04
Sep
Fri
in-person
Should You Exit - And When?, Dave Parker, Trajectory
Most exit conversations happen too late — once a banker is hired and the process is moving. The harder questions come earlier, and founders rarely have anyone to ask.
Is this a business to keep or to sell? Does $50M in your pocket beat a few million a year for the next decade? Do you run a process, or wait for someone to come to you? At that scale it always feels like things are about to get better — how do you know when they actually are?
The host: Dave Parker is a five-time founder who has sold several of his own companies and been through an acquisition as an operator when UP Global sold to Techstars. He runs "Prepping for Exit," an M&A curriculum for founders distributed through Techstars, works with an M&A advisory firm, and sits on four Northwest mid-market boards.
What we'll cover:
- What a good exit looks like at your scale - and how buyers actually value a business like yours
- Timing, and the trap of waiting for one more good quarter
- Running a process versus letting acquirers come to you
- The part nobody prepares you for: what changes for you personally after the deal
- Open discussion — bring your own situation
Closed-door conversation, not a talk. Whether you're years away or already fielding inbound, this is where you can ask the questions you can't ask your board.
Speaker
“
Dave Parker
Founder and Chair. Trajectory.
I've spent my career at the intersection of entrepreneurship, community building, and global impact—always asking: How can we help more founders succeed? My success was always about the team you build around you.
As CEO of the Entrepreneurs' Organization, we led a global network across 87 countries, driving our highest-ever membership growth and achieving exceptional retention. As COO at UP Global (the Startup Weekend/Startup America merger), we scaled events from 550 to 1,250 annually, reaching 74,000 entrepreneurs before our acquisition by Techstars.
My real education came from being in the arena myself. I'm a 5X founder who's sold three companies and been part of over 20 transactions as CEO, operator, and advisor. Those experiences shaped everything I now bring to the founders and organizations I work with.
I wrote "Trajectory: Startup—Ideation to Product/Market Fit" (Hubspot's 2023 Business Book of the Year) because I wished someone had handed me that roadmap when I was starting out. Today, I share those insights as a speaker at accelerators, universities, and startup communities worldwide.
In Seattle, I chaired the startup programs for the Washington Technology Industry Association's Board. We've served over 300 startups that have collectively raised more than $300M, earning a three-year, $750K Department of Commerce grant to expand programs statewide for underrepresented founders.
My investment experience spans from Mitsui & Company's $250M fund in Silicon Valley to Seven Peaks Ventures and Fearless Fund. Both earlier funds delivered solid returns, but what I value most is backing founders building something meaningful.
Having worked in nearly 50 countries—from Bahrain to Brazil, Tokyo to Tunis—I've seen that great entrepreneurs are everywhere. The question is: How do we give them the right support at the right time?
These days, I consult with founders on go-to-market strategy, revenue models, and exit planning. I've worked with thousands of founders through Techstars, Founder Institute, 500 Global, and other ecosystem builders worldwide.
When I'm not working, you'll find me in the Seattle area with my wife of 30+ years, our four kids, and our doodle—probably headed out for a bike ride or a round of golf.
01
all founders,
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02
current founders
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03
TRANSITIONING FOUNDERS
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04
CURIOUS FOUNDERS
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