A Thoroughbred Startup Desk

San Francisco, 2010. “Finished, Solid Beech 6 Ft Work Table — $110.” We struck on $95 because I had to drive across the bridge into the city. He texted an address off of 4th & Brannan St.

It was one of those office suites that got terrific, daytime sunlight. The guy had a sweet beard protecting a neat, pressed shirt. Unmanned squads of monitors with cable tumbleweeds and brand swag were scattered everywhere. Aside from central air, it was quiet.

As we were dismantling the desk legs and packing my car, I asked what idea were they hacking on. He explained they were shutting down after a failed pivot. We exchanged more pleasantries. I secretly started worrying about the traffic on the bridge.

I founded Caviar on that very same desk. After city expansions and fundraising, it survived the move to SOMA when Melis and I got married.

It’s still standing in my dining room. I can see Melis sitting at the desk from the hallway scribbling notes in her moleskin, building Fashion Mews. This will be the desk’s third startup. A true thoroughbred.

But for the life of me, I can’t remember what that first startup’s name was.


For a while I said I’d write about Caviar, but I realized the story isn’t over. The company I started three years ago with four other guys is moving steadily away from my orbit and growing tremendously under Square. Now on sabbatical, I have more peaceful days waking up to my beautiful wife Melis and exotic shorthair cat Ramen.

In Interstellar, Matthew McConaughey’s character Cooper (spoilers, obviously) yanks the pull handles as his spacecraft is falling apart, tumbling into the black hole. Inside that IMAX, I could feel the vastness of the void separated by mere centimeters of polycarbonate glass. What happens now? It feels familiar as I stare into the future unknown. But for the first time, I’m not suppose to know, and that is exciting.

A good friend of mine suggested that I do something completely non-work related, so I’ve booked a writing class and enrolled at a music production school. I’m dusting off my photography lenses with Melis’ new blog, Fashion Mews.

I’m also entering my 2nd reading renaissance at 29. Remember when you could binge-read a book like The Hobbit or Calvin & Hobbes and lose track of the entire week? I’ve almost forgotten how it feels to read voraciously for fun. I highly recommend Love’s Executioner by Irvin Yalom, a memoir of excellent short essays on psychotherapy patients and their tribulations with ego, guilt, and obsession.

Lastly, I’ve realized how many broken friendships, missed birthday dinners, and closed doors were scattered behind me. I’ve exhausted the good will of some folks and made enemies. Winston Churchill said, “You have enemies? Good. That means you’ve stood up for something, sometime in your life.” But I feel its bitter permanence and walls of silence. For that, I’m sorry I came up short. Time will tell.

If you’ve gotten this far, I’ll leave you with my roadmap in 2015, which is shaping up to be most excellent. One of my best friends KC is getting married in June and I’m a Best Man, my first. Melis and I are looking to live in Turkey for a bit. I’ve always wanted to lazily move from town to town, and what better excuse than my wife’s homeland? As always, I’m looking to see if I can still build another company, so let’s talk!

Many of you have big years coming up, professional and personal goals to conquer. I cannot promise a safe landing, nor if it’s possible. But, to quote a famous astronaut from said previous film, “No, it’s necessary.”

Nailed it.

Thanks to Melis for reading drafts of this post.

10 Must-Try Burgers in San Francisco 2014

It’s been three long years.* I think it took me two years to get over the hype of pedigree and go with what I genuinely liked: wet burgers. So in a way, this is my most personal list of favorites in San Francisco.** Enjoy.

10. [NEW] Double cheeseburger at Sam’s, North Beach 

Anthony Bourdain drunkenly tweeted this was a top 3 burger in his life & was featured in an episode of The Layover. The simple barstool setup with its walls muscled in patron photos who’ve graced Sam’s over the decades is dripped in city blue collar blood. Piping hot fries, a tab of Sriracha sauce, and the best off-the-grill burger you’ve ever tasted. You could shoot the shit with Mike if you’re lucky and he’ll regale you with tales of Chinatown & story of every city denizen that comes in.

The burger that started my journey to burger whispering.

