Howard Lindzon invites me to San Diego, excuse me – Coronado, periodically for events like “Lindzonpalooza.” In some ways he’s our Taylor Swift – celebrating his #SquadGoals with an assortment of people he’s come across during his multi-decade career as trader, entrepreneur and investor. Although he takes way more “foot selfies” than Tay Tay does.

Hunter Walk: You’re a Canadian who moved to Phoenix and then San Diego. Explain this geography.

Howard Lindzon: I was born and raised in Toronto and went to University in London, Ontario.

My family had a home in Arizona and I fell in love with the desert and Arizona State where I went for graduate school in Tempe, Arizona. I ended up staying to work in Arizona and lived there for twenty years. We would do summer vacations in Coronado to escape the heat and in 2009 thought it would be fun to try living on the island for a year. We never left. No fancy story, just a fun adventure and now we call Coronado, San Diego our home.

HW: In 2006 you created Wallstrip, an online video company focused on the finance vertical. Wallstrip was purchased the next year by CBS. If a media entrepreneur approached you for advice on creating Wallstrip 2.0, what guidance would you give them?

HL: I get approached on media startups all the time and was an angel investor in Business Insider back in 2007. It takes a very special founder to build a media business long term. I have not met many. Really Stocktwits is Wallstrip 2.0 as I left CBS early to start it. User generated content is the smartest, most efficient way and now that people spend more of their web time on smartphones and messaging apps, building a media business is even harder. I have been right and wrong about video. It remains silly hard to monetize even the best web video content, even at scale. Too hard for me to keep banging my head against the wall. It is obvious that video is huge, but it’s huge on Youtube and Facebook, not individual media sites. Long story short, anybody and everybody is a media business so start that way and prove you have a voice first.

HW: Social Leverage is your early stage VC fund and even prior to SL, you were an angel investor. If you could ask a founder just one question to try and qualify the quality of the deal, what would it be?

HL: The one question I ask immediately is why? What itch are you scratching…which tells me about their domain expertise. Startups are a war. They are a long road and I want to be in business with founders that really understand the domain they are attacking.

HW: What’s an avoidable mistake you see founders commonly make when pitching angel/seed investors?

HL: There is no one mistake..mainly founders are not taking enough time hunting the right investors.  I won’t pitch over the phone.  If I really want to pitch an investor I will get into a face to face and probably will have taken much time before making sure the investor is interested in the problem I am solving.  I don’t get the point of having investors that are not interested in the problem you are solving. When you really need them they can’t give you the advice you need.  Most founder and startup advice is available for free on the web and at your fingertips on your social networks.

HW: Your bio mentions looking for the “perfect sleep system” – how’s that going?

HL: Sleep remains a mystery to me. Most of it is mental. I am stuck on the Ambien train for most of the last 15 years. I am now 50 so I doubt it gets easier to sleep. I don’t trust people that can sleep at will 🙂 … they can’t possibly be busy! The 7-10 days of travel has not made my sleep problem easier. I do think my routine messes with my sleep but I don’t want to change it. My doctor says Ambien won’t kill me, but lack of sleep will!