Back in 2017, I was sipping a Corona at the beautiful Monarch Beach Resort hotel bar in Dana Point, CA when a soothsayer laid out the future for me.
Howard Lindzon was telling us about his early investment in a little company called Robinhood. It was still a private company and a relatively small one at that time.
Howard had been calling for a renaissance in retail trading for a while and his start-up investing in Robinhood was one way of playing that trend.
The ironic part of this story is we were at an evidence-based investing conference that was mostly about asset allocation, index funds and financial advice.
None of us were thinking about 1990s-style comeback for retail traders and investors…except for Howard.
It’s not like he was simply predicting a retail bubble-induced frenzy. What Howard saw was the potential for technology and social media to give individual investors the opportunity to have more control over their investment decisions.
And he was right.
While index funds are still massive and gaining an ever-growing share of investment dollars, there is a growing cohort of investors who find picking their own investments some combination of entertaining, intellectually stimulating and fun.
Plus, investing doesn’t have to be all or nothing. You can still have the majority of your portfolio in set-it-and-forget-it index fund-style investing while having an allocation to a zero-commission brokerage account where you speculate, pick stocks, trade or go nuts.
I’m not gonna lie — I thought Howard was kind of nuts when he laid things out back in the day but it turns out the guy is a genius.
One of my favorite things about him is he’s not your average finance person. He’s funny, self-deprecating, out-spoken and does things his own way. He’s also been eerily prescient in seeing trends happen before anyone else.
Michael and I sat down with Howard (on Zoom) this past week and had an awesome conversation about his career, how he spots trends and where things are going with start-ups and much more.
We discuss:
- How Howard got into start-up investing
- The early Toronto stand-up comedy scene
- The state of venture capital today
- Twitter’s biggest mistake
- What led Howard to invest in Robinhood when it was just a start-up in 2013
- The difference between investing in start-ups and investing in start-up venture capital funds
- Why it’s so important to find a mentor
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