I sold my B2B business and achieved my dreamed... meaningless life?

Hey IHers, in the past month I wrote about pre-internet companies. Today, I’m steering and sharing about my personal life, my past experience from building, selling a company, achieving the life I dreamed about and how empty it was.

My lessons learned?

  • Look for a meaningful life, always
  • but health first
  • Time is precious
  • Challenges make me alive
  • Be happy
  • Have savings
  • Money is temporary, spend wisely
  • B2B business is hard. Relationships help a lot


2007 - I’d been working for 10 years in Brazil, mainly as a software engineer and tech lead for a few different software development agencies.

Hectic environment was the norm. 250+ hours/month for 4 months, no weekends, no exercises. I was like: “I’m young, I can do all of it”.


Then, all of the sudden, I felt an irregular heart rate. I felt my heart beating faster for 2 days. This situation led me to a hospital visit. Burnt out detected. I was told to reduce workload. At least, my heart and everything else was completely fine.

This problem would change my mindset forever.


Worrying about my life, I left the company and planned to spend 1 year taking care of myself, no work at all. (At the time I was living at home, no kids, 2 years of savings, which facilitated my decision)

My new mindset

  • I will never work as many hours as before
  • I will not worry about work as much as I will about my health

What did I do next?

2 months into my “forced sabbatical”. Got a call from a former colleague: a job proposal. “NO, I’ll stay 1 year off work”. “How about doing a contract, working from home, at your own time?” I sent my proposal, considering 8hrs/day, higher rates and extended delivery dates. “Ok, agreed”.

Fast forwarding some years, I co-created a B2B product (similar to QlikView and GeckoBoard) at my own pace (10 months), without pressures (working normal hours). Took us 10 months to strike the first sale!

Company of One

I ran the company for 9 years:

  • 3 co-founders, I was the only one - working full time
  • 4 clients only
  • 4 employees
  • All projects had realistic deadlines. We wouldn't allow pressure from clients to deliver earlier
  • No extra hours
  • Flexible time, we mostly could work whenever and wherever we wanted to, following the deliverables

All of it also allowed me to work less hours and enjoy the chased freedom. We were thriving.

Finally, the dreamed life

Everything was running accordingly. No long hours. Holidays abroad. Time to exercise. Low 7 figures revenue. Great profit. Highly efficient employees. The dreamed life had arrived! To make it even better, I received an offer and sold my company for something in the north of 7 times my yearly earnings.

Moving abroad

With money on hand was time for us (my wife and I) to take the biggest decision of our lives: to move abroad, from the hot and sunny Brazil to London (I’ll write another post with the reasons we decided to move).

I’m on top of the world

Now, I have all the time I wished for. I can travel a lot. I don’t need to work. I’m successful, anything I launch will be profitable. I know how to make money.

Then I travelled. I didn’t look for a new job at all. I invested my time in side-projects as diverse as a list of transport options from airports to city centres. List of UK beers. List of videogame’s musics.

Is everything going according to the plan?

Well, my new lifestyle was not bringing me real happiness. Having anything I dreamed of without any clear purpose was meaningless.

Adding to this, my side-projects were not helping anyone. This made me realise I wasn't as invincible as I arrogantly had thought.

The meaning of my life

One of the purposes of our moving abroad, was to raise kids in a safer country, with less problematic politics. Then, sticking to the original plan, it was time to have a baby. He was born 2 years after I started my dreamed, empty life.

Since then, I'm one of the most important people in the world, at least for him. My life now has the most clear objectives, most difficult challenges and the best rewards ever:

  • to make him as happy as possible. If he’s happy, I’m more than happy

  • to raise him without any preconceived views

  • and many, many more

Now, I’m on top of the world.

My today’s world

Since 2018 I'm working as a Project Manager/Product Owner after 12 years as an employer.

Why? My mind needs to be active (empty mind sucks). It makes me feel alive. I need the income.

There are loads of positive points now, like 25 days of holidays, clear direction, having a boss to learn from, working in an industry I’m passionate about (sports), career progression, etc.

My future

I’m chasing the dream, once again, of launching something that helps people. Why?

