Interviews with Insurance agents and agency owners about building, growing, and maintaining their insurance business.
Want to Be Featured on Small Strides BIG Business?
Are you an insurance agent or agency owner with valuable insights to share?
We’re currently booking guest interviews focused on:
• Agency growth
• Sales strategies
• Leadership
• Industry trends
Apply here to be considered:
👉https://forms.gle/38sFcC6E8TE1ci7t5
All applications are reviewed weekly.
Host Krystal Small interviews Sonja Kuhn, founder of Mint Cover, about leveraging AI in insurance to enhance customer experience while preserving the human touch.
4 Jun 2026
Can AI Replace Doctors? The Future of Healthcare Explained
Krystal Small interviews Mark Seghers, CEO & Co-Founder of Inspire Health Tech, about AI's transformative impact on healthcare and decision-making.
28 May 2026
The Money Rules Nobody Taught You | Creative Finance & Infinite Banking with Travis Yoh
Host Krystal Small interviews financial educator Travis Yoh about creative wealth-building strategies like Infinite Banking and real estate investing, offering entrepreneurs practical insights for financial empowerment.
21 May 2026
From Startup to $50M: Lessons in Growth, Hiring & AI with Tad Nottage
Host Krystal interviews Aloha Insurance founder Tad Nottage about his 30-year journey building a $50M business through resilience, smart hiring, and prioritizing customer relationships.
14 May 2026
From Delivering a Widow’s Check to Changing Lives: Mark Zimmerman
Host [Host Name] interviews Mark Zimmerman, Founder of Aurifex Financial, as he shares how serving a widow transformed his insurance business into a mission of financial protection and education.
7 May 2026
“Why Most People Don’t Understand Disability Insurance (And It Costs Them)”
Independent insurance advisor and educator Michael Wish explains why disability insurance is misunderstood and shares insights on adapting to industry changes and client-first success in this interview.
30 Apr 2026
The “When vs If” Strategy That Changes How You Build Wealth | Banking Bros
Host Krystal interviews Banking Bros Jeremiah and Jonah Dew about the "when vs if" strategy for building wealth through infinite banking.
23 Apr 2026
The Entrepreneur’s Balancing Act: Law, Therapy & Leadership| James Ahearn
Host [Host Name] interviews attorney, therapist, and entrepreneur James Ahearn about balancing law, mental health, and leadership to build a thriving service-based business.
16 Apr 2026
Negotiating Medical Bills & Finding Better Coverage | William Allison
William Allison, founder of Modern Healthcare Plans of America, reveals how to negotiate medical bills and find better coverage, offering practical strategies to save thousands.
9 Apr 2026
From Crisis to Thriving Virtual Agency | Dave McFadden on Insurance, Resilience & Going Independent
Dave McFadden shares how he and his wife Cindy transformed their insurance agency from crisis to a thriving virtual business by going independent and focusing on client relationships.
2 Apr 2026
From $9K to $1K: AI Is Transforming Healthcare Costs | Assaf Frajman
From $9K to $1K: AI Is Transforming Healthcare Costs | Frajman
Medical bills are one of the leading causes of financial stress—and often, they’re wrong.
In this episode of Small Strides Big Business, Krystal Small sits down with Assaf Frajman, a physician-turned-entrepreneur and Co-Founder of OctiHealth, to explore how AI is transforming the way medical bills are reviewed, reduced, and understood.
After witnessing a $9,000 medical bill corrected to just $1,000, Assaf set out to solve a problem impacting millions. Today, his company helps reduce healthcare costs by an average of 61%—not just for individuals, but for entire organizations.
They also dive into Assaf’s personal journey from medical school to tech, and what it really takes to pivot into a new career path.
26 Mar 2026
Built a Thriving Insurance Agency Serving Hispanic Families |Lidia Rodriguez
What does it really take to build a successful insurance agency from scratch — in a new country — while serving an underserved community?
In this episode of Small Strides Big Business, we sit down with Lidia Rodriguez, Co-CEO of Rewarding Insurance Agency in Holyoke, Massachusetts.
From knocking on doors in freezing temperatures to building a referral-driven agency rooted in trust, Lidia shares how personal tragedy shaped her mission to protect Hispanic families through final expense and life insurance education.
This episode is about: ✔ Building a niche in the Hispanic community ✔ Turning hardship into purpose ✔ Why insurance is NOT a part-time career ✔ The truth about commission-based income ✔ Scaling an agency with systems and heart ✔ The power of referrals and community trust
Lidia and her husband Miguel are not just selling policies — they are changing financial futures through education, transparency, and cultural understanding.
