Built from the Bottom: Kenny Donnell’s Unstoppable Rise

What do you do when life gives you a 10-year sentence? If you’re Kenny Donnell, you turn it into a masterclass in resilience, hustle, and building your own damn seat at the table. In this episode, Kenny opens up about how being denied a job post-prison led to an unexpected but powerful entry into entrepreneurship—and how his “accidental” business launch turned into a lifelong calling.

We go deep into Kenny’s remarkable story: from being rejected by fast food joints to flipping his first house for a massive profit and eventually launching companies in construction, transportation, and now coaching. But it wasn’t all smooth rides and six-figure flips. Kenny shares hilarious and humbling lessons, like how his first limo business cost more in suits than it made in sales (spoiler: Emmitt Smith was their one client—no big deal).

Now, Kenny is on a mission to help others shift from employee to boss—whether they’re launching a business or transforming their mindset within corporate. His book From Employee to Boss isn’t just for aspiring founders; it’s for anyone ready to solve problems, own their value, and bet big on themselves. If you’ve ever felt stuck, sidelined, or unsure where to begin, this episode will fire you up to take that first step—and keep walking even when the road gets rough.

 

Takeaways:

• Necessity breeds entrepreneurship: Kenny’s journey started when no one would hire him post-incarceration. So he created his own opportunities—and never looked back.
• Mindset is everything: Whether you're in corporate or self-employed, thinking like a boss means solving problems and bringing solutions to the table.
• Fail fast, learn faster: From a limo biz that flopped to getting his dream truck repossessed, Kenny shares why failures can be your best business school.
• The power of one big win: His first house flip changed everything—it gave him the confidence (and cash) to go all in.
• Get operationally sound: Having a great idea isn’t enough. You need systems, financial awareness, and clarity to succeed long-term.
• Bet on yourself: You may not have all the answers now—but if you keep showing up, learning, and building, your future is limitless.
   

Chapters

00:00 Kenny Donnell’s Unexpected Path to Entrepreneurship

02:44 How a Random Encounter Led to His First Business

07:12 Facing Rejection and Rebuilding with Resilience

10:58 Flipping His First House and Catching the Entrepreneur Bug

13:34 The Limo Business That Taught a Priceless Lesson

17:28 Why Talent Alone Doesn’t Guarantee Success

19:40 Developing the Mindset to Lead and Solve Problems

21:36 Why He Wrote From Employee to Boss

23:22 Personal Milestones and Big Dreams Ahead

24:49 Parting Advice: Bet on Yourself and Keep Moving Forward