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Apr 16, 2021 · 32m · we-live-to-build

The Audit That Saved Me Hundreds of Thousands When I Sold

Jay Myers · 22m spoken Sean Weisbrot · 7m spoken
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In this episode of the We Live to Build podcast, founder Jay Myers outlines actionable strategies for scaling and selling a business, including operational due diligence, tax optimization via personal goodwill, and managing the psychological void that follows an exit.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Sean holds 26.7% of the talking time here. How this is scored →

Sean as informed peer 2.8 Guest teaching 4.0 Guest disagreement 0.2 Sean pushing back 0.2
05100:0010:0020:0030:002:12–6:14 · Sean as informed peer 2/10 Jay Myers on Founding and Scaling Interactive Solutions Sean asks Jay when he first considered selling his business. Jay gently pushes back on the idea that founders ignore acquisition inquiries without being flattered, walking through his 20-year journey.6:14–9:22 · Sean as informed peer 3/10 Preparing Operational Value and Financial Cleanliness for Acquisition Sean inquires about operational improvements to drive valuation. Jay details critical M&A factors like audited financials, customer diversification, and recurring revenue.9:22–11:37 · Sean as informed peer 2/10 Cultivating Company Reputation and Retaining Talent Through Empathy Sean asks how to evaluate reputation and curb employee turnover. Jay explains his philosophy of compassionate management, sharing how he supported employees facing severe health crises.11:37–13:51 · Sean as informed peer 2/10 Leveraging Growth Rankings and Managing Application Timelines Sean asks practical questions about getting featured on Inc. and Forbes fastest-growing lists. Jay breaks down the five-year growth application rules and timeline mechanics.13:51–16:23 · Sean as informed peer 5/10 The Psychological Toll and Identity Loss Following an Exit Jay reflects on the emotional unpreparedness founders face after selling. Sean connects this to insights from a previous wealth management episode regarding post-exit loss of purpose.16:23–20:09 · Sean as informed peer 4/10 Navigating the Grieving Process and Planning Life After the Sale Jay describes mentoring and authoring books as preparation for life after exit. Sean suggests that planning too far ahead is somewhat futile due to constant entrepreneurial evolution.20:09–25:07 · Sean as informed peer 2/10 Strategic Buyer Outreach and Son's Due Diligence at Infocomm Jay recounts sending his son to Infocomm to vet the acquirer and using his son's due diligence role as a cover story to keep the sale confidential from staff.25:10–28:39 · Sean as informed peer 3/10 Negotiating Purchase Price and Securing Life-Changing Capital Sean asks about tax strategies during acquisition. Jay delivers an informative breakdown of personal goodwill audits and how separating personal goodwill saved hundreds of thousands in taxes.28:39–31:02 · Sean as informed peer 2/10 Post-Exit Philanthropy, Startup Mentorship, and Angel Investing Sean asks about future plans and unaddressed advice. Jay shares his work with SCORE and highlights that companies sell when the business is ready, not when the founder is ready.2:12–6:14 · Guest teaching 3/10 Jay Myers on Founding and Scaling Interactive Solutions Sean asks Jay when he first considered selling his business. Jay gently pushes back on the idea that founders ignore acquisition inquiries without being flattered, walking through his 20-year journey.6:14–9:22 · Guest teaching 5/10 Preparing Operational Value and Financial Cleanliness for Acquisition Sean inquires about operational improvements to drive valuation. Jay details critical M&A factors like audited financials, customer diversification, and recurring revenue.9:22–11:37 · Guest teaching 3/10 Cultivating Company Reputation and Retaining Talent Through Empathy Sean asks how to evaluate reputation and curb employee turnover. Jay explains his philosophy of compassionate management, sharing how he supported employees facing severe health crises.11:37–13:51 · Guest teaching 4/10 Leveraging Growth Rankings and Managing Application Timelines Sean asks practical questions about getting featured on Inc. and Forbes fastest-growing lists. Jay breaks down the five-year growth application rules and timeline mechanics.13:51–16:23 · Guest teaching 3/10 The Psychological Toll and Identity Loss Following an Exit Jay reflects on the emotional unpreparedness founders face after selling. Sean connects this to insights from a previous wealth management episode regarding post-exit loss of purpose.16:23–20:09 · Guest teaching 3/10 Navigating the Grieving Process and Planning Life After the Sale Jay describes mentoring and authoring books as preparation for life after exit. Sean suggests that planning too far ahead is somewhat futile due to constant entrepreneurial evolution.20:09–25:07 · Guest teaching 5/10 Strategic Buyer Outreach and Son's Due Diligence at Infocomm Jay recounts sending his son to Infocomm to vet the acquirer and using his son's due diligence role as a cover story to keep the sale confidential from staff.25:10–28:39 · Guest teaching 6/10 Negotiating Purchase Price and Securing Life-Changing Capital Sean asks about tax strategies during acquisition. Jay delivers an informative breakdown of