David OConnell

Author: David O’Connell

  • The Hamster Wheel Test

    The Hamster Wheel Test

    Eighteen months ago the wow was a picture. Type a sentence, watch software paint you an image that would have taken a decent illustrator an afternoon, and the whole internet performed the same double-take at the same time. That was the trick. Impressive, a little uncanny, mostly a party favour.

    That is not what is happening now. Now I hand a piece of work to something that plans it, executes it, checks its own output, and only comes back when there’s a decision that actually needs me. The distance between “AI made a nice picture” and “AI ran a client’s Tuesday” has been covered in about a year and a half, and most small business owners I talk to are still catching their breath from the first part.

    Which raises the obvious question, because it should: are we actually getting somewhere, or are we just running faster on the same wheel?

    I can only answer for my own patch of ground, and there the answer is genuinely yes. I run this as a one-man operation, and on certain categories of work I am moving through five to ten times what I could a couple of years ago. Not by working five to ten times harder — by handing off the parts of the job that were never the valuable part. Running a fix past three plausible causes before I commit to one. Chasing down an obscure error that would once have meant an evening lost to forum posts and stack traces. Querying a client’s database for the answer to a question they asked me on a call twenty minutes earlier, while we’re still on the call.

    None of that is the work I’m actually paid for. It’s the toll you pay to get to the work you’re paid for. And that toll has gotten a lot cheaper.

    Two examples

    A client sells through a vendor catalogue — hundreds of products, updated constantly, and a brand voice that needs to hold across every one of them. The old way of turning that into a week’s worth of social content meant someone sitting down, product by product, writing copy and pulling images and matching a style guide by hand. I built a workflow that takes the catalogue feed straight through to a hundred branded, on-voice posts a week, ready to schedule. That’s not a person’s job anymore. It was never a job anyone enjoyed doing — it was a job someone tolerated because the alternative was an empty content calendar.

    Second: email triage. Every small business owner I know loses part of every morning to a spam problem that keeps evolving faster than the tools built to stop it. I set up an agent that reads intent rather than just keywords, and it’s catching what static filters miss — the plausible-looking invoice, the fake vendor follow-up, the thing that would once have needed a human eye and a human minute to delete. That minute, multiplied by every message, every day, adds up to something worth having back.

    Where the attention goes

    What both of those have in common is that they’re not really about output. Nobody’s business gets better because it posts more, or answers email faster, in the abstract. What they’re actually about is where the owner’s attention goes. Every hour that used to disappear into the catalogue or the inbox is an hour that can now go toward the customer relationship, the pricing decision, the thing only the owner can actually judge. That’s the real trade being made, and it’s a good one when it happens on purpose.

    When it happens on purpose

    When it happens on purpose is the part worth sitting with, though. The same surveys showing most small businesses reporting real productivity gains this year also show a third of the tools they buy sitting unused within three months. Adopted out of nerves, not need. Kept because cancelling feels like admitting defeat. That’s the wheel — not AI itself, but the reflex to reach for a new tool every time a headline suggests you’re falling behind, without ever asking what specific problem you were trying to solve when you picked it up.

    I don’t think the honest answer is that we’re all hamsters, or that we’ve all found the accelerant for real growth. I think both are true depending on which drawer you’re standing in front of. The catalogue workflow and the triage agent earned their place because I could name the exact hour they were going to save before I built them. Most of what causes the fatigue in this conversation is the stuff that skipped that step.

    The test

    So the test I keep coming back to, for my own work and for clients, is embarrassingly simple: can you say what this is replacing, specifically, before you turn it on? If yes, it’s probably not the wheel. If you’re not sure — that’s worth noticing too.

  • Michael Edwards walked. The template he was promised never came.

    Michael Edwards walked. The template he was promised never came.

    Michael Edwards has left his role as CEO of Football for Fenway Sports Group. The official statement will be gracious. The reality is that he told FSG last August he was done, and nobody who watched the 2025-26 season unfold could be surprised.

