The most valuable lessons I've learned haven't always come from winning

I spent my Silicon Valley career on the winning side of the table. Five company exits. Hard work, good timing, and enough luck to know the difference. I thought I understood how to build.

Then I became a founder. And I came up short.

On February 12, 2023, I sent the note every founder dreads. After five years, ReadyUp, my startup helping brands reach audiences through Twitch and Discord creators, was done.

I thought I was finished.

After ReadyUp, I retired. I started looking for ways to give back. I wasn’t looking for another company.

Then I came across a number I couldn’t walk away from: 70% of people who are grieving don’t get help or support they need. Help exists, but too often it doesn’t reach people in a way they can use. I know this from my own experience losing both parents when I was in my twenties and my oldest brother in 2017.

My co-founder Jeff Kimball, one of the country’s leading grief support experts, had spent his career trying to close that gap. We started talking. And I realized I couldn’t sit this one out.

But before I jumped in, I had to understand what had gone wrong. I wasn’t going to repeat it.

Introspection: the uncomfortable question I had to ask myself.

ReadyUp had real partners like ESL Gaming, NBC Olympics and the National Basketball Players Association. We had momentum. We had a team that believed in what we were building.

So why did we fail?

I spent a long time sitting with that question. And the honest answer, upon reflection, was obvious: we were trying to do too many things. Every new category we entered looked like an opportunity from the inside. But it wasn’t. When investors started asking for a single crisp story about one thing we did better than anyone, I didn’t have a clear response.

Instead, I had several half-stories. No single answer.

The market didn’t kill ReadyUp. It exposed our lack of focus.

The lesson fit on a sticky note: Keep it simple. Do one thing really well.

It sounds obvious. But it’s a common mistake entrepreneurs make. I made the same one.

Doing it differently this time.

When Jeff and I started building Empower Change and The Healing Center, that lesson shaped every decision.

We spent two years understanding the problem. At ReadyUp, we built before we were sure. This time, we worked to understand what we were solving and for whom before we entered the hospice world.

We picked one customer. Hospice organizations already walk alongside families through the end of life and bereavement. The Healing Center helps their teams extend their reach through on-demand peer support and practical resources. We sell to the hospice, and the hospice brings us to families. That gives us one clear path to the people we want to serve.

We kept the first version narrow. Our beta serves one population—people affected by cancer in one language. “Everyone” is how you end up serving no one well.

We address one problem. We help people who aren’t getting support take the first step, then connect them to resources that already exist, including their hospice’s own bereavement team. We’re a partner to the hospice team, not a replacement.

Now, when another opportunity comes along, I have a question to test it against: Does this make us better at the thing we set out to do, or give us another thing to do?

What focus has changed.

Less than a year ago, Jeff and I walked into our first hospice industry conference with a grief program idea, no product, and zero meetings scheduled. We were outsiders.

This past August, we showed two hospice organizations an early version of The Healing Center. In under 45 days, both signed letters of intent as strategic product development and beta partners.

Those commitments are an encouraging start. Several other hospice organizations are interested BUT we still have to prove what the platform can deliver for hospice teams and the people they serve.

But we could already see the difference in those conversations.

When a hospice leader asked what we do, we had one answer. And it also addressed their business problem of scaling support.

Why I want to get this right.

In addition to my parents and brother, unfortunately, I’ve experienced a lot of loss. I know what it feels like to grieve quietly, without navigation, without someone who’s been there.

I came out of retirement because too many people still face that silence.

Purpose and profit pull in the same direction here. The more families we help, the stronger the business can become. That’s worth building carefully.

The mission makes me want to help everyone. Experience reminds me that we have to earn our way there by doing one thing really well.

That’s what I’m carrying into Empower Change. You can learn more about us on our website but if you’re interested in getting involved, please message me.