Accelerating Boostrappers

I believe that the bootstrapper community would greatly benefit if individual founders joined forces, Voltron-style.

Let me explain.

If you hang out in bootstrapper circles–places like MicroConf, BaconBiz Conf, or–you’ll find plenty of smart, talented, and highly-motivated entrepreneurs trying to build SaaS businesses on their own, in their spare time, without much cash.

Inspiration comes from likes of Patrick McKenzie (Appointment Reminder), Ruben Gamez (Bidsketch), Rob Walling (Drip, HitTail), and Garrett Dimon (Sifter), each of whom has reached escape velocity with their startup. But for every Ruben Gamez you’ll meet 100 skilled bootstrappers who are scratching and clawing just to ship something, anything.

Unfortunately, the likely outcome for a bootstrapper is burn-out, dwindling interest, or perpetual “side-projects.” In other words, failure. (Other times we fail for the same reason funded startups fail: nobody wants what we made.)

What is success to a bootstrapper?

It is not building the next Facebook or Twitter. We don’t raise venture capital because we don’t want lots of employees, a board, and pressure to exit. We’re not aiming for the fences. We’re looking for what the Valley often calls singles and doubles.

Bootstrappers usually want the following two things:

1.) To earn a fantastic living 2.) To build and sell software products with people we love and respect

The accelerator approach

I’m not suggesting, as some people have, that solo-founders team up from the start as co-founders. Instead, I propose that we turn mastermind groups into mini-accelerators using the Idealab model (as opposed to the YC or TechStars model).

Companies within Idealab are malleable. The founder, Bill Gross creates, modifies, and kills companies as he gains information about which ones are likely to succeed. More importantly, it’s not a winner-take-all system. Rather, the whole of Idealab is enriched when they produce a successful company.

Translating this to bootstrappers: in a mastermind, when one of the members starts getting serious traction with their product, 1 or 2 of the other members can elect to sideline their own products and join the promising one in hopes of making it a winner (where winner == a small, highly profitable software business).

Check my hypothetical math, but $60,000 in monthly recurring revenue (MRR) with 3 highly-talented entrepreneurs seems much easier to achieve than 3 highly-talented entrepreneurs trying to achieve $20,000 MRR on their own.

But how in the world is this a good idea for the original founder? Because growth and success for a bootstrapper can be excruciating at times–specifically the times at which you would typically raise and deploy venture capital.

This slide from Garrett Dimon’s amazing talk Bootstrapping a Software Product sums it up nicely:


If the founder can short-circuit the “most challenging time of my life” leg of the journey and share his/her success with 1-2 like-minded bootstrappers, that’d be awesome!

The cap table shouldn’t really matter because of the no-exit premise, but you could do a 50/25/25 split. Again, the goal isn’t to build the next Oracle (God help us), but building the next 37Signals or Balsamiq or Panic would, in my mind, be a net-benefit for the world and help more micropreneurs reach the ultimate goal of earning a fantastic living building software on their own terms.

This is merely a thought experiment, but I would absolutely love to hear your thoughts in the comments below!

Sidebar 1: The podcast Our Own Little Accelerator sparked the idea for this post. It’s essentially a recorded, published mastermind session. It’s awesome! A few episodes in, it had me thinking, “Wow, if a few of these guys just joined forces and worked on one good idea, they’d be wildly successful.”

Sidebar 2: For more on Bill Gross and Idealab, check out this fantastic interview on This Week in Venture Capital.