Joey Trapasso

Reporting systems file a problem under the team or person whose name was on it, while the cause sat one step upstream and never appears in the same view.

• He tells managers to trace backwards: ask what a team was asked to do, not only what they failed to do.
• The same reasoning appears in a second post about results in general, where he argues a rep can blow out a quarter on one deal that fell into their lap, and a manager can look strong because they inherited a stacked team.

In one post he takes an NFL sequence: Javonte Williams walked into the end zone untouched and held the ball out at a Giants defender, drawing a 15-yard taunting penalty, which pushed the extra point to 48 yards, which Brandon Aubrey then missed.

• The miss is recorded next to the kicker's name; the penalty is not.
• He maps this onto revenue teams where an implementation misses its go-live date, a renewal is lost and an escalation goes unresolved, while the unapproved timeline and the functionality the product never had stay invisible.
• His closing question is direct: what were your people asked to do?

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Detection — a new CEO, a funding round, an acquisition — is well covered and no longer a differentiator.

• Matching a signal to the right opportunity is harder, because no tool remembers the exact reason a champion said no last year.
• He treats manic organisation as the actual skill, and argues that many of the hottest opportunities are already sitting closed and forgotten in the CRM while reps grind for new pipeline.

His evidence is the working habits of strong salespeople rather than a study: a spreadsheet with 14 colour-coded tabs, sticky notes on the monitor edge that have not moved since 2023, a notebook that looks like it belongs to the Joker. The point of those systems, he says, is to hold why every deal died and what would have to change for it to come back.

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Role-plays are unrealistic, product training is a feature dump reps cannot use, and then teams expect performance anyway. His alternative is repeated drilling of decision trees, sized to the stakes, on the stated logic that you practise for the call where you are behind — not for the call that goes well.

He uses a phishing test at Madison Square Garden after the Knicks won their first title in 53 years: employees were offered a free championship ring, it was a test, and anyone who clicked had to take a cybersecurity class.

• The test worked, he argues, because a real attack looks like the thing you want most — a bonus, holiday time off, the ring you were promised.
• In a separate post he describes how UFC champion Petr Yan's coach builds fight plans as decision trees — if Merab shoots a single leg, we do A; if that fails, we do B — quoting Yan's comparison of a five-page plan to a football playbook, and carries the structure over to sales as “conversation trees” drilled with role-plays, flashcards and recorded calls, growing from a cold call to a 30-minute discovery call to a 60-minute business case in front of a CFO.
• That coach's method and Yan's quote are their views as reported by Trapasso, not his own experience.

There is a real tension between this post and his argument against repeating a failing plan: here he admires a fighter who lost the first two rounds and kept to the plan because he expected the opponent to break. The two positions fit together only if the plan was tested and still sound — which is the distinction he draws elsewhere between commitment to a goal and commitment to an approach that is not working.

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His claim is that leadership rolls out an uncapped plan without expecting anyone to reach it, then reaches for fine print when someone does, and that the resulting backlash is always bigger than leadership expects. His advice runs the other way: pay the check, pay it on time, publicise it, and recognise that there is usually money when leadership decides the result is worth rewarding.

The hook is the Milwaukee Brewers' 2015 “Timeless Tickets” — 1,000 tickets at $1,000 each, good for any future home game with no expiration date.

• When the team reached the World Series, he notes reports that holders were offered terrace or standing-room seats while better seats were available in the public sale.
• He draws the line straight to sales compensation: the deal gets split, a cap appears, payment is spread over four quarters, or somebody decides it was a house account all along.

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He extends the same logic to leadership in transition: when a leader is on the way out, hard calls stop being made — territory changes wait, compensation questions wait, the rep who needs to be coached out waits — while the quarter still closes on the last day. His instruction is to make the change, name an interim and give someone on the team a real shot rather than a farewell tour.

He opens with the New York Yankees' $300 million roster and a problem money cannot fix, then cites Startup Genome's study of more than 650 startups, which found that companies which pivoted once or twice raised 2.5 times more money and grew 3.6 times faster than those that never pivoted or pivoted constantly.

