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.

What’s on Your Mind? LinkedIn

Blog

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

118 posts in Leadership

2026

267 posts
  1. For a hardware company, the most expensive screen is the pairing screenFor a hardware company, the most expensive screen in the product is the pairing screen. The device is designed, tooled, certified and boxed.

    1 min readEngineering

  2. Before hiring an AI consultancy, find the part that actually needs AIBefore hiring an AI consultancy, work out which part of the problem actually requires AI. It is usually smaller than the proposal.

    1 min readAI

  3. Fractional CTO vs technical advisor vs full-time CTO: which do you need?Fractional CTO, independent technical advisor, or full-time CTO: what each role does, what each costs in 2026, and how a non-technical owner picks the right one.

    6 min readLeadership

  4. 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

  5. Technology due diligence should not happen after you have decided what you wantTechnology due diligence should not happen after you have decided what you want to do. By then it is not diligence.

    2 min readProduct

  6. 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

  7. 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

  8. 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

  9. 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

  10. Your development agency says the project is 80% completeYour development agency says the project is 80% complete. Before you feel relieved, ask what is being measured.

    2 min readBuying Software

  11. Software projects look green right until they failSoftware projects look green right until they fail because status reports measure activity, and activity is always available.

    1 min readEngineering

  12. 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

  13. Your software project is six months lateYour software project is six months late. The options are fix it, replace the team, cut scope, or kill it, and every person advising you has a stake in one...

    1 min readEngineering

  14. AI made software dramatically cheaper to createAI made software dramatically cheaper to create. It did not make bad software decisions cheaper. If anything, it made them more common.

    1 min readAI

  15. The prototype took three weeksThe prototype took three weeks. The production system is quoted at nine months. Owners read those two numbers and conclude someone is lying.

    2 min readAI

  16. 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

  17. Build versus buy is an incomplete questionBuild versus buy is an incomplete question. There is a third option, and it is the cheapest one on the table: change the process so you need neither.

    1 min readBuying Software

  18. 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

  19. 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

  20. 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

  21. 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

  22. Three proposals for the same project: $80k, $240k and $600kThree proposals for the same project: $80k, $240k and $600k. They are for the same project the way three quotes to "fix the roof" are for the same roof.

    2 min readBuying Software

  23. Years of internal operational mess are about to have a market valueCompanies are about to discover that years of internal operational mess have a market value.

    1 min readAI

  24. A custom domain can hide the builder from your customersA custom domain can hide the builder from your customers.It cannot hide it from the internet.

    1 min readEngineering

  25. It took me less than an hour to reach 200,000 people's private dataIt took me less than an hour to reach 200,000 people's private data (including mine) in an app I don't own. No login of any kind.

    3 min readStartups

  26. 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

  27. "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

  28. 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

  29. 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

  30. How much does custom software cost? A 2026 reality checkCustom software runs $25k to $250k for most owner projects. Here is what drives the price, why bids vary 10x, and how to avoid overpaying.

    6 min readBuying Software

  31. Rules are often an admission that incentives were never designedRules are often an admission that incentives were never designed. A team makes documentation mandatory. Compliance goes up for a month.

    1 min readProduct

  32. Owning your own e-commerce store has become cheaper than earning attentionOwning your own e-commerce store has become cheaper than earning attention inside someone else’s marketplace.

    1 min readAI

  33. Entry-level jobs are becoming a less reliable way to predict future headcountEntry-level jobs are becoming a less reliable way to predict future headcount. The common assumption is simple: if AI can do part of the work, companies...

    2 min readAI

  34. People are confusing "can build" with "should own"A lot of people are confusing “can build” with “should own.” The argument goes like this: AI makes software development dramatically cheaper, therefore...

    2 min readAI

  35. 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

  36. UI is the worst thing technologists builtUI is the worst thing technologists built. Software companies organize themselves around screens.

    1 min readAI

  37. 120 employees, 40 experimenting with AI, all trapped in private tabs120 employees.40 experimenting.And it’s all trapped in private tabs. This isn’t an AI problem. It’s a knowledge management problem.

    1 min readAI

  38. Most firms are optimizing the wrong variableMost firms are optimizing the wrong variable. They’re treating AI like a cheaper labor substitute: reduce cost, automate steps, accelerate workflows.

    1 min readAI

  39. 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

  40. “10x engineering” is a comforting story because it gives you a single lever“10x engineering” is a comforting story because it gives you a single lever: ship more code.

    2 min readAI

  41. 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

  42. I grew up in ItalyI grew up in Italy. I live in the US now. Same human problem, two opposite answers, and I've watched both up close.

    2 min readAI

  43. 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

  44. 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

  45. 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

  46. Agentic code is free like a baby goatAgentic code is free like a baby goat.The first day is the cheapest day you will ever have with it.

    1 min readAI

  47. 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

  48. Freezing junior engineering hiring is not a cost moveFreezing junior engineering hiring is not a cost move, it is an organizational risk decision disguised as efficiency.

    1 min readAI

  49. AI cost conversations usually start at the model and end at pricingAI cost conversations usually start at the model and end at pricing. That is the least relevant part of the system.

    2 min readAI

  50. 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

  51. 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

  52. 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

  53. Engineering teams that went heaviest on AI coding tools are now the onesEngineering teams that went heaviest on AI coding tools are now the ones struggling most with stability.

    1 min readAI

  54. Agile fails when it optimizes the speed of building instead of the speedAgile fails when it optimizes the speed of building instead of the speed of learning. Inside most companies, the backlog becomes a proxy for certainty.

