Giacomo Balli profile picture
Giacomo Balli
Your Consigliere

For owners and founders facing decisions that are expensive to get wrong.
Independent counsel from someone paid only by you.

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Writing on technology decisions, AI and buying software: 634 posts since 2012.

206 posts in Business

2026

267 posts
  1. OpenAI is commoditizing successful AI startups unusually fastOpenAI is commoditizing successful AI startups unusually fast: Meta Muse XAI Grok Bot → Dots.TypeSafe AI Jev → Decisions API.Agent frameworks → Codex...

    1 min readAI

  2. Your most exposed IP may be how your company knows what to doYour most exposed IP may be how your company knows what to do. Companies worry about sending the confidential PDF, the source code or the customer list to...

    2 min readAI

  3. Who would have known so much information is publicly available?😱 Discuss on LinkedIn

    1 min readBusiness

  4. Companies may be about to fire exactly the wrong peopleCompanies may be about to fire exactly the wrong people. Not because AI can’t do a lot of their work.

    2 min readAI

  5. The size of the invoice is the wrong measure of a decisionOwners tend to judge whether a decision deserves scrutiny by the size of the invoice. The invoice is the wrong instrument.

    1 min readReading

  6. Before your next technology investment, ask someone who gains nothingBefore your next major technology investment, ask one person who does not make more money if you say yes. Count the people who have been involved so far.

    2 min readProduct

  7. The best recommendation I can give is sometimes "don't build anything"The best technology recommendation I can give a client is sometimes "don't build anything." It is also the one clients find hardest to accept, because they...

    1 min readEngineering

  8. "Our competitor is doing it" is the worst justification for a tech investment"Our competitor is doing it" may be the worst justification for a technology investment that a sensible executive regularly accepts.

    2 min readEngineering

  9. A $5,000 technology decision can deserve more scrutiny than a $500,000 oneA $5,000 technology decision can deserve more scrutiny than a $500,000 one. Owners scrutinise by price, and price is a poor guide to consequence.

    1 min readAI

  10. A CEO sent me a technology proposalA CEO sent me a technology proposal. These are the first three things I ignored. The feature list.

    1 min readBuying Software

  11. If a CEO sent me a $500k software proposal tomorrow, this is what I would reviewIf a CEO sent me a $500k software proposal tomorrow, this is what I would review, in order. The problem statement, before the solution.

    2 min readBuying Software

  12. Don’t make the intelligence safe enough to trustDon’t make the intelligence safe enough to trust. Make the environment safe enough that intelligence doesn’t need to be trusted.

    1 min readBusiness

  13. A popular website with no app is usually not an opportunitySomeone will eventually bring you a popular website with no app and call it an opportunity. Usually it is not one.

    1 min readMobile

  14. When should a CEO get a second opinion on a technology decisionNot on all of them. There are thresholds, and they are worth writing down before the next proposal arrives, because after it arrives the answer is always...

    2 min readBuying Software

  15. The person recommending the technology should not be the only one valuing itThe person recommending the technology should not be the only person estimating its value.

    2 min readAI

  16. Competent executives make surprisingly bad technology purchasesCompetent executives make surprisingly bad technology purchases, and it is not a judgment problem.

    2 min readEngineering

  17. The contract clauses that create the most lock-in get the least scrutinyThe technology contract CEOs scrutinise least is often the one that creates the most lock-in. Price and term get negotiated.

    2 min readBuying Software

  18. I shipped an app that got 47 downloads and zero dollars in 90 daysI shipped an app that got 47 downloads and zero dollars in 90 days. It was one of the better built things I have made.

    1 min readMobile

  19. The most worrying sentence in a vendor demo: "Yes, we can customise that"The sentence in a vendor demo that should worry you most is "Yes, we can customise that." It sounds like flexibility.

    2 min readBuying Software

  20. The software demo was fantasticThe software demo was fantastic. That is almost irrelevant. Demos are built to be demoed. The data is clean, the user is an admin, the workflow is the one...

    2 min readEngineering

  21. Changing ERP or CRM systems often recreates the old company's problemsChanging ERP or CRM systems often recreates the old company's problems in a newer database, and the reason is in the implementation plan.

    2 min readEngineering

  22. Before replacing your CRM or ERP, check whether the software is the problemBefore replacing your CRM or ERP, find out whether the software is actually the problem. Most of the time it is the thing everyone can agree to blame.

    2 min readEngineering

  23. The best model is becoming a surprisingly bad defaultThe best model is becoming a surprisingly bad default. I was about to tokenmaxx my Claude weekly quota, so I switched to Sonnet 4.5.I expected a noticeable...

    1 min readAI

  24. Your CTO says the architecture needs to be rebuiltYour CTO says the architecture needs to be rebuilt. You cannot evaluate the architecture. You can evaluate the claim.