If you're: • An aspiring insurance agent • A Latino entrepreneur • A small business owner • Or someone passionate about community impact
This episode is for you.
19 Mar 2026
The Silent Grind: Mindset, Service & Building a Business That Lasts| Dillon Taylor
Success isn’t built overnight — it’s built in the quiet moments no one sees.
In this episode of Small Strides, Big Business, Krystal sits down with Dillon Taylor, Founder & CEO of Ascent Financial Solutions, to talk about what entrepreneurship really looks like behind the scenes.
From spending nearly a decade in construction to building a thriving financial brokerage, Dillon shares the mindset shifts, leadership lessons, and service-first philosophy that shaped his journey.
This conversation goes beyond insurance and finance — it’s about identity, discipline, long-term vision, and building something that actually lasts.#EntrepreneurMindset #InsuranceIndustry #FinancialServices #SmallStridesBigBusiness #Leadership #BusinessGrowth #TheSilentGrind #EntrepreneurLife
12 Mar 2026
The Power of Loyalty in Business with Charley Tinsley
In this episode of the Small Strides Big Business podcast, host Krystal Small and Tiffany Peak interview Charley Tinsley, managing partner of TIG Thomas Insurance Group. Charley shares his journey from a family farming operation to building one of the largest Medicare agencies in the country, with over 1000 FA and P&C agents (Medicare agents and Employer Benefits agents). He emphasizes the importance of loyalty, education, and service in business, and discusses how technology has played a crucial role in managing growth and improving efficiency. Charley also offers valuable advice for new agents and those looking to scale their businesses, highlighting the significance of building strong relationships and finding a center of influence in the industry.
5 Mar 2026
Title: How One Insurance Agency Cut Costs by 70% & Boosted Retention to 93%| Ted Reardon
In this eye-opening episode of Small Strides, Big Business, hosts Crystal Small and Tiffany Peak sit down with Ted Reardon—a 40+ year insurance veteran, owner of Reardon Insurance (founded in 1920 by his great-grandfather), and managing partner of Virtual Agent Consultants.
Ted shares how he transformed his traditional brick-and-mortar agency into a fully virtual, service-center-driven model—eliminating payroll headaches, slashing overhead, and freeing up time to focus on what really matters: clients and growth.
💡 You’ll learn:
✅ Why hiring qualified staff is nearly impossible—and the bold solution Ted implemented
✅ How shifting client service to carrier service centers increased retention to 93%+
✅ The exact moment he “pulled the trigger” in November 2020—and why it was the best business decision of his life
✅ How operating costs dropped from $2,000/month to just $325
✅ His 4 non-negotiable tips for new agents entering the insurance industry
✅ Why Google reviews and modern tech are non-optional in today’s market
Whether you're an insurance agent, agency owner, or entrepreneur looking to streamline operations and future-proof your business, Ted’s story proves that sometimes, the bravest move is stepping off the ledge—and trusting the net will appear.
26 Feb 2026
From “Failed Actor” to Insurance Titan | Jeff Arnold on Building a Business That Works Without You
What if the key to massive business growth wasn’t selling more… but selling less? In this episode of Small Strides Big Business, we sit down with Jeff Arnold — entrepreneur, founder of two highly successful insurance companies, and acquirer of 40+ agencies — to unpack the mindset shifts that transformed his career. Jeff didn’t start in insurance with a grand vision. In fact, he calls himself a “failed actor.” But through mentorship, discipline, and strategic thinking, he went from self-employed salesperson to true business builder. This conversation is packed with practical insights on delegation, recurring revenue, leadership, and leveraging AI the right way.🎙 Interested in being a guest on Small Strides BIG Business?Apply here: https://forms.gle/38sFcC6E8TE1ci7t5
20 Feb 2026
Welcome to Small Stride BIG Business Podcast | Official Trailer
Welcome to Small Stride BIG Business Podcast — a podcast where we talk about the ups and downs, what has worked, and what has been great learning experiences, and talks about the trends over the past decade, and what is to come in the world of insurance.
New episodes coming soon. Make sure to follow/subscribe so you don’t miss the launch!
Who has been a guest on Small Strides BIG Business
Names identified in recent episode analyses. Showing up to five guests.
Sonja Kuhn
Mark Seghers
Travis Yoh
Tad Nottage
Mark Zimmerman
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