    1 min readPricing

  55. Most people do not want your appMost people do not want your app. They want the outcome. The app is just the path. Yet many companies design the experience as if the download itself were...

    2 min readMobile

  56. 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

  57. Most “disruption” is just a better interface on top of the same systemMost “disruption” is just a better interface on top of the same system. Real disruption is when the incumbent’s operating model becomes incompatible with...

    1 min readAI

  58. 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

  59. If your ARPU did not go up by at least 50%If your ARPU did not go up by at least 50%, your new AI component is just a feature. Inside most companies, AI lands where the org can absorb it: a workflow...

    1 min readAI

  60. 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

  61. One of the stranger patterns in AI adoption is emotional, not technicalOne of the stranger patterns in AI adoption is emotional, not technical. Lower and middle-income regions often read AI as upside.Wealthier regions read it...

    1 min readAI

  62. 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

  63. Most leaders are mispricing AIMost leaders are mispricing AI. They’re arguing about “intelligence” while the defensible value is a service bundle humans can’t deliver at scale: patience...

    1 min readAI

  64. Racing used to punish mediocrityRacing used to punish mediocrity. With a combustion engine, the car was a system you had to actively manage:gear selection, power band, traction, cooling...

    2 min readAI

  65. 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

  66. 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

  67. "Agents" without an orchestrator are just new tools with a chat UI."Agents" without an orchestrator are just new tools with a chat UI. In most non-tech companies, the hard part is not getting a model to take an action.

    1 min readAI

  68. AI does move fast.AI does move fast. But the thing that leaves senior managers behind is not the pace of models. It is the pace of decision loops.

    1 min readAI

  69. 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

  70. 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

  71. AI is going to create job categories that sound fake until you need one tomorrowAI is going to create job categories that sound fake until you need one tomorrow. Not because the tools get better.

    2 min readAI

  72. 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

  73. 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

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

    2 min readAI

  75. Most organizations are thinking about AI backwards.Most organizations are thinking about AI backwards. They start with, "Where can we add AI?" and that almost always produces the same roadmap: assistants...

    2 min readAI

  76. 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

  77. 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

  78. "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

  79. 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

  80. 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

  81. The internet did not kill publishing. It broke the unit of value.The internet did not kill publishing. It broke the unit of value. If code generation gets "free", what exactly will SaaS customers still be paying for?

    1 min readAI

  82. 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

  83. 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

  84. 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

  85. AI in Engineering, Leadership, and SalesClarity is not something you find before you move. It is something you earn by moving. So why do we keep waiting for a cleaner vision before we act?

    1 min readAI

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

    1 min readAI

  87. 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

  88. 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

  89. AI, Customer, and HiringI never watched a founder hand over their gut to a dashboard. Then the dashboard started running the company.

    1 min readAI

  90. 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

  91. 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

  92. AI in Engineering, Hiring, and DataI went home to Italy for Christmas. On my flight back to SF, I watched Jersey Boys and it reminded me that talent does not protect you from a bad deal.

    1 min readAI

  93. 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

  94. The 10x productivity claim with AI Is still misThe 10x productivity claim with AI Is still misleading but in the way you're thinking. Saying AI makes your devs "10x engineers" hides the real variable...

    2 min readAI

2025

94 posts
  1. corporate transformationsMost corporate transformations fail for a simple reason: they’re a substitute for thinking, not a product of it.

    2 min readAI

  2. 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

  3. AI in Growth, Engineering, and LeadershipMost CEOs are optimizing for a world that no longer exists. Progress isn’t driven by resources, talent, or even technology.

    2 min readAI

  4. AI and Hiring"AI Can Technically Perform 12% of US Labor Market's Wage Value" via Massachusetts Institute of Technology Most leaders point AI at dev teams.

    1 min readAI

  5. 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

  6. AI and LeadershipA CEO plays word games to influence market bets and it shines light on the vulnerability of betting platforms.

    1 min readAI

  7. 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

  8. 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

  9. 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

  10. 💥 LAST MINUTE Workshop for Founders💥 LAST MINUTE Workshop for Founders! I got a cancellation for this Monday morning (Pacific Time). It's a 2-hour workshop with me.

    1 min readAI

  11. Most founders don't run out of ideasMost founders don't run out of ideas. They run out of time, money, and patience… …because they built too much of the wrong thing.

    1 min readAI

  12. "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

  13. 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

  14. It's not the code that kills your vision, it's the unclear decisionsIt's not the code that kills your vision, it's the unclear decisions, the slipping timeline, and the invoices you don't understand.

    2 min readAI

  15. 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

  16. AI in Automation, Hiring, and EducationWe accidentally deleted the entry-level job. And we haven't replaced it with anything better.

    2 min readAI

  17. Now is the time to (re)buildNow is the time to (re)build. Most companies overpay to rebuild digital products because they wait too long.

    1 min readAI

  18. 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

  19. I'm increasingly hearing about these frustrations from Startup Founders whoI'm increasingly hearing about these frustrations from Startup Founders who reach out to me. They've tried to hack an MVP with AI tools.

    1 min readAI

  20. 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.

    1 min readAI

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. Chief of StaffIn the dynamic world of technology and business, the role of a Chief of Staff is akin to being the conductor of an orchestra, orchestrating harmonious...

    3 min readLeadership

2013

77 posts
  1. How to hire a freelancerTL;DR you need to have experience and knowledge in order to weave-out the bad candidates...

    6 min readLeadership

2012

111 posts
  1. Approaching the iPhone App Business: "Se lo fai, falloI love making apps for early stage startups. Many of my clients are big companies that are scared to fall behind and therefore just want an iPhone app.

    3 min readMobile