CatskillsConf: Fun mashup helps build startup community

Just came off a very fun and worthwhile weekend at the inaugural CatskillsConf – a three day affair that brought together an eclectic mix of creatives, tech people, foodies and startup community supporters.

Was cool not only because the organizers were able to successfully pull off marketing to assemble 120+ people that touched on all those themes, but the diversity included an audience nearly evenly split between Upstate and NY metro.

This was the first ever such gathering in the Hudson Valley/Catskills area. It came about after founders of the Hudson Valley Tech Meetup (Dan Stone, Daniel and Sabrina Shutzsmith and Kale Kaposhilin) met Aaron Quint, (web entrepreneur and former Paperless Post CTO/Chief Scientist) who recently transplanted from NYC to the Hudson Valley.

Pooling their combined organizational talents, passion for bringing people together and lists of contacts is what catalyzed CatskillsConf and their joint marketing outreach filled the room.

Leveraging Local Assets

Whether it was musical talent, farm to table culinary, wood crafts and natural settings of the Ashokan Center, this was a thoughtful mashup that brought diverse elements together with common themes that spoke to the millennial target.

On the learning side, my personal favorites were Dennis Crowley’s “put it all out there” story reflecting struggles at different stages in the startup journey, and also an amazing education segment featuring live birds of prey doing their thing.

birds of prey

When you’ve got a group together for more than a day, it gives opportunity to go beyond a large group learning setting to do some things that can be hands on, fun and social – all adding to the potential of building on strong relationships among participants.

The Catskills flavor for small group activities included options like foraging, blacksmithing, cider making, bookbinding, and drone piloting to name just a few.

Institutional ownership not a requirement for success

More than just a well run event, what’s unusual here is that the outcome wasn’t oriented towards benefiting a particular organization – but rather to just grow the relationship networks for participants, while having a fun time and creating many memories.

My boomer generation just isn’t used to seeing grass roots organizing like this without institutional ownership and resources.

New relationships will yield downstream benefit

As I browsed around, a frequent comment from local tech people sounded like “I used to think I was the only person around here like me. As a result of the groups forming and events bringing like minded people together, I’ve now got a growing network of supporters to help me.”

As I try to calculate the number of “creative collisions” that occurred and what happens when like minded people stumble into each other for the first time, there is little doubt that startup formation and growth will include some life changing outcomes sparked by what seemed like chance encounters.

Good things happen when a few people step up to lead

Kudos to the organizers as they took financial risk and put in a ton of hours along with a full supporting team of volunteers.

They set an inspiring standard for others to follow and their leadership adds further fuel to my optimism about why it is the millennials who are making the difference in powering Upstate towards a big jump in the number of new industry companies and jobs that will rise here from humble beginnings as people meeting at an event that then lead to collaborating on a startup.

We pledge our resources at Upstate Venture Connect to support their efforts and look forward to doing the same for all others ready to lead the charge in their own local market.


Confidence and humility are not mutually exclusive

As I meet entrepreneurs seeking to launch their first startup, I’ve begun noticing behavioral traits I wasn’t paying much attention to before.

Signals I’m picking up more frequently are from entrepreneurs coming across as super confident (even aggressive), perhaps in an effort to show they are hard driving and ambitious.

While confidence in one’s beliefs is indeed a critical asset for a startup entrepreneur, my BS detector begins kicking in when I see a total absence of humility. The tells are things like:

– working their accomplishments into the conversation
– no hint of what they don’t yet know or are seeking to learn
– expressing no curiosity about whom they’re interacting with
– interactions appear motivated only by potential self interest – no evidence of “pay it forward”
– how they interact with others who serve or bump into them seems different than their style of interacting with those in a professional context

Because I’m an investor who looks hard at leadership qualities of the CEOs I want to work with, my mind gravitates towards thinking: “If this is what I’m noticing now, I wonder how it translates to future interactions this entrepreneur has with others they seek to recruit and lead?”

Humility as a leadership trait

If you’re looking for thoughtful insights backing up the quality of humility in leaders, check out Jim Collins’ Good To Great and his work profiling Level V leaders. His research supports the thesis that CEOs embodying the unusual combination of fierce resolve and personal humility ended up being a critical leadership trait for top performing companies in the study.

My own view was shaped most by my Dad and my wife Krista, but also the good fortune of having close contact with a bunch of exceptionally strong leaders who personify humility in how they lead and interact with whomever they meet.

Jack Stack, Founder/CEO of SRC and visionary behind the Great Game of Business would certainly top my list in exemplifying resolute commitment and personal humility. SRC is not only a phenomenally successful company that has transformed thousands of lives, but beyond Jack’s Southern gentleman’s humble style, his open sourcing of the GGOB and open book management practices empower a generation of entrepreneurs like me to embrace principles around getting everyone in a company to think and act like owners – the ultimate management humility as it means running an organization with the power bubbling from the bottom up.

Back in 1995, Anthony Martin, now retired Chairman/CEO of global staffing giant Select (and subsequently Vedior) picked TriNet to invest as one of the 40+ companies in his portfolio. Much to my benefit, he traveled “across the pond” for 10+ years to sit on TriNet’s Board of Directors. Soft spoken with never a wasted word, his gracious, gentle, almost patrician manner helped set the tone for our board meetings with wisdom that came through penetrating observations and questions that were so much more effective than the contrasting style of boards featuring competition to demonstrate who is the smartest guy in the room.

In the emerging tech world, anyone that knows or interacts with uber VC Brad Feld (@bfeld) will attest he gives so much of himself to so many causes (building entrepreneurial ecosystems, women in tech, computer science education and entrepreneurship globally to name just a few) and notwithstanding an incredibly packed and productive schedule and contact list, still shows an uncommon curiosity and willingness to pay it forward with each new person he bumps into.

Humble, super successful people stand out

So I take notice when I encounter a super successful person who isn’t showing the expected trait of being the center of attention in a dialogue among a small group.

My respect grows as they instead show curiosity in others and demonstrate care and concern for people they don’t know, as well as how they contribute talent towards things not driven by self interest.

Encounters like these also reinforce my not losing sight of humility in what I say and do.

Paying it forward is going to be a theme I hope to keep shining more light on. Not only to help keep me centered, but also my belief that raising awareness of success beyond financial measures is the real story behind entrepreneurs with the most impact.