Important Lessons About Bootstrapping A Business From A CEO
You’ve probably heard of pulling yourself up by your bootstraps.
It’s a hardy phrase that conjures the image of an old-school go-getter doing everything they can to keep their feet on the ground and a handle the world.
There’s a lot to gain from being self-sufficient and finding your own path — especially in the business world.
For me, bootstrapping was critical during my early years. Before I was CEO of Shipchain, I was a doctoral candidate in the physics department at Florida State — until my funding was cut. With my T.A. salary gone, I needed a new way to pay the bills. I’d made money off web design in high school, so I pulled up my bootstraps and starting selling my skills door-to-door.
I saw this moment as a crossroads: I could get a “real” job, or I could use my own know-how to get myself to the next step.
This sent me down the path to discovery which ultimately resulted in where I am today. And it wasn’t easy. Bootstrapping a company definitely isn’t for the faint of heart.
In case you find yourself standing where I did so many years ago, here are a few lessons I learned along the way:
1. Don’t Be Afraid of Risk
A lot of people make the mistake of continuously researching how to start a business without ever taking the plunge and actually doing it.
It’s usually because they’re afraid of the risks. You have to know when it’s time to take the plunge and just do it. Sometimes the plunge happens to you and you don’t have a choice. In my case, when my teaching assistant salary was taken away due to the loss of funding, I had to either pay for school myself or essentially say goodbye. I chose to say goodbye.
I wasn’t sure what I was going to do specifically, but I was sure I’d figure it out.
And trust me, the quickest way to make something happen is when you look at a bank account that’s almost zero. You have to do something. So, I went door-to-door selling website development.
I went to restaurants and small businesses to show them what I was capable of creating. It was 2010 at this point, so if you didn’t have a website you were in a lot of trouble. I helped them understand the capabilities of a website and how much of their business was going to come from the internet in the near future.
After doing this for a short period, I began to recognize some of the bigger issues in online ordering and shipping. To answer that need, I started my first company, Direct Outbound, as a source of support for rapidly growing e-commerce sites.
The risk had originally been that I had no idea what course my life would take after leaving the physics program. But the payoff was so much bigger than I had imagined at the time.
2. Be Familiar With Failure
When you’re putting something together all on your own, you have to be comfortable with the prospect of failing.
You have to think to yourself, “What’s the worst that could happen if I don’t succeed? I go get a job? Okay, that’s fine. That’s not scary at all.” There’s a definite downside, but at the same time, if you fail, you fail. Failure is not always a terrible, life-ending thing.
I’ve failed more times than I’ve succeeded, but I don’t consider it a badge of honor. It’s just a fact of life.
Think of it this way: do you remember the overachieving type you went to high school with? They always got straight A’s in everything, and they were in every club. But after graduation, most of them went on to take the safe route and never start anything new for themselves. They needed to stick with the familiar, and that didn’t involve failure.
So if you have no familiarity with even the possibility of failing, it takes a lot to accept it.
3. Go All In
One of the biggest benefits of the bootstrap approach is that you learn you can do anything.
This is because the founders have to jump in and basically play every single role. You’ll have experience in every angle of the business because you’ll be involved in everything.
And a good founder should know what’s going on and be able to dive in if your people need help.
For example, when we first started Shipchain, I was in the warehouse packing boxes with my crew. People don’t really picture the CEO in the warehouse packing stuff up, but sometimes you still want to help.
4. Be Responsible and Resourceful
Finally, because you’re doing things entirely on your own, bootstrapping a company means being as responsible and resourceful as possible.
It teaches you to be responsible with the money you have and not emulate all those crazy startup stories that make the news.
You hear about how they raise a bunch of money, and then immediately start blowing it on a lot of crazy stuff.
Bootstrapping, however, really gives you the experience of knowing exactly what you’re doing, and how to save money, because you don’t know when your next source of income will arrive.
That being said, a slim flow of income means that you also have to be able to work with what you have. You have to be resourceful and find ways to repurpose and retool what’s on hand. Maybe that means the CEO takes phone calls and works in the warehouse, like I did. Maybe it means sharing office space until you’re ready to move forward.
It can be anything, but at the end of the day, being resourceful is the biggest part of being a bootstrap company.
You’re looking at your own skills, and the skills of those you’ve brought on board, and finding the best combination to create something from nothing.
And once you’ve done that, there’s nothing that can stop you — just put one boot in front of the other.