• (The statistic is his citation and is not independently checked here.)
• The second post covers a WNBA season where no venue plan existed for a possible Game 6 even though the smaller arena holds 3,500 people and the bigger one was booked months earlier, so the decision was made hours before Game 5 and a potential championship game landed at 12:30pm on a Thursday.
• His summary line: “hope is not a plan,” delivered as something he tells his own reps.

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His position is that toughness, drive, desire, grit and resilience cannot be coached, so the person who wants it is the better bet, with the manager supplying coaching and support — and telling them to rest when they are running on empty. He treats recruiting as a related but distinct skill from sales, which is where he says strong sales leaders get caught out.

On Jalen Hurts he lists what cannot be coached and notes that Hurts was benched in a title game at Alabama, drafted in the second round as a backup plan and doubted every year, while outplaying Patrick Mahomes in two Super Bowls.

• The recruiting post compares recruiting and sales to football and rugby: the skills overlap but do not transfer, which is how a coach as accomplished as Rick Carlisle can look lost in a recruiting role.
• He adds that a candidate is leaving a team they know, a boss they trust and a paycheck they can count on for a promise from you, changing who they spend half their waking life with — and concludes that cringe is the cost of admission.

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Get those conditions right, he argues, and most capable reps will succeed, which is why judging a manager on results alone can mislead.

He points to Case Keenum, a 38-year-old quarterback who had not played an NFL game in 1,009 days, throwing three total touchdowns and winning a primetime game as a four-point underdog in Ben Johnson's offense.

• Trapasso's reading is that most competent quarterbacks would look good with time to throw to an open receiver, and that this is the point.
• In sales he names the equivalents: lead flow, tech stack, messaging and pricing.

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Start here because it is the cleanest statement of the argument behind most of the other posts.

Trapasso takes one play: Javonte Williams walked into the end zone untouched and held the ball out at a defender, drawing a 15-yard taunting penalty, which pushed the extra point from a short kick to 48 yards, which Brandon Aubrey then missed.

• The miss is recorded next to the kicker's name; the penalty is not.
• Trapasso carries the idea straight into revenue reporting.
• An implementation misses its go-live date, a renewal is lost, an escalation goes unresolved, and the dashboard files each one under the team that owned the failure.
• What the dashboard does not show, he argues, is that sales promised an unapproved timeline or sold functionality the product did not have.
• His closing instruction is concrete and easy to act on: ask your team what they were asked to do, not just what they failed to do.

For brands planning a campaign

This is the natural spine for a sponsored series or webinar on diagnosing deal loss. The football sequence gives a non-sales audience a fast way into attribution error, and the four-line example (implementation, renewal, support, sales) maps directly onto product surfaces a sales-software sponsor already sells into.

Read it second because it argues that the hard part of diagnosis has moved from finding triggers to connecting them to deals you already lost.

The post separates two jobs.

• Finding a signal, such as a new CEO, a funding round or an acquisition, is now cheap and covered by many tools.
• Matching that signal to the right opportunity is not, because no tool remembers the exact reason your champion said no last year.
• Trapasso's evidence for this is the working habits of strong reps rather than a study: a spreadsheet with 14 colour-coded tabs, sticky notes that have not moved since 2023, a notebook whose organisation looks deranged from the outside.
• His claim is that those systems exist to hold the reason each deal died and what would have to change for it to come back, and that most pipeline effort ignores opportunities already sitting closed in the CRM.

For brands planning a campaign

Best fit of the set for a product that stores CRM history or revives closed-lost deals. The useful angle for a sponsor is the gap between alerting and matching, which lets a vendor demonstrate its own workflow on the audience's real data rather than restate the value of buying signals.

Read it to see the training method he recommends when a rep has to answer under pressure.

Merab Dvalishvili set a UFC record with 58 takedown attempts across the trilogy with Petr Yan.

