Coastal Chicago - Year 2: What's Next?

In the (until I got diverted ranting about sentient AI employees) last post, I talked about what I learned during my first year in business.  In this post, I'll do a little navel-gazing and daydreaming to see where Coastal Chicago could be headed.

I'll start with my current situation - part-time consulting for Doctolib and helping to bootstrap Student Spots.  If I'm able to continue with both of these ventures at my current Doctolib rate (shhh, don't tell Doctolib) and make modest gains in the future from Student Spots (I'm sure the founder is far more interested in making more than modest gains, and I wouldn't turn the opportunity down, but my personal goals are a bit more meager given my starting point), I'll be content with my lot in life.

But nothing is forever, not even diamonds or remakes of songs about diamonds being forever, so it's worth exploring my options a bit.  I'm lucky (at least for the moment) that I have some good starting capital to draw from, so I don't have the same stressors that many other people in this situation have.  I've got some room for exploration as long as I'm not dumping scads of my money into speculative ventures (anybody wanna go halfsies with me on a Broadway venture tentatively titled "Beanie Babies vs. Pokemon"?)

There are two essential paths I can follow here - the solo path or the enterprise path.  The solo path would allow me to continue to pursue the consulting option, sell my services individually for start-up proofs of concept (POCs), and derive some income from my writing.  I'm tickled that I've actually got a starting structure for rates and/or hours for each of these endeavors in place, because setting your rates is one of the most difficult decisions to make when starting a business.

Given my relative experience in software engineering and management, I don't mind charging my market rate for consulting gigs.  I'd expect these engagements to be short-lived and targeted toward a particular facet of expertise.  And if people are specifically requesting my expert opinion, it makes sense to charge an expert's rate.  It's a little shocking at first to realize that someone is coming to you for your expertise, but it's best not to overthink it, lest you drive yourself into a manufactured existential crisis. 

When it comes to developing POCs for start-ups, I've been recording the amount of time it's taken me to add certain functionality to Student Spots, Travelectable, or the little one-off projects I've built for others, and have been pleased with with I've been able to construct in relatively small periods of time.  It's given me confidence to have a few set price points and associated deliverables, should anyone ask me to help out with a POC.

As to supplemental income from writing, I'll likely rely on donations and potentially one or two ads.  If my writing ever proves popular enough, I may generate some exclusive content for either a one-time cost (via something like a book) or for a reasonable subscription fee (ideally between $1 and $5 per month).  

I like the idea of keeping my content free for everyone and subsisting from donations, but that would require a much larger reader base.  The idea of artificially restricting some content for an arbitrary cost gives me some pause.  I believe that writers should be compensated for their content, but, especially in this format, it's hard for me, personally, to determine the value of my content without a lot more research.  And, since I'm not trying to attain the maximum dollar, I'm fine offering my work at a discount.

The nice thing about this type of solo business model is that it allows me flexibility and novelty.  In this set-up, I envision 10-20 hours dedicated to consulting efforts per week, 10-20 hours dedicated to POC efforts per week, and the remaining time (assuming a 40-hour work week) dedicated to writing.  

As I don't fully expect that I'll have consulting gigs and POC requests that consistently max out at 20 hours each per week, it gives me the flexibility to move among these 3 revenue-generating streams (or simply leverage downtime when things are slow).  

The other possibility is the more traditional route of concentrating on one particular site or product and honing that into a viable business.  From an abstract standpoint, the idea of finding a niche that I can improve and call my own, all while also being able to actually hire someone and prove to myself that there's more than one way to run a successful business is pretty attractive.

However, that would require me to identify said need, which I've been historically bad at.  I haven't actually taken the time to sit down and identify areas where I could contribute, so I'm assuming some effort on my part in this area would pay off.

Travel industry inefficiencies, of which there are several, would be a logical first step for me.  I'd also be interested in tackling other small inefficiencies in areas like the healthcare field that can make people's lives a little more bearable.

If Silicon Valley is constantly on the hunt for the next big thing, I'd be happy being the antidote that looks for the million little rays of sunshine that incrementally improve the world.  Apparently, among venture capitalists, a "lifestyle business" is a dirty phrase or a joke.  To unquote Justin Timberlake from The Social Network - "You know what's cooler than a billion dollars?  A business you enjoy that sustains your lifestyle and doesn't turn you into an instant douche."

Imagine carving out your own little niche business that nets a few hundred thousand or a million a year and brings joy to you, your customers, and your employees.  Call me crazy, but even on some level, that type of business could even work in the stock market.  We'd take the burden off of those poor, beset CEOs and allow them to concentrate on stable revenue models that focus on improving existing products rather than trying to monopolize industries in the futile chase to garner 10x gains every quarter.  Yeah, it'd take analysts some time to adjust, but then we wouldn't need to perpetually rush headlong toward a financial cliff in hopes we'll sprout wings before we get there.

Though I'm nowhere near this goal, there's a large part of me that dreams of the ability to provide at least a handful of employees the opportunity for stable employment and interesting work without the usual politics, slights, and casual cruelties performed in the name of "business" that accompany large (and sometimes small) companies.  

If my first doubt when striking out on my own was wondering if someone would pay me for my services, the next avenue I'd like to explore is whether or not my management model, can be successful.  I'm fairly certain it can be transferred outside of the one place where I employed it continuously (given my observations of other businesses that succeed or fail, I'm fairly confident in my opinion).  And, then, to go one step further, would it be possible for me to bootstrap such a model at a fledgling company, or am I reliant on the resources of a larger organization to be successful?

Minor apologies for leading on a post that essentially says, "I can build my own thing.  Or not.  And I can do it on my own.  Or not.  Maybe I'll be successful.  Or not."  But it was therapeutic for me, and most of you already know what you're getting into when you read my posts (apologies to any new readers).  

And, on the off chance one of you has an idea and is looking for some additional help, I'm always eager to try something new.

Until next time, my human and robot friends.