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Evolution of a Startup: Lessons Learned

I was recently approached by a friend in the venture capital industry who asked me to write about my experience as an entrepreneur and transplant to Silicon Valley.  Here's the resulting transcript of our discussion.  I'm publishing it in the hopes that it helps other entrepreneurs, as well as those who haven't yet taken the leap but want to.

Can you tell me about the fundraising cycles your company has gone through?

We began in Washington D.C. in 2008 in a townhouse on Capitol Hill. It was a terrible time to fundraise due to the financial crisis, so we self-funded a mobile consulting firm called PointAbout which built mobile apps for large brands, including Disney, The Washington Post, The Huffington Post, Newsweek, Cars.com and many others.  That firm quickly grew to over 30 employees (and a much nicer space in DC -- although still a townhouse!)

Should non-professionals research their own investments?

On SEBASTIAN MARSHALL

Patri Friedman left this very smart comment on the convincing arguments post -

I’m pretty skeptical of whether researching investments is a good idea for non-professionals. Financial speculation is fun, but you are competing against specialists who have spent their whole lives studying the subject, have teams of researchers, and are betting so much that they can afford to buy the best computers, data, etc. I think almost everyone should just buy the Vanguard Target Retirement 20X0 fund.

The exception is if you’re in the startup world & you know people who you trust & respect who are doing startups, angel investing in them w/ 10%-20% of your income makes sense to me. At worst you’ll lose a little money & learn a lot about who to trust & how startups work. Another is if you know a city/region/country very well and want to own property there – ownership has advantages (ie we have done extensive customization of our cohousing community here in Mountain View) and since it’s such a big asset it’s definitely worth researching.

This is a great point.

I've been studying a lot of finance lately. One that I've really enjoyed is "The Intelligent Investor" by Ben Graham.

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