I am a big fan of  Gimlet Media’s Startup Podcast series. Gimlet Media is the premier digital media company focused on producing high quality narrative podcasts. They are interesting, amusing and worth listening to for insights especially when walking the dog or on cross country car trips.  Season One covered the startup of Gimlet itself, with a well commented upon episode called  How Not to Pitch A Billionaire aka Chris Sacca:

Season Two covered a company Dating Ring that presented to Golden Seeds in NYC. GS did not invest, but I met the founders who were really great although despite a lot of press coverage,  impressive showing at Y Combinator, it was not clear the world needed another dating site. Especially as dating sites might be what was noted in Dating Ring of Fire Episode 9, a lifestyle company. Dating Ring of Fire Episode 9 .

Many companies that I have seen pitch at various angel events are lifestyle companies,  I have probably invested in a couple. The issue with lifestyle companies is that may be great companies, assuming they can generate enough revenue after initial funding rounds to keep going, paying the founders and employees reasonable salaries and having real offices and products. The problem comes in if you are investor and want to make a return, as that is not going to happen unless the company is acquired and in rare cases goes public.  So, key learning for me here was going forward and with my current investments, make it clear that I do not really want to see this company still existing as a cool consumer oriented company in 5 years. i would like to see it sold, so I get a return. in my lifetime. I think Golden Seeds has many of these companies which is why there have been to date no significant exits, but that is subject of another post.

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