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What This Founder Does to Stay Completely Focused When he needs to focus, HomeHero CEO and co-founder Kyle Hill turns to a specific pastime to help get his head back into the game.

By Nina Zipkin


Editor's Note: Entrepreneur's "20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders

Our population is one that is aging. According to the U.S. Census Bureau, as of 2014, there were 46.2 million Americans that are 65 and older, and they make up 14.5 percent of the population.

As the United States becomes home to more senior citizens, the need to provide them with the right care becomes a growing concern, so much so that home health care, outpatient and ambulatory health care services are among the fastest growing industries in the nation.

After dealing with the time intensive and stressful process of finding the best and most responsible caregivers for his grandmother, Kyle Hill wanted to help the millions of people he knew could relate to his experience. So in 2013, Hill and co-founder Mike Townsend launched HomeHero in Santa Monica, Calif.

HomeHero is a platform that allows people to streamline what can be a draining hiring process for non-medical home care providers. The site allows users to watch video interviews of prospective caregivers before meeting them in person. And after they are hired, users can send payments and get daily text message updates about how their family members are doing.

Over the course of three years, the service has provided more than more than 1 million hours of care to thousands of seniors and their loved ones.

We caught up with Hill for our 20 Questions series to find out what motivates him and makes him tick.

1. How do you start your day?
Slowly; I'm not a morning person. I don't take meetings before 9:00 or 10:00 am, and I don't check email until about noon. But I like to collect any new information, whether its news or updates from the company [before I get to the office], so I check Slack early, and I try to get a good breakfast in. When I get to the office, I spend at least 10 minutes greeting everybody and checking in, because it's important to focus on the human interaction side of the company.

2. How do you end your day?
I love working out at the end of the day when I've conquered my day. I have to do something active, and I have to do something that fully immerses my brain to get my mind off of work.

I also play a lot of chess online or on my phone. I've been playing since I was little, and I really enjoy that because it takes 100 percent of my focus. It forces me to not think about work.

3. What's a book that changed your mind?
Black Swan by Nassim Nicholas Taleb. He talks about how we can underestimate highly improbable events and their impact on the world. I look at what I do as a highly improbable event. I often feel like an anomaly or an exception.

I'm an African American CEO raising $23 million in funding in the healthcare industry. It's just extremely unlikely. We live in a world where 17 percent of black male adults even have a college degree. I love thinking about, "what if we are the ones to make this massive change in healthcare?" I really hold onto the belief that these highly improbable events have the chance of occurring and when they do, they have such an impact. I get a lot of confidence and inspiration from that book.

4. What's a book you always recommend?
David and Goliath by Malcolm Gladwell is a book I often recommend to my employees. When you have somebody that is predicted to underperform or fail and ends up prospering, sometimes we have advantages that other people don't see or understand. I really like to encourage my employees to leverage their skills. You don't have to be the best engineer or designer, but the things you are good at, let's leverage them. It plays into this concept of comparative advantages. If you have a company where people are focusing on the areas that they are best equipped to do that job, they are going to succeed.

5. What's a strategy you use to stay focused?
I really like the app Momentum. It's a Chrome extension that allows you to create a to-do list. And I try to keep it under five items. I love checklists, because they help me stay focused.

On a higher company level, one of our policies is that during our morning meetings, every department announces what they are going to do for that day. And then the next day you reconvene and check in and say, "Did we do what we said we were going to do yesterday, and if not, why not?" If you say out loud something you are going to do, you're more likely to do it versus if you just tell yourself.

6. When you were a kid what did you want to be when you grew up?
I think every young boy wants to be an athlete at some point in their life, and I grew up admiring Michael Jordan and Scottie Pippen. But my father is a professor, and he put in my head pretty early that the likelihood of being a professional athlete wasn't very high. I think he got me understanding that there were so many things to do in the world.

I always liked drawing, and I think being an architect is the idea I held onto the longest. One of the most exciting things I did as a kid was build a treehouse in the backyard. My dad just gave me free rein to do whatever I wanted with it. For me, building the treehouse was the most exciting part of having a treehouse, or even playing in it. That lends itself a lot to my personality now -- I love building things.

7. What did you learn from the worst boss you ever had?
The worst boss I had was actually a soccer coach I had in high school. I wouldn't say he was a bad coach, but he yelled at me a lot. I realized that was something I could not handle. So my dad ended up pulling me from the team. I didn't understand it at the time; I thought it wasn't a big deal, and I had a tough skin.

