One of the toughest challenges of scaling a startup post product market fit is scaling the talent.

Some talent have to be imported, some can be grown/scaled.

The problem is that not everyone truly wants to level up. That’s unfortunate but also fine. You need to identify who truly wants it and who doesn’t.

Some would look at it as “who’s capable of scaling” but I call bullshit on that. Everyone can scale if they truly deeply want it. If you think otherwise, then it’s the Tyranny of Soft Expectations.

Anyway, assuming some of the talent that were with you in the early days truly want to level up, you will still find it very challenging to scale them (or help them scale). The initiative should come from them, but you must show them the way as the ‘coach’. “Here’s what winning looks like, and in your position, here’s what I need from a super star player.”

I’m willing to bet that although scaling someone is the seemingly more challenging/time consuming endeavor, it’s the more rewarding one, by far.

There’s a compounding effect when people who have been around for a long time stay.

Context compounding: I know that we tried X thing Y years ago and this was the conclusion.

Relationship compounding: trust, credibility, and relationships are very underrated factors that supercharge someone’s ability to execute. If I built those 3 years ago, I can move 10x faster today.

2 problems:

1. Lag effect: it takes people a while to realize that they have changed in role and responsibilities, and even how people perceive them has changed
2. Imposter syndrome: am I really good enough to do this? Usually bullshit that our minds tell us. This is especially true for people who are harsh on themselves, who coincidentally also happen to be the highest performers/achievers as they demand the most of themselves

Of course, although I’m discussing the benefits of this, there are also challenges/issues with it.

It’s healthy to have a mix of existing people that are challenged to scale as well as a group of people who are experienced that are brought in. If anything, when you bring in some experienced team members, everyone’s challenged to play better. Sometimes, you have to show a league 3 player leveling up to league 2 what a superstar league 1/2 player looks like in order for them to know who they should play like.

Imagine having a million dollars to invest. It’s all the money you have to invest for the next 5 years, and you can only invest it in 1 place. How much time will you spend in researching the best place to invest it?

Probably a lot of time, maybe 6 months at least, no?

Everyone who wants to start a business doesn’t think that way, although it’s the exact same thing.

Most people invest <5% in thinking through what they want to do (myself included), and then get to work immediately. I’m realizing that that’s just stupid.

I wrote an updated version of this here: Business is a Sport

I’ve recently adopted this analogy of business as a sport/game, and it’s been a game changer! (pun not intended)

I’ve heard this in a few different places along the years, but never truly understood it until now. One of those resources was Mark Cuban’s book: How to Win at the Sport of Business.

Here’s how/why looking at business as a sport/game has changed the game for me:

1. It allowed me to be unapologetic about wanting to win. Most people don’t get why I’m very harsh and adamant on certain actions. The reason why is because I want to win! Not everyone wants to win as much in sports. The best players in the world are those who are both obsessed enough with winning, as well as in love with playing the game itself. They’d do it for fun, they’d do it for free, but they also really want to win.
2. Bet on the best players: sports teams bring onboard the best players. They’re unapologetic about letting go of a player that is not bringing their A game, whether by sitting them on the bench, or getting rid of them entirely. Our social world views firing a team mate as cruel in the world of business. But once you look at it like a sport, and add to that the desire to win, it’s no longer personal. You must help me win. If you don’t, you’re useless. If you get in the way, I must bulldoze you out of the way.
3. The rules of the game: basketball is simple; get the ball in the hoop within a time limit. The team that does that the most wins. The rules of business are complex. It may even seem like there are no rules! It’s such a complex sport/game that people don’t even realize that it is. But it is.
4. Leagues: there are 10s of different leagues in any popular sport. Just because you’re good at a particular league, doesn’t mean you’re done growing. The best player/team is the best one in the best league globally, not locally/regionally. Most people in business get stuck at a particular league/level. Wanting to be the best in the game of business means that you want to be the best globally, and play in the best league. Being the best basketball player in the French league is not the same as being the best player in the NBA. Being the best player in the sport of filmmaking in Dubai is not the same as being the best player in Hollywood.

