CFO Unplugged

Crystal Haight

This podcast is from a trained bookkeeper, turned accountant, and then a financial coach. Crystal's experience led her to help business owners live the lifestyle that's been marketed, promoted, and all the sacrifices, but she saw a gap. In all her experiences, she wants to help in the best way she can, and that's by showing her clients how to create positive cash flow across everything the business does.

  1. Oct 2

    Growth After Grief: Learning to Ask for Help | CFO Unplugged Ep. 20

    TRIGGER WARNING: SUICIDE and DEATH discussed. A year after losing his mom, Nathan Webster hit a point so low he almost ended his life. He had spent that year staying strong for everyone else, never stopping to grieve, and telling almost no one what he was carrying. In this episode of CFO Unplugged, Crystal Haight sits down with Nathan to talk about growth, the kind that comes out of your hardest season. They talk about how avoidance and people pleasing kept him from facing his grief, why he only told three people, and what finally helped him climb out of the bottom. If you're the strong one in your family, a recovering people pleaser, or someone carrying grief you haven't faced yet, this one's for you. If you're struggling, you don't have to go through it alone. In the US, call or text 988 to reach the 988 Suicide & Crisis Lifeline, available 24/7. Outside the US, contact your local crisis line or emergency services. Connect with Nathan Webster:  Website: https://ndubbrand.com/ YouTube: https://youtube.com/@nathan.a.webster   Connect with Crystal Haight & NW Book Pros: Website: https://nwbookpros.com/ Book Your Financial Reset: https://nwbookpros.com/service/financial-reset #grief #mentalhealth #peoplepleaser    Subscribe to CFO Unplugged for more honest, no fluff conversations about managing the financial side of your business and your life. This video is for general educational purposes only and isn't a substitute for professional mental health, medical, or crisis support. If you're in crisis, call or text 988 in the US or contact your local emergency services.   Directed and Edited: Nathan A Webster, MBA https://ndubbrand.com/ https://youtube.com/@nathan.a.webster

  2. Sep 24

    From Paralegal to Medicare Broker: Building a Flexible Career | CFO Unplugged Ep. 19

    After 20 years as a senior paralegal and trial expert, Natasha got laid off overnight. She didn't have to scramble, though. She had already been building a Medicare business on the side. In this episode of CFO Unplugged, Crystal Haight sits down with Natasha, an independent Medicare insurance broker, to talk about her path from trial work to vocational rehabilitation to Medicare. They cover why she recommends working as an independent broker instead of a captive agent, who keeps your book of business when you leave, and why getting paid on a 1099 instead of a W2 can decide whether you build real equity or just earn a salary. Natasha also explains why Medicare is a proven business model, since the demand is already there and you're educating people instead of selling to them. Clients pay nothing to work with a broker, commissions are federally regulated, and your book of business builds recurring income year after year. If you're a parent going back to work, someone tired of high pressure sales, or anyone looking for a flexible career you can build at your own pace, this one's for you. Connect with Natasha: Call or text: 941.315.6761   Connect with Crystal Haight & NW Book Pros: Website: https://nwbookpros.com/ Book Your Financial Reset: https://nwbookpros.com/service/financial-reset   #medicare #careerchange #insurancebroker    This video is for general educational purposes only and isn't personalized insurance, tax, legal, career, or financial advice. Talk to a licensed professional about your specific situation.   Directed and Edited: Nathan A Webster, MBA https://ndubbrand.com/ https://youtube.com/@nathan.a.webster

