The Financially Fit Couple

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!

The Financially Fit Couple is a business podcast hosted by Matthew Gray, CFP®, with 28 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Matthew Gray, CFP® hosts The Financially Fit Couple, a business show with 28 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #18

  S2 E18: Getting Your Child CollegeReady with Shellee Howard

  Aug 17, 202647 minS2

  Host Matthew Gray interviews college admissions consultant Shellee Howard of CollegeReady about preparing children for college amid AI-driven change. Howard shares her origin story helping her son earn full-ride offers (USC Presidential Scholarship; Harvard match) and argues AI will shift and expand jobs, making communication, leadership, and strategic thinking essential; she notes computer science is currently the most unemployed major due to AI replacing entry-level roles and advises evaluating whether colleges are truly pivoting (e.g., Vanderbilt using verbal exams). She emphasizes building intellectual curiosity early through reading, hands-on play, and limiting device dependence, and starting service as soon as kids can participate. Howard outlines a timeline: eighth-grade promotion starts the “college clock,” summers are critical for exploration (shadowing, internships, service), and high school course choices are hard to change. She stresses early financial literacy, candid cost conversations, and FAFSA timing, and describes CollegeReady’s student-centric process for clarifying goals, building a standout strategy, selecting balanced school lists, and managing application timelines, plus resources at collegereadyplan.com and her books. 00:38 Meet Shellee Howard 01:46 CollegeReady Origin Story 04:03 College Value in the AI Era 10:17 Choosing AI Ready Colleges 10:51 Curiosity Over Screens 13:31 Is College the Right Path 18:00 Middle School to High School Timeline 24:01 Picking Majors and Schools 30:43 Talking College Costs 36:42 How College Ready Helps 44:19 Resources and Final Advice 46:35 Wrap Up and Disclosures Resources Shellee Howard CollegeReady How to Send Your Student to College Without Losing Your Mind or Your Money book The College Admissions Plan Simplified 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

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  Episode #17

  S2 E17 - Better Money Conversations with BatSheva Goldstein

  Aug 3, 202631 minS2

  Host Matthew Gray interviews Batsheva Goldstein, an Israel-based member of a multigenerational “financial family,” about why couples’ money conversations often break down and how to improve them. They discuss how financial decisions reflect deeper values, identity, and past experiences, illustrated by personal stories about buying a new car and spending on a sports jersey. Goldstein explains that couples must revisit money talks as life changes and that alignment between two people—each with different goals and risk tolerances—should come before technical planning. She introduces Financial Date Discussion Cards, designed to create a structured, phone-free, team-based way to practice neutral, curiosity-driven questions and build communication “reps,” even during disagreements. Listeners can purchase at financialdate.com/financiallyfit and connect with Goldstein on LinkedIn. 00:37 Meet the Guest 02:53 Why Money Talks Matter 04:21 Hidden Subtext and Values 06:34 A Car Story Example 09:16 Starting the Conversation 09:38 Financial Date Cards 15:03 Practice Like the Gym 21:13 Aligning Goals as a Couple 22:48 How to Use the Cards 28:19 Where to Get Them 29:07 Final Thoughts and Wrap Up 30:12 Listener Thanks and Disclosures Resources BatSheva Goldstein Link to purchase Financial Date Discussion Cards - financialdate.com/financiallyfit https://www.linkedin.com/in/batsheva-goldstein/ 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

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  Episode #16

  S2 E16: Accelerate Your Real Estate Investing with Lane Kawaoka

  Jul 20, 202636 minS2

  Host Matthew Gray interviews investor Lane Kawaoka about his path from buying a Seattle home in 2007 to building 11 out-of-state rentals by 2015, and later moving into multifamily value-add syndications and private placements. The conversation highlights why cash flow matters, including using the 1% rent-to-price rule as a quick screen and budgeting for maintenance and CapEx. Lane also addresses his role with property managers in “managing the manager.” Lane breaks down neighborhood classes (A–D), the tradeoffs between better rent ratios and more headaches in lower-class areas, and why many high-priced markets don't work out. He also explains how remote purchases can work through inspections and local property manager input. Lane reviews four return drivers (cash flow, mortgage paydown, appreciation, and tax benefits like depreciation), and clarifies accredited investor status and the opportunities it can open. 00:37 Meet Lane Kawaoka 01:42 First Rentals and Early Wins 04:14 Lessons and Property Managers 06:30 Down Payments and Deal Math 08:29 Neighborhood Classes Explained 10:16 Value Add and Scaling Up 11:57 Buying Out of State 15:22 Cash Flow and Tax Benefits 23:59 Accredited Investor Basics 27:04 Syndications and Wealth Elevator 33:00 Getting Started and Wrap Up Resources Lane Kawaoka TurnKey Resources The Wealth Elevator Book Your First Rental Property Podcast 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

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  Episode #15

  S2 E15: Selling Your Business with Kyle Glenn

  Jul 6, 202641 minS2

  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

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  Episode #14

  S2 E14: Financing Residential Investment Property with Sol Skolnick

  Jun 22, 202638 minS2

  Matthew Gray interviews mortgage banker Saul 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

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