If you think it is hard to be an entrepreneur, you should try bootstrapping

I met with 2 entrepreneurs from the Microsoft Accelerator last week for lunch. Both are among the nicest people I know.

The first entrepreneur used to have a really easy job at a large technology company. He had a 9-5 assignment and as comfortable a life as you can imagine. Great pay, good work-life balance, and a family that was very happy and content. A year ago he decided to leave and start his own company. He asked his spouse and a close friend to join him as well. They are among the best developers, architects and engineers I have worked with given how diligent, thoughtful and industrious they are.

The first 4 months were spent trying to better identify the problem they were solving, which is one of those that’s really easy to explain, but hard to pinpoint. Meaning, the problem when articulated, was one of those which has everyone go “Yeah, that is a problem”, but when you dig deeper after 30 min, there were many workarounds that people had already figured out.

They struggled and pivoted, changed course, modified their release plan and kept brainstorming, talking to each other, seeking advice from many people and finally released an absolute dud of a alpha version. I used it and I am not sure what it did.

They changed course again. Over the next 6 months, they hunkered down, painfully pivoted and modified their goal posts again. Released a beta version, which most people went “huh?”.

I personally know that even if they did not succeed, they were so good that they’d get a job at any large tech company in a matter of a month. They were that good.

I was happy that they persisted though and secretly hoping they release a product that everyone of their critics would go “Oh wow. Like wow. Really”.

They left the accelerator a few months ago. The last 3 months had been the most painful he said. He had so many fights with his wife, his father, his co founders, family and many sleepless nights, that he was extremely tired and at the point of giving up.

The team stuck through the lows and kept trying to find a way to solve the problem they felt was rather important to solve.

When he met me last week there was a man I met who had been to hell and lived to tell the tale.

They had just raised $800K in funding (money in the bank, yay!) and had commitments for another $200K.

Then he mentioned how he endured the lows and the number of days he cried and wept himself to sleep over the last 2 months,

I could relate.Β Those are exactly the set of emotions I have been through many times in my life.

The first 6-12 months of your bootstrapped startup are hard. If you think something is hard, take that and multiply it over 100 times, and imagine doing an alpine, freestyle, obstacle course avoiding maneuver on a double black diamond. It is that hard.

The worst part of the journey is the emotional roller coaster.

The downs, the further downs, the abyss and the chasms. There is no up. A “down” actually seems like an up.

The second entrepreneur’s story is more poignant.

I met him 8 months ago when he was introduced via a mutual friend. He was a very experienced trade professional with over 20+ years of successfully running his own company, but not in the technology space.

Here was a man, who had made good money, built great relationships and had some excellent success as a services professional.

He and his American co founder then decided the future was in building a product. The only problem was they were not developers or technical people. They had to hire a team of technology experts to build their product.

They were bootstrapped as well. He and his wife, put their life savings into the product. His co founder moved from the US to his homeland to reduce costs and they started building their product. His co founder continued to talk to potential American customers remotely and keep them excited about the opportunity.

They did get a “verbal commitment” from angel investors in Hyderabad, who backed off at the last minute. They had been bootstrapping for over 21 months.

The most amazing part was their customers were so excited to use the product, some of them gave an advance (small amounts of money but real hard cash) for their product.

Since they were not technical experts, they made many product mistakes. They underestimated the amount of time it would take, they put a really bad user interface together which most people could not figure out and they also hired wrong.

The most poignant part of the story was when he told me that his wife and he had to move apartments 3 times (that’s 3 moves) in the last year just so they could keep reducing their monthly burn rate at home.

Imagine moving kids, your wife, uprooting your family so many times so you can follow your passion.

He caught up with me to tell me about their seed round. They just closed $500K with a commitment for another $1 Million from investors outside India.

To them and all the other entrepreneurs who have endured these and many worse things, there’s nothing more I can say. I am just in awe.

When you could easily “get a simple job” and “enjoy life”, you chose to take the road less traveled and the harder path.

There’s another part of the story I want to highlight.

These stories are ones that ended on a happy note – well they both got funded.

For every two of these entrepreneurs, there are 100’s I know whose story did not end up with funding.

It ended with a company that closed, or a marriage that fell apart and a kid that had to go to a tier 2 college, because they had spent a lot of their life’s savings in their startup.

