The Pied Piper of Salem

Chip Conrad, pictured at his coworking space, Co.W.

A serial entrepreneur aims to make Salem a hotspot for nightlife and startups.

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When Chip Conrad moved to Salem in 2009, he joked he wanted to become a goat farmer.  

“Salem had this terrible stigma as boring and lame,” Conrad says. “No revitalization was happening.”

In the nine years since, Conrad, 42, has dedicated himself to enlivening Oregon’s capital city.

Today, Salem is still a sleepy town. But those who venture to the central core feel a pulse, then a throbbing heartbeat.

That life force emanates from Reed Opera House, a stately 1870s brick building in the center of downtown that houses more than 60 businesses. On the third floor, Conrad — California surfer dude, improv comic, serial entrepreneur — pumps new energy into his adopted home.  

IMG 0636The Reed Opera House, downtown Salem

On a recent Tuesday morning, sunlight streams into the Opera House, where Conrad presides over his coworking space, Co.W (pronounced “cow”). 

Dominated by a wall-length whiteboard, the airy main room alternately hosts animators, tech CEOs and the author of Adulting: How to Become a Grown-up in 468 Easy(ish) Steps, who reportedly pounds two whiskey shots before writing. The staff of a nonprofit, Fresh n’ Local Foods, crunch numbers in an adjoining office space. 

“This is a small town that I’d like to have a big town feel,” Conrad says. “If I could have a day with you, I could change anybody’s perception of Salem.” 

I pick up the gauntlet. Conrad and I leave Co.W and wind through the Opera House maze of storefronts and down to the second floor. Conrad launched his Salem career here with a comedy club in 2009. Others, including the owners of Gilgamesh Brewing, which opened the same year, credit the Opera House for kickstarting their businesses.

“The Reed Opera House is an amazing incubator,” Conrad says. “Businesses make it here, then move out.”  

We walk outside, onto Salem’s main drag, Court street, and pop into a few of the cafes — Archive Coffee, Bo & Vine, The Governor’s Cup Coffee Roasters — a coffee shop where Conrad and other young professionals worked in the pre-Co.W days. We run into three or four of his acquaintances. “Hey, Chip!” one of them calls out while sitting in traffic.

Chip Conrad has worked tirelessly on his personal business and continues to reinvent himself, constantly pushing this city forward” —Christopher Holland, Taproot Café Owner

Long-haired, with a flannel and jeans sartorial style, Conrad relishes pounding the pavement — literally. Every morning, the Florida native walks four miles to work, conducting business on his smartphone along the way. Last July, he ditched his computer altogether. 

A serial entrepreneur who has started and sold several businesses, Conrad oscillates between humble and grandiose. He views himself as a pioneer,  generating new ideas, new companies and new directions for the city. Yet he is eager to praise the accomplishments of others, and many in the city’s business and policy community return the favor.

Chip Conrad has worked tirelessly on his personal business and continues to reinvent himself, constantly pushing this city forward,” Christopher Holland, owner of the sustainable restaurant and juice bar Taproot Lounge & Café, said in an email. “Chip has been a constant inspiration and role model for small businesses.”

IMG 0639Chip Conrad

In 1997, plagued by dyslexia and attention deficit disorder, Conrad dropped out of Liberty University, the conservative Christian college in Lynchburg, Virginia.

He credits his first real-world startup opportunity to a religious crusade: A Florida megachurch needed him to turn a bar into a coffee shop. Conrad formed a Biblical improv comedy troupe to bring in customers. Soon he got offers to perform at weddings and events. 

Next a California venue came calling. They offered to fly him out and pay $100 for a performance. Before long his troupe, Isaac Improv, gained a global following performing sketches to promote Christian beliefs. (The group’s website proclaims, “We love God. We love your audience. We love Chick-Fil-A.”)

Conrad flew around the world doing some 250 shows a year.

He never looked back to Florida. “We came back to wash our clothes, and that was it,” he says. 

