23 | Athletes and Business, Career Advice, and Tim Urban

Sport teaches you so much about yourself

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In honour of CbK #23, going to focus on some sport! Within the context of business and investing of course. For all my new subscribers this week, this weekly email is about sharing what I’ve been reading, learning, and compressing. But first, a quick quote from MJ:

I've never lost a game. I just ran out of time. 


Here’s the format of today’s email:

  • Part 1: Athletes and Business

  • Part 2: Career Advice

  • Part 3: Under the Spotlight: Tim Urban

  • Part 4: Bonus Quirky Content - Something to Read, Watch, and Listen.


Athletes and Business

Sport has been a huge part of my life. And business and investing has been a huge part recently. So to combine the two is something exciting. I always thought there were plenty of parallels and interesting points to consider. So behold them in all their glory!

Athletes and Investing [Link]

Biased, because I wrote this. Fun fact: Steve Smith’s mattress startup investment has netted him more than his whole cricket career! So why are players investing now more than ever?

  1. Mo’ Money Mo’ Players: Total NBA revenue exploded. In 1984, the year before David Stern became commissioner, revenue was $165 million.  In 2013 revenue was $5.5 billion. A 12.71% CAGR! The salary cap for players similarly expanded. In ‘84-’85, the salary cap was a piddly $3.6 million (just under $8m in 2015 dollars). Under the current agreement, it’s now north of $100 million. Where’d all this money come from? TV deals. It’s estimated the NBA’s ABC, ESPN and TNT deal through 2024-25 gives them around $2.6 billion in annual revenue.  Decent increase from the previous $930 million a year deal. Live sports are lucrative because they have ads that can’t be fast-forwarded through. Players a few decades back might have even had second jobs. Today those second jobs are replaced with allocating capital and starting family offices.

  1. They’re Offered Investments You Dream Of: For better or worse, sporting stars are put on a pedestal. So when a VC has a choice to invest alongside an NBA player or Jimbo Jones with daddy’s money, you know who he’s choosing. So just like big investors (re:Buffett and his BoA deal), athletes can access investment opportunities that we peasants can only dream of. And people might not just partner with athletes because of their sporting success and wanting to be buds. Top athletes have incredible social platforms and access to movers and shakers. But let’s not pretend athletes have nothing to bring to the table in the business world. They perform under intense pressure and perform at the highest level consistently. I do believe, that if curious and eager to learn, they easily have the insights and attributes to bring to the table. Being a professional athlete is an edge, no doubt about it.

  2. They Can Affect Investments: Athletes have a public presence and following like never before. Why not use it to their advantage? Because sports fans are mental. I’ve seen how powerful it is. A fringe NBA player probably has more supporters and haters than most VC investors. They deal with more vitriol (also support and sucking up) daily than a VC does per month. Why not leverage that interaction and fanaticism to benefit your investments?

“We saw firsthand how athletes are starting to have these global brands, these global influences. Connecting the world of tech and sports — it’s not just holding up a soda can and smiling. It’s how can you bring that company to the next level?”
- Andre Iguodala

My skill is, if something comes across my desk, and I don't believe in it, won't even look at it. At all.

One of the big lessons I took from Shaq, he took any and all opportunities that came his way (if he believed in them). Super admirable to just commit like he has

It aint about sitting at home going I'm gonna do this, I'm gonna do that, a lot of times these things just come up.

Athlete Entrepreneurs [Link]

Joe talks about how the athlete investing cycle will go through 3 main phases, two of which we’ve already experienced:

  1. The Athlete-Brand Partnership: The athlete is compensated with cash for associating himself with the brand and promoting their products or services. Makes sense for the brand and requires little work for the athlete - win/win.

  2. Equity Partnership: Similar to #1 but includes a small portion of equity for the athlete to incentivize them with uncapped upside. Usually reserved for the top 25-50 athletes in the world but have become more popular in the last 10-15 years.

