
Advertise on podcast: Journey To Legacy
Rating
4.6from
This podcast has
161 episodes
Language
EnglishPublisher
Wayne VeldsmanExplicit
No
Date created
2018/01/05
Latest episode
2026/10/23
Average duration
49 min.
Release period
15 days
Description
The Journey to Legacy Podcast is a personal development, entrepreneurship, and leadership podcast for people who want more than just success — they want purpose. Hosted by Wayne Veldsman, each episode features real stories from entrepreneurs, nonprofit leaders, and executives, sharing lessons on mindset, business growth, communication, and building a life of impact. Listen to Journey to Legacy to learn how to grow, lead, scale your business or nonprofit, and create a legacy that matters. Learn more at journeytolegacypodcast.com
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Check latest episodes from Journey To Legacy podcast
Find Your Passion by Choosing Your Problems | Jeff Emalaba founder of InvestFusion | JTL 160
2026/10/23
Jeff Emalaba had already put more than $11,000 into a property deal when the inspector told him to run. That costly experience became the starting point for InvestFusion, a platform designed to help real estate investors uncover potential risks before committing their money. In this episode of Journey to Legacy, Wayne Veldsman sits down with Jeff, an entrepreneur and risk specialist who previously analyzed financial markets on CNBC Africa.
Jeff shares how he started his first business as a teenager, found guidance through mentors and turned a problem he’d experienced into a business of his own.
We explore:
• How to identify a problem worth building a business around
• Why passion matters when the work gets difficult
• How reading and mentorship shaped Jeff’s entrepreneurial journey
• Why changing direction can bring you closer to your goal
• What building a legacy means in someone else’s everyday life
Free offer for the Journey to Legacy audience
In this episode, Jeff offers our listeners seven days of free access to InvestFusion’s premium features, plus free access to his wealth coaching program and private community, including weekly live coaching calls.The program covers topics such as building credit, business setup, accessing funding and evaluating real estate deals.
Visit InvestFusion at: https://www.investfusion.co/services
Find more episodes and join the Journey to Legacy community:https://journeytolegacy.org/
#JourneyToLegacy #JeffEmalaba #Entrepreneurship #BusinessIdeas #PurposeDrivenBusiness
How to Find Your Purpose Before You Feel Ready | Jonathan Domsky, Kidorable co-founder and founder of Untangled Coaching | JTL 159
2026/10/09
Jonathan Domsky learned how to invoice after making his first sale. More than two decades later, a familiar walk beside Lake Michigan helped him recognise that he wanted to become a coach.
In this episode of Journey to Legacy, Wayne Veldsman talks with Jonathan about finding your purpose, recognising your strengths and starting before you feel fully ready.
Jonathan co-founded Kidorable at 24, building a children’s accessories brand whose products have been sold in over 5,000 stores across more than 20 countries. Today, through Untangled Coaching, he helps entrepreneurs build businesses and lives that feel more meaningful.
In this conversation:
Why Jonathan calls life a curriculum for discovering your purpose
How your core values, purpose and natural strengths can guide your work
What your favourite compliment can reveal about what you value in yourself
Why “profit fuels purpose” and how receiving support can help you keep giving
How the way you treat people today contributes to your legacy
Connect with Jonathan: Untangled Coaching
Explore more and join the newsletter: https://journeytolegacy.org/
#JourneyToLegacy #JonathanDomsky #FindingYourPurpose #Entrepreneurship #PersonalGrowth
He Reached the C-Suite and Lost Himself | Graham Skidmore on Burnout and Identity | JTL 158
2026/09/25
At the height of his success, Graham Skidmore was also at the height of his misery. Graham spent 20 years helping Quicken Loans, now Rocket Mortgage, grow from around 400 people to 20,000.
He reached the C-suite, led a smaller company as CEO and earned a high six-figure income. Then, sitting in Starbucks with his CEO, Graham admitted he no longer knew who he was. In this episode of Journey to Legacy, Wayne Veldsman and Graham explore what happens when your identity becomes wrapped up in your career and performance.
