Freedom, Purpose, Relationships

At Microconf this year, Rob Walling gave an interesting retrospective of trends he’s seen in the bootstrapped SaaS space.

While techniques have come and gone over the years, the one constant for Rob was the combination of key motivators driving bootstrapped founders:

Rob’s succinct summary resonated immediately with me (and likely most other attendees), and I’ve been thinking about it ever since.

It’s funny how three simple points can explain why I quit my job, started my company and have been on the less-travelled bootstrapper path ever since.

I think that most founders would name this trio of reasons when they first set out to start a business. We all want to chart our own course, doing meaningful work with great people.

However, decisions and circumstances along the way may demand that we sacrifice some of these goals. To my mind, this is where bootstrappers critically diverge from founders that take on external (generally venture) funding.

Jumping on the venture-funded rocketship usually results in founders forgoing one or more of these ideals; with money onboard, the business takes on a different set of priorities - typically growth at all costs. When your board members need to more than 10x their investment, it’s much harder to put social justice above user counts, customer care above press relations, or the wellbeing of your family (let alone yourself) ahead of raising the next funding round.

In contrast, bootstrappers view all three reasons as equal pieces of the same whole - this trio of motivators form an indivisible trinity. A deep unwillingness to give up any one part of this trifecta is a hallmark of indie and self-funded founders.

I think this is because self-funded founders strive to live out this trinity daily - by shaping our products and businesses as we see fit, executing our purposes through work, and enjoying our relationships with team members and customers.

It’s definitely a tougher path, particularly in the early years as we scramble for revenue, but even on the hardest days, we’re realising our “why”.

And for bootstrappers, that means more than chasing a billion-dollar exit.


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How much success is enough?

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