From the Laptop of Jeremy Irish

Looking back after 10 years, I decided to jot down a few reasons why you should bootstrap your business instead of finding an investor. The biggest benefit is that you have an infinite runway - you will never be forced to "exit" by selling your company or going public. The biggest drawback is that you have to eat what you kill from day one.

• You are less than 6’ tall – According to the book Blink, the average man is 5’9” tall. While only 3.9% of adult men are 6’2”, 30% of Fortune 500 CEOs were 6’2 or taller. If you are vertically challenged it may be easier to bootstrap instead of raising money. I'm 5' 8" tall.
• You don’t have status – If you don’t have the right pedigree, such as education, notable former employer, run your own business before, or if you are a relative unknown in the industry you are targeting, you are a high risk for any investor. Prove yourself by bootstrapping yourself.
• You are not willing to ask for money – This can be surprisingly hard for some folks, like me, who want to raise capital for their business.
• Valuations are low – If you don’t expect to get a good value for your idea, build out your idea until valuations are higher. Most investors want traction. If you have traction, why would you need to raise money?
• You have at least one co-founder – Running a bootstrapped company is hard. Running it on your own is close to impossible.  A co-founder helps support you and keep you centered. Three, like at Groundspeak, is optimal since there is always the opportunity for a tie-breaker when there is conflict in the business. There will always be conflict in the business.
• You worked with your co-founders before – Optimally you have worked with your co-founders in the past and understand their work ethic. Going into business with your friends doesn’t give you an insight into how they work in a business environment. The co-founders of Groundspeak worked together before running the company.
• You have everything you need – You have the skills and partners to make the business work without additional support
• You have no young children – When kids enter the picture you need to mitigate risk and, depending on your parenting style, won’t have the time to dedicate your sweat equity into the business. When we started Groundspeak, we didn't have kids.
• Your co-founder is your spouse – I have heard more than once that investors don’t put money into business run by married couples. Too many investors have been burned by a divorce. I wouldn’t recommend starting a business with your spouse at all, but if you do you should bootstrap your business. It’s likely your only option.