They discuss:
• Why achievement stopped feeling good
• The physical warning signs Graham ignored
• How leaving corporate life shook his identity
• The Vegas golf trip that changed his view of career setbacks
• What eight years of therapy and coaching taught him about authenticity
• Why people thrive when they understand their individual wiring
This conversation is for anyone who has reached a goal and quietly wondered why it didn’t feel the way they expected.
Connect with Graham:
Harmony Health Institute:https://harmonyhealthinstitute.com/
SathTech:https://sathtechnology.com/
Graham on LinkedIn:https://www.linkedin.com/in/graham-skidmore
Follow Journey to Legacy:
Spotify: https://open.spotify.com/show/5ObOrJ1eszDpdDfMj8618I
YouTube:
https://youtu.be/6VHj5BArQJQ
If this episode made you think differently about success, share it with someone who needs the reminder that they are more than their title.
The Day I Fired My Wife| Rob Ferguson on Family First vs Business First | JTL 157
2026/09/10
Rob Ferguson spent thirty years climbing to CEO of a $400 million company, then walked away to turn around a hundred-year-old family business with seventeen cousins on the cap table, selling it for more than $100 million.
At fifty, standing on what looked like the top of the ladder, he realized there was no top, only more ladder.
That question sent him into sixteen years of studying why family businesses, which create 78% of new jobs in America, so often fail, not for lack of capital or talent but because nobody in the family is willing to have the hard conversation about what comes first, the family or the business.
In this conversation with Wayne, Rob unpacks the difference between a family first business and a business first family,
why neither is wrong but confusing the two creates years of friction,
and the governance rules he wishes he'd set before firing his own wife from a job she'd only started that morning.
He also gets into how purpose changes across a lifetime: his purpose at eighteen was beating his mentor to a Cadillac and a swimming pool, his purpose at fifty is helping family businesses last long enough to matter.
To learn more about Rob and the work he's doing at Ferguson Alliance, visit ferguson-alliance.com or connect with him on LinkedIn, search Rob Ferguson Alliance.
Want to be a guest on Journey to Legacy? Book your here.
For more episodes and resources, head to our Spotify channel or YouTube channel.
How to Actually Get Out of Your Comfort Zone | Neil Thubron, Arctic Ultra Winner | JTL 156
2026/08/27
Everyone tells you to get out of your comfort zone. Almost nobody tells you what to physically do on a Tuesday morning.
Neil Thubron spent thirty years at IBM, from typewriter engineer to senior executive, before leaving to build his own coaching practice. He also became the first Briton to win the 300 mile Yukon Arctic Ultra, a self-supported race across frozen Canadian wilderness where competitors risk frostbite and amputation.
He entered it roughly ten weeks before the start, then began training. In this conversation Neil breaks down the method behind that.
How to find the actual border of your comfort zone, why you will never feel ready in advance, and how putting a date on something forces the preparation that makes it possible. We also get into what he does when everything goes wrong at once, and why legacy is not a retirement project but something you are already building in the conversations you are having this week.
What we cover:
-The three sentences that tell you where your comfort zone ends
-Why "I'm not that type of person" is a decision, not a fact
-Entering first and training second, and why the deadline does the work
-Fear as preparation rather than obstacle
-Controlling the controllables when everything breaks at once
-Why the people who leave a legacy behind were never trying to
Connect with Neil:Website and free book: https://neilthubron.com/
Listen and Watch:
YouTube: https://youtu.be/orWwdNPBxok
Spotify: https://open.spotify.com/episode/1MLG6smhbhJ9YiuYSJyJAw
Want to be a guest:
Head to https://journeytolegacypodcast.com/ and hit the green Get Interviewed button.
