TMBA 478: 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 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

Published on 01.31.19
  • Guys, I’m a fan of your show and most of your episodes are solid, so please take this as constructive feedback from a listener: if I had to pick the most useless episode from your podcast, this would have to be it. The topic isn’t going to be relatable or relevant for the majority of listeners. I’m personally a relatively successful entrepreneur and the entire episode was just “first world problems”…C’mon…success doesn’t suck and as long as you don’t get complacent or sloppy, you do have a better shot at another successful business compared to someone who has never run a business, no matter how hungry they might be. I look back at some of my earlier ventures and there were so many mistakes made; mistakes that I was able to side step on the next venture. That’s not the point though. I just think the topic and discussion wasn’t beneficial. Just my opinion and I provide it in good spirit as a listener of your show and someone who has referred other entrepreneurs to join the DC.

  • Anonymous Entrepreneur

    Glad I can write this anonymously since I wouldn’t want to share this with my name on it but your quote below has been me for the last several years:

    “Man, I don’t have anything I’m excited about and I don’t have any goals.”

    Sure, I’ll be excited about things coming up like hanging out with my best buddies doing X, Y, and Z. In the present moment as those things unfold it’d be pure bliss. Smiling from ear to ear, baby.

    But the in betweens? The times every single day when everyone else is busy working during the day, and sometimes night, I find myself realizing I have so much free time and nothing to fill it with. The hustle is gone because success came too quick and easy.

    I find myself asking what’s next all the time. And I have to convince myself what do I do now…? Should I feel guilty for not wanting more?

  • Freddy Lansky

    Dan! Was this episode inspired by our chat or did we both coincidentally have lots of vegetables on our mind?

    Interesting episode but sometimes I inferred (perhaps incorrectly) that the sugar vs vegetables is mutually exclusive. I think a healthy business lifestyle has a bit of both. I tend to be 100% sugar (at least on my last biz) while some startup owners and more dreamy-eyed entrepreneurs have vegetable induced psychosis where they are still not making any more after 5 years.

  • Tom Marchment

    Another awesome show. I stick my headphones in and you make the time doing the most mundane household tasks a joy, whilst all the while helping me turn my nagging worries into positive thoughts on how to stay excited and cracking on with our business. How do you do it?!
    Thank you guys, I’ve listened to basically every ep. And still love em. Thank you again, again, again.

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