To them as well, I say “you tried, and did not succeed, but you did not fail”.

Those who “failed” are the ones who did not try at all.

The ones who failed are the ones in a safe job, 9-5 assignments who keep telling me “they want to start a company some day”.

I think we should have entrepreneurs that succeeded and those that did not succeed.

I liken it to giving the gold for the successful ones and silver to the unsuccessful ones.

The ones watching on the sidelines and commenting are the ones that “failed”.

28 thoughts on “If you think it is hard to be an entrepreneur, you should try bootstrapping”

  1. Also, there are degrees of ‘not succeeding’.

    With my non-profit venture, I dreamed of funding 50 surgeries every year, then 100, and eventually 500.

    In 10 years, I’ve (only?) managed to touch 114.

    Success? Failure? The answer often depends upon the mood I’m in. πŸ™‚

    1. Hello Dr Mani
      I am a liver transplant surgeon, and am trying to identify funding options for some of my patients who are unable to bear the costs either of a transplant or of surgery for liver cancer. I’d be very interested in knowing more about your startup, and finding ways in which we could potentially work together . My linkedin profile is as below.


      Best regards

  2. “I liken it to giving the gold for the successful ones and silver to the unsuccessful ones.
    The ones watching on the sidelines and commenting are the ones that β€œfailed”.”

    Amen! But knowing this does not make the hell any better unfortunately.

  3. Much needed words Mukund… down in the tranches here, hope is a scarce commodity and morale plays hide-n-seek…

  4. Mukund,

    Suppose you have an entrepreneur can fund himself USD 1Mil (with plenty to spare) and he is willing to lose it all and another as described above… gets a funding of USD 1Mil .

    An interesting question is who is likely to be more driven and seasoned… is it the latter and does it also imply his chances to succeed is also greater.


  5. Thanks Mukund, very inspiring. Sometimes you get so used to looking for light at the end of the tunnel that when you have a cushy job you long for the life inside that tunnel πŸ™‚ Happened to me twice, and am back in that tunnel again and wouldn’t have it any other way. I’m stupid enough to believe that the light isn’t about getting the funding, it’s making a successful business, and then not having to worry about money for food, shelter or kids education for the rest of your life.

  6. Amen! Well said. My husband often says, “Failing steals the reputation of quitting. Failure is a stepping stone to success, and you only truly fail when you quit.”

    My own thoughts are that it’s not what job you’re doing that defines whether you’re failing or not, but whether you’ve stopped dreaming. I used to asked people two questions – whether they liked their job, and if they had unlimited resources and could pick anything to spend their life doing, what would they do. I finally quit asking because the answers made me sad. By and large, the people I asked who worked at a job that was the same day in and day out would answer that they didn’t really like their job, but if they could do anything, they’d do something similar to what they were doing now, although perhaps with more pay.

  7. Have lot of thoughts in mind. But not able to work on that. If possible , need some guidance . Will you provide me some time ? Please only once.

  8. When a friend of mine called to work for him 8 years back, I was working for a MNC, living with hope to build a product, I jumped over, excited that I came out of corporate, could build over my venture by helping him and building my product. Then the things slowly get changed, I become employee for my friend, done some great work that brought them series business, almost 100% company is stand on what I did as products, however the gap between us are widened, I stayed as an engineer, he is a CEO, I got deep into building frameworks, then married, now father of 4 years kid, house EMI, then faced many situations that raises eye balls for why being with them, now I been asked to continue with small stake, that is kind of sabotage for rest of the life. I refused, I walked away, still working as part time contract rather than full time, which I must have done 8 years back. I have to do this, to continue supporting my family, EMI.

    Now only have smallest capital which I had 8 years back itself, working as there is no way. To look back, I was working for my parents, spouse, then for my home, now for kid, this would never change if I am into same kind of job. I might have little more money, eventually buy a little expensive land, pay EMI, life will go for that. When I had this realization, I cried over, heart-broken, there was no go. I was living for months like dead, the biggest pain in the life is losing the identity, for not being self, it is not how others treat you, but it is about how do you feel yourself and what you want to be.

