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.

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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=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.