"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