Why You're Avoiding Your Own Business Numbers | Rebecca Irey, 35 years in finance | JTL 155
2026/08/06
Everybody works hard, but not everybody gets ahead. Rebecca Irey, founder of Blue Skye Financial, has spent 35 years in the industry watching the difference come down to strategy, not effort.
In this episode, you'll learn:
-Why avoiding your own business numbers is costing you more than you think (the "fat girl, get on the scale" moment)
-The three life events that leave women solely responsible for their finances, and how to prepare before they happen
-Why entrepreneurs need to treat their own savings as a cost of doing business, not an optional extra
-The three rules of the money game most people were never taught: how your debt is structured, how your income is taxed and why timing risk is real
-What legacy actually means when the money runs out, the stories, the values and the memories you build now
-If you've been grinding without a plan, or you've handed off the money decisions to someone else and hoped it'll work out, this one's for you.
Learn more about Rebecca: https://blueskyefinancial.com/
Watch episodes in YouTube: https://youtu.be/F-_wSSDs73U
Want to be a guest? Hit "Get Interviewed" at https://journeytolegacypodcast.com
Financial Planning Ignores 25% of Adults | Scott Barnes, CFP, Childfree Wealth | JTL 154
2026/07/23
Scott Barnes spent 25 years inside traditional financial planning before he realized the entire model was built on one assumption: that you will have children, and that the point of building wealth is to hand it over.
Roughly 25% of US adults are childfree. There is no chapter in the financial planning curriculum for them. Not a module, not a paragraph.
Scott is a advisor at Childfree Insights, working exclusively with childfree clients across all 50 states. He joins Wayne to unpack what actually changes when nobody is waiting at the end of the handover, and why it is a mechanical difference rather than a sensitivity one.
In this episode:
-Childfree vs childless, and why the planning conversation is different
-The missing curriculum: why advisor training has nothing on clients without children
-Why 80% of Childfree Wealth clients had never worked with an advisor before
-Die with zero, and giving while you are alive instead of leaving it behind
-The assets under management problem nobody talks about-Retiring before 60, the taxable brokerage bridge, Rule of 55 and 72(t)
-Why power of attorney matters more than a will if you are childfree
-The mistake of naming your own parents on your documents-Solo agers, long term care and the professional fiduciary
-Pets, pet trusts and care documents-The gardener and the rose for childfree couples
-Legacy as something you build today, not after you are gone
If this made you rethink what legacy means, share it with one person who needs to hear it.
Learn more about Scott's work at Childfree Insights: https://childfreetrust.com/
More from Journey to Legacy: https://journeytolegacy.org/
Watch on YouTube: https://youtu.be/EUCigoc0FP4Subscribe for more conversations on building a legacy you actually get to see.
AI Voice Cloning Is Stealing Thousands - Here's How to Stop It | Robert Siciliano Cybersecurity expert | JTL 153
2026/06/25
A scammer calls. The number is your daughter's. The voice screaming for help is your daughter's.
Except it isn't - it's AI voice cloning, and it's good enough to make a parent wire thousands of dollars to a stranger.
In this episode, Wayne sits down with Robert Siciliano, CEO of Protect Now LLC, a cybersecurity expert and private investigator with 30+ years teaching people how to recognize and outsmart fraud.
Robert breaks down why our instinct to trust is the exact vulnerability criminals exploit, and gives you a simple framework to protect your family, your money and your legacy.
What you'll learn:
The "human blind spot" that makes almost everyone a targetWhy manufactured urgency shows up in 95% of fraud - and how to spot it instantlyHow AI deepfakes and voice cloning have erased the old scam red flagsThe Strategic Human Firewall mindset that turns you from a target into a detectorThe AAA Protocol (Analyze, Authenticate, Act) - your break-the-fake playbookOut-of-band verification: the 10-second habit that stops nearly every scamThe story Robert tells about the cloned-voice kidnapping scam will change how you answer your phone.
Learn more about Robert and his work at protectnowllc.com.
Visit https://journeytolegacy.org/ to learn more of this entrepreneur community.
