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Written by Lucas Alberg

Why Bend is a Dream Town for Adventurous Entrepreneurs

Rob Little

Editors Note: This article was originally published September 2021

Rob Little knew the power of the outdoors. He spent his youth hiking and camping in the mountains surrounding the Southern Oregon town of Medford where he grew up. His passion for outdoor recreation never waned and while studying creative retail strategies during his MBA program at the Wharton School of Business at the University of Pennsylvania, Little and classmate Jared Peterson formed the seeds of what would later become Cairn—a subscription box service for outdoor gearheads, delivering curated products for camping, backpacking, hiking and other outdoor-related activities. Little and Peterson saw the success of companies doing similar concepts across the clothing, pet and food industries and modeled this same approach to the outdoors, which had not yet been done.


Founded: 2014

A monthly and quarterly subscription box service for outdoor recreation consumers, delivering curated products for camping, backpacking, hiking and more.

Owners: Co-CEOs Rob Little and Jared Peterson

Fun fact: Since its founding, Cairn has partnered with over 300 outdoor brands to ship 3 million products to more than 75,000 outdoor enthusiasts around the U.S. Cairn was acquired by Outside in April 2021 and continues to be run by Little and Peterson in Bend.

Though Cairn was not much more than an idea at the time, when Little finished his MBA in 2013, he and his wife Betsey took the plunge and moved to Bend with the idea that a successful business and personal passions were not mutually exclusive. 

“Bend checked all the buckets,” Little said. “The outdoors, the people and the spirit of the city were exactly what we wanted. At that point, it was the mechanics of quitting our jobs, packing up everything we owned in our car and making the trip.” 

Like Little, most residents in Bend come to the area for one shared goal: to be surrounded by—and enjoy the fruits of—the outdoors. It’s no surprise this mentality blends into the business community as well. According to Brian Vierra, outgoing venture catalyst at Economic Development for Central Oregon, many entrepreneurs move to the area first, and then once settle, begin to establish roots in the business community. “People move here to take advantage of a lifestyle,” he said. “But once they’re here, they’re committed to an area, and they start to build relationships. If you’re entrepreneurial, eventually you start a business here, whether you originally worked in the [Central Oregon] area or not.”

It’s this combination of entrepreneurial and adventurous mindset that makes Bend unique. It’s also these factors—along with an amazing mentorship network—that makes Bend great for startups and early-stage companies.

Mentors and Talent All Around

Economic Development of Central Oregon
Brian Vierra

Economic Development of Central Oregon

Founded: 1981 

Helps with the economic development of Central Oregon through three key areas: Move (recruitment of companies to Bend); Start (startups); and Grow (helping with retention and growth through incentives and other means).

CEO: Roger Lee

Fun fact: In addition to putting on the Bend Venture Conference, EDCO also offers mentoring resources through its Stable of Experts program.

Bend Venture Conference
Van Shoessler

Bend Venture Conference

Founded: 2003

A multi-day conference put on by EDCO that brings together entrepreneurs and business owners to pitch innovative ideas in front of peers, angel investors and the Bend community. 

How it works: Entrepreneurs and business owners across three categories—Growth Stage, Impact and Early Stage—compete to become a category finalist and earn the right to pitch their business idea for a chance to win financial rewards and services.  

How to enter: Prospective applicants submitted through the BVC website in August 2021. October 21 to 22, 2021, Tower Theatre, Downtown Bend | bendvc.com

“Bend is the perfect place to begin or domicile a startup,” said EDCO’s Vierra. “It’s not as noisy as the Bay Area, not as much activity or competition.” But the biggest advantage, according to Vierra, is the small-town ability to make big time connections.

Van Shoessler, former VP of sales at insulated drinkware maker Stanley PMI, came to the area in the second half of his career and began to connect with like-minded outdoor industry veterans such as Gary Bracelin, who helped pioneer the snowboard sports category in the 1990s. With help from EDCO, the pair formed the Oregon Outdoor Alliance, with a goal to bring together outdoor industry employees to create vibrant communities. “We wanted to create the infrastructure here first, then attract the businesses and people,” Shoessler said. Eventually, bridges were built and pavement was laid to begin connecting existing outdoor industry employees together and new ones in. Now, the ease of connecting for this sector in this community is amazing, he said. “You have a beer with someone and the next thing you know you have six names,” Shoessler said. “If you come here as an entrepreneur and realize your gaps, you can find someone to help you fill those.” 

Jesse Thomas, co-founder of Picky Bars, which was recently acquired by Laird Superfood, knows this firsthand. Thomas, his wife and co-founder Lauren Fleishman, and the team’s third co-founder Steph Bruce—three active professional athletes—moved the energy bar company to Bend from Eugene just three years into its short lifespan. Thomas sought to connect in the community quickly after moving to Bend. He joined Opportunity Knocks, an organization that matches like-minded business owners, CEOs, community leaders and key employees with a trusted team of peers who act as an informal board of advisors. Looking back, Thomas said that he feels fortunate to have landed in the group he did. “The people that played a part in Picky Bars’ growth were people from my Opportunity Knocks group who built successful businesses here,” Thomas said. “People like Scott Allan from Hydro Flask, Will Blount from Ruffwear, Meg and Dave Chun from Kialoa and Eric Meade—they were sounding boards for me early on. I was really lucky to be in that group and spend time with them.”

