20 Questions

The CEO of Billion-Dollar Startup Gusto Believes Passion Should Come Before Revenue

The CEO of Billion-Dollar Startup Gusto Believes Passion Should Come Before Revenue
Image credit: Gusto
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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.

Imagine it’s the millionth time you’re describing your business. Would you have as much conviction and be as sincere about the mission as the first time you described it?

For Josh Reeves, the co-founder and CEO of HR startup Gusto, the answer is an adamant yes. “Gusto inspires me,” Reeves says. “It makes a difference in people’s lives and makes it better.”

However, the entrepreneur wasn’t always able to enthusiastically nod his head yes or speak with such confidence about his company’s mission and passion for solving a problem. Prior to Gusto, Reeves founded a startup called Unwrap, a SaaS company that “empowered brands to benefit from social media by providing tools to build, manage and deploy engagement programs on Facebook,” according to Reeves' LinkedIn. While it generated plenty of revenue, it lacked a vision Reeves believed in.

“It’s a stark comparison to me,” Reeves says, comparing this company to Gusto. “The passion was missing. There was a lack in fulfillment and a sense of purpose.”

After Unwrap was acquired in 2010 and a bit of self reflection, Reeves, along with two other entrepreneurs, set out to solve a problem he felt was a huge issue in small businesses: human resources.

“We came across this problem, because we each had our own businesses and other startups,” he says.

Launched in 2012 as ZenPayroll, the three co-founders initially created a third-party platform for small businesses to manage payroll for their employees. But after expanding its offerings in include workers’ compensation and health benefits, the team decided to change its name to Gusto. “Gusto is an enabler for entrepreneurs and people following their passion,” Reeves says.

In business for more than four years, the company has 300 employees and 30,000 clients and Reeves is just getting started. He hopes to continue making an impact on customers' and employees' lives while helping the business grow and maintain sustainability.

“I’ve been called the values founder in the past,” he says. “That’s what it’s all about.”

To learn more about what really makes this values founder tick, check out his responses to these 20 questions:

1. How do you start your day?

My schedule is waking up for sunrise. I usually spend the first 30 minutes in the garden. I find a lot of joy and simplicity in life from nature. It constantly grows without any of my input or contribution. It’s a reminder that the world is a lot bigger than anyone really envisions it.

It also gives me a chance to clear my head. It’s very easy to become reactionary in startup life -- to become tactical and overcome whatever obstacle. But there’s always a million puzzles to figure out, so I need the opportunity to just detach and think -- to have my mind daydream. I like starting my day with that mindset.

2. How do you end your day?

I end the day spending time with my wife. No smartphones.

Because of my schedule and her schedule it’s hard to say we’re just going to wing it and take three hours in the afternoon. So we try to be more proactive and deliberate. I’m not my best self if I don’t see my wife and spend time with her.

3. What’s a book that changed your mind and why?

The Monk and The Riddle by Randy Komisar, a professor of mine at Stanford. The book is about the purpose of life through his own experience.

He brings up the idea of an extended life plan -- the concept that somehow people think we’re going to do something now that might not be good but will enable us to do what we want in the future. But that mindset replicated over time means you never get to living the life you want. The main message is the journey itself matters. It’s the best way to build the best future.

4. What’s a book you always recommend and why?

Lord of The Rings. One of the best traits of a leader is being able to see the world through the eyes of someone else. Getting caught up in awesome fantastical worlds is fun, but it also gives you a chance to observe the world.

5. What’s a strategy to keep focused?

It’s valuable to at least once a year put down on paper how you want to spend your time, and then go through your calendar and see how you actually spent your time. It’s a great mechanism to see if you've become reactionary. It’s a great goal for someone with a startup to be proactive and not reactive, because it’s very easy for someone with a startup company to become reactive and feel productive. But the only way to be focused is to be proactive.

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

Something in the realm of construction or engineering. I was always interested in how things worked. It’s not just building it or deconstructing it. It’s wanting to improve it.

Related: With 250 Million People Visiting His Website Network Every Month, This Entrepreneur Shares With Us the Richard Branson Moment That Changed How He Ran His Company

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

The first time I became my own boss, in some ways I was my own worst boss. I was staying up all night. There was no boss telling me to go rest and take it easy. I worked in this intoxicating loop: I want to do it, then I’m going to do it and I did it. It’s fun, but it's not sustainable at all. I now need to set up time to step back and be strategic.