  • to see the real joy of helping people solve their problems
  • to spend quality time with my family. This time will never come back
  • to have the freedom to work whenever and wherever I’m the most productive
  • To feel the rush when a new client buys my product

Now, I’m 100% sure I’m using my time and money way more wisely than before.

I want to write more articles about product creation, pricing, monetisation, resources management, struggles, sales process (~90 potential clients to 4 sales). Please, let me know if this article helped you somehow.

I also shared this story in my weekly newsletter. Sign up here

Share this story and follow my journey on Twitter

  1. 12

    Still feeling [post-success] meaninglessness?
    I recommend Chapter 15: "Filling The Void" of "The 4-Hour Workweek"

    I'll skip all the good stuff, and leave the action steps summarized:

    • Revisit ground zero: Do nothing (learn to turn down the static of the mind so you can appreciate more before doing more)
    • Make an anonymous donation to the service organization of your choice
    • Take a learning mini-retirement (six months or more if possible) in combination with local volunteering
    • Revisit & reset "dreamlines" (aka things you want to have, be, & do in life)
    • Based on the outcomes of steps 1-4, consider testing new part- or full-time vocations

    "Recapturing the excitement of childhood isn’t impossible. In fact, it’s required. There are no more chains—or excuses—to hold you back."

    1. 1

      Great suggestions, filling the void is absolutely necessary. Retirement is another event we need to pay attention to and plan accordingly. Otherwise similar feeling might happen

  2. 3

    Your story captivated me, I read it until the last word. I don't know you, but I'm proud of you. Also glad that it worked out for you. Thank you for sharing your story.

    1. 2

      Wow thanks for the nice words

  3. 3

    Hey Leo,

    Thanks for the share, I feel like I know you much better now! ❤️

    I was going to take time off after Ministry of Testing, haha, never did. Got the chance to help out here at IH instead and couldn't say no.

    I took a slow path of moving on from Ministry of Testing, it's not always easy to find people to buy a company (I couldn't be bothered to look tbh) nor find people to take on the task running it. I ended up with having someone run it, so I still (co)own it.

    I have to tell myself often that it is no longer in my hands what happens to the company, to detach myself emotionally and mentally from it. It is hard when there is staff and community behind it, but any time I start to get a bit stressed about things that may be happening I remind myself of this. I too had burned out there and I need to learn to survive and be sustainable without it, that way if it all does fail, or I stop getting my income from it then it won't be such a devastating impact for me and my family.

    I was also convinced I no one would hire me and that I didn't really want to be hired, but I'm quite happy now at IH (currently as a contractor) and I'll continue plodding along, focus on slowly growing and doing some side projects (it's hard not to!).

    And like you say, for me it's important that I feel my work is making an impact, it keeps me energised and motivated.

    1. 1

      Nice to meet you @rosiesherry :). I normally don't share personal stories but it made me feel so good because I saw people telling me that my story resonates with theirs, my story helped them be aware of the problems I faced, etc (I should've shared earlier tbh).

      I was going to take time off after Ministry of Testing, haha, never did. Got the chance to help out here at IH instead and couldn't say no.

      Glad you jumped in, this community is growing even better.

      It's a weird feeling to basically, let the company we created and raised, to have a life without us. For you I guess it's even more difficult as you still own it but is not part of the daily operation anymore. Are you of working as a board member for Ministry of Testing?

      1. 1

        I refer to it as being 'on the board'. I'm there to advise, basically. But mostly the decisions are not mine to be made. For better or worse, I have to let it be.

  4. 2

    Great article! Thanks to share that.

    I have three very strong pillars in my life:

    1. Enjoying what I'm doing. It doesn't matter if it's called working, playing, thinking. Whatever.
    2. Helping others.
    3. Leaving the world a bit better than when I found it.

    Business, money and everything else is optional. I always try to focus on the trip. Till now it served me very well. I'm not famous, I don't have a lot of money, but I'm happy anyway.

    1. 1

      Couldn't agree more. I wish I had those pillars before. At least I realised what was missing and now I really know what I want. Happy that you're happy.