    However my inner voice keep pushes me, I should do this. Now we have 4 months old start-up, get some shape on product which I had in mind 8 years back. Last week, we signed our first customer, it was just RS 1000 per year (we made it lowest, as we want to prove that we do something for someone a (stranger) customer could pay for as a product). This customer, we never seen him, no reference, just contact via mobile. But he agreed for RS 1000 deal, sent same, I have seen 1000’s of 1000 rupees, given, taken and spend on dinners and beers, but that 1000 cheque brought my life back to me.

  9. Thank you for this post Mukund. Sometimes all it takes to get a boost is to know that you are not alone – in your ideas and goals you may be – but not in the situations of life at least. Thanks!

  10. That’s awesome.
    In my case I had to move my family to my home town and living off with 2500/- per month
    We have been boot strapping for 15 months

  11. Hi Mukund

    Please tell the second person you narrated about that he is already successful. Having an understanding wife who is with you through your ups and downs, moving houses three times in a year and that too when you have a kid is a sign of a very very successful relationship. I think even if he fails (god forbid) in his entrepreneurial journey, it does not matter. At the end of the day, a wife that truly understands you and who is with you is more than a billion dollars. And i am sure with that support, he will surely succeed some day.

    Please do convey my thoughts to him.

  12. I agree with the underlying idea that “you can’t win if you don’t play”. Too often we perceive opportunities but do not pursue them, for fear of losing what we have – basically, too chicken to chase the dream πŸ™‚ And I do hate naysayers whose primary argument is “how do you expect to unseat from the market”. The assumption that incumbents will always continue to retain their positions may be correct in the short run, but not in the long run. And if you are not part of the short run, you are not going to be around for the long run. It takes a lot of courage to give up a ‘safe’ job and try one’s hand at entrepreneurship.
    That said, I think you need a good mix of entrepreneurs and employees. Funding is perhaps the first milestone in a startup’s journey. When you start to scale, you need people who are happy to hold a salaried 9-5 job and contribute to the venture’s growth. Wouldn’t it be great if the ‘right’ sort of people self-selected into entrepreneurship and the ‘right’ sort stayed put at their 9-5 jobs? Don’t ask me what ‘right’ is, though – I’m still looking for answers!

  13. Very Encouraging , in fact we are in the process of execution of 3 big orders and largest of its type , 2 completed , 3 rd on the way , its really painful and rewarding too

  14. Very encouraging article, I personally have been a working professional for almost 2 decades and decided to plunge into the entrepreneurial world. It has been 18 months since I started and have been bootstrapping the business in the hope the I will get funded. Still persisting because I strongly believe that I can succeed. We all know that 1 our of 100 get outside funding and I think funding should not be something to measure success. Yes adequate funding is necessary for scaling up and building what you want to.
    Keep going guys..

  15. Hello Mukund, A really great article! I don’t know whether to call myself lucky or unlucky, but I have not gone through the financial part of those struggles (sometimes I feel it is essential to go through that). I am currently involved in two business, one established and one in the startup phase. I want to start another company and would like to fund some of those ideas and find some co-founders who can be almost as passionate and driven about them. After several attempts at validation, I have concluded the only way to really validate them is to start, but find myself short of co-founders. I could recruit someone but I am not able to find anyone from the job market willing to take co-ownership of the idea.

    Firstly, do you think this kind of model can exist?
    Secondly, where do you think I could find some passionate co-entrepreneurs (maybe out of the 98%)?

  16. This article went through my heart! great checksum Mukund. I must say this is the story behind every “Entrepreneur”. Success or failure doesn’t matter. Lessons learned & Experience gained through entrepreneurial journey improve the way you look at your life. You start understanding relationships with more matured way. Money can’t buy everything but you start understanding importance of having money when its needed most. 2 years of entrepreneurial journey teaches you so much than even 20 years of job may fail to teach!

  17. Written in a beautiful way, if “pain” was to read this story would struggle to find himself..
    I believe entrepreneurship is a way of life and this way there is a life long learning & exploring .
    “Failures are the not destinations they are the daemons that are WALLS in your way to success.”

    Entrepreneurship is a subject that must be taught & practiced in schools and kids must be taught how overcome a failure.

    If your close ones supports & motivates you during your hard times, then there is nothing stopping you.

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