I’ve managed to bootstrap from $0 to $1M ARR twice in the past decade.
Now I’m working on doing it a third time with rb2b.com.
Here’s what I’ve learned about bootstrapping a successful startup.
Table of Contents
Advice for Bootstrappers
Here are 6 of my best advice for bootstrappers:
Be Extremely Frugal
I made so many unnecessary spending mistakes in my early days.
I bought a phone system I didn’t need. I rented an office that was completely unnecessary. I lived in an expensive Manhattan apartment. I even bought two expensive cameras for content that I only used once.
Your money is your lifeline – be incredibly careful with it. Things will get extremely tight before you succeed.
Focus on Product-Market Fit
When you achieve true product-market fit, everything flows naturally and feels easy.
Without it, everything’s a constant struggle. I’ve experienced both sides.
Until your product grows through word-of-mouth, focus entirely on making it better.
Master Marketing Skills
Once your product is solid, the best way to grow a SaaS today is through high-velocity inbound marketing.
Learn everything: offers, funnels, conversion, paid ads, organic social, differentiation, channels, content, and pricing.
Having deep marketing knowledge yourself is much better than relying on others for core business decisions.
Be Strategic with Hiring and Firing
Don’t hire your first employee until you’re completely overwhelmed. Wait to hire the next one until everyone’s struggling again. It’s hard to fire people at first, but experienced founders know to cut ties the moment something isn’t working. As someone told me, “I never regretted letting someone go, I’ve just regretted not doing it sooner.”
Start Small
While big ambitions are great, larger ideas are usually more complex and harder to execute.
I started small, and each of my ventures has grown significantly larger than the last.
Choose Great People
Our odds of creating huge companies are small.
We might create an average company, or more likely, fail entirely.
Any of these outcomes are manageable if you’re working with great people.
Even massive success feels hollow if you’re surrounded by the wrong team.
Conclusion
These lessons come directly from my experience building multiple successful businesses.
I’m using them right now as I build my third venture, and they’re still proving true.