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

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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

19. maalis 202655 min

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

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