  3. Athletes partnering with the best entrepreneurs in the world to create businesses with have large percentage ownership stakes: Instead of negotiating for a few percentage points with an existing brand, or putting up capital through a funding round, they will partner with talented individuals, fund the business themselves and capitalize off their larger equity ownership stake. This structure enables athletes to participate in the full lifecycle of a company and incentivizes them with potential growth each time they promote the product.

Athletes Vs. Founders [Link]

Not a bad little article. Has some lessons to learn from Eliud Kipchoge, Serena Williams, and Jan Frodeno.

The journey of successful founders and professional athletes is very similar; in both cases, individuals are going against the grain, the odds are stacked against them, and the chances of succeeding are minimal.

The Athlete CEO [Link]

How founders can learn from athletes to build better teams, understand the importance of recovery, improve focus, and prioritize self-reflection. Also how the role of a coach helps develop the full range of abilities that success requires.

There are many similarities between being a founder and an athlete — from evaluating risk and reward, moving from being unknown into the public spotlight, eliminating constraints to innovate on established routes, and knowing where you can fall and where you can’t. Athletes understand the importance of recovery, teamwork, focus, and self-reflection, and know what it means to build resilience and perseverance. The ones that make it to the top are those who never let anything stop them.


Career Advice

Career advice, so hot right now. May not be applicable to you, but feel free to share with someone who might find it useful!

Interview Process

TV makes a great point straight away about the advice:

don’t just tweet to tell me that what I’ve posted is obvious. I can assure you from personal experience that nothing I’m about to say is obvious to everybody

Common sense ain’t so common! There’s so much good value throughout the thread, but the closing tweet is my favourite:

It is normal to feel savagely beaten to a pulp by the job search process. It is a ludicrous, demoralizing, gruelling, phoney ritual. Give yourself breaks & do kind things for yourself. The only way out is through

Cold Emails

I’ve previous done a post on cold emails [link], but this thread by Brent is short and sharp!

My takeaways?

Do your homework. Explain who you are, why you’re contacting them, and what you want. Research before sending and specifically choose your targets. Offer a clear value proposition and give a natural jumping off point for conversation. Have a clear ask. Reiterate the value proposition.

My [Brent’s] Advice: Be personal. Give context. Be transparent about your intentions. Start with a small ask and build the relationship over time.


Under the Spotlight: Tim Urban

Each week I provide a little spotlight on someone I admire. Tim Urban is this weeks focus, in a nutshell:

  • Born in 1981 and grew up in Newton, Massachusetts.

  • Graduated cum laude from Harvard University with a major in Government.

  • Prior to starting Wait But Why, he worked at tutoring nearly every academic subject, as well as preparing students for standardized tests.

One of my all-time favourite graphics.

On Invest Like the Best [Link] [Apple Link]

Grand theft auto is this cool metaphor because you run over people on the sidewalk. And it's just this fun opportunity to be like, it's a world with no consequences. It's a world where you can just do whatever you want and nothing bad happens, right?

Now, it's not saying that it's awesome to run over people on the sidewalk, but it's this mindset where if you were suddenly playing a game called grand theft life, and you just had to build a career and do stuff and you had to act it out in real life, I think people would be so much more suddenly successful and true to themselves and risky and bold and creative. And they would try some interesting things. If people started playing grand theft life where there's a caveat that you can't do illegal things, I just think people would succeed wildly, they'd be much happier.

On The Tim Ferriss Show [Link] [Apple Link]

Love Tim’s thoughts around happiness. SO much to unpack here.

There’s two kinds of happiness that you have to kind of deal with both. One is micro happiness: […] Are you generally having a good Tuesday? And then, there’s like macro happiness. Are you present? Are you like yeah, I’ll dig into this current life for 20 years. I love it. Or are you like I was, for nine years after college, which is like I’m doing this now, but I really want to like – I should be doing – and that’s macro happiness. So, I think you have to worry about both.
I think that the most important one to get right, at the beginning at least, is macro. I think if your macro happiness isn’t there, you’re going to feel frustrated. You’re going to have a cloud over you. And then, I think you can work on micro happiness, which is about lifestyle.

