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.

26 posts in Buying Software

2026

267 posts
  1. Who is liable when a business's AI agent causes harm?When your AI agent causes harm, your business is usually the one exposed. What the OpenAI and Hugging Face breach shows, what vendor terms say, and five controls to set first.

    7 min readBuying Software

  2. Should my business lock into one AI vendor while prices keep falling?Anthropic and OpenAI cut frontier AI prices by 20% to 50% in one week. Why owners should keep AI contracts short, stay model-agnostic, and re-test every year.

    7 min readBuying Software

  3. You cannot model a software build on the vendor's estimateA fractional CFO asked me how to model a software build in the plan when the only number available is the vendor's estimate.

    1 min readBuying Software

  4. When is an AI API wrapper enough, and when do you need more?An API wrapper around ChatGPT or Claude is enough for generic, reviewed, low-risk work. You need more once the AI speaks for your company, uses your data, or is the product.

    8 min readBuying Software

  5. What are the red flags in a software development proposal?20 red flags in a software or app development proposal, grouped by pricing, scope, ownership, quality, and vendor behavior, each with the exact question to ask the vendor.

    10 min readBuying Software

  6. 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

  7. 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

  8. 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

  9. What to know before signing a three-year SaaS contractA three-year SaaS contract is on the desk with a discount for committing. Before signing, this is what I would want to know.

    2 min readBuying Software

  10. 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

  11. 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

  12. 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

  13. 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

  14. 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

  15. 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

  16. NVIDIA buying Hugging Face could make open AI depend on a single vendorNVIDIA buying Hugging Face could make “open AI” more dependent on a single vendor.Reports put the potential deal around $13 billion.

    1 min readBuying Software

  17. Build custom software or buy off the shelf?Most owners who think they need custom software need configuration instead. Here is how to tell which side of the build-vs-buy line you are on before you spend.

    6 min readBuying Software

  18. 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

  19. 10 questions to ask before hiring a software agencyAsk these ten questions before you sign with a software development agency, with what good and bad answers sound like on code ownership, team, pricing, QA, and exit.

    11 min readBuying Software

  20. 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

2013

77 posts
  1. What to look for in an iOS developer (with checklist and answers)Initially one might think that a developer is purely someone who needs to put some code together therefore not much can go wrong...

    4 min readBuying Software

2012

111 posts
  1. How much does it cost to develop an app?In the past two years, the app market has exploded. In under 9 months the Apple store reported over a billion downloads, and then doubled that number in...

    11 min readBuying Software

  2. Why I Won't Sign Your NDAI recently came across a very interesting article regarding NDAs. I was never a fan, mainly due to the many writings on how pure original ideas don't exist...

    2 min readBuying Software

  3. Evernote: New Legal Page and Changes to Contracts Coming SoonEvernote will soon be updating their ToS and Privacy contracts with users. Here is the full note the sent out: We spend a lot of our time improving our...

    6 min readBuying Software

  4. New iOS Paid Applications Contract Amendment - Changes by AppleThis morning when I logged in iTunes Connect to check some routine "stuff", I was greeted with a message from Apple.

    2 min readBuying Software

  5. Legal issues with APIs and their useThese days there is a lot of rumors going on regarding Craigslist and how they seem to be tightening the grip on other services that appear to be using...

    1 min readBuying Software