Two Entrepreneurs Walk into a Bar….

March 19, 2020

Two Entrepreneurs Walk into a Bar…

A Baby Boomer and a Millennial walk into a bar…ok, not a bar, but onto my Zoom screen on separate occasions over the past couple weeks. Despite the 30+ year difference in their ages, they share a number of similarities: They’re both White, hetero men. Each, in his own way, is fascinatingly intelligent and meticulously self-educated on a wide range of topics from economics to politics, history, financial markets, permaculture, governmental systems, cryptocurrency, and more. Both speak dynamically, passionately, and articulately — and presumably ad infinitum, if one doesn’t cut them off — about their vision. And each of them has a highly ambitious, intricately detailed, and multi-faceted vision for bringing positive social change to the world.

They found me through different channels. The Boomer heard me speak on a webinar about Community Investment Funds and contacted me afterward for a meeting; the Millennial found me through LinkedIn and YouTube. The latter requested a meeting specifically to provide advice and guidance on how to seek capital for his venture. The former…well, I’m still not sure exactly what he wanted of me, and here is where we start to see some key differences between the two.

As I intimated above, both men were prone to talking passionately yet unabatedly about their vision. I played a part, of course, in their meandering monologue by allowing them to ramble without (much) interruption, mostly because I found their subjects interesting, but also because I tend to learn a lot from observation. I’m a bit of an introvert and, as such, I’m comfortable remaining quiet but attentive as I listen in order to truly hear and understand. This means engaging more than my ears; using my eyes to observe body language and other visual clues. I also have a curiosity to observe a person’s sense of self-awareness in (what is supposed to be) a conversation and manifests as self-regulation and an openness to dialogue and discussion.

In my Zoom meetings with each entrepreneur, I discovered a significant variance in self-regulation and openness to discussion, which is not only interesting from a generational comparison but, I believe, also an indication of their potential success as entrepreneurs. As an entrepreneur myself, I have been in these guys’ shoes many times before, having to communicate my vision to potential investors, grant-makers, partners, employees, or customers in order to get a business up and running. It takes more than a polished, ambitious, and passionate pitch.

Communicating one’s vision also requires clarity, focus, and a solid strategic plan.

 From my two Zoom-mates, who unraveled their respective ideas during calls that went way over the scheduled time limit, I discovered visions that were so complex, multi-layered, and lacking in structure as to appear kaleidoscopic. They had so many moving parts that one tiny shift would change the whole picture. On top of that, the collection of concepts was becoming increasingly unstable as more pieces continued to be added. Maybe “house of cards” is a more appropriate metaphor?

There is nothing inherently wrong with having a big audacious vision for broad systemic change as long as you have a well thought out, rational, and fundable strategic plan to implement that vision. What happens often with entrepreneurs, and certainly in the case of my two new friends, is something I call the ”ooh shiny” syndrome. It refers to the entrepreneur who, in the midst of developing their vision, discovers something tangentially related to their original idea and then latches on to this new shiny object before fully actualizing their original concept. It’s a very common thing among entrepreneurs, almost part of our nature, and it’s part of what makes successful entrepreneurs able to pivot toward a modified solution when their original vision hits a snag. But if allowed to run unchecked, the ooh shiny syndrome can be debilitating as the original spark of an idea gains so many add-ons and nuances that it becomes too cumbersome to launch. And if the entrepreneur happens to have a team, ooh shiny syndrome can lead to inefficiencies, frustration, and burn-out as team members are whiplashed into chasing down the latest and greatest idea without clear direction or the satisfaction of ever achieving tangible results.

Ooh shiny syndrome was clearly having its way with the Boomer and the Millennial. Their original visions — and some of the add-ons — have merit and I can see a potential market need in both their cases. But after listening to them describe their ponderous plans in a delivery akin to an infomercial — but wait, there’s more! —  I finally had to jump in and ask, “So what’s the next step? What’s your strategic plan for rolling this out? What’s the revenue model? Where will you find the money to launch and grow?” The different reactions to this line of questioning from the two entrepreneurs was intriguing and telling.

With the Millennial, my questions gave him pause. They stopped him in his tracks and made him think, question, and consider that maybe he was indeed losing his way in the labyrinth of ideas he’d constructed. My advice to him was to focus, prioritize, and simplify. This advice was not only acknowledged, but, I believe, even appreciated. We talked about boiling down his plan to a one-page business model canvas, a framework with which he was already familiar. By the end of the call, I distinctly sensed his excitement to channel his considerable energy toward this last-but-crucial stage of work that would prepare his vision for launch.

The Boomer was an entirely different story. As I pursued my line of questions that politely challenged some assumptions while also trying to discover anything that might resemble a strategic plan for launch, I was met with increasing pushback and frustration. Despite my assertion that my questions were posed in the spirit of helping to make his plan focused and stronger, I got the sense that my input was unwelcome. I can only guess that what he really wanted was my tacit agreement with the plan, and an immediate request to jump on board with his team. I may never know the answer because the call ended rather abruptly and I don’t anticipate I’ll hear from him again.

So, what’s going on here? Is it purely a generational thing? I’m Gen X and thus younger than the guy who dismissed my feedback, and older than the one who appreciated it, so there certainly could be some kind of “age thing” happening. There could also be some gender bias issues wrapped up in generational stereotypes. I’m actually quite interested in intergenerational dynamics but not expert enough to give cogent analysis here, and besides, that’s not my point.

My point is about entrepreneurs and their ability to get an idea out of their heads and into action. In fact, unless you have taken concrete steps to bring your vision into reality, you are not yet an entrepreneur. You’re not even really a visionary. You’re a dreamer. There’s nothing wrong with having a dream — therein lie the seeds of innovation, after all — but at some point, you have to recognize that you’ve got something viable and GO TRY IT. Set some goals and metrics, define the steps that will take you toward your goal, identify the resources you need, and then take the leap. Take an informed and calculated leap, yes, but leap nonetheless.

Some find this part scary — whether they admit it or not — and stay happily ensconced in their dream world, further refining their plan and piling on ever more bells and whistles. These are the terminal cases of ooh shiny syndrome. One thing that can save them is a committed, action-oriented partner who takes over the helm to bring the vision into being. This can be a very powerful combination, by the way.

A balanced partnership of vision and action is the dynamic duo of the entrepreneurial world.

For others, the implementation phase is just as exciting as the ideation. These are the true visionaries because they take an idea, put it into action, learn from it, adapt, and keep innovating toward success. It takes courage. It takes an acceptance that an idea — and its corresponding plan — will never be perfect, but can be good enough to get started. It takes faith that you have the creativity, agility, stamina, and strength to deal with setbacks when they arise, and oh, they will. And it takes humility and self-awareness to accept support, guidance, and perspective from others because that’s how good ideas are made great.

So…a Boomer and a Millennial walk into a bar. They sit at opposite ends of the bar, order a beer, and start telling the stranger next to them about their great idea. A group of Gen X-ers overhears both conversations, talks among themselves, and then calls the Boomer and Millennial over to their table. They’ve pooled together $100,000 and offer it to the one who can convincingly deliver his pitch in two minutes or less. One entrepreneur immediately goes into bargaining mode to get a separate, longer meeting in private. The Gen X-ers return blank stares. The other entrepreneur takes a step forward and says, “Start the clock.” At the end of two minutes, he’s invited to sit down at the table, a round of beers is ordered, and a new partnership has begun. Which generation was the winner? Doesn’t matter. It was the one who took the leap.