    2 min readEngineering

  25. A CEO I advise canceled the company's hosting accountA CEO I advise canceled the company's hosting account, expecting the servers to keep running until the end of the month.

    1 min readEngineering

  26. A software project can be on time and already lostA software project can be on time and already lost. Late is the last sign, not the first. These are the ones that show up earlier.

    1 min readEngineering

  27. An ad group of mine was set to exact matchAn ad group of mine was set to exact match. It spent 96% of its budget on something else. A setting called Search Match was switched on underneath it, so...

    1 min readProduct

  28. Your business probably does not need an appYour business probably does not need an app. I have shipped apps since 2010, so this is not a position I hold lightly.

    2 min readPricing

  29. Custom software should have to earn the right to existCustom software should have to earn the right to exist. The default answer to "should we build this" is no, and the burden of proof sits with the build.

    2 min readEngineering

  30. The $20 AI tool versus the $200,000 AI implementationThe $20 a month AI tool and the $200,000 AI implementation are often pitched for the same problem, and the honest answer about which one you need is usually...

    1 min readAI

  31. Your team just proposed an AI initiativeYour team just proposed an AI initiative. These are the questions I would ask before approving the budget, in the order I would ask them.

    1 min readAI

  32. The dangerous AI project is the one that worksThe dangerous AI project is the one that works. Failures are cheap. The working one stays.

    1 min readAI

  33. "We need an AI strategy" is usually the wrong first sentence"We need an AI strategy" is usually the wrong first sentence, and it produces a predictable document: a list of AI capabilities with your company's name...

    1 min readAI

  34. The last moment a replacement decision is still cheap to changeA client mentions, almost in passing, that they are getting a quote to replace the system that runs the business.

    1 min readEngineering

  35. Before spending $250k building software, spend a week trying to kill the ideaBefore spending $250k building software, spend a week trying to kill the idea. Not a week of planning.

    2 min readEngineering

  36. Your vendor says you need a custom solutionYour vendor says you need a custom solution. Of course they do. That is not an accusation.

    1 min readBuying Software

  37. The most useful question before approving a software projectAsk it in the meeting where the budget gets requested, and watch the room. If the answer is a number, keep listening.

    1 min readEngineering

  38. Share of new apps with "AI" in the name, by year: 0.1% through 2016Share of new apps with "AI" in the name, by year: 0.1% through 2016. 6% so far in 2026. The peak was last year.

    1 min readAI

  39. The biggest App Store developers are the ones you've never heard ofThe biggest players are the ones you have never heard of Ask anyone who the biggest developers on the App Store are and they will say Google, Meta, maybe...

    1 min readEngineering

  40. I pulled every live app on the US App Store into a database this weekI pulled every live app on the US App Store into a database this week. 1.13 million apps. Then I looked only at the ones businesses build for their customers.

    1 min readMobile

  41. The expertise that built an institution can quietly become the reason it stopsThe expertise that built an institution can quietly become the reason it stops learning. Past success gives leaders judgment and pattern recognition, but it...

    1 min readAI

  42. AI changes the backlogAI changes the backlog. Economically:Lower implementation cost → lower experimentation threshold → more experiments → more discovered demand.

    1 min readAI

  43. 37signals let designers use agents to implement features37signals let designers use agents to implement features. Individual PRs looked reasonable, but collectively they degraded the architecture enough that...

    1 min readAI

  44. The best AI for your business probably won’t be the smartest oneThe best AI for your business probably won’t be the smartest one. The big, powerful AI models will keep pushing the limits.

    1 min readAI

  45. I brought in Codex as an adversarial critic of my thinking with ClaudeI was worried I was delegating too much of my thinking to Claude so I brought in Codex as an adversarial critic.

    1 min readAI

  46. AI demos work because the data is cleanAI demos work because the data is clean. Your data isn't, and that's the actual reason the pilot underwhelmed.

    1 min readAI

  47. Your company may own a valuable data asset that has never appeared on yourYour company may own a valuable data asset that has never appeared on your balance sheet. Every quote you sent, customer you lost, support issue you solved...

    1 min readAI

  48. "We don't have anyone who knows how to do this." Neither did the companies"We don't have anyone who knows how to do this." Neither did the companies that figured it out.

    1 min readAI

  49. Most AI pilots produce nothing measurableMost AI pilots produce nothing measurable. That's not a technology problem. It's a scoping problem, and it looks like this: the pilot starts with "let's see...

    1 min readAI

  50. "What if I get a $4,000 bill?" This is the most solvable fear on the list"What if I get a $4,000 bill?" This is the most solvable fear on the list and almost nobody addresses it before signing up.