  3. Sep 17

    Medicare Explained: What to Know Before You Turn 65 | CFO Unplugged Ep. 18

    Turning 65 soon? Miss one Medicare deadline and you could be paying a penalty for the rest of your life. In this episode of CFO Unplugged, Crystal Haight sits down with Natasha, an independent insurance broker, to break down Medicare in plain English. They cover when to start signing up, the lifetime penalties for missing your enrollment window, what Parts A, B, and D actually cover, and the difference between Original Medicare, a supplement (Medigap), and a Medicare Advantage plan. Natasha shares why working with an independent broker beats going it alone or using a captive agent, plus the story of a client whose new prescription was going to cost $3,000 a month until a plan switch dropped it to $20. They also get into why business owners should pay attention when an employee turns 65, why Medicare planning should start two years before your 65th birthday (your premiums look back at your income), and how supplemental policies like hospital indemnity and critical illness coverage fill the gaps no plan covers. If you're approaching 65, helping a parent sort through Medicare, or running a business with employees nearing retirement, this one's for you. How to reach Natasha Connect with Natasha: Call or text: 941.315.6761 Connect with Crystal Haight & NW Book Pros: Website: https://nwbookpros.com/ Book Your Financial Reset: https://nwbookpros.com/service/financial-reset #medicare #retirementplanning #turning65 Subscribe to CFO Unplugged for more honest, no fluff conversations about managing the financial side of your business and your life.   This video is for general educational purposes only and isn't personalized insurance, tax, legal, or financial advice. Talk to a licensed professional about your specific situation.   Directed and Edited: Nathan A Webster, MBA https://ndubbrand.com/ https://youtube.com/@nathan.a.webster

  4. Sep 10 ·  Video

    Will AI Replace Finance Jobs? A Wealth Manager's Honest Answer | CFO Unplugged Ep. 17

    Are finance and accounting jobs going to be replaced by AI? In this episode of CFO Unplugged, Crystal Haight sits down with wealth manager and MBA instructor Chris to talk about what AI is actually changing in wealth management, accounting, and bookkeeping, and what it isn't. Chris shares how a client report that used to take his team eight hours now takes 45 minutes, why bank tellers and secretaries didn't disappear when ATMs and word processors showed up, and the story of a former student who called to say he'd been replaced by AI. Spoiler: he wasn't replaced by AI. He was replaced because he never owned it. We also get into AI slop, why you still have to understand the math behind the numbers, the case for mastering two unrelated disciplines, using AI as a thought partner instead of a yes man, and why friction and creating things (not just consuming) are what actually make work and life satisfying. If you're a bookkeeper, analyst, accountant, wealth manager, or a student trying to figure out where you fit in a world with AI, this one's for you. More on Chris Magaña: - https://chrismagana.com - https://imscapital.com/about-us/chris-magana/   Directed and Edited: Nathan A Webster, MBA  https://ndubbrand.com/ https://youtube.com/@nathan.a.webster?si=Z01ZIAXf7fbXLAFT

  5. Sep 4 ·  Video

    The Joy of Now | CFO Unplugged Ep. 16

    What's the point of building wealth if you never actually enjoy it? In this episode of CFO Unplugged, Crystal sits down with Chris Magaña, wealth manager and adjunct professor at Willamette University's Atkinson Graduate School of Management, to talk about his chapter in the new book "Even More Than Money," fittingly titled "The Joy of Now." Chris has spent his career managing wealth for high-net-worth families, and today more than half of his clients are nonprofit organizations. He opens up about why he chose that path, his own complicated relationship with money after losing his father, and the philosophy that drives his work: give sooner, not later. We get into: - Why so many successful people never stop to ask "what's the point of making more money?" - The real cost of waiting until you "tip over" to give your wealth away - Why the quietest givers are often the most generous ones - A client story about legacy giving that will stick with you - Why visible, community-driven giving creates a snowball effect Chris's chapter, "The Joy of Now," appears in Even More Than Money: Five Ways To Design Your Financial Life by Justin Castelli, Shanna Due, and Taylor Schulte, 20 real stories from financial advisors, with 100% of proceeds going to charity. His chapter starts on page 127. 📖 Get the book on Amazon: https://www.amazon.com/Even-More-Than-Money-Financial/dp/1804091243 (Also available at Barnes & Noble, Target, Walmart, and Google Books.) More on Chris Magaña: - https://chrismagana.com - https://imscapital.com/about-us/chris-magana/   Directed and Edited: Nathan A Webster, MBA  https://ndubbrand.com/ https://youtube.com/@nathan.a.webster?si=Z01ZIAXf7fbXLAFT

