Going Big, Going Home & a $1.6M Guitar

Dave Balter
Startup Grind
Published in
4 min readJun 1, 2017

Last night, Brian Halligan went big. He purchased Jerry Garcia’s famous “Wolf” guitar at auction for $1.6M, with all proceeds going to Montgomery, Alabama-based Southern Poverty Law Center.

You can see how it all went down in the clip below.

Brian Halligan landing a $1.6M winning bid for Jerry Garcia’s “Wolf” Guitar

Let’s get this out of the way:

Halligan is a Deadhead’s Deadhead. He simply loves the music, and everything it represents. He’s studied the band’s philosophies so deeply, that he was able to utilize them as a basis for his book about inbound marketing. I’ve been to hundreds of shows and have met thousands of deadheads and, truly, when I think of a Grateful Dead Fan, Brian — all groovin’, smilin’ and singin’ — is the image that first comes to mind.

If anyone should own Wolf, it should be Brian Halligan.

Jerry Garcia with Wolf 2

Somewhere around 2009–2010, I joined a CEO group that included Brian Halligan. This was earlier days for his company Hubspot, and he often exclaimed to the rest of the CEOs his mantra: “Go Big or Go Home”.

The group of CEOs gave him a lot of heat for that, partly because we were more risk averse than he — but, truth be told, probably more because of our own inferiority complexes.

And yet, his “Go Big” lesson to us eventually became evident: in the fall of 2014, Hubspot went public, generating great returns for investors.

And while going public felt like the culmination of the dream, Halligan had a much bigger lesson for us in store.

That’s because “Going Big” wasn’t at all about taking your company public or making a boatload of money.

“Going Big” is about being able to do the things that mean the most to you; to fulfill life’s most fantastical dreams.

In one fell swoop, Brian donated a ton of cash to a great cause AND is now the proud owner of one of his hero’s most prized possessions. Simply put: Brian’s purchase of Wolf is a reflection of the entire entrepreneurial journey.

Thank you Jerry, for a real good time.

If you can’t do something like buy Wolf, then Halligan’s right: You should Go Home.

Wolf was delivered to Jerry Garcia in May of 1973 by Doug Irwin — Garcia paid $1,500 for it. It had a 25.5 in maple neck, a 24 fret ebony fingerboard, a blonde Western “quilted” maple body with at purpleheart (amaranth) core. And it’s inside was like a Strat with an Alembic Stratoblaster installed.

In the fall of 1977, Garcia had Wolf modified by Doug Irwin (it apparently took two tumbles, one down a flight of 13 stairs, during the first era). Wolf 2.0 had single coils and effects loop. Also, Irwin removed the Wolf sticker and inlayed the Wolf into the guitar, and removed the Peacock on the headstock and added his signature Eagle logo.

Jerry Garcia’s Wolf Guitar

Garcia played a number of other guitars through most of the 1980s, but eventually Wolf returned in the fall of 1989 where it was a guinea pig for MIDI synthesizer effects he was toying with. By 1990 it went back in its case and that was the last Wolf was played by the Grateful Dead.

If you’re an entrepreneur of any sort, Halligan and Wolf should be a north star to guide you. Yes, focus on Going Big, but do it for the right reasons. Do it because the pot of gold at the end of the rainbow isn’t really about the gold. It’s about the ability to turn that pot into the gold ring you’ve always reached for.

As usual Garcia (with his lyrical wingman Robert Hunter) said it with much more dramatic flair in their song Crazy Fingers:

Midnight on a carousel ride
Reaching for the gold ring down inside

Never could reach
It just slips away but I try

Halligan reached for it. He went big. And this time it didn’t slip away.

If you are Going Big, hit the ❤ below — or Go Home.

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