Middling Management

For managers on the way up or stuck in the middle
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Startups & Who’s Buying?

Many moons ago before working in startups I had a cup of coffee on Wall Street. Well it was more like slightly to the north of Wall Street. Anyway, I got a small feel for the motion of the capital markets. Connecting the dots from how private companies grew into “small” or “mid” capitalized public companies. Hearing how public market investors evaluated companies on their way up and all that jazz.

Peloton, Crypto Hacks, and FCKS Given

Ah, another pandemic week of wild news. Through two of the most unrelated stories one can think of I was reminded of perhaps the most important thing when it comes to working and managing in startups. There’s the mission. The product. The team. But behind all that…there’s the amount of fucks you give.

I present to you two images:

A Note On My Guy Tom Brady

Allow me to be the first person to acknowledge there are too many sports analogies in business. I once saw a VC tweet “skate where the ball is going”. Clearly someone forgot Wayne Gretzky was Puck Jesus.. This week though? I’ve got to write a little something about my guy Tom Brady and his incredible career.

Early 2022 Directional Perspective

Many moons ago I sat down to eat with one of the co-founders of the startup I worked for. The company had grown pretty significantly over those past couple of years and it was a warm summer day down on the peninsula. So we decided to get outside for some lunch. Over a couple sandwiches we discussed our progress and some of the challenges that came with the territory.

The Drake Equation: Defining Silver Bullets

There are all sorts of dark arts that go into finding the silver bullets of success. That one feature, metric, team member, or breakthrough that will launch your company into the stratosphere. The reality though? You know. It’s far more nuanced. If we’re being honest with ourselves it’s more likely to be unexplainable.

Mercifully or Merrily On To 2022

Can you believe the end of the year is upon us? Mercifully or merrily, depending upon your perspective. Whether you led dozens of people or just yourself there was no shortage of psychology to manage in 2021. This will be our last piece of content for the year. I need a break too!

Mission Driven (?)

Everybody wants to join a mission driven company. Companies that accrue the best talent and are out to challenge the establishment with a world changing product or service. But a funny thing happens. Those castles in the sky eventually collide with cold bedrock in order to grow into sustainable enterprises.

Best Managers. Worst Managers. From Managers

Last week I mentioned that over the past few months I’ve caught up with a few dozen managers to hear about their management journeys. For some of those conversations, when extra time allowed, I asked them:

“What qualities did your best managers have? What qualities did your worst managers have?”

Here’s a summary of the responses:

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