And followed with this banger:

Happiness is like an equation, reality minus expectations is your happiness.

And so, you can work on two things. You can work on improving your reality, or you can work on not lowering but kind of refining your expectations to reflect what actually matters to you, which will almost always end up with them lowering, in a certain sense, and maybe going up in another sense. But the classic trap, of course, is you’re in a way better place than you were 10 years ago, but you’re just as unhappy because your hedonic treadmill concept is this term that psychologists use that your happiness goes up because something really good happens.

Advice for Job Applicants [Link]

Relevant to the previous section, but from the man Tim himself!

In the interview, be your most likable self. When companies hire employees, they’re also hiring the people they’ll have to spend half of each week with, and in any good company, culture is a top priority. If you’re stiff and over-professional, you’re not acting like someone people want to spend half of each week with, and you’re not showing them how you’d contribute to the company culture. If you’re yourself in the interview and you’re a good fit for the culture, that’s going to be a huge plus for you—if you’re yourself and you’re a bad fit for the culture, it’s not a company you’d be happy working at anyway. Win-Win.


Bonus Quirky Content

Something to read: What if Remote Work Didn’t Mean Working from Home? [Link]

This is something that hits close to home. For writing, the best and easiest work often comes away from home. In an environment with little distractions and encourages work.

The home is filled with the familiar, and the familiar snares our attention, destabilizing the subtle neuronal dance required to think clearly. When we pass the laundry basket outside our home office (a.k.a. our bedroom), our brain shifts toward a household-chores context, even when we would like to maintain focus on our e-mail, or an upcoming Zoom meeting, or whatever else that needs to get done. This phenomenon is a consequence of the associative nature of our brains.

And what Cal Newport does:

Last August, I finally relented and leased a modest office above a restaurant in Takoma Park’s small downtown, which is a few blocks from where I live. The space is not luxurious; it features few windows, and each afternoon music from the restaurant patio below rattles the panes. […]
I now leave a perfectly lovely house, with its light-filled rooms and comfortable furniture, to instead go sit on a used office chair, staring at an undecorated wall, ignoring the clangs and clamor of the diners below. I no longer work from home—I work from near home. And I’ve never felt more productive.

h/t to @ClarkSquareCap for sharing this article.

Something to watchYou Can't Ask That - Ex-Football Players [30 mins]

Love this. Real pointy questions. And honest answers. Apologies because it’s not a YouTube link, but it’s too good not to share.

It’s the Australian male culture, not to talk about things that you’re struggling with

I think that above quote always needs an echo. But love the below quote too:

Sport teaches you so much about yourself.
Were there some shit times? Yeah.
Were they good for me? Definitely.

Something to listen to: David Halpert of Prince Street Capital on the Indo Tekno Podcast [Link] [Apple Link]

My new favourite podcast of late. Episodes are a little short (~20mins), but some super interesting guests and focused on a region I’m fond of.

Interesting thought around the environment of startups at the moment:

My advice to an entrepreneur of a startup ([…] I'm not talking about unicorns, or decacorns, I'm talking about somewhat earlier stage businesses which are still burning cash), you should take this very seriously, because this capital is under a time limit. They have to deploy the money or give it back within a certain period of time. It is not particularly transparent, but the traditional IPO process wasn't all that transparent either. And this SPAC movement may not last forever, but in the meantime, there is capital available. And if an entrepreneur doesn't take the capital, and he needs it, there is a significant risk that his competition will take it instead, or her competition. So my advice is: take these meetings, look hard at it, realize that it's not transparent, but neither were the IPOs. And if it makes sense for you, if you have to change your business plan versus when you go public, it's not the end of the world.

Rabbit hole/resource to dive into: Learn Skills That College Doesn't Teach You [Link]

I love this Notion docs people put together! The Asking Better Questions section has been immensely valuable for asking questions for my podcast. Launching June 3rd.


Final thought for the week:

Until next week, have a good one!
- Salami


You can find previous issues of Curated by Kalani here. I’m on the web at kscarrott.com and on Twitter @scarrottkalani.

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