Opportunity Knocks
Gary Bracelin

Opportunity Knocks

Founded: 1996

Bend-based 501(c)6 nonprofit that brings together like-minded business owners, CEOs, community leaders and key employees with a trusted team of peers to act as an informal board of advisors to help achieve business goals. 

How to get involved: Apply through the OK website: opp-knocks.org/membership-interview

OOA Co-Founder Gary Bracelin, who also launched an outdoor incubator called Bend Outdoor Worx, calls Bend a “one-and-a-half-degree of separation” town. “We have an incredible amount of talent and resources here,” he said. “Whether through OOA, EDCO, Opportunity Knocks, BOW—the support and infrastructure are there to bring the talent together. That’s the difference.” 

Brian Vierra from EDCO said many of these key individuals are newly retired or winding down their career and looking for something to do in addition to recreation. “They tend to make themselves accessible and help people who ask,” he said. “There are no companies big enough to support them and so they help in other ways, which is often helping startups.” 

Cairn’s Rob Little took full advantage of those willing to listen and give advice, gleaning knowledge from the vast outdoor industry experience available. “I took every meeting I could get,” he said. “If they’d talk with me, I shared everything and listened to what they had to say.” After Little prodded Gary Bracelin, he eventually landed Cairn in the inaugural class of BOW. “I wanted them all around the table to vet these things I was going through,” he said. The mentorship through BOW helped establish a firmer direction for the business and fill in the gaps for areas such as finance and accounting, among others. 

Outside of the outdoor industry, the willingness to help can be hit or miss. According to Hunter Neubauer and Kevin Hogan, founders of cannabis producer and retailer Oregrown, the cannabis industry is about as cutthroat is it gets, though mostly due to law. “There’s not a lot of collaborative efforts in town,” Hogan said. “Nearly every other market nationwide is less competitive due to regulation. We’ve got the least barriers for entry, which creates more competition.” 

Neubauer said he hopes one day this will change but for the moment, cannabis businesses need to look outside of their own industry for help. With a retail business, Neubauer and Hogan have worked closely with the Bend Chamber of Commerce, who the pair said has been very supportive. “In all honesty, I was shocked in the beginning,” Neubauer said. “They were extremely helpful to us and have been a huge advocate from the start.” 

The positive impression eventually led Neubauer to join the Chamber board, on which he still serves. To his knowledge, the Bend Chamber of Commerce was the first in the country to have a cannabis business owner on the board.

Picky Bars
Lauren Fleishman, Jesse Thomas, and Steph Bruce

Picky Bars

Founded: 2010

Real food energy bars and oats designed for athletes in mind, helping to fuel adventures with organic ingredients, plant-based protein and intentionally balanced nutrients and flavors. All products are gluten-free, dairy-free and soy-free while some are vegan.

Owners: Former professional athletes Lauren Fleishman, Jesse Thomas and Steph Bruce. 

Fun fact: Picky Bars was sold in April 2021 to Sisters-based Laird Superfood for $12 million. Laird Superfood saw a 98 percent sales increase of their primary business in 2020, reaching $26 million.

Though Bend is rich with mentorship and business support, it’s not without its flaws and challenges. Geographic isolation makes it challenging for travel, both for employees and more importantly, for production. “It’s an extra leg anywhere you go when traveling, which makes it so much tougher,” said EDCO’s Vierra. 

Cairn Co-Founder Jared Peterson said the company was forced to push their distribution out of Bend once they reached a certain threshold. “Distribution was by far the biggest challenge for us here, and probably something that can never get solved simply because Bend is so isolated.” 

Thomas and Picky Bars still manufacture and ship from Bend,albeit at a cost. “We’ve always done our fulfillment from Bend,but it’s been a challenge,” he said. “It delays shipping both to us and our customers and it costs more. It’s more time and more money.” 

A more recent challenge for companies has been housing and the impact on employee acquisition. Thomas believes that it could be one of the primary limiting factors in the economic growth of Bend in the foreseeable future. “People are getting priced out of homes, and it’s getting harder for companies to attract these employees,” he said.  

In addition to the affordable housing shortage, general increased cost of living and the small market has negatively impacted employee acquisition as well. Cairn’s Peterson said the fear of “If it doesn’t work out with you guys, what else is there?” is something that looms in the back of many potential candidates’ minds. But for those that do work out, it’s a dream combination for everyone involved. 

Kevin Hogan and Hunter Neubauer


Founded: 2015

A farm-to-table cannabis company headquartered in Bend offering consumers 21-years of age or older recreational and medicinal cannabis products. 

