The Financially Fit Couple

Matthew Gray, CFP®

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Hey there, and welcome to the Financially Fit Couple! This podcast is all about answering the questions busy, married couples find themselves asking about their finances. I’m Matthew Gray, your host and a Certified Financial Planner. Join me as I interview topic experts and other couples just like you to find out how to pursue your goals and live financially healthy lives. Let’s get started!

2d ago

S2 E15: Selling Your Business with Kyle Glenn

Matthew Gray hosts The Financially Fit Couple and interviews Kyle Glenn, a CERTIFIED FINANCIAL PLANNER and Certified Exit Planning Advisor, about selling a business as part of retirement planning. Glenn explains common triggers for selling—retirement, margin pressure from inflation, employee turnover, and burnout. He also notes research showing roughly 80% of listed businesses don’t sell, making exits less likely to succeed than surviving a startup’s first decade. They discuss what makes an exit “successful,” emphasizing liquidity outside the business and readiness for life after ownership. Key obstacles include overestimating value, poor financial records, key-person dependency, and psychological hesitation that can derail deals. Glenn outlines finding buyers via networks or M&A advisors, using teasers and NDAs, and preparing 3–5 years in advance. He also reviews asset vs. stock sale tax implications, allocation to goodwill, QSBS, and charitable strategies. Kyle recommends every business owner build a core team of CPA, exit planner, and financial planner plus resources like the Exit Planning Institute’s State of Owner Readiness survey. 00:37 Meet Kyle Glenn 03:12 Why Owners Sell 07:30 What Makes an Exit Work 12:05 Top Sale Obstacles 16:28 Mindset and Motivation 21:54 Finding the Right Buyer 26:08 Taxes and Deal Structure 32:22 Build Your Exit Team 36:39 Resources and Wrap Up Resources Kyle Glenn Kyle's bio Kyle's LinkedIn Exit Planning Institute's Research on Owner Readiness Glenn Financial is not affiliated with Schrock Financial or LPL Financial. Neither LPL Financial nor it's affiliated advisors provide business valuations or any activity that matches buyers and sellers. Schrock Financial and LPL Financial do not provide legal advice or tax services. Please consult your legal advisor or tax advisor regarding your specific situation. Matthew Gray https://www.linkedin.com/in/matthew-gray-cfp%C2%AE-5a2144134/ https://schrockfin.com/ Securities and advisory services offered through LPL Financial, a registered investment advisor, Member FINRA/SIPC

41 min
Jun 22

S2 E14: Financing Residential Investment Property with Sol Skolnick

Matthew Gray interviews mortgage banker Sol Skolnik (“Professor Home Loan”) about financing residential investment properties. Skolnik explains his background entering lending in 2006 and why sustainable loan fit matters after seeing risky pre-crash products. They cover who should consider rentals, including portfolio diversification, landlord responsibilities, and using managing agents. Skolnik outlines key financing options, evaluating areas and rental markets, using inspections, lender qualification factors, and pre-approvals vs TBD commitment letters. Sol also goes through the differences between brokers, mortgage banks, and depository banks. Stay tuned to the end to learn how to contact Skolnik for a free book and lending coverage. 00:37 Meet Professor Home Loan 01:36 Saul’s Mortgage Journey 04:08 Why Sustainability Matters 06:31 Should You Buy Rentals? 08:23 Financing Options Overview 13:33 Rates Terms and Down Payments 15:21 Picking Markets and Pros 17:14 Inspections and Risk Checks 18:34 What Lenders Evaluate 20:33 Picking the Right Market 21:26 Financing and Preapproval Limits 23:25 TBD Commitment Letters 26:02 Choosing Lenders and Brokers 32:18 Refinancing and Doing the Math 33:41 Landlord Responsibilities Reality 37:01 Wrap Up and Disclosures Resources Sol Skolnick 914-380-0600 sskolnick@unitedmortgage.com https://solskolnick2.book.live/mortgage-lenders-buyers-book Matthew Gray https://www.linkedin.com/in/matthew-gray-cfp%C2%AE-5a2144134/ https://schrockfin.com/ Securities and advisory services offered through LPL Financial, a registered investment advisor, Member FINRA/SIPC

