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Meet Michael Skok And Underscore VC

My work style blueprint and an introduction to !

About Me 👋

Inspired by innovation and entrepreneurship, I started my first software business as a teenager, spent 21 years as an entrepreneur, and then the past 18 years as a venture investor, co-founding Underscore VC in mid-2015. Along the way, it’s been a pleasure to mentor and teach at the Harvard’s Business School and iLab, and create the series. You can learn more about my focus on investing in world class people and breakthrough technologies

About Underscore VC 💛

Underscore VC is a Boston-based venture capital firm backing bold entrepreneurs from Seed to Series A with an aligned community designed to fit each startup's unique needs.
Today, capital is a commodity. That’s why Underscore created a unique venture model that prioritizes the most important ingredient to a startups success: an aligned and proven community to help you build your business at every stage of your multi-year journey. We call this community the .
Now several hundred strong, the Core is comprised of top entrepreneurs, seasoned executives, up-and-coming talent and domain experts who not only support each other as peers but also are uniquely incentivized to help Underscore source, select, and support portfolio companies.
The Core is easily navigable for portfolio company founders seeking aligned advisors. Those that are selected by the founders, and accept the role of serving as a , are compensated with an interest grant from Underscore in the company they partner with. What does that mean? It means these valuable advisors come at zero cost to the entrepreneurs. To date, because of this unique model’s proven results, Underscore has allocated millions of dollars to Core Partners, making them truly aligned to an entrepreneurs success.

My Work Style Blueprint 💡

5 ways to get the best out of me:

It’s always great to know and understand the personality type of those you’re working with (the Underscore team has profiles in Coda with this information and how to get the best out of them). I’m a Protagonist ENFJ - T
As a big proponent of pre-reading and preparing before a meeting, be sure to allow me the time to come prepared and send me things in advance of a meeting to review. "Fortune favors the prepared mind!”
As a visual thinker, physical or digital whiteboard are a must for me. If you join me for a meeting in the Underscore office, you’ll note that most walls are actually whiteboards. And if you join me on Coda, you’ll find a Miro whiteboard embedded in my work.
I take a lot of notes, and I like to see those I’m engaging with doing the same. I’m always extra excited when someone I meet with sends me a write up from our meeting confirming what they heard, and what actions or next steps there are. Bonus points if they share the who, what, when, and the why around the actions! (Again Coda has made this all very easy to do using their Templates and Collections)
Give me honest feedback after a meeting, presentation, or discussion - I love learning and improving - particularly when it’s clear and actionable. Even better, suggest what you think I can change to improve. I love to actively evolve - it’s one of our values at Underscore VC - here’s our emoji for it 🔁

What do people tell me are my super powers?

Caring deeply about people and working with colleagues and founders to mutually learn and improve.
💡 Tip: Share with me how to be most helpful and where we can improve.
People often call on me to lead and provide vision. Use me for strategic work.
💡 Tip: Direct my energy towards the high-level thinking and to solve puzzles.
Apparently public speaking, teaching, and mentoring are in my blood.
💡 Tip: That’s good because I’m happiest doing this work, so engage me in it!
At Underscore VC we believe in being strong active listeners to entrepreneurs. Practicing it, I’ll scan the room (or zoom) to check others are hearing, and synthesize and verifying that.
💡 Tip: Utilize my facilitation and put me in front of a whiteboard to check and clarify.
My life was out of control growing up, so it’s caused me to be focused, organized, disciplined, and conscientious.
💡 Tip: I believe showing up is the start, quitting is for losers and following up to the finish is the only way to win.

What are my weaknesses?

Do you want the full list?! We’d be here for pages! Here are the top 3 I hear:
At times I can get so focused that I miss what’s right in front of me! Give me a tap on the shoulder and I’ll snap out of it :)
It’s a pleasure to lead but I’m not a project manager - I’ll get tangled up in the weeds if you let me. Ask me “why” I’m doing something and I’ll jump back to help define the impct we can have.
I’m generally patient and very encouraging of failure. In my book there is no failure, only learning, when people are fully applying themselves.

Fun Facts! 😎

Both my parents were orphaned.
My favorite sport is skiing ⛷️ (but sadly I’ve broken both legs - simultaneously 😬 - while doing it).
Started my first business programming calculators, and later computers while still in school.
I love photography - and very occasionally post on

About This Doc 🔍

Last updated:
I hate talking about myself but was asked to provide this document to give people a sense of what it’s like to work with me. We’ve noted a trend towards others doing the same (e.g. Luc Levesque calls this a ”, First Round calls this a “”, and investors such as have created their own to share). I’m hoping this will be a living doc to help people get the most out of working with me and .

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