So, this is good enough to understand why the analogy is really helpful. But what are some rules/principles of the sport/game of business?

Principles

1. Build something people want (product market fit)
2. Make sure there are a lot of people that want it (aka pick a big market)
3. Reputation is everything (brand)
4. Money is the score: business is about solving a problem for a customer. In the process, the customer rewards you for your services. Just how in basketball the score is how many balls you got in the hoop, in business, the score is how much money you managed to keep from the customer. If a customer pays you $100, and you keep $20, and you get millions of customers to do the same repeatedly, then you’re winning. Business has many sub-sports (industries) and leagues (markets). The winner in the sport of the sportswear sport in the global league is Nike, because they take & keep the highest number of dollars from customers in that industry & market.
5. Team culture: business quickly becomes a team sport after a founder starts it. If a basketball team has turbulence in relationships, they’re unlikely to win or keep winning.
6. Continuous winning: winning 1 championship is one thing. Winning the championship every year is another.

Other analogous thoughts:

1. Rest, recovery, and seasons
2. Captains, coaches, managers, and owners
3. The best players get paid the highest (scorers more than defenders)

Unlike basketball, business is a mental sport.

1) you need to overclock your brain to make a startup work. That in turn causes an almost definite case of ADHD. Good luck dealing with that.

Football athletes overclock their bodies (at least compared to the average individual) in a certain way that make them superior at the sport. Startups are mental sports. The rules of mental strain (as opposed to muscle strain) are a lot less clear. In physical sports, we put together a team of individuals whose only goal is to optimize and maximize the success chances of such high performance team. Such a shame that this is not even close to being a common practice in the mental sports of startups.

2) any fast change is expensive for the mind to grasp. We evolved over generations, so for someone to go from 0 to 180 very fast in such a short period of time, also creates a crazy lag effect (working solo to leading a team of 100, survival mode to thriving, poor to rich). Your conscious and subconscious are not in sync. That’s problematic

The mental frameworks and models that made you successful in the early stages of a startup (survival mode mindset) are likely to guarantee your failure if you don’t adapt them to the new reality of the company once things start working (post product market fit / financial stability of the business).

Be willing to withstand short term suffering for long term gain.

There’s this concept/framework of ‘switching hats’ that I’ve learned by observing a few people who use it.

We all play different roles in our lives.

I’m a son, a friend, a boss, a brother, a partner, an employee, and many more.

The framework of ‘switching hats’ gives you the lenses that allow you to look at yourself as having more than one persona.

Being a mother who’s nurturing and supportive might mentally make you feel like you shouldn’t be disagreeable and stern on a business matter at work. But why not?

Those are different hats. You can wear the mother hat at times, and you can wear the boss hat at others.

Not switching hats could often mean that you’re in a compromised position.

I’ve been asked this question a few times lately (in nicer ways), so I thought I’d answer it for everyone.

I’ve also asked this question to a couple of product managers to see what they thought their job was.

I think a lot of people don’t understand what a product manager is or what one is supposed to do.

So let me tell you.

First of all, why is this important?

I’ll tell you why.

Startups are started by founders.

Those founders often play the role of a ‘product manager’ at the beginning.

So without this role, startups don’t start. We must be grateful for when a good product manager is in place with good engineers/designers, as magical things happen.

Okay – here’s the story:

Winning as a company may seem like a complex concept, but in reality, it is extremely simple on the surface. It only gets complex once you’re a couple of layers in. Hear me out.

Writing this as a reminder for myself.

Doing the ‘right thing’ is almost never celebrated with approval and cheers.

It helps to remember that this is a timeless fact. Below is a 2,000 year old text that describes it well.

When faced with a difficult decision, it is usually not the lack of conviction that make you clench and slow down on taking the action, but rather the subconscious thoughts of the consequences.

We are social animals. Inside of every one of us is a little desire to be a people-pleaser. When we make tough decisions that we believe in but others may not understand, we may get ‘punished’ with judgement, criticism, or resistance.

This text from Seneca’s letter #29 helps me remember that popular approval shall not be craved, and tough decisions will almost always not be applauded.