Who is Your First Phone Call?

Andrew Maguire
Jul 17, 2018 · 5 min read
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Morpheus from “The Matrix”

The Inspiration to Start a Company

Eighteen months ago, on Christmas Eve, I had a few short hours left to sign the documents that would finalize the sale of Looksharp, the company I had founded and worked on for the first seven years of my professional life. Achieving an “exit” is one of the hallmarks of entrepreneurial success, but as the midnight deadline loomed and despite agreed upon terms, I felt deeply conflicted.

Moving Forward

Back when we raised our Series A, I had the opportunity to meet Jason Portnoy, Founding Partner at Oakhouse Partners. Over the next few years we developed a close relationship and Jason became my first phone call on many of the toughest challenges I encountered in building the company. It’s not easy to talk to an investor when you are facing problems related to the founding team, or firing a key executive, or questioning whether you actually do have product market fit, or considering whether or not to sell the company. Those are questions that left me, as an entrepreneur, feeling deeply vulnerable, especially when talking to people who had invested money into the business. That’s the catch 22 of the investor-entrepreneur relationship. A great investor can add incredible value, but only if they know what’s really going on. As an entrepreneur I had to feel like I could trust Jason enough to offer guidance without his own “investor interests” getting in the way. He excelled at leaving his agenda and ego at the door, which I learned over time is a hallmark of Jason’s relationships with other founders he works with as well.

Oakhouse Partners

Oakhouse Partners invests in companies that use…

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