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In the shadow of Amazon and Microsoft, Seattle startups are having a moment
Venture capital investment exploded across a number of geographies in 2019 despite the constant threat of an economic downturn.
San Francisco, of course, remains the startup epicenter of the world, shutting out all other geographies when it comes to capital invested. Still, other regions continue to grow, raking in more capital this year than ever.
In Utah, a new hotbed for startups, companies like Weave, Divvy and MX Technology raised a collective $370 million from private market investors. In the Northeast, New York City experienced record-breaking deal volume with median deal sizes climbing steadily. Boston is closing out the decade with at least 10 deals larger than $100 million announced this year alone. And in the lovely Pacific Northwest, home to tech heavyweights Amazon and Microsoft, Seattle is experiencing an uptick in VC interest in what could be a sign the town is finally reaching its full potential.
Seattle startups raised a total of $3.5 billion in VC funding across roughly 375 deals this year, according to data collected by PitchBook. That’s up from $3 billion in 2018 across 346 deals and a meager $1.7 billion in 2017 across 348 deals. Much of Seattle’s recent growth can be attributed to a few fast-growing businesses.
Convoy, the digital freight network that connects truckers with shippers, closed a $400 million round last month bringing its valuation to $2.75 billion. The deal was remarkable for a number of reasons. Firstly, it was the largest venture round for a Seattle-based company in a decade, PitchBook claims. And it pushed Convoy to the top of the list of the most valuable companies in the city, surpassing OfferUp, which raised a sizable Series D in 2018 at a $1.4 billion valuation.
Convoy has managed to attract a slew of high-profile investors, including Amazon’s Jeff Bezos, Salesforce CEO Marc Benioff and even U2’s Bono and the Edge. Since it was founded in 2015, the business has raised a total of more than $668 million.
Remitly, another Seattle-headquartered business, has helped bolster Seattle’s startup ecosystem. The fintech company focused on international money transfer raised a $135 million Series E led by Generation Investment Management, and $85 million in debt from Barclays, Bridge Bank, Goldman Sachs and Silicon Valley Bank earlier this year. Owl Rock Capital, Princeville Global, Prudential Financial, Schroder & Co Bank AG and Top Tier Capital Partners, and previous investors DN Capital, Naspers’ PayU and Stripes Group also participated in the equity round, which valued Remitly at nearly $1 billion.
Up-and-coming startups, including co-working space provider The Riveter, real estate business Modus and same-day delivery service Dolly, have recently attracted investment too.
A number of other factors have contributed to Seattle’s long-awaited rise in venture activity. Top-performing companies like Stripe, Airbnb and Dropbox have established engineering offices in Seattle, as has Uber, Twitter, Facebook, Disney and many others. This, of course, has attracted copious engineers, a key ingredient to building a successful tech hub. Plus, the pipeline of engineers provided by the nearby University of Washington (shout-out to my alma mater) means there’s no shortage of brainiacs.
There’s long been plenty of smart people in Seattle, mostly working at Microsoft and Amazon, however. The issue has been a shortage of entrepreneurs, or those willing to exit a well-paying gig in favor of a risky venture. Fortunately for Seattle venture capitalists, new efforts have been made to entice corporate workers to the startup universe. Pioneer Square Labs, which I profiled earlier this year, is a prime example of this movement. On a mission to champion Seattle’s unique entrepreneurial DNA, Pioneer Square Labs cropped up in 2015 to create, launch and fund technology companies headquartered in the Pacific Northwest.
Boundless CEO Xiao Wang at TechCrunch Disrupt 2017
Operating under the startup studio model, PSL’s team of former founders and venture capitalists, including Rover and Mighty AI founder Greg Gottesman, collaborate to craft and incubate startup ideas, then recruit a founding CEO from their network of entrepreneurs to lead the business. Seattle is home to two of the most valuable businesses in the world, but it has not created as many founders as anticipated. PSL hopes that by removing some of the risk, it can encourage prospective founders, like Boundless CEO Xiao Wang, a former senior product manager at Amazon, to build.
“The studio model lends itself really well to people who are 99% there, thinking ‘damn, I want to start a company,’ ” PSL co-founder Ben Gilbert said in March. “These are people that are incredible entrepreneurs but if not for the studio as a catalyst, they may not have [left].”
