Entrepreneur. Writer. Attorney. Father. Founder.

Joined February 2009
If you're as old as I am, and lucky, you've got about 1,500 weeks left on earth. On the Founder's Story podcast with Daniel Robbins, I explained why thinking like that makes the little decisions in your life easier. youtube.com/watch?v=X4JXy4Wp…
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Clarity is worth more than urgency.
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Invite people who should know each other instead of people who already do.
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Kids can't fake attention. Every leader should spend one season coaching to learn to earn it, practice after practice.
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One advantage of staying in the game for a long time is realizing how many things simply take longer than you expected. Most overnight successes look a lot less sudden when you've watched them for a decade.
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Most people think resilience means pushing through obstacles. I've found it often means slowing down long enough to understand why they're there in the first place. Every setback contains information, but only if you're willing to look for it.
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One of the healthiest shifts I've made as a founder was separating my identity from the numbers. Revenue is feedback. Growth is feedback. Neither of them gets to decide who you are. They only tell you where you are.
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I've started thinking about life more like a series of experiments. The goal isn't to prove you're right. It's to create enough uncertainty that you learn something you couldn't have predicted. Confirmation is comfortable. Discovery usually isn't.
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The hardest part about focus isn't deciding what to pursue. It's saying no to things that would probably work just fine. Most opportunities aren't distractions because they're bad. They're distractions because they're good enough to keep you from the thing that matters more.
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I think one of the most valuable business skills is resisting the pressure to react immediately. Most problems don't require a faster answer. They require a better observation.
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The internet has made it incredibly easy to have opinions about things you've never tried. Experience is becoming underrated. I'd trust someone who's done the work over someone who's only mastered talking about it every time.
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We spend a lot of time talking about productivity and not much time talking about attention. But attention comes first. What you consistently notice shapes what you build, what you believe, and eventually who you become.
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One thing I've learned from building companies is that every system optimizes for something. If you don't decide what that something is, the system will decide for you. That's true for businesses, technology, and probably people too.
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The internet rewards people who answer fast. Life rewards people who ask better questions. Curiosity has a longer shelf life than certainty.
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A life that feels good is worth building. But every so often it's worth asking: am I driving, or just being carried?
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Estate planning isn't just about transferring assets. It's about deciding what beliefs, values, and stories survive you.
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Artists investing privately in AI while avoiding public association tells you something. Pay attention to the gap between conviction and positioning.
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The most important things we pass on to our children rarely appear in a trust document. Values don't go through probate.
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When nothing feels wrong, it's easy to stop asking if it's right. Comfort without examination is how drift disguises itself as stability.
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Life gets better when you stop treating preparation as the destination. The point of planning isn't planning. The point is having a life worth showing up for.
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