He Sold One T-Shirt. Built an Empire. | Rick Lowe, Founder of Brands In Limited | JTL 152
2026/05/26
Rick Lowe showed up to Portobello Market in 2003 with a suitcase full of Space Invaders T-shirts and spent nine hours in the cold London rain trying to sell them.
He sold one.
Most people would have gone home. Rick looked at that single sale and thought: "Good. Now I just need to find more people."
That reframe is the foundation of everything he's built since.
Today, Rick's company ships hundreds of thousands of units a year under licensing deals with Disney, Warner Brothers, Netflix, The Rolling Stones, Mötley Crüe, and some of the most recognizable brands in entertainment.
He didn't inherit it.
He didn't get a lucky break. He failed his way there, one no at a time - and in this conversation, he breaks down exactly how.
We get into why failure is a tool, not a setback.
Why your business is a vehicle, not the destination.
Why the only person you're actually competing with is yourself.
And what legacy really looks like when you're still in the middle of building it.
This is one of the most honest conversations I've had on this show.
Rick holds nothing back.
What we cover:
How he went from $300 in his pocket in Miami to global licensing deals.
Why getting made redundant was the best thing that ever happened to him.
The two things that will make or break any entrepreneur: people and finance.
How to find and seize the right opportunities.
Why failure is a motivational tool, not a stop sign.
What legacy means when you're still in the middle of building it.
Connect with Rick:
Website: ricklowe.co.uk
Podcast: Maverick Mindset
Journey to Legacy:
Website: journeytolegacy.org
YouTube: https://www.youtube.com/@WayneVeldsman
If this episode added value, leave us a review - it helps get this conversation in front of more people who need to hear it.
The 4 Things AI Will Never Replace | Ross Barnes - 25 years in AI & tech | JTL 151
2026/05/19
Ross Barnes spent 25 years in tech and advertising, ending up as Global CTO at a WPP agency where he helped scale the business from 15 people to over 1,500, and revenue from $80M to over $1B a year.
He's led AI and data strategy for Toyota, Lexus, EA Sports and British Airways, has been featured on the BBC and Bloomberg, and now runs the Galahad Group, helping companies actually use the AI tools they keep buying.
In this conversation, we get into why most AI transformations fail before they start, the four human values AI will never replace, what it actually takes to scale a company and a culture, and what changed for Ross after a late diagnosis of ADHD and autism at the top of his career.
Find Ross: Galahad Group: https://www.thegalahadgroup.com/
Pull Focus: https://pullfocuscoaching.co.uk/lander?oref=https%3A%2F%2Fwww.google.com%2F
LinkedIn: https://www.linkedin.com/in/rossbarnes/
Join the community: journeytolegacy.orgLeave a review if this added value - it helps the show grow.
The Most Dangerous Place You'll Ever Live Is a Nice Enough Life | Krisztian Kiraly | JTL 150
2026/05/05
What happens when you build a whole career — only to realize the life you created is no longer the life you want?
In this episode of Journey to Legacy, I sit down with Krisztian Kiraly, from OptiMonk, to talk about one of the most honest reinvention stories I've heard.
Krisztian went from 15+ years on cruise ships, to hitting burnout, losing his first business to bankruptcy, and rebuilding his entire life through digital marketing, relentless learning, and refusing to stay comfortable.
But this conversation isn't just about the pivot. Krisztian gives some of the most practical, no-nonsense advice on what it actually takes to grow an e-commerce business - including the 5 KPIs every store owner must know, why opinions are completely irrelevant in digital marketing, and how AI is changing the future of online shopping through hyper-personalisation.
In this episode:
Why "nice enough" is the most dangerous place you can liveThe 5 KPIs every e-commerce owner must trackWhy data beats opinions every single timeHow Krisztian went from zero digital marketing experience to running a full-stack agencyWhat separates growing e-commerce stores from stagnant onesHow AI and hyper-personalisation are changing the game right nowTry OptiMonk free:
https://www.optimonk.com Use code JTL50 for 50% off your first 3 months.
