Intelligent.ly, and why it mattered

This post was first published on Sunday in Dennis Keohane’s weekly Utterly Biased newsletter. To receive UB in the future, sign up here.

The memories from my first visit to Intelligent.ly are still quite vivid.

I remember the bold — at least in my opinion at the time — blues of the company logo hanging throughout the classroom, which contrasted with the various faded reds of the exposed brick space of the entire BzzAgent office that housed Intelligent.ly.

The space on Harrison Avenue was filled with the brightly colored — and oversized — paintings of Seth Minkin. Minkin served as Dave Balter’s “artist-in-residence” in the space. The former warehouse was also home to a wide array of companies. Not only were BzzAgent (Dunnhumby after the 2011 acquisition) and Intelligent.ly based there, but other organizations over the years like Dunnhumby Ventures, Promoboxx, HelpScout, and Smarterer called the office home. At one point, this writer, as VentureFizz’s unofficial Boston-based jack-of-all-trades, had a small desk in the space.

There were small bits of classic Balter/Hodges flair throughout Intelligent.ly’s classroom in the far back of the space. In addition to Minkin’s massive animal paintings, there was a smallish triceratops statue, various other random knick-knacks, a kitchen brimming with wine, and a fair amount of liquor — heavy on the tequila. When classes were in session, there was always copious amounts of Regina pizza, and what seemed like a never-ending supply of PBR.

I have no clue who spoke the first evening I went to Intelligent.ly — maybe then-Boundless CTO Aaron White, but I might be mistaken — but I do remember being quite nervous and eager to keep as low a profile as possible. Back then, which I think was the spring of 2012, I was an English teacher at a local private school with an inkling that it was time to transition careers.

I had grown interested in entrepreneurship and wanted to learn more about what it was like to start and run a small business. At the time, Intelligent.ly was the best resource to learn about that in an intimate yet casual setting.

At the session I attended, I tried to follow the presentation without drawing much notice. I feared I would somehow get outed as being a teacher — whose bosses would frown upon this moonlighting and career exploration — and, more generally, as a fraud.

While trying to maintain shaman-like invisibility, I learned enough that evening to be enchanted by the world of entrepreneurship, especially the Boston “innovation” community, as it has been referred to on and off over the years. (The use of this phrasing will be the focus of a future UB newsletter.)

But it wasn’t the presentation or the speaker that piqued my interest. It was the warmth of everyone bopping about the Intelligent.ly space — the hosts, the wallflowers, the attendees, the seemingly harried startup folks still working in BzzAgent or one of the other companies sharing the office at the time. It was so welcoming. There was a bright, light air to the evening, and, by extension, the possibility of becoming an entrepreneur in Boston in general.

This is no small feat. It was something inherent and unique to Intelligent.ly.

While the feelings I explain above are my own, I am sure many others have had similar experiences, whether in the old-school class format of Intelligent.ly or the more recent, leadership training iteration.

This experience helped stoke a passion that spring-boarded not only my career but my life to unimagined places.

With the news that Intelligent.ly is shutting down in 2018 delivered by Sarah Hodges on Medium last week, it’s important to acknowledge the role that the organization played not just in the growth of some businesses locally, but in the lives of many people, myself included.

Intelligent.ly was founded in 2012 by Dave Balter, who is currently a partner at Flipside Crypto, with current Pillar VC partner Sarah Hodges at the helm. Back then, Balter was leading BzzAgent post-acquisition, and Hodges was finishing up a successful stint running marketing for RunKeeper and about to move to Smarterer.

Last year, the two, a couple for the past few years, were married.

At the time it first opened, Intelligent.ly was compared to the co-working/learning space General Assembly in New York. Looking back, I’d say that’s not a very apt comparison. GA, in my mind, is more akin to The University of Phoenix, a great place to learn, if you are motivated. Intelligent.ly was something a bit different.

Intelligent.ly evolved over its history, but even in its earliest form, it made an impact on the individuals who attended its programming. Going to a class in those days was an adventure. It could lead to an introduction to a niche business topic, experience-based guidance on moving up the hierarchy of a small business, opportunities to meet and be mentored by those running some of Boston’s most successful companies, or, quite honestly, time to just meet and hang out with like-minded folks.

When programming first started — small, intimate classes and discussions at 500 Harrison — the focus was to serve as a conduit to bring those on the outside of Boston’s startup world to the inside. Founders, CEOs, engineers, product heads, HR managers, lawyers and the like would show up and dig into their prepared presentations for audiences that could include stay-at-home moms, college students, creatives, and a plethora of others seeking an education that couldn’t be found elsewhere in the city. More often than not, the sessions would conclude with lengthy Q&A periods. Sometimes there would be even longer, spontaneous post-event gatherings during which the speaker might mingle and answer questions from the audience.

