60 pitches in 90 days. A Series B term sheet that collapsed. A $15M valuation hit, and she still came out on top.

In this episode, Jennifer Henderson, founder of Colorado-based HR tech startup Tilt, breaks down exactly what it took to raise over $30 million in venture capital while balancing motherhood, market crashes, and investor whiplash.

Jen shares how Tilt was born out of personal trauma, why she built a leave management platform with empathy at its core, and what every founder, especially women, needs to know before walking into their next pitch.

From Techstars to term sheet disasters, this is the real story behind startup success in today’s market.

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

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=Episode88&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=Episode88&utm_id=FundraisingDemystifiedPodcast

Here's what you're in for:
00:00 – “I don’t come from money”: Why Jen chose venture

04:21 – Building Tilt from personal pain

06:08 – Sales tactics that worked

09:07 – How Techstars changed the fundraising game

11:53 – Raising Series A: Saying no to ‘cute’ term sheets

18:03 – Series B nightmares: exclusivity traps, errors & resilience

33:07 – The truth about AI in HR tech

39:02 – Advice to female founders: “Be successful. We need you.”

42:56 – Surviving the current startup market

ABOUT JENNIFER HENDERSON

Jennifer Henderson is the founder & CEO of Tilt, a Colorado-based HR tech platform that simplifies and humanizes leave of absence management for modern teams. After two traumatic parental leave experiences, she turned her frustration into a mission. From Starbucks barista to corporate leader to raising $30M+ across five rounds, Jen's journey is a masterclass in resilience, grit, and founder-first leadership. Tilt is now a trusted solution for teams across the U.S., navigating complex leave policies with care.

Connect with Jennifer on:LinkedIn: https://www.linkedin.com/in/jenniferhendersonjctcjcdcEmail: hello@tilt.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.

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 talk to Travis Steffen, who has built and sold eight companies. He’s raised over $100M and driven more than $200M in exits.

In this episode, we delve into what actually drives startup growth and what quietly undermines it. We also get into how one bad exit almost wrecked him, and what he learned from losing years and seven figures because of one avoidable mistake.

If you're a founder, operator, or even just thinking about building, this episode will give you a clearer view of what’s worth your attention.

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

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=Episode87&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=Episode87&utm_id=FundraisingDemystifiedPodcast

We get into:

00:00 The Real Startup Journey: No Filters, No Hype

03:07 Why "Never Quit" Is Holding You Back

05:47 Churn: The Growth Killer Founders Ignore

09:12 What You Learn When a Startup Fails

12:05 Retention Isn’t a Metric. It’s a Strategy.

14:52 Why Investors Walk, Even If Your Numbers Look Good

17:48 The Retention-Valuation Link You Can’t Ignore

21:06 From Flatlined to $70M: A Turnaround Breakdown

34:37 How We Built the Most Trusted Brand in a Broken Industry

36:19 Revatto: Built to Solve Churn Without Adding Work

40:07 No Results, No Cost: A Different Kind of Retention Model

42:29 How To Save Customers, Without a Product Tutorial

45:10 You Probably Don’t Understand Your Churn. Here’s Why.

47:24 How to Test Revatto, with $1,000 in Free Recoveries

51:21 One Retention Habit That Changes the Game

54:24 The Exit That Went Sideways, and What It Cost

ABOUT TRAVIS STEFFEN

Travis Steffen is a founder, operator, and builder with a track record most founders never reach. He’s exited eight companies, raised more than $100M, and led over $200M in M&A. His work spans SaaS, cannabis tech, fintech, and AI. Today, he’s the co-founder of Revatto, a company that helps subscription-based businesses retain more customers and only charges when it works.

Check out Revatto: https://www.revatto.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.

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.

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.

----------------------------------------

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

-----------------------------------

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.