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Ashley is joined by Adam Chapman, founder of YESmoney, for a conversation about what can happen when advisors rethink the language and structure of the planning process. Adam talks about why some clients, especially retirees, may not know how much they are allowed to dream until the plan gives them permission.

Together, Ashley and Adam talk about the difference a simple wording shift can make, including why Adam renamed the traditional discovery meeting a “blue sky session.” They also touch on client behavior, collaboration, retirement spending, and how advisors can create space for conversations that go beyond the numbers.

Episode Highlights:

• Why Adam renamed discovery meetings as Blue Sky Sessions
• How retirees can leave dreams off the table before they know what is possible
• Why clients may need permission to say the bigger dream out loud
• How small language changes can shift the way clients show up
• Why collaboration matters before, during, and after the planning meeting
• How client money stories can shape what they believe is possible
• Why the financial plan needs to speak to the client, not just the numbers
• How advisors can build meetings around the places clients usually get stuck

This conversation is for financial advisors who want their planning process to feel less like data gathering and more like a place where clients can say what they really want.

RESOURCES AND GUEST INFORMATION

Adam likes to joke he's the financial planner who helps people spend money, not save it. As the Founder of YESmoney, he's spent nearly two decades helping retirees overcome the beliefs, behaviours, and emotions that prevent people from enjoying their wealth. Now, he's on a mission to help every retiree intentionally die with less. His contrarian take on retirement spending has landed him in The Globe and Mail, The Wall Street Journal, Money Sense, Investment Executive, and Wealth Professional.

Connect with Adam Chapman:

• LinkedIn

Connect with Host Ashley Quamme:

• Podcast Website: https://www.planningandbeyond.com
• LinkedIn: https://www.linkedin.com/in/ashley-quamme
• Beyond the Plan®: https://www.beyondthefp.com
• Monthly Newsletter: https://www.beyondthefp.com

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Join Ashley and Brendan Frazier, host of The Human Side of Money podcast, for a conversation about review meetings and why they matter more than many advisors realize.

Brendan explains the difference between reactive and proactive review meetings and talks about where review meetings can fall flat, especially when the meeting becomes a routine check-in instead of a chance to understand the client better, celebrate progress, and reconnect with what matters most. Brendan also explains why clients usually do not leave because of performance. They often leave because of communication breakdowns or because they no longer feel understood.

Episode Highlights:

• The difference between reactive and proactive review meetings
• Why review meetings are the anchor of the client experience
• Where traditional review meetings often fall short
• How to help clients reflect on progress
• Why satisfied clients are not always engaged clients
• How to relearn who your clients are as their lives change
• The four R’s of stronger review meetings: reflect, reassure, recalibrate, and reimagine

This conversation is for financial advisors who want review meetings to feel less routine and more useful for the client. Tune in for a clear way to rethink the meeting so clients leave feeling heard, understood, and clear about where they are going next.

RESOURCES AND GUEST INFORMATION

Brendan Frazier helps financial advisors master the human side of advice. As host of The Human Side of Money podcast, he explores how psychology, behavior, and emotion shape financial decisions. A former advisor, Investopedia Top 100 Financial Advisor, founder of Wired Planning, and Chief Behavioral Officer, Brendan helps advisors strengthen client conversations and relationships through behavioral science. He lives with his wife, Shannon, and their three children.

Connect with Brendan Frazier:

• The Human Side of Money Podcast
• LinkedIn
• Website
• The Ultimate Review Meeting course - get $100 off with this link!
• E50. What Is the Human Side of Money? A 50th Episode Conversation with Brendan Frazier

Connect with Host Ashley Quamme:

• Podcast Website: https://www.planningandbeyond.com
• LinkedIn: https://www.linkedin.com/in/ashley-quamme
• Beyond the Plan®: https://www.beyondthefp.com
• Monthly Newsletter: https://www.beyondthefp.com

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A client’s career is often one of the biggest drivers of their financial life, but advisors are not always equipped to help with it.

In this episode, Ashley talks with Kolby Goodman, career coach, keynote speaker, and author, about where career decisions and financial planning overlap.

