Redefining Success: A Father's Evolution

I used to have this crystal-clear image of my future. Like many young entrepreneurs coming out of Harvard, I saw myself as the next Bill Gates – the multibillionaire founder who would change the world. That was the dream that drove me through my early ventures: HipBone, Shop It To Me, each one supposed to be the stepping stone to something massive. But life has a funny way of reshaping your definition of success.

The shift didn't happen overnight. It was more like a gradual awakening, triggered by two parallel tracks in my life around 2013-2014. Shop It To Me had hit a plateau just as I was settling into fatherhood. I started noticing things I hadn't before. We had acquaintances in that billionaire circle, and I watched as their personal lives had troubles. It got me thinking: what's the real cost of chasing those extra zeros?

I'll be honest – I wasn't exactly a natural with babies. Diapers and midnight feedings weren't my strong suit. I'm much better with kids when they're five and up, when they become little people you can actually talk to and reason with. But even before my kids reached that stage, something fundamental had shifted in my worldview. I realized that when you're old and looking back, having a strong family matters more than having a massive exit.

Running a startup while being a parent is like managing a perpetual teeter- totter. When you're building a company, there's always more work to be done. Every entrepreneur knows that feeling – the constant pull to keep pushing, keep growing. But then there's your kid, standing there at 3 PM when they get home, wanting to play basketball or solve math puzzles or just hang out. And you know, deep down, that these moments are fleeting.

I see it clearly through my brother's experience – how quickly kids grow up and stop wanting to spend time with their parents. It's made me more intentional about my time, though I'll admit I'm still not perfect at it. With Tyler, we bond over math puzzles and sports. With Lila, it's creative projects through Odyssey of the Mind, or singing together during car rides. These moments might not show up on any balance sheet, but they're the real measure of success.

Has being a father made me more risk-averse in business? Probably. When you're single, you can bet the farm on a crazy idea. With kids, you need to think about providing stability. But the bigger change has been in how I structure my work. I've deliberately chosen businesses that let me work from home, avoiding opportunities that would keep me constantly traveling or stuck in some distant city.

The most liberating realization was that you don't need to build a multibillion- dollar company to be successful. You can create something profitable and meaningful with a small, dedicated team. Small teams are more fun because everyone works together, making big contributions and seeing direct results. You're not dealing with politics and people jockeying for positions, or the overhead of huge meetings with massive amounts of people.

I won't pretend I've figured it all out. Some days I feel guilty for working when my kids want to play. Other days I feel guilty for playing when there's important work to be done. But I've come to accept that this tension is part of the journey. The goal isn't to eliminate it but to navigate it thoughtfully, knowing that both my business and my children need attention to grow.

Looking back at that younger version of myself, so focused on becoming the next tech titan, I can't help but smile. Success isn't just about the size of your company or the number of commas in your net worth. It's about building something meaningful while nurturing the relationships that truly matter. Sometimes the biggest achievements come from knowing what to chase – and what to let go.