Want to Pick On the Small Guy? Get In the Ring: An Entrepreneur’s Editorial

While some of my friends like Josh Brown (the first who came to mind – read his book, by the way!) are far better at this story-telling thing than I, well, sometimes things happen that compel you to give it a shot, so bear with me, please.

Stone Street Advisors LLC is the 5th project/company upon which I’ve embarked/started in the past decade or so (I might be missing a project or two but you get the idea). During this time I’ve held two real (“real” = traditional) internships at established firms and two real jobs at global banks. Read: I know what it’s like on both sides, so don’t bother trying to discredit the following argument so simply, I promise I’m not wasting your time.

Moving on…

Each one of my endeavors has been purely bootstrapped – no funding besides whatever I had in my checking account, and said adventures run the gamut from 2 web/e-commerce sites started while in college to spending the better part of 2 years on an investment banking type business for luxury assets (think mega yachts, jets, etc), to now, for the past year-ish, this; running a boutique investment research firm catering primarily to hedge funds and the like.

Each and every time I’ve started a new project/company (even while in school and/or gainfully employed otherwise), the vast majority of people I know think I’m insane and should just focus on my job/studies or get/stick with a real job (I really hate that term, if its not entirely apparent yet). While its amazing, in hindsight, just to get a regular paycheck & benefits or just being a normal student, some people – apparently myself included – aren’t cut out for being content doing it that way. No complaints, just fact of the matter.

Given that I’ve had real jobs, and apparently fake ones (like running a startup, the enterprises that drive the very economic development so desperately needed in this country, apparently doesn’t count as a real job?), I think I have a fairly decent perspective here, especially since I started at such a young age (18), and my start-ups have never really been in ‘hot’ sectors where venture capitalists and angel investors line up to throw money at you the more nonsensical your firm’s name sounds (Note to self: come up with ridiculous sounding tech company with no chance of profitability but a massive “untapped” market).

When I was an investment banking intern at an unfortunately now defunct bank, my job was well defined, to the point where I sincerely hope I don’t need to explain it, and the hours were as expected. When I interned in corporate development at a storied Bell Labs spinoff, I worked 40-50ish hours/week on corporate strategy and all sorts of other things, but my job was still relatively well defined. After graduation, as a junior investment banker, I did whatever the hell my bosses told me and worked as many hours as it took to get it done on time, but the job is still relatively well defined (Meeting at 9am, invariably get an assignment due before that the next day, attempt to master Excel models until 3am…). After that, when I worked in operations at a global brokerage, my job was painfully well defined, as were the hours. The shrink I saw then said I shouldn’t talk more about it (not really, but it was a traumatic time and I don’t care to discuss it further, besides to say that it was the polar opposite hours/responsibility of what I do now).

When I started Stone Street Advisors, I knew my job should be to identify investment opportunities that presented great risk adjusted return potential, and sharing that with clients or the investing public while between clients.

If you missed it, the operative word in the preceding sentence is “should.”

While no startup zen master, this was not my first rodeo, so-to-speak, as I mentioned earlier. It was (and is), however, my most risky and ambitious, with the utmost serious consequences for the remainder of my career in finance. For those yet to grasp the point: If I screw this up, I could be working the night shift at McDonalds the rest of my life, or worse. Capiche?

So, while I would love to spend all of my time as an investment analyst, because I own & draw my livelihood from the company, I’ve had to do everything myself (with some exceptions thus far). What is “everything,” you ask? Well:

- My primary analyst job, AND (in no particular order):
- Editorial/publishing
- Sales/marketing
- Media relations
- Client prospecting
- Bookeeping
- Website management/development
- Corporate strategy
- Treasury/capital management
- HR (even small firms have several of these issues)
- Legal (lots of it, lawyers are expensive so you try to do all you can yourself)
- Tax (same)
- IT (you think corporate IT is bad? Try doing it all yourself!)

