I left my high-paying job, bootstrapped, burned, joined back job after 3 years. Ask me anything.

A lot has been said about overnight successes, thousand of dollars in MRR, and millions of dollars in acquisition. But if you are looking to quit your day job, it's important to know the other side of the story and failures.

I left my job at a Fortune 500 company in 2016. Bootstrapped as a solo founder, scaled it, growth hits the wall around 2018, and I called it quit in 2019. Took a job, and now after 2 years things started looking stable in my life.

I am open to questions, ask me anything.

  1. 9

    Thanks for sharing your story!

    I can relate to what you've said. I went through something quite similar and have recently put my first SaaS startup project "on hold". I wrote about it a while ago: https://medium.com/swlh/20-months-in-2k-hours-spent-and-200k-lost-a-story-about-resilience-and-the-sunk-cost-fallacy-69fd4f61ef59.

    In June, after two years of hard work and many sacrifices, I've realized that it really wasn't going anywhere. I started working again as an employee (half-time) in order to be able to pay rent. It was a tough decision to go back, but it was the safest for my family. I wanted to build my own thing, but never to jeopardize our quality of life.

    Now, a few months later, the pain slowly fades away and I'm working on a new project. I clearly needed some time to recharge. I don't want to quit just yet, because I really can't picture myself going back to my previous situation, I see the current state of things as transient. My old job/life was VERY comfortable, but also dissatisfying professionally. I've come to realize that I really enjoy building products and working on my own terms. We'll see how my second attempt goes, but this time around I won't wait two years to try something else.

    I think that my current approach is a good middle ground: safe/stable for my family, while still giving me a chance to evolve towards a more (personally) fulfilling professional life. It's quite tough because I need to switch contexts regularly (freelancing ~1 day per week, 2-3 days employee work & the rest for my own projects), but it's better than nothing.

    1. 3

      Wow. That was a good read. There are tons of failures in world of bootstrappers also, but somehow those stories don't get highlighted. I learned a lot with my failure, I am a better person because of that experience. I initiated this thread with hope to help people who are in similar boat. There was some very stressful time, including when searching for job.

      Now looking back, I take all those experiences with smile. :)

  2. 5

    Thanks for sharing. If you're open to it, what did the financials look like for each of the 3 years?

    A few businesses are clear winners or losers in the first months or year, but it seems like many more of us have a slow first couple years where the numbers show some promise, but are not great yet. You never want to stop too early, but it can also be a trap where you work for another year without much change in the numbers and always chasing one more item on the todo list.

    1. 4

      I was slightly profitable in all 3 years, but not enough by end of it to pay myself well. Going beyond this meant 3-4 more years to make it worth, and thats when market condition remained same (I am thankful that these decisions were taken pre-covid. it would've been a very tough road otherwise)

      Any business will take 3 years to show result, considering consistent efforts are made. Does not matter how much effort you put, time plays its own role. With first one being very dull. I confirmed this with multiple founders, and observed quite a few indie businesses. All are showing good profitability in 3rd or 4th year.

      1. 1

        How much was your business making per month or year? And define 'good profitibility'. What is that to you?

      2. 1

        I agree with this. Even though I saw traction in my business in the first 2 years, only in the third year did I feel like I can start making it sustainable i.e. paying myself and my team fairly with no immediate threat of going out of business.

  3. 3

    Thanks for sharing this publicly. I have been there before, and it's hard.

    I quit my job to start a consultancy with 2 other partners. We ran it for 5 years until we got hit with a series of perfectly timed unfortunate events going into Q4 when not many new projects start. Our sales pipeline was dry and we were burning cash. We wound up having to lay everyone off, shut the whole company down, and all go get regular jobs. It was one of the worst feelings in my entire life. I also got hit with a $26k tax bill from that year's earning that I couldn't pay. I spent the next year on a super strict budget working to pay it off.

    I made it out the other side okay, but I was in a weird mental state for several years where I was totally burned out and just wanted to be a FTE at some other company instead of doing my own thing for a long time. It was a good move both for me and my family, and provided a lot of stability and good income.

    I am on the other side of things now where I am beginning to work on my own things again. You'll be okay. Just take your time! :)

  4. 3

    Thanks for taking the time to share your experience - really valuable.

