So SaaStr itself had no revenue at all for the first few years, and still, almost everything we do is free.

But we have enough revenue now (tens of millions) to think of it as a bootstrapped startup  And the #1 thing I’ve learned is … how different bootstrapping really is.

A few learnings:

#1: It’s Harder to Set and Enforce Firm Goals When Bootstrapping

I mean, you can set them, but a certain amount of urgency is lost when you aren’t depending on outside investors, VCs, a board, etc. The consequences to missing a month just aren’t >that< high … unfortunately. :).

#2. Most folks that have come from a venture-backed environment don’t really want to work somewhere bootstrapped

The focus on cash flow and profits over just revenue alone just isn’t interesting to them. Not at all.  Folks that have worked in a venture-backed environment generally should stay in that environment.  They spend, think, and deploy capital and do hiring differently.

#3. The folks not pulling their weight are much more obvious when bootstrapping,

Because they are such an obvious cost center, versus the rest who are accretive.  When you’re venture-backed, yes, you monitor the burn rate carefully.  But you aren’t quite as sensitive when the bottom 10%-30% isn’t really making any money.  You see it, but you aren’t quite as sensitive to it.

4. Crappy Revenue Isn’t Worth It

A zero-margin product has little value when bootstrapping. It may have some, if it adds value, builds your brand, etc. But that’s it. But if you are venture-backed, you can happily sell a certain amount of zero-margin product and call it a win.  You can still count it as bookings, as hitting the MRR target, etc. even if the quality of that revenue is low.  But customers that you don’t make any money off of don’t help at all if you are bootstrapped, or barely help.

#5. Profit-Sharing and Other Bootstapped Benefits are Appreciated. Just Not >That< Much.

Almost everyone I’ve talked to that does profit sharing or similar initiatives gives up and just ends up doing traditional bonuses in the end, traditional sales comp plans, etc.

#6. The Right Amount of Headcount Is Far Less Clear When Bootstrapping. Probably Far Less is The Answer.

SaaStr has 7 employees. Should we have 70? Or 14? Or 60? You could grow faster. Or you might not. But you do know it eats into profits. Hmmm …

#7. Decisions Are Made Even Faster When Bootstrapping.

Finally, a small but interesting learning. Yes, startups move faster than scaleups that, in turn, make decisions faster than BigCos.

But bootstrapped startups just decide … today.

And a bunch of related learnings from my deep dive on bootstrapping and more with Ben Chestnut, CEO of Mailchimp, here:

And a few other great posts on bootstrapping here



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