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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
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By Matthew Gray, CFP®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