personal goodwill audits and how separating personal goodwill saved hundreds of thousands in taxes.28:39–31:02 · Guest teaching 4/10 Post-Exit Philanthropy, Startup Mentorship, and Angel Investing Sean asks about future plans and unaddressed advice. Jay shares his work with SCORE and highlights that companies sell when the business is ready, not when the founder is ready.2:12–6:14 · Guest disagreement 2/10 Jay Myers on Founding and Scaling Interactive Solutions Sean asks Jay when he first considered selling his business. Jay gently pushes back on the idea that founders ignore acquisition inquiries without being flattered, walking through his 20-year journey.6:14–9:22 · Guest disagreement 0/10 Preparing Operational Value and Financial Cleanliness for Acquisition Sean inquires about operational improvements to drive valuation. Jay details critical M&A factors like audited financials, customer diversification, and recurring revenue.9:22–11:37 · Guest disagreement 0/10 Cultivating Company Reputation and Retaining Talent Through Empathy Sean asks how to evaluate reputation and curb employee turnover. Jay explains his philosophy of compassionate management, sharing how he supported employees facing severe health crises.11:37–13:51 · Guest disagreement 0/10 Leveraging Growth Rankings and Managing Application Timelines Sean asks practical questions about getting featured on Inc. and Forbes fastest-growing lists. Jay breaks down the five-year growth application rules and timeline mechanics.13:51–16:23 · Guest disagreement 0/10 The Psychological Toll and Identity Loss Following an Exit Jay reflects on the emotional unpreparedness founders face after selling. Sean connects this to insights from a previous wealth management episode regarding post-exit loss of purpose.16:23–20:09 · Guest disagreement 0/10 Navigating the Grieving Process and Planning Life After the Sale Jay describes mentoring and authoring books as preparation for life after exit. Sean suggests that planning too far ahead is somewhat futile due to constant entrepreneurial evolution.20:09–25:07 · Guest disagreement 0/10 Strategic Buyer Outreach and Son's Due Diligence at Infocomm Jay recounts sending his son to Infocomm to vet the acquirer and using his son's due diligence role as a cover story to keep the sale confidential from staff.25:10–28:39 · Guest disagreement 0/10 Negotiating Purchase Price and Securing Life-Changing Capital Sean asks about tax strategies during acquisition. Jay delivers an informative breakdown of personal goodwill audits and how separating personal goodwill saved hundreds of thousands in taxes.28:39–31:02 · Guest disagreement 0/10 Post-Exit Philanthropy, Startup Mentorship, and Angel Investing Sean asks about future plans and unaddressed advice. Jay shares his work with SCORE and highlights that companies sell when the business is ready, not when the founder is ready.2:12–6:14 · Sean pushing back 0/10 Jay Myers on Founding and Scaling Interactive Solutions Sean asks Jay when he first considered selling his business. Jay gently pushes back on the idea that founders ignore acquisition inquiries without being flattered, walking through his 20-year journey.6:14–9:22 · Sean pushing back 0/10 Preparing Operational Value and Financial Cleanliness for Acquisition Sean inquires about operational improvements to drive valuation. Jay details critical M&A factors like audited financials, customer diversification, and recurring revenue.9:22–11:37 · Sean pushing back 0/10 Cultivating Company Reputation and Retaining Talent Through Empathy Sean asks how to evaluate reputation and curb employee turnover. Jay explains his philosophy of compassionate management, sharing how he supported employees facing severe health crises.11:37–13:51 · Sean pushing back 0/10 Leveraging Growth Rankings and Managing Application Timelines Sean asks practical questions about getting featured on Inc. and Forbes fastest-growing lists. Jay breaks down the five-year growth application rules and timeline mechanics.13:51–16:23 · Sean pushing back 0/10 The Psychological Toll and Identity Loss Following an Exit Jay reflects on the emotional unpreparedness founders face after selling. Sean connects this to insights from a previous wealth management episode regarding post-exit loss of purpose.16:23–20:09 · Sean pushing back 2/10 Navigating the Grieving Process and Planning Life After the Sale Jay describes mentoring and authoring books as preparation for life after exit. Sean suggests that planning too far ahead is somewhat futile due to constant entrepreneurial evolution.20:09–25:07 · Sean pushing back 0/10 Strategic Buyer Outreach and Son's Due Diligence at Infocomm Jay recounts sending his son to Infocomm to vet the acquirer and using his son's due diligence role as a cover story to keep the sale confidential from staff.25:10–28:39 · Sean pushing back 0/10 Negotiating Purchase Price and Securing Life-Changing Capital Sean asks about tax strategies during acquisition. Jay delivers an informative breakdown of personal goodwill audits and how separating personal goodwill saved hundreds of thousands in taxes.28:39–31:02 · Sean pushing back 0/10 Post-Exit Philanthropy, Startup Mentorship, and Angel Investing Sean asks about future plans and unaddressed advice. Jay shares his work with SCORE and highlights that companies sell when the business is ready, not when the founder is ready.