    1 min readAI

  51. "I don't trust it to be right." You shouldn't"I don't trust it to be right." You shouldn't. That's the correct instinct and it's the wrong conclusion. The mistake is framing this as trust vs no trust.

    1 min readAI

  52. Every customer issue should make the company slightly harder to surprise nextEvery customer issue should make the company slightly harder to surprise next time. A support call that ends with “fixed” is only half-finished.

    1 min readStartups

  53. A $150k employee no longer costs $150kA $150k employee no longer costs $150k. AI is making employee cost dynamic. Salary is only the starting point.

    2 min readAI

  54. Everyone seems focused on when we’ll reach AGIEveryone seems focused on when we’ll reach AGI.But I think we’re missing the more immediate point: the AI we already have is capable of doing a huge portion...

    1 min readAI

  55. Newer AI models cost more per token but often still cheaper to useNewer AI models cost more per token but often still cheaper to use. Because smarter models often need fewer tokens to get the job done.

    1 min readAI

  56. Building software is no longer the hard part of starting a companyBuilding software is no longer the hard part of starting a company. That's exactly why more founders are going to build products nobody wants.

    1 min readAI

  57. Signs your business has outgrown its off-the-shelf softwareThe clearest signs you have outgrown a generic tool are spreadsheets duct-taping gaps, unused seats, manual workarounds, broken integrations, and data trapped in silos.

    6 min readBuying Software

  58. How to make AI "know everything" about your businessI often get asked by companies how they can make AI "know everything" about their business.

    2 min readAI

  59. Companies are struggling to innovate because nobody has priced the costCompanies are struggling to innovate because nobody has priced the cost of keeping legacy systems.

    2 min readStartups

  60. This might seem like a joke, but is it reallyDiscuss on LinkedIn

    1 min readBusiness

  61. X (formerly Twitter) started asking Claude for moneyX (formerly Twitter) started asking Claude for money. Discuss on LinkedIn

    1 min readAI

  62. I spend a lot of time helping business owners think through AI strategyI spend a lot of time helping business owners think through AI strategy. One thing that keeps coming up is that we've been assuming AI agents will use...

    2 min readAI

  63. The people most obsessed with startup ideas rarely start a companyThe people most obsessed with finding startup ideas are often the least likely to start a company.

    2 min readAI

  64. Many CEOs get blamed for decisions the incentive system was designed to produceMany CEOs get blamed for decisions the incentive system was designed to produce. A board meeting rarely starts with, “What’s best in the long term?” It...

    1 min readEngineering

  65. When intelligence becomes abundant, customers pay for outcomesIf, as predicted, intelligence becomes abundant, customers stop paying for:reportsdashboardsqueriesworkflow clicks ...they will start paying for:guaranteed...

    1 min readEngineering

  66. AI is unbundling professional services by deleting the middle of the workAI is unbundling professional services by deleting the middle of the work. The “judgment sandwich” is becoming obvious.

    1 min readAI

  67. In some companies you’ll see headcount traded for tokensIn some companies you’ll see headcount traded for tokens. Not because leaders suddenly prefer “AI” to humans, but because tokens look like a variable cost...

    2 min readAI

  68. The most effective way to disrupt an incumbent is to remove the problemThe most effective way to disrupt an incumbent is to remove the problem it was created to solve. OpenAI Sites feels like another step in that direction.

    1 min readAI

  69. Domain expertise has always been the real moat because it is the only advantageDomain expertise has always been the real moat because it is the only advantage you cannot buy on a roadmap.

    1 min readAI

  70. I’ll be honest: it makes me sadI’ll be honest: it makes me sad.Ferrari just unveiled its first-ever electric car: the Luce.

    1 min readProduct

  71. A 2014 study shows walking significantly boosts creative thinkingJust came across a fascinating 2014 study from the American Psychological Association that scientifically validates something I've experienced for years...

    1 min readProduct

  72. Most of my work happens in abstractionMost of my work happens in abstraction. Systems.Strategy.Second-order effects.Future scenarios.Trade-offs.

    1 min readMobile

  73. Wow, this piece brought back so many memoriesWow, this piece brought back so many memories... grazie Andrea Fortuna! Discuss on LinkedIn

    1 min readBusiness

  74. Coding and design keep getting cheaperCoding and design keep getting cheaper. What costs business owners money now is quality uncertainty, because it turns every launch into a hidden warranty.

    1 min readEngineering

  75. I’ve been in mobile since 2010I’ve been in mobile since 2010. ASO has always been part of the game, so over the years I’ve tried nearly every tool that entered the market.

    1 min readAI

  76. AI adoption fails when learning stays trapped inside individual workflowsAI adoption fails when learning stays trapped inside individual workflows. A developer at Siemens may find a better way to use agents in code review.