But my dad was adamant about this, he said, '"I don't want people talking down to you because it hurts your self confidence. I need you to have the highest self confidence going into in everything you do in life; otherwise you're not going to want to do it."

I think it lends itself to being treated with respect and dignity. My dad said, "You can be stern, you can bench my son, you can take him aside and tell him what he needs to improve on. But don't publicly reprimand him." Even to this day, I tell people, "If you're upset with me, whether it's my co-founder or an employee, talk to me like an adult."

8. Who has influenced you most when it comes to how you approach your work?
The CEO of Social Capital, Chamath Palihapitiya. He was one of the first to write a check to HomeHero. I trust what he says about growing company culture and ethics and establishing it early on. He encouraged us to take a team retreat, two day offsite, to help figure out our identity.

Related: 3 Team-Building Secrets of Successful Small-Business Owners

9. What's a trip that changed you?
My trip to South Africa. I studied abroad there in 2007. It helped me establish my independence. I felt like I grew up a lot there, I just saw the world through a different lens.

10. What inspires you?
I really enjoy watching Elon Musk, specifically what he is doing with SpaceX. SpaceX is so inherently, crazy, risky, expensive, it takes someone slightly insane. He's someone who blows up rockets and has the audacity to do it again. Every time things get really tough, I think about blowing up a $5 million rocket and think it could be worse. If it's difficult; you're probably doing it right. I'm inspired by the people that are doing really impossible things.

11. What was your first business idea and what did you do with it?
In high school, I found a repository of Girl Scout cookies. I bought $1,000 of cookies from a warehouse after the season was over. I bought them, held onto them in a freezer and sold them on eBay during the offseason for $20 a box. I learned a lot about seasonality and supply and demand.

Related: 6 Actions You Can Take Every Day to Build Your Self-Confidence

12. What was an early job that taught you something important or useful?
My first job out of college I was working in banking. I liked it, but I learned that I didn't like playing the stock market, because I felt like I was gambling. I didn't have any influence on the outcome. If I'm going to bet on anything, I'm going to bet on myself.

13. What's the best advice you ever took?
The last company I started, after we sold the company, one of our investors in HomeHero looked back at what we did right and wrong. We found that we tried to scale our operation to three different cities, when we didn't have it working in one city. With HomeHero, we spent the three years of the company just in Santa Monica and Los Angeles, just took a much slower approach to scale, refine process and perfect the business before scaling. I think that is the best advice I ever got.

14. What's the worst piece of advice you ever got?
It could be very bad advice in the wrong context: ask for forgiveness, not permission. It is good advice if you're scrappy, but if you work in healthcare, if you work with government money, that is terrible advice.

15. What's a productivity tip you swear by?
I think the biggest one is stay off email; it's just things other people want you to do. Pick two times a day to check email.

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
I swear by Dashlane. It's a password manager. I never have to remember passwords, and you can share passwords with other people without actually giving them the passwords

17. What does work-life balance mean to you?
I think decompression is extremely important, I realized that I'm a grump when I come home and can't fully be present in that next activity, so I need a period of decompression between work and going home. That's my transition out of work; otherwise, I bring work home with me.

18. How do you prevent burnout?
Exercise and diet are the biggest two. If you eat well and exercise, you're going to perform better. Also, take the good and bad news with the same level of emotion. I never get too excited. If you always get the highest highs and lowest lows, you're going to break. Be a shield for the company, and don't get too worked up, because it is a long ride.

19. When you're faced with a creativity block, what's your strategy to get innovating?
I turn to diet. If I can't focus or concentrate, usually I eat an apple or take a walk. If I can't concentrate, I'm usually hungry. Making sure you're in a focused environment, you've eaten, you're not antsy -- it's a combination of those things.

20. What are you learning now?
Managing a big team is something that I'm learning to do. I hired all of our employees, [and as we grow], it's important to keep my relationships with employees personal. That's why I start my day greeting everyone; it helps me feel a little more grounded.

Nina Zipkin

Entrepreneur Staff

Staff Writer. Covers leadership, media, technology and culture.

Nina Zipkin is a staff writer at She frequently covers leadership, media, tech, startups, culture and workplace trends.

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