Daniel Goldstein

We raised a Series C at @trustandwill ! 7 years into the journey, an industry leading brand, and over 1M people on our platform—yet it still feels like we are just getting started. The majority of Americans still need a multigenerational plan, and we are here to help! I'm so deeply grateful for the last 7 years. I'm grateful for the team members, current and past, who drive our mission forward. Grateful for our amazing investors and partners who believe in our mission and category leadership, grateful for @codybarbo and Brian Lamb, grateful for every financial advisor who trusts us with their clients, grateful for every estate planning attorney helping our members, and deeply grateful for every family who trusts us with their multi-generational plan. We plan to use the money to continue to scale and invest in our industry-leading platform for families and financial advisors. Expect the platform to continue to get more intelligent, comprehensive, connected, and visual. We plan to hit our next milestone of helping 1M people/year in the next 24 months!

Pretty rad to see @trustandwill ranked in the #6 spot on @FastCompany'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 tuned for some big releases and announcements in the coming months.

@VladTheInflator Can you explain assumptions?

Buy a house or rent + investing Who wins?

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 with AI is a prerequisite, not a differentiator, so we are over-indexing on people who can think about what they're doing and why they're doing it. Here's why that matters:

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 invest in every single day. He'd give us money while he was alive because he wanted to see our joy, not wait until he passed away to find out if it mattered. But the money wasn't the point. The legacy was showing up. Teaching us what mattered. Building relationships while he was still here to be part of them. He understood something most people miss: The ultimate legacy is the people you leave behind and what you've contributed to their lives. That's the shift. Legacy isn't a destination. It's not something you worry about at the end. It's the choice to show up today and invest in the people around you. It's teaching values by living them, not just talking about them. It's making decisions that cost you something now but shape who those people become. Every day, you're either doing that work, or you're not. Legacy is a verb.

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.

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. Why? Because customers come to you with problems, and those problems typically come with emotions. Uncertainty, stress, confusion, etc. If you’re able to flip those emotions, you’ll build a company that truly matters. One Medical is an excellent example of this. They’re a healthcare company that realizes their customers are highly anxious. “Is something wrong with me?” “Am I overreacting?” “Will this be expensive?” “Will I be dismissed?” They reduced that anxiety with short wait times, transparent pricing, and other anxiety-reducing design choices that prioritize reassurance over complexity. That’s the difference between building impressive products and building meaningful ones. Most companies over-engineer features because they forget they’re designing for people.

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 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 already telling them how to solve it instead of asking what they think. It's a reflex. And it's a bad one. Because here's what I've learned: When people don't feel like they're being evaluated against a hidden "right answer," they think more freely and speak more honestly. Asking better questions does more than giving better directives. It shifts the dynamic from execution to ownership. And that kind of environment produces stronger ideas, healthier debate, and shared responsibility for the outcome. But it only works if you actually let go. Which is harder than it sounds when you're used to being the person with the answer. So yeah, I'm still working on this. Still catching myself. Still having to pause and ask instead of tell. But every time I do, the team gets better. And that's worth the discomfort of biting my tongue.

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

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 watching. In the conversations we’re willing to have instead of avoiding. This is one of the reasons why Trust & Will matters so much to me personally. It’s not about end-of-life decisions or estate planning, it’s about a way of living. Legacy is built through consistency, communication, and the willingness to think beyond yourself. It’s about recognizing that the way you show up today echoes forward. And those small, intentional decisions compound over time, long after you’re gone.

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

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 decision right, but it increases the odds and forces me to slow down. When I zoom out and think in multi-generational terms, the decision usually feels different. It’s less reactive and less about the moment I’m in. This also applies directly to Trust & Will, the relationships we have, and the kind of legacy we’re leaving behind. It doesn’t magically make choices easier, but it is incredible to make the hard choices for the long run and build something that matters. It makes every decision feel more intentional. Not perfect, just more grounded in what actually lasts.

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

Traditionally, leadership meant certainty and vision, today I think there’s another element that is just as critical, especially for @trustandwill: 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 something to be said about the significance of having forthrightness and openness when it matters. Nowadays, people are more connected than ever. They know leaders don’t have all the answers because, quite frankly, nobody does. That’s why leaders are often served best with honesty and vulnerability. Take Trust & Will for example: Openly talking about death is about as vulnerable as it gets. It’s easy to avoid hard topics like this. That’s why vulnerability-based leadership is so important today. If you start being raw about the uncomfortable yet necessary conversations in life, your team will follow your lead and reciprocate. Can it be uncomfortable? Yes. Can it also unlock growth and alignment? Absolutely.

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:👇

@InTheMoneyAdam Been following and investing with you for a couple months— love it! Keep up the awesome work

I'm keeping HOOD at 1% to put it in a corner of shame until it releases things that are made for adults. We're past the point where short selling pitches tents. Their rapid acceleration of offerings was promising, especially when cheap, now not so much. Also if someone could tell me to double check for typos before releasing investor updates, that'd be great. marketplace.joinautopilot.com/landing/1218/5…

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 for trying, progress slows to a crawl. When teams know they can test ideas, learn quickly, and adjust without getting in trouble, something shifts. People stop optimizing for safety and start optimizing for progress.  Honestly, that point bears reading a few times. When curiosity starts to win out over fear, it makes your company more adaptable, and more flexible. Especially in 2026 and beyond, these traits are going to be CRITICAL. I’ve also noticed people (especially A-players) respect being trusted with that kind of creative freedom. And over time, that trust quietly changes how people show up to their work.

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

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 things are moving, momentum starts to stack in a way intelligence alone never does. I’ve seen a lot of good ideas stall out because people were slightly misaligned. Different priorities, different interpretations, different pull. We think about this with our team and culture at @trustandwill all the time. When people feel sincerely motivated by their work, and know that they are making a difference, they are willing to do the good work needed to really grow and build. When alignment is there, everything feels lighter. And it creates an environment people can run with autonomy. And that kind of steady forward motion, over time, is usually the real difference between companies that last and ones that just sound smart for a bit.

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.👇