Why I’m Driving Across the US in an RV to Meet Small Businesses

This article was originally published on Inc. here.

Later this month, I’ll be doing a cross-country road trip to meet small businesses. That’s right, I’ll be driving over 3,000 miles in an RV, coast to coast, to hear from the amazing people Gusto serves — small business owners and employees from all industries, geographies, and walks of life.

Every time I talk with an entrepreneur who had the courage to start their own company, or someone who takes pride in working for a local business, I feel energized. Yet small businesses rarely get the same recognition that Fortune 500 companies do for offering great benefits and contributing to their communities. That’s why, as I make my way across the country, we’ll be spotlighting one business in each city and giving them an “Extra Mile Award” to celebrate how they go above and beyond for their team and community.

These businesses offer unique benefits, are thoughtful in how they’ve built their team, and create extraordinary opportunities for the people around them. A few of the winners include a non-profit that provides service dogs for veterans with PTSD, a family-run retro and specialty clothing store, and a preschool that was started in a home and has grown to teach over sixty kids.

The simple power of talking to people face-to-face

I had the idea for this trip last year as I was shadowing my teammates at Gusto, learning the ins and outs of all the great work that goes into serving our customers. But as we’ve grown to help over 40,000 small businesses run payroll, offer benefits, and take care of HR, I haven’t been able to talk to as many customers as I used to. I realized that I wanted to spend more time hearing their stories and talking with them in-person.

You can track my journey on this map, and if you’re interested in riding along with us, follow @GustoHQ on Twitter and Instagram (#ExtraMileAward). Feel free to share any recommendations about good eats or fun pit stops! I’ll also be posting personal reactions to the trip every day on Medium, and look out for more thoughts here on Inc.

Walking in other people’s shoes can help you become a more effective leader: you gain a different perspective and it’s a chance to focus on stewardship, not proprietorship. As CEO, my job is to empower everyone at our company to do the best work of their lives, while we work toward our common mission. As we’ve grown, I believe in continually “firing myself” from the various functional roles I’ve had in the company. Early on, I used to run our sales team, marketing team, business operations team, and more. Now that we’re larger, we’ve hired amazing people to lead these teams, and I learn from them every day.

While I’m on this road trip, I’m eager to learn from our customers. I’m sure I’ll discover all kinds of creative solutions that our resourceful customers have come up with to solve their day-to-day problems, and beyond that, I want to hear about their challenges and struggles too. In the digital world we live in today, I look forward to shadowing small business owners and employees in-person to understand what their work and lives are really like.

If you’re asking yourself right now when was the last time you visited your customers face-to-face and you don’t remember, then it’s probably time to get out of the office and do it.

But why a road trip?

A second goal of the road trip is to see many different parts of the U.S. and better understand the common values that connect small businesses owners of all kinds. I grew up in Silicon Valley and while I’m proud to live and work here, I also recognize that it can be an echo chamber at times. I’ve found travel is a great catalyst to take a step back, disconnect from the day to day, and see things from a different perspective. The power of travel inspired Gusto’s “Fly Away” program — which gives Gusto employees a free round-trip plane ticket anywhere in the world on their one-year anniversary. They have to use the benefit by their second anniversary, and the goal is for them to detach, take a step back, and come back from their trip a healthier person and teammate.

During the road trip, I will travel across California, Arizona, New Mexico, Texas, Oklahoma, Arkansas, Tennessee, Louisiana, Alabama, and Florida — and it will be my first time in many of these places. Each day I’m eager to learn from the people I meet, hear their insights about building thriving businesses, and also brainstorm what Gusto — and others — can do to help them.



Co-Founder and Head of Gusto. Building a company for the long haul. Our mission is to create a world where work empowers a better life. We’re hiring!

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Joshua Reeves

Co-Founder and Head of Gusto. Building a company for the long haul. Our mission is to create a world where work empowers a better life. We’re hiring!