    Edwards returned to the Liverpool orbit in March 2024 on a specific premise. FSG wanted to build a multi-club network – a Red Bull or City Football Group structure with Liverpool at the top. Edwards, who had been Liverpool’s sporting director during the Jürgen Klopp era and was widely credited with assembling the 2019-20 title-winning squad, was the man to lead it. He accepted the role of CEO of Football on the explicit condition that the multi-club expansion was real. It was not.

    FSG explored Bordeaux. It collapsed into administration. They looked at Getafe. Nothing materialised. Malaga was discussed. A minority stake in AS Monaco was floated. Each approach died quietly, and by the summer of 2025 Edwards had concluded the project he was hired to build was never going to happen. Paul Joyce of The Times reported that Edwards was “frustrated as far back as last summer by the lack of progress with regard to the purchase of a second club.” He gave notice not long after.

    The season that made everything worse

    If the multi-club failure was the structural collapse, the 2025-26 season was the public humiliation. Arne Slot won the Premier League in his first campaign – Liverpool’s first title since 2020 – and 12 months later he was sacked. The final table told the story: 17 wins, 9 draws, 12 losses, 60 points. The defending champions had conceded 12 league defeats and finished well outside the title conversation. In May, FSG acted. Andoni Iraola of Bournemouth is now the frontrunner to replace him. The club that had a long-term plan for managerial succession is now looking for its third manager in four years.

    The Slot decision was driven in part by Edwards and sporting director Richard Hughes. The Times reported that the pair presented “cold, hard holistic analysis” that convinced FSG a more aggressive approach was needed. That analysis cost Slot his job. It may cost Hughes his as well. Al-Hilal have formal interest in the Scot. Ben Jacobs reports Hughes will stay this summer to lead a revamp with three or four senior signings, but Joyce has noted he is “not at Liverpool for the long term.”

    Mike Gordon and the drift

    Mike Gordon, the FSG president who personally recruited Klopp in 2015, is now the only senior figure with meaningful institutional authority at Liverpool. Edwards has gone. Hughes may follow. Slot is out. The coaching staff is in flux. Gordon must now hire a new manager, and perhaps a new sporting director, and perhaps a new CEO of Football – all under an ownership group whose most visible strategic move of the past two years was to abandon its own strategy.

    David Ornstein put it bluntly in The Athletic: “FSG is allowing Liverpool to drift – and that is dangerous.” He was writing before Edwards formally exited, but the point applies with greater force now. A club that built its post-Klopp identity around a clean division of powers – head coach, sporting director, CEO – is now watching each of those roles fall vacant in rapid succession.

    FSG can point to the league title and a rebuilt midfield. It can argue that the Slot sacking was decisive, not panicked. But the sequence is hard to spin. Promise a multi-club network. Abandon it. Win the league. Collapse. Sack the manager. Lose the CEO. The one constant is Gordon, who has been here before – his recruitment of Klopp saved the last FSG project that was drifting. He is about to be asked to do it again.

  • Why do candidates run with so much baggage?

    Why do candidates run with so much baggage?

    Graham Platner is out. The Maine oyster farmer who stormed a Senate primary and then collapsed in less than forty-eight hours did not fall because the political machine is rigged against honest people. He fell because a credible allegation of sexual assault landed, and the rest of his record was already a warning sign nobody had bothered to read.

    Let’s be plain about the charge. A former partner told Politico that an intoxicated Platner entered her home uninvited in 2021 and assaulted her. He denied it. That is the most serious item in the file, and it is not the kind of thing a “colorful past” brushes aside. When your campaign ends two days after that story publishes, the decent response is not to mourn the lost outsider. It is to ask why he was ever the frontrunner.

    The “aw shucks” myth

    The sympathetic version writes itself: a scrappy nobody takes on the establishment and gets taken down by powers that be. Platner told his own supporters exactly that. He said he was pushed out by structures, not by his conduct. That framing is convenient and false. The structures that withdrew were his own allies: the progressive senators who championed him, the national party that funded him. They left when the allegation landed, which tells you what they had known or suspected and been willing to overlook.

    The “good guy taken down by the machine” story only works if you ignore the part where the machine was his biggest fan until Tuesday.

