6 months in

I’ve spend the last 3 weeks spending time with my alma mater, my investors and YC folks.  It’s been a rare opportunity to abstract myself from the grind of a startup and zoom out to 10,000 feet and think.  Here’s my learnings from the most recent experiences:

Successful people are human

A recent weekend brought the second ever YC Camp.  YC alums are invited to get offline for a weekend of mountain air, campfire chat and conversations with some of the most intelligent and successful folk in our part of the world.  Topics ranged from Trump to what’s more likely to end us: AI or synthesized biology.

You would be chatting to someone for 15 minutes around some smores about something interesting like what’s the real potential of chatbots, then I’d ask hey, what do you do.  Nearly always, my mind would be blown.  Amongst the ranks were Dan Ingalls, pioneer of object oriented computing; Justin Kan, founder of Twitch which sold to Amazon for $1b; Kevin Hale, who with little investment led a remote team to win in the online form space; Jared, who built Scribd and John Collision, who founded Stripe.  An illustrious list of successful folk.  There were lesser known names who demand just as much respect.  Oh, I just got acquired for a cool hundred million.  I’m from XYZ, which later research would reveal was worth a few billions dollars.  Yet, we invariably wore the same things: nike shoes, chinos, collared shirt and patagonia jacket.  We talked as equals and I was treated like one.  

Takeaway: success or failure – be human.

Be bold enough to have a conversation – they’re human too.

Be humble enough to never talk down – they’re human too.  

Think Big

I had many conversations with investors and advisors.  There were as many great pieces of advice relevant to our situation.  However, I was having lunch with one of my mentors when he  blew my mind.

We are going into a period of experimentation and had unconsciously drawn some constraints around our future paths: geographically and functionally.  Given our current status, we were looking to launch experiments that are a slight extension from our current product.  Instead, he smashed those thoughts by reframing our path to date.  We’re in a highly enviable situation.  We have time, a team, exciting markets and a willingness to fight.  We should think about solutions that can scale globally to solve the biggest pains we can find rather than limit our option set.  Mind blown.

Takeaway: reframe your current situation based on your strengths.  Now think global and do forward planning.

Think Small

Some of my favorite moments were outside, breathing in the crisp Bay Area air and contemplating life with some of the folk I get to call my close friends.  It seems our generation is one of contemplation with a willingness to change often and a desperate desire to find purpose and profit.  A recent Tim Ferris podcast had incepted stoic philosophical discussions amongst many of the conversations.

Strangely, it’s in these small moments I’m happiest.  When I abstract myself out and watch our conversation from above.  When I see a smile in my wife’s eyes.  When an investor/advisor or mentor blows my mind.  

In the grind of startup life I hadn’t had many of these moments in the past few months.  The last one was when one of the team sent me a Slack message that joining us was the best decision her career and that we felt like her family.  

Takeaway: I’m going to go for more small moments

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