Kolby shares how he moved from IT support into career coaching after realizing that his mix of technical skill and people skill helped him stand out, grow his career, and eventually help others do the same. Over the past decade, he has worked with more than 3,500 professionals to find better jobs, earn more, improve work-life balance, and build careers that feel more aligned.

Ashley and Kolby discuss why career coaching can be such a valuable resource for financial advisors and their clients. Many clients are dealing with burnout, layoffs, career uncertainty, or the pressure of staying in a role that pays well but no longer fits the life they want. Advisors may be able to show clients what is financially possible, but career coaches can help them figure out what comes next and how to move toward it.

Kolby also explains how advisors can recognize when a client may benefit from career coaching, including clients who feel stuck, worried about layoffs, unsure how to make a change, or ready to think more intentionally about their work.

Episode Highlights:

• How Kolby moved from IT support into career coaching
• Why career decisions are deeply connected to financial planning
• How advisors can support clients who feel stuck, burned out, or uncertain
• Why some clients need more than financial permission to make a career change
• How career coaching can help clients name their value and next steps
• When advisors should consider bringing in a career coach
• Why young graduates may need more support entering today’s job market
• How to build a career by design instead of falling into one by accident

This conversation is especially useful for advisors who want to better understand the role career decisions play in a client’s financial life and offer more complete support during major life and work transitions.

RESOURCES AND GUEST INFORMATION

Kolby Goodman is a career coach and keynote speaker who partners with wealth management firms and financial planners to support clients and their children through career transitions. He helps families navigate layoffs, career pivots, and the launch of new college graduates, all of which can affect a family’s financial and emotional picture.

In 2025, Kolby helped his clients secure an average salary increase of 22.5%. He is the author of Employed by Graduation and Employed by Graduation: The Parent Edition and brings 13 years of career coaching experience to conversations around wealth, career risk, and family planning.

Connect with Kolby Goodman:

• LinkedIn: https://www.linkedin.com/in/kolbygoodman

Connect with Host Ashley Quamme:

• Podcast Website: https://www.planningandbeyond.com
• LinkedIn: https://www.linkedin.com/in/ashley-quamme
• Beyond the Plan®: https://www.beyondthefp.com
• Monthly Newsletter: https://www.beyondthefp.com

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In this episode of Planning & Beyond®, Ashley talks with Dr. Dr. Amanda Craft, a researcher and educator whose PhD work focuses on cultural intelligence in financial advice.

Dr. Craft explains why culture matters in financial planning and why it is about more than race, ethnicity, or nationality. Culture includes values, lived experiences, communication styles, family expectations, and the assumptions people carry about money, safety, responsibility, and success.

Ashley and Dr. Craft further discusses how cultural values can shape client decisions, including investment choices, family financial obligations, property ownership, caregiving, and trust in financial systems, explaining why advisors may miss important context when they assume financial decisions are only individual decisions.

They also talk about practical questions advisors can ask to better understand a client’s values, including how money was talked about growing up, who else is involved in financial decisions, and what financial success means to the client.

Ashley and Dr. Craft offer a clear reminder that good advice requires more than technical knowledge. It also requires curiosity, cultural intelligence, and a willingness to understand the client’s world before making recommendations.

Episode Highlights:

• Why cultural intelligence matters in financial planning.
• How culture can shape client behavior and financial decisions.
• Why culture includes more than race, ethnicity, or nationality.
• Questions advisors can ask to better understand client values.
• How family, community, and lived experience can influence financial choices.
• Why advisors should review their onboarding forms for hidden assumptions.
• How cultural awareness can help advisors build stronger client relationships.

RESOURCES AND GUEST INFORMATION

Dr. Amanda Craft is an Associate Lecturer at Western Sydney University whose work explores the intersection of financial regulation, cross-cultural psychology, and behavioural finance. Her research examines how cultural and institutional dynamics shape financial advice relationships, client decision-making, and regulatory outcomes.

