I agree with Rob here, going for the big win, although sexier, is much much more difficult and fraught with peril. And like you said Rob, although not as exciting, going after the less sexy niches can be very nice. Sure you won’t get covered by techcrunch, wired, etc., but you also won’t need to put in crazy hours forever.

I founded LandlordMax with the intent of growing it significantly. I knew it would never be a billion dollar company, but that’s ok. There’s just not that many landlords. However, it’s not an all or nothing. The goal of the company is to build cashflow, not to sell out. Selling out is by far the hardest exit strategy you can have. I’d rather have consistent growth (http://www.followsteph.com/2009/06/01/landlordmax-revenues-update/). Sure it’s not hundreds of millions in less than a year, but I’m very happy. And it’s not a win all or lose all enterprise.

The other big reminder is that being #1 does not necessarily mean you’re profitable, and if you are, it’s a tiny business compared with any ‘traditional’ business where you’re #1. Facebook is a great example here – undisputed leader in social networking, but losing money and quite tiny in the financial scheme of things.

Do you follow Steve Blank http://steveblank.com/
His book is worth finding.

I don’t think staying a one-person company is the only way to go, it happens to be the route I’ve chosen. In the post I also mention others who have not remained solo: Joel Spolsky, 37 Signals and Stephane Grenier (I think he’s more than one person, though not sure).

Balsamiq is awesome. I used the app in early 2008 and thought it was great, having no idea Peldi was doing everything on his own. He’s a great example of what a single-founder (Micropreneur) can accomplish.

For example, you are leaving technology factor out of consideration. With better (or new) technology one can outperform and outgrow competition, create new markets or re-segment existing ones. (That’s the reason why technical founders are getting more credit from VCs nowadays.)

At the same time, by following better business practices one can be lean, flexible, efficient, nimble or fast-growing – whatever is required to succeed.

Great technology, better business practices, talent, determination, and even technology enthusiasm, being put together, can greatly raise one’s chances to succeed (this is a universal rule for almost any venture, though).

Doing technology startups is probably hard and it is probably easier to fail than to succeed. But it is possible to increase the chances – which doesn’t make them look like buying a lottery ticket.

At the same time, sticking to a one-person venture sounds like an artificial limitation for a software business. Engineers and entrepreneurs are different species. Engineers can become entrepreneurs (or play a role), but a single person can’t excel in both areas simultaneously. Specialization is what drives the progress.

BTW, what do you think about Balsamiq?