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

The $100 MBA Show

Omar Zenhom

Entrepreneurship, Business, Careers, Marketing

4.8 • 2.2K Ratings

🗓️ 19 May 2025

⏱️ 74 minutes

🔗️ Recording | iTunes | RSS

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Summary

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.

Transcript

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0:00.0	Today on the podcast, I sit down with a well-known founder and investor Rob Walling.
0:04.9	Rob Walling is the founder of Drip, which is one of the most popular email marketing
0:09.4	softwares out there. He sold that business and then started one of the most successful
0:13.3	incubator accelerator programs, Tiny Seed, that invests in over 200 companies.
0:19.4	He's also the founder of one of the best SaaS conferences I've ever seen in my life.
0:23.4	I've attended twice.
0:24.2	It's called MicroConf.
0:25.7	I highly recommend it.
0:27.2	He's got a highly successful podcast called Startup for the Rest of Us, as well as a growing YouTube channel.
0:32.6	I'm so excited to sit down with Rob and discuss all things of business, but in particular, building
0:39.1	a business to sell one day, to exit.
0:44.0	Welcome back to the $100 MBA show.
0:50.0	I'm your host, Omar Zen Home, where I deliver practical business lessons three times a week,
0:54.7	Monday, Wednesday, and Friday to help you start, grow, and scale your business.
1:00.9	I reached out to Rob because I wanted to sit down and talk about this topic because he just
1:04.7	recently released a new book, one of many books that he has ran, but this is his latest book,
1:09.2	Exist Strategy, co-written with his wife,
1:11.9	Dr. Cheryl Walling, which is really cool. And she is a psychologist. She specializes in helping
1:18.1	founders not only in the exit phase of their business, but just going through the struggles
1:23.0	of being an entrepreneur and a founder. Now, if you're not thinking even about selling your business,
1:27.5	maybe you haven't started yet. You're in the right place because we're going to be talking
1:31.1	a lot of things that you should keep in mind even if you think you'll never sell your business
	...

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