38 min
Jun 8

S2 E13: Building a Business Beyond Yourself with Brad Cohen

Matthew Gray interviews Harrisonburg/Shenandoah Valley REALTOR® Brad Cohen about moving from solo agent to building Connexa, a boutique brokerage. Brad shares his early start in real estate as a college student, selling 27 homes his first year by networking, taking undesirable leads, and learning business-building skills not taught in licensing. Brad explains the necessity and vision behind starting Connexa. He highlights the grind of the first year, leaving significant income, hiring his first full-time employee, adding agents, and buying an office in 2024. He discusses unexpected management demands, mentorship, turnover, and balancing marriage with business ownership. Stay tuned at the end for his brief thoughts on the value of a college education based on his life experience! 00:38 Meet Brad Cohen 01:38 Brad’s Origin Story 03:16 First-Year Breakthrough 06:41 Brokerages and Models 12:01 Why Build a Team 17:45 Crunching the Numbers 20:45 Scrappy Startup Year One 24:49 Expected vs Unexpected 27:15 Learning to Lead People 30:55 Marriage Amid the Grind 32:25 Work Life Counterbalance 35:18 Team Turnover and Rebuild 36:56 Boutique Vision and Equity 40:39 Survive to Thrive Stage 41:47 Advice for New Owners 45:21 Is College Necessary? 48:17 Hiring for Grit and Network 49:15 Where to Connect and Wrap Resources Brad Cohen https://connexare.com/agents/brad-cohen Matthew Gray https://www.linkedin.com/in/matthew-gray-cfp%C2%AE-5a2144134/ https://schrockfin.com/ Securities and advisory services offered through LPL Financial, a registered investment advisor, Member FINRA/SIPC

51 min
May 25

S2 E12: Biblically-Based Investing with Josh Hanna

Matthew Gray interviews Josh Hanna, of Inspire Investing, about faith-based, biblically responsible investing. Josh explains his shift from broad index funds after discovering exposure to abortion and pornography, and describes stewardship as owning part of a business and profiting from its activities. Inspire uses a proprietary Inspire Impact Score with eight negative screens—abortion, pornography, exploitation, LGBT activism, cannabis, alcohol, tobacco, and gambling—with a no-tolerance exclusion approach, plus a positive scoring system that rewards best-in-class ethical practices. He also details corporate engagement via proxy voting and advocacy, citing Costco’s decision not to stock mifepristone after extended engagement. 00:38 Meet Josh and Inspire 04:28 Stewardship and Ownership 05:42 Biblical Screens vs ESG 10:05 Inspire Three Part Approach 12:02 Embrace Good and Engage 16:13 Impact Score and Exclusions 17:42 Consumer vs Investor Choices 20:27 Building Diversified ETFs 22:58 Common Objections Answered 27:12 Returns and Real Impact 30:11 How to Learn More Resources Josh Hanna and Inspire ETFs InspireInsight.com InspireETF.com Matthew Gray https://www.linkedin.com/in/matthew-gray-cfp%C2%AE-5a2144134/ https://schrockfin.com/ Securities and advisory services offered through LPL Financial, a registered investment advisor, Member FINRA/SIPC

34 min
May 11

S2 E11: Teaching Your Kids About Money with Rebecca Irey

Matthew Gray interviews Rebecca Irey, founder and CEO of Blue Sky Financial and a mother of seven, about raising financially independent kids through practical, hands-on experiences. Rebecca shares early lessons like having her daughter earn money for a “My Size Barbie,” using savings interest as incentive, and teaching budgeting by assigning kids responsibility for planning and buying groceries to cook for the family. They discuss why many adults lack basic financial skills due to limited schooling and busy households. Rebecca emphasizes making money tangible with envelope systems and teaching “money is a game,” including playing Robert Kiyosaki’s Cashflow game. Rebecca stresses high expectations, letting kids try and fail at home to build resilience, and listening to teens’ perspectives. She also notes kids may still form different economic views as adults. 00:38 Meet Rebecca Irey 01:48 First Business at 12 04:09 Early Finance Career 05:18 My Size Barbie Lesson 08:55 Why Kids Miss Money Skills 11:55 Practical Money Training 15:15 Cashflow Game Mindset 17:29 Raising Capable Adults 24:22 Let Kids Fail Safely 26:43 Building Resilience Mindset 30:40 Generations And Money Beliefs 32:42 When Kids Reject Your Values 41:00 First Steps And Resources 43:04 Seeing Through Their Eyes Resources Cash Flow Game The Coddling of the American Mind Antifragile The Anxious Generation Socratic Circles Rebecca Irey https://blueskyefinancial.com/ LPL Financial and Blue Skye Financial are separate entities. Matthew Gray https://www.linkedin.com/in/matthew-gray-cfp%C2%AE-5a2144134/ https://schrockfin.com/ Securities and advisory services offered through LPL Financial, a registered investment advisor, Member FINRA/SIPC

