As former chairman and CEO, Dan grew Shopping.com from zero to more than $100MM in five years and took it public in 2004. In 2005, eBay bought it for $620MM. Dan has a soft spot for marketplaces and sits on the board of Lending Club (NYSE: LC), ShopKeep, CircleUp, and JOOR.
What’s your favorite restaurant for a business meal? And what should I order?
Da Umberto (107 W. 17thSt., New York). It’s all incredibly good, but their veal parmigiana will make your head spin.
Can you share your latest wellness “hacks”? Are they working?
I added a trainer, twice a week, to my workout regimen and started to take Metformin, a low-cost (five cents a pill) generic drug for diabetes. I don’t have diabetes, but clinical trials show that those who take Metformin (remarkably, even those who have diabetes) live significantly longer than those who don’t take it. I suspect that high blood sugar is a significant marker for inflammation and mortality risk and that Metformin addresses those risks above and beyond diabetes prevention. I also lost 10 pounds since I started taking it, and I feel great.
If you could pick one company to buy, own, and run as CEO, what would it be and why?
Fox News. There’s nothing wrong with espousing conservative (or progressive) viewpoints as part of a new format. But doing so in a fact-free manner that is more propaganda than news is a terrible thing for society. [The late legendary senator] Daniel Moynihan once said, “Everyone is entitled to his own opinion, but not his own facts.” I would love to run Fox News and keep its conservative bent but ensure that this prism was filtered by facts rather than fantasies. Now that would be fun!
Which technology do you think will most disrupt your industry?
AI and genetic manipulation. We are much closer to the singularity (of man and machine) than most people realize.
What key global trends keep you up at night?
Climate change together with wealth disparity and the political polarization it causes. Sadly, they feed on each other in a terrible feedback loop for the planet.
How is your investment strategy different from others?
I tend to be much more barbell than most. A heavy percentage of my assets are in “alternatives” — real estate, venture capital, and private equity. Roughly an equal percentage are in munis and other fixed income. I don’t have as much in traditional (public) equities. I’m not necessarily saying that’s the right approach, but diversifying heavily on either end of the risk spectrum seems to be working for me so far.
Which investment sector(s) are you most excited about and why?
I’m not sure if “excited” is the right word, but real estate continues to be the most tax-advantaged investment sector in the world. Whenever you invest in real estate, you are already ahead from a tax standpoint relative to any other asset class. There’s a reason many of the world’s billionaires started in real estate. One of them once told me, in response to a question on expected return: “I’m in the business of real estate - where the expected return is unlimited”. Hyperbole obviously, but with the kernel of truth that a lot of hyperbole contains.
If you had the power to solve a societal issue with a magic wand, what would it be and why?
Climate change. Huge parts of the world will literally become unlivable over time, since human beings cannot survive outside in temperatures over 120 degrees Fahrenheit and 90% humity for more than 6 or 7 minutes. The Persian Gulf is almost there and the Indian subcontinent is not far behind. It doesn’t take an apocalyptic mindset to realize that very bad things will start happening when hundreds of millions of people start dying because they were born in the wrong place. They will not suffer their fate quietly. Mass migration movements will make today’s geopolitical tensions look utopian by comparison.
Predict something. Anything.
I’m going to echo Scott Galloway on his prediction regarding Tesla: It will go bankrupt within the next 18 months. I love what Elon Musk has brought to the world and I love Tesla as a product. But Elon brings a certain quality of “the man behind the curtain” pixie dust to the company — one that can’t hide the unsustainable financials that I think will ultimately spell its demise.