One of the most effective TV commercial campaigns of all time was the “easy button.” It was created by US office supply retailer Staples, Inc., and it featured people pressing a fictitious “easy button” when they needed help with complex, office-related tasks. The campaign was so effective that Staples began manufacturing toy easy buttons and ultimately sold millions of them. How many other TV commercials have done that?
My startup had one of those toy easy buttons. I don’t remember exactly how we acquired it, but it had a place of honor in the center of our conference-room table. Anytime we were in a meeting and struggling to come up with a solution, someone would inevitably lean over, push it, and make a joke about how our easy button was defective.
Of course, it wasn’t actually defective, and not just because it was a toy that wasn’t supposed to do anything in the first place. Instead, I’d argue the easy button wasn’t defective because startups are supposed to be hard, and that’s a good thing.
To be clear, I understand entrepreneurs don’t want their startups to be hard because… well… who would rather something be hard if the same thing could be achieved with significantly less work? However, whether founders like it or not, the hardest parts about building startups are also the things that prepare startups for success. In fact, the entrepreneurs who don’t experience the biggest challenges of building companies are the entrepreneurs who are most likely to fail. It’s why every founder has to learn to avoid the temptation to press their proverbial easy buttons and embrace the hardest parts about building startups.
To help explain this, and to help you hopefully appreciate whatever difficult challenges you’re currently facing with your startup, here are three difficult startup scenarios I faced early in my startup career and why struggling with them was ultimately better than being able to press a magical easy button.
At least half the new entrepreneurs I work with are solo-preneurs operating alone. When I ask them why, the answer is usually something along the lines of, “I just haven’t been able to find a good co-founder. Finding good co-founders is hard.”
They’re right. Finding good co-founders for a startup is hard. More importantly, it should be hard. I know because I didn’t struggle finding my co-founder. In fact, finding my first co-founder was one place where I did push my personal “easy button,” and it ultimately made building a successful startup much harder.
The reason I didn’t struggle finding my co-founder is because my first co-founder was my childhood best friend. Obviously, I didn’t have trouble finding him. Instead, when we both realized we were interested in building startups, we immediately gravitated toward working with each other, and we spent over a decade as co-founders of multiple startups.
That kind of relationship surely seems lucky. After all, who wouldn’t want to build a company with a close, personal friend? But, the reality was very different.
While I enjoyed working with my best friend, we spent our first five years being ineffective co-founders precisely because we were friends. As friends, we were basically the same person. We saw the world in the same way, we problem-solved in the same way, and we enjoyed working on the same things. This made us inefficient. For example, we’d work on product ideas together, we’d work on pitch decks together, we’d work on marketing assets together, and so on. As a result, everything took twice as long, plus, nobody was working on the dozens of other things that also needed to be done.
If all of that weren’t problematic enough, there was an even bigger issue. Specifically, because we were best friends, we had the same weaknesses and blindspots. Rather than compensating for each other’s shortcomings, we created an unintentional echo chamber within our company where we tended to agree with each other’s poor decisions rather than question them.
The better — though harder — approach to having a co-founder is to do the hard work of finding someone who doesn’t see the world like you. Yes, co-founders should want to accomplish the same things, but they should envision accomplishing those things in different ways. This creates a healthy friction within organizations that make startups more successful, more nimble, and more sustainable.
I realize that finding and working with people who properly compliment you rather than duplicate you is hard. It means you’ll have to look for people in places you wouldn’t normally be, and it means you’ll have to communicate with people in ways you wouldn’t normally communicate. Neither of those things are easy. But the results will be better. When co-founders compliment each other, they’re much more likely to form the backbone of a successful enterprise.
Fundraising wasn’t easy for me. I spent years trying to get my first capital infusion, and I was always jealous of the founders I knew who seemed to be able to push whatever magical “easy buttons” they had (friends, family, trust funds, slick pitching skills, etc.) to snag checks for companies that seemed so much worse than mine. However, in the end, my company outlasted all the companies I was jealous of, and one of the big reasons was because struggling to raise money helped me build a more sustainable startup.
Because I was a founder who spent years bootstrapping, I understood and appreciated the value of money more than all my founder peers who raised big rounds of financing earlier in their journeys, and I was more responsible with the money I did raise.
This same issue constantly repeats itself in the startup world. Founders who raise money too soon don’t know how to be responsible with their money. They hire lots of people, they rent expensive office spaces, and they spend lots of money on marketing campaigns without necessarily understanding how to convert people into customers. As a result, they often spend all their money before they’ve built a sustainable venture and they fail.
In other words, while raising millions of dollars early in your startup career might seem amazing, you actually don’t want to. Strange as it might seem, the best way to avoid raising money too early is by struggling to fundraise. When fundraising is hard, founders become more responsible in their spending, and that leads to better companies.
For most entrepreneurs, the first customers they target are often friends and family or people with whom the founders have pre-established, professional relationships. This is the “easy button” version of sales because people we already know are the easiest people to sell to. But selling to easy customers is short-sighted.
At some point, all founders reach the ends of their personal networks. However, if a founder’s personal network happens to be large, he can trick himself into thinking he’s reached product-market-fit when, in reality, he only leveraged his network to secure some early buyers for a mediocre product.
Since very few people have networks large enough to sustain entire companies at scale, building a company on the back of a pre-existing network rather than genuine product-market-fit is a terrible idea. You can avoid this outcome by not using your personal network to acquire your first customers. Instead, in the earliest days of your startup, only sell your product to strangers.
Yes, selling your product to strangers will be harder than selling it to people you already know, but, when you’re successful, you’ll have a sustainable, scalable company, and that’s much better than telling all the friends/customers you convinced to give you money that you’re shutting down.