The Flamingo Property Investing Podcast with Jack Henderson

Standing out from the crowd and investing like the wealthiest 1%

Diversifying Beyond Property: How the Wealthy Invest

Looking to GROW your wealth: ⁠⁠⁠⁠⁠https://henderson.com.au/⁠⁠⁠⁠⁠Keen to START/SCALE your portfolio: ⁠⁠⁠⁠⁠https://calendly.com/jackhendersonproperty/15min⁠⁠⁠⁠⁠Listen to EXPERT advice: ⁠⁠⁠⁠⁠https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65Hm⁠⁠⁠⁠⁠Hi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it. Real growth happens when you don’t let fear stop you.

09-17
52:15

Inheritance Planning: Protect What You Leave, Maximise What You Get

Looking to GROW your wealth: ⁠⁠⁠⁠https://henderson.com.au/⁠⁠⁠⁠Keen to START/SCALE your portfolio: ⁠⁠⁠⁠https://calendly.com/jackhendersonproperty/15min⁠⁠⁠⁠Listen to EXPERT advice: ⁠⁠⁠⁠https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65Hm⁠⁠⁠⁠Hi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.

09-10
42:30

The Strategy That Unlocked Caelah's Borrowing Capacity

Find out how to earn $300,000+ from a tech sales career from Caelah HERE: https://bit.ly/caestanLooking to GROW your wealth: ⁠⁠⁠https://henderson.com.au/⁠⁠⁠Keen to START/SCALE your portfolio: ⁠⁠⁠https://calendly.com/jackhendersonproperty/15min⁠⁠⁠Listen to EXPERT advice: ⁠⁠⁠https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65Hm⁠⁠⁠Hi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.

09-03
01:07:06

Retired at 51: The Power of Property Investing

Looking to GROW your wealth: ⁠⁠https://henderson.com.au/⁠⁠Keen to START/SCALE your portfolio: ⁠⁠https://calendly.com/jackhendersonproperty/15min⁠⁠Listen to EXPERT advice: ⁠⁠https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65Hm⁠⁠Hi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

08-28
56:14

Scaling Through Setbacks: The Conviction That Built Henderson Advocacy

This week Jack joined Marty Fox on the With The Fox podcast to share the story behind building Henderson Advocacy from a one-man operation into a national business buying 40+ homes a month. From setbacks and personal challenges to brand clarity, resilience, and scaling with conviction, this episode dives into the lessons that shaped the journey.Looking to GROW your wealth: https://henderson.com.au/Keen to START/SCALE your portfolio: https://calendly.com/jackhendersonproperty/15minListen to EXPERT advice: https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65HmHi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

08-20
47:17

Real Estate or Business? The 2025 Wealth-Building Showdown

This week Jack was featured on the Founders Table podcast with host Frank Greef to debate with Charlie Gearside, co-founder of Eucalyptus on what the best way to generate wealth is in Australia in 2025 - through real estate or business?Looking to GROW your wealth: https://henderson.com.au/Keen to START/SCALE your portfolio: https://calendly.com/jackhendersonproperty/15minListen to EXPERT advice: https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65HmHi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

08-13
55:06

How I Built My $40M+ Property Portfolio And Scaled My Business From Zero

This week Jack was featured as a guest on A Lot To Talk About with Bradley J Dryburgh to talk about the mindset and motivation that continues to drive him to grow his property portfolio and scale his businesses.Looking to GROW your wealth: https://henderson.com.au/Keen to START/SCALE your portfolio: https://calendly.com/jackhendersonproperty/15minListen to EXPERT advice: https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65HmHi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

08-06
01:33:31

My 2025 Playbook for Entrepreneurs: Income, Investing & Influence

This week Jack was invited to speak with business owners at Boa about his property journey and how he has spent the past few years scaling the business.Looking to GROW your wealth: https://henderson.com.au/Keen to START/SCALE your portfolio: https://calendly.com/jackhendersonproperty/15minListen to EXPERT advice: https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65HmHi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

07-30
47:46

The ATO Wants Its Money Back: What You Need to Know in the New Financial Year

Accountant and Financial Planner Jeremy Iannuzzelli joins us again this week to explain why the ATO is gearing up to be more aggressive this new financial year, and how it all affects you.Looking to GROW your wealth: https://henderson.com.au/Keen to START/SCALE your portfolio: https://calendly.com/jackhendersonproperty/15minListen to EXPERT advice: https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65HmHi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

07-23
36:01

Build a Business, Buy Property, Create Freedom

This week Jack was invited to share his insights at the Club of United Businesses to discuss his property journey and explain how you can use property and businesses in tandem to take both to new heights.Looking to GROW your wealth:⁠⁠⁠https://henderson.com.au/⁠⁠⁠Keen to START/SCALE your portfolio:⁠⁠⁠https://calendly.com/jackhendersonproperty/15min⁠⁠⁠Listen to EXPERT advice:⁠⁠⁠https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65Hm⁠⁠⁠Hi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.

07-16
47:01

The Agent Who Sold Me a $5.5M Farm: Nathan on Regional NSW's Rise

This week we're joined by Nathan Vincin from Cutcliffe, the agent who sold Jack his rapidly growing wedding venue Settler's Rest, as they discuss the future regional NSW and the truths around property development.Looking to GROW your wealth: https://henderson.com.au/Keen to START/SCALE your portfolio: https://calendly.com/jackhendersonproperty/15minListen to EXPERT advice: https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65HmHi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

07-09
48:59

The Psychology of Property: Money, Mindset & Making It Work

This week Jack was featured on Agency Podcast to chat with host Dain Walker about the property market and the mindset it takes to be successful in all areas of your life.Looking to GROW your wealth:⁠⁠⁠https://henderson.com.au/⁠⁠⁠Keen to START/SCALE your portfolio:⁠⁠⁠https://calendly.com/jackhendersonproperty/15min⁠⁠⁠Listen to EXPERT advice:⁠⁠⁠https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65Hm⁠⁠⁠Hi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.

