2018

January

  • Week Four: Decided to launch Junto, worked on prototypes for a video streaming project and ate at Galli. Third week in a row waking up at 5:00 AM —recognized how social confidence in uncomfortable situations is my trojan horse for a lot of what I desire. Booked a flight to Lisbon.

February

  • Week One: Made the decision to begin pursuing an analyst role in VC. Failed to push Junto forward. Built mockups for Listening Party. Read two hours a day. Dined at Babbalucci, Sugar Fish, Aurora Soho (Cal Ripken Jr. spotting), danced at Gonzalez & Gonzalez, ping-pong at Spin. Concluded that every Friday night should be a sit down dinner and one day a week should be spent alone. Took a lot of notes. Used the 80/20 rule to identify what makes me unhappy: measuring myself with against others, self doubt, disorder.
  • Week Two: Redid my resume and applied to a few analyst roles. Began “Thinking in Systems” by Donella Meadows. Spent the weekend at a founder retreat with some incredible people in New Canaan, CT. Ate complementary of OneTable at Aurora in Williamsburg — not recommended and saw Two Feet at the Music Hall of Williamsburg — also not recommended. Had an extraordinary meal at Dirty French with my cousins and their writer friends. Realized that I 1) market myself poorly: as both an industry and skillset generalist 2) enjoy myself more when with older people. North star is 120 books in the next three years.
  • Week Three: Continued to apply to analyst roles — fully emerged in the process. Scheduled outbounds re: Listening Party customer feedback. Quit “Thinking in Systems” by Donella Meadows, started “The Black Swan” and “Think and Grow Rich.” Begin the process of finding a studio (downtown). Went to MediClub, a group meditation event and realized how much I love being in uncomfortable situations. Spent the weekend reading. Ate at Rossopomodoro (friends) and Boqueria (great uncle). Listened to Chris Hughes talk about guaranteed income inequality. Received a nice response from a cold outbound to someone I admire. Had a second meeting about a potential acquisition for Influencia. Recognized that the more successful people I meet and the more I learn, the more I admire my friend Jonathan Wood. Recognized how severely I have down played my accomplishments in my first startup. Recognized that my biggest flaw is in being fragile which results in a lack of output because I get in the way of myself. Working on that. Happy.
  • Week Four: Sent out a lot of emails, landed three interviews — the goal is to optimize for inspiration. Ate at dell’anima, kaoroumc, ROKC. Hung out//interacted with inspirational people. Realized that a bar is a modern day Emperor’s New Clothes. Finished Think and Grow Rich. Acknowledged that I am a generalist in every way: skillset, enabling technology, vertical. Emailed 10 people who know me well for feedback and got interesting response. Learned that a founder is a PM then a recruiter. Observation(1): Social norms states that if you proclaim that you dress well you are a loser but if others say that you dress well you are cool. Observation (2): freewill takes practice. Observation (3): social clout is mental mcdonalds; eat less mcdonalds. Present.

March

  • Week One: Sent out way less emails than I planned. Had three phone calls that didn’t go anywhere — got frustrated, tied my identity into work and got into a funk. Worked to get out of the funk. After identifying how pointless bars are, I went twice this week. Got better at ping pong. Started an online speech course. Realized that my worst habit is not completing initiatives, being indecisive and lack of consistency. I can do anything not everything. Built the outline for another small e-commerce residual business and began to execute. Decided to dedicate myself to (skill) product and (technology) AI. Ate at Spaghetti Incident, Made Nice (2x), Sugar Fish, and the Freehand Hotel.
  • Week Two: Biggest weakness: I take on too much. Result: lack of consistency, quality, execution, output. Last week was a continuation of attempting to land a venture capital role and a refresher of the lack of opportunities available. Lost Ping Pong tournament, attended Inscape Meditation (below average) & MNDFUL (awesome), got locked out of my apartment and read Great at Work by Morten T. Hansen (solid), Hooked by Nir Eyal (solid), The Happiness Hack (below average). Took a step forward with the e-commerce project. Packed for Europe. Grateful.
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