#18: Expand Your Time Horizon

The world of startups and football management might seem worlds apart, but they share a common thread: the relentless cycle of building, failing, and trying again. As I grow my current projects, I’ve been thinking a lot about it recently. 

There’s a paradoxical relationship between human nature and success. Humans aren’t patient. We want success yesterday today. And if we don’t get success today, or even worse, we fail, then get disillusioned, and it can put us off altogether if we don’t persevere. 

But success is a cruel mistress. Sure, we’ve all heard of overnight successes. But usually, it’s not the case. It’s the result of perseverance and a shit load of failure. 

It’s a principle that governs us all, whether in business or even sport. And I often use sport as a reference point for many things. A story that embodies this point is of an Italian football manager who took 30 years to reach his summit after many failures.

I want to briefly tell his story before explaining what led me to write this newsletter and how it relates to business.

30 Years Of Hurt… But He Never Stopped Dreaming

Starting his managerial career in 1993, Luciano Spaletti is a manager who always saw the game differently. But despite being hailed as a tactical innovator, introducing concepts like the "false nine" years before it became mainstream, major success in top-flight football eluded him for decades.

Spalletti's first taste of glory came with AS Roma, where he won two Coppa Italia titles and a Supercoppa between 2005 and 2008. However, the big prize - the Serie A title - remained frustratingly out of reach. Three consecutive second-place finishes left him branded as the eternal runner-up.

His move to Zenit Saint Petersburg in 2009 brought two Russian Premier League titles, but many viewed this as a step back from the spotlight of Europe's top leagues. The narrative shifted when he returned to Roma in 2016 and later moved to Inter Milan. Suddenly, Spalletti was seen as outdated; his methods were questioned, and his ability to win at the highest level was doubted.

After leaving Inter in 2019, Spalletti spent two years on the sidelines. There aren’t many football executives who were prepared to take a chance on him. You’d have also forgiven Spaletti for giving up on himself. At 62, many thought his chance at glory had passed.

But Spalletti wasn't finished. In 2021, he took charge of Napoli, a team hungry for success but perpetually in the shadow of northern giants. What followed was nothing short of miraculous. Spalletti moulded Napoli into an unstoppable force, playing a brand of football that left even him in awe.

In May 2023, at 64, Spalletti finally silenced his critics. Napoli clinched their first Serie A title in 33 years, and Spalletti became the oldest manager ever to win the Scudetto. 

His relentless belief and ability to overcome failure led to one of the most beautiful success stories in football management. 

The Uncomfortable Truth We Need To Become Comfortable With

Spaletti’s story is just one of millions of examples. The more you look around you, the more you see it. Success is simple, but it isn’t easy. There’s a big barrier to entry that most people simply aren’t willing to climb.

The barrier is simple. You must forgo your human instincts and exercise patience and insane belief during repeated failures. People don’t usually fail their ultimate goal because of a skill gap. If you fail enough times and continue to work at building your skills, you’ll gain the skill and knowledge to do things right. 

But for many people, micro failures are fatal. After one taste of it, they’re broken. Once bitten, twice shy comes to mind. So they never try again. Or if they do, do they try a second, third, fourth, or fifth time? Can you cultivate an unshakable, almost obsessive belief that “this time it’ll work?”

That’s hard, very hard to do. But if you do it, success, in some form, almost becomes inevitable. That’s what I mean when I say that success is simple but not easy. The principles are there for us all to see and follow in plain sight. But can you follow them?

I remember seeing Paul Graham from Y-combinator estimate that 75% of startups fail. The often quoted number is 90%. Even so, that’s a lot of businesses. Even YCombinator’s failure rate is estimated at 50%. You have an evens shot at making it when backed by one of the world’s most prestigious funds. 

So, failure is almost inevitable. Whether that’s micro failures when growing a business. Or fatal failures when the business just doesn’t work. You need to become comfortable with this truth to achieve anything. But it involves patience and expanding your time horizon. 

And I think many iGaming have very short-term goals. It’s funny that gamblers who take a short-term, high-risk, win-now approach are good for business because it’s not a good strategy. But many businesses in our industry operate this way, too. 

For example, I speak about it all the time. So many cookie-cutter products with a focus on short-term marketing channels. They are so gripped by the fear of failure that they take the easy “quick-win” option, which ultimately never really amounts to anything significant.

Compare that to a business like Stake, who has shown the possibilities if you take a longer-term approach and invest in creating a great product and building a killer brand. 

Practical Strategies To Make Failure Your Friend

So, in my pursuit of learning to embrace failure, I did what I always do and searched for how to upgrade my mental models to better approach it. Especially as I’m not involved in 8+ businesses where it’s almost guaranteed that I’ll experience many failures, big and small. I needed to learn how to better deal with it to keep moving forward.

Here are four concepts that I liked and hopefully are also helpful to you:

#1: The Demoralization Trap:

Often, it's not running out of money that kills startups – it's losing hope. Most don’t die mid-sentence. They die by death of 1000 cuts. Each failure leads to compounding demoralisation until all hope has left the organisation. 

One effective strategy is to focus on small wins. In the early days of Blask, we celebrated every new user sign-up and every positive piece of feedback. These might seem trivial in the grand scheme, but they provide vital emotional fuel to keep going.

#2: The Iteration Mindset:

Initial failure is almost guaranteed. The key is to iterate rapidly. Launch something, anything, and improve based on feedback. Things will break, and users won’t like certain aspects. But move fast, break things, and rebuild them better.

It really helps if you find a core group of users who believe in your vision and truly love your product. This "love" from early adopters can guide your product development and provide the motivation to keep going when times get tough.

#3: The Focus Imperative:

Distractions are startup killers. There are so many things you could be doing. You will have 100s of exciting, tempting ideas every week. You’ll second guess whether the shiny new opportunity is better than your existing one.

We’ve all seen it. We’ve all felt it. But the opportunity hoppers usually never succeed. Why? Because they don’t allow themselves the possibility to fail naturally. So they never allow themselves the opportunity to succeed, either. They don’t see things out to completion, they jump ship before the market has decided whether the value you’ve brought to the world is worth their attention. 

#4: The Public Accountability Hack:

This is one of the hardest because what’s worse than failure? Being seen to be a failure. So if you make your goals public, you face the ultimate lizard-brain humiliation. But let me tell you, speaking publicly about what I’m up to, the goals I’m aiming to achieve… while scary, they’re the biggest motivator and source of accountability I could have found.

It’s not just public accountability, either. But sharing goals with my mentors helps keep me on track when the little voice in my brain is growing frustrated that I’m not moving fast enough or we’ve encountered a failure of some kind. 

Conclusion

Success in all walks of life, whether in football, entrepreneurship or even learning a new skill, comes to those with the longest time horizon and who can endure a lack of success the longest.

So don’t be discouraged by setbacks. View them as data. Quickly take the lesson and move forward.

The goal for us all in our quest for success is to avoid the death of our dreams. If your dream doesn’t die, you might just get rich (or win a Scudetto).

So my question is… how long are you prepared to stay in the game to achieve it?