“When I think about the people that I have admired the most, I see that for them, leadership is a form of service and leading people is an inverted triangle. At my best, leadership is how do you enable those around you to be the best versions of themselves.”

Meet Lindsay Ullman, Co-Founder of Umbrella, a service that helps elderly adults stay in their home by connecting them to neighbors who help with daily chores. Before starting Umbrella, Lindsay worked for Google, GV, and Sidewalk Labs. We spoke to Lindsay about her non-linear career path across Entrepreneurship, VC, and Tech, how she started Umbrella, and her unique perspectives on identifying entrepreneurial opportunities for baby boomers.

Tell us a bit about yourself and your early career path?

I grew up in Corning which is in upstate New York. Throughout high school, I was very interested in politics and involved in campaigns. For college, I went to Yale and studied History. I didn’t think about my major in a vocational way and I’m glad I studied what I was interested in.

My first year out of college, I worked at Google in New York on ad products. I chose this job as I was interested in the world of media and wanted to understand the changing ad industry. After about a year, I joined Google Ventures. It was a great opportunity for me as it was during the financial crisis. I was able to change roles within Google, but move into something more entrepreneurial and exciting. I spent a fantastic 4-5 years there on the investment team and got a lot of room to invest in companies that I thought were interesting.

Your career path has been very non-linear. People will often say it is best to choose a field and stay in that. What is your take on going deep vs. wide?

I think it is hard to know at the time exactly what you should be doing and everything becomes much clearer in retrospect. In the moment, its best to go with your intuition and choose the job where you will learn the most and where you will stretch the most. In retrospect, you see certain patterns in your career and in my case, I was always looking for places where I could have a lot of room to run. For example, my job at Google Ventures was essentially ‘choose your own adventure’ since I could decide whether I wanted to focus on investing at a certain stage or in a specific asset class. I’ve never really had a job description and that has helped a lot now with Umbrella.

What motivated you to attend business school? How did that lead to starting a company?

I went to Harvard Business School with the intent to do something entrepreneurial. While there, I looked at two categories of business: one was an idea around better utilizing locals to help travelers craft authentic experiences and itineraries, and the other was a recruiting platform to better help students find interesting jobs after college. While at HBS, I was introduced to Sidewalk Labs which is Alphabet’s urban innovation organization.

While at Sidewalk, I met my co-founder Sam and became interested in the aging space. Serendipitously, we started Umbrella thanks to a conversation inspired by his Grandmother. She told Sam about how she was part of this organization that helped her take care of her house and stay in her home. Sam told me about this and we felt like it could really be replicated in scale. We worked with that organization’s founder to use that as a model that we could bring to many more places. Since then, we raised money at the end of last year, launched our pilot in the Fall and fully launched in New York this past Spring.

What advice would you have for young women navigating their career?

In my opinion, the best combination at a particular job is the ability to learn and to bring your ideas forward, as well as people who will support your success along the way. Lately, I would add the criteria that I’ve been increasingly thinking about how to have impact and be mission-driven.

What’s the impact that Umbrella is trying to have?

Umbrella’s mission is to allow people to stay in their communities as they age. As people get older, they want to age in place, but often cannot take care of their home. Umbrella connects these individuals to neighbors who can help them with these tasks and are willing to help at an affordable rate. Right now, we connect older individuals with neighbors who can help them with small jobs like home repair, but this is just the first part of a larger vision to help people stay in their communities.

What is the broader vision for Umbrella?

Like other life stages (e.g., getting married, having children) there are many facets of life that are different about aging. We want, in the longer term, to help our customers prepare for this life stage. For example, a lot of our customers are thinking about what to do as they age, but want to stay in their community – should I stay in my house? Should I downsize? What are my options?

Right now we are focused on helping our members with daily tasks, but we want to address all of these issues our customers are grappling with. We also hope that more companies will enter this space. There are ~50 million individuals who are 65+ in the US today and that number will be 80 million in 20-30 years. This demographic is increasingly digital and has disposable income. This is a huge market and we are hoping to see companies arise in the healthcare space, housing space, etc.

Can you talk to us about your view of leadership? What from your background informs your style of leadership?

I still make mistakes everyday. I am a young, first time manager and leader.

But when I think about the people that I have admired the most, I see that for them, leadership is a form of service and leading people is an inverted triangle. At my best, leadership is how do you enable those around you to be the best versions of themselves. I am far from mastering that but that’s what I hope to do.

Who are/were your mentors and what did they teach you? Did you have any great female mentors?

I’ve learned a lot from observing founders that I really admire. For example, I saw Alexa von Tobel of LearnVest really embody that idea of leading by creating a space for her team to be successful. There are some people who helped in brief ways. When I was at Google, Marissa Mayer inspired me to go to GV. Even though she didn’t know me that well, she said, “Hey, I can make this happen for you.” No one would ever know she did that but Marissa clearly felt that part of her job was to help people.

Heather Fernandez from Solv and Stacy Brown-Philpot at TaskRabbit are both amazing leaders who manage to bring warmth and high standards. Stacy is one of the most empathetic but direct people I know and that comes from caring about the people around her. I did not use to think that duality was possible, but I’ve come to see that that is normal and, as a leader, you can be caring and have super high standards.

Fire Round

If you could have someone do one Umbrella-like task for you for the rest of your life, what would it be?

There are so many! Definitely cleaning and getting groceries. When I buy a house, it will probably be yardwork.

What is your favorite book?

Personal History by Katharine Graham. She was the first female leader I got to know thanks to this book and she wrote a very authentic and open story about being a women who became such a powerful figure. I highly recommend it for all women and men too.

Who is the female entrepreneur or investor you'd most like to meet and chat with?

Katrina Lake. She was raising money when there were so few female founders and around a business that people didn’t understand. I would love to hear how she managed to have so much grit and keep battling through.

What is the best piece of advice you have ever received?

Advice from my dad: “Do your best and have fun doing it.

Madeline Keulen