  6. Aug 28 ·  Video

    Payroll Failures: Lessons from a Costly Mistake | CFO Unplugged Ep 15

    Payroll mistakes can quietly drain your business, and most owners don't catch them until they've already cost thousands. In this episode of CFO Unplugged, Crystal sits down with Trey to break down a real, costly payroll failure and the lessons every small business owner needs to take from it. They cover why payroll mistakes happen in the first place, the most common errors that create discrepancies in your accounts, and the lasting financial impact they have on your bottom line, compliance, and cash flow. If you run payroll for your business (or are about to start), this conversation will help you audit your current systems, catch mistakes early, and avoid the costly tax filing and compliance headaches that come with them. Subscribe to CFO Unplugged for more honest, no-fluff conversations about running the financial side of your business. This video is for general educational purposes only and isn't personalized tax, legal, or financial advice. Talk to your own CPA, attorney, or advisor about your specific situation.   Connect with Crystal Haight & NW Book Pros:  Website: https://nwbookpros.com/ Book Your Financial Reset: https://nwbookpros.com/service/financial-reset

  7. Aug 21 ·  Video

    The True Cost of Hiring an Employee | CFO Unplugged Ep 14

    Ever wonder what it really costs to hire your first employee? Spoiler: it's a lot more than their salary. In this episode of CFO Unplugged, Crystal sits down with Trey to break down everything business owners get wrong about the true cost of hiring from payroll taxes and workers' compensation to the real difference between a W-2 employee and a 1099 contractor, how to recruit smart as a small business, and how to prioritize benefits like retirement plans vs. health insurance. If you're a small business owner (or about to become one) trying to decide whether to hire your first employee, this conversation will save you from some very expensive mistakes. Subscribe to CFO Unplugged for more honest, no-fluff conversations about running the financial side of your business. This video is for general educational purposes only and isn't personalized tax, legal, or financial advice. Talk to your own CPA, attorney, or advisor about your specific situation. Connect with Crystal Haight & NW Book Pros: Website: https://nwbookpros.com/ Book Your Financial Reset: https://nwbookpros.com/service/financial-reset  Watch full YouTube video here: https://youtu.be/2rKPRR-7MW8

  8. Aug 14 ·  Video

    Confessions of 3 Recovering People Pleasers | CFO Unplugged Ep. 13

    Saying yes when you mean no doesn't make you generous— it makes you exhausted. In this episode of CFO Unplugged, Crystal Haight is joined by returning guest Nathan Webster (fractional CMO) and first-time guest Nick Hazard, a residential and commercial contractor, for an unscripted roundtable on people-pleasing. All three admit they're recovering people-pleasers, and they trace it back to where it actually started: chaos and conflict growing up, constantly moving schools, getting picked on as a kid.  From there, the conversation covers why people pleasers over-explain and justify every "no," how boundaries get blurry with kids and with clients who only take and never give, and why perfectionism and "fake it till you make it" quietly wreck your growth. Crystal shares the property management story that taught her to trust her team rather than manage everyone, and Nick makes the case for collaboration over competition in an industry built on scarcity thinking. Midway through, they turn the question over to AI for its take on breaking the people-pleasing cycle and walk through six practical tips: 1) pause before answering 2) separate the request from the relationship 3) know the real cost of saying yes 4) practice small no's first 5) expect the guilt 6) get comfortable disappointing people. If you've ever said yes and regretted it before you even hung up the phone, this episode is for you. Connect with Crystal Haight & NW Book Pros: Website: https://nwbookpros.com/ Book Your Financial Reset: https://nwbookpros.com/service/financial-reset   Directed and Edited: Nathan A Webster, MBA https://ndubbrand.com/    Watch full YouTube video: https://youtu.be/CnwcJngVHpQ

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About

This podcast is from a trained bookkeeper, turned accountant, and then a financial coach. Crystal's experience led her to help business owners live the lifestyle that's been marketed, promoted, and all the sacrifices, but she saw a gap. In all her experiences, she wants to help in the best way she can, and that's by showing her clients how to create positive cash flow across everything the business does.

Information

  • Creator
    Crystal Haight
  • Years Active
    2026
  • Episodes
    20
  • Rating
    Explicit
  • Copyright
    © 2026
  • Show Website
    CFO Unplugged