Most founders dream of a life-changing exit. But few actually prepare for it, until it’s too late.

In this episode of Fundraising Demystified, I sit down with John Rood, an exited founder who scaled a tutoring side hustle into a global edtech business, and sold it for over eight figures to private equity.John also shares the story behind his book Beyond the Exit and why post-exit life is often not what you think it will be.

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Raising capital?

Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode86&utm_id=FundraisingDemystifiedPodcast

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode86&utm_id=FundraisingDemystifiedPodcast

We talk:

00:00 – The Brutal Truth No One Tells Founders

02:04 – How John Turned Tutoring into SaaS Gold

05:21 – The Finance Hack That Boosted His Valuation

07:10 – What Really Kicks Off an Exit

11:08 – The $10M Mistake Founders Keep Making

13:59 – What’s Actually Enough for You?

17:01 – Why Most Founders Regret Life After Exit

22:52 – Angel Investing: The Ego Trap No One Admits

28:22 – The Weirdly Happy Knife Founder Story

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About John Rood

John Rood is the author of Beyond the Exit and the founder of one of the world’s leading pre-med test prep businesses. After scaling the company into a content-and-software powerhouse, he exited for over eight figures to a private equity firm. He now advises founders on exit strategy and post-exit reinvention, drawing from both his wins and the emotional landmines no one warns you about.

Connect with John: LinkedIn: https://www.linkedin.com/in/johnrood1/

Get the book: https://www.beyondtheexitbook.com/

What happens when you raise $2.7M... then realize you never want to raise again?

Jennifer Tsai, founder and CEO of Shoott.com, built a profitable photography marketplace from the ground up; surviving death threats from creatives, a brutal CAC spike post-iOS14, and the chaos of marketplace economics. In this episode of Fundraising Demystified, we dive into how she scaled to $10M in revenue, hit breakeven, and is now facing the “what’s next” moment many founders dream of, or dread.

Whether you're building a two-sided marketplace, wrestling with capital strategy, or wondering how to survive without more VC cash, this one's for you.

Raising capital?

Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode85&utm_id=FundraisingDemystifiedPodcast

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode84&utm_id=FundraisingDemystifiedPodcast

In this episode, you'll learn:

00:00 – Death Threats, Disruption & The Origin Story of Shoott.com

05:45 – Why Creatives Hated Us And How We Won Them Over

12:08 – From $80K to $10M: The Fundraising + Growth Playbook

17:52 – How We Hit Profitability (And 20x’d It)

21:26 – Cash Flow Roulette: Paying Creators Before Clients Pay Us

22:57 – The $300K Mistake That Nearly Sank Us

25:57 – Should You Raise, Sell, or Stay the Course?

27:32 – The Brutal Truth About Valuations in Today’s Market

30:38 – Founders: Before You Build a Marketplace, Watch This

This week on Fundraising Demystified, I sat down with David Connors, founder of The Swarm, a Go-To-Network platform transforming how founders and investors connect- think LinkedIn but for companies.

David shares how he used The Swarm to raise capital for his own startup, how the product helps other founders close rounds, and what he learned from working at Sequoia.

Raising capital?

Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode84&utm_id=FundraisingDemystifiedPodcast

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode84&utm_id=FundraisingDemystifiedPodcast

Sign up to get 70% off the Swarm: theswarm.com/thunder

Here’s what you’re in for:

00:42 - Who is David Connors and what is The Swarm?02:08 - How working at Sequoia birthed The Swarm

05:32 - Raising The Swarm’s $2M pre-seed round solo (and why it was capped)

11:37 - Raising a $4M seed and scaling a building a winning team

14:31 - How to find investors and pick the right ones for follow-on funding

18:52 - Getting warm intros for investor outreach in minutes

22:28 - The best kind of warm intros ranked

25:43 - Why Swarm raised an extension round

29:10 - The shift from SaaS to data, 10xing revenue and getting Hubspot Ventures to invest

32:40 - Vibe coding and AI tools that support The Swarm’s scale

35:02 - Top tips for personal branding that boosted growth

Check out the pre-seed investment memo for The Swarm here: https://docs.google.com/document/d/1wzo0PxFCyNgaD627-e2q2wefV0LUk4DJjnEr3R4b07k/edit?tab=t.0

ABOUT DAVID CONNORS

David Connors is the founder of The Swarm, a Go-to Network platform that helps startups access warm intros to capital, talent, and strategic partners. A second-time founder with deep experience in startup M&A, David previously built a company acquired by Levels, a Sequoia-backed health tech firm. With a background in enterprise sales and operations, he built The Swarm to solve one of the hardest problems founders face: getting in front of the right people without wasting time on cold outreach.

Connect with David via:LinkedIn: https://www.linkedin.com/in/connorsdavidWebsite: http://theswarm.com/

ABOUT JASON

Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.

You can reach out to Jason through:

Email: jason@thunder.vc

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

ABOUT FUNDRAISING DEMYSTIFIED

Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.

Thanks for tuning in! We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

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