Bothsides Podcast

What if the No.1 reason you’ve never achieved your goals has nothing to do with talent, luck, or resources… but the way your mind retreats when things get hard?Entrepreneur, investor, and founder Jack Delosa has spent two decades building, scaling, and rescuing companies worth hundreds of millions. He’s been $25M up, $5M down, and rebuilt again. Now, he’s revealing the real reasons most people never succeed - and the simple frameworks you can use to finally break through excuses, fear, and overwhelm.With brutal honesty and hard-won experience, Jack exposes the uncomfortable truths about why people quit, how to stop self-sabotage, and what it actually takes to achieve big goals in today’s world.Jack is the founder of The Entourage, Australia’s largest training institution for entrepreneurs, and an active investor with over $100M in portfolio value. He’s been featured in BRW Young Rich List multiple times and is the author of two best-selling business books.In this conversation, Jack reveals:◼️ The No.1 reason people never achieve their goals (and how to beat it).◼️ Why your brain’s natural instinct is to retreat into excuses when things get tough.◼️ The 2-hour rule that can transform your business and life in weeks.◼️ How to identify and fix the real constraint that’s holding back your success.◼️ Why most entrepreneurs are trapped in busywork instead of growth work.◼️ The hidden danger of operational debt and how to reverse it fast.◼️ Why leaning into AI now can be your biggest advantage in the next 5–7 years.Enjoy!

Adrian Oddi has sold hundreds of millions in real estate over 23 years, yet made a shocking decision that goes against everything he teaches clients. After surviving cancer and divorce simultaneously, this Brisbane Whitney director completely restructured his priorities - and the results might surprise you.From someone who once worked 6 days a week for 26 years straight, Adrian now starts work at 11am, has his team doing 3x more business than him, and admits he has a "50 million by 50" goal he doesn't even understand why he wants.What you'll discover:Why a millionaire agent chooses renting over $30M+ Bondi propertiesThe "buyer-first" strategy that revolutionized his team's successHow his assistant Jasmine now has 3x more listings than him (and why he's thrilled)His brutal honesty about the cancer scare he never shared publiclyThe morning routine that lets him work fewer hours while earning more Why he believes most real estate agents are playing the wrong game entirely

Joshua Charles went from earning $0 to more than the Prime Minister by age 24.Now at 51, he's facilitated $7.2 billion in commercial real estate transactions and reveals exactly how the game is played.What you'll discover:​The exact moment foreign investors stopped touching Victorian property (and the $100M opportunity it created)​How One Commercial beats billion-dollar firms using Instagram and TikTok​The $70M Alexandria property that went from "not for sale" to SOLD with one call​Why 50% of massive commercial deals happen completely off-market​The Marrickville deal that jumped from $200k to $1M commission (and why Joshua got $0)​How AI is replacing entire analyst teams and doing a week's work in 5 minutes​The specific Sydney suburbs about to explode…​Why he hired someone who memorized his coffee order and how attention to detail wins $100M deals.

Jacques Greeff just sold his second tech company for $180 million. But he's not celebrating - he's warning other business owners about what's coming next.After taking a year off to reflect on his massive exit, Jacques made a shocking decision: instead of retiring rich, he's diving back into the AI wars at 4:30am every morning. Why? Because he sees something most entrepreneurs are missing.In this raw conversation, Jacques shares the brutal truth about AI adoption, the hiring mistakes that kill startups, and why building a billion-dollar company is actually easier now than ever before (if you know the secret).What you'll discover:​The real reason 90% of businesses will fail in the AI transition​How one missed LinkedIn DM almost cost them $50 million in their exit​Why Jacques thinks traditional morning routines are complete BS for founders​The communication breakdown that's costing entrepreneurs millions ​His controversial take on why failure stats lie to aspiring founders​The family revelation that changed his entire approach to business​Why technical skills matter less than this one personality trait in hiring- How Frank's "cooked" inbox led to their next $1B opportunity ​The attention economy strategy they're using to build in public- Why he's documenting every failure on YouTube (even the embarrassing ones)

At 6 months old, Hung Chuy should have died at the bottom of the ocean. Thai military shot holes in his family's refugee boat and left them stranded at sea for a week with no food or water. Today, he owns over $20million in property and runs one of Australia's fastest-growing brokerages.This isn't your typical "rags to riches" story - it's a survival story that turned into a wealth empire. Hung went from nearly dying as a baby to making $400,000 at 19, then willingly took a $49,000 bank job to master the system from the inside.What you'll discover:​How his family survived being left to die at sea by military forces​The "scarcity mindset" that helped him negotiate everything (including his way to millions)​Why he walked away from $400K income to become a $49K bank teller​His "Da Vinci Code" for building wealth that banks don't want you to know​How he bought 10 properties in just 12 months (and why he's not stopping)​The real reason 150+ real estate agents trust him with their money​His controversial take on why financial planners are mostly uselessFrom sleeping in refugee camps to building a property empire - Hong's story proves that your worst circumstances can become your greatest strengths.But warning: his approach to wealth building will challenge everything you think you know about property investment.Ready to learn the system that took a refugee to $20M+?Watch until the end for his exact blueprint.

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

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

In this enlightening conversation, property investor and entrepreneur Sammy Gordon shares his remarkable journey from humble beginnings on a rabbit farm to amassing a portfolio of 134 properties worth over $60M. He dives into his first property purchase at 19 and discusses the pivotal lessons on delayed gratification and strategic mentorship. Sammy emphasizes the importance of remaining grounded, revealing how living below his means fueled his growth. Listeners will gain invaluable insights into navigating real estate investment and cultivating resilience in the face of challenges.

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

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.