"Which entrepreneurs have made $20mill+ in under a decade with a balanced lifestyle (no more than 50hrs work/wk)?


Do you think it’s possible to do it all? Myself and entrepreneur Martin Bjergegaard are making it our mission to find this out in hopes of writing a book outlining the lessons of our findings. We are searching far and wide for those that fit the profile outlined below. If you know of any entrepreneurs who you feel are great examples of this please let me know. If you don’t feel it’s achievable or have any feedback on the book concept I’d love to hear that as well. These people will serve as a vivid example of what IS possible. You can be very successful while living a balanced life.

Profile (they definitely do not have to be well known--in fact we would prefer if they weren't):

  • Made an inarguably large sum of money (roughly 20 million USD), in a relatively short period of time (10 years)
  • Although they have worked hard and are passionate about what they are doing, they have done so efficiently (roughly 50 hours/week) and have made time for all of the great things life has to offer.
  • They have not had to make the huge sacrifices traditionally associated with this level of success.
  • Likely have very few regrets with regards to the way they are living and exude energy and passion.
  • Maintained thriving healthy relationships with their family, friends and communities.
  • Had the time and energy to pursue outside interests (sports, music, creative endeavours) and live a healthy life.
  • Ethical in all areas, doing great things for society as a whole and be respected by both those close to them and their communities at large.

Choices Entrepreneurs Success Profile

asked Oct 12 '09 at 17:17
Jordan Milne
116 points
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  • I like the question; I'm skeptical about the part where they didn't work too many hours. If you find anyone who is both (a) honest and (b) has no regrets, I'm curious about that too. :-) – Jason 14 years ago
  • Oh, and I think you should add this to your list of conditions: That THEY actually were directly responsible for making the money. Because there's a lot of people who made money because they were "just there," and that's not what you're talking about, right? – Jason 14 years ago
  • Professor X fits the description ;-) – Slav Ivanov 14 years ago
  • Do you think this would open up if we lowered the earnings to 10 million USD? If we did, do you feel it would still be an interesting concept? – Jordan Milne 14 years ago
  • I don't have enought rep to edit, but may I suggest changing your title to "Which entrepreneurs have made $20mill+ in under a decade with a balanced lifestyle?" – John Mac Intyre 14 years ago
  • John-Thanks.I implemented your suggestion with one more detail at the end. – Jordan Milne 14 years ago
  • I'd be curious about how many of the people featured within Entrepreneur magazine meet your criteria. e.g. Markus Frind, Ashley Qualls, etc. – Jay Neely 14 years ago
  • I feel people ask questions like this a lot... like having an ultra successful business can be done in ones spare time. It's just very unlikely. People who make killer companies do so because they love working on their company. They put in a lot of time, and in many cases don't consider it a life / work in-balance. At some point I assume they all have to bust some ass then they can sell out. But, I think it's rare to casually make millions of dollars. – Ryan Doom 11 years ago

11 Answers


Not only is it possible, it's really inexpensive to achieve, too. Here's how to do it:

  1. Work as little as you'd like (50.. 40... 5 hours) all while enjoying all the fine things life has to offer
  2. Buy a mega-lotto lottery ticket on a weekly basis

Granted, it has an infinitesimally small chance of working, but nothing is guaranteed, right?

My point with this is that anything is possible, and that your quest to find said entrepreneur will inevitably show you one thing: there was a lot of good luck involved. That individual just happened to do the exact right thing at the exact right time and was infront of the exact right people to pull it off.

The reason entrepreneurs work so hard and sacrifice so much is because the only way to have a reasonable guarantee of success is to do lots of things (most wrong, some right) at different times (most wrong, some right) in front of all sorts of different people (most wrong, some right).

answered Oct 13 '09 at 00:38
Alex Papadimoulis
5,901 points
  • Actually, most founders work so hard because they have passion for what they are doing and love it. – Tim J 14 years ago


Maybe Derek Sivers?

He sold CD Baby for $22 million. From this discussion in HackerNews, it seems, the business ran by itself since 2002. Of course, i have no idea if he satisfied all those criteria.

I left the day-to-day operations in 2002, and had been living in California and London (while the business is in Portland Oregon). So it had been running without me for 6 years.
Yeah I might have made more if I promised to stay with the company, but that was completely out of the question for me.
There were no super key employees. (Some great people, but everything quite documented so someone new could step into any role at any time.) It was just a working system.
The two main techies were probably the most key in explaining the system to the new techies.
I set it all up this way to give myself personal freedom, but it definitely helped for handing over the keys to the new owner.

answered Oct 16 '09 at 20:11
Hendro Wijaya
1,408 points
  • Hendro-- Great potential example! Thank you--we will look further into his case. Best, Jordan – Jordan Milne 14 years ago
  • He worked his ass off the first few years though. – J Delage 14 years ago


I think its pretty rare. Why?

Because mostly if you are balanced enough to know that work isn't life and you just do business because you enjoy it as a hobby (as it should be done)... then your goal isn't to make $20 million.