Boundless is one of several successful PSL spin-outs. The business, which helps families navigate the convoluted green card process, raised a $7.8 million Series A led by Foundry Group earlier this year, with participation from existing investors Trilogy Equity Partners, PSL, Two Sigma Ventures and Founders’ Co-Op.
Years-old institutional funds like Seattle’s Madrona Venture Group have done their part to bolster the Seattle startup community too. Madrona raised a $100 million Acceleration Fund earlier this year, and although it plans to look beyond its backyard for its newest deals, the firm continues to be one of the largest supporters of Pacific Northwest upstarts. Founded in 1995, Madrona’s portfolio includes Amazon, Mighty AI, UiPath, Branch and more.
Voyager Capital, another Seattle-based VC, also raised another $100 million this year to invest in the PNW. Maveron, a venture capital fund co-founded by Starbucks mastermind Howard Schultz, closed on another $180 million to invest in early-stage consumer startups in May. And new efforts like Flying Fish Partners have been busy deploying capital to promising local companies.
There’s a lot more to say about all this. Like the growing role of deep-pocketed angel investors in Seattle have in expanding the startup ecosystem, or the non-local investors, like Silicon Valley’s best, who’ve funneled cash into Seattle’s talent. In short, Seattle deal activity is finally climbing thanks to top talent, new accelerator models and several refueled venture funds. Now we wait to see how the Seattle startup community leverages this growth period and what startups emerge on top.
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Pioneer Square Labs is invigorating Seattle’s startup ecosystem
Three miles from Seattle’s South Lake Union neighborhood — better known as Amazonia to locals — sits Pioneer Square. The original heart of the city, the area has managed to hold on to its decades-old charm as other parts of town are besieged by Amazon-contracted architects.
On a mission to champion Seattle’s unique entrepreneurial DNA, startup studio Pioneer Square Labs has not only adopted the neighborhood’s moniker but established its fast-growing HQ at its center.
Pioneer Square Labs, or PSL, cropped up in 2015 to create, launch and fund technology companies headquartered in the Pacific Northwest. Operating under the startup studio model, PSL’s team of former founders and venture capitalists, including Rover and Mighty AI founder Greg Gottesman, collaborate to craft and incubate startup ideas, then recruit a founding CEO from their network of entrepreneurs to lead the business. The team uses an innovative method of rapidly ideating, testing and, if necessary, scrapping ideas, dubbed its “validation engine.”
The model differs from an accelerator or incubator. Y Combinator, for example, admits existing business into its months-long program, deploying its expertise and capital to bolster early-stage startups. PSL, on the other hand, creates startups and provides would-be founders with a derisked platform for company building.
“It’s a dream job,” PSL co-founder Greg Gottesman told TechCrunch. “If someone would say to you ‘hey, you can come into work every day, think about all the problems that are interesting to solve, all the tech that’s available and you have the resources to build companies,’ that’s just a dream come true … It’s just been a very fun ride.”
Xiao Wang, the CEO of Pioneer Square Labs spin-out Boundless, pitching at TechCrunch Disrupt SF 2017
The startup studio model is working for PSL. To date, it has raised $27.5 million in equity funding to build out its platform, in addition to an $80 million fundraise for its debut venture fund, which invests in PSL companies and other Pacific Northwest businesses. Of the 13 companies to emerge from PSL in the last three years, all have raised follow-on rounds from venture capital firms at an aggregate valuation of $200 million. According to PitchBook, PSL companies comprised 14.3 percent of all early-stage VC deals in Washington state in 2018.
Among PSL’s portfolio companies are cloud security compliance platform Shujinko, which closed a $2.8 million seed round from Unusual Ventures, Defy Ventures, Vulcan Capital and more last year. Plus, Boundless, a platform that facilitates the process of applying for immigrant status in the U.S., and Tally, a sports-prediction app spearheaded by football star Russell Wilson. Other recent spin-outs include Remarkably, a marketing and analytics software provider, and Attunely, a debt-collection-tech platform.
Meet the team
Pioneer Square Labs’ growing team of former operators, VCs, data scientists, engineers and more
Greg Gottesman, a former managing director at Seattle VC fund Madrona Venture Group, and the founder of its startup studio Madrona Venture Labs, leads PSL alongside a team of seasoned Pacific Northwest investors and entrepreneurs.