    Calling him “another good one gone” inverts the truth. A candidate facing a credible sexual-assault allegation is not a good one. The reluctance to say so out loud is its own problem.

    The baggage was always the point

    Platner’s appeal was authenticity, and in politics authenticity is often just unvetted history wearing a flannel shirt. The offensive posts, the tattoo with Nazi connotations, the explicit messages sent after he was married. None of it slowed the primary. Seventy-two percent of Maine Democrats voted for him anyway. The base did not miss the baggage. They treated it as proof he was real.

    That is the dangerous trade. We have decided that a spotless record looks laundered and a messy one looks honest. So we reward the unexamined and call the consequences “political.” The assault allegation is not political. It is the reason the campaign should never have been a serious contender.

    Scrutiny is the job

    The cheap defense of Platner is that everyone has a past. True, and irrelevant. Most of us are not running for the Senate, and the standard for a candidate is not “better than the worst version of yourself in private.” It is whether the people asking for power have earned the trust. Vouching for someone and vetting them are different acts, and the party confused the two until it was forced to choose.

    The permanent, searchable record did not end his campaign unfairly. It ended a campaign that ought to have ended months ago, on the strength of what was already public. The last allegation broke through. The rest should have been enough on their own.

    What it actually costs

    The real damage is not to Platner. It is to the race. Maine Democrats now scramble to replace him before a July deadline, with a harder path against a senator who has held her seat for thirty years. The movement he built could carry the next candidate or sit out the election furious that the process felt rigged. That is the tax of betting on a charismatic unknown. When he falls, everyone else inherits the mess.

  • The case for boring software

    The case for boring software

    There is a particular kind of excitement that comes from installing something new — a fresh tool, a rewritten app, a framework that promises to change how you work. I have felt it more times than I can count. And I have paid for it more times than I care to admit.

    The pattern is always the same. The new thing is shinier, faster on the demo, and full of features I will never use. Six months later it is abandoned, broken, or both, and I am back to the dull, dependable program that was sitting there the whole time.

    What “boring” actually means

    Boring software is not bad software. It is software that has stopped surprising you. The keyboard shortcuts are in your muscle memory. The file format has not changed since 2009. When you open it, it does what it did yesterday. That predictability is a feature, not a lack of one.

    The boring tool is the one that is still maintained by someone who cares, but who is not trying to reinvent the category. It gets out of your way. You stop thinking about the tool and start thinking about the work.

    The hidden tax of the shiny

    Every switch has a cost that the launch video never shows. There is the migration, the re-learning, the plugin you have to rebuild, and the moment three weeks in when you discover the one thing the old tool did that this one simply will not. None of that shows up in the “Why we switched” blog post.

    The most expensive software in my life has never been the expensive software. It has been the free, exciting tool I adopted, rebuilt my workflow around, and then watched rot.

    When boring is the right call

    If a tool touches work you cannot afford to lose — your writing, your client records, your financials — boring wins. Stability beats novelty the moment the data matters. A plain-text notes file from 2014 still opens. The proprietary app that stored everything in its own cloud may not.

    Boring also scales across time. The format that survives a decade is the one you will never have to migrate again. That is a gift to your future self.

    When the shiny is worth it

    I am not anti-new. The exciting tool earns its place when it does something the boring one genuinely cannot — a real capability, not a prettier button. Try it on the side. Keep the old one running until the new one has earned the promotion. Promote rarely.

    The quiet advantage

    Most people chase the next release. If you instead pick tools that will still be here in five years, you inherit a quiet advantage: you spend your attention on the work, not on the tools. That is the whole case for boring software. It is not glamorous. That is the point.

  • Arne Slot Has a Premier League Title. That Might Be the Problem.

    Arne Slot Has a Premier League Title. That Might Be the Problem.

    One Premier League title each. Arne Slot has one. Jurgen Klopp has one. Slot took two seasons to get his. Klopp needed nine.

    That sentence is true, rude, and incomplete all at once. It is the kind of barstool stat you drop to watch someone’s face cycle through four different emotions before they decide which hill to die on. Let’s climb it together.