Connect with Dr. Amanda Craft:

• LinkedIn: https://www.linkedin.com/in/dr-amanda-craft-31335134b/
• Email: DrAmandaCraft@gmail.com

Connect with Host Ashley Quamme:

• Podcast Website: https://www.planningandbeyond.com
• LinkedIn: https://www.linkedin.com/in/ashley-quamme
• Beyond the Plan®: https://www.beyondthefp.com
• Monthly Newsletter: https://www.beyondthefp.com

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Kids are watching how money works, but that does not mean they understand it.

Join in as Ashley talks with Jamie Bossi, a financial planner, author, and mother of four, about helping kids build better money habits early.

Jamie shares how the idea for her children’s book series, Milton the Money Savvy Pup, started at home. After realizing her own child did not fully understand that online purchases still involved real money, Jamie began looking for simple ways to teach money basics in a way young kids could understand.

That idea became a children’s book series focused on concepts like earning, saving, spending, giving, waiting, making choices, and practicing gratitude. Jamie explains why money can feel invisible to kids today, especially when they mostly see adults using cards, apps, and online shopping instead of cash.

Ashley and Jamie also talk about how advisors can help clients bring money conversations into everyday family life. They discuss why parents often avoid these conversations, how shame or past money mistakes can get in the way, and why stories, vulnerability, and simple tools can make these talks easier.

Episode Highlights:

• How the Milton the Money Savvy Pup series began
• Why kids need direct money lessons, not just observation
• How technology has made money feel less visible to children
• Simple ways to teach earning, saving, spending, and giving
• Why gratitude matters in a child’s money education
• How advisors can help clients talk to their kids about money
• Why parents do not need to have everything figured out before teaching their kids
• How everyday moments, like grocery shopping or saving for a toy, can become money lessons

RESOURCES AND GUEST INFORMATION

Jamie Bossi is a financial planner, author, and mother of four. She helps clients work through life transitions, organize their financial lives, and make decisions that support their goals.

Jamie is passionate about mentoring and financial literacy. She is the author of Money Boss Mom: Helping Young Parents Be the “Boss” of Their Financial Future, the Milton the Money Savvy Pup children’s book series, and Investing for Tweens, a book designed for ages 10 to 14.

Connect with Jamie Bosse:

• Website: https://www.moneybossmom.com/
• Instagram: https://www.instagram.com/moneybossmom/
• LinkedIn: https://www.linkedin.com/in/jamiebosse/

Connect with Host Ashley Quamme:

• Podcast Website: https://www.planningandbeyond.com
• LinkedIn: https://www.linkedin.com/in/ashley-quamme
• Beyond the Plan®: https://www.beyondthefp.com
• Monthly Newsletter: https://www.beyondthefp.com

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What if AI helped advisors become more human, not less?

In this episode of Planning & Beyond®, Ashley talks with Gabe Caldwell, co-founder of Quin, about how technology can help financial advisors get time, energy, and attention back.

Gabe explains that the best use of AI is not simply writing LinkedIn posts or brainstorming ideas. For advisors, the bigger opportunity is using AI to handle the routine work that often eats up the week: meeting prep, notes, follow-up emails, CRM updates, scheduling, and client communication.

Ashley and Gabe discuss the reality that many advisors are spending about 22 hours a week on admin work, and what changes when some of that load comes off their plate. Gabe shares how reducing admin work can help advisors sleep better, feel less rushed, show up with more energy, and be more present in client meetings.

They also talk about the concerns many advisors have around AI, including control, compliance, privacy, and whether technology could weaken the client relationship. Gabe explains why good AI tools should keep the advisor involved, especially when client communication is being drafted or sent.

Episode Highlights:

• How Gabe’s earlier business experiences shaped the creation of Quin
• Why AI should help advisors get time back, not just do more work
• How admin tasks affect advisor presence and client relationships
• Why reducing mental load can improve how advisors show up in meetings
• Common concerns about AI, control, compliance, and client trust
• Why human review still matters when using AI tools
• How advisors can use technology to support the work they actually enjoy

This conversation is especially useful for advisors who want to use AI thoughtfully, reduce routine admin work, and create more space for the human side of financial planning.

RESOURCES AND GUEST INFORMATION

Gabe Caldwell is co-founder of Quin, an AI assistant for financial advisors and other relationship professionals. Quin helps with routine work such as meeting prep, note capture, email drafts, CRM updates, scheduling, and client communication through tools like SMS, email, voice, Slack, and Teams. Advisors using Quin save 5 to 15 hours per week by offloading routine admin work.

