The hard things about bootstrapping a startup

You owe an answer to nobody

When you don’t have to answer to anybody, your confirmation bias can take you down to dark alleys with dead ends. You do something because you think you are right. When you don’t have to answer or defend, every realization comes after execution and not through borrowed wisdom.

You are not in a hurry

There is no exit window because there is no investor. There is no peer cohort because you are not a part of a portfolio. You peer cohort is other bootstrapped startups about whom you may or may not know much. Worst yet, there could be confirmation bias there as well, as each one of you would be treading down the same path at the same pace.

You think you can execute in a vacuum

Some markets give you the luxury of being one among five players and yet be successful. Some don’t. Certain marketplaces like hyperlocal or transportation don’t allow you to pace growth — you own the place or you don’t. Bootstrapping to profitability does not mean much in such cases.

You are in a hurry

While your business execution happens without much hurry, your personal finance is hurriedly looking for options. The worst thing that can happen in a funding conversation with your existing investor is the realization that they may not participate in the next round. It may be the end of the story and that’s ok.

Your ideas and your cash flows don’t synchronize

While you can be proud about running a real business, if you are bootstrapped you’ve to give yourself a one year run-way. That’s money not spent on aggressive bets. Worst yet, that’s the money that does not earn you interest and yet goes way as tax, when you are not paying salary for yourself.

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Founder.Father.Freak - Oh that was fun f'ing around with lots of F's! I also tweet via @ContractIQ & @PipeCandyHQ

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Ashwin Ramasamy

Ashwin Ramasamy

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Founder.Father.Freak - Oh that was fun f'ing around with lots of F's! I also tweet via @ContractIQ & @PipeCandyHQ