• Yan lost the first two rounds and kept to the plan, on the reasoning that once he started stopping the takedowns his opponent would break, and he won the last three rounds and the belt.
• Trapasso then describes how Yan's coach builds fight plans as decision trees, if this happens we do A, if that fails we do B, and notes the plan grew from one page to five, with Yan comparing it to a football playbook.
• He maps the same structure onto sales as conversation trees, drilled with role plays, flashcards and recorded calls, and sizes them to the stakes: a three-to-five-minute cold call, a 30-minute discovery call, a 60-minute business case in front of a CFO.
• The sharp line is that you drill for the situation where you are down two rounds, not for the call that goes well.

For brands planning a campaign

Useful for role-play, conversation-intelligence or call-recording vendors, because the post supplies a named method and a build sequence rather than a general claim about practice. A sponsored webinar could run one real conversation tree live and let the audience drill it.

Read it when the question is why reps can pass a course and still freeze on a live call.

After the Knicks won their first title in 53 years, MSG emailed employees an offer of a free championship ring.

• It was a phishing test, and anyone who clicked had to take a cybersecurity class, while many long-serving employees did not receive a ring at all.
• Trapasso's point is about realism, not about the test's fairness: a real attack does not look like a password reset, it looks like the thing you want most, such as a bonus, holiday time off or the ring you were promised.
• He borrows the military phrase train as you fight and applies it to sales, saying role plays are too clean and product training is a feature dump reps cannot use on a call, and then teams expect live performance anyway.

For brands planning a campaign

Strong material for an enablement, simulation or role-play sponsor. The Knicks story is a ready-made hook for a series episode about making practice resemble the buyer conversation, and it gives a vendor a specific failure to fix rather than a generic argument for better onboarding.

Read it to see how the sports story is built and how far the leadership parallel is taken.

The setting is the WNBA, where a commissioner who cannot keep pace with the league's growth is still in the seat.

• No one planned where to host a possible Game 6, even though the venue holds 3,500 people and the larger arena was booked months earlier, so the decision was made hours before Game 5 and a possible championship game landed at 12:30pm on a Thursday, 9:30am for West Coast fans.
• Trapasso states the rule directly, hope is not a plan, and then lists what he has seen in sales organisations in the same position: territory changes wait, comp questions wait, the rep who needs to be coached out waits, everything waits for the next person.
• His instruction is to make the change, name an interim and give someone on the team a real shot at the job rather than a farewell tour.

For brands planning a campaign

Fits a sales-leadership or revenue-operations sponsor, since the story gives a concrete case for acting on decisions that get deferred at quarter boundaries. It also shows this creator will argue a position, which matters when choosing a partner for a sponsored debate or panel rather than a product walkthrough.

Read it to see the set of skills he treats as shared between the two disciplines and where he says they diverge.

Trapasso's comparison is football and rugby, or baseball and cricket: skills overlap, but being a professional at one does not make you a professional at the other.

• He uses three-time NBA championship coach Rick Carlisle as the example of someone great at one job and clearly out of his depth in the other, and says many strong sales leaders behave the same way, either selling hard at a candidate who is evaluating them or holding back so much that they never sell the role at all.
• The argument he builds is about what is actually at stake for the candidate: they are leaving a team they know, a boss they trust and a predictable paycheck for a promise, and the change touches who they spend half their waking life with.
• His position is that cringe is the cost of admission.

For brands planning a campaign

Suitable for recruiting technology, employer branding or talent sponsors that sell to the same revenue leaders as a sales software audience. It also gives a sponsor a candidate-side angle rather than another seller-side pipeline angle.

Read it for the clearest version of the argument that results alone cannot tell you whether a strategy is working.

The starting point is three errors in the first inning of a game, following five unearned runs in the 2024 World Series that Trapasso says he was only starting to get over.

• From there he moves to go-to-market strategies at companies with good products, capable reps and real markets that still produce the same quarter after quarter.
• He cites Startup Genome's study of more than 650 startups, which found that companies which pivoted once or twice raised 2.5x more money and grew 3.6x faster than those that never pivoted or pivoted constantly, and distinguishes commitment to a goal from commitment to a plan that is failing.
• The line worth keeping is that you do not have to know what will work to recognise what is not working.

