Inside the Broker’s Mind: Why Buyers Walk (And What Really Sells a Business)
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S1 E12

Inside the Broker’s Mind: Why Buyers Walk (And What Really Sells a Business)

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Most business owners think their business will sell because of the numbers — the profit, the growth, the potential. But step into a business broker’s world, and you'll find that's not what kills deals. It’s fear.
In this episode of Built to Sell | Built to Buy, host Sam Penny is joined by Australia’s #1 business broker Sally Stuart, who sold 35+ businesses in just the past two years. Together, they unpack exactly why businesses don't sell — even when the financials look strong — and what actually makes a business irresistible to buyers.
Sally reveals:
  • 🔥 The surprising reason most buyers walk away
  • 💣 Why your lawyer might be the biggest dealbreaker
  • 💡 What makes a business “sexy” and sparks bidding wars
  • 🧾 The accounting mistakes that scare buyers off
  • 🏢 Why short leases quietly destroy business value
  • 🛑 How ego, overpricing, and bad timing sabotage the sale
  • ✅ The 3–5 things every owner should do 12–24 months before listing
  • 💬 Why a broker isn’t just a sales agent — they’re a dream facilitator
If you’re a business owner thinking of selling, or an investor who wants to understand what really moves the needle in a deal, this episode is your blueprint. Straight from the broker’s mouth.
🔗 Links & Resources:
  • 📞 Book a call with Sam Penny: https://sampenny.com/chat
  • 📚 Learn more about Sally Stuart: https://linkbusiness.com.au/business-broker/sally-stuart/
  • 🔍 Free Business Sale Readiness Report: https://sampenny.com/readiness
⏱️ Timestamps:
  • 00:00 – Intro: What really kills deals?
  • 02:45 – Sally’s journey into business broking
  • 04:00 – What business brokers actually do
  • 08:30 – The lawyer trap that destroys deals
  • 11:00 – What makes a business spark a bidding war
  • 15:20 – The self-sabotage sellers don’t see coming
  • 20:30 – How leases quietly crush deals
  • 24:00 – Why owner-dependence kills valuations
  • 28:55 – What buyers really want (and where they’re from)
  • 33:15 – The biggest mistake sellers make around timing
  • 36:15 – 5 things to do 12–24 months before listing
  • 42:00 – Culture, values, and why your website matters
  • 44:00 – Sally’s lightning round: Dealbreakers, red flags & wisdom

Episode Video

Creators and Guests

Sam Penny
Host
Sam Penny
Sam Penny is an entrepreneur, business coach, and adventurer who’s built and sold multi-million-dollar companies — and taken on challenges most people wouldn’t dream of, from swimming the English Channel in winter to tackling an Ice Mile. Known as The Impossible Guy, Sam works with business owners to prepare for their biggest payday and with investors to buy smarter, more profitable businesses. On Built to Sell | Built to Buy, he brings a unique mix of hard-earned business wisdom, real deal experience, and a knack for asking the questions others won’t.
Sally Stuart
Guest
Sally Stuart
Sally Stuart is a leading business broker specialising in the sale of health, medical, and allied health businesses. With a track record of guiding owners through complex transactions, she’s known for her ability to position businesses for maximum buyer interest and negotiate deals that work for all parties. Sally brings deep industry knowledge, a strong network of buyers, and a straight-talking approach to every transaction. On Built to Sell | Built to Buy, she shares the strategies, trends, and behind-the-scenes realities that determine whether a sale is smooth — or stalls.