What Las Vegas Taught Me About Winning in Life & Business

I went to visit a friend last weekend to see his new apartment and have a chat. Beautiful apartment. Duplex, great views of Downtown Dubai.

But the highlight for me was the backgammon set, prominently on display, that I couldn’t resist challenging him to a game on.

3 games actually. I won them all. Obviously, he called me a lucky gambler, so I guess we will have to see what our next meeting brings!

I don’t play much anymore as I don’t know many people that play in Dubai, but rolling the dice brought back great memories for me of the 5 years I lived in Las Vegas playing poker every day, along with the years that followed playing back in England too.

I spent many years playing, studying, improving, and learning about life by watching the unique characteristics of gamblers.

Some of the strategies I use in business today have come from those days, and whilst I can identify them myself when I use them, I have never sat down to really analyse all the learnings from the experiences I had.

If you are reading this and thinking that you won’t be interested because you either don’t gamble or don’t understand certain casino games - don’t worry! There are going to be plenty of takeaways for your business and your life.

And if you think poker or backgammon are not games of skill, then think again!

When you read to the end of this, the way you assess information, make decisions, and deal with adversity should never be the same again!

🍀 Luck Dissipates Over Time

Why Strategy & Volume Will Always Beat Short-Term Luck

Some people may always seem lucky. Some people may always think of themselves as lucky. But mathematics doesn’t lie! The simple fact is that a person's ‘luck’ dilutes as time goes on and volume increases.

If you are doing something right, then the law of big numbers will always play out in the long term.

In business: Strategy + Volume = Success.

For a gambling related example, let’s imagine that you have the chance to bet £10 on the roll of a dice. If it lands on 1, 2, 3, or 4, you win £10. On a 5 or 6, you lose your bet.

That is a bet you want to take all day long. You have a 66% chance of winning and only a 33% chance of losing.

But it is still possible to have a bad session and throw nothing but 5’s and 6’s—leaving you a heavy loser. Or, as some would say, unlucky.

With a winning proposition like that, the key is you want to play the game for as long as possible. Probability and the power of big numbers play out in the long run. With a winning bet (the right strategy), success is ultimately guaranteed.

And even more importantly, you don’t need a bet that has such a high edge like the one in my example. Just a 1% edge, played out for long enough, compounds into life-changing returns.

🎲 Only Play When The Odds Are In Your Favour

How Value-Based Decisions Lead to Long-Term Success

In the poker world, this means that if you are looking for a card to win the hand, you should only put money in the pot where the money you stand to make from winning outweighs the probability of not getting the card you’re looking for.

As an example…. you are in a position where drawing any card that’s a heart on either of the last two community cards will almost certainly win you the hand.

This scenario gives you about a 34% chance of getting the card you want and winning the hand.

If there was £100 in the pot prior to you taking a card and it would cost you £50 to call the bet and continue, then you are risking £50 to win £100.

That is a 2/1 payout on your ‘investment’ of £50—a 200% ROI.

As great as that ROI may sound, you only have a 34% chance of hitting the card you need, so you need a return much higher than 2/1 to make this a profitable long-term play.

I say ‘long term’ because, as you saw earlier, short-term luck can play its part, but in the long term, the maths always wins.

If you keep making bets like the one in this example, you are guaranteeing you go broke over time.

You need to be looking for value. The right plays. Putting your money in places where the potential return outweighs the probability of loss.

Make data-driven decisions, and sleep well at night.

🎯 Losing Is Part of The Game

Why Short-Term Setbacks Lead to Long-Term Wins

If you have understood the previous two points, you will know that you are going to lose at times. And that is fine, because as long as you have an edge, you know that these losses are short-term, and you will be a winner in the long run.

But analysing losses is also essential to ensure the same things don’t happen again and that you can improve your edges for the future.

Embrace the losses, and don’t let them dishearten you—as long as you know you made the right decision at the time and learned something for the future.

In poker and in life, you want to be playing a game with an infinite time horizon. The losses more than even out and success is ultimately guaranteed.

📊 Information Is Power

Poker and business are games of information. There are countless data points at play, and the more you can analyse, the greater you can make your chances of winning.