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

My parents more than anything. My dad was the academic (a teacher) and my mom the passionate entrepreneur. Teaching gives a unique perspective because you're constantly putting yourself in the shoes of someone else. My mom, being an immigrant, I was raised with a nothing-is-impossible mindset.

9. What’s a trip that changed you?

We went hiking in an area that’s one of the birthplaces of Japanese Buddhism, and it’s a 1,000-year-old trail. It looks like nature made the trail. It was a unique experience to be reminded of my own mortality, and the world we live in. Being around anything that's 1,000 years old relative to a company that is four and a half years old is a great reminder of not letting too much go to your head.

10. What inspires you?

At Gusto, I get joy seeing a customer benefit from what we're doing and knowing we’re making a positive difference in their life. There’s no other purpose to our business than making our customer’s life better. It inspires me to keep doing what I’m doing.

Also, seeing someone do something they never thought or knew they could do. At Gusto, that could be with a customer or giving someone more responsibility. Startup life is like running a train 90 miles an hour while building the train while laying the tracks. Gusto is not just me; it’s a collection of people with a shared belief.

Related: How Getting Fired Turned Into Sweet Success for This Entrepreneur

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

Technology and Education Connecting Cultures in 2003. It was me and a student from Beijing. We wanted to create a way for students to interact, get to know each other and connect through helping others.

Our first program was a two-week teaching institute with a middle school in China where half of the volunteers were U.S. college students and half were Chinese colleges students. They had to plan the program, run it and get to know each other. They built really strong relationships, while helping others. The organization now has many chapters and thousands of people have gone through it.

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

It was the summer before I went to college, and I wanted to pay for college myself. So, I worked at Muir Woods. My job was doing maintenance. In retrospect I’m happy I did it that summer, because I went from that experience to begin at Stanford, which is a very sheltered kind of environment.

It was meaningful for me to interact and talk to folks who had not gone to Stanford. I was able to go into Stanford with a broader perspective of the world. If I hadn't had that experience I would’ve been more susceptible to that sheltered mindset. I think another important lesson I learned from that summer was that there’s no one path. Life is long and full of many things you can learn.

13. What’s the best advice you ever took?

A lot of Randy’s advice and the book he wrote is that there is no single path. It’s about the journey itself. Ask the why. It’s a fantastic way to challenge why we’re doing something. If it’s for the sake of doing something, that’s not a good reason.

My advice is to create a time of introspection because no one else will create it for you.

14. What's the worst piece of advice you ever got?

The worst type of advice is when anyone gives advice based on their own experience and presents it as fact, or the only way to do it. It’s all contextual. There is no one path to doing something.

15. What’s a productivity tip you swear by?

What I’ve done since college is after every interaction or conversation, I’ll write down some quick notes after the conversation. What I found is the act of writing it down turns it into more of a long-term memory.

16. Is there an app or tool you use to get things done or stay on track?

I use Google calendar. I create different calendars and put them in different views. I have a work calendar, a personal calendar and a to-do calendar. That’s a way for me to actually have one place to look, especially for the to-dos and the events.

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

Work-life balance implies to me a zero-sum game, and it's not. If work is better, life doesn’t suck and if life is better, work doesn’t suck. Work can and should be a part of life. Work-life as a part of living is making sure that I spend time on things I want to do, and I’m passionate about. Making sure I’m doing what’s important to me and making sure how I spend my time matches what is important to me.

18. How do you prevent burnout?

Taking a step back is a huge part of it. I travel, and I go into nature -- like when I go into a park every Sunday. Twice a year I do some international travel for two weeks and exercise is also a part of being healthy and balanced.

19. When you’re faced with a creativity block, what’s your strategy to get innovating?

A change of scenery and environment. When I talk to entrepreneurs and they are trying to come up with something innovative or a new idea, my biggest piece of advice for them is to not lock themselves up in a room for two weeks. There’s not much value in being in closed off environments. You want to be around your potential customer or something you’ve never seen. We need something different to drive creativity. For me, a lot of it’s visual.

And get enough sleep. It’s impossible to get work done or be created without enough sleep.

20. What are you learning now?

I’m learning a lot about scaling. We’re a 300-person company, and we want to stay true to our values. Everything needs to be rethought as we get to a new stage as an organization. There’s this balance in really empowering my teammates, my employees and entrusting them.

This interview was edited for clarity and brevity.

Edition: October 2016

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