For brands planning a campaign

Gives a sponsor a data point and a framing for change management or planning products, and it works as a discussion prompt in a live session because the post ends by asking the audience what the fix would be. Note the pivot statistic is attributed to Startup Genome inside the post and has not been independently verified here.

He uses an NFL sequence: the box score records Brandon Aubrey's missed extra point, but not the taunting penalty that pushed the kick to 48 yards.

• He maps it directly onto revenue teams where the dashboard logs a missed go-live, a lost renewal, or an unresolved escalation, while the unapproved timeline, the unexplained discount, or the functionality the product never had stays invisible.
• His instruction to managers is to ask what a team was asked to do, not only what they failed to do.
• He makes the same point about results more broadly with the Dodgers, whose expensive signings and trades are survivable because of unusual margin for error, and with the rep whose blowout quarter came from one deal landing in their lap.

He takes a scoring or standings outcome, shows the unrecorded cause sitting one step upstream, then asks the reader to apply the same trace to a sales metric.

For brands planning a campaign

This is the closest existing body of work to the proposed brief. A sponsored series or webinar on deal-loss diagnosis can have him walk through his own method — reconstructing what a rep was asked to do before the loss — instead of presenting a vendor framework.

Examples: Source 1 · Source 2

Tools can flag a new CEO, a funding round, or an acquisition, but none of them can tell you why your champion said no last year.

• He describes the best salespeople as manically organized, with systems that look eccentric from the outside — a spreadsheet with 14 color-coded tabs, sticky notes that have not moved since 2023, a notebook that looks like it belongs to the Joker — and who know exactly why every dead deal ended and what would have to change for it to come back.
• The new challenge, in his framing, is staying organized enough to connect incoming signals to opportunities already sitting closed and forgotten in the CRM.

For brands planning a campaign

Gives the campaign a concrete wedge on closed-lost reactivation rather than net-new pipeline. The 'signal detection got cheap, signal matching didn't' line is a ready-made session title for a webinar on deal-loss review.

Examples: Source 1

Comparing the Knicks' phishing test to sales roleplays, he argues a real phishing attempt looks like the thing you want most — your bonus, holiday PTO, the championship ring — which is why the test worked, and that sales roleplays are too unrealistic while product training is a feature dump reps cannot use on a call.

• The Petr Yan post supplies his alternative: conversation trees, built by the fighter's coach as decision trees and drilled with roleplays, flashcards, and recorded calls, growing from a three-to-five-minute cold call to a 30-minute discovery call to a 60-minute business case in front of a CFO.
• The stated reason for the drilling is not to rehearse a call going well but to have the answer when you are down two rounds and cannot think.

He borrows a deliberately realistic test or a fighter's game plan, names the identical weakness in standard sales training, and describes the repeated practice that closes the gap.

For brands planning a campaign

A webinar could be built as a live drill rather than a talk, with a deal-loss scenario run through a conversation tree on camera. His stated position gives the campaign a reason to choose an interactive format over a presentation.

Examples: Source 1 · Source 2

His advice is to pay the big check, pay it on time, and make as much noise about it as possible, because the whole team is watching and the backlash is bigger than leadership expects. He also argues the team can afford it: there is usually money when leadership decides the result is worth rewarding.

For brands planning a campaign

Useful for a sponsor selling incentive, commission, or quota tooling, and a counterweight inside the deal-loss series: some losses are self-inflicted by how the company treats its own people. He is a credible voice on rep-facing trust rather than buyer-facing messaging.

Examples: Source 1

The Yankees post opens with a $300 million roster and a problem money cannot fix, then notes that a competitor publicly explained how to beat them and the same mistakes continued two years later; he cites Startup Genome research on 650-plus startups, where those that pivoted once or twice raised 2.5 times more money and grew 3.6 times faster than those that never pivoted or pivoted constantly.

• The WNBA post applies the same logic to leadership: with no plan for where to host a potential Game 6, the decision was made hours before Game 5 tipped, producing a possible championship game at 12:30pm on a Thursday.
• His verdict is that lame duck leaders stop making hard calls — territory changes, comp questions, coaching out a rep — and everything waits for the next person, while the quarter still closes on the last day.
• 'Hope is not a plan' is delivered as something he tells his own reps.

