The Business Game
The Business Game
The Business Game is not another highlight reel of overnight success. It is a structured, honest breakdown of what it really takes to build, scale, and sustain a business at every level.
We built The Business Game around a simple truth: business changes as revenue changes. The problems at $500K are not the problems at $5M. The mindset at $5M is not the mindset at $50M. That is why every conversation is grounded in our 10-Level framework, from Level 1 Startup and Survival through to Level 10 Legacy and Exit.
If you are:
• Trying to get your first consistent revenue
• Building your first real team
• Breaking through the messy middle
• Scaling toward eight or nine figures
• Or preparing for exit
There is an episode that meets you where you are.
Hosted by Steve Plummer and Kalena Stano, who speak to founders operating at every stage of the game. No gatekeeping. No hype. No recycled advice. Just real numbers, real mistakes, real strategy, and real decisions that moved the needle.
Each week, we publish two episodes every Monday and Thursday at 6pm AEST, featuring global founders, operators, and investors who break down what actually works at their level and what does not.
The Business Game exists to give you clarity. To help you identify your current level. To show you the moves required to reach the next one.
Because scaling is not random. It is a game. And every level has different rules.
Find your level. Play it properly. Then level up.
Watch video episodes on YouTube and explore more at thebusinessgamegroup.com
The Business Game
Wall Street Doesn’t Care If You Lose Money
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In this episode of The Business Game, hosts Steve Plummer and Lisa DeAngelis sit down with Steven Woods, founder and CEO of Stirlingshire, to unpack how the financial system really works and why many everyday investors feel left behind.
Steven shares his journey from Kansas City to Wall Street, walking away from a lucrative advisory career with no safety net, and the hard lessons he learned along the way, including what it’s like to lose seven figures in a single day. He explains why much of modern finance is unnecessarily complex, how incentives inside large firms shape investor outcomes, and why transparency and alignment matter more than ever.
The conversation also explores Steven’s simple “grocery store” analogy for understanding the stock market, why people often underestimate how much money they’ll need in the future, and how technology and AI are changing the role of financial advisors - making them more effective rather than obsolete.
Whether you’re a founder, advisor, or someone trying to build more confidence around money and investing, this episode offers a grounded, honest perspective from inside the industry.
You’ll hear about:
- Steven Wood’s path from Wall Street intern to founder & CEO
- Why he built Stirlingshire to better align advisors and clients
- What losing seven figures in a day teaches you about risk
- Why finance often stays opaque and who benefits from that
- The biggest money assumption most people get wrong
- How AI is improving advisor decision-making and efficiency
- The mindset shift beginners need to start investing sooner
- Lessons elite institutions don’t teach about running real businesses
Connect with Steven Woods - Stirlingshire:
LinkedIn: https://www.linkedin.com/in/stirlingshireinvestments/
Website: https://www.stirlingshire.com/
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Thanks to Smoothx for sponsoring this episode. Smoothx, your global power connector, Visit https://www.smoothx.com/ to get started.
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This episode is for educational purposes only and does not constitute financial advice.
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Thank you for listening to The Business Game, where real founders break down the real levels of business.
Whether you're building at Level 1 ($0–$1M) or scaling through Level 6 and beyond, this show is designed to help you understand exactly where you are, and what it takes to level up.
If you enjoyed this episode, please subscribe, follow and leave a review. It helps more founders find the roadmap.
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Want to identify your level or learn more about The Business Game framework?
Visit www.thebusinessgamegroup.com
It's time to Level Up!
We’ll see you at the next level.
