Brand Story - Passages to Success is building up the small-business community by doing the hard work and having a good time.
One Sunday in February 2019, friends Ben Surratt and Jonathan Kaylor were hanging out with their families, and Surratt mentioned he’d always wanted to start a podcast. “What would it be about?” Kaylor asked. “Just this,” he said. “Talking business and drinking beer.” Kaylor loved the idea. They started recording that spring. Jason Knopp was one of their first guests, the three had such a good time that, “as the joke goes, he never left,” says Kaylor.
The podcast Business Over Beer was launched in September 2019. It was local, in-person, and fun. The idea was to be a resource for small business owners in the Vancouver, Washington, community by telling stories about the ups and downs of running a business. In early 2020, Kaylor, Surratt, and Knopp were starting to expand the podcast with live events and had just signed their first sponsor when the pandemic hit. As the year progressed, the podcast space started getting crowded, and they wanted to find another way to stay engaged. “We looked around and didn’t see the resources, locally, for early-stage micro-enterprise small-business owners,” Kaylor says. So they started building a community of small-business owners to support and learn from one another. The three partners launched Passages to Success in 2022.
“Many of us start a business doing something we love,” says Kaylor, “and then we realize we don’t know how to do sales, or marketing, or bookkeeping. We’re scared to let people know that we don’t have it all figured out. Passages to Success is about trying to normalize conversations around fear and anxiety and loneliness and bring together people who understand these things so we can shrink the time between start up and success. That’s how we can build each other up in the community.”
The most common challenges to address now are hiring and inflation. “A lot of new and early-stage small business owners are afraid to raise their prices,” says Kaylor. Passages to Success helps its members deal with the challenges of running a business in real time, meeting its members where they are with group support, mentor support, and peer-to-peer support.
Group support comes from monthly “masterminding” sessions in various formats including roundtable discussions and “hot seats” where members discuss specific challenges for concrete recommendations. Mentor support is from five established business leaders who offer one-on-one guidance. And peer-to-peer support is in the form of an assigned group that helps each other stay on track toward their goals.
There are currently 35 members, most of whom are solo entrepreneurs and micro-enterprise business owners. They represent a broad range of industries including real estate, financial services, retail, and manufacturing.
One of their members is Kara Bowman, co-owner of CheckRight NW, a bookkeeping and payroll company. She started as co-owner Jon Dyer’s first employee, working part-time while holding down five other jobs to make ends meet. Her role became full-time within a year, and a few years ago, Dyer asked her to become a partner. “It wasn’t something I expected, to be in an ownership role, but I was excited for the chance,” she says.
The founders with Passages to Succeess member Kara Bowman of CheckRight NW
Working late one night, Bowman hopped on a Zoom call for a Passages to Success roundtable discussion. After listening to people talk about their own struggles, she realized that this community support was just what she needed—and that she had as much to offer as she had to learn.
“I joined Passages to Success to help me be a better business owner as I navigate this transition from employee to ownership,” she says. “I wanted a place where I felt comfortable and understood. There are other networking groups who can help grow the business, but I wanted someone to help me grow.”
Kaylor, Surratt, and Knopp agree that Bowman is a perfect example of one who gives as much as she receives. “Her helping other people shows how much she’s grown into that leadership role,” says Kaylor.
What Bowman likes best is that at the roundtable meetings, she hears real ideas, real people, and real situations. “You can connect only so much through a screen, but in person, you have that handshake, you have that energy. And Jonathan, Ben, and Jason—their energy is contagious.”
Passages to Success is built on personal interactions like this. “We’re humanists,” Kaylor explains. “A lot of other groups are talking about growing net worth, and it’s all about the money. But our focus is on who these people are and how they’re navigating the challenges of being small business owners. Growth and financial security are important, but sharing these experiences together—that’s critical to what we do.”
It’s also true to their casual roots. “Beer is one of our core values,” says Kaylor. “It’s a metaphor for having a good time. We always seek to create an environment that is fun while you’re doing the hard work. I think that’s why we’ve had the success we’ve had.”
Next year, the partners plan to restructure the program into different tiers to reach larger, more established organizations in addition to solo entrepreneurs, and to double their membership base. They’re partnering with other meetup groups to reach a broader mix of people, and they plan to continue hosting large conferences, which have recently included support from the corporate business community as speakers and sponsors including Comcast Business, Port of Vancouver, and ZoomInfo.
“When you bring together that diversity of experience, we think it’s going to be much more impactful for the group,” Kaylor says. “We’ll continue to be connectors so Vancouver has a very dynamic and successful small-business community.”
Brand stories are paid content articles that allow Oregon Business advertisers to share news about their organizations and engage with readers on business and public policy issues. The stories are produced in house by the Oregon Business marketing department. For more information, contact associate publisher Courtney Kutzman.