He sold his Adtech company to Oracle after burning out, took it easy, then raised $100M+ for his next venture.

Most founders dream of a big exit but few talk about what happens after.

Subscribe & get our free investor/buyer list at thunder.vc.

Key Takeaways:The emotional and mental cost behind selling Crosswise to Oracle.How burnout nearly ended Ron’s startup journey—and what pulled him back.

The surprising truth about life inside a big corporation after acquisition.Why Sentra’s $100M+ raise was more about mission than money.

Ron’s lessons on cofounder chemistry, resilience, and building without losing yourself.

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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=Episode97&utm_id=%24100M++Exits

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode97&utm_id=%24100M++Exits

Here's what you're in for:

01:28 - Mental Health in Entrepreneurship

02:55 - Starting the Podcast: Oracle Acquisition Journey

03:32 - The Decision to Sell Crosswise

09:29 - Navigating the Acquisition Process

22:27 - Post-Acquisition Reflections and Retention

28:26 - Market Dynamics and Strategic Decisions

30:29 - Navigating Competitive Markets

31:23 - The Catalyst for Starting Anew

32:45 - Building with Friends and Finding Happiness

35:25 - Defining the Right Role

37:31 - Raising a Monster Seed Round

42:25 - The FOMO Round and Series B Success

49:28 - Investing in Founding Teams

54:54 - Advice for Founders on Raising Money and Selling Companies

58:06 - Final Thoughts and Wrap-Up

ABOUT RON REITER

Ron is a serial entrepreneur and cloud security expert known for turning complex technical challenges into scalable, real-world solutions. As the Co-founder and CTO of Sentra, he leads innovation in data security helping organizations regain visibility and control over their cloud environments.

Before Sentra, Ron co-founded Crosswise, a cross-device identification company that bridged digital identities across devices and was later acquired by Oracle for $50 million.With over two decades in software development and more than six years as an Engineering Director at Oracle Data Cloud, Ron managed the Tel Aviv R&D branch and led initiatives across ID graph, DMP, audience, and contextual data products. His career reflects a deep commitment to building secure, intelligent systems that power the future of data-driven organizations.

You can reach out to Ron through:

Website:https://www.sentra.io/ Linkedin:https://www.linkedin.com/in/ronreiter/

ABOUT JASON KIRBY

Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A.

He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A and business development.

He’s transacted over $135M and his firm Thunder has transacted over $200M+

You can reach out to Jason through:

Email: jason@thunder.vc

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

ABOUT $100M EXITS

My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it.

For most, it’s a dream to sell for $100M+, but for others it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast.

Be sure to subscribe and let me know who you want me to interview next.

What do you do when your company is on fire, literally or figuratively?What do you do when the deal is days away from closing — and your company’s reputation explodes overnight?In this episode, David Meadvin, CEO of One Strategy Group, breaks down what really happens in the “war room” when crisis hits and how to protect your credibility, investors, and valuation when everything’s on fire.Subscribe & get our free investor/buyer list at thunder.vc.💡 Key Takeaways:Why reputation capital is a real currency during dealmaking.How to recover from a PR disaster before it kills your valuation.The difference between damage control and trust rebuilding.Tactical playbook for founders facing internal or public crises.How to stay calm when everyone else is panicking.Timestamps:04:22 - Navigating an IPO Crisis08:49 - Frameworks for Crisis Management11:50 - Handling Political and Social Issues16:47 - Personal Crisis Stories and Lessons20:26 - Decision-Making in Crisis Situations23:58 - Navigating Stakeholder Reactions24:37 - Building Trust with Investors25:12 - Handling Crisis Situations27:18 - The Importance of Communication29:21 - David's Career Journey30:39 - Advise for CEOs and Founders35:06 - The Role of Politics in Business38:58 - Final Thoughts on Crisis Management51:47 - Maintaining Mental Health as a Founder-------------------------------------------------------------------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=Episode96&utm_id=%24100M++ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode96&utm_id=%24100M++ExitsABOUT DAVID MEADVINDavid Meadvin is the CEO and founder of One Strategy Group, a leading corporate and executive communications firm. With experience spanning both the public and private sectors, he’s advised Fortune 500 CEOs, political leaders, and top executives on high-stakes strategy and reputation management.Before founding One Strategy Group, David served as President of Laurel Strategies and held senior communications roles at Citadel, Bloomberg LP, and Facebook. In government, he was Chief Speechwriter for the U.S. Senate Majority Leader and Director of Speechwriting at the U.S. Department of Justice.Named to Washington Business Journal’s “40 Under 40”, David is recognized as one of America’s leading voices in executive communications, with work featured across major global media outlets.You can reach out to David through:LinkedIn:https://www.linkedin.com/in/meadvin/ Website: https://www.onestrat.com/ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: jason@thunder.vcLinkedIn: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.

Most founders sell the wrong way. Here’s how to do it right.

📣 Subscribe & get our free investor/buyer list at https://web.thunder.vc/vc-investor-list

What you’ll learn in this episode:

Forget the unicorn dream. This is how real founders achieve life-changing exits. Jason Kirby and Oliver Low — partners at Thunder — break down how to navigate the M&A process from both sides of the table: when to sell, how to structure a deal, and what to avoid when your future is on the line.

🔥 3-6 Tactical Takeaways:

• Why timing your exit matters more than valuation

• How to avoid the #1 killer of founder wealth: earnouts

• The rise of private equity buyers and what it means for startups

• How “venture orphans” can still create massive outcomes

• What Thunder looks for before taking founders to market

  
  

When Oliver Low sold his startup, it wasn’t a clean, overnight success story.

It was years of building, negotiating, and learning the hard way how M&A really works.

His company, Platform 360, eventually became part of a public company listed on the London Stock Exchange but the journey there was anything but straightforward.

There were earnouts that didn’t go as planned.

Buyers who vanished mid-deal.

And market conditions that turned every negotiation into a gamble.

For founders considering an exit or just trying to understand how real M&A unfolds — this conversation is a masterclass in playing the long game.

Want more insights? Check out the full shownotes for Episode 95! HERE