[El Diablo]

All,

OK, I'll take a shot.

Interned as an engineer in college, realized that I didn't want to do that. Considered i-banking and consulting. I-banking didn't sound like much fun to me (my friends were working 100-plus hours), plus I've always had a thing for "building/creating" stuff, which didn't seem to come into play much in banking, so consulting seemed the natural course for someone with no clue what to do.

Got a job making something like $45k total w/ bonus (1993). Did that for a year. Was 100% staffed at billing rates of $150+/hr. Hmmmmm... Also hated having people above me in the company that were idiots.

I quit and got a consulting job making about $70/hr. Did that for a year, then realized I didn't like it all that much more. Had some money saved up at this point.

'95 now. Started a web development tool software company with a couple of friends. Didn't have any clue what we were doing, really, no idea about market/competitive analysis. Moved to Bay Area. Burned most of my money on this, didn't really go anywhere, but was great experience and met tons of people in the startup and finance worlds.

Did some more consulting to make a few bucks (now making $100/hr) and came up with some enterprise software ideas that seemed good. Again, devoted all the money I had to getting this company going. I had worked on large natural gas trading systems in consulting and developed some related stuff for the web. Sold a couple of $50k+ customers while still bootstrapped, then raised some venture money.

Grew this company for the next few years, raising and spending a ton of money (total VC money raised in the ~$50M range). Biggest mistake throughout this process was hiring various execs simply based on the fact that they "had experience" and not firing the ones who didn't perform quickly enough. It's really great to bring on top-notch performers with great experience. But it can be devastating to bring on people who have just slowly moved up the corporate ladder over 15-20 years of uninspired performance. Their resumes often look great, but their ability to perform in a super-competitve world sucks. Anyway, at the point where we had raised ~15M, had revenues of a few million, and staff of about 150, we were offered $300M+ for the company. Investors vetoed the deal, looking forward to a big IPO. This was late '99, my share of that deal would have turned out to be worth about $50M when the lockup expired and I could sell.

Instead, we pushed forward to an IPO, but in early 2000 the whole tech sector crashed, so instead of doing that I spent the next year firing about two-thirds of the company and getting to profitability. We did that and sold the company for a fraction of the earlier offered price. I had a few bucks in my pocket, not enough to retire, but enough to not worry about work for a few years and not be stressed about the next thing.

I took a couple years off, travelling and helping other friends with startups, doing a little investing from time to time. A few of these startups ended up putting a few more bucks in my pocket.

Then decided to start another software company. All the initial R&D was bootstrapped by me and my business partner. Once we started having some sales, we raised a small amount of seed money from a group of friends to ramp up staffing and marketing, but have so far passed up all offers of professional outside investment, instead trying to scale this via revenues. In a year or two, this will either look like a genius move or an idiotic one, we'll see.

I could have gone down multiple paths that would have made me a ton more money (after my last company I had numerous offers to work at VC firms making a ton of money or joining high-flying startups as CEO or senior management), but I've pretty much focused just on being my own boss and keeping as much control as possible on what I do on a day-to-day basis. This has involved me at multiple times putting just about everything I have into the next business idea (and in the early attempts, putting on sizable credit card debt as well) rather than put the money into more conservative investments. But the way I figure it, there's always a way to make money and always time to go get a high-paying job working for someone else. I have no regrets sacrificing those types of opportunities numerous times and I can't overemphasize the value of actually doing stuff - fundrasiing, selling, managing people, delivering product, negotiating deals, whatever. That type of experience is not only valuable, but also really fun and fulfilling to accomplish.

I plan to stay in this field, working with my current company and a few others I'm involved with, for a few more years. Then I think the most likely next thing for me is starting a small boutique investment bank with a couple of guys I've worked with on various projects for 10+ years.