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Finance Careers: A tale of two startups.

You will never know how wrong you were till you actually do it with your own hands and fail. If you are really lucky you get a chance to compare your performance against a benchmark that you can relate to.

I was wrong and I was lucky.

My first two ventures were inspired by Luke Skywalker. I was alone against the big bad world but unlike Luke Skywalker there was neither an Obi-wan to teach me how to spar with my light saber nor was the force that strong in, around or about me. The first two experiences quickly went where unloved ideas go to die when their time is over without doing too much damage.

Venture number three was different since it actually grew beyond me and mutated into an organization with a few employees, a team of partners and an incubator. Within a year of our product launch we quickly ran out of cash and then even faster ran ourselves into the ground. While the business we had started in its grand design may have made sense, without cash or revenues, a down economy was not a hospitable planet for dreamers. I learnt how wrong I was about my ability to run a business, generate revenues, find partners, retain employees and convince investors to part with their cash. It was nice being a CEO for two years; it was painful acknowledging that you had crash landed the resistance’s only battle cruiser into the gutter in a state beyond salvage, fit only for a write off.

The end result? At least once in your life you should search for a job and not find it. Do it for a few months and it will put life in a different context. I did my three months of penance between May and July 2001 immediately after the fatal battle between the dark side and my personal bank account that led to the demise of Avicena. Mid July finally caught a lucky break and got introduced to Shane Chalke at Annuity Net. This accident of fate led to an offer in Leesburg, Virginia, introduced me to Ittai, Will, Kristina and a number of other Northern Virginian geeks and hackers. But most importantly coming immediately after Avicena, venture number three and the breaker of many an entrepreneurial hearts, it gave all of us a benchmark that we could use to finally see how wrong and oftrack we were in startup mode in California.

Shane had done a great job in raising funding (40 million dollars by the time I left 15 months later), hiring a team (four CEOs at last count), rolling out products (five different platforms for related markets), locking down customers (blue chip insurance companies, broker dealers, banks and retirement advisors) and creating waves. It was at AnnuityNet that I first saw how involved contracting was whether it was non disclosures agreements, employment contracts, letter of intent, service level agreements or penalties for dropped transactions. While I had played a business role combined with an over all fire fighting role at Avicena, at Annuity Net I had stepped down into a function that sat between business, technology, domain and clients and though I had no direct responsibility for anything, I was plugged into all conversations as a facilitator. And that plugged in role exposed me to how a well funded startup works when a grand plan and an A class team finally come together. Annuitynet was a case study of everything Shane had gotten right and that we had gotten wrong in an earlier life. In many ways it laid the foundation for the business that was to later become Alchemy Technologies.

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