    1 min readAI

  77. Another INNOVIT - Italian Innovation and Culture Hub startup mentorship eventAnother INNOVIT - Italian Innovation and Culture Hub startup mentorship event in the books. Always refreshing to work with non-tech founders.

    1 min readStartups

  78. For decades we've shipped frozen interfaces where every pixel was decidedFor decades we've shipped frozen interfaces where every pixel was decided by a designer years before you opened the app.

    1 min readAI

  79. We spend endless hours agonizing over marketing, tweaking brand colorsWe spend endless hours agonizing over marketing, tweaking brand colors, and putting our logos on every square inch of what we build.

    1 min readProduct

  80. AI is being discussed as if the economy is mostly software, contentAI is being discussed as if the economy is mostly software, content, and knowledge work. That framing holds if your world is screens, documents, and APIs.

    2 min readAI

  81. Vibe-coded apps usually deliver on the big features but they bleed outVibe-coded apps usually deliver on the big features but they bleed out on the small promises.

    1 min readEngineering

  82. One careless download can cascade across companiesOne careless download can cascade across companies. In February 2026, an employee at Context.ai installed a Roblox cheat.Hidden inside: Lumma Stealer malware.

    1 min readAI

  83. Moats are retention tools sold as growth strategyMoats are retention tools sold as growth strategy. Switching costs and data gravity make leaving expensive.

    1 min readAI

  84. Speed is no longer a differentiator once the customer has to finish the jobSpeed is no longer a differentiator once the customer has to finish the job. What I see inside companies is a familiar sequencing mistake: teams treat an...

    1 min readProduct

  85. Anthropic has figured out that fear sellsAnthropic has figured out that fear sells. They frame their releases in existential terms, leaning into “this could be dangerous” narratives.

    1 min readAI

  86. In AI work, volume is not vanityIn AI work, volume is not vanity. It is a control surface. Most organizations treat quantity as a cost center.

    1 min readAI

  87. If your strategy requires you to fight for every dealIf your strategy requires you to fight for every deal, you do not have a strategy, you have a stamina test.

    1 min readEngineering

  88. The BNP Paribas Indian Wells tennis tournament is my favorite and I attendThe BNP Paribas Indian Wells tennis tournament is my favorite and I attend every year. High-percentage tennis is what coaches teach when they want you to...

    2 min readProduct

  89. People often ask if you still need to be in San Francisco to build somethingPeople often ask if you still need to be in San Francisco to build something meaningful in tech. For a while, it looked like the answer might be no.

    2 min readAI

  90. I get the math, but the part I’d pressure test is the framingI get the math, but the part I’d pressure test is the framing: optimizing a kid’s life around “retiring” at 59½ can accidentally anchor decisions toward...

    1 min readStartups

  91. The highest paid AI roles will belong to the people who can makeThe highest paid AI roles will belong to the people who can make the organization change its behavior, not the people who can make the model smarter.

    1 min readAI

  92. Life with ClaudeLife with Claude. Discuss on LinkedIn

    1 min readAI

  93. Apple’s “Apple Business” launch is not a productivity-suite storyApple’s “Apple Business” launch is not a productivity-suite story. It’s a control-plane story.

    1 min readMobile

  94. The AI job everyone is talking about does not existThe AI job everyone is talking about does not exist. “Prompt engineer” was a temporary phase.

    2 min readAI

  95. White House Unveils National AI Policy FrameworkWhite House Unveils National AI Policy Framework Speed first, regulation later. Discuss on LinkedIn

    1 min readAI

  96. When a company tells me “AI is helping people grieve, learn, get careWhen a company tells me “AI is helping people grieve, learn, get care, access services”, I believe them.

    1 min readAI

  97. Anthropic just changed how AI coding tools will be usedAnthropic just changed how AI coding tools will be used. They introduced Claude Code channels.

    1 min readAI

  98. Most AI risk conversations are framed like this:Most AI risk conversations are framed like this: “There is the value, and then there are the harms.” That framing is comforting.

    2 min readAI

  99. Most AI conversations inside companies start with: “We need to be faster.”Most AI conversations inside companies start with: “We need to be faster.” Anthropic ran 81,000 interviews and kept hearing the same pattern: people begin...

    1 min readAI

  100. From a conversation with Gokul RajaramFrom a conversation with Gokul Rajaram. Discuss on LinkedIn

    1 min readBusiness

  101. Apple is cookingApple is cooking! 😂 90min from submission to approval. Discuss on LinkedIn

    1 min readMobile

  102. Most operators say they want teams that “understand the system.”Most operators say they want teams that “understand the system.” What they consistently reward is speed of response inside it.

