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Greg Gottesman

The hidden link between Seattle and Spokane: Tech companies find success on both sides of the state

by Todd Bishop on June 12, 2024June 12, 2024 at 8:37 am

Back in 1999, when F5 recruited Jeff Stockdale to build its hardware business, expanding beyond its core expertise in software, the engineering leader had one condition for the Seattle-based technology… Read More

Remembering Tom Alberg: How an understated investor had an outsized impact on Seattle tech

by Todd Bishop on August 8, 2022August 8, 2022 at 12:05 pm

Tom Alberg will be remembered publicly for everything he did to help create and shape the Seattle region’s tech industry, and for his early investment in Amazon, seeing the potential… Read More

Pet sitting marketplace Rover grabs a bone, valued at $1.3 billion in latest SPAC deal

by Taylor Soper on February 11, 2021February 11, 2021 at 1:28 pm

Another day, another SPAC. Today, we’ve learned that Seattle online pet sitting marketplace Rover plans to join the public ranks via a merger with True Wind Capital’s SPAC that values… Read More

How Seattle startup studio Pioneer Square Labs spun out 25 ideas in 5 years — with more on the way

by Taylor Soper on January 8, 2021January 8, 2021 at 8:08 pm

The flywheel is spinning at Pioneer Square Labs, the Seattle startup studio formed five years ago by a cadre of Seattle’s leading angel and venture capital investors. In the course… Read More

Once a startup runt, Rover laps up $155 million for tech-fueled pet care marketplace

by Taylor Soper on May 24, 2018May 24, 2018 at 10:30 am

When Rover started seven years ago, many in the startup community snickered. There was no real business model, they said. A marketplace that matched dog owners with caretakers wouldn’t work, they… Read More

Startup studio Pioneer Square Labs raises $80M fund, aims to ‘flip VC model on its head’ in Seattle

by Taylor Soper on April 17, 2018April 17, 2018 at 10:47 am

Seattle startup studio Pioneer Square Labs is launching a new $80 million venture fund, expanding beyond its original company-building model and promising a new infusion of capital into the region’s… Read More

Seattle entrepreneur Matt Hulett joins Pioneer Square Labs to pursue new ideas in eSports

by John Cook on May 13, 2017May 14, 2017 at 11:06 am

Pioneer Square Labs is adding some bench strength. The Seattle-based startup studio, which has already spun out companies such as AdLightning, LumaTax, Boundless and JetClosing, has tapped longtime Seattle entrepreneur… Read More

How this ‘startup studio’ quickly axed 22 ideas and spun out three companies in one year

by Taylor Soper on October 12, 2016October 13, 2016 at 8:27 am

“Fail fast” seems to be the theme at Pioneer Square Labs. It’s been about one year since the Seattle-based “startup studio” launched after raising a $12.5 million round from 13 venture… Read More

Hey, Seattle leaders: Let’s regulate more than just Airbnb and VRBO

by Greg Gottesman on June 3, 2016June 6, 2016 at 11:05 am

Guest Commentary: Two years ago, after the Seattle City Council voted 9-0 to cap the number of UberX, Lyft and Sidecar drivers on our streets, I wrote that the City… Read More

GeekWire Awards, Newcomer of the Year: Vote for your favorite company, group … or truck

by Todd Bishop on April 20, 2016April 10, 2017 at 7:26 am

We’ve seen a huge influx of new engineering outposts in the Seattle region in recent years, as companies from Silicon Valley and elsewhere establish branches here to tap into the… Read More

Tips from top investors: How startups can succeed in an uncertain economy

by Madeline Vuong on February 19, 2016February 19, 2016 at 12:24 pm

How should startups navigate turbulent economic times? That was one of the questions posed to a panel of investors at the recent GeekWire Startup Day. With China’s economy slowing down, gas prices dropping,… Read More

Top Seattle investors raise $12.5M for new ‘startup studio’ Pioneer Square Labs

by Taylor Soper on October 1, 2015October 2, 2015 at 12:08 am

Geoff Entress has an impressive resume. The former securities lawyer and financial analyst is a venture partner at Voyager Capital and an angel investor in more than 80 Pacific Northwest… Read More

Greg Gottesman, Geoff Entress and Mike Galgon form stealthy new firm Pioneer Square Labs

by John Cook on September 17, 2015September 18, 2015 at 9:43 am

Three well-known Seattle investors have emerged at the helm of a mysterious new firm known as Pioneer Square Labs. Angel investors Geoff Entress and Mike Galgon have joined with venture… Read More

Make money in your free time: Spare5 raises $3.25M from Madrona, Foundry, NEA for on-demand work platform

by Taylor Soper on December 7, 2014August 25, 2015 at 8:12 am

As a veteran entrepreneur and managing director of Madrona Venture Group, Greg Gottesman has seen his share of successful — and not so successful — startups come out of Seattle. So… Read More