Connect with Krisztian Kiraly:
LinkedIn:https://www.linkedin.com/in/christian-kiraly/ YouTube: https://www.youtube.com/@OptiMonkcom
Journey to Legacy:
Website: https://journeytolegacy.org/
YouTube: https://youtu.be/BiWgTCyhulo
What You Won't Sacrifice, Will Become The Sacrifice | Marco Duarte founder of Duarte Media | JTL 149
2026/04/28
At 18, Marco Duarte left hisfamily in Guatemala on a full athletic scholarship and moved to the United
States - knowing almost no one, barely speaking English, and learning to swimin a very different kind of deep end.
Then, when most people would have settled, he moved again - this time to South Africa, a country he had never lived in, to build a business from scratch.
He now runs Duarte Media, a performance marketing agency in Cape Town helping small and medium businessesget real, trackable results from Google and Meta ads.
In this conversation, Marco gets into:
→ Why getting comfortable oncamera is the #1 move for entrepreneurs with a small ad budget
→ The difference betweenbusinesses that just run ads and businesses that actually grow from them
→ What it truly costs to chaseyour dreams across continents
→ A single line from a movie hehated that completely changed how he approaches fear
→ Why every opportunity has awindow - and windows close
This one hits different. Marco is the real deal - roots intact, cheap pen in pocket, and a philosophy that will stay with you long after this episode ends.
"What you're notwilling to sacrifice becomes the sacrifice."
Connect with Marco:
https://www.linkedin.com/in/marcocabreraduarte/
Become part of the Journey to Legacy Community/ for more information: journeytolegacy.org
He managed $250M in real estate at 25 - then drained his 401k to start over | Tyler Dunagin | JTL 148
2026/04/21
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
He Lost Everything & Built an Empire | Mike Milligan, Founder of One Oak Financial | JTL 147
2026/04/14
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
He Quit Investment Banking After One Trip… Here’s Why | Christopher Hill | JTL 146
2026/03/31
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/
Podcast reviews
Read Journey To Legacy podcast reviews
The Definition of 5 Stars 2025/11/19
Great Conversationalist
Wayne is a great conversationalist. Asks the right questions, interviews the right people. Huge fan
Douglas E. Noll JD MA 2025/07/06
Inspirational and insghtful
This is by far one of my all-time favorite podcasts! The way that Wayne overdelivers EVERY SINGLE TIME is incredible. If you’re an entrepreneur, this ...
esna_v 2024/10/16
Motivation to be better
This podcast is for people that are interested in growing in life. All aspects of life. Love love love this podcast! Wayne is generous with his knowle...
mommalabs 2020/08/09
Love it!!
Super amazing podcast with the best host!! Highly highly recommended!
justdoitgirl96 2020/05/05
Powerful Podcast
Work - Grind - Hustle is an outstanding show that shares insights, strategies, and so much more to benefit the impact driven entrepreneur! Wayne overd...
ninerz11 2020/04/17
Life is what you make it!
You’re always helping me to reset and think about things differently and reminding me that I have the ability to change my life by changing my mindset...
MichelleThompson90 2020/03/13
Wayne is on point!
Tanglible advice for business tools! He is also great at interviewing... He really digs in deep past just scratching the surface! Seriously, give it...
wynand12 2020/02/12
Highly recommend 👌🏼
Work Grind Hustle is full of awesome value, tips, and tricks from a guy who is just working hard trying to make the American Dream come true! Tune in,...
Cauveé - Inspiration Engineer® 2020/02/04
Wayne’s A Beast
Great interviewer, knows how to get the guest to share a depth of information .
_Zak1950 2019/12/27
Phenomenal Stories
The stories (and life lessons) was told in this podcast are exciting, captivating, and always include a valuable life lesson to make us all better peo...
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