Bothsides Podcast

• EP 127 | Simon Caulfield: Player–Coach Leadership & Legacy

  In this episode, Director of Place Kangaroo Point, Simon Caulfield unpacks how he’s built an office where top performers have their own identities—not “from Simon’s office”—and why the business must thrive without him. We get into pathways from 500k GCI to seven figures, case studies across high-volume vs high-value models, and Simon’s personal playbook: two champagne COI events a year, a “favorites” list he calls religiously, and being a present, trusted local over flashy ads. In this Simon shares lessons from moving upmarket (from $555k beginnings to KP’s top end), the difference between selling resi and selling the dream off-the-plan, and the player-coach balance of leading six team presentations a week while still listing and selling. He dives into Wolfpack Fridays, retaining top talent by giving them reasons to stay, using an AI recorder to capture meetings and train staff, and the three-corner support team (manager, coach, trainer). Above all: listen intently, play to your strengths, move the needle each year, and leave people in a better place than you found them.Topics covered: Building a business where agents thrive under their own brandsLeadership mindset: “Leave people in a better place”Pathways from 500k to $1M+ GCI and choosing the right modelCase studies: high-value vs high-volume strategiesSimon’s COI playbook: champagne events & “diamond” call listMoving upmarket: perception, results, and social proofResi vs off-the-plan: selling the dream before it existsPlayer–coach leadership and when to step back from listingWolfpack Fridays: training, collaboration, and shared challengesRetaining top talent with support, recognition, and carePractical AI for onboarding and process improvementLegacy: success measured by impact, not trophies

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• EP 126 | Jonny Bell: $85M by 29 – The Power of Offshoring

  In this episode, Jonny Bell shares how he scaled Wingman and HouseMark using offshoring, technology, and strategic leadership to boost efficiency, revenue, and relationships. By combining onshore leadership with offshore support, Johnny frees his team to focus on high-value activities while transforming property management property managers now handle 250–300 properties each, compared to the usual 100–120, generating significant revenue gains.Jonny emphasises giving value first in business, being authentic, and building long-term relationships. He shares lessons on leadership, team empowerment, and leveraging data to help agents and businesses grow. For Johnny, success isn’t just financial—it’s about family, friendships, personal growth, and creating a life aligned with your values.From networking in New York to investing in AI and expanding internationally, Jonny’s journey is full of strategic moves and unexpected opportunities. He also reveals a key paradigm shift: focusing on what he can remove out of his diary each week, rather than just doing more.Topics covered:Jonny Bell’s journey building and scaling a property management business using offshoring and technologyExpanding Wingman with onshore leadership and offshore support: engineers, business analysts, and property management teamsLeveraging offshoring to increase efficiency: tenancy communication, trust accounting, lease renewals, arrears, and maintenance coordinationProperty managers managing 250–300 properties each versus the industry average of 100–120Boosting revenue: case studies showing extra $100,000+ per property manager annuallyStrategies for B2B relationship building: giving value first, authenticity, and long-term collaborationLeadership philosophy: understanding team strengths, coaching, and maximising potentialPersonal growth: lessons on avoiding mistakes, health, relationships, and strategic decision-makingExpanding Wingman internationally, including the US market and leveraging AIOffshoring applications for sales agents: marketing, contracts, pre-listing kits, data management, and buyer trackingNetworking and opportunity creation: the power of casual meetings and the “butterfly effect”Career advice: taking action, overcoming fear, and the cost of regret versus failureBalancing business growth with personal life, family, and friendshipsThe win-win-win model: benefiting property managers, business owners, and clients alikeJonny shares a surprising lesson from his early career that still guides his decisions today

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• EP 125 | Sammy Gordon: 134 Properties by 35 – The 8-Figure Blueprint

