When you set off on a grand adventure of entrepreneurship, there are a few milestones you’ve got in mind:

• Your first focus group
• The “beta” launch
• First revenue
• Profitability (!)

There is an easy tendency to imagine this as a steep hill, that gradually levels off as you approach the top. ‘Surely,’ you think, ‘It must be simple to get to profitability once you’ve got revenue, right?’ Not so much.

BountyUp achieved first revenue almost immediately after first launch, but we’ve finally hit the “wall” - the point at which it seems like we won’t get to profitability fast enough to capture this market, without plunging in and going at it full time. Of course, if you read that carefully, you’ll realize that before we’re profitable… how can we afford to work on it full time?

The answer is, we can’t. So we’re going to raise a bit of money.

Now, technically, this isn’t our “first round” of angel funding, since we did a first round of $300 just after we started up BountyUp - that’s what paid for the whiteboard, the domain name, the hosting package, etc. But it’s definitely a more serious commitment.

Those of you who know me well will remember that I raised money for a startup once before - a startup that I lost control of, but which went on to do quite well. Quite well, that is, from a “pure business” perspective - since neither myself, nor my investors, ever saw a dime. One of the things that went badly wrong in that picture was our financing - it got WAY too complicated (Venture Capital, Investment Banking, Foreign Export Loans, etc).

So back to the once-burned, twice-shy: no institutional money. Which leaves us fishing around for a handful of adventurous angels excited by the prospects of an early-stage company with great vision, a great marketplace, no legal protection of their IP, and a low barrier to entry. (Anti-blue-sky disclaimer, there). I’ll keep you posted on how it works out - I’m starting with a Guy Kawasaki 10/20/30.

I was probably exaggerating a bit when I said “Hitting the Wall,” since I’m not giving up on this no matter what - money or no money. But it sure would be nice to quit the day job(s) and get some sleep occasionally.