What does a successful financial planning career actually look like behind the scenes? In this episode, Preston Henry, Director of Financial Planning at Sugarloaf Wealth Management, shares the winding and unconventional path that took him from golf course conversations and banking roles to becoming a leader inside a growing RIA. Along the way, Preston opens up about the risks, career pivots, mentors, and mindset shifts that shaped his journey through multiple areas of the financial services industry.

Listen in to learn how he navigated transitions from banking and lending into wealth management, why he chose learning opportunities over short-term financial security, and how relationships consistently opened new doors throughout his career. You'll get valuable insight into the evolution of the advisory profession, the importance of CFP education, building operational leadership inside an RIA, and how advisors can position themselves as indispensable team members while continuing to evolve professionally.

You can find show notes and more information by clicking here: https://tinyurl.com/mr384j55

What happens when a psychology major discovers financial planning and decides to completely rethink how advice can be delivered? In this episode, Andy Baxley shares his journey from teaching English in South Korea to working at large financial institutions, discovering the fee-only RIA world, and ultimately launching his own firm, Two Trails Financial Planning. Andy opens up about the career pivots, self-doubt, and entrepreneurial lessons that shaped his path, along with the mindset shifts that helped him finally make the leap into business ownership.

We also dive into how Andy is using AI to create more personalized, high-quality client experiences rather than simply automating tasks or reducing costs. He explains how advisors can use AI tools to build bespoke solutions for clients, why understanding psychology and communication is becoming even more important in the age of AI, and how newer planners can find the right career path based on their personality, strengths, and long-term goals. If you're interested in entrepreneurship, career growth, financial planning, or the future of AI in advice, this episode is packed with practical insights you won't want to miss.

You can find show notes and more information by clicking here: https://tinyurl.com/mrxxx5jw

What does it really take to build a successful financial planning career, and how much of it comes down to education, persistence, and understanding human behavior? In this episode, Gary Clement shares his unconventional journey from a math major with an interest in investments to an experienced financial planner, educator, and PhD holder. He walks through his early days in the industry, the lessons learned from working in high-pressure sales environments, and the pivotal experiences that shaped his transition into financial planning and education.

Listen in to learn why behavioral finance is becoming central to the future of advice, how advisors can help clients overcome suboptimal decision-making, and why understanding human behavior is just as important as technical knowledge. Gary also unpacks how real-world experience, licensing, and continuous education can shape long-term career success in financial planning. You'll hear about career strategy for new planners, the importance of early job experience, and how to build momentum in a competitive industry.

You can find show notes and more information by clicking here: https://tinyurl.com/3tk7yawv

What does it really take to build a successful financial planning career when you're starting from scratch? In this episode, Evan Fears, CFP at Vision Financial Group Georgia, shares how he entered the financial planning industry straight out of college with no guaranteed salary, no inherited client book, and plenty of obstacles standing in his way. From being mistaken for a high school student while meeting with clients to navigating the pressure of building trust as a young advisor, Evan opens up about the realities of growing a business in the early years of his career.

Listen in to hear how he found his niche working with educators, why grassroots relationship-building mattered more than flashy online marketing, and how he steadily built confidence, credibility, and a loyal client base that eventually led to becoming a partner at just 29 years old. Evan also offers insights on mentorship, culture fit, finding the right niche market, and what he says is one of the most important skills for new planners entering the profession today.

You can find show notes and more information by clicking here: https://tinyurl.com/mvk22jvs

What happens when you stumble into a career you didn't even know existed and end up building a business entirely on your own terms? In this episode, Kaleb Paddock, founder of Ten Talents Financial Planning, shares his unconventional journey into financial planning and the lessons he learned along the way.

From discovering the profession through third-party administration work to earning his CFP and gaining hands-on experience at an RIA firm, Kaleb walks through the pivotal moments that shaped his career. Listen in to learn how he made the leap to entrepreneurship, the challenges of starting from scratch in a new state, and how he evolved his business model into a virtual family office designed to better serve his clients.

You can find show notes and more information by clicking here: https://tinyurl.com/3ykhxaza

Could your strengths lie outside the traditional advisor path? My guest today is Brian Abatemarco, who navigated his career from financial planning into sales, and ultimately into the world of AI startups. From managing clients early in his career to discovering a passion for business development, Brian shares how leaning into your natural strengths can completely reshape your trajectory.

Listen in to learn how AI is actually being used inside advisory firms today (and why it's not replacing advisors anytime soon), how automation can transform client service and operations, and what it really looks like to take a risk on something new. If you've ever questioned whether you're on the "right" path or wondered how to pivot without starting over, this episode offers a practical and honest look at building a career that works for you.

You can find show notes and more information by clicking here: https://tinyurl.com/p4c5dy7n

What if the key to standing out in your career is starting before you feel ready? In this episode, Cassidy Vines, a financial planning student at Temple University and winner of the 2025 New Planner Recruiting Tuition Scholarship, shares how she took the initiative early to build real-world experience before graduating. You'll learn how she discovered financial planning, why she made the switch from marketing, and how she turned curiosity into a clear career path.

Listen in as Cassidy shares how she secured multiple internships (including through cold outreach), how hands-on experience accelerated her learning, and what she's looking for in a future employer. From leveraging part-time jobs into transferable skills to building confidence in interviews, this conversation is packed with practical insights for anyone looking to break into financial planning and stand out while doing it.

You can find show notes and more information by clicking here: https://tinyurl.com/2s43d7np

What do you do when rejection, setbacks, and uncertainty hit early in your career? In this episode, Francesco D'Amore shares how he turned college rejection, uncertainty about his career path, and limited resources into a clear plan to break into the financial planning profession. From teaching himself to pass the SIE exam using only YouTube to transferring schools and landing internships through networking, Francesco explains how curiosity and persistence shaped his journey.

Listen in to learn how to stand out as a student or career-changer, why networking conversations matter more than formal applications, and how internships actually turn into opportunities. You'll hear Francesco's long-term plan for becoming a financial planner, pursuing the CFP certification, and building a career in the industry.

You can find show notes and more information by clicking here: https://tinyurl.com/3jha4f6b