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 Welcome back to Alone Together and Season 2 kickoff 01:00 Ben’s background and the origin of Oncology Ventures 08:30 What the cancer care system is still getting wrong 13:15 Cancer and comedy, and why humor mattered 19:45 Selling yourself as a solo GP without overperforming 25:00 Emotion, fundraising, and the reality of venture 33:00 The solo GP myth and what support really looks like 38:30 How emotion can actually sharpen investment judgment 47:30 Fast Four: best day, worst day, shoutout, and legacy
