Outsiders [Sometimes] Make the Best Insiders, Part 2

By Attorneys Joe Boucher and Drew Coursin

In the first part of this post, we suggested that entrepreneurs look outside their own tightly-knit circles of founders and co-strugglers to include outside advisors in the startup process.  To recap, Part 1 contained the “Why”: outsiders bring experience, fresh perspective and, more often than not, excellent connections to the business community.  This Part 2 moves forward into the “How.”

As daunting as starting a business from scratch can be, there hasn’t been a time in recent memory when entrepreneurs had as many opportunities to connect with each other and – as it pertains to the thrust of this article – with more experienced members of the startup community.  Future captains of industry can organize, share ideas, validate business plans, and participate in the growth of their local (and regional and national and international and intergalactic [probably]) entrepreneurial communities with ease.  In many communities, it seems equally straightforward to connect with advisors and mentors.

Take Madison, Wisconsin, for example.  From an outsider’s perspective, Madison doesn’t look like a hub for entrepreneurial growth, with its relatively small population and flyover state location.  And yet, entrepreneurs in Madison have access to coworking spaces, startup accelerators and incubators, conferences/town halls/industry meetups over beer and cheese curds, and a world-class research institute.

At every turn, entrepreneurs at every stage, from great idea scrawled on a cocktail napkin to Series A financing and beyond, can and should avail themselves of the chance to connect meaningfully with their more experienced counterparts.  Early stage startups can look to local accelerators and mentor programs, but should also make an effort to attend conferences and networking events where they can start developing meaningful relationships with those who have come before.

The entrepreneurial community is often maligned as somewhat hyper-rugged individualist, but the truth is that it is a self-sustaining entity whose constituents really want to help the next generations of startups.  As in any community, relationships are the key to success, so the more founders can do to foster positive interaction with their peers and mentors (including, but not limited to, other entrepreneurs forged in the crucible of startup failure and success, venture capitalists and angel investors, professors and other academic advisors, and even professional service providers like accountants, bankers and *ahem* lawyers), the more likely it is they will thrive and grow.