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 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

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

“[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

"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

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

“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 ensure no one feels alone. From aluminum foil casseroles in Ohio to building vibrant WhatsApp networks in New York, Mike connects the dots between personal loss, behavioral science, and his distinct approach to venture capital.

Beyond his powerful personal story, we discuss Mike's innovative strategies for running Generous Ventures, including his pre-seed deal-sharing calls, disciplined community management, and thoughtful LP relationships—strategies that have resulted in an astonishingly high close rate among investors. Mike candidly shares both the challenges and breakthroughs he's experienced as a solo GP and the lessons he's learned along the way.

Mike's journey illustrates how personal adversity can deeply inform one's professional approach and investment philosophy, emphasizing the importance of community as both an emotional anchor and practical asset. Effective community building is rooted in clearly defined purpose and disciplined management, underscoring that meaningful connections must be intentionally cultivated rather than passively formed.

This conversation is a testament to the power of generosity, vulnerability, and intentional community building in venture capital and life.

Chapters

00:00 Introduction and Background

03:06 Generous Ventures: Fund Overview

05:13 Personal Journey and Influences

09:35 The Role of Community in Venture Capital

16:02 Building WhatsApp Groups for Investors

21:43 Organizational Strategies and Tools

24:21 Pre-Seed Deal Sharing Calls: Concept and Evolution

27:54 The Power of Generosity in Deal Flow

29:41 Lessons in Community Building

32:26 Artisan vs. Algo Funds

37:17 Advice for Aspiring GPs

43:29 Reflections on Highs and Lows

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-thumping, but actively building the world you want to see through meaningful, economically empowering ventures. His conviction comes from a deeply personal place—growing up as the son of military parents, witnessing his father's profound impact on wounded soldiers at Walter Reed, and carrying forward their legacy of service into a career defined by conviction and vulnerability.

Andy doesn't shy away from controversy here. We discuss openly why he believes venture done right can be an inherently patriotic act—because it enables societal change, economic empowerment, and the opportunity to shape the country we love. Equally compelling is his willingness to discuss faith and authenticity in an industry often dominated by data-driven personas.

We also explore:

• Andy’s deeply personal motivations for leaving traditional finance and launching Willpower VC.

• His thoughtful reflections on growing up in a military family and how that shaped his worldview.

• The practical ways patriotism and faith manifest in his fund's thesis and interactions with founders.

• The tension and synthesis between being an "artisan" GP versus an "algorithmic" investor.

• Real stories from the trenches of fundraising, including why saying "no" to tempting shortcuts helped preserve his fund’s integrity.

This conversation isn't just about patriotism and faith—it's about how we show up fully as investors, entrepreneurs, and human beings, with all the complexities and contradictions that entails.

I hope you listen with openness and curiosity. It’s rare to hear such vulnerability and nuance about topics too often simplified or sidestepped entirely.

Chapters

00:00 Introduction and Background of Andy Will

04:18 The Journey to Starting Willpower Venture Capital

07:11 Childhood Influences and Values

10:09 The Impact of Military Family Background

13:00 Patriotism and the Role of Venture Capital

16:20 Connecting Personal Values to Business

19:01 The Art of Fundraising and Building Relationships

22:03 Navigating Challenges as a Solo GP

25:03 The Importance of Support Systems

27:57 Artisan vs. Algorithm in Venture Capital

31:05 Identifying Ideal Founders for Investment

34:03 The Role of Personal Interactions in Diligence

34:43 Navigating Personal Interactions in Investment Decisions

37:55 The Journey of a Solo GP

40:20 Building Trust and Partnerships

42:38 The Challenge of Investor Expectations

44:55 The Nuances of Risk in Solo GP Dynamics

48:42 The Importance of Support Networks

52:45 Advice for Aspiring Solo GPs

55:14 Influential Figures in the Journey

56:51 Reflections on Low and High Points

59:13 Legacy and Values for Future Generations

"Algos scale. Artisans don't. But maybe that's the point." — Charles HudsonIn 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. However, between our booking and recording date, Charles published a profound essay, "What Does It Mean to Be a Venture Capitalist Today?"—prompting our conversation to become deeper and more philosophical than anticipated. It felt like too important an opportunity to pass up, leading us into an expansive dialogue about the essence of venture capital itself.While we do dive into the critical debate around algorithmic vs. artisan investing, we also explore broader reflections on how venture capital is evolving and what it truly means to be an investor today.While we do dive into the critical debate around algorithmic vs. artisan investing, we also explore broader reflections on how venture capital is evolving and what it truly means to be an investor today.