Gabe is also a co-founder of Plain Sight Ventures, where he and his team have built and scaled multiple software companies to millions of users over the past 10 years. His work focuses on helping professionals automate the tasks that slow them down so they can spend more time on relationships.

Connect with Gabe Caldwell:

• LinkedIn: https://www.linkedin.com/in/gabecaldwell/
• Website: https://www.heyquin.io/
• Sign up for a 2-week free trial of Quin: https://www.heyquin.io/app/signup

Connect with Host Ashley Quamme:

• Podcast Website: https://www.planningandbeyond.com
• LinkedIn: https://www.linkedin.com/in/ashley-quamme
• Beyond the Plan®: https://www.beyondthefp.com
• Monthly Newsletter: https://www.beyondthefp.com

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Couples fighting about money can derail a meeting fast, but Ashley Quamme shows why the real skill is not choosing sides - it’s knowing how to steer the conversation without losing trust. If you advise couples or families, this episode gives you a practical way to handle tension, interrupt conflict, and keep control of the room. Ashley breaks down the three questions hidden inside every money disagreement: how to stay in charge, how to protect the relationship with both clients, and whether this is even part of your job. She explains why financial advisors should shift from content to process, so instead of getting stuck on the boat, the retirement date, or the credit card bill, you can focus on what’s actually happening between the two people in front of you. You’ll discover:

• How to move a couple from “who’s right” to “what’s going on here”
• Why interrupting can be a strength, not a mistake
• The exact kind of expectation-setting that helps clients handle conflict before it starts
• How to make the covert overt by naming tension in a way that builds trust
• The difference between validating a client and agreeing with them

If you are an advisor and you have a question you'd like Ashley to tackle, feel free to send them to: hello@beyondthefp.com

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Good advisors can still find themselves in difficult ethical situations, especially when they are under pressure, early in their careers, or trying hard to help a client.

In this episode, Ashley talks with Dr. Moira Somers, a clinical consultant and researcher focused on misconduct in financial advising. Together, they look at why misconduct happens, how it can show up in different forms, and why it is not always driven by bad intentions.

Moira shares what her research has shown about the gray areas advisors may face, especially early-career professionals who are still learning how to manage client expectations, firm pressure, professional boundaries, and stress. She also explains how the desire to be helpful can sometimes blur ethical lines, and why advisors need support before small compromises become bigger problems.

Episode Highlights:

• What misconduct means in financial advising
• The different ways misconduct can show up
• Why early-career advisors may be more at risk for ethical mistakes
• How stress and burnout can affect decision-making
• Why professional boundaries matter
• How firm culture can support or weaken ethical behavior
• What advisors and firms can do to create better support systems

This conversation is especially useful for financial advisors who want to do right by their clients, understand the gray areas of ethical decision-making, and stay prepared for the pressure that can come with the work.

RESOURCES AND GUEST INFORMATION

Dr. Moira Somers is a psychologist, consultant and family enterprise advisor. She specializes in the psychology of money and in the many ways it influences people's decision-making, relationships and well-being. Her clients include individuals, family businesses, financial firms and community agencies. In her consulting practice, Dr. Somers trains advisors on matters pertaining to the personal side of money. Her teaching and research interests include broader design and structural issues affecting investing, financial follow-through and equitable access to capital.Although Canada is her home, her client base is international. She is the Chair of the Family Advisor Relationships Domain for the Ultra High Net Worth Institute, and a faculty member at the Financial Transitionist® Institute.

Connect with Dr. Moira Somers:

• Website: https://moneymindandmeaning.com/
• Book (coming ​out ​on ​9/8/2026):The Fault Lines Of Finance: Understanding And Preventing Financial Misconduct

Connect with Host Ashley Quamme:

• Podcast Website: https://www.planningandbeyond.com
• LinkedIn: https://www.linkedin.com/in/ashley-quamme
• Beyond the Plan®: https://www.beyondthefp.com
• Monthly Newsletter: https://www.beyondthefp.com