Michael Skok started his first software business as a teenager, spent 21 years as an entrepreneur and has been a venture capitalist for the past 15 years. The Underscore VC cofounder has founded, worked with and invested in startups, and created thousands of jobs and billions of dollars of value. Along the way, he also mentored and taught for 4 years at Harvard University, and created the Startup Secrets series. As an entrepreneur and an investor, Skok has focused on breakthrough technologies and disruptive business models including Open Source, Cloud, IoT, and emerging domains such as Blockchain, Virtual/Augmented Reality, and Artificial Intelligence/Machine Learning.
He has served on or is active on many private and public boards such as Acquia, Demandware (now a Salesforce company), Mautic, Salsify and Zaius. He has also participated in leadership roles in many industry groups such as the Software Publishers Association where he was Chairman for many years in Europe. In 2015, Skok co-founded Underscore VC, which has built a reputation as an active investor aligning talent from its Underscore Core Community with startups.
Enjoy a condensed version of our podcast discussion as a written Q&A below.
Where did you grow up?
Wiltshire, England
You began developing technologies when you were young. What got you into tech?
Programmable calculators.
Why did you move to Boston?
We intended to go to the west coast, but through a series of serendipitous steps we ended up in Boston.
What was it like founding a company with your brother?
Incredible fun.
What was one of the earliest lessons you learned?
Failure sets you up better for success. It’s important to be battled tested, and forced to our knees.
What was one of your more challenging entrepreneurial ventures?
Setting up Symantec in the UK, and start bringing their products across the UK.
What did you learn from that experience?
It’s really important to hire really great people. It doesn’t matter what product you have, or what opportunity you have, you need the right people.
How would you sum up the mission of Underscore VC?
We started Underscore VC with a listening tour, on a mission to find a better way to empower entrepreneurs to build an enduring company and support their full potential as an entrepreneur. Ultimately we believe entrepreneurship is the most powerful source for good. In turn, we’re creating a virtuous cycle of investing, building, learning and sharing to enable future entrepreneurs.
At Underscore, you’ve implemented a structured mentoring program for first-time entrepreneurs. Why?
First, we want to empower first-time entrepreneurs and support them as they build the next generation of world-changing iconic companies. But also, as a firm, we have our hearts set on blowing up the black box of VC and making it more accessible, and friendly even. Plus we’ve got a distinct advantage in serving these early entrepreneurs because we not only have the capital to back them with and the incubation space to host them in, but we’ve also got a Core community eager to mentor them and a whole business-building curriculum called Startup Secrets - something I used to teach at the Harvard iLab.
Underscore’s Core Community is growing, and the Core Summit is a vibrant Boston innovation ecosystem event. Where does the Core initiative go next?
Over the next few months, you’ll see us doubling down on building out the Core in 3 main areas that are super important to the earliest stage founders: product, customer success, and sales. Of course, we’ll have other Core events geared towards specific domains, or other functional roles, but these will be our main focus. Ultimately the goal is to foster these communities until they become self-sustaining: some of them are already well on their way.
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