If you\’ve been an entrepreneur for more than a week, you know how hard it is to wait. The ideas come fast. The urgency feels real. And the pressure to execute immediately is almost overwhelming. But as someone who\’s spent over 30 years building businesses online—from the earliest days of the web to crypto and AI—I\’ve learned that the hardest part of success isn\’t taking the leap. It\’s knowing when to jump.
The Three Parts of Sustainable Success
I call it my Fun Formula, and it\’s built on three pillars that every entrepreneur needs to understand:
First: Curiosity. Stay alert to what\’s happening around you. The world is constantly signaling what\’s possible if you\’re paying attention. This is the easy part. Most founders and builders are naturally curious—it\’s why you got into this in the first place.
Second: Risk-Taking. You have to be willing to put yourself out there and fail. Nobody ever succeeded without trying things that didn\’t work. Every successful business I\’ve built came with a trail of experiments, pivots, and ideas that crashed and burned. That\’s not a weakness. That\’s the actual cost of the game.
Third: Serendipity. This is where most entrepreneurs fall apart. Serendipity is the part you can\’t force. It\’s the confluence of timing, opportunity, and readiness meeting in a moment. And unlike curiosity and risk-taking, serendipity isn\’t something you control.
Why Waiting Feels Impossible
Here\’s the truth that nobody tells you when you\’re starting out: the hardest skill to develop as an entrepreneur isn\’t innovation or sales or fundraising. It\’s patience.
Entrepreneurs by nature are action-oriented. We see a problem, we want to solve it now. We spot an opportunity, we want to capitalize on it immediately. This bias toward action is why we get things done. It\’s also why most of us are terrible at waiting for the right moment.
I\’ve experienced this multiple times in my career. After the collapse of the NFT market in 2021, I made a deliberate choice to step back. My focus shifted from the hustle mentality to something different—what I call the \”Caribbean semi-retirement.\” I moved to Puerto Rico. I continued hosting The Bad Crypto Podcast, but I wasn\’t chasing the next big thing. I was living. Traveling with my wife Erin. Spending time with people I care about. Enjoying the lifestyle that years of grinding had finally made possible.
But here\’s what happens when you step back: the creative part of your brain doesn\’t shut down. You still want to build. You still want to create value. The lack of a clear \”next move\” starts to feel like a void. Friends ask you what you\’re working on. You have internal conversations about whether you\’re being smart or just lazy. The pressure to have a plan kicks in.
The Moment Everything Changed
The hardest part of the Fun Formula isn\’t admitting that serendipity matters. It\’s actually trusting it enough to stop pushing.
I had been in this in-between space for four years. Years of dabbling. Years of \”what if.\” Years of conversations about what I should do next. There were plenty of things I *could* do. Plenty of opportunities I could chase. But none of them were lighting me up. And I\’ve learned that when you\’re choosing between multiple things that don\’t excite you, it\’s usually a sign you should keep waiting.
Then Erin and I took a cruise to the eastern coast of Canada, Iceland, and Greenland. Beautiful ship called the Volendam. Whale watching. Stunning landscapes. The kind of trip that makes you remember why you built everything in the first place.
And on that ship, a casual conversation with a stranger happened.
That conversation opened a door to an opportunity I hadn\’t even considered before. It wasn\’t the result of hustling or networking or strategy. It was the result of being in the right place, with an open mind, at exactly the right moment.
In that single moment, I went from wondering what I should do next to seeing a clear vision unfolding.
That\’s serendipity. And it doesn\’t work unless you\’ve already mastered curiosity and risk-taking. You have to have proven you\’re willing to take chances. You have to be awake and paying attention. But most importantly, you have to stop pushing long enough for the right opportunity to find you.
The Part Nobody Wants to Hear
Here\’s what I wish someone had told me when I was younger and in a hurry: you can\’t optimize your way to serendipity. You can\’t speed-force the timing of something. You can\’t force the market to care about your idea before the market is ready.
What you *can* do is get really good at two things: staying curious and taking calculated risks. Then you have to develop something that feels almost antithetical to entrepreneurship—the ability to wait patiently for the confluence of circumstances that makes things click.
Some of the best decisions I\’ve made came after periods of strategic patience. Some of the worst came from forcing something before its time.
If you\’re in a place right now where you\’re asking \”what\’s next,\” my advice is simple: keep your eyes open, be willing to take risks, and don\’t underestimate the power of doing nothing while remaining completely ready.
Sometimes the most productive thing you can do is wait for the right moment. And I can promise you—when the moment arrives, you\’ll know it.
Want to explore more about building in the modern internet landscape? Join the conversation on The Bad Crypto Podcast where we dig into stories like this one, or sign up for my newsletter to stay in the loop on what I\’m building next.