When people ask me what I learned at HBS, I sometimes say never buy the extended warranty. I’m kidding, of course, but as all B-school students of the late 90's know, once you understand the economics exposed by the Circuit City case study, it’s hard to justify parting with the extra cash.

Those overly attractive economics were the first thing that came to mind when I met Chinedu Eleayna to learn more about Mulberry, back in November of 2018. …

This Spring marks three years for me on the dark side of the VC business, as an investor in startups rather than an operator of them. Reflecting back on the advice I got and what I’ve learned since, a few things seem worth passing on, including something I’d add to the list of good counsel I got from others.

“Don’t do a bad deal your first year.”

The first is “Don’t do a bad deal in your first year.” A bad deal right out of the gate not only hurts the fund, it consumes the time, focus, and confidence required to build the foundation of your “practice” as an investor… the network of relationships and institutional sources of deal flow that are the lifeblood of a successful VC. This was actually the single most common piece of advice I got, from savvy investors and trusted friends including my partner Bill Wiberg, friends Jamie Goldstein and James Nahirny. I took it seriously, to the point of not doing any deals that first year out of the gate (though to be clear this was not my intention.) …

It’s good to know a guy. Growing up Italian I’ve always known this, though later in life I learned to say it like a ‘Medigan: The right relationship is everything.

That’s why LinkedIn — now the closest thing we have to a system of record for business relationships — stands astride the recruiting world. They’re the 800-pound gorilla, leaving smart startups to compete, enhance their platform, or look for under-served niches in the market for sourcing and recruiting candidates. …

As the 2020 Presidential campaign gets underway in earnest in Iowa, national polls show Trump losing to all of the Democratic front runners, in some cases by a comfortable margin of 13 points.

Don’t believe the hype.

Democratic primary candidates are spending their time before Iowa caucus goers attacking Trump rather than putting forward a real alternative to the anger, resentment, and fear he rode like a castrated pony into office. As they do, my own fear and anxiety of a Presidential election eve just like the last one only grows.

Please, God, no.

“What about Elizabeth Warren?,” you say, referring to the former professor who “has a plan for that” no matter which underlying root cause you attribute to red America’s 2016 electoral temper tantrum. If campaigns were fought on policy I might be reassured by the Senator from Massachusetts, but — here in the real world — they are not. Presidential campaigns aren’t fought on resumé, or work effort, or even money in the modern age… and if you doubt that just set a spell with President Clinton on her porch in Chappaqua. …

As my interest in being outraged has declined over the past few years, so has my use of Facebook. Instagram has become a kind of welcome haven, a way to keep in touch and share moments with people interested in them, with fewer negative side effects on my blood pressure, family relationships, and the global world order.

I started seeing things I wanted to buy in my Insta feed. I developed a relationship with a small brand in San Antonio called Bexar (“Leather goods with an adventurous soul,”) and after extolling its virtues was eventually gifted an awesome backpack by my partner, Bob Hower. I picked up a beautifully made pocket knife from a small batch manufacturer in Oregon called Benchmade, then a miraculous little fire starter from a company called Überleben in Idaho. I’m still surprised by how easy the whole process is — even on my phone — clicking with minimal text entry through a post, to a Shopify store, then approving the transaction in PayPal. …

When we talk about G20, we try to use the same communications discipline we preach to entrepreneurs: Pick a story, and stick with it every time. Ours is (hopefully) familiar by now:

Early traction capital for East Coast enterprise tech startups, backed by the power and expertise of 20 of the Northeast’s most accomplished entrepreneurs.

The truth is around the time we raised our second fund we expanded the backing of our Members beyond the original 20, adding a few people with whom we’d worked closely and held in high regard both personally and professionally. …

One of the best things about being a Series A venture fund is you don’t have to look at as many early stage deals as your upstream counterparts. Many of our deals come through G20 Members, in fact, or from partners we respect in seed stage funds from here to Tel Aviv.

That said, I’ve spent a lot of time in the last month or so reviewing angel and seed stage deals systematically, creating and refining lists in Crunchbase, reviewing them initially with team members, and finally screening them one-by-one to get down to a short list of prospects we can dig into offline. That process yielded 25 interesting companies as of today, a respectable 2.5% …

“Jeepers, Michael! You just gonna let him push you around like that!”

It was past 6:00pm, four hours or so into a high school football practice gathering darkness to the cold and damp that had already overtaken it. I was tired, soggy, and sad in my helmet and pads, waiting for the whistle that told us it was time to go home.

I’d held up pretty well that day, until about 20 minutes earlier when I’d heard the whistle I thought would set us free, followed by the two words Johnston players most hated so late in those days. “Goal line!” Coach Centore said, the signal that not only was practice not over, but that we were going to stand off against one another — offense to defense — to fight for the most hallowed patch of dirt on that tired and dusty field, between the 5 yard line and the end zone. …