  5. 2

    Nice article, with the savings I've got, I figure I could live for the next~30-40 years without working, but it gets really boring and empty real fast. Definitely thinking about open-source projects or something with long term potential like social networks for professional niches, that can bring more meaning to work as you can give back and grow a community.

    1. 1

      Agreed. Creating a niche community for x is a way to give back. And you're right, don't feel tempted to stop working and do nothing. It's the worst thing ever

  6. 2

    Thank you for sharing this very personal story. I would love to read more of this.

    1. 1

      Glad you liked it

  7. 2

    It's so easy to think of financial success and security as the end goal, but stories like yours make it so clear that the journey is often just as important (often moreso) than the destination.

    I had an accounting professor in college who struck it rich in his early twenties by investing in real estate. He ended up trying to become a professional golfer, going to art school, and doing a bunch of other random things in his attempt to replace the purpose that had left his life. Ultimately, he was only able to do that by doing things that directly helped others, culminating in him becoming a teacher.

    Thanks so much for sharing, Leo.

    1. 1

      Thanks Jordin. The more I read the more I see cases like you said.

  8. 2

    Nice to hear your thoughts on this topic. I definitely agree.

    One quote from Jerry Seinfeld is that he "learned to love the process". So he's rich AF but he still 'works' by making comedy. He found his purpose. I feel like my views are changing in that direction too.

    I used to be all about the FIRE movement and thought an easy life without work would make me happy. But after a year off I found myself still coming up with ideas and building things.

    I realised that there's no end. My goals will change, my purpose will change, but I should learn to love the process.

    1. 1

      Yes, I understood where loads of rich people like Seinfeld still work. Obviously the first sale, first 10k, better car, etc will make us happier, but it lasts for a few moments only.

      Yes, one can't stay idle, without doing anything. For me, this is not the way I want to enjoy my life.

  9. 1

    Great story! Thanks for sharing and I bet I have lots of things to learn from you.
    One question: after all those years of being an employer, how does it feel now to be an employee (following rules, having a boss and such)?
    Why didn’t you start a new venture instead of working as an employee? (I understand, you tried to start and they’ve failed but still.. you could have partnered with someone etc.)

  10. 1

    Thanks for sharing!

  11. 1

    @Leo, se quiser, entra no nosso telegram para brasileiros: Indie Hackers Brasil https://t.me/joinchat/BK3yHk468gSq1OuvJTRh9w

  12. 1

    That's such a great story and you've done so many great things, whether it's in career or in personal life!

  13. 1

    Great article!

    Why? My mind needs to be active (empty mind sucks). It makes me feel alive. I need the income.

    With the savings from selling your previous business, do you actually need the income to support the family? As an alternative, you can invest and live on the investment returns. Right?

    1. 1

      Hi Junji, yes I need to. To summarise, when I sold it, I hadn't had any extra income and my expenses were pretty high, therefore I spent the most of it. Now, another lesson learned for me: to think of leaving the 9-5, employee situation, I'd need an extra income of, at least my monthly expenses.

  14. 1

    Really good stuff, @Leo - thanks for sharing

  15. 1

    I read this post twice. Why? Because I had to, I needed to. That's how great it is.

    Thanks for sharing your story in such an honest way. It summarizes important life lessons and wisdom I wish I had ran into when I was younger. However, it's never too late to learn and to become a better version of yourself. And this is just another piece that will help me in my life path...

    1. 1

      It summarizes important life lessons and wisdom I wish I had ran into when I was younger

      Me too haha. Seriously, those messages make me wanting to share more and helping more somehow.

  16. 1

    Wow, it was awesome to read somebody that got across the life which every Brazilian dreamed of and, still, being so humble. All the examples I have until this was people that get even more arrogant, building their audience talking fluffy things about how to get there.
    This fulfill my heart of hope and makes me believe one day I would archeave success and still being the person I am.

