It’s about what trauma does to us, why proving someone wrong only carries you so far, and how to find meaning after you already “won. ”We covered poker, tacos, watches, and girl-dad life — many things we both love and share. But what stuck with me most is Martin’s honesty about the full arc: from son, to entrepreneur, to VC, and back to father. For founders, LPs, or anyone who still thinks success is a straight line, Martin’s story is a reminder: resilience is forged in pain, but sustained by curiosity and craft. In this episode Martin and I dig into: 🚪 Getting kicked out at 16 and why chips on your shoulder put chips in your pocket. 🎲 Why poker is the best diligence tool for founders (and how CEOs vs. CFOs play differently). 🕰️ Watches, tacos, and the craftsmanship test for founders. 👨‍👧‍👧 Girl-dad stories and what parenting teaches us about investing (and vice versa) .🌊 Surfing, longevity, and finding joy after you’ve already “made it.” 💸 The worst days in venture — and why dishonesty is the true deal-killer. Martin’s vulnerability surprised me, and I think it will surprise you too. Chapters 00:00 “You can’t come home” — teenage exile as fuel 04:33 Why Martin chose pre-seed after raising $550M as a founder 08:14 Politics vs. craft: why big-company life left him cold 09:43 Parenting, girl-dad moments, and startup curveballs 14:26 Longevity, biohacking, and investing in healthspan 21:05 Craftsmanship in founders (and why manual watches matter) 27:58 From duct tape to scalable cloud: Vega Cloud’s reinvention story 30:09 Procurable AI: solving your own customer pain 34:55 Poker as due diligence: math vs. psychology 41:20 Handling bad beats — in poker and in startups 44:10 Trauma, drive, and proving Dad wrong 47:32 The worst day in venture: backing a fraud 49:20 Gratitude for Ron Conway, the OG angel 50:08 Legacy and letting kids live their own lives

Banana Costume Fundraising Tips with Ethan Austin from Outside Ventures | Alone Together | Ep. 10

"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 the seatbelts we needed on the way back to SFO with some of my favorite people in venture — many of them already guests on this pod.Ethan has turned an unorthodox life path—law school, nonprofit founder, Techstars MD, solo GP—into a razor‑sharp perspective on backing “outsider” founders in climate and financial inclusion. His secret weapon? Joy. The louder the banana costume, the clearer the signal that venture can—and maybe should—be fun. All kidding aside, he's taken that from a successful Fund I to launching Fund II and there are so many gems in here for founders, other GPs, or aspiring angels. In this episode Ethan and I dig into: - Why joy is a sourcing moat and how a goofy monthly LP update beats a glossy 30‑page PDF. - The banana‑costume epiphany: running law‑school bake sales in full fruit regalia and realizing he’d never be the greatest lawyer—but could be the happiest VC. - Firing an LP to reclaim headspace (and why “right capital” is better than “more capital”). - Solo‑GP triage: letting non‑critical fires burn, leaning on LP specialists, and knowing when to stop diligencing and trust the gut. - Authenticity at scale—posting kids’ photos, April‑Fools mergers with Banana Capital, and the power of repelling the wrong people so the right ones can find you. Ethan’s story is a reminder that vulnerability isn’t a soft skill; it’s a sharp edge. I hope you listen with an open heart—and maybe a slice of banana bread. ---Chapters 00:00  Cramped‑car origin story & why this episode took 3 months to schedule 02:52  Outside Ventures 101: Fund II, $250-$750 k first checks, outsider thesis 04:48  Defining “outsider” (mindset, not résumé) 08:32  Childhood wanderlust, hostel plots, and chronic authority‑allergy 10:18  Losing Dad at 12 → “Have fun, do good, help others” operating system 13:58  The legendary banana‑costume fundraiser (full marathon + training runs) 18:43  Joy as competitive edge: founders remember fun 21:18  Monthly LP updates people actually read (Easter eggs included) 26:06  Authenticity online: kids, jokes, and LinkedIn vulnerability 30:11  Why Ethan puts the banana photo inside his Fund II deck 33:06  Saying “no thanks” to a stressful LP 35:56  Humor dial: knowing when to crank it to 11—or drop to 0 36:15  Lessons from Fund I: focus on three superpowers, let the rest smolder 41:40  Diligence in practice: off‑list calls, product play‑tests, LP brain‑trust 47:03  Art vs. science in pre‑seed: when to quit researching and pull the trigger

Riding the Customer Obsession Wave to Venture Success | Inside Success VP with John Gleeson | Alone Together Ep. 9

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 empowering customer-obsessed founders. Customer success, according to John, isn't merely a department; it's a foundational mindset essential for deeply understanding markets, products, and founders themselves. Throughout this episode, John and I explore: * How the rhythm and intuition required in surfing mirror the unpredictability of markets and startups. * Why genuine empathy and obsessive attention to customer needs must be driven directly by founders. * The vulnerability and self-awareness required to pivot gracefully, whether on a board or in business. * His insights on building a solo GP fund anchored firmly in relentless customer focus and authenticity. John openly shares his unconventional journey, embracing risks and uncertainty as opportunities for growth—like when he chose to drop out of business school to chase waves around the world. Like surfing, venture demands courage, intuition, and the humility to accept when you've misread a wave. This isn't just a conversation about surfing and customer success—it's about how we navigate life's unpredictability with resilience, humility, and curiosity. I hope you listen with an open heart and an adventurous spirit. Chapters 00:00 Introduction to John Gleeson and His Journey 02:53 The Impact of Surfing on Business Philosophy 05:53 The Lean Startup Methodology and Its Influence 08:48 Understanding Market Positioning and Product-Market Fit 11:52 The Importance of Founder-Led Customer Success 14:48 Navigating the AI Technology Shift 17:48 Assessing Founders: The Diligence Process 21:03 The Artisan vs. Algorithmic Approach in Venture Capital 33:20 Hiring for Greatness: Insights from Experience 35:36 The Journey to Becoming a Solo GP 39:04 Finding Your Value Proposition in Venture Capital 44:15 Resilience and the Highlight Reel: Keys to Success 48:18 Language Market Fit: Navigating the VC Landscape 49:51 Celebrating Wins: The Best Days as an Investor 53:21 Lessons from Rejection: The Worst Days in VC 57:49 Legacy and Family: How to Be Remembered