If you are overthinking, write. If you are underthinking, read.

One thing building Trust & Will has taught me is that the strongest partnerships aren’t built on the deal, they’re built on alignment—and on loyalty over time. The offer matters. Roles matter. Economics matter. But they’re not the foundation. What actually holds a partnership

Still taking it all in…Trust & Will Holiday Bowl. Earlier this month, Trust & Will had the honor of being the Title Sponsor of the Holiday Bowl, and it was an incredibly surreal experience from start to finish. It was full circle for me. We started this company in San Diego

Great teams don’t avoid conflict… they rumble through it. Here’s why honest, ego-free debate and leading with curiosity is the real secret to better decisions and better work.👇

I’ve noticed something over the years… The companies that win usually aren’t the smartest ones. It’s the fastest moving teams. In order to move fast, alignment and autonomy are key. Clarity gives people a general direction. Alignment is what actually gets things moving. Once

One thing that’s really stuck with me while building a culture is how important it is to leave room for experimenting and trying new things. (not to mention, it makes it fun again) Not because all new ideas work, honestly, a lot don’t. But because the moment people feel judged

The best leaders aren’t the star players… they’re the coaches. Here’s why shifting from “team captain” to “great coach” is what actually makes businesses scale:👇

Traditionally, leadership meant certainty and vision, today I think there’s another element that is just as critical, especially for Trust & Will: Vulnerability. It’s core to how I try to opearte. And don’t get me wrong here, certainty and strength are critical. But there’s

After 17 years in the league, Matthew Stafford is officially an MVP. #NFLHonors | Invisalign

I’m obsessed with thinking generationally. And yes, kids definitely impacted this lens, but I try to look at decisions through a long arc. The Collison brothers at Stripe talk about “multi-decade abstractions” and it’s incredible. A long lens doesn’t guarantee I’ll get the

Founders often mistake speed for progress. Here’s why separating velocity from momentum, and learning to communicate wins, changes everything for your team.👇

Many people treat legacy as something measured by the wealth they have accrued at the end of their lives. In reality, it’s so much more. I think the real impact is built daily through habits, decisions, and relationships. It shows up in how we treat your family when no one is

The people who believe it’ll work out take bigger swings. And I’m a believer that this mindset is a competitive advantage.👇

The moment you stop pretending to have all the answers, teams start stepping into their best work. At least that's the theory. The reality? I still catch myself doing it all the time. I'll be in a meeting, and someone will bring up a problem, and before I even realize it, I'm

I built a company, and at the same time, I became a husband and a dad. Somewhere along the way, business lessons and life lessons stopped being separable.👇

The way I see it, companies over-engineer features and under-engineer human experience. Because the truth is, I don’t believe most customers are asking for more features. Don’t get me wrong, features are great. But an enhanced human experience is what customers really want.

As your company grows, your planning horizon has to grow with it. Vision is thinking years ahead, but execution is breaking it down into what actually happens next quarter.

Legacy isn't something you leave behind when you're gone. It's the decisions you make today that show up tomorrow. Growing up around my grandfather taught me that. He used to talk about "la familia" constantly, not as some abstract concept, but as something you build and

The rarest skill in 2026 isn't technical ability, it's taste. Judgment and taste were already rare in a completely human world. Now, as people hand over more of their thinking to LLMs, these qualities are becoming even more scarce. As we scale our team, operating efficiently

Pretty rad to see Trust & Will ranked in the #6 spot on Fast Company's Most Innovative Companies list for 2026. This is for the small and mighty category with companies with 51-200 employees. Our team is building some amazing technology this year to advance our mission. Stay