TMBA478: The Downsides of Success

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“Success” isn’t always what it’s cracked up to be.

Dan and Ian know this feeling all too well, as they have dealt with some of their own internal struggles after selling their product business.

On today’s episode, we are talking about five specific downsides to success.

These aren’t necessarily strategic elements, as much as they are about the mindset of success.

You’ll hear about some of the common traps that successful entrepreneurs often find themselves in, and how success itself can actually become a competitive disadvantage.


Listen to this week’s show and learn:

  • How success can give us “Rose Colored Glasses”. (2:46)
  • The difference between “sugar” and “vegetables” when it comes to your business. (6:10)
  • How “Bloodsuckers” can drain you of your time, resources, and energy. (12:12)
  • Why success can sometimes leaving us struggling to find meaning. (16:15)
  • The dangers of living in a bubble. (20:12)

Mentioned in the episode:

This week’s sponsor:

This week’s episode is brought to you by Dynamite Jobs. Dynamite Jobs is a service that helps entrepreneurs and listeners of this show find top, experienced talent to join their teams.  These types of remote positions can be especially challenging to hire for, and we specialize in making that process easy.  For those of you who are on the hunt for a new opportunity, we know how frustrating it can be to find good remote jobs, so we only work with established, reputable companies offering great remote opportunities. If you’re looking for a new job in the new year, check out

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Grab your free copy of our book!

In the entrepreneurial world, it’s rarely questioned that “exiting” is the end goal of a smartly built business and a prestigious waypoint in a successful career.

In 2015, Dan Andrews and Ian Schoen sold their business for multi-seven figures, and although they don’t regret selling – there are many mistakes they made that were avoidable.

The book presents thought experiments designed to help you avoid similar mistakes.

Whether you are in the early stages of building a business or thinking of selling, this book is designed to help you build with the future in mind.

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Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST. Cheers, Dan & Ian