WillPontificate

I bootstrapped a digital publishing business to over $200K per year.

Started 8 years ago, developed and published our first website for under $250 (I code, which helps). Learned SEO via trial & error, benefiting from the post-Penguin and Panda implosions that kicked a bunch of spam sites out of our target searches. Started putting together a predictive analytics package for investing in digital content, so we have an idea of how content will pull before we create it.

After that it was scaling and project management. Which has been a real learning experience, since a lot of publishing basically sucks... many people cranking out the same stuff. Very hard to keep "that special spark" in content at scale.

Still have the day job. Digital publishing is an 11 on the hot / crazy scale in terms of revenue stability (50% swings in monthly revenue on established sites aren't uncommon), so have a reliable pay check & health insurance reduces stress substantially. Plus I enjoy the work, most of the time.

One other benefit of having a "cover" day job: it allows you to "stay off the radar" as a small business owner and fairly affluent member of your local society. You've got a socially acceptable answer ("I punch a clock at company X") and don't stand out. Most people have no clue about the true scope and intensity of my side business, which simplifies things...

I love it. The simplicity of Bill Gate's resume.

"I build the biggest software company of its time"

<Drops the mike.>

I mean seriously, what more do you need? A list of coding languages that includes both Java and Javascript?

I favor brutalism. A 1998 style design completely contained in inline code in the header. Using base fonts and features that are supported by all browsers.

It has a unique capability: it loads quickly.

Morally, I agree with you.

From a practical perspective, however, that would cede what little voice the American companies have in the process to the Chinese government who would replace them with local lapdogs controlled by political allies.

The result would be software where censorship wasn't a bug, it is a feature...

Business strategy question. It seems like there will always be a conflict between the US view of censorship (bad!) and the reality of trying to operate in China's huge market (comply or be booted, basically)....

Is that good cause to create a separate brand or subsidiary so the reputation damage of having to comply with this stuff (you know they got nudged) doesn't hit home on the US brand?

Just seems like you're going to have a rough time if you're attempting to service both markets under the same brand...

Mathematically this probably could never be justified as a permanent hire. Not enough steady demand.

That's kind of the barrier to entry, no?

Bingo... a stable business you enjoy pursued for sustainable reasons. I'd add a slight financial component to the list of reasons (hiding in my basement for $50K/year isn't appealing) but that seems consistent with the strategy I recommended.

A second benefit: many established small businesses can be bought for under 5 X EBITDA ($10 MM - $100 MM sales) which usually can be levered up 3:1 using an SBA loan. You could also generate similar returns by funding the right types of organic growth projects. If chosen prudently, there's a lot of upside in those numbers.... (with some risk, naturally)

So while they may do it for the lifestyle, the underlying investment dynamics of the niche are very attractive...

Yes and no.

I agree with everything except #5. My marriage & kids are irreplaceable.

So if you have everything else, which is a more rational bet:

- Investing in a low probability, massive payoff

- Investing in a lower (yet still high) payoff with less variation in expected outcome.

There are huge segments of the economy where you can buy a small business for at a 3 - 6 multiple of annual earnings. Many companies in this space are unsophisticated, so there is massive potential for operational improvement as well (introducing basic process, tech, and marketing strategies).

Then that's the right strategy for you. You're intentionally loading all your bets towards a single massive payday.

For someone on Main Street, however, the odds of any payoff are probably more important than the size of the potential payoff.

Exactly.

Mathematically we're living in different universes. Moves that are rational for someone who has a few billion dollars under management don't work for the rest of us, because we're unable to diversify risk to the same extent.

Along the same lines, however, our "hurdle rate" for a life impacting investment is substantially lower....