Why I joined Path 101

As Charlie announced on the Path101 blog, I’ve joined his angel round as an investor and will be taking a seat on their Board of Directors (me, Charlie and his co-founder CTO Alex). Path101 is aimed at providing professional career advice with a combination of community, data analysis and personality assessment tools. The company is being developed in “uber anti-stealth” mode, so, in that spirit, here’s my thinking behind getting involved.

1) It’s a bet on Charlie

  • Charlie’s a phenomenal guy who follows his passions and I believe that longterm he’ll succeed. He and I met online because of the mutual interests expressed in our blogs (if not always in our Last.fm profiles). Since then we’ve had several casual conversations which escalated once he decided to start Path101.
  • I’m buying into Charlie early in order to continue building this relationship. Path101 is a good concept with merit (see #2) but my involvement here is also about a set of broader opportunities with Charlie and his projects going forward. I’m “going long” on Charlie O’Donnell.

2) It deserves to exist

  • People making better, more fulfilling career choices – i’d like to help that happen so I’m investing some expertise and a small amount of money. Projects that excite me tend to have both heart and mind — merit and value — I care less about “yet another ” and more about seeing products come to fruition that help people in one form or another.

3) My personal growth and skill development

  • Becoming a board member with Path 101 provides the opportunity to further develop my persona as an advisor, Director and investor – roles that i plan to increasingly take on in the coming years.
  • After participating in many board meetings at Second Life, this is a chance to learn about managing the process from the other side, a skill I’ll need when I return to start-up life post-Google.
  • Most of Charlie’s investors are NYC-based, an area where my tech/VC network isn’t as deep as in the Bay Area. Co-investing with these folks gives me a) increased diversity of ideas and b) some insights into their community in case I ever end up back East.

And so it begins….