Dude, where’s my dog? Actor Ashton Kutcher invests in pet boarding marketplace Rover

by Blair Hanley Frank on November 3, 2014November 9, 2014 at 9:15 am

Rover is getting a little bit of Hollywood sizzle. The Seattle-based online dog-sitting marketplace announced today that actor Ashton Kutcher — yes, the guy behind films such as Dude, Where’s My Car?… Read More

MyWorksheets wins Startup Weekend All-Star competition, helping teachers digitize curriculum

by Taylor Soper on December 13, 2013December 13, 2013 at 2:56 pm

It’s not easy to bring the latest technologies into the classroom. But one group of entrepreneurs in Seattle has created a tool that may make life easier for teachers and… Read More

Live from TEDxSeattle: How student loans are killing entrepreneurship

by Taylor Soper on June 23, 2013June 23, 2013 at 5:19 pm

When Greg Gottesman’s father went to the University of California-Berkeley decades ago, he paid $203 — for an entire school year. Things have changed in absurd ways since then, as… Read More

Here’s why your next meeting should be spent walking, not sitting

by Taylor Soper on April 17, 2013April 17, 2013 at 3:41 pm

(Thanks to Twitter user @TroyJMorris for the Aaron Sorkin “Walk and Talk” tip — hence the video above) For those working every day, and especially in the startup world, it’s… Read More

Newsmakers 2012: Greg Gottesman, Matt McIlwain lead the charge at Madrona

by John Cook on November 29, 2012November 29, 2012 at 9:57 am

At a time when many are proclaiming the death of the traditional venture capital firm, Madrona Venture Group seems to be hitting its stride. The Seattle firm, originally founded 17… Read More

Someone Like You: An ode to my BlackBerry

by Greg Gottesman on October 8, 2012October 8, 2012 at 10:27 am

Never mind, I’ll find someone like you. I wish nothing but the best for you too. Don’t forget me, I beg, I remember, you said, “Sometimes it lasts in love,… Read More

Newly-formed W Fund to pump $20M into university spinouts

by John Cook on June 19, 2012June 19, 2012 at 10:46 pm

Washington’s startup community is getting yet another shot in the arm, thanks to the efforts of a newly-formed venture capital firm whose goal is to mine universities and research institutions… Read More

Online dog fight: Rover.com rival DogVacay launches Airbnb for pets

by John Cook on March 1, 2012March 1, 2012 at 11:52 am

This could be one very interesting dog fight. A new startup company out of Los Angeles by the name of DogVacay is getting some attention today after it launched an online marketplace for… Read More

Gottesman does it again, wins Startup Weekend with home security product Iron Blanket

by John Cook on January 16, 2012January 16, 2012 at 11:10 am

Seattle venture capitalist Greg Gottesman better watch out, or he might just turn himself into a full-fledged entrepreneur. For the second time in seven months, the managing director at Madrona… Read More

Rover.com devours cash to play doggie day care matchmaker

by John Cook on January 12, 2012January 13, 2012 at 11:07 pm

Rover.com, the Seattle upstart that matches those seeking doggie care with nearby pet sitters, has raised $1.8 million, according to a SEC filing. The site, which launched last month, has… Read More

Newly-formed W Fund includes heavy hitters from Seattle venture capital

by John Cook on December 6, 2011December 6, 2011 at 3:38 pm

University of Washington vice provost of commercialization Linden Rhoads wants the state’s largest research institutions to spin-out more innovative technologies, creating new startups that fuel the economy and create jobs.… Read More

Madrona throws Rover.com a bone, puts ex-Microsoft GM Easterly on leash as CEO

by John Cook on December 1, 2011December 1, 2011 at 1:50 pm

Aaron Easterly loves dogs, and a four-pound Pomeranian by the name of Caramel controls a good chunk of his life. But the former general manager of advertising strategy and monetization… Read More

Greg Gottesman, Brad Feld and others join board of Startup Weekend

by John Cook on September 27, 2011September 27, 2011 at 12:50 am

Startup Weekend, the Seattle-based non profit which coordinates 54-hour startup marathons at locations across the globe, has formed a new board with leading venture capitalists, entrepreneurs and execs from the… Read More

Like Turntable.fm for video, FlickMob gathers friends to watch YouTube clips

by John Cook on September 9, 2011September 9, 2011 at 8:08 am

At a Startup Weekend event in Seattle four months ago, a group of geeks built a service called Shubz.tv that allowed groups of friends to watch video clips together. The… Read More

IPOs roared to life in first half of 2011, but worries arise that the good times may be gone

by John Cook on August 19, 2011August 19, 2011 at 1:02 am

IPO windows tend to come and go. For the past eight months, that window has been wide open, allowing companies such as LinkedIn, Pandora and Zillow to start trading in… Read More

Does working at Microsoft really turn your brain numb?

by John Cook on August 18, 2011August 18, 2011 at 8:23 am

Call it the Silicon Valley invasion. Facebook, Google, HP, Zynga and Salesforce.com — driven by an insatiable need for talented software engineers — have all established fast-growing engineering centers in… Read More

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