MBA2626 Extended Interview: Rob Walling - How to Build and Sell Your Business without Regret

What really goes into building a business you can actually sell—without second-guessing yourself later? Why do some founders walk away from negotiations feeling confident, while others are left wrestling with burnout, regret, or even an identity crisis? If you've been wondering about the mindset, strategies, and emotional prep behind a smart, well-timed exit, this episode is packed with insights you'll want to hear. Today, Omar sits down with Rob Walling—founder of Drip and TinySeed—for an extended, no-fluff conversation on building and selling your business without regret. You'll get behind-the-scenes insights on what makes a company truly sellable, practical ways to get exit-ready (even if selling isn’t on your radar yet), and an honest look at the personal journey of moving on after a sale. Plus, we’re pulling key lessons straight from Rob’s new book, Exit Strategy , co-written with his wife, psychologist Dr. Sherry Walling. Ready to future-proof your business (and your sanity)? Tap that play button at the top of the page and dive into the strategies, wisdom, and real talk that can help you build, scale, and—when the time is right—exit on your own terms. Watch the episodes on YouTube: https://lm.fm/GgRPPHi SUBSCRIBE YouTube | Apple Podcast | Spotify | Podcast Feed Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.