Make More Happen

This CEO Says the Key to Being a Good Boss Is Getting Out of the Way

This CEO Says the Key to Being a Good Boss Is Getting Out of the Way
Image credit: DogVacay

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.

Aaron Hirschhorn, CEO and co-founder of DogVacay -- a website and app that connects dog owners to dog sitters -- certainly has a lot to juggle. Not only is he the face of an organization that has raised nearly $50 million, has approximately 100 employees and is booking millions of dog nights a year -- but he is also the father of three (and they’re all under 4 years old).  

Part of that chaos comes from Hirschhorn’s constant drive to make DogVacay bigger and better. Hirschhorn suspects that if you had asked him four years ago whether or not he would be satisfied with the current state of his company, he would have said yes. But he’s not.

“I'm not satisfied,” he says. “I think that we need to be doing things better, we need to be moving faster, we need to be in so many different ways, improved.”

Related: Bring Your Dog to Work Day Is Every Day for These 8 Companies

Despite the chaos, Hirschhorn has learned that the key to success is delegation. “You want to find good people, point them in the right direction and then get out of the way,” he says. “It's a hard lesson, especially when the company is my baby and I have a point of view about how to do things.”

DogVacay’s network of hosts, or dog sitters, have also motivated him to make the company stronger. “Individual stories of people who are doing something that they love, not just for the money, and doing amazing things with it, to me is the most inspiring piece of the business -- and not one that I really expected or thought about when we started,” he says.

We caught up with Hirschhorn and asked him 20 questions to figure out how he did it and what makes him tick:

1. How do you start your day and why?

I wake up at 5:45. I have a double cappuccino first thing, then I have an hour-long routine of stretching and core exercise. I have had a couple back surgeries and so doing that [hour-long exercise] routine in the mornings sets the tone for my entire day. It is super rejuvenating and recharging. It gives me perspective on the things that are important. So I get that done and then try to have a good hour of bonding with the kids before the craziness of work starts.

2. How do you end your day?

I am cuddling on the couch with my wife watching Game of Thrones, House of Cards, Last Week Tonight with John Oliver, Daily Show, anything fun. She makes me watch occasional reality T.V. shows, drink a glass of red wine and just try to sink into the coach and get ready to do it again.

I think a lot of people in my position will go home, spend time with the kids, and then spend another two to three hours online working. I do have my phone, but I try to really connect with her because that's our only time and that also is just critical. You have to recharge with your family. So my kids, my wife at the bookend of the day, again, puts everything into perspective as to what is important and what's not.

3. What is a book that has changed your mind?

I love books that help you understand or change your perspective on life, on humanity, on what it means to be a person, on what it means to be an animal. There are two books that I love. Life of Pi, where the main character grows up in a zoo and talks about what it means to be an animal in the wild and an animal in the zoo, and then he sort of experiences it on a journey. I just love the perspective on humanity there.

The other one is The Art of Racing in the Rain, which is a book written from the perspective of a dog. And it's just so pure and beautiful about how this dog views his owner. You get that the owner is a flawed human, but the dog doesn't see any of that.

4. What is a book you always recommend?

I have been recommending -- and maybe because I have had some problems sleeping as the stress of the business is sort of catching up to me --  is a book called No More Sleepless Nights. It puts insomnia into perspective. It's a really practical guide to having a better attitude around sleep. I have been recommending that a lot to people because it turns out a huge percentage of people I know suffer from insomnia and a huge percentage of the country, too. Very practical, not a business book, but it just affects your life in a huge way.

Related: How CEOs Optimize Their Sleep Schedule

5. What's a strategy that you use to keep focused?

Trying to be really discreet in setting one or two specific goals within a relatively short time frame and making sure I stay true to that. Otherwise it's really easy to get sucked into the endless cycle of emails, meetings and conversations where I think I'm accomplishing things but in reality I'm likely not.

I use Evernote, which is like a program where you can write down notes, goals and reminders. It's on the top of my to-do list; it's pinned up there.

6. When you were a kid what did you want to be when you grew up?

I wanted to be a doctor. I actually got pretty far.

I got into a couple of great schools (this was 1999-2000). It was the height of the dot-com boom and also the height of the HMO backlash, so every doctor was miserable. And every doctor I talked to was like what are you doing, don't be a doctor go to business school. I took that advice to heart.

7. What did you learn from the worst boss you ever had?

I have never had a boss that I thought was terrible. Maybe it's in the eye of the beholder, I am fairly good at doing what I need to do, but I don't have a boss that I hated or that was terrible.

8. Who has influenced you most when it comes to how you approach work?

Our first big investor, a gentleman named Bill Gurley, who’s a partner at Benchmark. For somebody who is an investor, and where typically venture capitalists are all about driving rapid growth and pushing to do lots of things, he is remarkably centered and focused on just doing one thing well. 

Many times over the past four years DogVacay has been presented with opportunities that seem interesting -- could be international, new service lines, partnerships. Chatting with him, it's quite grounding in the sense that what makes a business successful is all the hard work around getting your core business to work. There is never any shortcuts; you just have to keep focusing and grinding away at that. If you dilute that effort, you're not going to be as successful.

