Between Now and Success

Dan Haylett, a marketing director and financial planner experimenting with AI workflows. Alan Smith, a UK-based planner and CEO who has adopted AI in practice. They debate AI's rapid commoditization of technical advice. They discuss empathy's role, regulator and fiduciary risks, firm redesign for AI-first workflows, and which advisors will prosper as the industry bifurcates.

According to a recent study from Schwab Advisor Services, 63% of advisors are now using AI in some capacity. However, the RIA AI landscape remains highly experimental: only about 10% of firms report having fully integrated AI into their core strategy, while 30% say they are still just experimenting. So, if 2025 was the year of the AI notetakers, how can firms take the next step and truly harness this massive technological shift through the rest of 2026? On today's show, I welcome back Lisa Salvi, Managing Director of Business Consulting and Education at Schwab Advisor Services. We discuss the current pace of AI innovation and why AI is forcing advisors to redefine their core value proposition and how they communicate it to the marketplace.

Andy Schwartz, CEO and managing partner who helped scale OnePoint from a startup to ~$15B, shares his career arc and leadership approach. He talks about reinvesting to build capacity. He explains shared equity for committed partners. He describes centralization, preserving advisor autonomy, and plans to scale further while preparing for AI and higher-end advice.

I recently had the pleasure of joining Dave Zoller on his YouTube channel, Streamline My Practice, to discuss something I've been thinking deeply about lately: the difference between owning a business and being owned by your business. If you're a financial advisor wondering whether you've built a thriving enterprise or just created a demanding job for yourself, this conversation is for you. Dave and I discuss: The Four Levels of Advisory Business Evolution The Identity Shift That Changes Everything The Power of a Compelling Three-to-Five-Year Vision Two Real-World Examples of Extreme Freedom The Get-Keep Framework Technology, AI, and Practical Action Steps for Advisors

Most people spend their lives trying to eliminate tension: Work or rest. Control or flow. Clarity or creativity. But a well-lived life isn't free of tension—it's guided by how we hold it. In this podcast, I walk through the three polarities I'm using to guide my life and work in 2026, and reflect on how last year's polarities shaped some of my most meaningful experiences—from sailing and writing to health, family, and business. Rather than problems to solve, these are tensions to navigate—and learning to hold both sides has quietly changed how I make decisions, set direction, and define success. My three 3 Polarities for 2026 are: Mythos – Method Living a meaningful story and building the discipline to bring it to life. Compass – Wind Setting a clear direction while adapting to changing conditions. Precision – Poetry Writing and thinking with clarity without losing what moves people. Along the way, I also reflect on: Why "balance" often leads to frustration How experience earns you the right to loosen your grip What sailing teaches us about leadership and decision-making Why rest isn't laziness—and control isn't always wisdom This conversation is for leaders, advisors, creators, and anyone who senses that life is asking for integration, not optimization. If you've ever felt pulled between two good things—and wondered why choosing one never feels right—this podcast is for you.

Guest: Nikki Henderson, a world-class professional sailor. In 2018, Nikki became the youngest skipper to lead a team in the Clipper Round the World Yacht Race. At the age of 25, over the course of more than 40,000 miles of ocean racing, Nikki led a diverse team of mostly amateur sailors from 16 countries to an extraordinary second place finish. She's also skippered numerous transatlantic races and won the Race to Alaska. In a Nutshell: How do you define your job as a leader? Nikki Henderson says that what she does as a skipper is pull together disparate individuals, build them into high-performing amateur teams, and then compete in the most extreme sailing races in the world. I experienced Nikki's leadership first hand a few weeks ago when I sailed with her in the Caribbean 600 as part of her amateur crew. This was a grueling 600-mile race around 11 Caribbean islands. Despite long odds, we ended up finishing third and celebrated on stage with our prize: a big bottle of rum. On today's show, Nikki Henderson and I discuss making life transitions, paradoxes and polarities in leadership, and decision-making under pressure and uncertainty.

The discussion delves into personal growth from 2024 and the introduction of polarities for 2025. Balancing dreams with everyday life emerges as a key theme, emphasizing the tension between ambitions and family connections. The speaker shares insights on transitioning from stability to entrepreneurship and finding flow amidst challenges. Practical strategies are offered for navigating the balance between control and flow, encouraging listeners to embrace life’s cycles in a holistic manner.

Guest: Dr. Preston Cherry, AFC®, CFT-I™, CFP®, Ph.D., an entrepreneur, coach and speaker. Dr. Cherry is the creator of the Life Money Balance™ approach and founder of Concurrent Financial Planning. His new book is Wealth in the Key of Life: Finding Your Financial Harmony. In a Nutshell: "Songs in the Key of Life" is one of Stevie Wonder's most famous albums. In a similar vein, Dr. Preston Cherry wants people to find that kind of harmony between their money, their values, and their lives. And advisors who can help folks create a financial life that really sings are going to connect more deeply with clients and empower them to live -- and plan -- with more intention. On today's show, Dr. Preston Cherry and I discuss his new book and his unique perspective on how to bring purpose, balance, a "permission to prosper" and a little bit of rhythm to your financial planning process.

Kendra Wright, owner of Rebel Media Agency and former rock 'n roll marketer, shares unique insights from music to finance. She emphasizes the power of great copy and how it should reflect the voice of clients. The conversation dives into effective website strategies, showcasing real-world examples to help financial advisors enhance engagement. Kendra also highlights the importance of storytelling in marketing, utilizing client reviews, and crafting websites that resonate with ideal clients, ultimately showcasing how authentic communication drives success.

After I left Peak Advisor Alliance (now Carson Coaching), I settled on the idea of starting my Between Now and Success podcast as part of my next chapter. I figured podcasting would be a great way to stay in touch with people in our industry, keep networking, and learn from the best of the best. Now, 10 years later, across five separate podcasts, I've recorded more than 850 episodes, the vast majority of which are interview shows. Thanks to podcasting, I went from having a handful of trusted mentors to learning from hundreds of world-class teachers. While I could easily list dozens of unique and actionable ideas I've learned from a decade of podcasting, these 10 insights stand out.