In Defense of Lifestyle
You don’t have a company. You have a job.
- Yale prof and Honest Tea founder Barry Nalebuff, to me, September 2006
I was in college at the time, running a small antique furniture reseller called Aloysius Properties on the side. Aloysius was a fun business. We realized that Ivy League schools, especially our own Yale, were selling their turn-of-the-century-era wood furniture at fire sale prices as they renovated libraries and classrooms. Aloysius bought as much as we could get our hands on and sold it online at significant markups — a 20x multiple wasn’t uncommon in addition to a 15% shipping and handling fee. And our customers (almost exclusively wealthy southern women) were thrilled to have these pieces of academic history.
It was very much a lifestyle business in every sense of the term. Specifically, the founders (Matt Brimer and I) wanted a business that threw off a decent amount of cash with minimal hourly involvement — that is, a business to support our lifestyles as college students. And it was a total break from our college lives spent staring at books and screens — buying furniture out of university warehouses, physically moving inventory, talking to customers and coordinating shipping was different and exciting.
But this kind of business went over with the pre-Lehman Yale crowd like selling crack in New Haven grade schools. It was gross, physical labor — a waste of our precious mental resources that would surely be better spent pricing derivatives or being flown around the world by McKinsey. In more precise terms, Aloysius would not get one laid.
The university did have a nascent startup scene. Innovation was encouraged, and traditional jobs in high finance and consulting were held in slightly less regard. But there was a parallel problem in the Yale startup community, one that effectively took the place of the larger university’s fetishization of high finance. There was the palpable sense that unless you raise significant capital, you’re not running a real business.*
This left Aloysius high and dry. Matt and I abandoned the business in early 2007, choosing instead to focus our efforts on raising venture capital for an online gaming startup, GoCrossCampus. Things didn’t turn out badly — my next company, PayoutHub, was acquired earlier this year, albeit not for fuck you money.
Since then, I’ve slowly getting back into “lifestyle-like” cash flow businesses. It’s entirely possible that I’ll see an opportunity in a company to take it to the next level and scale it into a venture-fundable blow-the-doors-off next-coming-of-facebook success. But I don’t have to, and there’s nothing wrong with covering my downside by starting with the goal of building profitable companies and seeing where it goes from there.
As a caveat, scalability of personal involvement is important. This is the difference between a job and a company — and helped spell the doom of Aloysius. Aloysius Properties was not only a personnel-heavy business, but it would’ve been difficult to pass off to an intern with minimal instruction (my litmus test for cash flow businesses). If you can’t pass it on to an intern with fewer than a few hours’ per week involvement, it’s probably a job. As you might imagine — and contrary to our beliefs at Yale — the litmus test has nothing to do with raising venture capital.
* Over the last few years, the Yale Entrepreneurial Institute has done a great job shifting this culture. One of last year’s businesses was a grilled cheese restaurant. Cool.

Not to nitpick, but that grilled cheese restaurant you mention _did_ raise a significant round of capital before launching.
Noted. Although I haven't kept up with it, my guess would be that the
capital didn't come from traditional venture capitalists — correct me if
I'm wrong.
That's right…it was an angel. But I strongly agree with your more general point, which is that there is an over-emphasis among entrepreneurs on creating an OMG NEXT BIG THING product, rather than something that is initially simply cash flow positive (or just breaks even).
A lot of the points you raise here are not in defense of running a lifestyle business, but in defense of bootstrapping. Maybe a future post?
Primarily, I think entrepreneurs should align their efforts with their own interests / desires rather than external sensibilities and trends. Starting a business in a small niche or with scaling issues may not be sexy, but it may be the best choice for the entrepreneur.
You can compare lifestyle vs. scalable businesses to being in a metal band. Being in a successful underground metal band is more like a lifestyle business (at best). You might have to “sell out” and soften your sound to become more mainstream (i.e. scale). If it's not aligned with your core music interests, you shouldn't do it, even if it gets you more fans or money. The same goes for an entrepreneur: if you don't actually want to leave your small niche, you shouldn't do it in the name of a trend or a paycheck.
Great post, and an important thing for techie entrepreneurs to remember (ie that making money is a great thing for a business, and not just shooting for 1bn users and the holy grail google acquisition and figuring out monetization later…). Ironically, one setting out to create a scalable, profitable 'simple' business can often find himself with something that can be grown quite nicely if it passes the litmus tests you point out. I think that running a startup like a true small business is a good thing for entrepreneurs to think about.
Great post, and an important thing for techie entrepreneurs to remember (ie that making money is a great thing for a business, and not just shooting for 1bn users and the holy grail google acquisition and figuring out monetization later…). Ironically, one setting out to create a scalable, profitable ‘simple’ business can often find himself with something that can be grown quite nicely if it passes the litmus tests you point out. I think that running a startup like a true small business is a good thing for entrepreneurs to think about.