Jessie Duley
Founder of Burn Cycle, which currently operates five experiential fitness studios.

"There is so much collaboration and encouragement from the entrepreneurial community. If you ask for something, people will help you. Coming from L.A., people would cut off their left arm before they would do that."

"I don't think I could have done it in any other city that wasn't open to making eye contact, for lack of a better context. Portlanders see each other."

Yesenia Gallardo
Co-founder of PODA foods, a startup that raised crickets and processed them into protein powder. She started the company in 2015 but dissolved it in 2017.

"One of the reasons we decided to launch our company here was because this was a good market for early adopters in protein. That was definitely one of the things that was positive about Portland. The community is very willing to try new things."

"Also, there are a lot of resources in terms of accelerators, like the Portland Incubator Experiment, that provide a lot of support to startups. And we received support from Prosper Portland to be part of their startup challenge. If we hadn't received that, we wouldn't have stayed, because those were really critical resources at a very critical time."

"One of the reasons we came to Portland was that we thought there would be better access to low-cost real estate. We timed things exceptionally bad in that area. Not only because of the growth boom in Portland, but also because of the cannabis regulatory changes that made warehouse spaces much more expensive than we ever anticipated."

Luke Kanies
Founder of Puppet and, more recently, Clickety. (Note: Puppet was founded in Nashville in 2005 and moved here in 2009.)

Luke Kanies
Luke Kanies

"I have a love/hate relationship with Portland. I think we're particularly well-suited for companies coming up in food and beverage, and probably apparel. I'm less convinced we're a good fit for pure software companies. The leadership bench is not very deep, and we're so close to the Bay and Seattle that people will gravitate there rather than here."

"Portland will stay good for bootstrappers as long as housing is cheap enough."

"I did face challenges when it came to recruiting people—Oregon having one of the worst public education systems in the country. That starts to have an impact when people do their research and figure that out. Then, obviously, anybody who's not white, when you learn about Oregon's history as a white utopia, that affected my ability to recruit people too. But those aren't things we can change in a moment."

Steve Marsh
Founder of Smarsh, a digital archiving company that he started in 2001 and moved to Portland in 2004. Marsh resigned from the company last year and now invests in other startups.

"In 2004, we moved the Smarsh headquarters from San Francisco to Portland. With no outside investment at the time, Portland labor and office space were more affordable. In general, we could stretch our limited resources further. In those days, we had a difficult time finding talent for highly technical and executive level positions. Even finding experienced sales people could be challenging at times. So, we'd search for a long time locally and try to convince candidates from other cities to relocate to Portland. Many were reluctant to pack up and move to a city that potentially had no backup job for them or a position for their spouse or significant other. While the quality of life here was attractive, it was hard to recruit people. That has changed. What hasn't is Portland has a very collaborative culture among founders, executives and investors. Everyone seems to want to help the greater Oregon business community to thrive. I also think it's now relatively easy to find capital if you have a decent business concept and/or team."

Kanth Gopalpur
Founder of Monsoon Works, an e-commerce site he sold in 2010. most recently, he co-founded Public Market, a blockchain e-commerce site that has suspended business operations. Gopalpur is currently chair of Business Oregon, the state's economic development agency, and an angel investor.

Kanth Gopalpur
Kanth Gopalpur

"We've got a great startup culture here. Funding is not as easy as Seattle, or another area, but it's got a lot of perks. We do have workforce issues: One, we don't have a big enough pool. It's a function of the population. It's a function of a lack of big universities. That's one issue. The other issue, too, [is whether] there are enough people with the right skill set. When you have a bigger pool to draw from, you get people with the right skill set as well."

"When I talk about entrepreneurs, most people just talk about it as it pertains to the tech sector, but there's more than that. It's apparel, it's food. I like to think of [Oregon] as a state of small businesses."

"We don't have any unique advantages, in my opinion, in tech. Now if it was in apparel, I think we have some unique advantages here. So if it was in beer, right? If I was brewing beer and wine. But software? Not really."

Tyrone Poole
Founder of OneApp, a technology company that helps renters navigate the application process.

Tyrone Poole
Tyrone Poole

"One of the benefits of starting a biz in Portland is that a lot of people get excited here and are willing to help and invest time into helping you get a good, great idea off the ground. It's just a place where a lot of people are looking to jump on cool, exciting projects. So you go up to somebody and you're like, 'Will you mentor me? But if you show up and you know, you're, you're black, you got some dreadlocks—you don't remind this person of anything of themself. It's harder to get mentorship"

Pat Scruggs
Longtime consultant to the startup industry and Director of Innovation and Technology under Gov. Ted Kulongoski.

"A challenge in the Portland area is that larger businesses don't seem to be as engaged in the giveback and the nurturing of startups," Scruggs said. "In Columbus, Ohio, the larger companies are very active in helping startups, or seed funds. It's something I've not seen in decades in the Portland area, which is the engagement of the larger companies. Those companies can be first customers, they can be great mentors, they could be a variety of things."

"Our biggest issue, however, is talent. The hardest thing about getting funding is, you'd have to have a really strong management team that's been there, done that. But once a startup is launched and you need to grow the company, who else is on your management team, and who else is going to help you grow that company? The one thing I can say that I really think that the Portland area lacks is experienced growth-stage management teams."

Patrick Triato
CEO of Goodwell Co., winner of PitchfestNW 2019.

(Wesley LaPointe)
(Wesley LaPointe)

"Portland is a port city, which really comes in handy when you are dealing with global distribution channels and international opportunities. It is, however, expensive from a tax perspective to have a small business here, as well as the cost of an ever-changing living wage, which we are happy to provide, but it does put additional stress on our business and growth."

Raven Zachary
Founder of mobile app company Small Society (sold in 2012). Now founder of  Object Theory, an augmented Reality company.

Raven Zachary (Sam Gehrke)
Raven Zachary (Sam Gehrke)

"I was living in Dallas, Texas, and I moved the family to Portland in 2006 because I fell in love with the city and because of its open source technology community here. There are some characteristics about Portland that are really positive. There's a really strong independent technology talent pool in Portland. But Portland doesn't really have those large anchor technology companies. Even Intel: You know Hillsboro isn't really part of Portland, and everyone talks about it. I've run technology events, meetups of all sorts of shapes and sizes, and the Intel community doesn't really participate. One would hope that, you know, companies like Intel, or even Nike, be much more participatory in the Portland community."

Monica Enand
CEO and co-founder of Zapproved, which makes legal software.

Monica Enand
Monica Enand

"The greatest strength of our community is how connected and supportive it is. When we were starting out, we leaned on others for advice, and they would make time to meet or introduce us to a helpful resource. The main area that is holding us back is the lack of a deep bench of experienced executive talent. We just don't have enough people here who have 'been there, done that.' It takes time and repeated successes to build that group who can get startups there faster with a higher chance of success."

Sce Pike
CEO of IOTAS Inc. moved to Portland as part of a merger between her former company, QMS, and a Northwest-based company, Citizen.

Sce Pike
Sce Pike

"The more I visited Portland, back in 2009, the more I grew to love it and felt this vibe that reminded me of the '90s in Silicon Valley, a sense of camaraderie mixed with youthful enthusiasm for the startup ecosystem. I also saw something different in Portland from the Silicon Valley startup ecosystem, something uniquely Portland, which I would describe as the 'balanced' startup community where people practiced life-work balance, prized ethics above money, and are mission-driven above all else. We're just now seeing a few of the early startups that exited create enough wealth to invest back into the startup ecosystem. When we see more regular exits…then we will see the startup cycle be able to feed itself versus looking for outside investments. I think we're getting there."