Hart asked if I still write. I do, but I can’t blog as openly about life because of work. War stories are classified. Part of me wishes we’d followed through with filming everything with GoPro necklaces so we could carve the 99% that’s talking to computers to expose the gristle of business drama. But what’s the point? Nothing’s like what anyone can tell you.

Apptimize crew sailing around San Francisco

Much work is objectively boring and hard for a long time. That’s what it takes to win, tens of thousands of hours of work that no one else is willing to endure. It takes a wizard every hour of every day for years and years alone in a dark tower to draw the spell to craft and mark a new world. It’s pain, loss, sweat, time, boredom, all while fervently believing you must triumph.

More and more, I find myself saying, “I can tell you more in person.” I’m swimming the strange intersection between business and personal, because a startup is water that touches every part of you. In the ocean you feel the reality of constant motion, relentlessly pushed, engulfed by the smell and sound of the heavy waves. Fixate on the mission and row with boundless energy, lest you’re wrecked instead of carried. All your customers and friends and teammates swim together, making the same waves.

The amount of change Apptimize has gone through this past year is staggering. We’ve all changed. I was always ambitious, but my drive was as nothing to my fresh hunger, now that I know more what’s possible. Interviewing an executive candidate, he said, “Your words make me restless,” probably a funny reaction to debating the nuances of sales pipeline definitions.

A year ago, Apptimize was totally different. We made less than our server costs. Much of the impossible stuff we did, we were only able to do because we had no idea what we were getting into. I’ve seen us get so much stronger operationally, starting with learning the difference between strategy, plans, and goals. We’ve rebuilt again and again. We’re now about 25 people, long past fitting around the dinner table at my house, even with all the leaves in.

I’m different. After my previous life of prop trading our own money, I realized I love sales and the responsibility of customers. After 30 years of disdain, I started wearing high heels. I bought a brass rat; maybe one day I will consider actual jewelry. I finally started drinking alcohol. I’m learning more how to wield my weirdness: once upon a time, minutes after meeting someone I’d be ENTJ-ing them towards increased efficacy. Now I give it more time.

The last time I changed a lot was when I moved from NYC to the Bay. That was hard because I loved NYC. No matter how deep you get, NYC shows you something that takes your breath away, realizing you didn’t begin to know her yet. Deep was my love was for New York, the people, myself. I’d take the train down weekends to see my mom in Princeton. When Mom died, one of my best friends since 6th grade drove into NYC from Pennsylvania and I took her to my favorite foods. I had no hunger for food. A few months later, I moved from NYC to Palo Alto because I felt useless. You can’t be useless.

An addiction, NYC poisoned SF for me. I’d plan clandestine visits around NYC wishing we could get back together if it’d change just 1 thing. I’d fantasize about a bicoastal relationship, a modern jetsetter, brimming with love for everyone and no one, ready to forsake town whenever it threatened to get tiresome.

What is a home? I find my home whereupon returning from a journey the smell of the street fills me with gladness and relief and I restrain my haste in knuckling keys into a door to find a friend waiting inside to swing me in her arms and bring me tea.

For the last 3 years I swore I couldn’t find such a home in SF. The homeless people: that’s one of the first shocks. It still astounds me, the looks on their faces, approval through our mute acceptance. I drown in disgust and shame for them, myself, all of us. I lash myself to the mast and sail through the tempest. I staunchly ignore them and consider my own fortune. I resolve, “One day I promise to fix this pain. I’m still getting stronger and one day this will be simple to correct.” I retort, “Another empty, foolish, impulsive promise.” I rationalize, “This isn’t the most important thing.” I anguish, “But how do you know?” How much can you harden your heart before you’re no longer human? How much can you reach back towards suffering before your life is no longer yours? Ripped and bloodied I reel until another of my multitude rips me from the centrifuge, sighing in my ear, “Enough, enough.”

Contemptuous and hating SF, 3 years ago I moved from NYC to Palo Alto. The South Bay has its own sedate majesty. Driving down from SF it’s like descending from Mount Doom into an Eden of sweet, warm air. Understated and grand, even the woods are a suburban paradise. Everyone’s changing the world in their garage- NBD. I plucked giant, perfect fruit from yielding trees, sucking the juice from my wrist. But I can’t stay still no matter how comfortable and serene- onward, onward, pushed out of paradise by the waves of the world.

In December 2015, I moved from my house in Mountain View to an apartment in SF. It rained and the SF streets were unprepared so I took off my wet socks at Plow. My soaked book crumbled. It rained as we explored an abandoned nuclear site. Nick reassured, “I’ve been over this area with my geiger counter and it’s not that bad.” I like cold, I love SF’s temperamental weather, I like Land’s End, the way the wind blows the water white and black. I don’t live next to water or eucalyptus; I’m tabling that until after I settle this next thing with my business. Today I live in the Mission, a place Dan took me years ago and I instantly hated. Love blooms more lustily out of the ash of initial, prolonged dislike. Love: you don’t say it yet but you start thinking it. NYC has much of the best of today, but SF is the swan of our hopes for everything in 100 years.

That’s what you discover in a startup- even after sighting product market fit, you never stop pushing the market and product and reinventing everything. I love my startup. I love SF. Join my SF crew! Come away with us to navigate this life together! Shall we press forward together no matter how comfortable each stopping place is? Shall we strive and adventure together until we die?

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