The Unspoken Hard Bits of Bootstrapping

The compatibility of your idea and life circumstances with bootstrapping

I've always talked about this, but it has never had traction.

I call it "founder-market fit."

Basically your idea has to perfectly fit your goals, environment, situation, circumstances, character, personality, identity, experience, skills, knowledge, passions, interests, time/money/resources available, whether you have savings, whether you have a day job, whether you want a co-founder/to build a team, whether you want to prioritize stability of income or growth at all costs, whether it's compatible with your other life goals, etc. etc.

Too many founders pick an idea even before considering if the idea fits their own attributes like a glove, which is always a recipe for disaster. A solo founder indie hacker is not going to have a good time doing B2B/enterprise, for instance. And no matter how simple an idea (you mentioned Slack notification tool), it's always way more complex than you initially expect. I firmly believe that there's only a tiny subset of ideas out there that's suitable for a solo founder to tackle effectively. Outside of that subset, it's going to be biting off more than you can chew.

I started out trying to sell a dental payments platform to dental offices, which didn't work out, and now I'm working on a Twitter growth tool selling to prosumers/B2A, which is working out.

Because my lead flow is thankfully mostly SEO/baked-in virality, I have a little more breathing room to focus on the product itself, which is already a full-time job in itself.

On a side note, I'm impressed how comprehensive Outseta is as a product. How long did it take to build it to this point, and how many devs?

I like that you made that point about aligning your decision whether to bootstrap or not with your current and predicted life circumstances. I've actually just talked about this to a founder friend today. What we've noticed is that there's a huge hype around starting a company and an attitude of being rich (even if nothing was achieved yet!). Of course, if the scope of the project is too hug (as you also mentioned), investment is necessary. But from experience, I feel that a lot of people look for funding, simply because they don't want to cut back.

I feel that isn't talked about enough. Bootstrapping (and the freedom that comes along with it) often requires some cutting back, some restrictions in the way I spend my money. But that's short term, right? Once the money is coming in, I'm free to use it the way I want.

Not so in a funded venture. You got to pay that money back, since it's not yours. If projects are doable without investment, bootstrapping is an incredible opportunity. It is a little hard in the beginning, yes, but creates so much freedom in the long-run.

I started my bootstrapped personal branding business in September this year (https://melaniegoel.com/). The first product is a book: https://www.amazon.de/-/en/Melanie-Goel-ebook/dp/B08L6MDYG8/ref=sr_1_1?dchild=1&keywords=melanie+goel&qid=1602859687&sr=8-1 Next up a personal branding master class. It takes time to create, but with cutting my expenses back a little, it's a business that can easily be bootstrapped.