At 25, Tyler Dunagin was managing a quarter billion dollars in real estate assets for someone else.

He had the title, the income, and the career path everyone said to want.

Then he drained his 401k, bought a box truck, and started flipping apartments.

His parents asked: "Are you sure?" He said: "It's too late. Already did it."

Today Tyler runs Turn Serve - an Inc 5,000 listed company, ranked 2nd fastest-growing in its space - plus a platform of brands and a patented bathroom product he invented himself.

And he did it without connections, without a business degree, and without a plan that looked good on paper.

In this conversation, Tyler gets into:

→ Why your "why" is allowed to start selfish, and why that's actually the right place to start

→ The counterintuitive habit his coach forced on him that unlocked his best thinking

→ Why far less qualified people are doing far more than you - not because they're smarter, but because they simply decided to start

→ How curiosity beats credentials every single time→ What it really means to leave a legacy (hint: it's not the house or the trust fund)

This one will hit.

Turnserv Property Management: https://www.turnserv.com/about/leadership

What if everything you thought about financial planning was wrong?

In this episode Mike Milligan - founder of One Oak Financial, Amazon bestselling author, and one of the most compelling voices in personal finance today - had a conversation with me that goes far deeper than money.

Mike shares how watching his grandmother sell collard green sandwiches as a child sparked a lifelong love for business and wealth-building. He opens up about the devastating loss of his brother Jonathan at 41 - and how that moment redefined his entire mission. And he pulls back the curtain on the financial industry, revealing exactly how to tell if your advisor is truly working for you or just chasing a commission.

This episode covers:

-Why financial education is the most powerful tool you have

-How to vet a financial advisor (and the questions most people never think to ask)

-The "mirroring" sales technique used against you, and how to spot it

-Why a real financial plan fits on one piece of paper

-How to start building a one of a kind life - at any age

Whether you are just starting out or approaching retirement, this conversation will change the way you think about money, time, and legacy.

Connect with Mike Milligan: Website

Mike Miligan Linkedin

Subscribe to Journey to Legacy for weekly conversations with entrepreneurs and leaders who are building lives and businesses worth remembering

What if your next trip didn’t just change your mood… but your entire life?

In this episode of Journey to Legacy, Wayne Veldsman sits down with Christopher Hill, founder of Impact Destinations and Hands Up Holidays, to unpack how one trip to South Africa completely shifted his path - from investment banking into purpose-driven entrepreneurship.

They dive into:

-Why following your passion makes life feel lighter

-How to take a calculated risk into entrepreneurship

-The power of meaningful travel

-Real world impact of what it actually means to build a legacy

If you’ve ever felt stuck in a path that doesn’t fully align - this conversation is for you.

Learn more about Chris:https://impactdestinations.com

/https://handsupholidays.com/

This episode is sponsored by Taelor. Most guys spend way too much time figuring out what to wear- and still end up in the same three outfits. Taelor fixes that. A personal stylist picks clothes in your size and style, ships them to you every 2 weeks- You wear them and return them. No shopping, no laundry, and no more spending on new clothes. Use code JTL at Taelor.style for 25% off your first month: https://taelor.style/

What if “playing it safe” is actually the biggest risk you can take?

In this episode, Kam Dasani breaks down why most people are playing the money game backwards, and how traditional advice around saving, investing, and retirement might be holding you back.

We dive into:

• The truth about risk

• Why most people stay stuck financially

• What separates successful traders from everyone else

If you’ve ever questioned the traditional path… this conversation is for you.

🔗 Connect with Kam

Instagram: https://www.instagram.com/profitwithkam/

YouTube:https://www.youtube.com/live/Q5XzG809WhI

LinkedIn: https://www.linkedin.com/in/kam-dasani-937005101/

🔗 Journey to Legacyhttps://journeytolegacy.org

This episode is sponsored by Taelor. Most guys spend way too much time figuring out what to wear- and still end up in the same three outfits. Taelor fixes that. A personal stylist picks clothes in your size and style, ships them to you every 2 weeks- You wear them and return them.