He holds up an organization with obvious advantages or obvious momentum, lists the mistakes it survived or made, and pulls out the decision that should have been made earlier.

For brands planning a campaign

Gives the series a strong opening episode: the cost of not adjusting mid-deal or mid-quarter. It also supports a manager-facing angle for a sponsor whose product surfaces early warning signs on stalled opportunities.

Examples: Source 1 · Source 2

On Jalen Hurts, Trapasso lists what cannot be coached — toughness, drive, desire, grit, resilience — and argues hiring managers over-weight industry experience, assuming someone who has not sold in their exact market will need too much coaching.

• His line is that you can teach the market and the product but cannot coach someone into caring or competing, and that the manager's job is to give that drive coaching and support, and to tell the person to rest when they are running on empty.
• The recruiting post frames recruiting and sales as cousins, like football and rugby: skills overlap, but being a pro at one does not make you a pro at the other, which is how a great head coach ends up with no feel for recruiting.
• He stresses that a candidate is betting their life on you, leaving a team, a boss, and a paycheck they can count on, and concludes that cringe is the cost of admission.

For brands planning a campaign

Supports a campaign segment on who should run the deal-loss review — the rep closest to the deal or an outside expert with more industry experience. It also opens a second series topic for sponsors in recruiting or sales-enablement software.

Examples: Source 1 · Source 2

Trapasso's reading is that a good system helps capable people succeed, and that this is what a manager is for: building the system and taking care of the things their people cannot control. In sales he names those things as lead flow, tech stack, messaging, and pricing, with the claim that getting them right means most capable reps will succeed.

For brands planning a campaign

A manager-targeted episode in the series, and a natural slot for sponsors in sales engagement or revenue operations whose products touch lead flow and the tech stack he lists.

Examples: Source 1

The sports scene supplies the specific observation: five pages of game-plan decision trees, a 15-yard taunting penalty, a $240 million signing's worst season, 1,000 tickets sold in 2015.

• The business point is the transfer, and the transfer is nearly always about a revenue team rather than the sport itself.
• The pattern is consistent enough to be his recognizable format, and the closing question is a recurring engagement device rather than an occasional one.

Each post runs a fixed chain: sports hook, the specific detail that carries the argument, the sales or management equivalent, then a question back to the reader.

The Knicks phishing-test post uses a business news story instead of a live sports result, but keeps the same hook-and-transfer structure, which is why the format reads as a device rather than a baseball-only habit.

For brands planning a campaign

Sponsored content should follow the same shape: one concrete scene, one named transfer to sales, one prompt for the audience. He may need a sports or current-event entry point — or a news story like the Knicks phishing test — to sound like himself in brand work.

Examples: Source 1 · Source 2 · Source 3 · Source 4 · Source 5 · Source 6 · Source 7 · Source 8 · Source 9 · Source 10 · Source 11

Both write about pipeline discipline and about catching a stalled deal before the quarter ends rather than after it.

Zides writes from his own operating history and a named method, The UNLOCK Method, with first-person stories about CoreAxis and founder-led sales. Trapasso stays outside the anecdote and borrows a sports event to carry the teaching, and his range extends further into hiring, training and compensation.

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Both treat alignment across sales, marketing and customer success as the underlying fix.

Scheifler's method is a customer score built from CRM, delivery and leadership inputs and reviewed with a client's executive team, and her posts show the scoring conversation directly and end with an invitation to get in touch. Trapasso's diagnostic is narrative reconstruction — asking what a rep was asked to do — and his posts close with a discussion question rather than an offer.

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Wilson's Alex Cora post and Trapasso's box-score post both tell managers to look upstream of the person whose name is on the result.

Wilson writes from more than twenty fractional VP of Sales engagements and names the pattern found across them, and the reviewed posts carry a partner recommendation and a direct offer of services. Trapasso generalizes from public sports moments without client stories, rotates through several sports, and is more likely to end in a question than an invitation.

