Tom Goodwin

Supported by Greenhaven Road Capital, finding value off the beaten path.

Thanks to @DavidWakeman we’re going down a Tom Goodwin rabbit hole. Goodwin is @TomFGoodwin on Twitter, writes at LinkdIn, and author of Digital Darwinism.


Goodwin got fired from a big advertising firm in NYC. Then, “I was sitting at home, quite angry at the lack of change that was happening in our environment. I found it particularly frustrating that advertising agencies are very smug about being innovative and creative.”

So Goodwin started writing and without a boss he wrote freely.

The investor’s boss is their LP and those LPs should let them act freely too.

Brian Singerman said, “We have LPs we like.” Graham Duncan said, “You always want to feel comfortable holding cash and there should be no pressure to put money to work.” Michael Mauboussin recalled Seth Klarman saying something like, “The definition of a great client is someone who cashes a check when we write one and writes a check when we ask for one.”

In other businesses, it’s the hierarchy and culture. Good investors are opportunists, that requires freedom. That’s difficult to have, professionally and personally. Goodwin sees this regularly. It’s hard to propose something innovative if the risk of it going wrong means losing a job, then a house, then a place for your kids to go to school. Those people are “not really prepared to undertake the risk and to do something that’s gonna take a long time to pay off.”

What Goodwin wants those people to do is suggest more unimaginative and illogical things.

The Unimaginative vs The Illogical.

Humans want to appear consistent to others and themselves.

Humans do not want to think about path dependence or alternative futures.

In his book, This I Know, Terry O’Reilly wrote that some of his best commercials came from playing the ‘What-If game.’ If you want to see how well this works, visit any local third-grade classroom. Nine-year-olds are excellent at it.

The only problem is those stakeholders (above) support the unimaginative instead of the illogical.  “Increasingly I see clients spending more time… on showing a rigorous uncreative logical process as being followed so that if anything does go wrong they can hold their hands up and go, ‘the numbers told us this.'”

This is a problem said Rory Sutherland because many of those problems have already been solved. We’ve picked, clean, sorted, and stored a lot of the low hanging fruit. What’s left is the hard to get stuff. So instead of using a taller ladder, we need something different.

Be less unimaginative and more illogical.


“Leaving school and starting out or leaving school and traveling the world and writing or leaving school and creating a documentary are actually pretty remarkable ways to learn,” said Goodwin.

Why does someone select school? When is this choice cool?

Clayton Christensen encourages people to ask ‘What job is this person hiring for?’

We hire school for certain things, but as people like Daid Perell demonstrate, there’s other ways to learn skills, signal to others, and create social connections. Goodwin said, “I learn so much from Twitter. I learn so much from observing stuff as I travel the world. I learn so much from other people. Compared to what I learn in a normal week now, the university seems like an inefficient way to learn.”


My daughters are in the third and fifth grades and they take Spanish in school. The results are so-so and they don’t talk about it often.

Those same daughters take math, science, and choir and I hear so much more about those classes.

Each of those latter studies has its own language. Math has numbers. Science has taxonomies and terminology. Chorus is lyrical. So why is Spanish the laggard?

My guess is the native advantage. Their introduction to each of those latter classes is built around their native understanding of the world. They’ve counted since they were little, they’ve experienced biology, chemistry, and physics at each birthday party, and they’ve sung songs – baby shark do do do – for a long time.

They’re also digital natives. Goodwin said, “There is no online or offline there is just the modern world.” My youngest daughter was confused years ago when she couldn’t watch Netflix in the car.

“We don’t do electrical banking yet we talk about e-commerce.” Non-natives, like adults, think of the internet as a place you went. Natives think of the internet as a place that is.

“I’ve been going around the world and I still don’t think people understand fundamentally quite how omnipresent and how ingrained in our culture digital stuff is.” “If you use Tinder, you do not do online dating, you just do dating. If you get in an Uber, you’re not doing digital car sharing, you’re just getting somewhere.” “People now behave in a way where the internet is background to everything they do.”


Talk to your customers. Talk to your customers. Talk to your customers.

“We spend far too little time in the normal world.”

From Andy Grove to Terry O’Reilly, if you talk and listen to your customers, even mom, you can find out what their problem is. It is NOT a technology, but the solution may be. “It’s about people, it’s about empathy, and then know that technology exists.”


Thanks for reading. Want more Goodwin? Our notes were from The Learning Leader Podcast, The Career Success Podcast, Marketing Week Podcast, and Voices of CX podcast and two YouTube videos; from 2018 and 2017.

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