We had a real honest conversation about a number of topics (Charles: "God, I don't know why I feel so free today). Just to name a few:
- The transformation and institutionalization of solo GPs, from early skepticism to acceptance and the current wave of "small and weird" funds.- The philosophical and practical implications of the shift toward algorithmic investing, and why Charles passionately advocates for preserving artisanal, human judgment.- Real-world tensions between scale, creativity, and differentiation, impacting fund construction, LP relationships, and deal processes.- Charles's personal reflections on the deeper motivations and responsibilities of being a venture capitalist.Key moments:(01:16) Charles Hudson’s career journey and founding Precursor Ventures(03:42) Evolution of solo GPs in venture capital(07:03) The philosophical debate on algorithmic vs. artisan investing(17:01) The challenge of differentiation in venture(29:44) The importance of "small and weird" in maintaining innovation(39:58) Charles’ approach to keeping Precursor Ventures intentionally artisanal(50:27) Personal reflections: What Charles hopes his son sees in his workStandout insights from Charles:"When everything feels spreadsheet-driven, we lose the ability to bet on truly innovative ideas that don't neatly fit existing heuristics.""The artisan fund can't scale infinitely—but maybe that's exactly why it matters.""What do you lose when the entire industry shifts toward algos? You lose the art, the insight, the judgment calls that defy simple metrics."Join us for this reflective exploration on not just the future of venture capital—but its very soul."

“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 games from the press box with her godfather, the first Black sportswriter at the New York Times, to becoming a visionary investor reshaping the landscape of sports, media, and technology.

Lorine’s investment thesis is bold and personal: women's sports, media, entertainment, and tech at the intersection of innovation. Far from cherry-picking trendy sectors, Lorine has long been ahead of the curve, spotting seismic shifts well before mainstream investors noticed (and if you wear an Oura ring, there's your proof).

If you've ever wondered how personal identity and early experiences can drive exceptional investment insights, this episode is a must-listen.Join us as we explore:

- Harlem's Lasting Influence

How Lorine’s upbringing and community taught her the value of resilience, spotting overlooked opportunities, and staying true to her roots in everything she does.

- The Rise of Women's Sports

Why Lorine sees unprecedented potential in women's sports—not just as an investor, but as someone who’s spent years quietly supporting from the stands, long before stadiums filled up.

- Authenticity in Fundraising

Lorine candidly shares why genuine passion is her secret weapon in fundraising, even when navigating the tough realities of going solo in a challenging VC environment.

- Building a Team as a Solo GP

Why assembling a collaborative advisory team is essential, how she convinced industry leaders to join her journey, and the practical insights she’s gained along the way.

- Sports as More Than Investment

A thoughtful discussion on how sports offer access, inspiration, and social mobility, creating deeper societal impacts beyond just financial returns.

No clichés, just real insights from an investor who’s authentically reshaping venture capital by combining personal ethos with market foresight.

Subscribe for more candid conversations with the solo GPs and innovators quietly rewriting the rules of venture capital.

“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, and why living life as a “whole” person (kids, family, and all) makes her a sharper investor.

Virginie candidly shares her journey—from watching her parents struggle to build a horticulture business in rural France, to stumbling into venture at Tusk, to going all in on a radically different solo GP structure. If you’ve ever questioned whether traditional VC fund structures are truly designed for today’s founders (or for your own lifestyle), this conversation is for you.

Join us as we cover:

- A New Model for Venture

Why Virginie chose a permanent fund over the traditional 10-year model—and what that really means for LPs and founders.

- Embracing ‘Nonlinear’ Work

The core thesis behind FullCircle: empowering people to enter and exit work on their own terms, much like her own unorthodox path.

- No Plan B (and No Partner)

The psychological and practical realities of going solo, and how “partnership risk” can be just as big a worry for LPs as the fabled “hit-by-a-bus” scenario.- Life & Business, IntegratedHow Virginie involves her children in the ups and downs of fund life—plus the “ruthlessly honest” conversations she has with founders as a result.

- Why Feedback Matters

The cultural differences that inform Virginie’s direct, no-BS approach with founders, and how it creates deeper trust and better decision-making.

No vague startup clichés—just a real, unfiltered look at building a life and venture model on your own terms.

Subscribe for more candid conversations with the industry insiders who are quietly reshaping venture capital and leveling the playing field—one solo GP at a time.