    1. 3

      Thanks for the message. I feel connected with IH community, as I've seen so many people sharing honest messages, struggles and everything in between. I couldn't hide anything as for me, my main focus is the make people aware of what we dream about and have a good and solid foundation

  17. 1

    Cara great post! Indeed you need a goal or your life might feel empty
    Making money is exciting, having money is actually boring (but, let's face it, useful)
    Have you considered moving to Lisbon? It's safer than Brazil (hell it might be even safer than London) but weather is so much better... Been here for 5 years now and loving it

    1. 2

      Thanks, yes money is useful for sure, we only need to make good use of it.

      Every year, especially during winter I consider moving to Lisbon ahah. But at first, another reason that made me move to the UK was to learn English

  18. 1

    Great story, I am glad you're happy dude!

  19. 1

    I enjoyed the article, Leo. Thank you for sharing.

    It's so easy to caught up in the day to day. This is a nice reminder that I always need to keep my priorities straight in building my meaningful life.

    1. 1

      Glad you enjoyed. Happy to bring some awareness to this problem. More and more, people are telling me they had the same problem

  20. 1

    Great post & inspiring. Now, we want to know why you moved from a beautiful, hot and sunny Brazil to London :)

    1. 1

      As a Brazilian guy that's still leaving in Brazil, I couldn't agree more with Leo about moving abroad. To not talk about our political issues, the lack of security and education are the most reason why, at the first chance, we run away from here.

    2. 1

      In summary, being in a safer place, to raise kids without the fears we used to have and the fact that's way too complicated to do business in Brazil. But beauty-wise, incredible country to visit! No doubts whatsoever

      1. 1

        I've visited Brazil three times, and have helped many brazucas move to Canada. 🙂

  21. 1

    Thank you for sharing this experience, some of us are treading on the same path as yourself and this definitely gives us the reason stop for once and take a break.

    1. 1

      I glad my story is helping and bringing awareness to some

  22. 1

    Leo thanks for sharing! I sold my share in the company around 8 months ago, sometimes I feel I am drifting in an open ocean, I work on something else, but I don't know why level of the motivation and excitement is not the same. Thinking about that the whole day, why I do work halfheartedly now.

    1. 1

      In my case, I understood what really excites me, which is making others happy and being helpful in any form: giving suggestions, listening to their problems, creating products to help people, etc.

      What brings excitement to you?

  23. 1

    Very interesting perspective. Thanks for sharing!

  24. 1

    Thank you for this small reminder to stay healthy. And the inspiration to keep going🙏🏼

    1. 1

      Yes, that's a very serious problem.

  25. 1

    @Leo Loved this write up. Keep writing here.

  26. 1

    I believe it might have something to do with not feeling challenged anymore. What about picking some entrepreneur and trying to make them succeed?

    1. 1

      I should've done that. My wife told me a few times about it. I'd love to do it.

      Problem at the moment is: I don't have experience building any "modern" company. Mine was built in 2008, different situation, B2B deals in Brazil were made mostly via relationships, etc. What I could do is write more about how I did things like, how I created the product, my pricing strategy, etc and then try to help some entrepreneurs using it.

      What do you think?

  27. 1

    This definitely helped me. I can relate to the burnout and then suddenly realizing that health is very important and then taking time off to take care of myself. Except in my case, things went downhill from there :)

    There are other things in your message that spoke to me. If you have a website/blog, please let me know. I'd probably like to drop in every now and then to check out your writings.

    1. 1

      I'm so happy it helped you somehow. I used to feel guilty of projects being delayed....obviously I had to change my mindset, and not worry too much but it seemed impossible to me, until the burnout.

      I wrote on my personal website but I'm most active on Twitter. Feel free to DM or email me

      1. 1

        Yeah, mindset is key, I've come to understand that as well in the past few years :)

        Thanks for that! I'll check it out.

  28. 1

    This comment was deleted a year ago.

Trending on Indie Hackers
Finally, I think I've got a good idea 17 comments How do you read this logo? 17 comments Former Head of Growth at Morning Brew (3m+ subscribers), now running media consultancy. AMA! 10 comments Find SaaS Ideas #0015 7 comments Building a course to help people level up their Software Engineering careers, what do you think? 7 comments 6 Simple steps to validate your business idea 1 comment