What if the most valuable lessons in business and life aren’t found in headlines, but in the stories people only share when no one’s listening?
I’m Stephanie Fox: mother, pilot, and commercial real estate professional. I built and sold my first business by 27 and have been navigating the world of entrepreneurship and real estate ever since. In Wisdom in Wealth, I sit down with influential business leaders and community changemakers across Arizona to uncover the raw, unfiltered stories behind their success.
These conversations go beyond profit and prestige—we talk about risk, resilience, and the wisdom gained in moments of uncertainty. If you’re driven to grow, lead, and live with purpose, you’re in the right place.
Wisdom in Wealth — because real wealth starts with real stories.
Tony Holland: Inspiring Success from Humble Beginnings
Stephanie introduces Tony Holland, CEO of Global Premier Benefits and managing partner of Integrity. He grew up in Brunswick, Maryland in a fatherless, abusive environment and stayed busy through sports and school activities to survive. After Johns Hopkins and failed attempts at other paths, Tony hit rock bottom living in a van while bartending until a friend introduced him to insurance, where he quickly found success, earned renewals-based residual income, invested aggressively, and built wealth. He and his wife Kathy later founded Holland Insurance Group (2000) and Global Premier Benefits (2009), raised three children, and prioritized family time through financial freedom. Tony shares lessons on faith, taking risks, learning from failure, forgiveness, identity discovery through Ancestry testing, overcoming years of litigation, pivoting into Medicare leadership, giving back through coaching, and defining wealth as character and relationships, not just money.
16 Oct 2026
Landlord to Investor: The Pathway to Passive Real Estate with Ashley Romiti
Exit Strategies for Tired Landlords: 1031 Exchanges, DSTs, 721 UPREITs, and Oil & Gas with Ashley Romiti
On the Wisdom and Wealth Podcast, host Stephanie interviews Ashley Romiti, president of GCA 1031, about tax-deferred exit strategies for “tired landlords” and real estate investors seeking passive, institutional-quality investments while deferring capital gains. Romiti explains Delaware Statutory Trusts (DSTs) as a hands-off 1031 exchange option that can diversify across asset classes and markets, sharing an example of a California duplex sale with $2 million in equity reinvested into five DSTs, including oil and gas, for monthly passive income. She outlines the 721 UPREIT two-step strategy (1031 into DST, then 721 into a REIT) and discusses 1031-eligible oil and gas mineral rights investing and its volatility. They touch on refinancing pressure, “extend and pretend,” DST sponsor due diligence, and common investor discomfort with illiquidity and relinquishing control. Romiti urges investors to plan exits early and explore options before the 45-day exchange clock starts.
Learn more about Ashley's services at gca1031.com.
Landmark Title is proud to sponsor the Wisdom in Wealth podcast. Learn more about the leading title and escrow experts at ltaag.com.
2 Oct 2026
The Limited Partner Frustration That Became a Startup: Alex Taylor on Commercialize IQ
Stephanie sits down with Alex Taylor, founder and CEO of CommercializeIQ, a serial entrepreneur who has owned and operated commercial real estate and is a seasoned investor in deals nationwide.
Alex talks about the 90 days after he sold his last company, asking CRE professionals one question: what doesn't work for you today? The answers kept pointing to scattered, outdated data, a problem he knew firsthand as an investor having to log into multiple different portals simply to view PDFs.
That became CommercializeIQ, an AI platform that brings leases, contracts, and relationships into one place, answers questions like "Can I bring a certain retailer into this center?" in seconds, and assigns the work that follows. He and Stephanie also cover why CRE is still in "batting practice" on AI, the security risk of putting leases into a $20 chatbot, and why companies that try to build it in-house tend to call back six months later.
Wisdom and Wealth is proudly sponsored by Landmark Title — Arizona's title and escrow experts. Learn more at LTAAG.com.
Learn more about CommercializeIQ at commercializeiq.com
Keep up with Alex on LinkedIn: linkedin.com/in/alexandertaylor86/
Who has been a guest on Wisdom in Wealth with Stephanie Fogelson
Names identified in recent episode analyses. Showing up to five guests.
Rick Huffman
Josh Carmona
Keaton Merrell
John Orsak
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Podcast Authority Score: 33 / 100
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Questions about Wisdom in Wealth with Stephanie Fogelson
Who hosts Wisdom in Wealth with Stephanie Fogelson?
Stephanie Fogelson host the show. Published by Stephanie Fox.
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The show publishes bi-weekly, based on its RSS feed.
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