speaking balance: gold is Sean, purple is the guest (3 minute bins)

0:00 · Sean 89.4% · guest 10.6%0:00 · Sean 89.4% · guest 10.6%3:00 · Sean 13.4% · guest 86.6%3:00 · Sean 13.4% · guest 86.6%6:00 · Sean 14.4% · guest 85.6%6:00 · Sean 14.4% · guest 85.6%9:00 · Sean 21.9% · guest 78.1%9:00 · Sean 21.9% · guest 78.1%12:00 · Sean 11.8% · guest 88.2%12:00 · Sean 11.8% · guest 88.2%15:00 · Sean 38.9% · guest 61.1%15:00 · Sean 38.9% · guest 61.1%18:00 · Sean 29.3% · guest 70.7%18:00 · Sean 29.3% · guest 70.7%21:00 · Sean 8.5% · guest 91.5%21:00 · Sean 8.5% · guest 91.5%24:00 · Sean 26.7% · guest 73.3%24:00 · Sean 26.7% · guest 73.3%27:00 · Sean 12.7% · guest 87.3%27:00 · Sean 12.7% · guest 87.3%30:00 · Sean 26.8% · guest 73.2%30:00 · Sean 26.8% · guest 73.2%
Sharpest disagreement ▶ 4:57 Jay rejects the idea that founders ignore buyout inquiries easily

Jay dismisses the common claim by founders that unsolicited acquisition inquiries are effortlessly ignored, calling it unrealistic and admitting everyone feels flattered.

 Hardest push from Sean ▶ 18:25 Sean challenges long-term post-sale mental preparation

Sean counters the idea that one can fully prepare for life after an exit, arguing that rapid founder evolution renders multi-year post-sale projections mostly futile.

 Biggest teaching moment ▶ 27:02 Jay breaks down the personal goodwill audit tax strategy

Jay educates the host and listeners on the mechanics of personal goodwill appraisals, explaining how quantifying individual founder contribution saved hundreds of thousands in taxes.