9. [NEW] Drive in cheeseburger at Garaje, SOMA

This is easily up there in the most-times eaten entry with Sam’s. The most startup-ey one on the list, the fresh ground Angus chuck patty is char-grilled with only salt. Smaller on the 1/3 pound side, it’s only got a tiny pink (they make it medium), but a very generous slather of melted cheese punched through with a strong beefy flavor.

At $6, even the ramen profitable can grab a seat. Continue reading

All Great Lives Had Wilderness Years

The keener eye recognizes the “Pinch,” typically halfway through the story, after the Catalyst and right before the Climax. This is the point of no return for your main character where motivation is strengthened and what they have to do is made perfectly clear. The struggle within the character to understand their purpose to fight to the crisis, where all hope seems lost.

Turns out, this happens in real life too. And history has shown the different responses to what different historians have called, “The Wilderness Years.” Examples:

  • Bobby Fisher. The de facto greatest chess player of all time. The pure positional game in chess “energized him,” naturally understanding where every piece must go. His Wilderness Years drove him into the darkest chapter of his life. He never recovered, wandering aimlessly and died in an Iceland hospital, estranged from family and friends.
  •  Winston Churchill. Regarded as one of the greatest wartime leaders of the century, he was ousted in 1928 from the Britain’s Conservative government for the disastrous Gallipoli Campaign. Churchill assumes his career is over. But his maverick journey of being attacked relentlessly for unpopular views about the King’s abdication and Hitler’s threat highlighted his Wilderness Years, culminating to his ascension in 1939 as Prime Minster. He’d serve twice, winning a Nobel prize, and after his death was named the Greatest Briton of all time in a 2002 poll.
  • And the one that Silicon reveres, Steve Jobs. We’ve all heard from time and time again his 1985 to 1996 hiatus from Apple, as if the only meaningful times in Jobs’s life were those spent in Cupertino.

In fact, this middle period was the most pivotal of his life. And perhaps the happiest. He finally settled down, married, and had a family. He learned the value of patience and the ability to feign it when he lost it. Most important, his work with the two companies he led during that time, NeXT and Pixar, turned him into the kind of man, and leader, who would spur Apple to unimaginable heights upon his return.

To reflect, where are you in your story? Are you having trouble raising a round? Lost a key co-founder? Company deadpooled?

Embrace it. This is where your character must be sharpened by iron, to be tested right before the Climax, where you’ll face the toughest thing you’d have to face in your life.

“Don’t fear failure. Not failure, but low aim, is the crime. In great attempts it is glorious even to fail.”—Bruce Lee

Startup Life is Hard

I think what inspired me to write this post was inDinero founder Jessica Mah’s rather frank interview about the difficulties of founding a startup at Stanford. It might not ask a lot of hard questions, but it sure almost plays as a confession.

Startup Digest founder Chris McCann succinctly stated, “Startups are unimaginably difficult.

I don’t know how it is for the younger entrepreneurs in this city, but sometimes I’m tired of saying the same party line, “Oh it’s all grand, we just broke profitability a few months ago! Exciting times!” While all the above is true, I turned 27. My golden parachute savings have been ransacked. We’re burning through money. Because our startup might just die any moment, I don’t have much job security. I’m single nowhere near indicators of a serious relationship. Your balls may not be in a vice, but they sure are dangling in the winds with no clear indication of a safe landing.

Despite all this, no one is excited as I am to see where this journey leads. I have never met so many smart, amazing people in a short space of time, and never has anything else been as this rewarding.

As the poker gods would say, ship it.

Thoughts on Daily Deals From a Startup Perspective

With OpenTable announcing that they’re shuttering their daily deals leg, we tally another casualty. Facebook has formally withdrawn from the Deals Wars, BuyWithMe had a horrendous execution of laying off half of its workforce to be an acquisition target for Gilt, and everyone watched a general industry shakeout.

I failed to mention there was a company called Groupon…is that still IPOing? As a Partner at Munch on Me fighting within this fierce sector, I hope to lay out some personal observations. These are obviously my own opinions, and do not reflect Munch on Me’s organization beliefs whatsoever. Continue reading