In poker, you should be looking at data like the position the opponent bet from, the amount they bet, what they did when someone raised them, how quickly they acted, etc.

In business, it is things like conversion rates, click-through rates, cost-per-acquisition, demographics, and purchase history.

You must always be collecting as much data as possible, analysing it, and adapting your strategy according to what the data says.

With business or poker, if you aren’t paying attention to the data and using it well, then you are reducing any edges you may have and pushing yourself further away from success.

🎭 Play The Player - Not The Cards

In poker, only 25% of hands are won by getting to the end of the hand with the players turning over their cards—a showdown.

That means 75% of the time, a player wins not by necessarily having the best hand, but by making the other players think that their hand isn’t good enough to carry on.

In business and in life, the reality is that there are always going to be people and competition who are stronger than you, better funded than you, and more experienced than you. You can obviously train and improve to reduce that gap, but your real edge is your creativity and your courage.

That is how David beats Goliath. ‘Not a lot’ can become ‘just enough’ in the right hands.

💼 Use Your Image To Your Advantage

In poker, players have what is known as a table image. This is the way they are perceived by others. It could be a cautious image, where people think a player will only play hands when they have the best cards. It could be an aggressive image, where people think of the player as reckless and happy to flippantly throw money into the pot.

How people are perceived affects the decisions that other players make against them. Weak players will allow themselves to be bullied by stronger players because they are scared. Good players will fold a great hand when a player with a tight image is betting aggressively out of character.

Taking this to business, brand is everything. A strong brand attracts customers and investors; it can even scare off other companies from wanting to compete.

Companies with a reputation for excellence or reliability can leverage this perception to negotiate better deals, enter new markets, and influence stakeholders more effectively.

🃏 Folding Is Nothing To Be Ashamed Of

In poker, you can’t win by playing every hand, and in business, you can’t make money by chasing every opportunity.

A good poker player will spend the vast majority of their time sitting around, watching, observing, and analysing. They won’t be playing many hands and will be putting minimal amounts of money in the pot.

They are folding their hand and losing the smallest possible amounts of money, ensuring they have enough bankroll left to have the firepower to get involved in the hands where they have the maximum chance to make big money.

And business is just the same. You can’t invest in every opportunity. You can’t say yes to every deal. You have to sit back, learn as much as you can, keep your powder as dry as possible—and then pounce when you see that all the stars are aligned.

Being too hungry to chase every opportunity, regardless of quality, is a surefire way to go broke—fast!

💰 Stack Size Matters

In poker, when you have a big stack of chips in front of you, you should be playing a very different game compared to when you’ve been whittled down to a small stack. A big stack lets you be a bully—the aggressor who pushes the rest of the table around, leveraging the size of your stack and building it even more.

The opposite is true as well. When you have a small stack of chips, you need to protect them and be incredibly selective about when you use them. There will be no room for error.

The same logic plays out in business too. Companies with dominant market positions and large capital reserves can push their competition around and take them out of the market with ease. Having lots of resources (a big chip stack) allows businesses to try new markets, take risks on new employees, and put even more capital behind strategies that are working well.

A company with few resources and a tiny bank balance is always running scared. They can’t take advantage of opportunities when they present themselves, and they can get taken out of the game with ease by a bigger, more aggressive competitor.

🛡️ Contingency Plan and Always Leave Yourself Outs

In poker, a good player always has ‘outs’. That is to say, if they have put all the chips on the table, they want to know there is at least one card still left to be drawn that can make them a winner.

If their opposition has a better hand already and there are no more cards available that can improve their own position, then they are dead in the water.

In business, these ‘outs’ are your plan B (or C, D, E!). What are your options to make money if the first plan doesn’t work out. Or what is your option to ensure you don’t go broke if the original plan doesn’t work out.

A lot is spoken by people who tell you to go all-in and chase your dreams. Yes you need to be fully committed to something, especially when all the odds are in your favour, but you don’t want to be in a position where if it goes wrong you are totally wiped out and unable to do anything else ever again.

I never got to live my dream of being a full-time poker pro. I could consistently make money—not lose it—but not the amounts of money I could make in business.