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The same campaign decision — helping a B2B sales software company show buyers how to find deal problems before they land on a dashboard — can be served by Zides's weekly pipeline review, the hour he put on the calendar every Friday at CoreAxis and has run in some form at every company since.

• Every deal got the same question: what would it take to move this toward close next week?
• The second reviewed post extends that into a founder math argument: 15 selling hours a week, one deal eating 10 of them, roughly 75 deals a year never taking a vacation, and a $3M ceiling at $40K a deal.
• A sponsor whose product manages pipeline cadence, forecasting, or founder-led selling can build a series or webinar around that rhythm and reach founder-operators directly.
• The case for Zides is strongest if the brief shifts from diagnosing a loss to scheduling the review that catches it earlier.

Zides does not walk through one deal's chain of causes.

• The retained posts stay at the level of cadence and arithmetic, so a sponsor looking for the forensic trace that anchors the Trapasso fit — a specific recorded failure, the decision that produced it, and the instruction a rep can reuse — will not find it here.
• The format is also less repeatable for adaptation: one of the two posts is a newsletter promotion pointing readers to a link in the comments rather than a self-contained argument.
• If the campaign depends on inspectable examples of a single deal going wrong, Joey Trapasso covers that ground and Zides does not.

Examples: Source 1 · Source 2

For a B2B sales software company, the same decision — moving buyers past dashboard-level reporting — becomes an account-fit argument.

• Scheifler describes bringing a CEO, head of sales, head of marketing, and customer success into one conversation about best customers: who the champion was, why the company needed the solution, whether it had implemented something similar before, then turning that into a score built into the CRM.
• The concrete illustration is a client comparing existing customers rated around 50 against pipeline prospects rated 10 or minus 5, and the conclusion that a bad-fit account usually does not survive renewal.
• A sponsor selling scoring, ICP alignment, or CRM data work can use that to reach teams whose pipeline is full and nothing is closing.
• She also takes up a question from Sangram Vajre's newsletter about what breaks first when AI enters go-to-market, landing on the point that AI exposes cracks already present.

Scheifler's material diagnoses fit, not loss.

• It does not trace what happened inside a deal that stalled or died, and it offers no drill or live exercise a producer can run on air.
• The retained evidence is also thin for a series: two short posts, and one closes with a direct-service call to action rather than a reusable method.
• Part of the AI argument is attributed to Vajre's newsletter and to Bryan Brown, so a sponsor building around that theme is partly buying a curated summary rather than Scheifler's own analysis.
• If the campaign needs a repeatable post structure or a working session the audience completes, Trapasso's reviewed posts supply both.

Examples: Source 1 · Source 2

Wilson's reviewed post frames the same beyond-the-dashboard problem at the leadership level: the sales leader is almost never the problem, the sales leader is usually the evidence of the problem.

• Thin pipeline usually traces to an ICP that was wrong before anyone walked in the door, stalled deals to a sales cycle that was never designed and just evolved, and reps who cannot close to a demo that is a feature tour nobody asked for.
• The post names a specific pattern of fractional engagements — product not ready for the target market, pricing that forces every deal into a weak negotiation, an untouched CRM, a 90-day mandate to fix sales — and reports 21-plus such engagements.
• A sponsor whose product surfaces root cause before a sales hire, or that supports fractional sales leadership, can build a leadership-facing webinar from that argument.

The claims rest on Wilson's stated engagement history and the posts do not show deal-level evidence behind them, so a sponsor gets strong diagnostic framing without a verifiable specific trace.

• Only one of the two retained posts carries the argument; the other is a recommendation for a HubSpot consultant, which narrows the material for a multi-part series and would not support a HubSpot-adjacent campaign without more evidence.
• Wilson also does not supply the sports-hook-plus-sales-transfer structure or the closing audience question that made Trapasso's posts adaptable episode by episode, and there is no drill method for a live session.
• Choose Wilson for executive root-cause framing; choose Trapasso when the campaign has to demonstrate the diagnosis on a deal or rehearse the hard conversation.

Examples: Source 1 · Source 2