 Sean holds their own ▶ 15:13 Sean contextualizes post-exit identity loss using CFP insights

Sean demonstrates his own subject knowledge by citing previous expert interviews regarding founder liquidity events and the psychological vacuum following the loss of a venture.
the scores for every segment, with the reasoning behind each
ChapterTopicSean as informed peerGuest teachingGuest disagreementSean pushing backWhy
Jay Myers on Founding and Scaling Interactive Solutions 2320 Sean asks Jay when he first considered selling his business. Jay gently pushes back on the idea that founders ignore acquisition inquiries without being flattered, walking through his 20-year journey.
Preparing Operational Value and Financial Cleanliness for Acquisition 3500 Sean inquires about operational improvements to drive valuation. Jay details critical M&A factors like audited financials, customer diversification, and recurring revenue.
Cultivating Company Reputation and Retaining Talent Through Empathy 2300 Sean asks how to evaluate reputation and curb employee turnover. Jay explains his philosophy of compassionate management, sharing how he supported employees facing severe health crises.
Leveraging Growth Rankings and Managing Application Timelines 2400 Sean asks practical questions about getting featured on Inc. and Forbes fastest-growing lists. Jay breaks down the five-year growth application rules and timeline mechanics.
The Psychological Toll and Identity Loss Following an Exit 5300 Jay reflects on the emotional unpreparedness founders face after selling. Sean connects this to insights from a previous wealth management episode regarding post-exit loss of purpose.
Navigating the Grieving Process and Planning Life After the Sale 4302 Jay describes mentoring and authoring books as preparation for life after exit. Sean suggests that planning too far ahead is somewhat futile due to constant entrepreneurial evolution.
Strategic Buyer Outreach and Son's Due Diligence at Infocomm 2500 Jay recounts sending his son to Infocomm to vet the acquirer and using his son's due diligence role as a cover story to keep the sale confidential from staff.
Negotiating Purchase Price and Securing Life-Changing Capital 3600 Sean asks about tax strategies during acquisition. Jay delivers an informative breakdown of personal goodwill audits and how separating personal goodwill saved hundreds of thousands in taxes.
Post-Exit Philanthropy, Startup Mentorship, and Angel Investing 2400 Sean asks about future plans and unaddressed advice. Jay shares his work with SCORE and highlights that companies sell when the business is ready, not when the founder is ready.

Statements from this episode (7)

Assertion Supported
Myers: Interactive Solutions reached $25M in sales around 2011
“I guess it was a, 2011, we went from whatever those millions of dollars to twenty-five million in sales, and then we really started getting the calls, and I still blew them off.”
Jay Myers Apr 16, 2021 ▶ 5:29
Disclosure
Myers: Audited financials shrunk Interactive Solutions' sale process to five months
“In our case, we did that, and what could have been a 12 or 18 month process was shrunk down to whatever, four or five months.”
Jay Myers Apr 16, 2021 ▶ 9:15
Disclosure
Jay Myers: Interactive Solutions grew roughly 1,500% over five years
“I think we grew like 1500 and something percent in a five year period of time”
Jay Myers Apr 16, 2021 ▶ 12:27
Insight
Myers: Founders Face a Difficult Grieving Process After Selling
“You know what, Sean, there's a grieving process, and I don't care who out there, if you care about your business, and it's your baby, boy, it's tough, but you know, you gotta figure out a way to deal with it.”
Jay Myers Apr 16, 2021 ▶ 19:55
Disclosure
Myers: Interactive Solutions acquirer made initial offer without price guidance
“In terms of the money, I mean, we never really talked about money until they made their offer. I mean, I never said I need, you know, it gave them a range or anything like that. They just made the offer, and, you know, I contemplated it, then ended up counteri…”
Jay Myers Apr 16, 2021 ▶ 25:41
Assertion Not checkable as stated
Myers: Personal Goodwill Allocation Saved Hundreds of Thousands in Taxes
“In our case, it saved hundreds of thousands of dollars in taxes because the tax rate was that much different. And I don't remember the exact percentages off the top of my head, but they were significant.”
Jay Myers Apr 16, 2021 ▶ 28:02
Insight
Myers: Sell when the business is ready, not when founders are
“It's not when you're ready, but when the business is ready.”
Jay Myers Apr 16, 2021 ▶ 29:59
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