Owners: Hunter Neubauer, co-founder and chairman of the board; Kevin Hogan, co-founder and president

Fun fact: With a flagship store in Bend, the company has expanded to open new stores in Portland and Cannon Beach, with a Eugene location slated to open later in 2021. 

The slower pace of life and welcoming environment driven by the Bend lifestyle also bleeds into the investment circles of Central Oregon. Though by no means as affluent as larger markets such as Portland, Seattle or the Bay Area, there is money in Bend for those with a good idea and the willingness to work for it. 

Cairn’s Peterson quit what he called his “dream job” at Apple for a chance to grow a successful business of his own. Peterson moonlighted for several years with Cairn before fully committing and leaving Apple to move to Bend in 2015. Though Peterson said moving to Bend was one of the toughest decisions he’d ever made, it was a risk worth taking. “The idea of living in Bend and building our own brand was appealing,” he said. “There was momentum and it was exciting.” 

His previous experience in the heart of the tech industry gave him insight into how the traditional venture capital model worked. “Silicon Valley is go big or go home,” he said. “There’s a standard VC model, and it’s much more cutthroat. Here it’s more grassroots. You tap into angel investors who are a little more patient, and they help your business grow.” Peterson noted that nearly all the individuals who invested in Cairn were either from the area or connected to someone in the Bend community.

The Bend Venture Conference, which kicks off October 21, is a primary driver of funding for the region. The multi-day conference attracts angel investors to hear entrepreneurs and business owners from around the country pitch their innovative ideas in front of their peers and community. The competition is broken out into three categories—Growth Stage, Impact and Early Stage—with three to five finalist companies selected in each category. According to EDCO’s Vierra, the conference is the largest angel conference in the West and is now in its eighteenth year. “Over the past six years, the conference has invested over $11 million in thirty-eight companies,” said Vierra, who’s quick to add that this number doesn’t include the investments that happen outside the conference but were initially started or connected within the conference itself. 

Broken Top Candles
Affton Coffelt

Rob Little attended BVC prior to moving and said the spirit of the conference helped push him over the edge to relocate. The small-town setup is known for its energy and Little felt the buzz. Just over a year later, he was pitching the idea of Cairn on the stage and even walked away with a $15,000 Fire Starter Award, which is given to one of the conference’s concept or launch stage finalists. 

“BVC gave us a lot of energy,” said Little, who also competed the following year. “I equate it to playing a sport in a big event—there’s a big audience, you want to do well, you want to hear a response. It’s inspirational.” 

Broken Top Candles CEO and Founder Affton Coffelt pitched at BVC on two occasions and said each taught her something new about her business. “When I pitched the early stage, it allowed me to fully connect with the community and learn the resources available for entrepreneurs and startups,” she said. The second time, when pitching for the growth category, pushed her to look at her business in ways she hadn’t before. “It forced me to an uncomfortable place that really benefitted me in the long run. In the end, it gave me the confidence and courage to dive further and learn things both about myself and my business.”

Coffelt went deep in the rounds both years at BVC, and although she didn’t walk away with any awards, she said what came out of the experience was substantial for the business. “It was a flipping point,” she said. “I knew where we wanted to be, but when outside people start to acknowledge what you have, it gives your business validity.”

Little echoed these sentiments, saying BVC led to alignment with the community. “Our primary motivation was not being on the stage but trying to connect to the town. We wanted the community to embrace Cairn and have pride for us,” he said.

Broken Top Candles

Founded: 2015

Home and personal care products such as candles, linen sprays, lotions, soaps, sanitizers, diffusers and perfumes.

Owner: Affton Coffelt, founder and CEO

Fun fact: Currently in more than 2,500 retail locations around the country and employs twenty-three Bendites. The company is also a 1% for the Planet member company. 

Broken Top Candles’ Coffelt said that getting people behind you that understand your business is key. Coffelt said she has worked with or been involved in nearly every group Bend has to offer, from EDCO and pitching on the BVC stage to Opportunity Knocks, the Chamber and even state and national groups such as Business Oregon and Vistage. Each can serve a purpose depending on what you’re looking for and the stage you are in, she said. “Know your resources and stay connected,” Coffelt advised. “Even if you try something and it doesn’t work out, know there are other groups and people. Everybody in this community wants you to succeed.” 

Jesse Thomas commented that even direct competitors can be willing to lend a hand. Andy Hannagan, the owner of energy ball company Bounce Bars, was one of the first people he met in Bend. “He had this big brand in Australia and was growing it in the U.S. He was so helpful and supportive,” Thomas said. “Even after the acquisition, he reached out and congratulated me.”

EDCO’s Viera said the business community has a “rising tide floats all boats” mentality. “You’ll see competitors helping each other out because they all want to see the community of Bend succeed,” he said.

Looking back now, Little said BVC, the mentorship and the abundant resources available through the Bend business community proved pivotal for the trajectory of Cairn. “If I had one piece of advice for budding entrepreneurs in Bend, it would be to go all in,” he said. “Commit and be vulnerable. Stealth mode in business is not constructive. So much of success is feedback.”

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