    1 min readAI

  103. Most developers focus on the U.S. and Europe.Most developers focus on the U.S. and Europe. But the fastest-growing iOS markets are elsewhere. I wrote a short piece on why emerging markets are often the...

    1 min readBusiness

  104. Serial founders talk about "batting average" like the goal is to never strikeSerial founders talk about "batting average" like the goal is to never strike out. That is a misunderstanding of the game they are actually playing.

    1 min readAI

  105. Everyone tells the ATM story wrong.Everyone tells the ATM story wrong. They treat labor substitution like a task list: automate the cash withdrawal, the teller disappears.

    1 min readAI

  106. With AI agents, complexity stops being a tax and starts becoming a moatWith AI agents, complexity stops being a tax and starts becoming a moat. Most leaders still treat complexity like something to "simplify away": fewer...

    2 min readAI

  107. The early labor signal from AI is not layoffs.The early labor signal from AI is not layoffs. It is the hiring freeze you do not call a freeze.

    2 min readAI

  108. Most SaaS is designed to be chosen by a person who is slightly unsure.Most SaaS is designed to be chosen by a person who is slightly unsure. So we obsess over UX polish, onboarding flows, "time to value", and the story you can...

    2 min readAI

  109. AI Is Commoditizing Intelligence.AI Is Commoditizing Intelligence. Value Is Moving Elsewhere. AI capability is becoming widely accessible.

    2 min readAI

  110. AI isn't making "development" more valuable.AI isn't making "development" more valuable. It's making raw output less scarce. When a studio can ship 3x the code with the same headcount, the client's...

    1 min readAI

  111. The #SaaSpocalypse is a great narrative because it takes a real shift and turnsThe #SaaSpocalypse is a great narrative because it takes a real shift and turns it into a clean conclusion.

    1 min readAI

  112. "Digital transformation" is not disruption."Digital transformation" is not disruption. Buying software does not change your market position. It just changes what you pay for, and who you depend on.

    1 min readAI

  113. AI isn't replacing workers.AI isn't replacing workers. It's replacing what work even means. Most people still frame AI as productivity software, or task-completing agents.

    1 min readAI

  114. Sometimes the reason the category is crowded is the same reason it will notSometimes the reason the category is crowded is the same reason it will not support a durable business.

    1 min readAI

  115. AI will replace the parts of consulting that look like consulting.AI will replace the parts of consulting that look like consulting. So why do companies still pay for the rest?

    1 min readAI

  116. Your data moat gets weaker the moment interpretation gets cheap.Your data moat gets weaker the moment interpretation gets cheap. So what happens when your "advantage" was just owning the spreadsheet?

    2 min readAI

  117. The biggest impact of LLMs is not replacing software.The biggest impact of LLMs is not replacing software. It is turning "unwritten work" into something a business can actually run.

    1 min readAI

  118. AI will commoditize the part of software your CFO obsesses over.AI will commoditize the part of software your CFO obsesses over. So why are teams still choosing vendors based on features and day rates?

    1 min readAI

  119. Tokens are not the bottleneck. Humans are.Tokens are not the bottleneck. What happens to "AI adoption" when nobody has to ask? Most companies treat AI like a new UI layer.

    1 min readAI

  120. Law is just the first industry to break (thanks to Harvey and Legora).Law is just the first industry to break (thanks to Harvey and Legora). Every knowledge job is next.

    2 min readAI

  121. Most SaaS companies won't die because of competitionMost SaaS companies won't die because of competition. They'll die because their pricing model stops making sense.

    2 min readAI

  122. AI is not blocked by intelligence. It's blocked by org charts.AI is not blocked by intelligence. It's blocked by org charts. Everyone thinks AI adoption is about better models.

    1 min readAI

  123. AI makes products look simpler while making them harder to run.AI makes products look simpler while making them harder to run. When a UI collapses into a prompt box, leaders assume complexity disappeared.

    1 min readAI

  124. Data advantage is no longer about owning data.Data advantage is no longer about owning data. If data is truly the moat, why does everyone also expect it to be portable?

    1 min readAI

  125. The real scarcity is judgment, not execution.The real scarcity is judgment, not execution. If building is cheap now, why do so many digital programs get slower?

    1 min readAI

  126. Customer Support: Growth Lever or Labor Sponge?Most operators hear the Zappos Family of Companies story and take the safe lesson: invest in people, create loyalty, win on experience.

    2 min readAI

  127. How Companies Will Hire Based on AI UsageSmart companies will hire you based on "how" you use AI. McKinsey & Company started piloting an interview where candidates use its internal AI tool, Lilli...

    1 min readAI

  128. How a 10% Credit Card APR Cap Could Raise Your Growth CostsA 10% cap on credit card APR can raise your growth costs. If the rate goes down, why would acquisition get harder?

    1 min readAI

  129. GEO: The New Frontier Beyond SEO and AEOGEO is not a marketing tactic. It is an operations problem. Who owns the truth when the customer never clicks?

    2 min readAI

  130. Why Education No Longer Guarantees EmploymentEducational institutions are no longer a reliable path to employment. It is a bet that companies may never need to honor.

    2 min readAI

  131. Drone Delivery Is Easy. Getting Picked by AI Is Hard.Drone delivery is the easy part. Getting picked by the AI that starts the shopping journey is harder.

    1 min readAI

  132. Why Agentic Checkout Will Break Your Business RulesAgentic checkout will not break because the AI is wrong. It will break because your business rules are.

    1 min readAI

  133. Stop Wasting $100K on Dev Shops Without StrategyWant to throw away $100k? just tell a dev shop to build your idea. 😂 Most founders rush to hire a developer before they have a strategy.

    2 min readAI

  134. The Ugliest Process Is Usually Keeping You AliveThe ugliest process in a company is usually the one keeping it alive. Before you delete it, do you know what risk it was built to absorb?

    1 min readAI

  135. AI Output Quality Mirrors Your Operating DisciplineThe quality of your AI output is a mirror of your operating discipline. Are you using a model, or are you outsourcing requirements?

    1 min readAI

  136. Most Pricing Problems Are Discovery ProblemsMost pricing problems are really discovery problems. “Worth” is not something you carry into the room.

    1 min readAI

  137. AI in Customer Support, Ecommerce, and LeadershipFor years, my default advice was “go hybrid first”. When a founder had 50k, a deadline, and no mobile team, Cordova was a rational way to ship something...

    1 min readAI

  138. Your AI Strategy Will Break With the Next Model ReleaseYour AI “strategy” will look brilliant right up until the next model release breaks it. I keep seeing operators in logistics, insurance, and industrial...

    1 min readAI

  139. Why Remote Work Fails for Sense-MakingThe project is “on track” for six weeks, then suddenly you cannot explain what you are building to a customer.

    1 min readAI

  140. Why Early-Stage Founders Don't Need a Full-Time CTOMost founders do not fail because they cannot build. They fail because they buy the wrong build.

    2 min readAI

  141. Why Most GenAI Rollouts FailMost GenAI rollouts fail for the same reason the first ML projects failed. Everyone budgeted for a subscription and got a systems integration.

    1 min readAI

  142. Enterprise and Data with AIWe used to ship POS and loyalty updates in 7-10 days. Then we added a “lightweight” process and it became 6 weeks.

    1 min readAI

  143. AI in Product, Delivery, and DataWe used to blame our “slow” team for missing the loyalty app launch. Then we added two more squads and missed by another quarter.

    1 min readAI

  144. AI in Customer Support, Product, and LeadershipI used to applaud teams for “taking risks.” Then I watched the same launch fail three times with three different names.

    1 min readAI

  145. AI and Customer SupportI used to think senior engineers earned trust by always having an answer. Then I watched a launch slip because nobody wanted to say “I do not know.” At a...

    1 min readAI

  146. AI, Product, and DeliveryWe never tracked “delivery speed” until the CEO asked for one number. Two sprints later, we were “faster” and member complaints doubled.

    1 min readAI

  147. Strategy and Enterprise with AIAI is replaying the SaaS cycle in reverse. “ChatGPT for everything” is the easy part. A mid-market insurer rolled out a generic AI chat tool to help...

    1 min readAI

  148. This year reinforced something I have seen over and over across productsThis year reinforced something I have seen over and over across products, companies, and founders. Effort is rarely the constraint.

    1 min readAI

  149. AI in Automation, Ecommerce, and DeliveryMost grocery apps fail for a boring reason. Nobody agreed on the one number it should move. Margins are thin and shoppers bounce fast.

    1 min readAI

  150. Customer Support and Strategy with AII asked AI to tell me about how I use AI: Here's what it had to say: "You use AI primarily as a leverage tool for thinking, not as a substitute for it...

    1 min readAI

2025

94 posts
  1. Customer Support and Enterprise with AII wonder how much of what we call “finance best practice” is really just coping with banks being closed. Your month-end close is a map of bank cutoffs.

    1 min readAI

  2. AI, Customer, and PricingYour next SaaS renewal should feel harder than last year. That is not procurement being annoying. It is the math changing.

    1 min readAI

  3. AI and StrategyMost big consulting engagements are not bought for insight. They are bought for liability transfer.

    1 min readAI

  4. Is there a way to block all trash posts with “comment xxx to get full yyy”?Asking for a friend. 👀 Discuss on LinkedIn

    1 min readBusiness

  5. Operations and Data with AIMost grocery stores do not need a data center to decide if a shelf is empty. That is why NPUs are showing up in checkout lanes, handhelds, cameras, and...

    1 min readAI

  6. AI, Customer, and EnterpriseMost bank AI bans are really policy statements, not behavior changes. The work just goes underground.

    1 min readAI

  7. AI, Customer, and DeliveryDomain knowledge is the only moat. AI can write the code, but it cannot own the mess it creates.

    1 min readAI

  8. AI, Growth, and DeliveryThe Netflix lawsuit gets one thing wrong right from the start: it’s fighting a market that no longer exists.

    2 min readAI

  9. Customer Support and Automation with AIRecent discussions around AI in radiology often suggest that automation will replace human expertise.

    1 min readAI

  10. AI, Engineering, and StartupsWe talk about AI as if it’s a contest of smarter models. What’s actually unfolding is a clash of long-standing institutional playbooks...

    2 min readAI

  11. AI in Operations, Growth, and EngineeringEveryone keeps saying content is king. – Paramount lacks scale. – The Walt Disney Company struggles with identity.

    2 min readAI

  12. Fast cheap good. Pick two?Fast cheap good. Pick two? That line should have retired with flip phones. I help founders shape the strategy, the roadmap, and the calls that decide...

    1 min readAI

  13. AI in Engineering, Delivery, and DataAI assisted coding isn't a "boost" anymore. It is the default way devs ship software (or your team falls behind).

    1 min readAI

  14. AI and EnterpriseMost SaaS companies are protecting the wrong moat. We’ve spent years thinking features, UI polish, and enterprise checkboxes keep competitors at bay.

    1 min readAI

  15. AI in Automation, Strategy, and DataThe smartest way to use Polymarket right now isn't harder research. It's automated research. Most people try to keep up with Polymarket manually.

    2 min readAI

  16. AI in Customer Support, Education, and DataOpenAI has just launched "ChatGPT for Teachers," a new tool specifically designed for K-12 educators. This initiative is free for U.S.

    1 min readAI

  17. AI in Strategy, Product, and DataHad a great session with Ariel Michaeli of Appfigures on ASO. Here are some nuggets (best for last 😜): Screenshots that convert - Show real UI immediately...

    2 min readAI

  18. AI in Strategy, Product, and StartupsMeanwhile in tennis world, something wild is happening. ATP world #1000 is closer to #3 than #3 is to #2. That is what winner-take-most looks like.

    1 min readAI

  19. If your advisor only knows your industryIf your advisor only knows your industry, you are paying for the same blind spots. The best second opinion often comes from outside the room.

    1 min readAI

  20. When Charles Schwab launched discount brokerage in the 1970sWhen Charles Schwab launched discount brokerage in the 1970s, Wall Street called it dangerous.

    1 min readAI

  21. Strategy and Data with AIToday I tried something that sounded impossible: building a web app with zero application code. No routes, no controllers, no logic files...

    2 min readAI

  22. AI in Strategy, Leadership, and StartupsMost people think taste is innate. In reality, it's a skill you earn through tinkering. You don't develop good taste by consuming more content.

    1 min readAI

  23. AI in Operations, Product, and EngineeringYou've probably heard the hype: "AI agents will replace entire workflows." Yet less than 5% of them actually work in production.

    1 min readAI

  24. The 80% agent is better than the 100% agent.The 80% agent is better than the 100% agent. A 100% autonomous agent that makes a mistake 2% of the time is terrifying.

    1 min readBusiness

  25. AI, Operations, and StartupsEveryone in tech talks about AI agents for crypto trading, content generation, or writing code.

    2 min readAI

  26. AI in Strategy, Engineering, and HiringIf your team always defaults to React, your business is silently paying a tax on performance, innovation, and opportunity.

    2 min readAI

  27. AI in Automation, Strategy, and ProductChasing full autonomy for AI Agents is wrong. They need to be the scaffolding human expertise.

    1 min readAI

  28. AI in Strategy, Product, and EcommerceMost ecommerce leaders are still optimizing (and spending) for Google search. But your next "customer" won't even be human, it will be an AI agent.

    1 min readAI

  29. Engineering and Digital Transformation with AIThat's not a problem, that's a mess. A problem has a clear cause and solution. A mess is interconnected, dynamic, and resists being solved in isolation.

    1 min readAI

  30. Customer, Growth, and StrategyMost companies get stuck chasing the middle. They try to balance cost and experience... and end up delivering neither well.

    1 min readBusiness

  31. Want to go viral on LinkedIn right now?It's extremely easy. All you have to do is... Declare that you either DO or DO NOT use AI in your writing, then proclaim the other side is wrong.

    1 min readAI

  32. Growth, Strategy, and ProductMost product teams say they are data-driven. The best ones know that data should not drive the design. Taste builds products that stand out.

    1 min readBusiness

  33. "Let's just get the requirements right the first time." That's how millions"Let's just get the requirements right the first time." That's how millions are wasted. Most people can't describe what they want in a way that translates...

    1 min readAI

  34. Most dev teams obsess over "doing it rightMost dev teams obsess over "doing it right." But "done fast" often beats "done perfect." Customers aren't buying clean code or test coverage.

    1 min readAI

  35. AI, Strategy, and Engineering"Clean code" is not self-documenting when it comes to why it was written that way. Most software documentation explains what the code does.

    1 min readAI

  36. Customer Support and Engineering with AI😱 I gave Claude access to my inbox. Here's what it had to say... Your communication style signals: "I respect your time, I understand the real issues, and...

    2 min readAI

  37. AI in Product, Sales, and DeliveryFive figures on "dev work" and nothing to show. 🤦‍♂️ • A boutique gym chain spent 6 months and $72k on mockups and 'exploratory' dev sprints • No TestFlight...

    1 min readAI

  38. AI doesn't raise the ceiling, it raises the floorAI doesn't raise the ceiling, it raises the floor. It accelerates baseline capabilities across your team. A sales director can prep tailored pitches in minutes.

    1 min readAI

  39. AI won't crush your industryAI won't crush your industry. It will magnify the flaw you already ignore. Most leaders still debate whether AI is disruptive or sustaining.

    1 min readAI

  40. I’ve been in italy the whole month and I’m used to “small” two-lane freewaysI’ve been in italy the whole month and I’m used to “small” two-lane freeways but something occurred to me while driving.

    1 min readBusiness

  41. AI in Customer Support, Strategy, and EngineeringCEOs beg for a magic AI prompt. A chef can’t cook without ingredients; your model can’t think without context.

    1 min readAI

  42. Beauty is the outcome of coherence, proportion,Beauty is not arbitrary. Design is not how it looks. It's how it works. Too many companies hear "design matters" and start decorating.

    1 min readAI

  43. AI in Product, Ecommerce, and DataYour app doesn’t need more features. It needs fewer while delivering ROI faster. Across 50+ product audits, I see teams sink 60% of budget into functions...

    1 min readAI

  44. Burger King spent like a League Two club and got a Champions League returnBurger King spent like a League Two club and got a Champions League return. 1.2B impressions from a team nobody can find on a map.

    1 min readAI

  45. AI in Strategy, Startups, and DataAI used to build startups from scratch. Now it is buying the ones you forgot existed. VCs like Khosla Ventures are rolling up call centers, accounting...

    1 min readAI

  46. Your favorite AI unicorn just tripped over its own numbersYour favorite AI unicorn just tripped over its own numbers. Builder.ai went from $1.3B headline valuation to insolvency in 72 hours.

    1 min readAI

  47. Would you leave the lights off when customers walk in?Your UI is your storefront. Would you leave the lights off when customers walk in? We started with static pages, then crammed them onto phones, then...

    1 min readAI

  48. The hashtag#EU just dropped a preview of its 2025–26 Startup & Scaleup StrategyThe hashtag#EU just dropped a preview of its 2025–26 Startup & Scaleup Strategy. Some parts are solid. Others felt already old.

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2024

2 posts
  1. Why a Fractional CTO Might Be Exactly What Your Business NeedsThe Challenge: Managing Technology Without a CTO Many businesses face the same dilemma: technology is critical to their growth, but hiring a full-time Chief...

    5 min readLeadership

2023

23 posts
  1. When it comes to managing investments and capitalWhen it comes to managing investments and capital, several financial firms play vital roles in the world of finance.

    5 min readBusiness

2015

7 posts
  1. Mobile is differentMobile requires new skills and new ways of thinking. Mobile is different. But it also can be learned if you make the right investment in your people and...

    1 min readMobile

2013

77 posts
  1. Apple App Store changed the business world foreverIn raw numbers, the Apple App Store's reach is undeniable, with more than 50 billion downloads and about 900,000 apps in total.

    5 min readMobile

  2. Mobile application strategy for big brandsIt's no longer enough for brands to just have an app (or a suite of apps) and promote it through traditional channels.

    5 min readGrowth

  3. When should an enterprise application become a mobile app?The short answer is in 99% of cases as soon as possible. However, if you still need elements to justify the time and money investment, you should keep in...

    5 min readBusiness

2012

111 posts
  1. Common Angel Investment TermsThere are only a handful of common angel investment terms that you should be familiar with before you go out looking for capital.

    4 min readStartups

  2. Apple Custom B2B Apps on the AppStore explainedAs an extension to the volume purchase program, businesses can also have custom apps built by third-party developers.

    3 min readMobile