In this episode, I had the pleasure of sitting down with Ashley Quamme, a licensed marriage and family therapist and the founder of Beyond the Plan. Ashley is someone I’ve admired for a long time, and this conversation is packed with powerful insights into the intersection of psychology, relationships, and personal finance.

Ashley shares her unique journey—from launching a private therapy practice focused on couples, to navigating military life as a spouse, to eventually blending her clinical background with the world of financial planning. We explored what financial therapy really means and how deeply emotional and relational our financial decisions truly are. Ashley’s passion for helping people understand the “why” behind their money behaviors is infectious, and her ability to make that practical for both advisors and clients alike is a real gift.

We also talked about how Ashley collaborates with financial advisors as a Chief Financial Behavior Officer and what it means to create emotionally safe planning spaces. I loved her thoughts on how validation, curiosity, and even open-ended questions can transform client meetings. Whether you’re a financial professional or someone navigating your own money story, Ashley’s insights are so relevant.

Ashley’s wisdom and vulnerability in this episode are incredibly encouraging. She also reminds us that you don’t need to be a therapist to be therapeutic. If you care deeply about the people you serve, there are ways to show up with empathy, insight, and skill—even when money is emotional.

https://www.linkedin.com/in/ashley-quamme/

https://www.beyondthefp.com/

https://www.planningandbeyond.com/

I’m excited to welcome Greg Young on the podcast today. He is the founder of Ahead Full Wealth Management, a fee-only RIA based in Rhode Island. As a Navy veteran himself, his focus there is working with military, government employees, and educators through financial planning, investment management, and tax planning and preparation.

In our wide-ranging discussion Greg shares his personal journey of initial interviews trying to determine where to start his career in financial services and his thoughts on the pros and cons or working in the major insurance companies and broker dealers. It may be especially helpful to hear why Greg benefited from the training programs tied with his military background as well as the challenges of the sales culture he faced.

Greg has always been interested in education so he shares the various licenses, degrees, and certifications he has pursued including his current PhD program as well as teaching in a variety of roles. Along with that though, we explore the challenges of determining limits of these kinds of side hustles and the tradeoffs in firm growth they can have.

Lastly, we share about the personal experiences of learning from others on the career journey including the benefits of masterminds, mentorship, and giving back.

If you are interested in breaking into your first role in financial services, exploring alternative income and career paths in parallel with financial planning, or want to hear some hard-earned lessons learned from a six year RIA owner, you can find those nuggets of wisdom here. Here’s my interview with Greg!

https://www.linkedin.com/in/ashley-quamme/

https://www.beyondthefp.com/

https://www.planningandbeyond.com/

I’m excited to welcome Dan Huffman on the podcast today. He is the founder of Cornerstone Financial Planning, a fee-only RIA based in CO. His focus is on working with those in the real estate community so we spend a lot of time talking about that type of expertise, the planning and tax considerations for that niche, compliance considerations, and balancing those goals with other aspects of financial planning especially when so many clients think about real estate in more emotional aspects.

Dan shares his story of learning about aspects of personal finance in the FIRE community and some of his initial challenges of trying to market to them as prospective clients. We also touch on many of the places that Dan has learned from and educational resources you might also benefit from.

I appreciate Dan’s candor as he navigated gaining his confidence early on before really opening up his marketing and experiencing fast growth in the past year or so. With that growth, we also discuss becoming more efficient through processes and delegation.

Lastly, we wrap up talking about what Dan sees coming up next and how he is seeking to serve his clients, a broader community, and balance those against the purposeful work in a life of financial independence. Here is my interview with Dan!

https://www.linkedin.com/in/daniel-huffman-cornerstonefiplanning/

https://cornerstonefiplanning.com/

https://www.biggerpockets.com/

https://militarytaxexperts.org/

https://www.realdata.com/

https://www.ccim.com/

https://www.therealestatecpa.com/

I’m excited to welcome Ryan Guina on the podcast today. He is the founder of the Military Wallet, one of the longest running and most respected personal finance websites focused on the military audience. Ryan served over six years in the United States Air Force as an aircraft mechanic, then joined the Air National Guard in 2014 after an 8.5-year break in service which we talk about integrating the challenges of that with his entrepreneurial journey.

In our wide-ranging discussion Ryan shares his personal journey of sharing his discoveries on a blog during the early days of this content creation, the community he learned from along the way, and how it evolved from an initial side hustle into a full-time career. I especially appreciated his advice around looking for ways to help others careers selflessly and in so doing build a community of people who are within a few levels of where you are at.

Ryan has years of experience with SEO or search engine optimization which we also talk about including helpful resources and how to capture an audience to nurture over time. We also discuss the challenges more recently from the rise of AI and its impact on web traffic.

