Who is Your First Phone Call?

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

I joined Oakhouse Partners in January of 2018 and would like to take the opportunity to share a bit of my story with the community.

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.

Growing up, my parents drilled into my head the belief that those of us with the privilege of financial stability and a good education have a responsibility to try to make the world a better place. My father, a former US Congressman and nonprofit executive, led a career defined by service to the public good. Nearly every night at the dinner table our family conversations turned to politics, which became increasingly heated as I grew older and started to develop my own worldview. At the time, politics and activism felt like the most effective ways to generate positive change. While I still believe strongly in the power of those approaches, I broadened my gaze in college to include technology, applied in the right ways, as a powerful tool for progress.

I graduated from Columbia University with a major in Political Science and was greeted by an economy in shambles. The biggest problem I could personally relate to was finding a job after graduation. This was mid 2008 and post financial market meltdown, and I was struck by how many of my peers who had planned to work on Wall Street were at a loss for what to do now that those jobs had disappeared. Millions of students at other schools would graduate that year far worse off than my classmates, burdened with heavy student debt and limited job prospects. I felt strongly that students needed better access to the countless opportunities that existed, even in tough economic times, ranging far beyond the select group of large employers with the resources to recruit on campus.

Upon graduation, I co-founded Looksharp with the goal of helping millions of college students and new grads find employment. After a brief stint in Seattle, my co-founder and I moved to the Bay Area and joined the first class of the 500 Startups Accelerator. We scaled up to millions of student visitors, hundreds of thousands of employers, and raised our Series A with participation from a number of venture capital firms, including Oakhouse Partners.

While Looksharp succeeded in gaining a large audience of job seekers and employers, we ultimately struggled to scale revenue at a pace that would justify raising additional capital. When people ask me if Looksharp was a success, I have a hard time answering. From the perspective of investor returns, Looksharp did not achieve success. On the other hand, the Looksharp team had built a product that secured millions of internships and jobs for college students and recent graduates. Those jobs marked one of the most important transitions in life — the shift from student to professional. In building a platform that empowered those students to connect with hundreds of thousands of businesses, startups, and nonprofits they would not have otherwise known, I know that we changed many lives for the better.

These were the thoughts bouncing around my head as I struggled to make peace with the outcome and sign the sale documents on Christmas Eve. For a couple of hours, I wasn’t sure if I could go through with it. Finally, realizing that I was wasting precious holiday family time, I signed the documents, closed my laptop, and turned my attention back to the present. It was one of the hardest things I’ve ever done.

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.

After Looksharp, I spent a lot of time asking myself where I should go next. Over the course of the next year Jason and I started talking about working together. Then, after a couple months of world travel and a cross country road trip, I joined Oakhouse Partners full time as Investing Partner.

In addition to being inspired to work with Jason, the idea of investing in and supporting startups was deeply compelling. Venture capital in general provides the opportunity to zoom out and look at the world through a broader lens, rather than burying oneself in a single problem. I’m excited to spend time thinking deeply about humanity’s greatest challenges and the role that technology can play in solving them. There is so much exciting innovation happening with blockchain, CRISPR, 3D printing, artificial intelligence, robotics, and space exploration that the idea of picking one problem and going heads down right now feels like I would miss too much. As a firm, we have deep conviction that we will have the most success (and fun) investing in companies that use breakthrough technologies to radically improve millions of lives.

Working with Jason at Oakhouse Partners feels like the next step in what will hopefully be a lifelong journey of finding fulfillment by making a difference. I am eager to meet, support, and learn from the entrepreneurs with the vision and capability to tackle critical missions using technology. I aspire to become the first phone call that an entrepreneur makes when facing the toughest challenges of their careers, as Jason was for me. That takes real trust and the effort required to foster it. I look forward to the challenge.

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