No shopping, no laundry, and no more spending on new clothes.

Use code JTL at Taelor.style for 25% off your first month: https://taelor.style/

What if success isn’t about grinding harder… but about becoming psychologically indestructible?

In this episode of Journey to Legacy, Wayne Veldsman sits down with entrepreneur, investor, and author John Fairclough, who went from bouncing between homes at 11 years old to building companies that serve luxury brands across the United States, Canada, Guam, and Puerto Rico.

But this conversation goes far beyond business.

John shares powerful insights on resilience, identity, leadership, and why building external success without internal alignment can eventually break you.

We talk about adversity, personal development, emotional strength, and what it truly means to live a successful life.

One of the most powerful ideas from this episode:

“A successful life is a peaceful life.”

If you're an entrepreneur, leader, or someone trying to build a meaningful legacy, this conversation will challenge how you think about success.

Connect with John Fairclough

Website:
https://johnfairclough.com/

YouTube:
https://www.youtube.com/@TheJohnFairclough

LinkedIn:
https://www.linkedin.com/in/johnfairclough/

Try Taelor.Style and use code JTL for 25% off your first month.

Learn more here:
https://taelor.style/

Every morning, you’re handed something priceless.

Not money.

Not luck.

A diamond.

Rabbi Daniel Cohen explains a powerful spiritual idea from Jewish mysticism:

Every day God gives us an unpolished diamond.

By the end of the day, we give it back.The only question is…How much did we polish it?

In this conversation, Rabbi Cohen shares the mindset that can completely change the way you see your life, your purpose, and even your struggles.

We explore:

• Why thinking about death can actually make you live better

• The 20-second elevator moment that can change someone’s life

• Why helping someone else is the fastest way to escape depression and darkness

• The difference between being a river vs. a dam

• How tiny acts of kindness ripple through generations

• The powerful exercise: 5 words you want to be remembered by

Most people believe legacy is something that happens after they die.

Rabbi Cohen explains why legacy is created every single day.

And it might start with something as simple as a smile, a conversation, or a moment of kindness.

Learn more about Rabbi Daniel Cohen🌐 https://www.rabbidanielcohen.com/

Build Your Legacy

If you want deeper conversations about purpose, business, faith, and legacy:

👉 Visit https://journeytolegacy.org/programs

📺 Watch the Journey to Legacy Podcast https://youtu.be/LdGFt613P94

Most people don’t struggle because they don’t earn enough.

They struggle because they’re using a system designed to keep them dependent.

In this episode of Journey to Legacy, Wayne sits down with Brent Kesler, founder of The Money Multiplier, to unpack a wealth strategy the affluent have used quietly for over 200 years.

From living behind a vacuum cleaner store and showering at the YMCA… to eliminating $984,711 in debt in just 39 months and growing a $21M+ real estate portfolio, Brent explains the “one additional step” that changed everything.

In this conversation:

• Why most families are financially stuck (without realizing it)• The Infinite Banking Concept - and why people tune out too soon

• How to design a life where money works harder than you do• Why traditional financial advice isn’t serving most entrepreneurs

• How to recycle and recapture your dollars over and over

👉 Learn more about The Money Multiplier: https://themoneymultiplier.com/

👉 Ready to build your legacy? https://journeytolegacy.org/

Most people think they’re stuck.

But according to Robb Kelly, you’re not stuck - you’re repeating.

In this powerful episode, Robb breaks down how the brain wires itself for repetition - and why lasting recovery requires more than willpower.

It requires awareness, interruption, and intentional change.

We dive into:

• Why destructive patterns feel automatic

• The neuroscience behind addiction and repetition

• How identity shapes behavior

• What real recovery actually looks like

If you’ve ever felt trapped in cycles you can’t seem to break - this conversation is for you.

Learn more about the Robb Kelly Recovery Group:👉 https://robbkelly.com

#JourneyToLegacy #RobbKelly #Recovery #AddictionRecovery #Mindset #PersonalGrowth