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#4275The Ins and Outs of Selling a Business54.0 / 100Get badge
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The Ins and Outs of Selling a Business

Hosted by Keith Dee, Osage Advisors

This podcast taps the expertise of Keith Dee, President and CEO of Osage Advisors, with more than 30 years of experience advising business owners and families of midsize companies and helping them maximize value through M&A and capital transactions.

100 episodes · publishes weekly · latest 2026-06-25 · ~15 min/episode

Rank

#4275

Substance

54.0

/ 100

Breakdown

Scored 2026-07
Updated monthly

Finance rank

#471 of 548

Best B2B Finance Podcasts →

Across the index

#4275 of 6183

Substance

Top 69%

outscores 31% of the index

Why it scores where it does

The Ins and Outs of Selling a Business ranks #4275 on The B2B Podcast Index with a substance score of 54.0 out of 100, scored across 1 recent episode. It scores highest on guest caliber and insight density. Mark Emmer is a credible strategic planning practitioner with a substantial client roster (200+ organizations) and real Vistage-level exposure to mid-market CEOs, but he speaks as a consultant-advisor rather than as an operator who has personally built and exited a business at scale, limiting the depth of hard-won practitioner insight.

The five-dimension breakdown

Averaged across 1 recently scored episode, with cited evidence.

Insight Density

11.0 / 20

There are a handful of useful, if not novel, observations - particularly on earnout psychology and the danger of post-close rigidity - but most of the episode is familiar M&A preparation advice padded with pleasantries and host monologues. The density of actionable ideas per minute is low for a 20-minute runtime.

“the seller is holding on too tight to what they did before. You know, so if you're in an earn out situation and now you're working for somebody else, it's not your problem anymore”

“sellers have earnouts, you know, they only get to the end of their earn out like half of the time because they get kind of checked out”

Originality

10.0 / 20

The episode recycles standard sell-side advisory wisdom - advisors matter, market position drives premium, alignment is key, second bite of the apple - with no contrarian or first-principles framing. The Marsalis anecdote is the lone attempt at a fresh angle but is applied as a generic 'preparation beats chaos' metaphor.

“in times of chaos, we need to be more deliberate, we need to be more process driven. In other words, we earn the right to be agile through preparation”

“I think of uh, a, uh, strategy like it's a sheet of music and we're a symphony and everyone has to play their part”

Guest Caliber

14.0 / 20

Mark Emmer is a credible strategic planning practitioner with a substantial client roster (200+ organizations) and real Vistage-level exposure to mid-market CEOs, but he speaks as a consultant-advisor rather than as an operator who has personally built and exited a business at scale, limiting the depth of hard-won practitioner insight.

“I've had several clients in transactions recently that not only did they max out their earnout, they got stock in the, uh, purchasing company, which was more valuable than their business was”

“Mark facilitated strategy for more than 200 organizations”

Specificity & Evidence

9.0 / 20

The episode is almost entirely abstract: no named companies, no cited research, and the only figures are hypothetical round numbers offered by the host as illustration rather than real deal data. The single quasi-statistic ('half of the time' on earnouts) is completely unattributed.

“they only get to the end of their earn out like half of the time”

“you got 10 million for your company you stayed with for three years. They sell out down the road at a 3x or 4x or 5x, and next thing you know, you get another check for 20 million”

Conversational Craft

10.0 / 20

The host frequently answers his own questions with lengthy anecdotes and statements that seek validation rather than new information, leaving the guest little room to develop ideas; there is no meaningful pushback, challenge of claims, or productive disagreement across the entire episode.

“I mean I had a situation where you know, the son and the father, the son didn't, didn't want it to go and the father says I need to go. Right. And, and he did everything in his power”

“you know, um, in today's market we are seeing more structure in deals that um, is contingent notes, earnouts and you know Typically we talked about this before”

Standout episodes

  • The Final Months Before a Sale Can Make or Break Your Exit

    2026-06-25

    54

Rank over time

First period on the Index - history builds from here.

Episodes

1 scored on substance · 60 tracked in total.

  • The Final Months Before a Sale Can Make or Break Your Exit

    2026-06-25 · 20 min

    54 / 100

Frequently asked

What is The Ins and Outs of Selling a Business's substance score?
The Ins and Outs of Selling a Business scores 54.0 out of 100 for substance and ranks #4275 on The B2B Podcast Index. That puts it ahead of 31% of the B2B podcasts we rank and #471 of 548 in Finance. The score reflects insight density, originality, guest caliber, specificity and conversational craft across recent episodes - not downloads.
Is The Ins and Outs of Selling a Business worth listening to?
The Ins and Outs of Selling a Business is ranked on The B2B Podcast Index with a substance score of 54.0/100. See the five-dimension breakdown above to judge whether it fits what you're after.
Who hosts The Ins and Outs of Selling a Business?
The Ins and Outs of Selling a Business is hosted by Keith Dee, Osage Advisors.
How often does The Ins and Outs of Selling a Business publish?
The Ins and Outs of Selling a Business publishes weekly, has 100 episodes, released its most recent episode on 2026-06-25.
Which The Ins and Outs of Selling a Business episode should I start with?
Our highest-scoring recent episode is "The Final Months Before a Sale Can Make or Break Your Exit" (54/100) - a good place to start.

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Guests who've appeared

Mark Emmer

Topics this show covers

The themes that come up most across this show's episodes.

Strategic planningsuccession planningmarket positioningEarnout structuresbuy-sell agreementsOptimize Inc.Vistage Internationaltransactional attorneysfamily business alignmentequity rollover

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