07-03
01:21:58

He Held His Property For 8 Years and LOST MONEY

This week we're joined by our Head Buyer's Agent in Newcastle, Sam Black, to share a tonne of insight around renovations, the Newcastle market and the mistakes he made in property before he got educated.Looking to GROW your wealth: https://henderson.com.au/Keen to START/SCALE your portfolio: https://calendly.com/jackhendersonproperty/15minListen to EXPERT advice: https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65HmHi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

06-27
54:44

The Game Is Rigged—Jay Wright on Why Property Always Wins

This week we're joined by Jay Wright from Ecommerce Equation to talk about how he's used his own portfolio and businesses to generate large amounts of wealth and how property stacks up against investing in shares.Looking to GROW your wealth: https://henderson.com.au/Keen to START/SCALE your portfolio: https://calendly.com/jackhendersonproperty/15minListen to EXPERT advice: https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65HmHi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

06-19
53:17

The Cost of the Dream: Traci Chen on Migrant Sacrifice and Success

This week on Flamingo Property Investing we're joined by migration lawyer Traci Chen to talk about what it takes to build a business and the challenges that immigrants face when trying to buy property in Australia and make a life for themselves and their families.Looking to GROW your wealth: https://henderson.com.au/Keen to START/SCALE your portfolio: https://calendly.com/jackhendersonproperty/15minListen to EXPERT advice: https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65HmHi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

06-12
47:57

Sales Weapon Matt Ryder on Targeting Your Niche and Taking the Shot

This week on Flamingo Property Investing, expert sales coach Matt Ryder explains the relationship between property and sales and how you can utilise both to become extremely successful.Looking to GROW your wealth: ⁠⁠⁠⁠⁠https://henderson.com.au/⁠⁠⁠⁠⁠Keen to START/SCALE your portfolio: ⁠⁠⁠⁠⁠https://calendly.com/jackhendersonproperty/15min⁠⁠⁠⁠⁠Listen to EXPERT advice: ⁠⁠⁠⁠⁠https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65Hm⁠⁠⁠⁠⁠Hi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

06-05
01:03:51

Structuring a Property Portfolio That Actually Supports Retirement - with Matt Spears

This week on Flamingo Property Investing, Matt Spears - Finance Broker and Managing Director of Evoke Capital joins us to discuss what a foundational property portfolio looks like and how to structure it correctly to take you to retirement.Looking to GROW your wealth: ⁠⁠⁠⁠https://henderson.com.au/⁠⁠⁠⁠Keen to START/SCALE your portfolio: ⁠⁠⁠⁠https://calendly.com/jackhendersonproperty/15min⁠⁠⁠⁠Listen to EXPERT advice: ⁠⁠⁠⁠https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65Hm⁠⁠⁠⁠Hi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

05-30
39:31

Jake's Strategy to Retire 20 Years Early

This week on Flamingo Property Investing we invite Jake, a property strategist from Henderson Advocacy onto the podcast to talk about his property investing journey and his plan to retire by 48 years old.Looking to GROW your wealth: ⁠⁠⁠https://henderson.com.au/⁠⁠⁠Keen to START/SCALE your portfolio: ⁠⁠⁠https://calendly.com/jackhendersonproperty/15min⁠⁠⁠Listen to EXPERT advice: ⁠⁠⁠https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65Hm⁠⁠⁠Hi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

05-24
50:15

Paving Your Path to Retirement with James Wrigley - FPI Podcast

This week on Flamingo Property Investing, Jack travels to Melbourne to speak to financial planner James Wrigley about how to strategise your financial future.Looking to GROW your wealth: ⁠⁠https://henderson.com.au/⁠⁠Keen to START/SCALE your portfolio: ⁠⁠https://calendly.com/jackhendersonproperty/15min⁠⁠Listen to EXPERT advice: ⁠⁠https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65Hm⁠⁠Hi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

05-16
47:02

Ex-Banker Turned Broker Reveals the Truth About Real Estate Finance (ft. Jordan Beh)

This week on Flamingo Property Investing, we have Jordan Beh back in the studio to break down the differences between working with bankers and brokers so that you can begin to work out the strategy that's right for you.Looking to GROW your wealth: ⁠https://henderson.com.au/⁠Keen to START/SCALE your portfolio: ⁠https://calendly.com/jackhendersonproperty/15min⁠Listen to EXPERT advice: ⁠https://open.spotify.com/show/7CWEEu0rCWgtxeSOak65Hm⁠Hi, I'm Jack Henderson, Founder and Director of Henderson Advocacy, Endeavour Build & Henderson Develop - one of Australia's fastest growing full-service property advisory & buyers' agency, luxury development and development funds. In 2015, I purchased my first property at 18 years old and over the past 9 years have grown my portfolio to over $35 million in assets.My journey has been all about pushing past fear and taking big risks.At 15, I left school without a clear plan because I knew the traditional path wasn’t for me.That decision led me to work in construction and eventually into real estate, where I found a chance to build something real.By 18, I bought my first property. Was it risky? Absolutely, but it was worth it.Real growth happens when you don’t let fear stop you.@jackchenderson - produced by Know Media.

05-06
44:20

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