Alone Together: The Story of Solo Venture Capitalists

"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 earliest collaborators when it comes to discussing Vertical SaaS opportunities—I deeply admire his grit, hustle, and relentless grind.We dive deep into Nick’s remarkable journey, from flipping golf balls on eBay as a kid to dropping out of college just three weeks after discovering the startup world. Nick openly shares how scaling Greenlight Guru gave him the unique perspective and experience needed to become a strategic investor.Join us as we cover:

• The pivotal "holy s#@&" moment that set Nick on his path

• Why he took the bold leap to leave college early for entrepreneurship

• His candid experiences in launching a solo GP firm

• The massive opportunities in Vertical SaaS and Vertical AI

• Building a VC firm strategically outside Silicon Valley

• Actionable, real-world advice for founders and aspiring solo investors

No startup clichés here—just authentic, personal stories and meaningful insights into building a life and business you believe in.Subscribe for more unfiltered conversations with remarkable investors, founders, and creators redefining venture capital.

Chapters

00:00 Introduction to the Podcast and Guests

06:00 The Holy Shit Moment: Discovering the Startup World

15:43 Advice for Aspiring Solo GPs

24:29 Understanding Vertical SaaS

38:52 Navigating Challenges and Low Points

44:16 Looking Ahead: Future Plans for TipTop

46:58 New Chapter

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 admired how she’s blazed a trail for solo GPs, building something unmistakably her own. And let’s be real: she literally puts badass woman right on her front door. That’s no accident—that’s a statement.

I’m also honored to co-invest alongside her in Viva and Papaya, two incredible companies that further prove what I’ve always believed: when Samara backs a founder, it means something.

In this conversation, we get real about:
-How she fearlessly built Chingona Ventures from scratch
- The discipline and structure that make her a machine (and why I’m straight-up stealing her systems)
- How she wins over LPs who hesitate on solo GPs (and whether she’s ever changed someone’s mind)
- What it felt like fundraising while literally having a baby (and how her processes held up under the ultimate stress test)
- The hard moments—because, yes, even Chingonas have low points
- The mental game of solo GP life (including therapy, scheduled downtime, and saying no to the right things)
- How she sees the market evolving—and what she’s eyeing next

Samara is proof that this game isn’t just about capital—it’s about conviction, clarity, and sheer force of will. And in this episode, she brings it all. If you’re a solo GP, an aspiring investor, or just someone trying to figure out how to carve your own path, you do not want to miss this.

Go to https://www.chingona.ventures/ to find out more about Chingona Ventures.

Chapters

00:00 - Introduction to the Podcast and Guest

01:52 - Samara's Journey into Venture Capital

05:49 - Personal Background and Its Influence

10:08 - Overcoming Challenges and Low Points

17:31 - Navigating the Solo GP Landscape

23:08 - Changing Perceptions of Solo GPs

26:22 - Efficiency in Solo GP Operations

27:53 - The Importance of Process and Transparency

29:59 - Evolving Investment Processes

33:45 - Continuous Improvement in Decision Making

36:12 - Incorporating Team Perspectives

43:06 - Balancing Parenthood and Professionalism

50:57 - New Chapter

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 it really means to be a solo GP, why thinking contrarian can open unexpected doors, and how “growing where you’re planted” can unlock fresh opportunities in both investing and life.

Kevin also shares practical tips for raising a fund on your own terms, including creative ways to find “net new” LPs—beyond the same rooms everyone else is pitching—and how to leverage genuine human connections in an age of AI. We talk about the hustle of building your firm from scratch, the power of leaning into your local community, and the importance of staying grounded even as you scale. If you’ve ever wondered about the bumps, bruises, and (ultimately) thrilling moments of going it alone in venture capital, this episode is for you. Enjoy the conversation!

To get in touch with Kevin, reach out to him on LinkedIn: https://www.linkedin.com/in/kevinjosephmoore/

Chapters

00:00 The Journey of a Solo GP

29:22 Building a Fund: Strategies and Insights

39:28 Networking and Fundraising: The Net New Approach

49:30 Growing Where You're Planted: A New Perspective

58:14 Final Thoughts and Reflections

58:45 New Chapter

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 without a traditional partnership? We’ll explore the personal stories, unique strategies, and hard-earned lessons of those charting their own path in the venture world.

Subscribe now and join us as we dive into the world of solo GPs—because even when you’re investing alone, you’re never truly on your own.