Why a kayak.com for car insurance?

How I chose my startup.

So, after literally millions of ideas, why and how did I pick a kayak.com for car insurance?

1. I worked as a business systems analyst for a bank
2. Consumer banking sucked and I knew I could do it better
3. Bright Idea A: Reinvent consumer banking

Now it was time to do research… and here’s what I came up with:

1. I didn’t want to partner with existing banks or do a Mint.com concept because I didn’t like their monetization models around their products
2. I also felt that being the bank itself was absolutely essential after having tried Mint. Despite it being a very valuable service, it was not valuable enough for me to micro-manage
3. Given #1 & #2, I would need to start a new bank or buy a failing bank for about $10 million and have an additional $40 million in cash to satisfy Tier One capital requirements
4. Due to lobbyists, it was no longer possible to open a new bank.
5. Ergo, modus tollendo ponens, I would need $50 million in cash. .. and that doesn’t include product/ service development. Ouch.

I evaluated the likelihood of me getting $50+ million to start a bank and didn’t like the odds… so I started thinking about how I could start a legal business that could make $50+ million in cash.

1. I had been brought in as a consultant for a kayak.com for health insurance concept
2. The revenue side was great, but I was concerned about a) the difficulty of selling complex health insurance products online (validated by the difficulties of publicly traded ehealthinsurance.com), b) the fact that people don’t shop for health insurance on a regular basis and switch to employer sponsored healthcare whenever they can, which complicates the customer acquisition side of the model and the customer churn, and c) Obamacare was on the horizon and I didn’t know how that would impact the marketplace.
3. None of these flaws were present in car insurance…
4. Bright Idea #2: kayak.com for car insurance (and add other insurances down the road)

Our Plan B is God’s Plan A — Daniel Eliezer Weisman