Do You Know the 5 Biggest Mistakes to Avoid!

Authenticity, Asymmetry and Making a Connection with Investors with Sean O'Brien

Sean O’Brien,  is Co-Founder and Managing Partner of Overline, an Atlanta-based seed-stage venture capital fund that he runs with his partner, Michael Cohn. 

Sean has been in the investment business for nearly 30 years, with roles in investment banking, hedge fund management, corporate development and venture capital. 

He is an All-Star Mentor in the Techstars network, a mentor in the Endeavor network, and an advisor to a number of startups. 

Sean received his degree from NYU and lives in the Atlanta area with his wife and twin daughters. 


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In this episode…

Sean talks about asymmetry and if the gap is really that wide?  He shares how he knows it is inherently unnatural for those looking for funding to sell themselves and their vision. 

When people are making their pitch, it is painful to watch as he knows the anxiety they are feeling and being terrified to make the ask.

Sean is a big fan of authenticity - people need to just be themselves and trust in them and the process.  They aren’t looking for a performance and are more interested in their story, not someone who is salesy or a know-it-all.  Humility is key.

Rather than the “fake it until you make it” mentality, they want to hear, “I don’t know” or “Will you explain that to me?”

Sean feels it is refreshing with the modernization of the funding world in seeing success not only through the eyes of a spreadsheet and numbers.

Pattern recognition is important when talking to investors, and founders don’t always do their homework.  They need to learn about whom they are pitching too and follow the patterns.

A tip for fundraising: adopt a process and be intentional about it.  However, most people have a huge miss and that’s the ask.

He likes to hear, “This is what I’m building, here is what I think, and this is my structure.”

Those seeking funding should know what they think they need but also be open to hearing thoughts and advice.  

Sean and Michael want to be the first one called for celebrations, bad news, good news and a couch session when a mental break is needed.  

How quickly people recover is crucial!

Sean states he is really bad at saying no, and is intellectually curious in what everyone has to pitch.  He feels an obligation and responsibility toward diversity.

He has a simple intake form on his website for those who are interested, but is sticking close to Atlanta and the SE.

Resources Mentioned in this episode

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