Michael Loeb

Origin Story: In a couple sentences, how would you describe your path to becoming an investor?

I didn’t become an investor until I was an entrepreneur, and I didn’t become an entrepreneur until I was fired. My firing got a lot of ink but not a lot of sympathy. I had little choice but to start the company that I wanted to start inside of Time Warner (my former employer), outside of Time Warner. Synapse, the result, also begot Priceline.com. The monetization of those businesses became the foundational capital for Loeb.nyc, our self-funded venture collective with two dozen startups, most built de novo, and our passive investments.

Investment Approach: What are the key factors you consider when evaluating a founding team?

The founder. True entrepreneurs have many identifiable qualities – intellect, drive, endurance – but most important of all, is the insistence on winning. Entrepreneurs know no barriers. A blocker? They go through it. Or over it. Or under it. Or around it. But they will not be denied. An entrepreneur with these qualities inevitably builds exceptional teams that are devout.
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What's your style and approach when it comes to working with founders post-investment? What are the characteristics of founders you've worked well with?

I was once given extraordinary advice: be the founder’s friend. Curious? It’s lonely at the top. Founders are like hockey goalies with a half dozen pucks on the ice and bereft of defensemen. Decisions have to be made fast and furiously with too little data and no time for contemplation. Teams simply cannot be informed of all the consequences – they would be frozen in fear. Every business that I have founded or funded has survived life extinguishing events. Great entrepreneurs survive and thrive in these circumstances, but having a steady hand and a calm mind to tell them “we’ll get through this” is often the most impactful contribution that can be made
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If I'm coming to pitch to you or your firm, what's the one piece of advice you'd give me?

Tell the truth. Don’t exaggerate. Lay bare not just the positives, but also the negatives and the risks. Your audience, VC’s and other investors, are discerning, discriminating and intelligent.  They are all-seeing and all-knowing. Don’t try to fool them. They know better and your credibility will be ground to dust.
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How would you describe your own personal mission and values, and how do they impact the way you invest?

I’m impressed with the words of John Keats “here lies one whose name was writ in water”. This is on his tombstone as a big f#@k you: you and your memory will disappear in an instant. Me? I’m carved in stone.I want to build disrupting, inventive, enduring businesses. My sum and substance will be when generations forward take notice and say “that one was cool”.
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What do you like best about investing in NYC, and what’s your outlook on the future of NYC tech?

What I like about NYC tech is NYC: I’m a New Yorker, but I do worry about our city at least in the near term. In the end, New York’s many attractions when they are back – the restaurants, museums, theater, nightlife, etc. – are catnip to young people in tech. This cannot be replaced by Zoom calls nor is it available in our leafy suburbs. New York will be back but it will faster with the right leadership.