  In this powerhouse episode of Both Sides Podcast, we sit down with property investor, entrepreneur, and educator Sammy Gordon — founder of Australian Property Scout and School of Property, and co-host of Scouting Australia and Top 1%.From humble beginnings on a rabbit farm to building a portfolio of 134 properties worth over $60M, Sam’s story is one of relentless discipline, sharp strategy, and a deep commitment to helping others create financial freedom.We cover everything from his first property purchase at 19, to scaling a multi-million-dollar portfolio, to leading a 60-person team with the goal of retiring 500 Australians by 2030. Along the way, Sam shares the lessons that shaped his journey — the importance of delayed gratification, choosing the right mentors, avoiding bad advice, and focusing on the big picture.Whether you’re an aspiring property investor, a business owner, or simply someone chasing a bigger life, this conversation will leave you with the tools, mindset, and inspiration to make it happen.Topics Covered: Growing up on a rabbit farm and developing an early work ethicBuying his first property at 19 with no formal plan — and the moment that changed everythingHow a property magazine in a dentist’s waiting room became a life-changing turning pointBuilding from one property to 134+ through strategic, cashflow-positive investingLiving below his means (including driving a $5,000 car for 9 years) to fuel rapid portfolio growthThe shift from personal wealth-building to building a team and helping clients retire earlyWhy you shouldn’t take advice from people who haven’t done what you want to doThe APS mission to retire 500 Australians by 2030 — and the systems making it possibleThe reality of running multiple businesses while maintaining a clear vision for the futureSam’s perspective on risk, discipline, and why “slow and steady” beats chasing quick wins

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• EP 124: Shane Smollen — The $70M Exit, Strategic Scale & Staying Calm Under Pressure

  In this compelling episode of The Both Sides Podcast, we sit down with renowned entrepreneur, real estate leader, and motorsport enthusiast Shane Smollen. From a humble, working-class upbringing in Ipswich, Brisbane, to building a real estate empire with an enterprise value of over $70 million, Shane's journey is a testament to the power of growth, resilience, and staying true to your instincts.Shane shares his non-traditional blueprint for success—one that doesn't rely on rigid goals but instead centers around alignment, strategic thinking, and building powerful habits. We dive into his early days with McGrath, selling 10 offices in 2015, and how his love for motorsport parallels his approach to business and life.Whether you're an aspiring agent, entrepreneur, or simply navigating your own professional grid, Shane’s insights on composure, growth mindset, and performance under pressure will leave you inspired and ready to move the needle in your own journey.Guest: Shane Smollen – Entrepreneur, Investor, Former McGrath Sales Director, Motorsport Champion and current director of Central Elements Developments Topics Covered:Introduction to Shane Smollen and his $70M real estate successGrowing up in a working-class family and finding property by fateWhy Shane doesn’t believe in traditional goal settingPrinciples behind Shane’s “helicopter view” of life and decision-makingEarly career: Director of Sales at McGrath and private office ownershipLeaving corporate structure to follow alignment and autonomyMaking smart decisions without fixed goalsSelling his business and finding joy in helping others growMotorsport as a metaphor for business resilience and performanceComparing amateur and elite performance—what sits in the gap?How to identify weaknesses and turn them into habitsTrusting your instincts and becoming unconsciously competentReal estate’s human side vs. performance metricsComposure under pressure: advice for staying calm in chaosThe importance of practicing in business and not just consuming informationFollow Shane Smollen: @smollenmotorsportFollow Both Sides Podcast: @bothsides_podcast

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• EP 123 | Emily Davidson: Director & Top 1% Agent by 30

  At just 30 years old, Emily Davidson is a Director at Sotheby’s International Realty Paddington–Woollahra. She works alongside McLay Longhurst — ranked the number 4 agent in the country — as part of an elite business unit. But Emily is a powerhouse in her own right: managing a team, leading high-end deals, and carving her name into Sydney’s prestige market.In this episode, we unpack the story behind her rise:From growing up in Brisbane and losing her father at a young age...To moving to Sydney solo and building a reputation in one of the most competitive markets in the country.Emily opens up about what it really takes to succeed in real estate — the mindset, the discipline, the sacrifices, and the power of showing up with consistency, class, and confidence.Whether you're a young agent, entrepreneur, or someone chasing excellence — this episode is packed with insights, lessons, and raw inspiration from someone operating at the top of their game.

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