BOOTSTRAPPING ★ 190 upvotes 2019

Finding My Next Bootstrapped Business Idea

Retrospective Overview & Key Insights

Distilled analysis of the business dynamics, operational challenges, and strategic takeaways:

Published in 2019, this chronicle by @derrickreimer details the mechanics of building a profitable, self-funded business without venture backing.

Core Principles for Independent Builders:
1
Charging customers from day one acts as the ultimate filter for building software that solves genuine, high-urgency problems.
2
Keeping fixed overhead low and leveraging lean infrastructure allows founders to stay alive until market tailwinds kick in.
3
Small, repetitive improvements in customer retention and conversion rates yield massive returns over multi-year horizons.
Community Debate Themes:

The community focused on B2B customer acquisition channels, cold email vs SEO distribution, and balancing full-time employment with side-project development.

Community Discussions & Critical Reviews

High-signal perspectives, counter-arguments, and peer founder insights debated on Hacker News (48 total discussions):

DO @docker_up Peer Contributor

I find articles like this deeply disingenuous. The OP wants to basically find some problem that he doesn't know anything about, and apply whatever knowledge he has gained in hopes of building a "company" which appears to me is just a facade of a company until he can flip it to someone else who actually cares more.

The idea that someone with presumably no knowledge or even any passion can dip their toe into a problem space and try to create a "company" isn't very appealing to me at all. Everything about it feels so superficial and contrived with no passion.

Even the list he came up with is so low-hanging-fruit, it reads to me "I want something that is easy to build, easy to sell and makes me lots of money before I flip it to someone else, and then I can start the process again."

The lack of commitment and conviction screams to me that I shouldn't become a customer because he will abandon the project, and end it with another "Thanks for following me on my journey, I'm abandoning all my customers but join me on my next adventure soon!"

LI @listenandlearn Peer Contributor

Hey Derrick,

Thanks for the great posts and for responding to comments!

Would love some feedback on choosing to raise money or not. I read this post (and many others) about having those filters ready ahead of time. The filter on raising money unfortunately I don’t have, I keep going back and fourth on that.

I have been working on an app, cross platform iOS and Android, that lets people listen to articles from the web. It uses great sounding AI ML to convert the articles to audio you can listen to in seconds.

I have been working on it for a few months have some good traction and a few paid users, working on it part time as a side project. I can’t help but feel that raising money would allow me to go full time and really concentrate while still affording my bills. The issue is VC money comes with strings.

(Shameless plug for anyone interested, the product is here https://articulu.com )

KS @ksj2114 Peer Contributor

"The market must already exist". I think trying to find a brand new market is one of the biggest mistakes many founders make when trying to come up with a startup idea. An existing market indicates that demand already exists!

And when "no market need" is the most common reason startups fail [1], this seems to be often overlooked.

[1] https://www.cbinsights.com/research/startup-failure-reasons-top/

MR @mrskitch Peer Contributor

Hey Derrick! I don't have much to say, except that I really enjoyed your site's design. Good luck!

EDIT: Now that I've read through your article: I'm the founder behind browserless.io. Your outline is great, and is the same rough rubric I've used before. If you ever want to chat about anything, let me know! You're totally right: this thing is hard, and having more successes/failures doesn't make it any easier sadly. Lot's of dice rolling and trying.

RE @realty_geek Peer Contributor

Hi Derrick, looking at the criteria you listed I would say you probably could find some interesting ideas in the real estate sector. I created an open source real estate website builder and though that hasn't made me any money, it got me enough contacts and insights into the sector to make me realise how much potential there is there.

I am happy to have a chat if you want to know more. My plan is to launch a product in that space in the next 6 months

HISTORICAL ERA Cloud & Mobile Era (2014–2019)
COMMUNITY SCORE ★ 190 points
TOTAL DISCUSSIONS 48 comments
TOPICS & TECH STACK: