Hi Reader

Welcome to this week's edition. There's a leadership thread running through most of what caught my eye this week, from the biggest CEO handover in tech to fresh research on why founder transitions go wrong, and a few useful reminders that the most boring marketing fundamentals are still the ones that win. A good Friday batch heading into the weekend.

Enjoy!

The biggest succession story in tech finally has a date

Apple confirmed this week that Tim Cook will hand the chief executive job to John Ternus on 1 September, with Cook moving up to executive chairman. Cook has run the company for 14 years, taken its market value past $3 trillion, and managed something almost no founder-successor pulls off, which is to make the second act look as steady as the first. Ternus, an engineer who has been at Apple since 2001, is a textbook internal pick: long tenure, deep product credibility, no ego brand of his own.

What makes this notable beyond Apple is how often it's now happening. Cook joins a wave that includes Doug McMillon stepping aside at Walmart and Bob Iger's handover at Disney, with Fortune calling it a "CEO reckoning" sweeping corporate America. For founders and SME owners, the interesting shift is not that long-tenured leaders are leaving, but that boards are increasingly choosing operationally trusted insiders over visible outside celebrities. The signal is that continuity beats charisma when the next chapter looks unpredictable. Read it here (paywalled so access through Archive).

Why founder handovers fail more often than people admit

Linked to the Cook news is a useful HBR piece on what actually goes wrong when a founder hands over the keys. The authors draw on research showing that founder-CEO handovers fail at significantly higher rates than other leadership transitions, and the reasons are rarely about competence. They're about identity, residual control and the tendency for a founder to keep tugging at the wheel long after they've supposedly let go.

The piece is honest about how hard the psychological reset is, even for founders who genuinely want to step back. It also makes the practical case that the work begins long before the announcement: clear decision rights, an explicit role for the outgoing founder, and a board willing to back the new chief executive when the old one inevitably second-guesses something. For anyone building towards a sale, a recapitalisation or a generational handover, this is worth reading slowly. The point of it isn't about exit mechanics. It's about whether the business can actually function once you're no longer in the middle of it. Read the article here.

The quiet trap inside earn-outs that founders keep walking into

Earn-outs have made a serious comeback in the current deal market, mainly because buyers and sellers cannot agree on what a business is worth right now. The structure looks elegant on paper: bridge the valuation gap by tying part of the price to performance after completion. In practice, a fresh Reed Smith analysis of UK and US deal data confirms what most M&A advisers already know, which is that earn-outs are the single most common source of post-completion disputes.

The recurring pattern is that the seller assumes the business will be run roughly as before, while the buyer assumes they have bought the right to integrate, restructure and re-prioritise. Both can be correct depending on how the document is drafted, which is why the disputes that follow are often genuinely intractable. For founders considering an exit in the next 12 to 24 months, the lesson is to negotiate the earn-out mechanics with the same intensity as the headline number. Worth reading if you're in the early stages of a sale conversation and tempted to leave deal protection language to the lawyers at the end. Find out more here.

Specsavers shows that boring marketing is still the best marketing

Specsavers picked up Brand of the Year at the most recent Marketing Week Awards, which felt almost unfair given how many flashier contenders were in the running. A new podcast with the brand's marketing leadership unpacks why. They describe their approach as "common-sensical" marketing: a long-running idea that everyone in the country recognises, consistent media weight, distinctive visual codes, and absolutely no urge to reinvent the brand every time a new agency or chief executive arrives.

It's a useful counterpoint to the constant industry pressure for transformation. Specsavers' "should've gone" line has been running for over two decades, and the discipline of keeping it fresh without breaking it is harder than launching something new. For SME founders who occasionally wonder whether their marketing needs a complete overhaul, the more useful question is usually whether the existing positioning has been given enough time and weight to actually land. Check it out here.

Why creativity is becoming marketing's last real moat

A thoughtful piece in The Drum makes the case that as AI flattens the cost of producing competent advertising, the only real differentiator left for brands is creativity itself. The author's argument is that performance media, targeting, copy production and even basic creative variations are quickly becoming commodities. What still requires a human point of view is genuine distinctiveness: an idea that makes someone pause, share or remember.

It chimes with something I've been thinking about for a while. A lot of founders treat marketing as primarily an efficiency game, looking for the cheapest way to get a message in front of the most people. That works up to a point, but in a world where every competitor has the same AI-generated assets, the brands that stand out will be the ones willing to spend on ideas rather than just impressions. Find out more here.

A useful playbook of what's actually working in enterprise AI

Stanford's Digital Economy Lab, with Erik Brynjolfsson, has published a useful study of 51 successful enterprise AI deployments. It cuts through a lot of the noise about pilot failure rates by focusing on what the organisations getting real returns are actually doing differently. The headline finding is that the model itself accounts for a small fraction of success. The bigger work sits in process redesign, data cleanup, governance and, crucially, the willingness to rewire how decisions get made.