I make really, really awesome money doing applications that run themselves. But, well below $1 million a year. Its not worth it. I've made enough to be comfortable and now its less about making more and more about making my life more fun and work on more non-profit stuff, etc.

My point is, if this is supposed to resound with the average person, don't talk about those who make $20 million+ and live on a yacht, talk about people who earn really great livings working 20 hours/week and stay creative, healthy, and moderately successful.

answered Oct 20 '09 at 20:52
71 points


You might want to get in touch with someone like Tim Ferris to see if he could connect you with someone who has used the strategies outlined in his "4hour work week" book to reach the status that you have described above.

However on the flip side I think you may have generalized a whole rich life with your own perspective of what that should mean. I know many ultra successful entrepreneurs who love what they do every day regardless if they have to work 90+ hours a week. The balance they have created in their lives is according to what they perceive to be living a whole rich life and not what society dictates that balance to be.

answered Oct 12 '09 at 17:45
Usman Sheikh
1,728 points
  • Usman-- Thanks for your comment. You make a good point that some ultra-successful entrepreneurs do enjoy working constantly on their ventures and are more than happy to pull 90+ hours. If they love it and are comfortable with that lifestyle all the more power to them! The profiles we are looking for, however are for those who enjoy their business but also want to have the time to pursue other ambitions as well. Both are great, but we are looking for the latter. – Jordan Milne 14 years ago
  • By the way, Tim Ferris himself works all the time... be careful about how literally you take what he says. He defends that by saying "if you're having fun it's not work." Yes, but... – Jason 14 years ago


I've worked at a couple of start-ups for a CEO who uses that philosophy: Family First. It hasn't impaired the success of the company. Now maybe his companies haven't been Googles or Facebooks, but they have been more successful than the average start-ups. Employees have been treated well, and made money on the sales of the companies to larger entities.

I think it is definitely possible. And yes, there is luck involved. But NO start-up is ever successful through hard work alone!

answered Oct 15 '09 at 00:47
Chris Boran
326 points
  • re Alex's comment on luck: I agree with you Chris, in that there is a certain amount of luck involved in any success. It is, however,one of many factors. Its important to acknowledge the role luck plays, however we are looking for profiles of these exeptional entrepreneurs to learn the other actions that are part of the equation. As mentioned, not as big as Facebook or Google, but still big enough to illustrate you can do it all. The goal is find those that have achieved this efficiently. Chris--would it be possible to get the name of the ''Family First'' CEO you mentioned? Best, Jordan – Jordan Milne 14 years ago
  • 20M in 10 years successful or yes we got money let's have fun successful ? :) – The Dictator 14 years ago
  • I don't ask who-got-what, but I do know that one company he founded sold for $300M+ in 1999 and the one for $50M+ in early 2006. And I'll be clear: I'm not saying all of the criteria is met - especially the max 50hr lifestyle, just that family comes first in his companies. – Chris Boran 14 years ago
  • Chris-thanks a lot for the information. Family first is definitely a great priority value. We are however looking for those that have been able to thrive outside of work because their business success has not come in a traditional manner (working exausting hours and sacrificing). We realise these are tricky to find, but that is why their stories will be all the more inspirational. We are looking to prove that you can achieve big success 20million in less than 10yrs working less than 50hours/week. The low work hours is not the only factor, but it is key to what we are looking for. – Jordan Milne 14 years ago


You're probably looking for

And there are many more...
answered Oct 20 '09 at 02:59
Arpit Tambi
1,050 points


I think you are going to find Entreprenurial minded people are workaholics. They think, eat, dream, and sleep their work. They are consumed by their passion and what they want to accomplish. There is no 9-5, 8-6 ideal. Their time clock is 24/7/365.

That being said there is an interesting article written by Keith Hammonds on fastcompany.com entitled, "Balance is Bunk." It may change your perception about the balance issue. Read it during one of my MBA classes at Babson. Enjoy.

http://www.fastcompany.com/magazine/87/balance-4.html Shawn

answered Oct 24 '09 at 03:45
Shawn Flanagan
151 points


I guess YouTube founders would qualify.

They sold to Google for about 1.65 B$ after one year. Although they might have worked over 50hrs/week for 1 year, they can now enjoy the rest of their lives at 0hrs/week.

answered Oct 21 '09 at 08:56
Olivier Lalonde
2,753 points


I think yes it is possible(after an entrepreneur has worked his butts off an idea and made money out of it). After the first time, it must become easy.

answered May 23 '13 at 09:52
Aditya Anjoli
123 points


I am not talking from experience here, but I think it is totally possible. One condition would be that you have a different attitude to growth and size of business. I'm wondering about this myself, but it all depends on how you define "whole rich life" for yourself and then make the decisions needed to pursue that (as hard and un-businesslike as they might be). Here are a couple of blogs I read by people who do exactly this - pursue the life they want and being entrepreneurs:

Location Independent
Art of Non-Conformity

answered Oct 12 '09 at 18:15
316 points


Maybe not exactly what you are looking for but my favorite story is Zynga.
Company founded in 2007 and worth 3 billion in 2009 (2 year span!)


answered Nov 9 '11 at 08:34
21 points

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