#18 G(OLD)EN OPPORTUNIES

One of the most interesting questions I received when I started this newsletter asked me for thoughts on how to think about C-Somethings as they (we) age.  

Specifically, when (if ever) is it a good idea to invest in an older founder?  

It's a good question, and I'm incidentally close to it. Since last year Publera is investing a non-trivial amount in a first-time founder who's a 44-year-old cowboy. Why? I'm pretty convinced he has the curiosity and commitment to do better on his thing than any 20-something Stanford grad ever could. 

On the other hand, would I like to get some royalties on a Stanfordboi's future earnings? Like whipped cream on watermelon hell yea!! Way safer bet.

So how do you know when to take a flyer on the result-of-time (wisdom), versus the abundance-of-time (compounding)?

It’s also been on my mind for the last few months because I’ve been helping my friend Bianca Valenti articulate her thoughts on a similar topic: how to adapt your physical and mental training to the reality of an older self.

Bianca is a world champion big wave surfer, and her journey into “age-adapting” for surfers had two catalysts.  

One, she helped Lionel Conacher become the oldest person to surf Mavericks for the first time. I’ve gotten to meet Lionel a few times (and I’m sharing this with his permission). He’s inspiring. 

Conacher has been a world-class skier, a decathlete, and Olympic hopeful. He’s also a successful C-something. He’s an investor, advisor, husband, and is officially a "rad dad." (I have some socks which say I belong to that last group, so I know what I'm talking about). 

But what's inspiring about Lionel is really his mind. More on that below. (In the meantime, here's his take on sending Mavs at 59 if you’re curious.)

The second catalyst for Bianca's work has been age itself. 

At 39, she’s considered “oooold” for a professional surfer. Yet she’s winning more awards than ever, consistently breaking her own records, and–most importantly–seems to be the happiest she's ever been.

What gives?  And what can surfing teach us about how to identify (or become) high-performing elders?

The first thing Bianca advises aging surfers is to actually spend less time surfing. It's counterintuitive, but it works.  

For a kid or 30-something, success requires you to spend as much time in the water as possible. Getting in the reps. Building muscle memory. Or, if you’re a founder: working till 2 AM, waking up at 6AM, and doing that again. Every day.

Bianca's advice for older surfers is to block more time for maintaining mobility. This means exercises that activate the full possible range of every muscle.

That’s because things always fail first at the outer ranges of motion.  From shoulders to sales teams.

The analogy for you is to constantly do this with your mind. Practice movement in all of the outer ranges of what your brain can do. Learn new stuff, and push your own limits on the old stuff you thought you had dialed.

Easier said than done. It’s a seductive trap to just do fewer hard or new things as you get older, mainly because you don’t have to. Avoid that trap. Or, invest in people who do.

The next critical aspect of age adapting is to have very EFFICIENT sessions when you surf. You’re not in the water as long, but you surf better while you are. In Bianca‘s words, make sure "you finish your session with your batteries still charged." 

The fact is, at some point restarting takes longer than resuming. And this requires more of a mindset shift than process change.

Unfortunately, it might be the hardest mindset change you can try, because one big effect of age is realizing how little time you have left. It makes sense you’d want to surf 2 hours instead of 30 minutes.

Yet, when you factor in the downtime you’ll have from overextending, compared to the volume and quality of efficient sessions, it works out in your favor. It’s very hard to win from the weakling list.

The same thing is true for founders and C-somethings.

Any parent will tell you that if you think you're an efficient user of your time before kids, you'll have your mind blown after. You'll wonder what on earth you ever DID with all that time you had.  

(Some days, I get more done in 7 hours after two kids than I used to in 7 days. Breeders among us know what I’m talking about here.)

So if you are evaluating a founder who seems closer to the age of an investor, these are the questions you should focus on:

How well do they exercise the full mobility of their mind—curiosity, commitment, seeing in new ways?

And how good are they at efficiency of their efforts? They should be much more efficient than the 20-year-old version of themselves, obviously. 

The formula to measure that is impact per unit of giving a crap.

For what it's worth, my friend who asked me about this happens to have the exact same problem I do:

He's a regular (very handsome) dude, who used to be young one, and soon will be an old one. But right now, he works for C-somethings who are his elders (investors) and advises and manages C-somethings who are his juniors (the founders they fund). 

Here we are, (handsomely) in the middle, like that's an age or something. So it makes sense to think more like investors than founders.

But how do you improve your own performance in these conditions?

One of the things I find interesting about young people is I can tell them some platitude like “REPEAT YOURSELF,” and they hear it like it’s some motivational poster on the wall of their high school hallway. 

Meanwhile, if I tell that to an elder executive or founder, then they think about it for a week, make substantive changes to their strategy, and reap the rewards. 

Did my advice really make a difference?  Not a bit. What they changed is their mindset. 

Bianca agrees. She points out that as we get older we have much more facility controlling not just our own emotions, but our entire point of view. We have more control over the way we see the world around us and the problems it presents. 

In fact, I admire, support, invest in, and feel lucky to work with Bianca NOT because she wins awards surfing waves taller than my very-tall house, but because this happens, and she keeps doing it.

As you age, you can constantly try on different glasses for seeing the world (if you want). Young people have new glasses, but aren’t as good at changing them.

Conacher said to me once that he was intrigued by Bianca because she's 1 of only 2 surfers who paddle out to Mavericks every day, regardless of the conditions. (The other is also an elder god of big-wave surfing, Grant Washburn.)

In Conacher's telling, and as a seasoned investor, he could see whatever attitude they share about getting out there is now key to their success. Or, in Bianca‘s words, "all conditions are good conditions."

To young people, this is just more motivational poster.

But to Bianca it's a mindset shift that catapulted her across the chasm of young world champion to elder world champion. She now excels in the wildest scenarios there are, because she likes them.

Translation: she has a home-court advantage on any wave in the world, in any weather.

What does this mean for founders? Basically, all bad news is good news. If you find out your product sucks, you just change it. And you change your whole POV, theory of the market, hiring, firing, and/or messaging.

In startup-land, we call that a "pivot." 

(Young founders pivot all the time, but one funny thing I've noticed: it’s almost always after someone much older advised them to.)

A final thought while I have Bianca‘s permission to speak freely: over the last few years we've also helped sharpen her corporate speaking on the topic of RISK. 

One of her salient points on that is you minimize risk not just by planning on it, but by planning for it.

The difference is a mindset and a process. The mindset is you take risk with intention. You remember it’s your choice, not your situation.

The process is just identify what pain you’ll feel when it doesn’t work out, and find ways to feel it ahead of time.

McKinsey has a word for that—it’s called a stress test. But my Grandma uses a different one: Practice.

And it can make you perfect,
Jesse

PS: If you want to get in the lineup for Bianca's age-adapting coaching or have her talk to your board or team, the best way to do it is just DM a note and I can get you connected. (She gave me permission to offer that).  The second best way to be in her loop is join her mailing list here.  She sends a weekly update with coaching tips and will always mention if/when a new program launches.

PSS: Why do I think age plus communication matter more than anything else, or say, age and engineering?

Bill Gates himself is proof. Communication is one of the ONLY things you will do your entire life. Better get better now, since you’ll still have to get better later.

PSSSSSSS: Send this issue to any of your pals who think there might be alpha in looking at founders over 30. Or, to anyone who surfs big gnarly waves!