48 min
Apr 28

S2 E10: Money Matters in Marriage with Carine & Joe Keenan

Host Matthew Gray welcomes Carine Keenan, a marriage and family therapist, and Joe Keenan, a CFP and CPA, to discuss why money commonly fuels conflict in busy marriages and how couples can turn disagreements into growth. They explain that money issues often connect to safety and security, with saver–spender differences frequently rooted in childhood “money classroom” experiences and personal values like status or future security. Communication breaks down through avoidance, poor timing, and stress (HALTS: hungry, angry, lonely, tired, stressed), which amplifies anxiety. Tools include building self-awareness, using I-statements, scheduling regular “money talks,” creating a fun routine, and using timeouts with a commitment to resume within a day. They distinguish coaching (forward-focused planning and mindset) from therapy (healing deeper, compulsive or impairing behaviors) and describe their Keenan Financial Coaching work with couples across life transitions. 00:37 Meet the Guests 04:46 Why Money Peace Matters 07:00 Why Couples Fight About Money 08:38 Savers vs Spenders Explained 10:56 Why Communication Breaks Down 14:24 Avoidance and Better Timing 16:44 Owning Your Money Fears 20:22 Early Money Classroom Exercise 22:45 Retail Therapy and Awareness Hacks 24:16 Money Talks and Timeouts 32:17 Make Meetings Fun 33:47 Agenda And Prep System 36:10 Keep Growing Together 40:00 When To Get Help 42:55 Coaching Vs Counseling 46:30 Who Their Coaching Serves 50:05 Final Takeaways And Wrap Resources Carine & Joe Keenan https://keenanfinancialcoaching.com/ Matthew Gray https://www.linkedin.com/in/matthew-gray-cfp%C2%AE-5a2144134/ https://schrockfin.com/ Securities and advisory services offered through LPL Financial, a registered investment advisor, Member FINRA/SIPC

54 min
Apr 13

S2 E9: Money Talk for Couples with Sarah Carr

Matthew Gray hosts an episode of the Financially Fit Couple with guest Sarah Carr, a CFP® and certified financial therapist, to discuss how couples communicate about money. Sarah explains financial therapy as the convergence of financial planning and mental health, clarifying she is not a licensed mental health clinician and does not diagnose or create treatment plans, but helps identify emotional barriers that block follow-through on financial plans. They explore why money is a top source of conflict, how it can represent many different piece of our identity, and how subconscious “money scripts” formed in childhood shape behavior. The discussion emphasizes shared goals, curiosity, and creating emotional safety, using values-based planning to align spending with what matters. Also covered in the conversation are regular money check-ins, worksheets, and the Financial Therapy Association directory to find help. 00:38 Meet Sarah Carr 02:33 What Is Financial Therapy 05:18 Emotions Block Action 07:16 Why Money Talks Are Hard 09:26 Money Scripts And Origins 13:23 Healthy Couple Communication 26:48 Finding Your Values 27:48 Reconciling Different Values 30:16 Curiosity Over Conflict 33:28 Creating Safety in Money Talks 36:03 Internal Scripts and Trauma 45:58 Practical Tools and Money Check Ins 49:44 When to Seek Financial Therapy Resources Sarah Carr Money Histories Worksheet (file:///S:/Shared%20Files/Podcast/Sarah%20Carr/Money%20Histories%20Sarah%20Carr%20Financial.pdf) https://sarahcarrfinancial.com/ Matthew Gray https://www.linkedin.com/in/matthew-gray-cfp%C2%AE-5a2144134/ https://schrockfin.com/ Securities and advisory services offered through LPL Financial, a registered investment advisor, Member FINRA/SIPC

54 min
Mar 30

S2 E8: Selling Your Home with Rick Williams

Matthew Gray hosts and welcomes repeat guest Rick Williams, a licensed Virginia realtor with Kline May Realty, to explain the home-selling process. Rick emphasizes that selling is more than listing and waiting, and outlines common seller mistakes such as doing major renovations without advice, waiting for “perfect timing,” and leaning on friends instead of professionals. He describes how he prices homes using comparative market analysis with AI tools plus manual MLS review and broker input, and why pricing too high or too low can deter buyers. They discuss preparing a home, listing steps, evaluating offers beyond price, and how AI helps communications and marketing. They also touch on how AI can’t replace local expertise, judgment, or negotiation. 00:38 Meet Rick Williams 03:07 Why Selling Is Complex 05:22 Common Seller Mistakes 10:32 Goals and Strategy Fit 13:32 How to Price Right 18:11 Prep and Repairs 23:52 Listing and Marketing Plan 27:09 Evaluating Offers 30:01 Contingencies Explained 35:31 From Contract to Closing 38:45 AI Tools and Pitfalls 43:23 Final Advice and Wrap Up Resources Rick Williams http://realestatewithrick.net/ Rick.Williams@KlineMay.com 540-416-1040 Matthew Gray https://www.linkedin.com/in/matthew-gray-cfp%C2%AE-5a2144134/ https://schrockfin.com/ Securities and advisory services offered through LPL Financial, a registered investment advisor, Member FINRA/SIPC

46 min

Hey there, and welcome to the Financially Fit Couple! This podcast is all about answering the questions busy, married couples find themselves asking about their finances. I’m Matthew Gray, your host and a Certified Financial Planner. Join me as I interview topic experts and other couples just like you to find out how to pursue your goals and live financially healthy lives. Let’s get started!

Creator

Matthew Gray, CFP®
Years Active

2025 - 2026
Episodes

26
Rating

Clean
Copyright

© 2026 The Financially Fit Couple
Show Website

The Financially Fit Couple