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A Conversation with Stephen Keighery
Catching up on an inspiring episode with Stephen Keighery — Australian entrepreneur turned U.S. real estate investor — as he shares the unconventional path that took him from Bondi Beach to building a $315M ASX-listed company, and then starting over again in Louisiana. From founding High Pages Group and scaling it to 300 employees and 35,000+ paying customers, to walking away from corporate life and tackling distressed real estate in New Orleans, Stephen breaks down the mindset, risks, and reinvention required to build meaningful businesses across borders.
In this episode, you’ll learn:
• How a Robert Kiyosaki seminar completely changed Stephen’s trajectory and pushed him toward entrepreneurship.
• What it really takes to scale a marketplace business to an IPO — and why Stephen chose to step away at the peak.
• The cultural differences between entrepreneurship in Australia and the United States, including the “tall poppy syndrome.”
• How Stephen transitioned from tech and marketing into real estate by applying two-sided marketplace principles.
• Why New Orleans became home — and how he’s reducing blight and expanding housing through distressed property investing.
• The pressures of building a business under a U.S. E-2 investor visa and what entrepreneurs should know about the process.
• Stephen’s low-pressure, Aikido-style approach to sales and why listening beats arguing every time.
• Advice for young entrepreneurs willing to fail nine times to win once.
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By Michael PeresCatching up on an inspiring episode with Stephen Keighery — Australian entrepreneur turned U.S. real estate investor — as he shares the unconventional path that took him from Bondi Beach to building a $315M ASX-listed company, and then starting over again in Louisiana. From founding High Pages Group and scaling it to 300 employees and 35,000+ paying customers, to walking away from corporate life and tackling distressed real estate in New Orleans, Stephen breaks down the mindset, risks, and reinvention required to build meaningful businesses across borders.
In this episode, you’ll learn:
• How a Robert Kiyosaki seminar completely changed Stephen’s trajectory and pushed him toward entrepreneurship.
• What it really takes to scale a marketplace business to an IPO — and why Stephen chose to step away at the peak.
• The cultural differences between entrepreneurship in Australia and the United States, including the “tall poppy syndrome.”
• How Stephen transitioned from tech and marketing into real estate by applying two-sided marketplace principles.
• Why New Orleans became home — and how he’s reducing blight and expanding housing through distressed property investing.
• The pressures of building a business under a U.S. E-2 investor visa and what entrepreneurs should know about the process.
• Stephen’s low-pressure, Aikido-style approach to sales and why listening beats arguing every time.
• Advice for young entrepreneurs willing to fail nine times to win once.