    The Dream Start

    Slot’s first season was a sugar high. He walked into the hardest job in football — replacing a deity — and won the Premier League with four games to spare. Twenty-six matches unbeaten. First Dutch manager to do it. Seventh manager in history to win the league in his debut season. Mohamed Salah scored 29 goals. The football was controlled, professional, and ruthlessly efficient. It was not heavy metal. It was a spreadsheet that kept winning.

    The narrative wrote itself. “Maybe the system was the genius all along.” “Maybe Klopp built a machine that could drive itself.” “Maybe Slot is actually brilliant.” All three floated around Anfield last summer, and all three contained some version of the truth.

    Context for the Catalog

    Klopp’s one league title in nine seasons sounds thin on paper. The full context is a lot uglier.

    Four times Klopp’s Liverpool went toe-to-toe with Manchester City and came out second by the slimmest margins in Premier League history. Ninety-seven points in 2018-19. Ninety-two points in 2021-22. Two titles lost by a single point each. Meanwhile, City are staring down 115 charges for financial doping.

    That is not a whataboutism. That is the defining asterisk of an entire era. Klopp didn’t lose to a better team. He lost to a balance sheet. His one league title should probably be four, and everyone who watched it unfold knows it.

    Slot inherited a club built by that fight. Jürgen Klopp did not inherit a Premier League-ready machine. He built one from the studs up, and the only reason his trophy cabinet doesn’t show four league titles is that the sport’s financial regulations were apparently optional for one competitor.

    The Rot

    Then came year two.

    The 2025-26 season began in tragedy. Diogo Jota’s death in a car crash in July cast a shadow that never fully lifted. The club and the city grieved publicly. Slot had to manage through something no manual covers.

    Liverpool started well — five wins on the bounce, top of the table — and then the floor gave way. Six defeats in seven league matches. A tumble to 12th in November. The champions looked unrecognizable. The same issues kept recurring: slow starts, defensive lapses, an inability to change the shape of a game that was slipping away. Slot tried patience. He tried continuity. He did not try something different, because it appears he does not have much of a Plan B.

    They recovered to finish 5th and scrape Champions League qualification. Respectable, on paper. The underlying story is less kind. The flaws did not get fixed. They got papered over by a soft run of fixtures and a few individual moments of quality.

    Keeping Him Is a Bet

    Arne Slot is entering the final year of his contract. The club decided to hold. That is either patient or timid, and the next six months will tell us which.

    If you believe the 2024-25 title was evidence of a long-term manager, the decision makes sense. If you believe the 2025-26 collapse revealed something fundamental — a manager who can steer a well-oiled machine but cannot redesign it mid-journey — then keeping a lame-duck head coach into a contract year is a recipe for drift.

    I would have moved on in January. Not out of animus — I do not know the man and he seems perfectly likeable — but because the job description is “fix the problems,” and the problems stared back at him for five months without getting solved. A long run of the same issues is not bad luck. It is data, and data eventually demands a decision.

    The Decent Guy Problem

    Here is the tension at the heart of Slot’s tenure: he is a decent guy. Competent, calm, well-prepared. The players seem to like him. The press conferences are pleasant. There is no drama, no tantrums, no exploding at the fourth official every weekend.

    In the Premier League, “decent guy” is sometimes enough. Ask David Moyes — decent got him into the door at Old Trafford, and decent got him sacked within a season. In Slot’s case, it was enough to win a title with someone else’s squad playing someone else’s patterns. The question is whether it is enough to build something of his own, with his signings, playing his way.

    When the wheels came off in the autumn of 2025, there was no visible pivot. No tactical shift, no formation change, no public spark. Just the same shape, the same approach, the same post-match analysis about fine margins. Decent guys do not always have a mean streak, and elite sport tends to demand one eventually.

    What Happens Next

    My read — and this is speculation, not prophecy — is that Slot is sacked by Christmas. The contract situation will hover. The results will wobble. The crowd will grow restless. And at some point, the club will decide that drifting toward a mid-table finish with a manager who cannot sign an extension is worse than making an uncomfortable decision early.