Ten years later, Conrad pulled off the road in another coastal city, San Diego. There, he met his wife and started UnlearnedInc., an entertainment booking and managing company. He employed 25 people and brought in $1 million in revenue. He ran the business from his phone while living on the beach. 

“I was an okay comedian,” he says. “But I was great at booking and managing comedians.” 

IMG 0634Conrad at the original location of Capitol City Theater in 2009. He eventually sold the club to a former employee, and it relocated to 210 Liberty St. 

Conrad first contemplated a move to Salem when his wife said wanted to be closer to family in Oregon. Maybe it would be relaxing, he thought, forsaking the fast-paced startup world for the pastoral life. 

So in 2009, Conrad dropped in from silicon- and- sun-drenched California. At the time, Salem was still recovering from the 2007 financial crash. The central core suffered from 75% blight. The streets emptied after 9 p.m. The city struggled to shake its boring reputation. 

But if it lacked vigor, Conrad thought, Salem showed promise. It was an hour from the coast and mountains. It had real estate downtown for restaurants and cafes. 

“Coming from California I didn’t get the stigma,” says Conrad, who is prone to spouting entrepreneurial aphorisms — “the money is in the clouds and the dirt,” and, “can you jump off a cliff without a parachute?”

“I said, ‘this place needs to be the center of it all.’ Who’s with me?” —Chip Conrad

So he put goat farming on hold.

“I said, ‘this place needs to be the center of it all. Who’s with me?’”

He opened Capitol City Theater, a comedy club. It was the second business, along with Venti’s Café, a downtown restaurant with a basement bar, to break the de facto 9 p.m. curfew. 

At first the project struggled to get off the ground. When performers asked the crowd to call out suggestions, no hands went up. “I never would have started a comedy club here if I knew what the culture was like,” Conrad said. “It was like a bunch of middle school kids worried about being cool.” 

“I was an okay comedian. But I was great at booking and managing comedians.” —Chip Conrad

But a year later, in 2010, everything changed. 

Clicking through a Mashable article, Conrad found a hip new company: Groupon. He became the second business in Salem to offer Groupons. He sold 1,000 tickets in 24 hours. 

The city wasn’t accustomed to this kind of boom. Officials required Conrad’s club to pay $420 for a health license, and offer five substantial meals, just to crack open beers.

Conrad didn’t want to stock any food. “We had $8 hot pockets,” he said. “Like, I dare you to buy a hot pocket.”

He eventually sold the comedy club to an employee. In 2012, Conrad founded the Center for Entrepreneurial Education and Development. The nonprofit trained budding Oregon entrepreneurs, young and old. 

One of its flagship endeavors was “Lemonade Day.” The franchised nationwide education program taught middle schoolers to get a loan, set up shop, and build a customer base — for a lemonade stand. The first year, 2,000 kids participated. 

Riding that success, Conrad sought out sponsors for a second year. He visited the offices of a “very influential gentleman” in Portland. But the ask failed, and Lemonade Day soured. “Why would we teach kids to run their own company,” the Portland business owner said, “when they can get a good job at Whole Foods?”

Conrad reflects on the failed effort. He’s since turned his attention to other ventures like Co.W. “I’m a capitalist but I’m also a liberal,” he says. “I think socialism is great. But if you want to start a company you should. Sometimes it’s the only skill people have.” 

“This is a small town that I’d like to have a big town feel,” Conrad says. “If I could have a day with you, I could change anybody’s perception of Salem.” —Chip Conrad

In 2013, he got another shot at kickstarting local startups. Acquaintances convinced him to produce a Salem-based “Shark Tank” style pitch event. 

They cut him a $2,000 check, and Conrad saw a chance to garner big outside investment in downtown. He would use a literal stage to promote Salem as a lively innovation hub. The project merged two of his passions: performance and entrepreneurship. 

He reserved a theater, marketed the event and bought some wine. Then he searched for investors who could spend $20,000 in one night. 