If you are interested in content creation, building an audience online, or exploring alternative career paths related to personal finance you can find lots of nuggets in this episode. Here’s my interview with Ryan!

https://www.linkedin.com/in/ryanguina/

https://themilitarywallet.com/

https://www.semrush.com/

https://moz.com/

https://ahrefs.com/

I’m excited to welcome Valerie Rivera on the podcast today. She is the founder of First Gen Wealth, an RIA specializing in no shame, no judgement financial advice for First Gen wealth builders in their 30s and 40s. I invited Valerie on the podcast to help share her story of overcoming lots of barriers including race, family of origin, education, class, financial safety net, and much more. I love her transparency in sharing each stage of her career journey and how she persisted in finding a path forward, even in the midst of challenge after challenge.

She is part of just over 1% of Latinas holding the CERTIFIED FINANCIAL PLANNER designation, the gold standard of financial planning. Valerie is a member of the Financial Planning Association (FPA), XY Planning Network, Fee-Only Network, The National Association of Personal Financial Advisors (NAPFA), and the CFP Board Diversity Advisory Group. She has contributed to publications such as The New York Times, The Wall Street Journal, Forbes, Business Insider, and others regarding her expertise in personal finance.

In my discussions over the years with people in the military space, it often comes up that it feels daunting or different to try and make the leap into financial planning when you might not feel like you fit in. It’s a stark fact that financial planning isn’t as diverse as the population as a whole, much less those of us who want to serve based on our backgrounds or communities. If you feel like you might also struggle to fit in or find your way based on initial or past experiences in financial services as a whole, I hope you can take away some encouragement or inspiration to follow Valerie’s example and not give up. We need you in this valuable profession!

Here’s my interview with Valerie!

https://1genwealth.com/

https://www.linkedin.com/in/valerie-rivera-cfp/

I’m excited to welcome Curt Sheldon on the podcast today. He is the founder of C. L. Sheldon and Company, a flat-fee RIA focused on serving senior military officers. Curt first launched this firm more than 14 years ago and offered flat fee engagements with investment management long before this became more common. His firm also prepares more than 300 tax returns.

In this wide-ranging interview Curt shares how his early interest in finances started during his academics studies during undergraduate, masters, and CFP coursework while on active duty. Listen for his story about a bad experience early on with being sold some unsuitable products and how this impacted his view of the industry. We talk about his decision to pursue the EA and how tax planning and preparation has shaped much of his client experience over the years.

We also explore the team growth of his firm and his vision for the future, both in his company but also in the broader industry. Curt shares his perspective and advice for job seekers including how to focus on the mission and vision of the firm you are interviewing with. Lastly, we reflect on how much has changed even just over Curt’s firm and what he sees as some of the biggest transitions and opportunities.

https://www.linkedin.com/in/curtis-curt-sheldon-cfp%C2%AE-ea-20a51b19/

https://clsheldon.com/

In this short bonus episode, Paul Allen rejoins us to share the exciting news about the MQFP live exam prep course coming up at MilMoneyCon25. We chat through what that looks like, what you can expect to learn, how much it costs, when to plan travel, integration with the MilMoneyCon conference schedule, and a special opportunity for some scholarships! Hope to see many of you listeners there!

https://milmoneycon.com/

https://mqfp.org/review-course-at-milmoneycon/

I’m excited to welcome Stacy Miller on the podcast today. She is the founder of Bayview Financial Planning, a flat-fee RIA focused on serving women, widows, and military and veteran families. Stacy is a military spouse to a retired U.S. Army officer. Married for over 30-years to her husband, Jody, who served 28-years in the military, Stacy has experienced many positive and negative transitions. She has seen firsthand how those transitions can impact women, widows, and military/veteran families. Together, her military family moved 14 times during their service, and as a result, Stacy was often unemployed or underemployed. She therefore recognizes how important it is for women, especially, to feel confident in their own future financial security.

We chat about her exposure to personal finance as her family CFO holding down the fort during her husband’s long and varied military career. Like most military spouses, Stacy found a way to make it all work and built up an incredible skillset during those years across her varied experiences.

Stacy shares how her initial experiences with financial advisors made her wary of going down that career path before a colleague finally convinced her to join an RIA. While it was a great training ground and opportunity to do lots of things, she felt the pull of real financial planning for families and individuals that was different than the institutional money management that prior firm did.

So, Stacy took the leap into launching her own firm earlier this year and we catch her at the 6 month point where she is fresh in the trenches of marketing and working to get those first 10 clients. I love how she shares about the real reasons why she had to do this for herself and how work and identity plays such a key role for her in this decision. Lastly, she shares some really interesting advice she gives to fellow military spouses also exploring careers in this profession.

https://www.linkedin.com/in/stacymillercfp/

https://bayviewfp.com/