Views from the Sixteen

349 days to go until my deadline.

In these first 16 days, I haven’t written much about the progress of my business venture. That’s partly because I don’t think you want to hear me repeatedly extol the virtues of wearing sweatpants to work (it’s…exactly as good as you think) and partly because I’ve been pushing to get a bit of groundwork done before speaking openly about what The Big Idea looks like in real life. If I were to hit a major roadblock in these very early days that forced me to change course, better that I not have laid out a big hypothetical blueprint from which I’d then need to do a lot of backpedaling. Having said that, I’m happy to report that – so far – I’ve hit no such roadblocks.

At this point, it occurs to me that this post could go one of two ways: here in my kitchen, hunched over my keyboard, I’ve debated between recapping some of the very specific ways in which I’ve been spending my time and, alternatively, focusing on my broader observations from these first couple of weeks. I settled on the latter because, for today, that’s what seems to be flowing more naturally. The former will follow at some future date, I’m sure.


Before I dive into those observations, though, I think it might be helpful to establish a bit of context as to the precise nature of the company I’m working to build.

I don’t intend, at any point, to spend a lot of time talking about those particulars because I don’t want this site to come off like an advertisement. Once I have a functioning website for my company (soon, hopefully), I will note it here for anyone who’d like to learn more. Any specific questions about the product or business model should have their answers there. Other than that, the content of this blog will be limited to anecdotes incidental to my work on the business, or to reflection on the grand philosophical objectives of the venture, since – pretty simply – my retelling of those things and the state of mind that goes with them are what I think I’ll want to look back on, down the road.

For now, while I don’t yet have a functioning website to direct you to, I will give you the gist of the venture by saying that it pertains to financial services and that the basic product on offer will be by no means revolutionary. If there’s one key thing I’ve learned over the years about what it means to be an entrepreneur (a label I hope to one day be worthy of), it’s that businesses do not need to invent a new product in order to be successful. What’s more important is offering a product that you feel you can deliver somehow better than the competition.

So, yeah. Surprise, surprise: I’ve spent my entire career in the financial-services industry and that’s where I’ll focus my efforts. This, for reasons of qualification, expertise and observations of what I believe can be done “better” (not to mention the great opportunity that I believe exists for non-profits in this sector).



While, as I mentioned, I’ve encountered no major roadblocks in my venture so far, I have come up against various instances of a few different types of, let’s say, headwinds. (“Headwinds” takes us dangerously close to the territory of dreaded corporate-speak, but I’m keeping it – grudgingly – because it works better than “speed bumps” or anything else I could come up with.)

For starers, there have been a handful of minor setbacks: events or realizations that represent real, if not major, impediments to progress. In the two examples I’ve written about, the modesty of available grant funding and the fact that I won’t be able to hire everyone I want to (when the time comes) are genuine challenges that do have a real chance of slowing me down. That doesn’t mean that I’m immediately accepting any sub-optimal fate (I’ll do my best to find the best solutions to these setbacks); only that these challenges are worthy of acknowledgment. Fair enough.

The second type of headwind I’ve encountered has been people’s well intentioned identification of specific challenges that I’ll face in my business venture. Be they questions I have to answer or things I have to account for or hoops I’ll have to jump through, folks I talk to seem to be quick to identify such obstacles.

I’ve decided that I don’t fault anyone for this tendency, because I think it’s attributable to two very natural things: one is that pointing out these challenges may constitute a person’s attempt to help me, in case I haven’t already identified the challenges for myself; the other is that I think most people are generally risk-averse, so our minds are wired to most quickly identify the reasons for which we would hesitate to start down a particular path (even if there are many good reasons in favor of doing so). In accepting these as normal human tendencies, the behavior I’m referring to isn’t necessarily even indicative of the doubt that it implies at first blush, so no hard feelings.

As for the challenges being identified, they don’t faze me in the slightest. Why? Because my decision to pursue this venture was, of course, not predicated on the notion that I would not encounter challenges along the way. Quite the opposite: of course there will problems to solve. But what else is new? The identification of any challenges is important, no doubt, but anything short of ‘major roadblock’ status is just something to be navigated as a matter of normal course. This is not only part of the plan, but an important one.

The third type of headwind I want to draw attention to is, in a way, the inverse of the last one: instead of a tendency to identify challenges, people’s tendency to point out a simpler, more conventional path.

Most pertinently, the fact that I’m pursuing my venture on a not-for-profit basis does present some bureaucratic challenges: reporting and disclosure requirements are more stringent for such organizations, on account of the preferential tax treatment they receive. A few people have noted that I might find it easier to go the more conventional route of structuring the business as a regular, for-profit corporation, still having the ability to use the proceeds for charitable purposes if I so choose.

(For the record, the basis for this suggestion – avoiding some measure of red tape – is of course not wrong, but does miss the fact that I’ve chosen this approach for reasons other than logistical simplicity.)

Again, I think this tendency I’m describing is natural and comes from a place of people wanting to be helpful. After all, it could be the case that I simply haven’t recognized that there may be an “easier” way to do things, so I do appreciate the helpfulness inherent in the sentiment. But it turns out that there’s an even easier path available than the one that’s been suggested to me: go back to White-Collar Purgatory and forget all about this wild world of the unknown. Which is to say: sometimes there are reasons – valid or not – for not necessarily opting for what’s “easiest”. As for my relationship with Purgatory… yeah, life is “easy” there. But, as you know, that didn’t stop me from experiencing Mugatu levels of bewilderment in that environment. (Seriously though – was I taking crazy pills?)



All in all, these first couple of weeks have been hugely rewarding, stimulating and hipster-in-a-thrift-store fun. Perhaps the coolest thing about this New Reality has been that, really, there are no rules. There is no one directing me nor advising me as to how I should spend my time or approach my business venture or otherwise navigate the world. There is as little guidance as there is accountability, which is both terrifying and liberating. And as much as I want to steer clear of the dead-horse concept of freedom (thanks, America), I can’t help but think that what I’m experiencing is a glittering, intoxicating manifestation of exactly that.

Now if you’ll excuse me, I need to address the terrifying and thrilling question of when exactly I last showered.


8 thoughts on “Views from the Sixteen

  1. Just remember, sweatpants aren’t for outside of the house! Unless you are exercising I think, not my thing so … ? Have to add, your purgatory roots are still showing, too many meeting with powerpoint presentations I think. Or maybe this is just you feeling your way with ALL of the words? Oh wait, you’re reflecting? You probably need all of the words then, sorry!

    Liked by 1 person

      1. It’s going to take time, you were in that world for how long? Old habits die hard (I nearly didn’t leave a comment but my cold/flu meds talked me into it) and finding your voice without those layers will happen. I sort of think you have so let’s call this a relapse and move on 🙂

        Liked by 1 person

  2. If anyone has ventured down into this comment section, let it be known that subsequent to the above comment exchange, I’ve gone back (now approaching 24 hours after initially posting it) and removed several hundred words from this post. And man does it feel good!


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