He settled on three angel investors: Lance Donnelly, Salem local and owner of Tan Republic; Michael Hill; and Rich Duncan, whom Conrad says “builds every McDonalds on the West Coast.” 

Whittling pitches from Salem entrepreneurs down to 10 contestants, he gave them one rule: “You have to start it in Salem.” 

They heeded the call. The event jumpstarted several Salem-based businesses, including a baby bib manufacturer and Lumen Light, which eventually sold its Smartphone-controlled Christmas lights to Sony. 

By the end of the event, Donnelly had promised to leverage his Tan Republic success to franchise Taproot, making it a household name across the West Coast. Holland, Taproot’s owner, “thought about it for a couple minutes,” Conrad says, “and said, ‘no.’” Instead Holland, who believed in Salem’s potential, funded the café through Kickstarter. 

Salem by the Numbers

Population: 165,599

Labor force size: 80,102

Median Household Income: $52,833

Unemployment rate: 5.3%

Largest employer: State of Oregon

Largest private employer: Salem Health

Businesses within a 20-mile radius: 15,665

Source: Business Oregon 2017 Labor Force Report, City of Salem Economic Data

Years ago, Holland and Conrad would have been called crazy for such devotion to Salem. 

The capitol had a reputation as a government town and food-processing hub, not a center of culture and entrepreneurship. People worked in Salem, but lived elsewhere. An hour from its far trendier northern neighbor, Portland, Salem struggled to retain young talent.

But the demographics are in Salem’s favor, and already, there are signs of change. Twelve downtown properties were sold in 2016. In one recent deal, an investment firm bought half a block for $1.77 million. 

With investment comes population and job growth. A  2015 study from ECONorthwest predicted Salem’s population will mushroom to almost 270,000 by 2035.

“Salem is projected to significantly outperform the rest of the state when it comes to future labor force growth, based on the demographics and our office’s population forecast.” wrote state economist Josh Lehner in a 2016 report. Salem is growing more jobs today than at any other time in the past 25 years. 

Nick Williams, CEO of the Salem area Chamber of Commerce, says the city is well positioned to capture a piece of the new economic pie. 

“Oregon’s economic fabric will shift more in the coming years as a rising minimum wage pushes out lower wage processing and manufacturing jobs,” Williams says. “We’re fortunate to be in a community where our public and private sectors have an eye on this ball.” 

Ten years ago, if you had said we’d have both a successful comedy club and coworking space—people would have said, ‘you’re crazy.’ But it’s happened, and Chip’s been the tip of that spear.” —Nick Williams, CEO, Salem Chamber of Commerce

This revival comes with growing pains. As population soars, housing prices and downtown traffic have increased. Salem home values rose 10.9% in the past year. Rush hour is a daily occurrence.

It’s all worth it, Conrad says. “Bring it on.” 

Salem is no Portland. But the city has a history of urban design foresight. Several generations of mayors worked to develop 11.2 acres of waterfront property into Salem’s Riverfront Park. 

In 2011, the city completed a strategic action plan calling for quality downtown rental housing, streetscape improvements and other projects. The city hopes these improvements will bring $136 million in investment and 6,100 jobs to the central core. 

More recent urban design initiatives, along with the new businesses, have further enhanced downtown livability. The Peter Courtney Minto Island Bridge and Trail opened this year, linking downtown Salem with more than 30 miles of trails and 1,300 acres of parks. 

As of about three years ago, Salem nightlife started to awaken. Restaurants and bars began to thrive.  The streets filled with revelers on weekend nights. Businesses stayed open later. 

“My promise to them was:  The people are here, you just have to stay open,” Conrad says. “They’re a sleeping demographic. They’re going to Portland to get this.” 

“Five years ago we were a blank canvas. There’s still a lot more painting to go, but it’s on its way.” —Chip Conrad

Soon, Conrad hopes, that demographic — young creatives — will stay put. The Rose City is a millennial magnet, but Salem is attracting many of the same amenities young professionals crave. 