Rounding out PSL’s team of managing directors is Julie Sandler, a former investor at Madrona; Geoff Entress, a former venture partner with Voyager Capital and Madrona; Mike Galgon, the founder of the Microsoft-acquired digital agency aQuantive; and T.A. McCann, a serial entrepreneur behind Google-acquired Senosis and BlackBerry-acquired Gist. Ben Gilbert, who runs product at PSL, is another Madrona alum.
After nearly two decades investing in early-stage startups at Madrona, Gottesman made a peaceful exit with ambitions to launch a scalable startup studio independent of any existing VC firm. Madrona, alongside an additional 13 venture firms and Seattle angel investors, like Jeff Bezos and Zillow -founder Rich Barton, bolstered PSL with seed capital right off the bat.
The validation engine
Pioneer Square Labs’ network of entrepreneurs
To differentiate itself from competing company builders and maintain a high level of efficiency, PSL uses a proprietary strategy of rapidly testing and validating business ideas dubbed its “validation engine.” Its special sauce, PSL leverages digital marketing to validate customer demand before they begin real work on any of their ideas.
Long-time marketer Peter Denton leads the effort. Denton, who joined PSL in early 2017, manages day-to-day market validation, growth strategies and market research for the firm’s portfolio companies.
“We joke in some ways [Denton] is the grim reaper,” PSL’s Ben Gilbert told TechCrunch. “He’s responsible for much more kills than anyone else.”
Among the validation engine’s strategies is to build a website for a “company” to test demand for a potential product. Denton and his team market the website to target customer segments through a variety of digital channels, then measure customer resonance with the messaging. They ask potential customers if they are interested in learning more about a new concept or product when it “becomes available” to help understand how much interest a potential business might have before PSL allocates additional time and resources to a project.
To date, PSL has killed more than 100 ideas.
“A lot of studios ultimately won’t be successful because they don’t kill things fast enough,” Gottesman explained. “We kill nine out of 10 of the companies we start. Most of our ideas don’t make it to the promised land.”
In a sense, they are catfishing potential customers, luring them in with a new idea that more than likely will never come to fruition. But the strategy saves PSL the heartache that comes with investing a lot of time into a business idea that never finds its market.
This way, when an idea does pass the tests posed by the validation engine, PSL and its team of engineers and data scientists are ready to build with knowledge of market demand in tow.
By the numbers
A glimpse of Seattle’s Pioneer Square neighborhood where Pioneer Square Labs is headquartered
In three years, PSL has spun-out 13 companies, ideas for six of which came from the PSL team and seven originated from founders in the PSL network. All of those companies have secured venture funding — $71 million in total for an aggregate valuation of $200 million.
“The most important lesson we learned is it’s all about the people and the talent,” Gottesman said. “If we have an A-plus idea and partner with a B team, the company isn’t going to be successful. On the other hand, if we partner with the best talent, we are likely to be successful even if we fail on other dimensions.”
PSL’s goal is to invigorate the Seattle tech ecosystem and given the aforementioned stats (PSL companies comprised 14.3 percent of all early-stage VC deals in Washington state in 2018) they are well on their way. In 2019, PSL hopes to spin out between six and nine additional businesses.
“We believe we are building the center for early-stage tech innovation in the Pacific Northwest,” PSL’s Julie Sandler told TechCrunch.
Seattle, home to two of the most valuable businesses in the world, has not created as many founders as anticipated. Amazon’s entrepreneurial culture has succeeded in keeping top talent from pursuing their own businesses. PSL’s derisked platform, the firm hopes, will entice those founders, like Boundless CEO Xiao Wang, a former senior product manager at Amazon.
“The studio model lends itself really well to people who are 99 percent there, thinking ‘damn, I want to start a company,’” Gilbert said. “These are people that are incredible entrepreneurs but if not for the studio as a catalyst, they may not have [left].”
Venture capital investment in Washington state is increasing year-over-year, reaching a high of nearly $3 billion in 2018 across roughly 400 deals, per PitchBook. The Seattle tech scene, given its proximity to tech heavyweights and a growing number of satellite engineering offices, only has room to grow.
“We do think Seattle is the most exciting market in the country because of the amount of technical talent you have,” Gottesman said. “You have to believe that if engineering is at the heart of these startups then Seattle will ultimately be a key city in the world in terms of creating great technology startups.”
“We think part of the issue is a lack of capital and a lack of help,” Gottesman added. “If we can provide a little bit of both of those things, we can really put Seattle where it deserves to be, should be and will be.”
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