1. What have you found most challenging as a leader?

I find the balance between the aims of our investors and the complexity of the market we are selling into to be quite challenging at times. Our market is heavily regulated and moves slowly, but it is also massive. It requires patience and investment of time to reach a large scale, but it is also very sticky, with high barriers to entry for new entrants. Funders with patience could be tapping into a market with very large returns, but there is a perception that if things take time, there isn't product-market fit. It is difficult because for the investors they are looking for signs that you are not spinning wheels. Demonstrating traction when deals take a long time to close can be complex, especially since most companies in the sector aren't building for what the industry is looking for.

2. How did you become a leader? Can you please briefly tell the story?

I started my first company when I was 12 years old. I recognized a need in our neighborhood to make it easier for parents to get a babysitter without calling 20 different households. It was essentially a low-tech "Uber for babysitters" in the 1980s. To me, being a leader has just been being willing to take the risk to make the first step and shielding your employees from the brunt of the risk of running a startup.

3. How do you structure your work days from waking up to going to sleep?

Last year I went through 6 months of chemo and that has really changed the structure of my days. When I wake up in the morning, I do some light exercise while watching the morning news. I usually get some coffee and work through emails that I didn't have time for the day before until 10 am or so. I try to schedule calls with investors, customers, and the team between 10-4, and most days, I am on calls during that entire window. From 4-6, I try to block that off for work that I need to get done myself. 6-8 I may need to keep working depending on the intensity of the day but if not I go out for a walk or spend some time in my garden. By 8 my partner, a professor, is usually done with their work day as well and we like to watch documentaries on history of different eras. They go to sleep at 10 and I am usually up for a few more hours and spend that time reading or cleaning our apartment. I can't work the 80-hour weeks I used to before cancer so I try to balance work, family, and my health these days.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

When I was gone from our company for 6 months for cancer treatment, a number of the contracts I was working on fizzled out. I have realized from this that as a CEO I need to bring the team in early into a process so that new customers are not equating working with Trusty.care as working with me. This was a hard lesson to learn.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

This is likely not an obvious choice, but I have read several books by Pema Chodron. The one called "The Places that Scare You" had a profound impact on me as an individual and how I approach life and leadership. The book discusses how adversity and challenge happen in life, but how we relate to the challenges matters. Leaning into challenges, having difficult conversations, not letting people's expectations of you determine your emotional state. All of these are things that have affected me as a leader.

6. If you could only give one piece of advice to a young leader, what would you say to them?

Entrepreneurs talk all the time about taking care of their health, but they rarely take it seriously. For 20 years, I ran startups with almost no break. I thought I was taking care of myself, biking daily, weight lifting three times a week, but I didn't take care of the stress and had lost perspective. Last year, I was opening my Series A but had a surgery I needed to undergo. I almost canceled the surgery because of fundraising. If I hadn't had that surgery, they wouldn't have found out I had cancer and I would have died in 4 months. Take time for your mental health. Listen to your bodies. No company is worth dying for.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

It is not easy on a company for your CEO to suddenly disappear but as a leader when I had to suddenly take medical leave was a time when I was able to see how having crafted a certain culture and brought on people that I knew could perform made such a difference. It wasn't easy on the team but they knew the direction they were heading in and they doubled down on getting there in my absence. There is nothing greater than seeing that you set a stage and the people you brought to it are able to continue the work even when you are gone.