Stephen McKeon

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

Stephen McKeon joined Ted Seides for a podcast about drones, (block)chains, and wine. Most of the second half is about McKeon’s articles about tokens, compliance, and liquidity. We’ll focus on the wider ideas. Ready?

At the peak of the dot-com bubble, spring of 2000, McKeon took a job at a tech startup. “I had nothing to lose. I had no dependents. Making rent was my biggest concern.” This is a great time to act because of the limited stakeholders. Though the startup failed, “It felt educational in some ways.” Like Jenna Fischer, McKeon turned a failed outcome into a helpful experience.

His next job was at a winery in Napa Valley. Shortly after joining, the winery relocated nearer to McKeon and he found himself doing more because he lived closer. McKeon worked his way up to CFO as people more qualified than him steadily exited. He got the job, “largely just because I was there.”

McKeon’s early career is the success equation. He advocates for active serendipity at the end of the podcast and emphasized that yes, luck plays a role in every outcome but there still preparation we can do. Like Annie Duke’s podcast with Seides, this humble point of view is crucial.

Ed Catmull writes that without considering luck, we trick ourselves into believing false causality. “We must acknowledge the random events that went our way, because without acknowledging our good fortune – and not telling ourselves that everything we did was some stroke of genius – leads us to make more realistic assessments and decisions.”

Not wanting to harvest grapes forever, McKeon headed to Purdue for a Ph.D. It was a “non-traditional path (but) I took those experiences from the winery and they served as the basis of most of my early research.” The boots on the ground experience often guides us to better information for decisions.

Andy Grove advocated we feel the breeze of the real world. Jan Chipchase wrote, “The best way to understand how a culture adopts (or doesn’t adopt) an innovation is to go there and see it for yourself.”

After his graduate program, McKeon got a job and met a pair of students who would start a drone company. Like his other startup, McKeon spent this time “being close to emerging technologies.” In addition to drone regulation, McKeon started thinking about blockchains.

As he talked with Ted, the second half revolved around Josh Wolfe’s question and solution; Ask what’s a huge pain in the ass and solve for that. McKeon explained how blockchain might change 24/7 trading, settlement time, fractional ownership and liquidity issues.

In the same way eBay allowed people to sell baseball cards, blockchain may allow people to sell anything or even parts of anything. “Blockchain offers us protocols that are specifically built to move value,” McKeon noted.

But why does it have to be blockchain? The interview is pleasantly devoid of buzzwords and McKeon thinks it’s a Gordian Knot. Microsoft and Google are incentivized to not agree to a common protocol, which is the dirt solutions grow in. It’s why Master of None was ten episodes on Netflix. “There’s no reason for twenty-two episodes of anything,” Aziz Ansari said. New tech lets people start fresh.

There’s still work to be done. “Wallets are still kind of intimidating to people,” McKeon said, but “Coinbase is like logging onto Fidelity.” ‘Design matters’ is an echo we hear from the IDEO team, Rory Sutherland, David Ogilvy and Dan Ariely.

This was an inspiring episode. Whether any of McKeon’s ideas will transpire no one knows but learning the thinking behind them has already been helpful.


Thanks for reading.

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