What makes this report particularly useful is its grounded tone. There are no breathless predictions about agents replacing departments overnight. Instead, it's a careful look at what high-performing AI organisations spend their money on, which turns out to be roughly the same boring infrastructure work that defined every previous wave of useful technology. For anyone wondering why their pilots are not yet producing the gains the vendor slides promised, this is a sober and helpful explanation. Get the report here.

The Fed has spotted a worrying gap between bosses and workers on AI

A new note from the US Federal Reserve looks at AI adoption data and finds something most boardrooms would rather not discuss openly: senior leaders consistently expect much larger productivity gains from AI than the workers actually using the tools. Leaders also expect more job displacement than employees do, which is a polite way of saying that the people writing the AI strategy and the people executing it have meaningfully different views of where this all ends.

The reason this matters for SMEs is that the same gap exists at smaller scale. Founders read the same hype, attend the same conferences, and often arrive at investment decisions that assume their teams will absorb the change at the pace the slides imply. They rarely do. It's a reminder that the messy middle of AI adoption, where people are quietly working out what's useful and what's a distraction, deserves more attention than the next strategy offsite. Read it here.

Gen Z is sending a workplace warning that companies keep ignoring

A sharp Fortune piece this week looks at what's been labelled the "Gen Z stare" and the "Gen Z pout", the slightly awkward signals younger employees give when leaders explain decisions that don't quite stack up. The piece is more interesting than the framing suggests. The argument is that companies dismissing Gen Z behaviours as fragile or entitled are systematically defunding their own future leadership pipeline. By 2030, this generation will be roughly 30 per cent of the workforce.

The useful read for founders is not about generational stereotypes. It's about how quickly trust evaporates when the gap between what leaders say and what the team can see widens. That dynamic isn't unique to Gen Z, but they happen to be the cohort least willing to pretend the gap isn't there. For anyone leading a team where younger employees are quietly checking out, the most useful question is rarely "what's wrong with them" but "what are we asking them to ignore". Get the story here (paywalled so access through Archive).

The pricing decisions most founders make on instinct probably shouldn't be

A new academic review from Simon-Kucher pulls together a decade of behavioural pricing research and makes a slightly uncomfortable argument: most SMEs price their products and services on intuition, gut and "what feels right", and most of them are leaving meaningful margin on the table as a result. The work covers the familiar territory of charm pricing, anchoring and decoy effects, but the more useful section is on how perceived value scales when prices are presented in groups rather than individually.

What makes this worth reading is that it isn't about clever tactics. It's about treating pricing as a strategic discipline rather than a one-off decision made when the product launched. For most founders I know, including some experienced ones, pricing reviews happen far less often than they should and almost always default to "let's not change it because customers might notice". Find out more here.

AI prompt of the week: pre-diligence stress test

Most founders only discover what's wrong with their business when a buyer's diligence team starts pulling the company apart. This prompt runs a structured pre-mortem on the most common areas where deals stall, so you can fix the leaks while you still control the timeline.

Help me run a pre-diligence stress test on my business as if I were preparing for a sale or investment in the next 12 months. My context: [business type], [annual revenue], [team size], [ownership structure], [key contracts], [main customer concentration], [legal jurisdiction], [last year's biggest growth driver], [biggest current operational concern].

Create:

A clear assessment of the areas a sophisticated buyer would scrutinise hardest, including financial quality, customer concentration, contract risk, key-person dependency, IP ownership, regulatory exposure, technology debt and team continuity.

A red-flag inventory listing the issues most likely to either reduce valuation or kill a deal entirely, with a plain explanation of why each one matters to a buyer.

A practical 90-day fix list showing what could realistically be cleaned up before any process starts, separated into financial, legal, operational and commercial workstreams.

A list of the documents and data a buyer will expect to see in a data room, with a status check on whether each one currently exists, needs work, or is missing entirely.

The questions a smart adviser would ask the founder before agreeing to take the business to market, designed to surface anything I might be downplaying.

A short summary of what would make this business genuinely "buyer ready" rather than just "for sale", with a sense of how long that work would take.

Base this on how strong M&A advisers and seasoned acquirers actually diagnose readiness, separating presentational fixes from the structural issues that move price and certainty.

Where deals quietly fall apart

Most M&A failures are not dramatic. They tend to be the slow accumulation of small problems that buyers spot in diligence and use to chip away at price, terms or certainty. The risk is that founders only notice the pattern after the deal is done, or worse, after it has fallen over.

Below is a quick visual reference of the most common deal-killers. Worth keeping somewhere visible if you're inside a process, considering one in the next year or two, or simply trying to make sure your business doesn't accumulate the kind of issues that compound quietly over time.

Drop me a line

That's everything for this week. As ever, the best part of putting this together is hearing where readers push back, expand on something or send a useful link in return, so do reply if anything here sparks a thought.

Cheers!

Adam