Michael Skok is Founding Partner Emeritus at Underscore VC, a Boston-based venture capital firm specializing in backing bold early-stage B2B software startups. Since co-founding Underscore VC in 2015, he has played a pivotal role in shaping its community-driven investment approach, which focuses on supporting founders in building enduring companies by leveraging a network-aligned venture model.
With over 40 years of combined entrepreneurial, investment, and educational experience, Michael’s career spans significant accomplishments both as a serial entrepreneur and a venture capitalist. He began his first software business as a teenager and spent 21 years as an entrepreneur before dedicating the past 21 years to venture investing, including a prior role as General Partner at North Bridge Venture Partners. His extensive background enables him to help startups progress from concept through execution, underscoring his practical operational expertise alongside investment acumen.
Michael is also recognized for his commitment to mentoring and developing entrepreneurs and innovators, and serves as an Executive Fellow at Harvard Business School, further establishing his influence within the entrepreneurial education ecosystem.
Underscore VC, under Michael’s guidance, closed its $58 million third fund in early 2023, marking a significant milestone as the firm completes a generational transfer and continues to enhance its community-based support for portfolio companies. Michael remains active as a trusted resource and adviser within Underscore’s team and portfolio, despite transitioning to Founding Partner Emeritus status.
His investment philosophy includes a notable emphasis on the Open Source software ecosystem. Michael was the first investor in Acquia, one of the largest Open Source companies globally, helping it scale and contribute to hundreds of jobs and substantial economic value. This reflects his broader interest in identifying and nurturing disruptive enterprise software startups.
In addition to his venture work, Michael has spent over a decade developing the Startup Secrets educational series, a well-regarded resource aiming to provide founders with insights and frameworks essential for startup success. This content has been delivered through workshops, YouTube presentations, and podcasts, including notable engagements like the VC Pathways podcast, where he shares practical knowledge on venture capital and entrepreneurship.
Michael maintains a strong public presence through platforms such as his personal website and social media, where he actively contributes thought leadership on innovation, venture capital, and startup leadership. His approach underscores the importance of alignment between investors and founders, community-driven support, and a deep curiosity-driven perspective that he attributes to driving financial and operational success.
Key Professional Highlights:
- Role: Founding Partner Emeritus, Underscore VC
- Industry Focus: Early-stage, B2B software startups, with special interest in Open Source ventures
- Experience: 21 years as an entrepreneur; 21 years as a venture investor; former GP at North Bridge Venture Partners
- Firm Milestone: Closed $58 million third fund in 2023
- Educational Contributions: Creator of Startup Secrets series; Executive Fellow at Harvard Business School
- Notable Investments: First investor in Acquia (Open Source software leader)
- Community Approach: Emphasis on aligning startups with a dedicated support network and investor-founder alignment
This profile positions Michael Skok as a deeply experienced industry expert with a strong operational and educational foundation, uniquely suited for engaging with startups focused on software innovation and enterprise scale-up efforts.
