Main Street Mavericks Days Five & Six: Meeting Bend’s Small Businesses

It’s Main Street Mavericks days five and six in Bend, Oregon! We took a northern turn through cow country and some terrifying winding roads to land ourselves in Sisters on day five — then we picked up our CEO Amad to join us for a day of interviewing!

Come meet Bend’s merchants.

Main Street Mavericks Recap

To learn who the Main Street Mavericks are and what road trip we’re on, head on over to our Day One Main Street Mavericks Blog to find out all about us and our adventures around Oregon! We are on a mission to meet as many small businesses in Oregon as possible on a six-day road trip across Oregon. We’re coming to Bend from Day Four in Ashland, Day Three in Corvallis, and Day Two in Cannon Beach.

Day Five: Sisters

Breakfast

Hotel breakfast! It kept us on schedule, and it was free, which kept our Finance Director, Shelli, happy, too!

The Nest Design Studio

Emily Head, of The Nest Design Studio, always knew she wanted to work creatively in design, and after a tumultuous start (she and her husband lost their jobs in the aftermath of the housing crisis and went into different careers), she knew that it was time to take a leap of faith and follow her talents. She opened her design studio in downtown Sisters and provides upscale and personalized design work.

Read more in our spotlight on The Nest Design Studio.

Day Five Businesses We Patronized

We had a lot to catch Amad up on after we picked him up at the airport — our last four days on the road, the interviews we’d completed, and our post-production content plans. Since we allotted ourselves a buffer in the evening in case Amad’s flight was delayed, we didn’t have any interviews scheduled. So, we decided to do a little tour of Bend’s small businesses … mainly ones related to good food and beer.

• Crux
• Dinner at JIĀ
• Velvet Lounge

Stayed At

The Campfire Hotel is adorable and on-brand — my room’s walls were adorned with floor-to-ceiling pictures of Bend loggers from over 100 years ago, and the rustic theme was carried throughout.

Day Six: Bend

Breakfast

I took no notes of what we did for breakfast on day six. But I went on a hunt to find out. No RAMP reimbursements for breakfast … and no pictures of breakfast … and a very fuzzy memory of eating a packed granola bar. Look at us saving more money!

Tomi Mart

Bend’s first Asian market, Tomi Mart, opened in June of 2024 and is on a mission to supply Central Oregon with the Asian foods and accouterments they have been missing. With expensive shipping off the I-5 corridor, Tomi Mart is finding creative ways to source in-demand items. Stocked with snacks, treats, fresh produce, and a ramen wall, Tomi Mart doesn’t just want to be a grocery store but a key connective piece bringing together the Bend community.

Read more about Tomi Mart and meet Natasha Dempsey, one of the owners there.

Lunch

We had a tentative interview scheduled for the owner of The Lot, but we couldn’t make it work time-wise. So, we decided to check out the space for lunch anyway! I am completely obsessed over the Fricken Faco fish tacos — I’ve been dreaming of them since we left Bend.

Ida’s Cupcake Cafe

Next, we hopped on over to Ida’s Cupcake Cafe, owned by Autumn Lodge Persinger, who purchased the store from Ida herself when she retired. But Autumn has been able to put her own spin on the classics and find new ways to grow her cupcake empire.

Come meet Ida’s Cupcake Cafe to learn more.

Pegasus Books

After that, we ventured back downtown to meet with Duncan McGeary, who owns Pegasus Books. Duncan had so many incredible things to share about his bookstore and the ways he’s transformed his business since adding more book options in addition to his extensive comic book collection. He considers himself fairly old-school — eschewing contemporary marketing techniques, and he declined an on-camera interview, but please go check out his bookstore in downtown Bend.

Wool Town

We hopped on over to chat with Katie Ketchum of Wool Town — a speciality yarn store, also right in downtown.

Vector Volcano Classic Arcade

Our last scheduled interview of the entire trip was at Vector Volcano Classic Arcade where we got to meet former Pixar animator Brett Pulliam who opened this arcade as a lifelong retirement dream. When he moved from San Fransisco, Bend won the location award because it didn’t have a classic arcade and Brett wanted to corner the market. He brings his own collection in to rotate — most of which are popular pinball and arcade games from the 70s and 80s.

Learn more about Vector Volcano in our spotlight.

Dinner

Amad treated us to a fancy dinner at Dear Irene — way off our per diem, but the boss had it covered — as a celebratory dinner to commemorate a great trip. Kendall and I talked about the more than 30 businesses we talked to and made plans for future installments.

Stayed At

Spent our final night at the Campfire Hotel — we cannot tell you how much of a luxury it felt to be able to spend two nights in the same place.

Where Should We Go Next?

And that’s a wrap on Main Street Mavericks: Oregon Edition. We’ve reached the end. Kendall and I traveled over 800 miles, spoke to more than 30 small businesses, and brought home a bunch of great souvenirs from each business we stopped at. Merchant Maverick is dedicated to helping small businesses grow and make smart decisions when choosing business software, but to do our job effectively, we had to hear from real business owners who are out there daily, making their dreams work.

To each and every business we talked to: Thank you! Thank you for being generous with your time and your knowledge. We know that you have provided a wealth of advice for other small business owners. We appreciate you.

Be sure to follow us on YouTube to stay tuned for Merchant Maverick’s Main Street Mavericks Part Two.