“Portland’s thriving, but I don’t have any interest in it,” Conrad said. “My interest is in Salem. Five years ago we were a blank canvas. There’s still a lot more painting to go, but it’s on its way.”

Coworking spaces, swanky coffee shops, and maker spaces in alleys are evidence of the dramatic changes underway in Salem, says Williams. “The number of creatives we have flooding into the city,” he says, “are giving us a texture I haven’t seen in my nearly 20 years here.”

Conrad is the operative example. “He’s led by taking risks and succeeding,” Williams says. “Ten years ago, if you had said we’d have both a successful comedy club and coworking space — people would have said, ‘you’re crazy.’ But it’s happened, and Chip’s been the tip of that spear.”

In 2016, Conrad stumbled into the mayoral race as a contender. A fan had posted a blog comment saying Conrad should make a bid. Hoping to quash the idea, Conrad posted the comment on his Facebook wall. It had the opposite effect: He says he received some 4,000 votes, out of a total of 34,671. (Salem’s current mayor, Chuck Bennett, confirmed Conrad’s tally, although according to the Marion County Clerk’s office, there were only 1,500 total write-ins.) 

IMG 0633Co.W, Conrad’s coworking space in the Reed Opera House

That’s how he landed in the orbit of Mayor Chuck Bennett, whom he describes as a “crazy little Papa Smurf-looking dude who’s awesome at pushing things through.”

Bennett appointed Conrad to the Downtown Advisory Board, and the duo began discussing city policy. “I regularly talk with him about downtown and many other issues  aimed at making [downtown] more vibrant and interesting,” Bennett said in an email. “He has been a great advocate in these areas.” 

Likewise, Conrad sees Bennett as refreshingly progressive compared to past Salem leaders. “I think our previous mayors wanted to keep Salem kind of sleepy,” Conrad says. “You used to be able to know everybody, and you could get everywhere in five minutes. It was a good old boys club.”

Conrad wanted no part of that. Having lured local businesses, Conrad set his sights on Uber and other tech gamechangers redefining American cities.  Rejected by Uber, Bennett and Conrad phoned Lyft instead. 

“They told us, ‘our lobbyist lives in Portland. We’ll send him down every day. Whatever you need him to do.’” Conrad says. 

Conrad and Mayor Chuck Bennett talk ridesharing and other city policies on Conrad’s video blog

Salem’s chief of police supported an ordinance that required city background checks on rideshare drivers. Bennett was against it. He shared his rideshare opinions on Conrad’s video blog. 

That cleared the road for Lyft. The company threw itself a housewarming party in a Salem alleyway. Conrad and Bennett took the ceremonial first ride. 

Other sharing economy companies are  showing interest in Salem. Instacart, a grocery delivery service, and UberEATS launched here in November. Next fall Amazon plans to open a Salem fulfillment center,  which will employ 1,000. 

IMG 0630Conrad in Co.W, his coworking space

The resources and inspiration Conrad provided local entrepreneurs continues to invigorate him. He enjoys Salem’s progressive vibe and  outdoor lifestyle — surfing on the weekends in particular. 

But he has poured much of his personal time and energy into Salem, and there are signs he is getting restless. “Everything kind of rose around me and I didn’t realize how much I was not sleeping, not eating, isolating myself,” he says. “What can I do next? Who can I talk to?” 


In Venti’s, I ask Conrad when he’ll be satisfied with Salem’s evolution. He pauses for a full minute, gazing out the window toward the Opera House. He envisions a bustling airport, high tech industries and a second state university campus to attract and retain young talent.  He is championing paid parking, and wants to remove historic preservation ordinances that shield unsightly buildings from development. 

“Salem breaking a population of a million would be a big one for me,” he says finally. “That brings culture, events, companies, jobs, quality of life, social circles where you can find your niche. People won’t be left alone. That’s when I think I’ll be happy here.” 

Then perhaps Conrad will retire where everybody does, back where it all started, in Florida.