Winning with a Hippie Heart

Dec 21, 2017

It’s hard to keep a hippie’s heart when working in tech, especially in San Francisco. In 2017. But we’re doing it at The Key, and as our inaugural year comes to a close, I’d say it’s a savvy business strategy.

When I say hippie, I know it brings with it a ton of meaning – distinct by person and their role (or having been alive or not) during the ‘60s – so I’ll define what I mean.

Primarily, I’d say it’s a feeling of connectedness to the universe or to the energy of a place or the consciousness of how values and outcomes and intention are intermingled and together impact success.  

There’s also a social justice element that is fierce.

And a bit of rolling-with-the-flow that is hard but necessary when much of our success depends on media trying to make sense of madness while also meeting an uncertain fate head-on.

Sometimes it’s the trappings: fair trade jewelry or old Levi’s.

But I mostly mean the first, prime example. That settling of our feet on the ground and trusting that by doing right by folks, and centering the work that means the most to us, and working as a united team, supporting each other’s whole selves, will pay dividends.

My bet is that it’ll pay higher dividends, for many types of businesses, but especially when measured against the cutthroat, eat-or-be-eaten, predatory model of some service businesses, where highest bidder always wins on the buy-side and lowest and most obsequious wins the contract.

An example.

The Key team has fun. We chatter and joke and sometimes snort with laughter over all sorts of things. Sometimes a bad pun, sometimes a shared memory of a crazy work situation, sometimes a meme or a text from a nanny about the dumb or hilarious shit one of our kids is doing…all sorts of things prompt impromptu breaks in the day.

During one such, we met a neighbor in our WeWork. We assumed he was disrupted by our chatter, but he was actually attracted to the collegial energy, which is surprisingly hard to find even in a room full of people.

We played the name game and found folks in common. He shared what he was working on, and we provided some counsel. Turns out it’s right at the heart of what we love to do. We’ve kept in touch and helped out at small moments and eventually met the rest of the exec team and today the founder and CEO.

Through the process we’ve talked about it across our entire team…from founders to apprentices, and our enthusiasm has grown.

This morning worked like many mad-frantic mornings for working parents. I dropped my kids off early to an early care program they go to before school sometimes. Except it was cancelled today for holiday party prep. So, I leaned on my mom as I often do (as often wondering HOW anyone does the imagined ‘balance’ without a village at the ready), and sped downtown, begging Siri to connect me to Kat to set her expectations on arrival.

Through butchered texts and a lot of laughter, we decided I’d valet at the Palace Hotel and I arrived with a few minutes – and a bag of hand-me-down toddler clothes that’ll go from my boys to Kat’s son – to spare.

Parking cost $60! Which made me feel equal parts appalled at the separate cities that exist in these seven-by-seven miles, and grateful that I could do what worked for the business without worry.

The meeting was glorious. More about how to work in true partnership and with efficiency that was respective of our different roles and coasts, less creds check and price rebalancing. Really none of the latter, because this potential partner trusts his team. We fell deeper for the work he’s leading, and connected as parents and people and long-time movers in an industry that is wild and full of wonder and weirdness (or worse).

The conversation flowed among industry acronyms, local jokes, talk of holiday travel and stories of our respective kids. We even looked together at some of the toddler clothes.

After deciding we’d go forward together, we each left – to the airport for a family vacation, to downtown errands and back to preschool for a holiday potluck.

The mess is part of the magic. The world sometimes does as it will. We can be our best and most true selves, making room for all the roles required of us and taking care of each other, and still win.  

That’s the path we’re choosing. Feels pretty essential. The Key, one might argue…

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