And quite simply, that is because I wasn’t good enough. I could beat the tourists and the hobbyists, but the amounts of money people played for in those games weren’t huge. Sure, I could make 1k, 2k, or 3k in a session, but that pales into insignificance when you look at the equity I could build in business if I spent the same amount of time on it.

And when I moved up to higher stakes, where the money would be enough to interest me, the players were so much better than me, and I was guaranteed to be a long-term loser.

But that is the key lesson for me here: pick your spots. Don’t get involved in situations unless you have the advantage. And when you do, milk it for all you can.

See you next week,

♥️ Matt ‘Royal Flush’ Haycox

🎙️This Week On The Pod!

This week on No Bollocks with Matt Haycox, I’ve served up two game-changing episodes you simply can’t afford to miss!

🎙️ Daniel Priestley: From 21-Year-Old Entrepreneur to Multi-Millionaire Business Builder
In this episode, I chat with Daniel Priestley—entrepreneur, best-selling author, and the man who turned personal branding into a business weapon.

🔥 Key insights you’ll gain:

• Why personal brands trump company brands (and how to leverage yours)

• The four-product ecosystem that can triple your business revenue in one year

• Why your job as a CEO isn’t to work—it’s to create demand

🎯 This is for you if you want to transform your business, build influence, or figure out how to scale without losing your sanity.

💥 Rob Moore: The No-BS Blueprint for Wealth and Freedom
I bring in Rob Moore—serial entrepreneur, property expert, and podcasting dynamo—to discuss everything from the UK’s economic chaos to why work-life balance is a lie.

🔥 Here’s why you’ll love it:

• Learn the truth about demand generation—the #1 job of any entrepreneur

• Why the UK is trading insolvent (and what Rob thinks should happen next)

• The myths of “balance” and why merging life and work is the ultimate hack

🎯 If you’re tired of the noise and ready for straight talk on building a future you love, this is the episode for you.

🚨 Don’t miss these episodes. These are the conversations you’ll look back on as the turning point in your entrepreneurial journey.

Team Talk 💪🏼

Every week someone from my team hijacks this section of the newsletter to write about a must have strategy or tip that they have been implementing within our businesses.

🔫 Firing! (And hiring)
Stef Thompson, Head of Finance

I know this section normally contains a tool or new strategy, but I want to use it to talk about something that ever business owner, manager or team leader has to contend with at some point……. An underperforming team member, and firing them.

2025 has started with a big change in my team. A long overdue, and much needed one!

We have recently welcomed a new Finance Executive & Data Analyst  and sadly had to let go of another member of the team. Long story short, they just weren’t up to scratch for the role and I should have made this decision months ago.

But because they were a nice person, and I hate firing people (!), I did what I think many business owners and managers are guilty of, and avoided dealing with the problem head-on and kept them far longer than I should.

I have definitely leant my lesson for the future this time. When it comes to having the right people in your team, you simply can’t hang around if someone is not right for the role.

The knock on effects of "giving them another chance" are disastrous. We ended 2024 behind with targets and full of stress.

For anyone, like me, thinking that you are being nice by hanging on to underperforming or unsuitable people, it actually really isn’t the case. By doing so you are not only neglecting other team members, as too much time and energy goes in to dealing with the problem person, but you are damaging moral, killing your sanity, allowing people to think that underperformance is acceptable, and also holding the unsuitable person back from finding a role they are more suited to elsewhere.

Roll forward 2 weeks after changes were made and the difference is amazing! A productive and happy team firing through the backlog and set to be reaching targets again in coming weeks.

So, as Matt says, learn from my mistakes so you can reduce your own! If a team member isn’t the right fit for the role - act fast!

Want to work with me? Need my help?

I’ve been where you are—struggling with decisions, distractions, and scaling pains. Whether you need clarity on your next move, help building a strategy, or funding to fuel your growth, I can help.

Here’s how:
📞 Coaching with me: Real, no-bullshit advice tailored to your business. Book a 15 minute power coaching call here.
📈 Work with my marketing team: Build a brand that gets results here.
💸 Get funding: Access funding to scale and thrive. Click here.
🎙️Podcast with me: Let me intro you to my audience and blow up your brand! Click here

💡 Let’s cut the bollocks and get to work. Book a call today, or reach out to my team, and take the next step toward making your business unstoppable!