Start Smart, or Start Over
Fundraising without strategy isn’t growth—it’s gambling.
We love a good success story. Especially the ones with champagne moments: a founder lands a massive funding round, the press swoons, and the startup seems destined for unicorn status. It's the modern hero’s journey—risk everything, raise millions, change the world. But the part we rarely hear about in the headlines is what happens after the check clears.
Take WeWork, once a $47 billion darling, now a masterclass in overvaluation and poor governance. Or Quibi, which secured nearly $2 billion from investors before its product ever saw the light of day, only to collapse in less than a year. And then there’s Theranos, a story so notorious it became a miniseries, where the cult of vision raised more than $700 million on a lie. In each case, the capital wasn’t the problem. It was how it was raised, who it was raised from, and the structural flaws that were baked in long before the product failed.
For many first-time founders, the idea of raising venture capital is seductive. It feels like validation. Proof that your idea matters and that your company is real. But funding is a tool—not a trophy. And when it’s used improperly or taken from the wrong hands, it can do more harm than good. There’s a cost to capital, and it doesn’t always come in dollars.
What if your investors don’t actually understand your space? What if the terms you agreed to sabotage your future exit? What if you didn’t need to raise at all, and could’ve bootstrapped a profitable business while retaining full control? These aren’t hypotheticals. They’re the postmortems of startups everywhere, and they’re often only realized too late.
This week’s guest, and Eggs! The Podcast alum, Jason Kirby, has been through it all: the exhilarating raises, the last-minute acquisition heartbreaks, the pivots, the deals that fell apart at the finish line. But rather than burn out or disappear, he’s built a platform—Thunder VC—to help other founders avoid those same traps. His approach combines data, AI, and lived experience to match startups with the right investors, at the right time, for the right reasons.
If you're a founder—or even just a future one—what Jason shares could change the way you think about capital entirely. Because, as it turns out, getting funded isn’t the win. Getting the right funding on the right terms is.
Meet the Founder Who’s Seen It All (Twice)
Jason Kirby is a veteran entrepreneur who’s not just built companies—he’s rebuilt them. Over the course of his career, he’s been at the helm of four startups that have either been acquired or successfully exited, raising over $40 million in the process. From early ventures in event photography to high-stakes roles in gaming, cloud infrastructure, and HR tech, Jason’s journey has been marked by adaptability, grit, and a deep understanding of what it really takes to grow and fund a business.
His experience is unusually well-rounded: he’s been a founder, a C-suite operator, an angel investor, and now, a builder of tools for other founders. After a series of hard-earned lessons—deals falling through at the 11th hour, strategic pivots under pressure, and the constant friction of raising money while building a business—Jason co-founded Thunder VC. The platform uses data and AI to match startups with investors who are actually aligned with their stage, sector, and strategy. It’s a startup’s shortcut to not just a check, but the right check.
Today, Jason works with thousands of founders and capital allocators, helping to demystify the process of fundraising and push back against the noise and mythology that surrounds venture capital. His perspective is clear-eyed, founder-first, and grounded in lived experience—making him one of the most practical voices in the startup capital conversation.
What Founders Get Wrong About Fundraising
Jason Kirby has seen every side of the startup capital game—founder, operator, investor, and now, builder of a platform that helps others do it smarter. What he shares in this conversation isn’t theory—it’s field-tested advice forged through near-misses, hard pivots, and hard-won exits. Here are some of the best insights from our conversation, paired with ideas you can act on now.
“You’re always selling the upside. But inside, it’s chaos.”
The insight: Founders must master the art of narrative—but never mistake the pitch for the plan. Build your internal systems as seriously as you build your external story.
“Chasing the wrong investors is a full-time job—and a total waste of time.”
The insight: A warm intro isn’t enough. Vet your investors as carefully as they vet you. Misalignment in thesis, stage, or expectations can be fatal.
“There’s this idea that getting money means you’ve made it. But the real work starts after the check clears.”
The insight: Don’t let fundraising become a vanity metric. Capital is fuel, not a destination.
“If you have the ability to build a profitable business, why raise money?”
The insight: Venture capital is for scale, not survival. Sometimes the smartest raise is no raise at all.
“Once you go down the VC path, you never stop fundraising.”
The insight: Be ready for the treadmill. VC funding is iterative—you’re signing up for a decade of growth, not a one-time boost.
“Angel investors invest in people. VCs invest in outcomes.”
The insight: In early rounds, lean into who you are as a founder. Later on, it’s all about your metrics.
“If you’re afraid your pitch deck will be stolen, you don’t have a moat.”
The insight: A truly defensible business isn’t threatened by exposure. If you can be copied easily, you need to rethink the model—not hide it.
The Smartest Money Might Be No Money at All
TThe startup world glamorizes fundraising like it’s a badge of honor. But as Jason Kirby makes clear, the real flex isn’t how much you raise—it’s how clearly you understand whether you even need to. Capital can accelerate growth, but it can also add pressure, dilute ownership, and tether you to expectations that don’t align with your long-term vision.
Jason’s story is a reminder that wisdom in entrepreneurship often comes from hard-earned scars. Whether you’re chasing a venture-backed rocket ship or building a profitable lifestyle business, what matters most isn’t how fast you move—it’s whether you're moving on your own terms. Before you take the money, take a moment to define the game you’re actually trying to win.
Thanks for reading,
—Ryan
Ready for more?
Catch Jason Kirby’s interview in its entirety on Eggs! The Podcast.
Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.
Path Picks
Cool stuff to help you forge your path to greatness.
Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R
Reading list
If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective on learning, systems, and the future of work:
The Cold Start Problem by Andrew Chen
A tactical breakdown of how startups gain traction, written by a General Partner at Andreessen Horowitz. Helps founders think like investors and scale like strategists.The Lean Startup by Eric Ries
A modern classic for startup operators. Focuses on validated learning, product-market fit, and iterative building—especially relevant before taking on capital.Secrets of Sand Hill Road by Scott Kupor
A former VC explains the inner workings of venture capital from an operator’s POV. Essential reading for anyone preparing to raise funds or structure a cap table.
More to explore
Jason Kirby Websites:
https://www.linkedin.com/in/jasonrkirby
https://web.thunder.vc/
https://www.jason-kirby.com/
Work with me
Ryan Roghaar - Fractional CMO/Creative Director/Art Director: https://rogha.ar/portfolio
R2 - Creative Services for Agencies and SMBs: https://www.r2mg.com
Eggs! The Podcast: https://www.eggscast.com
Would you like a personal introduction to any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
Contact me here to learn more about my B2B matchmaking service.
Get featured
Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.