    1. First of all: How do you feel now?

    2. Looking back, why do you think was the main motivation to start a business?

    3. Do you see your 'life project' differently now?

    4. Would you still pursue on building your company if you could go back in time (and maybe tweak the business, or adjust to overcome the roadblocks in the growth) would you do it?

    1. 1
      • First of all: How do you feel now? Looking back at the experience, I am happy about what life skills this gruelling experience has taught me. I am stronger mentally, and more logical in decision making. This experience will be with me for lifetime. I had my first child, and enjoying every moment of it.

      • Looking back, why do you think was the main motivation to start a business? Growing at my own terms. As everyone, I felt my potential was untapped and I should do something bigger.

      • Do you see your 'life project' differently now? Yes. I started enjoying day to day moments. Taking things more easily, and not rushing through it like a race. I realised after a certain point financially, relationships are the only important stuff. Trying to have a good social circle I can talk to.

      • Would you still pursue on building your company if you could go back in time (and maybe tweak the business, or adjust to overcome the roadblocks in the growth) would you do it? Not the same Idea. The path I was in was not very scalable, and making money would mean sacrificing on time. I am open for any other Idea that comes my way, and would be more focussed on meaningful problem.

      1. 1

        Thanks for the candid feedback. My main takeaway from your journey is that it is a very lonely and specific path for each entrepreneur and there’s no right or wrong - therefore you better off trying

  5. 3

    Did you ever try to bootstrap another project after this one started to stall?

    And did you have any dependents that influenced your decision to return to a stable job?

    1. 9

      I was not able to start any other project because it was mentally very tough to start all over again. There were lot of things to deal with, biggest one was maintaining constant cash-flow (it was bootstrapped, and only real customers could make it survive). I was working almost 16 hours a day without break for almost an entire period of 3 years. It was heartbreaking to see things falling apart, and scrambling through all this was difficult mentally.

      Yes, I am married and it influenced my decision. My wife was very supportive throughout, financially and emotionally. Few years down the line, I started seeing my decision impacting the quality of her life, I was missing important moments of my life because of all this work, and that was a trigger point to not go further in this direction.

      1. 2

        That makes a lot of sense, and I totally see why going back to a day job was the right decision!

        Was it a subscription based business? If so, I was under the impression that the revenue is a lot more stable from those. If it was SaaS, did you have high churn or was it just hard to get customers in general?

        Lastly, did you choose to quit after a side project was starting to show results or did you start from a blank slate? From your reply, you probably don’t have time to do a side business on top of your day job but apart from that, what are your thoughts on doing both a day job and a side hustle to check if there’s an audience?

        Thank you for doing this AMA!!

        1. 4

          It was not Subscription Model. Revenue was there but lot of fluctuation. So yes, SaaS will have a good predictable recurring revenue.

          I was running it for some time and by the time I left and It was slightly profitable when I left. One mistake I did after going full-time was not to pay myself, and invest back in business to grow faster.

          I am now a strong believer that hustling along with full-time day job is doable. Technology is cheap, talent is available in form of gig workers. By staying in day job, you have two main advantages:

          • Network of colleagues in day job. You need them for just casual chat or when you need some serious help. It's a lonely road building a business, and as soon as you leave those connections fade away because people see you differently.
          • Constant income you are getting will keep you confident taking bold steps in business, like investing for growth. In most of the indie businesses you should be able to hire 1 person to do all time consuming stuff, letting you focus on important things like product, ideation and sales. All this without impacting your lifestyle or stress of making money.

          Leave your job once you start paying yourself (this should hit your personal bank account) equivalent to day-job, and hustling become too difficult. Only when both condition satisfies, not one.

          1. 1

            Thank you for the note about coworkers! I had not considered that, but that makes a lot of sense.

            Thinking about the best way to side hustle + day job.

          2. 1

            That’s true, I hadn’t considered the value of work connections.

            Thanks for sharing your experiences @curiouspm. Super helpful thread!

      2. 1

        What were you mainly doing in those 16 hours?

  6. 3

    I've got a few questions:

    Why did you quit the startup?

    Are you considering bootstrapping another startup? Or have you decided that it's not for you?

    1. 4

      When I started working on it, I made two mistakes - not doing financial planning in advance (milestones and runway) and not having a support system to fall to (community, network, strong family support...). In a startup, 100 things fail and then you get a small win. Then again 100 more things fail, and again a small win. I was pushing through all these failures without thinking much. And then came a time when both of my mistakes confronted me. My savings dried up, and I had only my wife to discuss all the issues and problems in business. She was very supportive, but I could see the stress of all this on her face. It was time to quit.

