Trending: New security service from Cloudflare hopes to kill the VPN once and for all

Dear Geeks – This week’s top submission was juicy enough that names were changed to protect the not-so-innocent…otherwise, reprinted verbatim here. – Rebecca

Dear Rebecca,

I have a leather jacket and a hat with the [Startup X] logo, along with thousands of worthless stock options, from the now defunct startup that closed a few years back after burning through millions in investors’ money. I have been saving them for the Startup Failure Hall of Fame but I’m wondering if I could get anything for them on eBay? What would you advise?

Startup Casualty Seattle

Dear Startup Casualty Seattle,

Thanks for your lovelletter, SCS.  Without getting too “coulda, woulda, shoulda” and “better luck next time,” here’s a combination of retroactive and proactive advice from yours truly:

  • You just might be in a failed startup…. when the primary use of proceeds is expensive schwag. That leather jacket sounds pretty schweet, though.
  • Embrace the fail. Fail fast and iterate is good advice.  In this case fail fast and cheap might have been better.  This whole startup thing isn’t for the faint of heart.  Investors know it — when they’re swinging for the fences, the 1 out of 10 times it’s a home run helps make up for the 9 that aren’t.
  • Think like an investor. Startup co-founders and employees are absolutely investors in the deal.  High (if not first) on the checklist of investor due diligence is reference-checking.  During my time at the Alliance of Angels, an entrepreneur once came to us with a plan in a pretty competitive industry– clearly an execution play– but we were encouraged that he’d built and successfully sold another company in that space.  Or so we thought.  Our lead investor called that company, who responded, “oh that guy? Ya, he worked here for about a month four years ago.” Suffice it to say we didn’t do the deal.  We live in an age of transparency and it keeps getting easier to do your homework.  Work with people you trust, who have integrity.  In your case, SCS, you’ve now landed a gig with someone you’ve known and worked with for years.  You know what and whom you’re investing in.  I’m guessing you’ll wear that company hat with pride.
  • As for your hat and jacket….. do you have an entire collection of schwag?  You want to showcase a series of collectibles? Bonanza, baby.

Lest I forget: GeekWire t-shirts coming soon to a launch party near you. :) And of course you’ll never want to get rid of those.

xoxo Rebecca

Editor’s Note: Rebecca Lovell is GeekWire’s Chief Business Officer, a sage purveyor of startup advice, and a kick-ass karaoke singer. Have a startup question? Send a lovelletter to Follow on Twitter: @lovelletters.

Like what you're reading? Subscribe to GeekWire's free newsletters to catch every headline


Job Listings on GeekWork

Find more jobs on GeekWork. Employers, post a job here.