5 Principles for Making Big Bets in Business (Without Blowing Yourself Up)

G’day Founders,?

We all know the feeling. You’ve hustled your guts out to get your business where it is today. And now... surprise, surprise... you’re staring down your next Big Bet. Maybe it’s a major investment, an acquisition, or a bold personal move... but suddenly, your brain’s running a full risk assessment at 3 a.m. (Cheers for that, brain.)?

Why? Because Big Bets come with big risks. And if you’ve already taken some huge swings to get here, you definitely know how much it can hurt if you get it wrong. (Fun times, right?)?

But here’s the thing: growth and freedom never come from playing it safe but rather from taking smart, calculated swings. Because ‘waiting for the perfect moment’ usually means waiting... and more waiting... until someone else takes the shot you should’ve.?

In my latest ScaleHQ podcast episode, How to Take Big Bets in Business & Life (Without Blowing Yourself Up) (scroll to the bottom for the YouTube link if you missed it), I shared 5 principles I’ve learned from my own Big Bets, including the time I acquired a $35m business and the slightly insane decision to move my entire family (and business) to Cyprus.? Both were high-risk, high-reward plays. And both taught me the same core lessons.?

So, if you’re staring down your next big move, wondering if it’s genius or madness... keep reading because these 5 principles might just help you swing hard and land on your feet.?

1. Big Bets Have Big Trade-offs?

Let’s be real. Every shiny opportunity has a price tag. Sometimes it’s money, but more often than not, it’s your comfort, sanity, or weekends, (usually all three.) But here’s the kicker: the bigger the bet, the bigger the trade-off.?

When I packed up my life and moved to Cyprus, I left behind everything familiar and comfortable, like my network, my routines, and even my friends, which was scary. But what I gained was the adventure, freedom, and a whole new perspective on life and business.?

Most people get stuck in the daily grind because they’re too focused on what they’ll lose, not what they could gain.?

I made peace with the trade-off: predictable comfort vs. an exciting, travel-filled life and a shot at something bigger. And guess what? No regrets.?

Key Takeaway: Before your next Big Bet, ask yourself: do you fear losing more than you value winning?

If the answer’s yes, you’re letting fear drive the bus (aka the worst driver, who loves a detour and hates a shortcut). The reality is that playing it safe is often the biggest gamble of all because safe bets rarely lead to big wins. They lead to stagnation, regret, and a front-row seat to someone else living your dream.??

Remember, every big opportunity comes with a cost, whether it's time, money, or comfort. But what’s the cost of not taking it? A business that never scales? A life that never stretches? A nagging "what if?" that keeps you up at night. So, weigh it up properly because one thing’s certain: regret loves playing it safe. Growth comes from swinging big, even if you miss.?

2. Reverse-Engineer the Risk?

Most Founders get stuck on a Big Bet because they’re too focused on what could go wrong without actually mapping out what that looks like. Fear thrives in the unknown. The best way to shut it down? Get crystal clear on the worst-case scenario.?

When I was considering buying my first business, a $35m company making just $100k in profit, I had to face the brutal what-ifs. What if revenue dropped 5–15%? What if costs blew out? What if we couldn’t turn it around??

Instead of spiraling, I ran the numbers. I mapped out exactly how far we could cut expenses, what we’d need to fix first, and how we’d keep it afloat if things got ugly. That gave me the confidence to move forward.?

"What’s the worst thing that could happen, and can I live with that?"??

Turns out, when you actually define the worst case, it’s rarely as bad as it seems in your head.?

Key Takeaway: Big Bets aren’t about blind optimism but about calculated confidence. If a move feels risky, don’t just worry about what could go wrong. Reverse-engineer it.?

Start by defining the absolute worst-case scenario. What happens if everything goes sideways? Can you survive it? Then, map out the best-case scenario. What would success look like? And most importantly, what needs to be done for this bet to pay off??

The difference between a reckless and smart risk is a plan. So, before you say no out of fear, make sure you’re not just scared of a problem you haven’t defined yet. Remember, uncertainty will paralyse you. But clarity? Clarity gives you the green light.?

3. Mitigate the Downside?

Hope is a great motivator but a terrible strategy. The smartest Founders don’t just prepare for the best; they fortify against the worst. Big Bets come with risk, but the goal isn’t to avoid it entirely (good luck with that). The goal is to reduce the chance of failure.?

Before moving to Cyprus, I spent a full year restructuring ScaleHQ to run remotely. I shifted all client calls to afternoons so the time zones would work. I set up new tax structures, built local networks, and even did a six-week recce to test the waters.

By the time we actually moved, there was no blind leap, just a well-executed plan. Of course, there were bumps (because when does anything go 100% smoothly?), but by preparing ahead, we turned potential chaos into manageable challenges.?

What I’m getting at is that I used the same approach with my first business acquisition. Before we even signed the deal, we had a detailed 100-day execution plan covering cash flow and legals, leadership changes, operational fixes and so on. By the time the ink dried, we already had a plan in motion.?

Key Takeaway: Mitigating risk doesn’t mean avoiding it; it means controlling it. And the best way to do that? Prepare before you jump.?

Before making a Big Bet, take proactive steps to mitigate the downside.??

The difference between a strategic risk and a reckless gamble is simple: preparation. So, plan ahead and you won’t need luck.?

4. Don’t Wait for Perfect Conditions?

If you’re waiting for the stars to align, you might want to pack a lunch because it's gonna be a long wait. Perfection is a myth. Progress happens when you take action, not when you sit around debating every possible way things might go wrong.?

When we considered delaying our move until my son finished school, we realised we’d be robbing him of the international experience we actually wanted for him. There was no perfect time, so we acted. Imperfectly but decisively because waiting for the “right moment” usually just means waiting until you talk yourself out of it.?

Key Takeaway: If you're holding off on a Big Bet, ask yourself: are you waiting for certainty or just avoiding discomfort??

Because certainty is a unicorn. And discomfort? That’s just the toll you pay for doing something that actually matters.???

Instead of waiting for the “perfect moment,” set a deadline. Define the minimum conditions you need to move forward, then commit. No overthinking, no second-guessing, just action, because the longer you wait, the easier it is to convince yourself to do nothing.?

5. Fear is Normal... But It’s Not a Red Light?

Fear has a habit of showing up right when you’re about to do something big. Convenient, isn’t it? You’re finally about to take the leap, whether it’s to make the investment, sign the deal, or expand overseas, when suddenly, your brain turns into a 24/7 worst-case-scenario generator.?

When we moved to Cyprus, I wasn’t fearless. When I acquired my first business, I wasn’t fearless. But I didn’t let fear make the call. That’s the key difference between successful Founders and those who stay stuck. The best ones feel the fear, use it as fuel, and move forward anyway.?

Key Takeaway: Fear doesn’t mean you shouldn’t do it. It means get ready. If a Big Bet is making you nervous, don’t just sit in the anxiety; instead, channel it into preparation. What’s making you uneasy? What can you control? What steps will give you more confidence??

Fear thrives in uncertainty, but action shuts it up. So, don’t wait to feel “ready.” Prepare, take the leap, and trust yourself to figure out the rest.?

So, what’s your next Big Bet??

Maybe it’s an acquisition, launching a new product, or expanding overseas. Maybe it’s something completely left-field that scares the hell out of you (which probably means it’s worth doing).??

Whatever it is, don’t just sit on it; run it through these 5 principles.?

If it holds up, you’ve got your answer. If it doesn’t, you've got a plan to strengthen it. Either way, progress beats paralysis every time.?

Your move.??

Thanks,?

Sean?

?? Missed my last podcast episode? Watch it here:?

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