      I will probably consider another bootstrap project(s), but without going full-time into it. I never wanted a billion-dollar company, but a lifestyle business that gives a sense of purpose, learning, and making money along the way.

      1. 0

        "Then again 100 more things fail, and again a small win" - I am building a product to help people go through exactly that. Chatting with you will really help. Can we do zoom?

        1. 1

          interesting. my comment was more of the general founders' path because of uncertainity in the business world. would be happy to help, just drop me an email.

  7. 3

    In your opinion, what's the best thing that happened to you during that time that you attribute to luck, or chance or coincidence?

    1. 7

      I had a shy and introverted personality. Going solo made me push my boundaries in areas I was not comfortable with - talking to businesses, negotiating, selling, providing customer support, marketing, thinking in terms of business to make money (not a hobby project). This had a huge positive impact and I can see the difference after joining back the corporate job.

  8. 2

    Thanks for this sharing. Was the problem you were solving a problem that you experienced yourself before you started the company or is it a problem that you found while researching?


    1. 2

      Nope. It was a new problem I found while researching. That made it more exciting for me, as I was in a completely new territory coming across new learnings every day.

  9. 2

    I can relate. I'm probably on my way back to the corporate world myself. I have mixed feelings but for the right role I will look at it as a step forward.

    It doesn't have to be a binary thing where either you succeed with a startup or fail and go back to a job you hate. For me - a side effect was up skilling in full stack development and I hope to leverage that in my next role.

    1. 2

      This is so true. For me startup experience helped me grow in areas I would've never entered.

  10. 2
    1. If money wasn't a factor at all, would you still go back to a job, or try and startup a different business?

    2. If you were to go back in time right until after you quit. What would you do differently?

    1. 1
      • If money wasn't a factor at all, would you still go back to a job, or try and startup a different business? being in a day job has another overlooked advantage, a network of smart colleagues you can talk to. I am intrigued by the idea of micro-startups popularised in recent years. You get all the advantages of running a startup (excitement, ownership, learning, finance etc.) with relatively low overhead (time, money, employees, compliances etc.)

      If you were to go back in time right until after you quit. What would you do differently? planning well ahead in time and focus on core of problem rather than focusing on growth first.

  11. 2

    Thanks for being so open and honest about this.

    Why did growth hit a wall?
    Where did you get to MRR-wise?

    1. 2
      • Why did growth hit a wall? My analysis is the market size was limited in what I was doing. I was ignoring this signal, estimating it would grow.
      • Where did you get to MRR-wise? It was a decent number. I am intentionally not disclosing details because want this thread to be a general template for all others like me. Once I disclose the number, a lot of people will start relating things and making assumptions. :)
      1. 1

        The number ballpark is very interesting to some of us, because people have very different views on success. Some people's failure is another person's success

  12. 2

    First, I want to say that I understand you and support your decision to stop the business. If the level of stress is affecting you and your love ones mentally or physically, quitting is the best choice.

    I have some questions:

    • You mentioned your savings dried, that means you business wasn't profitable or non-stable?
    • What would need to happen now to make you want to start again? or you discard it for ever?
    • What would you different on a new business?
    • Working hard is just a myth? what are your thoughts about it?

    Thanks for your time Curiouspm

    1. 2
      • You mentioned your savings dried, that means you business wasn't profitable or non-stable? money was going toward working capital, future growth investments, compliances. lot of money just stuck and not accessible. I understood first-hand what cash-flow means.
      • What would need to happen now to make you want to start again? or you discard it for ever? I am going through couple of ideas, but nothing stuck that make me work towards it. One thing for sure, I will minimise the risk this time (even if that means less monetary returns)
      • What would you different on a new business? keep things simple, focus on actual product-market fit before jumping into growth and investing too much time.
      • Working hard is just a myth? what are your thoughts about it? consistency in right direction is more powerful than hard work. we are living in amazing time, technology is so accessible to build businesses. so before jumping into working hard, plan the objectives/goals and then work towards it. 2-3 hours a day, everyday, is good enough to build a business. I can vet for ideas in book 4-hour workweek. I read it last month only (though never picked it up thinking it's just marketing gimmick. but if you ignore "4-hour" part, ideas are practical)
      1. 2

        working capital
        vet for ideas in book 4-hour workweek

        I don't think you disclosed the nature of the business in this thread, but these phrases make me think the project was at least somewhat capital-intensive with an administrative/regulatory burden.

