Michael Skok has spent more than 40 years mentoring and developing entrepreneurs and innovators as a company founder, investor, and educator. He has contributed to building many unicorns — companies with valuations exceeding $1 billion — and directly helped build six as either a founder or investor and board member. His success is built on three pillars: identifying and supporting entrepreneurial talent, strategic vision to identify and invest early based on major technology shifts, and company building skills gleaned from both success and early failure in his own journey.
Michael is currently an Executive Fellow at Harvard Business School. In more than a decade of “Startup Secrets” programs at the Harvard Innovation Labs and Business School, he has shared frameworks, resources, and insights with thousands of rising innovators and entrepreneurs on topics including the customer’s value proposition, designing a customer-centric business model, startup culture, and strategy. Videos of these sessions have surpassed 10 million views on YouTube. Michael values these sessions, not just for the opportunity to mentor rising entrepreneurs, but because he enjoys listening and learning from the participants. His articles on startup strategy have been published in The Wall Street Journal, Forbes, and Harvard Business Review. His presentations and resources are also available for free on the popular and continuously evolving website startupsecretssandbox.com . Michael is currently creating a book and AIs based on the content of Startup Secrets, featuring case studies from dozens of both successful entrepreneurs and real world learnings from failed ventures. He is also giving all this content and experience to help Harvard build their Foundry program for even broader reach.
Michael’s strategic vision has driven his success as an investor. in 2002, he developed the groundbreaking investment thesis “Everything as a Service” , anticipating by several years software’s shift to the cloud. This led to investments including Demandware, a commerce enabling software startup that went public, then was acquired by Salesforce for $2.8 billion subsequently becoming more than a billion dollar revenue business as Salesforce commerce cloud. Even before starting as a VC he identified the megatrend toward open-source, and helped found and subsequently led the investment in Acquia to commercialize the Drupal content management project. Acquia became the fastest growing software company in America in 2012, according to Inc Magazine. Acquia subsequently surpassed $1 billion in value before being acquired by Vista where it continues to grow as a highly profitable business. (Full disclosure at time of this interview Michael had not yet sold any of his shares in Acquia.) Michael also took note of the wildly popular open source statistical analysis language R and backed a company provide support for it, Revolution Analytics, which was later acquired by Microsoft. Along the way he founded the Future of Open Source and Future of Cloud Computing industry surveys that gave rise to the broadest industry wide collaborations of their kind.
In 2015, following a year long listening tour interviewing hundreds of entrepreneurs, Michael was inspired to start Underscore VC. Underscore backs bold B2B software startups from Seed to Series A with a unique community support model in which successful startup founders and builders mentor startup teams and share in investment profits. Underscore and Michael shave invested in unicorns such as Coda (cloud-based collaboration, bought by Grammarly), Salsify (product experience management), Project 44 (supply chain management and been the earliest investor and board member of other high growth startups like TetraScience (scientific data and AI cloud), and CloudZero (optimization of corporate cloud costs), FXP (cloud security, development, and cybersecurity) and BusRight (software to manage school buses, student routes, and drivers).
Driven early on to carve his own path, he started his first software business at the age of 16, using the world’s first programmable calculator, the HP 65. Before going to university in the UK he was running a highly profitable enterprise, building diverse solutions from inventory control to portfolio management. Immediately after university Michael joined his brother to build Skok systems, a pioneering desktop computer-aided design system that was licensed by Hewlett Packard. He then started European Software Publishing, a firm dedicated to helping US software companies establish themselves in Europe. Various of these were acquired or went public such as Symantec. He also co-founded Alphablox, the first real-time in line analytics for global 1000 companies. to optimize business performance. Alphablox was acquired by IBM in 2001.
While Michael is known for enabling many to reach further in their careers to create thousands of jobs that in turn generated billions of dollars of value he personally remains humbled by learning from failure. At the pinnacle of his journey in 2019, Michael’s life was disrupted by a brain tumor. Because maintaining his health requires significant work, Michael retired from active management at Underscore. However, his continuing dedication to mentoring and inspiring innovators and entrepreneurs to solve more of the world’s problems motivates his ongoing recovery and remains his passion.
Personal
Michael has developed many hobbies over the years including some that cross over with work, such as investing. Ever since developing a portfolio management system for a brokerage house in the 80s he has kept investing in IPOs and public companies like EMC for storage then MSFT for PCs and CSCO for networking, then AAPL when SteveJobs returned, then AMZN when AWS was formed and most recently NVDA as AI emerged, building a market beating personal portfolio over decades that he shares openly with family and friends. (Full disclosure, at time of this interview he still held shares in AAPL, AMZN, MSFT, NVDA)
For pure joy, Michael directs his passion to sports, giving his all to everything from skiing to kiteboarding to – when feeling extra adventurous – pickle ball.
Michael’s main distraction in life is his photography. All the background images for his site are his own. He shares a small fraction of his images on instagram @mjskok and whenever requested for a good cause, gives his images away or makes them available for open usage on unsplash.
Michael is married with a daughter and a very large extended family whose privacy he respects and protects.