I left MIT Sloan after my first year to build Modalyst. I had a Dean's Fellowship that covered my tuition, and I knew what I was giving up. But I'd met my co-founder, we saw a change coming in retail, and I wanted to find out whether we could build something around it. We launched the following year. I never went back to finish the MBA.

Our first idea was for physical stores. We thought independent retailers could get better access to suppliers if we brought their purchasing power together. We built a two-sided marketplace around that belief.

It was hard to make work. We added suppliers and products, and some of the numbers gave us reason to keep going. But the business underneath those numbers wasn't getting strong enough. There were moments when we came close to failing.

Meanwhile, online selling was taking off. Platforms were making it remarkably easy to open a store, but opening a store and becoming a seller were two different things. New merchants still had to figure out what to sell, where to find it, and how to get started without tying up money in inventory.

We could see that problem in the conversations happening on Modalyst. Merchants were asking suppliers for photos and descriptions before they bought a product. They wanted to see whether they could sell it first.

We had built a way to help stores buy. What merchants needed was a way to start selling.

Acting on that meant changing much more than a feature. We had to rethink the customer, the product, and the business we were asking our team to build. We had to bring our board and investors through a new direction when we couldn't promise where it would lead. By then Modalyst was a real organization, and a pivot affected the people who had committed themselves to the first idea.

We made the change. Modalyst grew to serve more than a million merchants and built partnerships with Alibaba, Shopify, Wix, and others. Wix acquired the company in 2021.

I'm proud of where it ended up. I'm just as proud that we changed course while the outcome was uncertain. Seeing the opportunity was one part of the job. Doing what it took to pursue it was the harder part.

After the acquisition, I stayed on as a VP and GM leading Wix's dropshipping and print-on-demand businesses. Modalyst had reached about 60 people, so I knew what it meant to build and lead a team. Wix presented a different challenge: a global customer base, a core organization of about 25, and work that depended on many more people across product, engineering, operations, marketing, and partnerships. The teams and partners involved spanned four continents and nearly a dozen countries.

The question I cared about was familiar. Wix could bring merchants into the product, but were we helping them become successful sellers? A merchant could sign up, browse a catalog, even add products to a store, and still be a long way from making a sale.

We looked at the whole journey: how merchants discovered the opportunity, chose products, built a store, launched, made sales, and stayed active. We improved onboarding and the path through the product. We worked on recommendations informed by a merchant's goals, industry, and customers, and on store concepts that gave people a more useful starting point than an empty storefront.

None of that was a single team's project. Supplier quality, product selection, pricing, inventory, fulfillment, and the merchant experience all touched different parts of the business. My job was to get us clear on the problem and the priorities, give teams room to solve what they knew best, and keep us accountable to whether merchants were actually making progress. Over time, we improved conversion through the funnel roughly fivefold and grew revenue by about 150%.

At Modalyst, I had often been close enough to a problem to see it for myself. At Wix, I had to build the conditions for other people to spot problems early, use good judgment, and act without waiting for me. I couldn't touch everything, and trying to would have slowed us down. That was probably the biggest change in how I led.

Now I'm building Heirluum. After the acquisition, I went through the process of creating my own estate plan and was surprised by how difficult it was. The more I looked, the more interested I became in what happens beyond the signed documents: whether a plan remains useful as a family changes, and whether the people who need it can actually find and understand it.

I came into the space without years of estate planning experience. That means I have a great deal to learn from the people who do this work and the families who depend on it. I also know from experience that fresh eyes can be useful if you're willing to listen closely enough to discover where your first assumptions are wrong.

That's the part of building I keep coming back to. You see a possibility, you make a bet, and then the work teaches you what you missed. The question is whether you're willing to change what you're doing when it does.