        In retrospect, would you say you picked a business concept that was bigger than the sweet spot for indie hackers? Are you targeting something lower-touch/smaller for your next attempt?

        I'm currently working on positioning my next project, so this is a salient lesson for me.

        1. 2

          You are guessing it somewhat right. I am intentionally not disclosing the details, so to make this thread serve as a general template. Fundamentals will always be the same.

          If I look back now, it just didn't work out. It had all the elements to be worked on by an indie hacker. I was not able to understand it well, and thus overinvested in terms of resources to grow faster and hence all those issues.

          As for advice to you, keep things simple. Check the resources you have in terms of Time & Money (create some kind of plan), and grow in your capacity. One of the mistakes I made, that I was moving on the power of sheer will, with very little planning or knowing my limits.

          The interpretation and question by you were really to point. If this is your first attempt as an Indie, you have good business acumen. I knew nothing when I started. All the best.

          1. 1

            Thanks for the follow-up, @curiouspm. I need to pin a banner saying "keep it simple" above my desk. :)

            It really sucks the project didn't work as you'd hoped, but I appreciate you sharing what you've learned with the community. I think survivor bias can give us all rose-colored glasses. Thanks again

  13. 2

    Thanks for sharing your experience! What promotion strategies did you use for the initial scaling and growth that were most effective? And how many pivots did you go through before terminating the project?

    1. 2
      • Partnerships work really well.
      • Asking customers for referrals show amazing results.
      • Your organic presence online (having an audience) works.

      Paid acquisition burns a lot of money because thats the easiest channel for every big and small, funded and non-funded companies.

      Tried to pivot in very end, but as stated earlier I was out of energy to push through.

  14. 2

    What was the key factor that made you quit in 2009?

    1. 1

      I was at the job for more than 5 years. Things started looking stagnant, felt that I can take up more challenging things in life. Had a couple of small side-gigs in past, but never went full-time. So this time, I decided to do it seriously by going all in.

      1. 0

        I meant to quit the bootstrap game and back to job again in 2009

  15. 1

    Sorry to hear that and glad you're doing great now. Thanks for sharing. Do you mind sharing what you have built and how it was not a market fit / reason you chose to not continue with?

  16. 1

    How would you have prepared yourself (financially, mentally, etc) differently if you were to start another business again?

  17. 1

    Thanks for sharing this @curiouspm Respect your open-mindedness

    1. If you could have done it differently, would you choose to have a full time job and bootstrap your startup?

    2. What would be your advice to first time founders?

  18. 1

    Nice post!
    Based on your responses I could understand the following points:

    1. Understand the cash flows of your idea.
    2. Focus on core problems rather than growth/marketing too early.

    Is there anything you would like to advise on this or correct the above statements?

  19. 1

    Wise and relatable.

  20. 1

    this is an awesome story, such an inspiration.

  21. 1

    Thanks for posting. My story is very similar to yours, I left a Fortune 500 company and in a few months will be at 3 years of my bootstrapped journey. I have revenue and customers, but I continue to have doubts about the viability / scalability of my business (cash flow, like you said, is an issue). I would love to compare experiences - will send you an email.

    1. 1

      sure. would be happy to connect.

  22. 1

    How did the project start? Was it successful from day 1? I mean the launch of the product. How did it start?

    1. 1

      It was a hobby project at first and got some traction. I won't say it was a success, as stability was the fight from day 1

      1. 1

        Do you think it would be wise to quit much much earlier? Scott Adams (Dilbert) wrote about a pattern he noticed was: "Things that will someday work out well start out well. Things that will never work start out bad and stay that way".

        1. 1

          No. I gave up only after giving my 100% and trying out all possibilities. I do not agree with the quote, things are very different in business. I've seen table turn just because of sticking to it. As someone said, “An overnight success is ten years in the making"

          1. 2

            Interesting. His quote is related to the start of a project. It's not about overnight success! That's why I have asked you about the start of your project. According to your answer, it was a fight from day 1.

  23. 1

    This comment was deleted 4 months ago.

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