The Unspoken Hard Bits of Bootstrapping a SaaS Product to Life

For me personally, this meant that for years, literally, there was always this nagging feeling that I could be doing more. I could be doing more or doing better for Outseta, and I could be doing more in terms of the other projects I was working on as well. For me, that feeling has been tough. It feels really good to be able to say that you unequivocally, without question, are giving something your all.

This has been the dealbreaker for me whenever I've tried to bootstrap side-projects or incubate potential startup ideas while holding a full-time job. It always leads to frustration after a month or two, since I'm unable to perform to the best of my abilities on either the day job or the side project.

For me personally, the better route (for my sanity, at least) has been to double down on my career, putting everything into the day job. The big downside of course is that I've had to put any startup plans on hold indefinitely. But the upside is that I only have to focus on one thing (day-job performance), and since I'm lucky enough to be in an organization where performance is rewarded, that has led to career progression over time.

Rather than inflate my lifestyle, I've continued to live modestly and save/invest my compensation bumps. This extends my personal runway and increases my confidence that when the time is right, I'll be able to responsibly quit and focus 100% on my own thing without risking my family's financial wellbeing.

I know this isn't the right path for everyone, but for me at least it's what has kept me sane!

While I understand that no one wants to wait a few hours for a response to their question, if you’re bootstrapping with a small team you’re likely not going to be available 24 hours per day.

In my experience, customers who sign up, demand immediate customer support, then cancel a few hours later because they didn't get it, are doing you a favor - imagine what a drag on your customer support efforts they'd be if they stayed!

My rule of thumb is customer support thru email should aim for 24h turnaround, except if they're paying for "premium support". Great if you answer in 5min because you were just at the helm, but you shouldn't set unreasonable expectations.

Live support is murkier - if you do have set it up and are offline, falling back to email that gets answered tomorrow does seem slow, just by the fact you've just anchored me to "live". In my opinion, don't do it (or hide the widget!) unless you can really provide near-realtime response (even if via outsourced 1st level support agents).

The hard truth that no one wants to give lip service is that early on, bootstrapping your company may be the best decision for you but it’s not the best decision for your customers.

I'm surprised this was highlighted in the article. It is one of the least compelling statements. VCs drive for high risk, fast growth plans, while what customers need is stability. If they have a service that works for them, at a solid price point, where the service meets their needs while delivering a profit for the business, then everyone wins. The last thing that a customer needs is for a working product to pivot into a high-growth plan that puts the business in the red in pursuit of even more profit.