…I could keep going but those are the main hats I wear, the main jobs I do on a regular basis. I’m not complaining; I chose this path voluntarily, and, if I pull it off, I should – if we’re going to keep up with industry parlance – earn good risk adjusted returns, if not better, as the company grows to scale (which it is, for those wondering).

I don’t screw around on the internet all day (although I did sometimes during one former “real job,” imagine that), no more so than the pioneers of computer software (some of you may call them hackers) just stared at their screens and listened to loud music. Every entrepreneur who starts a company without a trust fund/rich family friends/a hot tech idea should be able to relate, I hope, just as I hope those of you who’ve only held “real” jobs understand that calling Dell directly is infinitely worse than calling internal IT, and doing your own compliance is far, far harder & time-consuming than dealing with corporate, etc, etc. (For business founders, there is a BIG difference between biting off more than you can chew, ever, than starting a company that can scale, but that’s a longer conversation.)

Trust me, I’ve been on both sides. Starting this company & doing it all (mostly) alone is almost a Sisyphean task compared to the support you get with a real job. I’m not up all Saturday night/Sunday morning during prime NFL season (one of my only respites) writing/publishing/editing over 1,000 words because I want to do it now, but rather because this is when I have the time. I’m sure many of you also work on weekends, too, so you know what I mean, I think, although besides friends in law/accounting/consulting/finance/medicine, I don’t know many who have a 50+ page report with their weekend drink(s) of choice, but such is the life we choose.

Case in point, whenever people ask me why I don’t have a “real” job or even more infuriatingly, tell me to get one, I want to say, as politely as possible, in the words of Guns & Roses (warning: explicit lyrics):

Get in the motherfucking ring.

4 thoughts on “Want to Pick On the Small Guy? Get In the Ring: An Entrepreneur’s Editorial

  1. Amen, man. Having had similar experiences with starting start-ups, one successful and the rest flops, I have heard (and had) this conversation many times. In actual fact, I had it again with my good wife this week!

    People who aren’t wired for self-employment/entrepreneurship find it difficult to understand – appreciate, may be a better word, actually – and it is as frustrating as hell.

    As I’m sure you know, despite whatever they throw at you ‘what have you achieved?’, ‘nothing has come of it’, ‘not another idea’…you have to keep going because, let’s face it, without people like us, people like them wouldn’t have real jobs.

    Good luck on your journey, I hope this venture is the one that silences the doubters.

    • That’s a great comment, all of it. I forgot to mention that most people don’t realize that most startups aren’t profitable (if they produce any revenue at all) for years, if they don’t go the way of the Do Do bird before they ever do. For friends/family/other doubters, its like they expect you to instantly be making money hand over fist (otherwise its not a good idea after all, right?????). As you said, were it not for entrepreneurs, no one would have a “real” job, QED.

  2. All well and good to be “fighting the system” and we definitely do need this type of thinking to create new and exciting ideas, products, systems etc.

    However, much like the aspiring actor or athlete who is a waiter/bartender, one must pay the rent and put food on the table. Thus, while developing your newest and hopefully greatest business you need to have some level of employment or a very understanding girl/boyfriend, spouse, parents or trust fund. See Lee’s comments above.

    You are no different then any small business owner who is there well after everyone else has left to take care of the myriad of things that need to be done to survive and grow from cleaning toilets, paying bills to repairing leaking plumbing.

    You and many of your colleagues seem to express a sense of entitlement. Go ahead and be bold, work and think outside the box – we need that. However, don’t expect others to enable and support you directly or by proxy while you “do your thing”. Don’t think you can shun responsibility and support to others who allow you to indulge your dreams and passion.

    Nobody doubts that you are putting in huge amounts of effort and time to get your enterprises off the ground. But don’t fool yourself into thinking that you serve a “higher authority” and you are immune to the exigencies of the real world.

    So reach for the proverbial stars and do it your way, but remember to keep your feet on the ground.