In this episode of the Stay Broke Podcast, we sit down with Dan Wilson, Managing Partner of Viking Mergers & Acquisitions and a man who’s lived every side of entrepreneurship — from the grind of startup life to the strategy of multimillion-dollar exits.

Dan’s story begins in the U.S. Air Force, where discipline, structure, and leadership became the foundation of his entrepreneurial mindset. After leaving the military, he built an IT company from the ground up, navigated multiple acquisitions and a merger, and eventually sold his business for millions. Now, as a Managing Partner at Viking M&A and founder of their Raleigh, North Carolina office, Dan helps other business owners prepare for the single largest transaction of their lives — selling their company.

We cover it all — from what makes a business truly worth buying to how owners can build systems, teams, and financials that attract premium buyers. Dan shares eye-opening insights on:

The emotional and strategic side of selling your business

The “Silver Tsunami” — the trillion-dollar wave of baby-boomer business exits coming in the next 10–15 years

How AI tools like ChatGPT are now influencing how buyers and sellers find each other

The biggest mistakes owners make when they wait too long to plan their exit

Why valuation isn’t just about revenue — it’s about readiness, documentation, and leadership depth

Through every part of the conversation, Dan’s passion for helping his clients make informed, confident decisions shines through. Whether you’re just starting to think about succession or you’re already building toward a sale, this episode gives you the playbook to grow smarter and exit stronger.

🎧 Tune in to learn what it really takes to build a business that’s ready for sale — and why your best exit starts long before the first offer ever lands on your desk.