Why Bootstrapping Is The Entrepreneur’s Playground For Hands-On Business Learning

People sometimes conflate bootstrapping with starting a small business, but the reality is that most bootstrappers have huge ambitions—they just prefer to go it alone. Bootstrapping means maintaining control. Bootstrapping means freedom. Bootstrapping means getting to play.

Growing your business from the ground up is like building a playground for your company, where you can test and tool around with all aspects of the business until you become an expert, similar to how children play with toys until they master them. It’s not about winning or losing, but instead, understanding how it works. By bootstrapping, you give yourself a landscape for experimenting with how to build great products and how to gain—and keep—customers.

Here, a closer look at some lessons from the playground on giving your company the time and space to tinker.

Mastery Of Key Entrepreneurial Skills

When LEGO hit a major slump, they hired a team of researchers to understand how kids play with LEGOs and to identify general patterns about child play. As Quartz explains, the researchers found that early aughts kids were “bubble-wrapped.” Their parents managed and curated every aspect of their leisure activities and physical spaces (think: kids’ bedrooms that looked like a page from Architectural Digest). Unable to enjoy the same freedom as past generations of kids (for example, playing on sidewalks or roaming freely in the countryside), these early 2000s kids were carving out freedom in virtual or imaginary spaces.

Another insightful observation involved an old shoe. An 11-year-old boy shared that it was his most prized possession because it was filled with ridges and nooks that evidenced his dedication to mastering a skateboarding trick. The researchers concluded that assumptions about children seeking instant gratification were untrue. Rather, the most meaningful play involved degrees of difficulty and skill acquisition. In short, kids don’t always opt for the iPad.

The takeaways? First, humans need freedom for their imaginations—it’s in our DNA. If parents infringe on their kids’ freedom, kids will find ways to recreate it. Second, it is immeasurably more satisfying and meaningful to master something when you put the work in; when you earn your stripes to become an expert.

Being a bootstrapper is like paying your dues rather than opting for some of the more instant gratification that comes with investor funding. You have time to learn everything about running and growing a business—leadership, sales, marketing, HR, product management, and more. You can focus on one area, reading about it and watching all of the YouTube videos, then apply those lessons to your business and experiment. Once you’ve done everything you can to master that area, you can switch to another one.

VC fund cycles are usually about 10 years. Investors expect an exit within that period. Without investors to answer to and aggressive KPIs to hit, bootstrapping offers much-needed practice time. Like falling a hundred times before you nail your first ollie, entrepreneurs master new areas by attempting and fine-tuning.

Out-of-the-box Thinking And Better Products

Speaking of LEGOs, when I watch my sons play with them, I’m impressed by their determination to build something bigger, better, and cooler. They’re not racing the clock. Instead, they lose track of time, becoming absorbed in their castle, helicopter, or skyscraper. This kind of imaginative play makes kids more creative, too. One study showed that kids who played with salt-dough for 25 minutes, rather than completing a text-copying task, were subsequently more creative in a collage activity.

Bootstrapping gives you the leeway to tinker with your product or service. You can explore for exploration’s sake, and in doing so, expand your capacity to innovate. You can come up with the best version of your product or service.

As I tell my founder-mentee, growth requires two things: to improve your product and to bring people to use it. I call it the 50-50 rule: 50% product, 50% sales and marketing. If you dedicate too much time to one, you’ll lose momentum on the other. For a while, my mentee would come to meetings excited about new sign-ups. But when I asked about existing customers, they all had different reasons for dropping off. I told my mentee that he needed to make his product stickier. This is where entrepreneurial “play” can prove vital. Through playing, you can figure out how to improve your product, or even make a more substantial pivot if need be, to make your product stick.

Bootstrapping means less of a “stress pressure-cooker” environment. Instead of getting caught up in destructive thought loops and dwelling on what went wrong, you can move on and try something new. The game has lower stakes.

As a bootstrapper in the game for nearly two decades, I can attest that building my business from the ground up has been a source of pride and satisfaction. We failed plenty along the way, but in hindsight, I can see how those small slips, like scuffs on skateboard sneakers, made us more resilient and innovative in the long run—enabling us to grow despite economic downturns, global pandemics, and tech giant competitors. It wouldn’t have been possible had we not had the space to experiment and play.