I wasn’t in the room for the conversation and breakout groups, but PSL held it’s reboot “fishbowl” last night.

Reading through all of the comments, and then TechnicallyPhilly’s redux, one thing is clear to me:

PSL has an identity crisis, and fragmentation is inevitable.

It feels familiar, though, and isn’t necessarily a bad thing.

Rather than try to identify the various identities in play, which I guarantee would offend somebody, I’m thinking more about the inevitable results and what they mean for this organization as well as Philadelphia.

Back in the spring, I wrote about how SXSW has an identity crisis.

In that post, I pointed to two distinct events: a conference, which had grown by orders of magnitude and largely lost a discernible identity – becoming a destination for designers, developers, marketers, social media types, VCs, startups…anybody on the web, essentially. Then there’s the festival – the gathering of humans, resembling a spring break, where it didn’t MATTER what industry we affiliated with. We enjoyed our each others’ company and celebrated the fact that we worked on the web. Last year, I left the conference behind and instead spent more time seeking the festival – the people of SXSW – and focusing on quality time with them.

My SXSW ’11 experience was profoundly different this way. Positively different.

I think PSL is suffering a similar fate. It boasts a 1000+ member listserv. Most of those members don’t know why they are there, or why anybody else is there. PSL has evolved from a community of practice into a community of interest. Most of the real leaders are people are on the fringe of PSL, only a few are still active in the heart. Most new members of PSL, like new SXSW attendees, don’t know to look to the fringe for the people – most specifically the mentors – that they really seek. They never make it past the talking heads, or know that they’re supposed to.

SXSW struggled culturally for a few years by trying to hold on too tightly to things they didn’t know how to control, and in some cases, couldn’t control if they wanted to. PSL has done the same. In both cases, fragmentation became inevitable.

The way each chooses to deal with fragmentation is the difference between success and failure.

For me, the question is: do you continue to MAKE the fragmentation it happen, creating chaos and damage within the ecosystem along the way? Or do you LET it happen, understanding the stress fractures and working to make any losses sustainable?

With fragmentation, comes a renewal of focus. Focus that PSL seems to want and need.

On Mentorship

I was on the PSL advisory board back in the summer of 2009. On an advisory call, I made it clear what I thought should be PSL’s primary mission: to help create the currently missing “senior generation” of hi-tech business leaders that our city is missing, so that it might be available for the next generation. The focus on mentorship seems to have come up in last night’s fishbowl too, but with the wrong focus. The focus was on incentivizing mentors. Or worse, trying to force mentorship from PSL members.

Being a mentor isn’t necessarily the active state of “mentoring” that incubators, accelerators, and the startup tabloids would have you think. Mentoring is rooted in the act of leading by example. People who coach without doing the things that they coach are just that – coaches – but they aren’t mentors.

Chris Bartlett has an amazing take on this. He encourages “secret mentorship”. It’s a humbler approach to mentorship. It happens two ways:

1. You can pick somebody to mentor, but don’t tell them you are mentoring them. This challenges you to show them how to do things rather than just tell them. It pushes you to guide them without forcing them.
2. You can pick somebody to be your mentor, but don’t tell them that they are mentoring you. This challenges you to synthesize from their actions. It forces you to learn instead of just replicate.

If PSL wants to get serious about being an engine to create and encourage mentorship in Philadelphia, I think it’s going to need to figure out a way to dodge the ego-driven “leaders” that the process is inevitably going to attract and instead, be laser-focused on helping create opportunities for acts of secret mentorship.

I don’t know if that’s the Philly Startup Leaders that the “leaders” decide to rebuild, but that’s the Philly Startup Leaders that Philly needs.

Then again, if they don’t build that, I’m not worried. Others have already started down that path in their place.