I believe that many a key hire and many unexpected investment opportunities arose from these unplanned *salons*.

As some of Balter’s other projects expanded — most notably Smarterer, which was acquired by Pluralsight in 2014 — Intelligent.ly moved out of the South End and into different venues, including, the at-the-time Diane Hessan-led, Communispace, now known as C-Space. While classes still continued to fill up on a regular basis, in my observations, a lot of the vibrancy present in the “back” of BzzAgent was lost with the change.

In recent years, Intelligent.ly evolved into something quite different from its original format. The most recent model of the program sought to train individuals who had been identified as having the most promising leadership potential from a small cohort of local companies, like Dyn, DraftKings, etc. This version of Intelligent.ly filled a void for many of the small organizations who didn’t have the time, or wherewithal, to develop its next generation of leaders. Many of the companies and people that I have spoken to who went through the program, had nothing but positive things to say about the experience.

The reasons for the Intelligent.ly’s evolution over the past five years has a bit to do with finances, as more consistent revenue is available when developing a curriculum and partnering with corporate entities to educate their workforce than to rely on individuals to sign-up for entrepreneurship classes.

You could also see in Intelligent.ly’s growth arc and ultimate end a potentially dire trend for the Greater Boston area’s long prominence in developing innovative companies and the creative individuals who build, run, and staff these organizations. But that is a story for another day.

Like most tech and innovation projects, Intelligent.ly isn’t immune from some criticism as well.

While overall, the organization made an enormous impact on many people and small local companies — I think it was an ideal place for people making career changes into the startup world — one could argue that it didn’t do enough to bridge the minority communities around Boston with the startup ecosystem. While this flaw is something many are still trying to figure out, I must say that Intelligent.ly was far ahead of the curve in welcoming and giving opportunities to women to position themselves in more prominent roles in various industries across the city.

Also, it can be said that one of Intelligent.ly’s greatest assets, its clubhouse-like environment early on, could also have been seen as too insider for some. It is a quintessentially Bostonian trait to perceive an insider/outsider dichotomy in almost every social or business collegiality, so I don’t put too much stock in those who viewed Intelligent.ly in this light.

What it comes down to is that over five years Intelligent.ly played an influential role in the city’s business landscape and helped advance the careers of many in Boston.

Personally, I will miss Intelligent.ly deeply.

Many great memories that stand out from my own experiences.

Watching HubSpot CTO and co-founder Dharmesh Shah work through a presentation on “Inbound Marketing for Entrepreneurs,” was revelatoryfor me. I didn’t know that someone with such business acumen could also be witty, inspirational, and candid at once.

I met people at Intelligent.ly whom I now consider to be vital and treasured friends and confidants, including Balter, Hodges, JessMeetKen’s Ken Deckinger, and HubSpot’s Katie Burke, among others. This alone causes pangs of sorrow for those who won’t be able to make similar deep connections in the absence of Intelligent.ly.

I still have people, many of whom have established their own incredible careers, who come up to me and thank me for the Intelligent.ly class I taught on making career changes (which just happened to be the same evening the Red Sox clinched the World Series at Fenway in 2013). The impact that sharing your own story can have on others is a lesson I am grateful to have been able to have learned with the help of Intelligent.ly.

More than anything, the Intelligent.ly that will live on in my mind is the casual conversations, usually over a beer, that delved into topics, both erudite and sophomoric, that actually could change the way one sees the world and the potential for one’s place in it.

The landscape of Boston’s “innovation” community has changed rapidly over the past few years, so quick, it may seem, that we don’t realize that a unique era may have ended or be fading.

The key attribute of this period — with organizations like MassChallenge, Bostinno, Techstars, Startup School, and the like thriving; HubSpot and Wayfair, among others, successfully going public; young founders shooting for the moon; and venture money widely accessible — may be the sheer audacity of the key players and the yearning to ignite passion or change from those running businesses and organizations.

Intelligent.ly was the keystone of that period. Although it may come back in some other form, I am thankful to have experienced the organization in its prime.

Utterly Biased and Boston’s Next “Clubhouse”

Thinking about Intelligent.ly for the past week, what stood out in my mind is the welcoming environment Balter, Hodges, and crew created with the program.

To my mind, this is something that has been lacking in Boston the past few years.

As Utterly Biased returns in 2018, there are going to be some changes, all of them for the better I hope. One thing I aim to do is replicate what I loved about Intelligent.ly’s early days: A laid back, supportive community.

Next week I’ll lay out some more details about what this looks like, but I just wanted to share that I am really excited about the next phase of Utterly Biased.

Thanks for being along for the ride.

-D

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