    The natural caretaker is already in the building. Virgil van Dijk as player-manager writes itself. He is the captain, the figurehead, the best defender on the pitch, and the most respected voice in the dressing room. If the club needs someone to steady the ship for six months while they find the next long-term appointment, you could do a lot worse than handing the armband a notebook and a set of cones.

    Close

    One league title each. Slot has number 20. Klopp has number 19. The same number. The same trophy.

    They are not the same achievement. Slot’s title was a masterclass in stewardship — taking a finely tuned machine and keeping it running at peak performance. Klopp’s title was a masterclass in construction — building that machine from scrap while a state-adjacent rival cheated the system beside him.

    Decent is not a dirty word. Slot is a decent manager with a Premier League medal to prove it. But decent does not always mean right, and the 2025-26 season suggested that being liked and being effective are not the same thing. Sometimes the decent guy gets the job done. Sometimes he just gets a longer runway before everyone realizes the plane cannot change course.

  • Eat Your Own Dog Food

    Eat Your Own Dog Food

    In the tech world, we have a saying: “Eat your own dog food.”

    It is a simple rule. If we are going to ask you to pay for a service or a piece of hardware, we should be using it to run our own business first.

    At OConnell I.T., we take this seriously. We do not chase trends and we do not sell hype. Before we suggest a change to your business, we become the crash test dummies.

    Take the mini-PCs many of our clients use now. Before we recommended them to a single family business on Long Island, we bought them for ourselves. We tore them down. We ran them as our daily workstations for six months to see if they would overheat or lag. We wanted to find the breaking point on our clock, not yours.

    The same goes for our infrastructure. We host our own website. We use our own servers. We rely on the same backup systems we install for you. If those systems fail at 7 AM, it is our problem before it is ever yours.

    Lately, everyone is talking about AI. Most of it is just noise. We have been running daily exercises with AI tools for months to find the actual value for a small business. We are not looking for “revolutionary” shifts. We are looking for faster response times, cleaner communication, and quicker estimates for your customers.

    We recently helped a client automate their content scheduling. They told us:

    “Our customers see our social media accounts are alive again.”

    That is a real business outcome. It is not a buzzword. It is a tool that works.

    Think of it like your CPA. You trust them because they use the same rigorous standards for their firm that they use for your books. They wouldn’t touch a software they didn’t trust, and neither will we.

    We do the testing. We deal with the implementation headaches. We learn what works and what is just a waste of your time.

    By the time we offer a service to you, it is not an experiment. It is a proven tool that we already trust to keep our own doors open.

    If you want technology that is tested and a partner who actually shows up, let’s talk.

    OConnell I.T.
    Plain-speaking. Proven. Local.

  • The ‘Hollywood’ Problem — When a Client Says No for the Right Reason

    The ‘Hollywood’ Problem — When a Client Says No for the Right Reason

    One of the more useful moments in client work is not when you present a strong idea.

    It’s when a client turns one down for the right reason.

    I was in a branding session last week. We covered the usual areas:

    • Content strategy
    • Visual direction
    • Marketing channels
    • ROI

    The conversation moved to AI-generated video.

    They said no immediately.

    This wasn’t pushback for the sake of it.

    It came from experience.

    They had tried radio advertising before. It didn’t land.

    • Customers felt a disconnect
    • The messaging came across as too polished
    • The brand didn’t feel like itself

    They summed it up in one line:

    “It felt like we’d gone Hollywood.”

    That explained the reaction.

    From their point of view, an AI spokesperson creates the same problem.

    • It changes the tone
    • It creates distance
    • It risks trust

    For a small, family-run business, that matters more than production quality.

    There’s a broader point here.

    Most conversations about AI focus on what it can do.

    Very few focus on whether it fits.

    • A tool can be effective
    • It can also be wrong for the brand
    • Perception usually wins

    Good business owners understand this, even if they don’t spell it out.

    They know where the line is.

    Where improvement starts to feel like something else.

    The takeaway is simple.

    Businesses are often the best custodians of their own brand.

    They understand what their customers trust.

    And they know what would break it.