One of my friends is an entrepreneur with a wide ranging portfolio that spans real estate, franchises, ecommerce stores, and software. Some of these businesses have seen dramatic growth. Whenever we chat, he’ll describe a new business—often two or three—that he’s directly working on. I pay attention because I always learn something new.
Sometimes, I even learn something in between our conversations.
I recently visited one of the ecommerce businesses he’d shown me a few years ago, investor deck and all. I visited the website and noticed that it was still a prototype. There were three items, and the writing made it clear that it was still in beta. I imagined that he was paying to keep the site live, but wasn’t doing much else with it. Perhaps one way to think about this: he was keeping it in maintenance mode, waiting for the right business partners to come along and activate it.
It made me remember another one of his ventures, which bore resemblance to a startup studio like Expa. He’d spent a lot of time and energy on it. He’d even developed a couple of businesses with other entrepreneurs under the startup studio brand. We had spent an afternoon together working through positioning and writing for the website. In spite of all of this, it didn’t gain the momentum he wanted to see. I know he really wanted it to work—it was an effort that took up his energy for a year or two—and ultimately it didn’t gain momentum. He needed to find another path to achieve his goal, or move on to a new goal. And he did.
The lesson is, with his approach, that perseverance is not always a virtue. There is plenty of lore describing the outlandish tactics or degrees that entrepreneurs breathe life into their businesses. Airbnb’s founders sell $30,000 worth of cereal. FedEx’s founder bet his business’s cash in a bid to keep his business afloat. Steve Jobs spent $50 million to keep Pixar alive. But for every one of these, I do wonder how many stories of negative outcomes remain private, only whispered about by families, financiers, and other entrepreneurs.
Great leaders stack the deck to win. For example, an executive coach only chooses clients who are almost sure to succeed, and disqualifies everyone else. A book agent, applying this mindset, might only choose to spend time with authors who have rapidly growing audiences and have delivered good books already. A CEO will constantly recruit, focused on keeping the best people around them.
My friend, like many other entrepreneurs I know, stacks the deck by finding and focusing on ideas that are almost certain to succeed. Sometimes, he disqualifies ideas quickly, like the ecommerce store. Other times, he gives ideas more time and space, like the startup studio, and ultimately still disqualifies them. By saying no to these ideas, he limits his risk, and he opens up space to try new ideas. None of them really know what will work.
Different entrepreneurs will have different milestones that they need to meet by a specific deadline, before they give up on the idea (known as kill criteria). Some are more process-driven, focused on delivering a product by a certain timeline. Others need to see business results such as sales or financing quickly. Still, others are focusing on developing a thesis or hypothesis to learn something other people don’t know. What they have in common is they all set a limit of energy that they are willing to give to it, and they adhere to that limit.
Sometimes, an entrepreneur might give up too quickly on an idea showing slow momentum. Other times, they might give up too slowly on one that was not a good fit for them. This sense of taste requires a constant fine tuning. It’s fun armchair conversation, and nobody will really know or take responsibility except the entrepreneur.
Like all prioritizing, you’ll know you’re doing it right when it hurts a little bit. In my experience, perhaps the only difference is giving up on a bad idea is the pain comes with a sense of relief. The part of you that was telling you—sometimes, screaming at you—that you were overextended in an idea, will be glad that you finally listened.