Building a Startup That Loves You Back

A year ago, on a random Tuesday afternoon, I was driving home from an appointment and called an old friend — someone I’ve known for years, a high-level exec with big responsibilities and serious sales goals.

I asked him what he was up to. He said, “I’m floating in my pool.” I laughed. I thought he was joking. It was 2pm... on a Tuesday! People like him (people like us) don’t do that.

So I asked him why. He paused, like he’d never really been asked that question before, and simply said, “It makes me happy.” That was it. No explanation, no excuse. Just a basic truth. And in that moment, it hit me: the fact that I didn’t know that answer was my problem, not his.

Reclaiming Our Time

Founders are great at building companies, but terrible at building boundaries. Somewhere along the way, we confuse commitment with exhaustion and assume that burning out is just part of the process. We’ve built up a tolerance for discomfort, and then call that “productivity.”

I had to retrain myself to see rest as a strategic tool, not a reward for getting things done. I started focusing my days around a single, meaningful outcome instead of chasing an endless list of tasks. If I nailed that one thing, I gave myself permission to call it a win and step away — no guilt, no qualifiers.

More importantly, I began protecting my best hours. I stopped letting distractions or fire drills hijack the time when I do my best thinking. If I’m going to put my energy anywhere, it should be into work that actually moves the business forward — and ideally, work that makes me feel good while doing it.

Aligning the Business With Our Values

At some point, I stopped asking whether the business was “working” and started asking if it was still working for me. That’s a very different question. Growth, revenue, momentum — they can all look great on paper and still leave you feeling completely hollow.

So I made changes. I stopped building things that made me feel awful, even if they paid well. I stopped hiring talented people who created tension, just because they looked good on a resume. And I walked away from deals that promised opportunity but came with a heavy emotional cost. If it didn’t align with how I wanted to live, it was out.

I also made a rule for myself: only work with people I genuinely enjoy. That includes employees, investors, and even customers. I want to look forward to the people I build with. Life is too short to be surrounded by folks who drain you, no matter how “strategic” they may be.

Designing for Emotional ROI

We talk a lot about financial returns in startups, but not nearly enough about emotional ones. Profit is important, sure, but so is how you feel on a daily basis. If your startup makes money but leaves you miserable, that’s not a return. That's a loss.

Not every win needs to be scalable or investor-friendly. Some of the best parts of my week come from projects that don’t show up on our income statement. Maybe it’s writing something meaningful, or mentoring another Founder, or spending an afternoon building something with my hands. These things don’t make the business grow, but they make me grow — and that’s just as valuable.

When we design our business to feel good, not just perform well, everything gets easier. We stop constantly looking for an exit because we’ve built something we don’t want to escape from. Ironically, that's the kind of business that tends to be the most valuable.

Make It Mutual

For most of my Founder life, I measured success by how much discomfort I could tolerate. I wore sacrifice like a badge. But now, I’m trying to prove something else: that I can build something that feeds me back. That I don’t have to earn joy later — I can choose it now.

I want to build with people I like, solve problems I care about, and design a company that fits the life I actually want to live. I want to be able to step away in the middle of a Tuesday and sit in my own version of that pool, without feeling the need to justify it (to be fair, I'm still not quite there!)

Because the best startup isn’t just the one that works — it’s the one that works for you. And if you’ve forgotten that, maybe it’s time to give yourself permission to remember it.

In Case You Missed It

We Need a Strict Definition of Personal Success Every moment we spend pursuing an undefined goal is a complete waste of time — especially personal goals.

How Do I Design My Startup Around My Life? There’s very little preventing us from designing our startups around our life goals. It starts with us being very clear about what we want to achieve and then taking clear, small steps toward those outcomes.

I’m Killing Myself. How is Everyone Else Finding Work/Life Balance? We're supposed to believe that we can build a world-changing startup from nothing while simultaneously traveling to exotic places and enjoying our "best life." For most of us, that just doesn't add up. What's blowing us up, though, is how we approach the problem.