How to Mentor So That It Means Something


There’s something magical happening in Boston right now, and it’s going to make history. Like many startup scenes, Boston’s is truly exploding, vibrant with passionate founders and bold teams, backed by a fresh crop of seed funds and experienced venture capitalists. But this isn’t merely a rehash of the late ’90s or early 2000s. This is something entirely different.

Beginning in 2011, Boston’s ecosystem started to deeply interconnect—like some massive neural network—and it’s now on the precipice of becoming one of the greatest startup organisms ever created. The reason for this is simple: this organism is nurturing, embracing, and considerate of its entire being. The startup system has bucked convention in a city where people don’t make eye contact on the T, and a honk and the finger is all part of the morning commute. What was once an environment of competition and posturing has been replaced by one of cultivation and brotherhood.

The momentum that’s bringing us into 2012 is irrefutable. Everywhere you turn new nodes are being created and synapses are firing. We’re seeing a similar trend in cities around the country like Salt Lake City, Austin, Las Vegas, and New York City. But even with all of the wonderful things happening in these cities, there’s a very real danger that we could miss the multi-billion dollar opportunity that lies in front of us. That’s because this interconnectivity is merely the beginning.  What will make or break 2012 isn’t the validity of the ideas created, the energy of the founders, or the willingness for capital to be deployed. Individuals will make the difference—entrepreneurs and mentors alike—by proactively fostering and enabling results through two specific activities:

1. SpiderWeb Mentorship: Successful entrepreneurs and executives actively pushing people up and into the ecosystem.

2. Horizontal Entrepreneurism: Collaboration across companies, with entrepreneurs enthusiastically supporting each other.

In the case of Horizontal Entrepreneurism, Boston is rife with examples: Workvibe profiling local startups to draw in new talent, #RubyRiot encouraging community members to “pay it forward”; BzzAgent offering office space to startups such as Runkeeper, the first company to take advantage of the opportunity in 2009.

But a horizontally-focused entrepreneur ecosystem also runs a very dangerous risk: It can turn into something like a startup high school “clique”. There are those on the inside, and then those who are unknown, disconnected, and unintentionally undermined. Whether Boston has splintered into its own “Heathers” vs. Everyone Else environment is up for debate, but what’s critical now is to consciously avoid this trap and to take specific actions that ensure we continue to grow our startup scene and not shatter it.

That brings us to SpiderWeb Mentorship, the determining factor in whether or not a startup ecosystem splinters and cliques—or becomes robust enough to optimize the likelihood for companies to thrive and succeed.

SpiderWeb Mentorship is about creating the strongest startup “web” possible, by weaving an incredible tapestry of ideas and connections, allowing for random new offshoots, connecting divided webs, and oscillating the whole entrepreneurial ecosystem into action.

This occurs when experienced veterans (Mentors) focus not on making each individual entrepreneur better, but on making the system as a whole stronger. Mentors must be open and willing to (a) connect with people beyond only those with the right “credentials” and (b) focus on the development of “web-like” interconnectivity to other mentors and other entrepreneurs. This can be accomplished by Mentors actively engaging in a set of critical behaviors:

1) Take the Unknown Meetings with Ambiguous Agendas. Regardless of someone’s experience or who they know, SpiderWeb Mentors connect with people who reach out to them, to create new connective threads. The strongest Mentors are willing to take a meeting, just to listen and share, with no specific agenda. We both have SpiderWeb Mentors to thank for starting our own careers.

2) Follow the Law of Three Introductions. Once you meet with an entrepreneur, it’s key that they are introduced to at least three others—2 active/known entrepreneurs and 1 mentor—to create more connections across the horizontal entrepreneur web.

3) Be Constructive—and Critical. It’s key to push each other to grow and improve. While it is important to celebrate and talk about the wins, cheerleading alone will not ensure business success. As they say: If you see something, say something.

4) If you’re a Big Spider, Show Up! Executives at mature companies need to engage with the community. You big guys know who you are and you have a lot of knowledge to share. This is one of the best ways for you to give back.

5) Start Your Own Web. Have the initiative to take charge, reach out, and speak up. As the Mentor it’s up to you to activate the web. Get involved with the universities, sit on panels, hold open office hours. Whatever it takes, make yourself available.

So, this is a call to every Startup City, to inspire their entrepreneurs and mentors to do the work. To protect ourselves against the one virus that can take us down: the failure to support each other. We need to go out of our way to make it happen. SpiderWeb Mentorship and Horizontal Entrepreneurism are the keys to ensuring our organism thrives and survives.

This is the moment. Let’s weave the web, people!

[This post also appears in Inc. Magazine—Eds.]

Dave Balter is the CEO of BzzAgent (a dunnhumby company). Jennifer Lum is the co-founder of Apricot Capital. Follow @

Trending on Xconomy