The Players Technology Newsletter 27.0 — 06/02/19


Hey <<First Name>>, 

A couple of weeks ago, two-year-old online sports-video site Overtime announced it had raised $23M in Series B funding, valuing the company at over $100M. Although I was happy to hear that my good friend, CEO Dan Porter had taken the company to new heights, I couldn’t help but think of the fact that he gave me a chance to be his very first investor and I passed! 

Fortunately, or unfortunately, being a venture capitalist means placing a lot of bets. Sometimes you hit it big with a startup, and sometimes you lose it all. But sometimes you never place a bet at all—and end up missing out on an idea that can turn out to be a multibillion-dollar winner.

Investors love to talk about their successes, but seldom publicly acknowledge their misses. 

I’m the lucky guy that gets reminded constantly for my misses, as Alex Mather, CEO of the subscription-based sports website The Athletic, makes sure to remind me that declining to be his third investor is currently worth eight figures plus. 

VCs are always on the hunt for the next 1000x company, but even the most experienced investor can fail to see the amazing potential in a company that’s just getting started. Maybe the marketplace or model looks uncertain, the potential upside doesn’t appear big enough, or the company’s valuation is just too high. In instances like The Athletic and Overtime, I didn’t believe both business models had the market size both founders pitched me. 

Fortunately, passing on a killer investment is not the end of the world, I believe it’s best to follow those companies closely and learn from what you missed. Those key learnings are what make the diligence in making the next investment that much better. 

Venture Capital is for generalists. You need a curious mind, and you better love learning to quickly understand business models, technologies, and industries you’ve never dealt with before. However, it’s important to develop a certain expertise in the sectors you want to invest in and surround yourself with as many experts in those sectors as possible. 

Most things that seem nuts are nuts. But every once in a while, what appears nuts is one of the 15 ideas each year that 95% of financial returns in venture capital.

The one thing that ALL venture capitalist have in common is they all failed to invest in MOST of the big winners. Luckily for us, I’m not the smartest guy in the room, but I sure as hell make sure I find out who is!



Love this Newsletter? Send it to a friend!
Was this email forwarded to you? Sign up here!

Interesting Articles:

The Anti-Portfolio

Honoring the companies we missed.

Read More

Confessions of a VC: Why I Passed on Uber’s Seed Round

Did I pass on Uber’s seed round? No. It’s worse than that. I did not even bother to listen to Travis’ pitch.

Read More

Tech Is Splitting the U.S. Work Force in Two

A small group of well-educated professionals enjoys rising wages, while most workers toil in low-wage jobs with few chances to advance.

Read More

The Exquisite Physics of Kawhi Leonard and the Gravity of the N.B.A. Finals

Kawhi Leonard, of the Toronto Raptors, doesn’t defy the rules of physics; he understands them.

Read More

Why Are Young People Pretending to Love Work?

I saw the greatest minds of my generation log 18-hour days — and then boast about #hustle on Instagram. When did performative workaholism become a lifestyle?

Read More

The Real Difference Between Creators and Influencers

It’s not a gender thing.

Read More

Salesforce’s Success Rides on One Man’s Gut

Marc Benioff’s acquisitions have kept the software giant growing at an incredible rate. He’s also made some costly errors.

Read More

20 Years Ago, Jeff Bezos Gave an Interview Detailing Amazon's Killer Strategy--and It's Absolutely Brilliant

A fascinating look into how Amazon become one of the most dominant companies in the world.

Read More

Frozen Moment: What Makes Elite Golfers Different From the Rest of Us

Watching Rickie Fowler at the PGA Championship taught a valuable lesson of what separates golf's greatest players from everyone else.

Read More

Uber Eats has Taken a Supersized Bite out of McDonald's

Uber Eats is now available at a whopping 9,000 of the fast-food giant’s 14,000-plus U.S. locations.

Read More

As E-Sports Grow, So Do Their Homes

To provide fans with a richer experience, developers are creating arenas that are designed for pro gaming.

Read More

Kanye West Is Launching a Creative Incubator for Young Designers

Since launching the Yeezy label in 2014, Kanye West has filled his studio with plenty of young creatives, like archivist David Casavant and stylist Ursina Gysi, not to mention the creatives he has worked with in the past, including Virgil Abloh and Jerry Lorenzo. 

Read More

“If your mind is empty, it is always ready for anything, it is open to everything. In the beginner’s mind there are many possibilities, but in the expert’s mind there are few.”

- Shunru Suzuki

You are receiving this e-mail because Rudy Cline-Thomas added you.

Want to change how you receive these emails?
You can update your preferences or unsubscribe from this list.