"I highly encourage all tech founders to go visit customers wherever they might be, particularly if you're based in Silicon Valley," Reeves said. "It's incredible to be here. But, absolutely, this environment can be an echo chamber at times."
He plans to write an online guide for tech execs on how they can tackle a road trip of their own. His investors could benefit, as well. Gusto is backed by some of the biggest names in tech, including Google Capital, General Catalyst, angel investor Ron Conway, and the founders of Yelp, Evernote, Instagram, PayPal, Stripe, and Dropbox, among others.
Source: Gusto
In addition to making better product decisions, Reeves said Gusto can now "avoid some of the pitfalls" that exist when founders focus on "the numbers of Silicon Valley."
"Silicon Valley gets caught up in discussing valuation and head count, but these are not success metrics. They are a byproduct of the actual topics that matter, such as, 'Do your customers love your service?' ... 'Do your employees feel proud to be part of your company?'" Reeves said.
His visits with small businesses across the country reminded Reeves that the most valuable conversations at the workplace revolve around people. The trip reinforced his commitment to talking to customers.
"All that matters is solving a real problem, and doing it in a way that you're proud of," he said.
This philosophy will also inform how the company hires new people and provides feedback through meetings and goal-setting, according to Reeves.
Reeves could have spoken with far-flung customers on the phone or over email, "but that doesn't mean there's still not value in meeting in person," he said.
They ate fried frog legs in Little Rock, danced in Nashville, and staged a Nerf gun fight at Paws & Stripes, an Albuquerque-based company that provides free service dogs for military veterans with post-traumatic stress disorder and brain injuries (and uses Gusto software).
When they weren't meeting with customers, the Gusto employees passed the time cutting together video from their pit stops and writing notes for future blog posts.
Along the way, Reeves noticed a recurring theme. The small business valued customer satisfaction above the bottom line. "It wasn't even a choice," Reeves remembers.
In Mobile, Alabama, a pool and spa installation and maintenance company told the Gusto employees about a recent storm. They urged customers not to use cleaning solution in their pools before the storm, because it would get washed out and wasted.
Reeves said they could make more money if customers went through cleaning products faster. But this company knew their customers personally and didn't want to screw them over.
"This is their business. It's a small community," Reeves said. "We need to learn from them."
Unlike Mark Zuckerberg and Sam Altman, Reeves steered clear of politics. He said he was more focused on "people questions" and the things that matter most to his customers.
He also distributed checks for $1,500 for those companies to donate to a charity of their choice. Lots of the business owners invited family and local TV crews to the event.
At each planned destination, Reeves sat down with the business owners and asked questions like: "Do you remember making your first hire?" "How do you get customers?" "What drives you to keep doing this?"
Their itinerary included planned stops — like a bodega in Pasadena and a kombucha bar in New Orleans — as well as drop-ins at restaurants and cafés that use Gusto software.
Reeves planned a road trip to 11 cities and 10 states where Gusto customers live. The company rented a Winnebago for $4,000 and had it fitted with a temporary vehicle wrap.
For the trip, Reeves was joined by Mitch Houff, head of business operations; Jenna Carando, a designer; and Kira Klass, who does social marketing for the company.
Reeves got the idea for a road trip when he ran an experiment inspired by reality TV show "Undercover Boss." Over a few months, he shadowed a member on each of the 37 teams at Gusto and learned their jobs. He wanted to know his customers as well as his employees.
Reeves hypothesized that connecting with his customers might help him escape the Silicon Valley bubble. When you're embedded in the tech scene, he said, it's easy to get caught up in the numbers game. Founders worry about company valuations and employee head count.
This is problematic because being in the bubble doesn't help him understand his customers any better. He won't know how their software impacts their lives or the ways it could be better.
"If a tech company wants to scale, be mainstream, serve customers around the country and around the world, it is imperative for founders to go meet and see those customers," Reeves said. "A tech business is no different from any business. We exist to serve our customers."
He sold his first startup and launched Gusto, which makes software that puts payroll, benefits, and other HR needs in the cloud. It serves over 40,000 small businesses.
He says Gusto's mission is to make people's lives easier. According to company data, over 40% of small businesses get fined annually for making an error on their payroll tax forms.