9. What is a trip that has changed you?

India. It is just another world. Along the themes of things that put your life into perspective, the way that the world has so many people, so many smells, sights, sounds -- and such poverty. It just opens your eyes to the way that literally billions of people around the world live, how different -- and frankly, how lucky we are.

10. What inspires you?

I'm inspired by our individual hosts. These are regular people, retirees, stay-at-home moms, professional pet sitters, college students, freelancers, just regular people who are doing something awesome. They're taking care of other people's dogs and welcoming them into their home like a member of the family.

I just saw one email today where someone takes all the money he earns and gives it towards a local rescue. Another one takes all the money earned and gave it towards a charity in Guatemala. These individual stories of people who are doing something that they love, not just for the money, and doing amazing things with it to me is the most inspiring piece of the business -- and not one that I really expected or thought about when we started.

Related: 21 Ways to Get Inspired (Infographic)

11. What was your first business idea and what did you do with it?

When I was 12, I was a magician and I was pretty enterprising. I had a little magic suitcase with a combination lock and business cards that said "have tricks, will travel." I don't think that business ever quite made it into the black.

When I was in college I was selling long-distance phone service to my friends and family. It was a multi-level marketing arrangement. That was terrible.

I was a personal trainer and a jujitsu instructor. I probably learned the most there about how to interact with people one-on-one and again finding individual motivation. I had another idea for a business, before DogVacay, which was around a marketplace for personal trainers and massage therapists which was actually a pretty good idea, probably a little early. We really didn't have enough velocity to get a good product out, iterate on it and get customers.

12. What was an early job that taught you something important or useful?

It's about the relationships. With personal training you've got to look at someone's individual motivations. Some people have a very specific weight loss goal, other people have a long-term health goal, other people are pushed by you yelling at them, other people are pushed by you giving positive feedback immediately when they do something right. Putting yourself in the shoes of that other person and understand those motivations is important and that transfers to today.

13. What is the best advice you've ever taken?

As the company started to get bigger, too many decisions flowed through me. It felt like I was accomplishing a lot, because I was making a lot of decisions but in reality I was just taking away ownership from people who should otherwise have had it and slowing things down.

As the company has grown the best advice is to delegate, to get stuff off of my plate.

14. What is the worst advice that you've every received?

I got back surgery in 2008 that I should not have gotten. It made it worse. I thought there was a shortcut, whereas if I had been doing the things I'm doing now, I wouldn't have needed surgery. In general, life is like that, there are very few shortcuts.

It's not a direct analogy, but DogVacay could partner with a bigger pet food company for example, but it wouldn't be the single thing that quintuples DogVacay. There are just no shortcuts, and I want to always remember that.

15. What is a productivity tip that you swear by?

I try to get out of email for a few hours a day and just focus on other things. Close it out. Meet with other people. Talk to people. Walk over to someone's desk. Do those things instead of email.

Related: 4 Productivity Tips That Changed My Life This Year

16. Do you use an app or any productivity tools to get things done?

I do like Evernote a lot. I keep my life in there -- everything from to-do lists to memos to photographs and documents.

Other than that, I am a huge face-to-face or phone call person. When you get into the world of all these other shared productivity tools, they're great, but for me working as a CEO it's more about talking to individuals, talking to small teams and doing that in real life.

17. What does work-life balance mean to you?

I'm an introvert, so being the CEO of a company where I have to be the face of the company, do press interviews, stand in front of the whole company and be motivational -- all those things are actually pretty draining for me. I need to find ways to recharge and to me that's personal time, mostly exercising. I have to find time for exercise, to stay healthy, clear my mind, and have to find time for family. I literally schedule it like I would for any other meeting, and I think that's a really good way to find balance.

18. How do you prevent burnout from work?

There have been times where I have worked 12 to 14 hours a day and not seen my wife and or family. That doesn't work. You have got to get away. You need perspective. So if things are slowing down, or if I'm not sure what to do, I will try to get away. Even if it's for a weekend, afternoon walk, whatever it is.

Also, talk to other people. I like talking to other founders about their problems and challenges, because the things that I'm going through, other people have also gone through. Get out of the echochamber of your own company. There is a lot of external ideas that we don't have. Getting away from that and talking to people outside of that -- outside of the industry, outside of your close circle -- is really good for generating new ideas and new perspectives.

19. When you're faced with a creativity block what strategies do you use to be innovative?

Get away. You're not going to come up with the answer sitting at your desk and thinking or Googling. Get out of the office, get some different perspectives. I talk to different people. Getting outside, hearing other perspectives, hearing how other CEOs have thought about similar transformations in their company, how they have weighted the various options and decisions, often helps me.

20. What are you learning now and why is that important for the future?

I have an MBA from UCLA, and no knock to UCLA, but this is my real MBA. I have learned so much. I have probably learned more in the past year than I had in the first three and a half years of the business. As everything gets bigger, everything gets harder. I think that we need to be doing things better, we need to be moving faster, we need to be in so many different ways, improved. And so why is it important to me? Well obviously I have a huge personal ownership in this company, but more than that, I have an obligation and a responsibility to our employees, investors, customers and hosts. All that stuff is important and ultimately when the business is healthy, all those constituents are successful.

Related: Why Your Neuroticism May Be the Key to Your Creativity

This interview was edited for brevity and clarity.