HeyJaredJourney To Legacy
The Journey to Legacy podcast (formerly Work Grind Hustle) is a transparent look into the crazy world of entrepreneurship and what it truly takes to leave a legacy in this world.
- Indexed episodes, last 90 days
- 5
- Latest publication
- Sep 25, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 23, 2026
Latest episodes
He Reached the C-Suite and Lost Himself | Graham Skidmore on Burnout and Identity | JTL 158 (opens the original)
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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 car
The Day I Fired My Wife| Rob Ferguson on Family First vs Business First | JTL 157 (opens the original)
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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 b
How to Actually Get Out of Your Comfort Zone | Neil Thubron, Arctic Ultra Winner | JTL 156 (opens the original)
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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 train
Why You're Avoiding Your Own Business Numbers | Rebecca Irey, 35 years in finance | JTL 155 (opens the original)
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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
Financial Planning Ignores 25% of Adults | Scott Barnes, CFP, Childfree Wealth | JTL 154 (opens the original)
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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 actuall
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