Negotiating bootstrapped

Dilly dallying
2 min readFeb 29, 2024
image from craiyon ai

Bootstrapped is when a business develops itself with minimal external support. Without any/much loans or funding from someone else. Logically this is how a business should build. But there are types of businesses wherein you expect great returns later but have high upfront/capex costs. In these cases a downpayment by someone is a way to make something happen faster. Plus all parties benefit sooner or later.

Bootstrapped is slow, difficult, consuming. I get it. You create a business from scratch, from nothing. In your early years you have to remind people about your bootstrappiness so they can cut you some slack, slash down on their own profit margins to support you. It is temporary, it is a reminder, a leveller of sorts, i get it. But soon you are >5 years old, still running rudimentary operations, still not optimised for costs, still running a survival first ship and now ‘bootstrapped’ is a negotiator. You use it while hiring, while paying for services offered by other businesses and most of all while deciding rates i.e. every time you have to part with money, not when you have to accept it.

‘I am bootstrapped, so I can only pay so much.’ Those taking a hit on their profits for you are now exhausted because your growth is now supported on their backs but there seems to be no end to the ‘temporary’ leeway for the ‘bootstrap’. You bleed into inefficient systems, burn into unexpected, unforeseen circumstances. Unforeseen after years and years of seeing.

‘I am bootstrapped, so I can only pay so much.’ ‘So much’ is below minimum wage. Are you charging your customers lesser because you are bootstrapped? Are you expecting lesser quality & quantity of work from your hires? Are you giving back the leeway that you keep benefiting from?

You are bootstrapped (since forever and will be for the foreseeable future), how should that concern me? Is that a coupon to get out of paying? Can I use that coupon too to pay for a swanky car and business class flights?

Can I, a bootstrapped person with 16 yrs of experience, 16 yrs of chipping away at my craft supported just by myself, deliver a fraction of my capability because you can only pay me ‘so much’. But I am bootstrapped too and I can only work ‘so much’!

Do the principles of your bootstrappiness still work when the tables turn?

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Dilly dallying

A bit of this and that, real life and fiction until can’t tell one from the other