120 — How to Take Big Bets in Business & Life (Without Blowing Yourself Up)
This week, I’m unpacking how to take Big Bets in life and business without risking it all. Big risks can lead to big rewards, but only if you know how to protect yourself from worst-case scenarios. Listen and learn how to make high-stakes decisions with confidence and control.
In today’s ScaleHQ podcast episode, I unpack my tried-and-tested five-point framework...the exact principles I’ve used time and again to make Big Bets that have paid off without blowing myself up in the process.
This episode was inspired by the Founders I know who have taken big risks to get to where they are, whether it was starting a business, making a major investment, or making a massive life change. These decisions aren’t just one-offs. They’re repeated turning points that can dramatically change the course your scaling success.
But here’s the challenge: when the next big opportunity comes along, many people, including Founders, hesitate, caught in the "what ifs." And while the fear of getting it wrong can be paralysing, but only if you let it.
What you’ll learn in today’s episode:
This episode covers five key principles:
- How to weigh up big decisions and assess trade-offs, so fear doesn’t hold you back
- The worst-case vs. best-case scenario approach, and how to reverse-engineer risk before committing
- How to mitigate downside risks during the planning phase, so you can minimise the risks in your business decisions
- Why waiting for “perfect conditions” is a trap, and how taking action creates clarity
- How to tell if you’re making a calculated risk or a reckless bet, and what to do about it
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If you’re at a crossroads in your business or personal life, this episode will help you weigh up the risk, prepare for the leap, and take bold action with confidence.
ABOUT OUR GUEST:
Sean's not a startup guy. He is an expert in buying, building, and scaling businesses.
With his teams, he developed growth strategies and execution plans that led to the creation of over $100 million in new revenue for 4 companies over 8 years.
These companies included both large and small businesses, so Sean is uniquely positioned to understand the challenges Founders face at different stages of their scaling journey.
Sean now shares his methodology and frameworks for preparing for investment, installing management and full exits for 1m-30m businesses through his advisory services, podcasts and education programs.
The Founders Sean mentors personally grow revenue by an average of $3.1m and EBITDA by $488k over the first two years.
He brings over 15 years of experience in growing businesses to the table. He’s integrated 7 brands into larger structures, scrutinised over 200 acquisitions, and consulted with ASX-listed companies on their acquisition strategies.
Sean is also the host of the ScaleHQ Podcast where he shares his methods, interviews successful entrepreneurs, experts on scaling, and Founders striving to scale.
About Sean Steele
Sean has led several education businesses through various growth stages including 0-3m, 1-6m, 3-50m and 80m-120m. He's evaluated over 200 M&A deals and integrated or started 7 brands within larger structures since 2012. Sean's experience in building the foundations of organisations to enable scale uniquely positions him to host the ScaleUps podcast.
