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?

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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.

#startupfunding #venturecapital #theswarm #founderstories #fundraisingdemystified #saas #data #investoroutreach

In this episode, Jess Loren, founder and CEO of Global Objects, shares her journey on raising capital as a female founder, including turning down a $20M offer and building her business using digital twins technology.

Jess dives into how she's building a tech company rooted in culture, purpose, and innovation, while navigating the fundraising landscape as a female CEO. We talk about generative AI in media, managing a startup as a mom, building a tech community, and how to use AI to boost productivity.

A great story about leadership, innovation, and startup resilience.

—-------------------------------------

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=Episode83&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=Episode83&utm_id=FundraisingDemystifiedPodcast

Here's what you're in for:

00:00 - Intro

00:35 – Raising Capital as a Female Founder: Intro to Jess Loren & Global Objects

03:06 – Building a Tech Community in LA

06:05 – Balancing Life as a Female CEO

08:42 – Digital Twins Technology for Culture & Innovation

13:16 – Using AI to Boost Productivity in Creative Industries

16:34 – Generative AI in Media & Entertainment

22:18 – Jess Loren’s Journey: From 2X Exit Founder to Building Global Objects

25:47 – Funding Strategies & Investor Alignment

28:16 – Global Objects' Mission and Growth Plan

31:30 – Startup Leadership as a Female CEO

34:05 – Jess Loren on Persistence, Boards & Building Visibility

ABOUT JESS LOREN

Jess Loren is a 2X exited founder and the CEO of Global Objects, a cutting-edge startup at the intersection of digital twins technology, cultural preservation, and generative AI. With a background in community building, immersive experiences, and Web3 innovation, Jess is known for her bold leadership, fundraising acumen, and vision for reshaping how we digitally capture and interact with the world. Her journey includes turning down a $20M term sheet to stay mission-aligned, proving that purpose and persistence can coexist at scale.

You can reach out to Jess through:

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

Global Objects' LinkedIn: https://www.linkedin.com/company/globalobjects/

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.

Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

This week, I host IPO market expert Peter Goldstein, who talks about the best time to IPO, how to position for strong IPO performance, what true IPO readiness looks like, and how companies are being valued in 2025.

If you're a founder eyeing the public markets, this is your roadmap. We dive into shifting investor sentiment, the surge in the secondary market, and strategic insights on when to go public, build public company credibility, and leverage equity in IPOs to your advantage.

______________________________________________________________

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=Episode81&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=Episode81&utm_id=FundraisingDemystifiedPodcast

Here's what you're in for:

00:00 – The 2025 IPO market

02:15 – Investor sentiment in the current IPO climate

04:40 – Why IPO timing is critical: the best time to IPO

07:25 – IPO valuation expectations and market sensitivities

10:05 – IPO readiness checklist for founders

12:50 – What happens after IPO: risks and surprises

16:15 – IPO performance in 2024 vs 2025

19:30 – Market cap requirements for IPO explained

22:10 – How equity in IPO impacts control and growth

25:20 – Benefits of going public beyond capital

28:05 – Public company credibility and strategic advantages

31:15 – The rise of the secondary market and investor access

34:30 – Private stock trading trends and access to liquidity

37:20 – When should you go public?

40:10 – Employee stock incentive strategies in public companies

43:30 – Parting shot from Peter Goldstein

ABOUT PETER GOLDSTEIN

Peter Goldstein is a leading expert in the IPO market, founder of Exchange Listing LLC, and author of The Entrepreneur’s IPO. With decades of experience guiding small and micro-cap companies through public offerings, Peter is known for helping founders navigate the complexities of going public. His deep understanding of IPO readiness, valuation, and investor strategy makes him one of the most trusted voices in the space.

You can reach out to Peter through:

LinkedIn: https://www.linkedin.com/in/peter-goldstein-exchangelisting/

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.

Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

JC Glancy, co-founder of ZenBusiness, shares his remarkable unicorn startup journey, from nearly drowning in credit card debt to building a billion-dollar startup. In a bold and rare move, he gave up the CEO title early on but still led the company to raise a $200M Series C and dominate the legal tech space.

This episode dives deep into startup realities: raising venture capital, overcoming failure, building an unbeatable team, outmaneuvering big competitors like LegalZoom, and scaling ZenBusiness through SEO, affiliate marketing, and obsessive customer focus.

______________________________________________________________

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=Episode80&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=Episode80&utm_id=FundraisingDemystifiedPodcast

Here's what you're in for:

00:00 – Intro: JC Glancy’s founder success story begins

02:30 – Credit card debt & early startup struggles

06:15 – Building ZenBusiness into a unicorn startup

09:00 – Giving up the CEO title: The bold move

12:50 – How ZenBusiness outperformed LegalZoom

16:10 – Product market fit: Why the early products failed

19:45 – The SEO and affiliate marketing funnel that scaled

23:30 – Fundraising strategy: From angels to $200M Series C

28:20 – Building a powerful startup team without resources

32:10 – COVID pivot story: How ZenBusiness exploded in growth

37:00 – Recruiting top talent post-Series C

41:30 – Founder exit strategy: Why JC stepped back

45:00 – What JC is building next + advice for future unicorn founders

ABOUT JC GLANCY

JC Glancy is the co-founder of ZenBusiness, a unicorn startup that helps entrepreneurs launch and grow their businesses. From maxed-out credit cards to a $1B valuation, JC’s journey is a powerful founder success story. As head of product marketing, he built ZenBusiness’s marketing machine—driving explosive growth through SEO, affiliates, and data-driven customer insights. He gave up the CEO title, helped raise a $200M Series C, and led the company to outpace giants like LegalZoom.

Connect with JC:

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

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.

Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.