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.
Growth After Grief: Learning to Ask for Help | CFO Unplugged Ep. 20
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
24 Sept 2026
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
17 Sept 2026
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
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