If you think “liberal” and all the variations of “left” mean the same thing, let this be your wakeup call. Many things described as “liberal” today mean the opposite of what was historically true and what many people expect, and this disconnect is likely contributing to some of heightened frustration…

It’s only in a totalitarian state where everyone appears to agree on hard topics. If you look around you and see that, it means people are silencing themselves or being silenced. Neither one is okay. I’ve been silencing myself, but I’m done. Critical thinking, rational thought, and individual courage are…

Season 2, episode 3, “Elementary, Dear Data” Lesson: only talk in a meeting if you have something useful to say This post is part of my ongoing quest to watch every episode of Star Trek: The Next Generation and pull one startup, entrepreneurship, tech, or investing lesson from each. “When the Enterprise arrives a few days early at its rendezvous point to meet…

TL;DR: I’m an Operating Partner at Accomplice as of January 2020. I’m a contractor, continuing to serve on boards, work with companies, run Rev Boston, develop content for Spearhead, and do a few other things for the firm. I’m a co-founder with my friend Isabella Patton of our new company…

Avoid these ten instant disqualifiers — Fundraising is hard, especially for first-time founders. You have to learn a new language and skill set in addition to your day job (the not-so-minor task of getting a startup off the ground). Suddenly, you have to be conversant in valuations, SAFEs, fund theses, dilution, cap table math, term sheets…

Season 2, episode 2: “Where Silence Has Lease” Lesson: most companies almost auto-destruct at some point This post is part of my ongoing quest to watch every episode of Star Trek: The Next Generation and pull one startup, entrepreneurship, tech, or investing lesson from each. “While en route to the Mogana quadrant, the Enterprise comes comes across a…

Season 2, episode 1: “The Child” Lesson: the best way to understand a group of people is to immerse yourself in them (e.g., user testing) This post is part of my ongoing quest to watch every episode of Star Trek: The Next Generation and pull one startup, entrepreneurship, tech, or investing lesson from each. “The ship has a new chief medical officer, Dr. Katherine Pulaski, now that Beverley Crusher…

For all the millennials, introverts, and members of the general populace who realize that it’s 2019 and technology has given us more efficient options for solving problems than talking on the phone, here’s a voicemail template for you. I’m one robocall away from putting this up myself. Hi, you’re attempting…

Season 1, episode 25: “The Neutral Zone” Lesson: tech obsolescence only gets faster This post is part of my ongoing quest to watch every episode of Star Trek: The Next Generation and pull one startup, entrepreneurship, tech, or investing lesson from each. “Data finds an ancient space module from Earth containing three intact people, frozen for…