Startup Society

How a New Program Helps Seattle’s Big-Tech Workers Become Founders

Venture Out allows Amazonians and others to develop their company ideas without ditching their day jobs.

By Benjamin Cassidy April 8, 2020 Published in the April/May 2020 issue of Seattle Met

Brietta Easterlin and friends had secured most of the essentials for an Expedia coworker’s birthday banger—a room atop a downtown apartment building, a keg, pint glasses with HTML printed on them. One party staple was missing, though: food. Shouldn’t be a problem, Easterlin figured. Yet, after two weeks of unreturned calls, endless online forms, and insulting price negotiations, it would take a friend’s connection for Easterlin to finally pin down a private chef. All the hassle left her wondering, Why was this so hard?

The longtime product manager wanted to form a company to solve the problem, an idea that lingered even after Easterlin landed a gig at She had just bought a house with her partner in West Seattle. They had a dog. It maybe wasn’t the best time to abandon a salary and benefits. “It took a long time to actually cut the cord from big tech,” she says.

Ultimately, her project didn’t progress fast enough as an after-hours enterprise. In September she left Indeed and devoted her full attention to Experience Shindig. Her startup’s platform allows party planners to book caterers and other services and, in turn, gives chefs easy access to customers year-round. The concept appealed to Venture Out, a firm that provides guidance to big-tech vets and alums as they develop their companies. While King County has long supported a strong startup scene, its industry behemoths (Amazon, Microsoft, Google) have shaped its tech-world reputation by retaining much of the region’s talent. That may be changing—Seattle-area startups broke a record for venture capital funding in 2019—but tech giants can still wield attractive financial packages, or golden handcuffs, to keep employees around.

Founded by Sean Sternbach and Ken Horenstein, Venture Out greases those shackles with a new 10-week curriculum that includes a classroom approach to startup basics—how to raise funds, acquire customers, and build a financial model—as well as advice from more than 50 mentors. In return, the company gets a 4 percent stake in participating businesses. It competes with a crowded accelerator field but requires a generally lower commitment level: Participants don’t have to quit their day jobs to sign up.

For those who do make that leap, the risks aren’t just financial. Montana Wong, a former Amazon software developer, faced an unfamiliar loneliness when he began toiling remotely on his streaming-based startup, Sengage. As an antidote, he attended one of Venture Out’s invite-only Founder Forums, regular meetings that helped spawn the program where Easterlin honed Experience Shindig. For Wong, the gathering offered welcome counsel and camaraderie. And if future attendees demand some grub, organizers shouldn’t have to look far for a caterer.

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