Philly Startup Leaders is dealing with an Identity Crisis

By Alex Hillman on Wednesday, September 14th, 2011 in Community, philadelphia with 12 Comments

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.

  • http://twitter.com/phil_ives Philip Ives

    This post was great, it keyed off some of my own thoughts : http://phil-ives.posterous.com/the-psl-fishbowl

  • http://twitter.com/gloriabell Gloria Bell

    Alex and Phil, since you obviously have such strong opinions on the direction that PSL and this community should take, it would have been nice to have you as part of last night’s conversation and see you more actively participating in the organization. 

  • http://www.dangerouslyawesome.com alexknowshtml

    Thanks Phil.

    I was with you until this part:

    It should be reaching out to the GameLab and Tech meetups and helping them and being a larger umbrella for what’s going on here.

    I’ve seen this pattern before, and it reminds me WAY too much of another organization that went belly up because it didn’t have an identity of its own.

    The reality is, the Philly story is still an ever-increasing story of hope. PSL served its purpose. It either evolves to re-imagine its own identity, or people move on. It’s happened before, it will happen again.

  • http://www.dangerouslyawesome.com alexknowshtml

    I was once quite active in PSL, moreso than most. I never held a board position. But apart from attending events, as I mentioned, I was asked to join the advisory board and did so even though I had concerns from the onset about my participation. Beyond the single group advisory call that ever happened, I spoke privately with many members of the board and the community, and both former presidents. In particular, I had a very hopeful conversation with Jameson right when he took office. I am particularly disappointed that he never fulfilled his goals and became a casualty of his own story.

    I’ve also fielded a number of inquiries in the last year about what could be done to improve things, from people who themselves believed things had become unhinged and they wanted to help. Some took that back to PSL. Others decided to take things into their own hands and start new initiatives, out of similar frustration to me.

    I tried, believe me. And in spite of what you’re probably reacting to as a critical post, I wouldn’t be writing about this if I didn’t care. I don’t waste time on things I don’t care about.

    At the end, I unsubscribed from the listserv some time ago after coming to terms with the fact that I was overall unsatisfied with the results of my participation.  

    From the sounds of the discussion last night, I might just have been ahead of the curve. 

    Frankly, I planned on attending last night. Something in my personal life led me to decide that my time was better spent with a person who I care about. In reading through the comments and discussion that made it to the public forums, I’m fairly confident I would have just left more frustrated, and this post would’ve been one of disappointment rather than one of hope.

    Please realize that: this post is critical, but if you step outside of yourself for a moment, you’ll realize that the overall story is a very positive one for Philadelphia. That’s the only story that matters. 

  • http://twitter.com/phil_ives Philip Ives

    It’s probably said a better way. but I think there is a need and a want for an organization that liaises between the ecosystem in Philadelphia and outside it. I’m not saying PSL should be that, only that it COULD be that. 

  • http://www.facebook.com/mattmonihan Matt Monihan

    I’ve been to a couple PSL events as of late, and they mostly struck me as the same as any networking group. The event will have a speaker, who may or may not be interesting or relevant; there’s some free food, and maybe I’ll strike up a conversation with the person next to me where we both pitch our company/idea to a brick wall.

    Sometimes there’s a speaker that really inspires you, and sometimes you talk to someone in the community that you can help/can help you.

    It seems to me that this isn’t really a PSL problem as much as it is an “organized group capacity” problem. When the ratio of interested to practicing goes up, all of the practicing people will start to move on to the next thing, or just lose interest entirely.

    The reason I want things like PSL to exist is to have a place where I can go to meet new people, but also, almost more importantly, to meet up with people I recognize from the community as leaders. These people I may not know closely, but are consistent in their participation, and I can count on them to, well, lead. The problem here is that these types of people show up and don’t gain much from the group. There needs to be a bilateral transfer of value if you want to retain real leaders.

    One way this could be achieved is to identify some members of the community as leaders. Have some kind of criteria that has to be met to be deemed a “leader.” And when you become a leader, there should be some responsibility to justify your title by presenting what you have done to help the community at each meeting. This could be difficult to pull off, but pretty awesome if they did. The key is honing in on what the real leaders want and making sure they derive value from the community.

    …Also, n00bs must wear hats designating them as such.

  • http://www.dangerouslyawesome.com alexknowshtml

    Perhaps. I still think it needs a strong identity of its own before it’s running around helping others. Otherwise we’ll just be ending up with more of the same.

  • http://www.dangerouslyawesome.com alexknowshtml

    Totally agreed on the “this isn’t unique to PSL” point. This is a common pattern, hence pointing out the SXSW example. I can think of many other places this became a problem.

    I also agree that the value proposition is mismatched. I’ve classified this as an imbalance between “has” and “needs”. The PSL community members, as you point out, tend to have far less to give than they need to take. This is the nature of starting an early stage company. This rears its head in the struggle for event volunteers as well. People want, but don’t have to give…yet. This disenfranchises supporters (as I did with me), and will continue to until the balance begins to return.

    This is one of the reasons we’re careful not to include job board materials or help recruiters at Indy Hall. When Indy Hall becomes a place where people expect that they can get work – instead of get work DONE – our has/needs balance is disrupted.

    On the converse, we work to actively help members help themselves. Our successful members lead new members by example, and new members learn that contributions are rewarded with praise and kudos from other community members – not praise and kudos from me. It happens very naturally, and as such, is sustainable. No extrinsic motivators necessary.

    The problem with your “nametag” solution is that it’s more of the same. Who’s a leader, and to whom? Even presenting your work is subjective. And then there’s the measure of motivation – are they leading to get the nametag and be deemed a leader by the self-designated leaders, or because simply because they are leaders? 

    The best leaders I know of in Philadelphia are reluctant leaders, quiet leaders, who’d never wear a badge if you gave it to them. We don’t need more people scrambling for “leader” nametags. You can see where that got us this time.

  • http://www.dangerouslyawesome.com alexknowshtml

    Also – n00b hats = best idea.

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