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Tag: The Power Broker

  • Lloyd Blankfein on the 3 Sectors Where He Puts His Money Now: Big Tech, Energy, and Financial Services, Day Trading From an iPad, and the Warren Buffett Handshake That Backed Goldman in 2008

    Lloyd Blankfein spent almost 40 years at Goldman Sachs, the last dozen as its chairman and chief executive, and he still trades almost every day from an iPad. In this wide ranging conversation on the My First Million podcast, the former Goldman boss lays out exactly where he is putting his own money right now, why a supportive spouse beats nearly any investment, how Warren Buffett wired five billion dollars into Goldman on a handshake during the 2008 crisis, and why he reads medieval history to stay calm about the present. It is part stock picking, part risk philosophy, and part a frank accounting of money, marriage, and the scars of growing up in the projects.

    TLDW

    Blankfein says he is roughly 98 percent in risky assets, almost all equities, and concentrated in three sectors he knows cold: big tech, energy, and financial services. His personal book leans heavily into single stocks over ETFs, weighted toward the big hyperscalers and a few second tier names, and he trades daily, alone, from an iPad and a phone, using calls and texts as his research network. Yet the advice he gives a normal investor is the boring opposite: a diversified S&P 500 fund like VOO, more risk when you are young because you will outlive your mistakes, the same thing Warren Buffett would tell you. The conversation ranges across the 2008 Buffett investment in Goldman, the cost of trying to legislate risk out of markets, the thin margin between the best and the rest, luck and the myth of the genius, why reputation is the real contract on Wall Street, why a supportive spouse is the highest return asset he knows, the money anxiety he carried out of a Brooklyn housing project, the dignity of a 500 dollar financial aid check, giving with a warm hand versus a cold one, the dangers of gamified investing, the big misses like SpaceX and early cellular, the obituary test a senior partner once gave him, and why reading history keeps the present in proportion.

    Thoughts

    The most useful tension in this interview is the gap between what Blankfein practices and what he preaches. He tells young people to buy a diversified S&P 500 index fund, he holds VOO himself, and he calls the host’s plain 90 percent stocks and 10 percent bonds split sensible. Then he admits his own portfolio is something like 90 percent single stocks that he trades by hand every day. The honest read is that his edge is not a transferable tip. It is a 40 year information network of phone calls and a tolerance for risk that most people neither have nor should want. The replicable lesson is the boring half, not the day trading half.

    The most contrarian idea here is not a stock pick, it is his defense of risk itself. His argument that regulators trying to prevent the hundred year storm also forfeit the 99 normal years of growth in between is a serious claim about the price of safety, and it travels far beyond Wall Street. The same goes for his point that a good risk manager sometimes has to push people to take more risk, not less. The moment after a loss, when everyone goes gunshy, is exactly when the best operators lean back in. That is an uncomfortable thing for a former bank CEO to say out loud, and it is the part of the conversation most worth sitting with.

    The Warren Buffett story is a master class in what actually moves markets, and it is not cash. Goldman did not need the five billion dollars. Blankfein says the money was almost irrelevant because the firm already had money. What it could not manufacture was confidence, and Buffett’s name supplied it. The handshake, the commitment with no paperwork, the line about worrying enough for the both of us, all point to the same thing. At the top, reputation is the collateral. His aside that most trades are never written down because you will never eat lunch in this town again is the same idea wearing street clothes.

    Quietly, the personal finance thread may be the most valuable part for a normal listener. A former Goldman CEO saying that a supportive partner is more game changing than any investment, that a bad marriage is financially worse than being lonely, and that he has not paid a bill in over 40 years because his wife runs the household economy, is a reminder that household stability is itself an asset class. The 500 dollar financial aid check he still remembers half a century later, and his give with your warm hand philosophy, reframe wealth as something measured by how it feels to give and to receive, not just by the size of a pie chart.

    Finally, the history obsession is not a side hobby, it is his risk model. Reading about the black plague, the McCarthy era, and the Vietnam draft is how he keeps the present in proportion. His Mark Twain line, that history does not repeat but it rhymes, is the direct antidote to the in this economy defeatism he and the host both complain about. For an investor, that long view is close to the whole game. It is what lets you hold through the drawdowns that scare everyone else out of the market.

    Key Takeaways

    • Blankfein estimates he is about 98 percent in risky assets, with roughly 95 of those 98 points in equities, and the rest spread thin. He invests in risky assets because, in his words, that is what is fun for him.
    • Within his equities, he is heavily tilted toward single stocks rather than ETFs. He frames it as roughly a quarter to a third in ETFs and the rest in single names, and concedes it could be as lopsided as 90 percent single stocks because picking names is what he enjoys.
    • The three sectors he has concentrated in for years are big tech, energy, and financial services, and he says his outperformance comes from where he focused, not from any special genius.
    • On tech he owns the big hyperscalers, the Googles, Microsofts, and Nvidias of the world, plus a tier just below them, naming Oracle and Larry Ellison as an example of a slightly riskier second tier name. He thinks in categories, not fixed tickers, because he changes positions constantly.
    • He says he has a background in trading energy, which is why energy is a core sleeve, and he knows financial services from the inside after almost 40 years at Goldman, so those are natural areas of edge.
    • He still owns a lot of Goldman Sachs stock, out of affection for the firm he spent his career building.
    • He is bullish on big tech and plans to stay bullish until it stops going up. His foreseeable future, he jokes, lasts until he finishes the conversation and checks the screen again.
    • He trades every single day, alone, with no team. He does it from an iPad and a phone, not a computer, and treats the market like background music rather than a job.
    • His research is human, not algorithmic. He chats and texts with people, then calls them because he is tired of fixing typos, and he reads the New York Post, the Wall Street Journal, the New York Times, the Financial Times, and Bloomberg.
    • The advice he gives ordinary investors is deliberately boring and different from his own behavior: hold a diversified equity portfolio like an S&P 500 fund, with VOO as his own example, and tilt more aggressively when you are young because you have time to outlive mistakes.
    • He notes that broad indexes are already heavily weighted toward tech because of market cap, so a plain index gives meaningful tech exposure, and a tech focused ETF on top can add a disproportionate tilt for believers.
    • He calls the host’s simple 90 percent index and 10 percent bonds allocation sensible, and says this is essentially the same advice Warren Buffett would give a normal person.
    • The older you get, the more conservative you should become, shifting from maximizing gains toward not losing what you have. Young people can afford more risk precisely because they will outlive their errors.
    • During the 2008 financial crisis, Warren Buffett invested about five billion dollars in Goldman through a preferred stock structure, essentially on a phone call and a handshake, with no demand for due diligence.
    • Buffett’s real value was confidence, not capital. Goldman already had money, but it had lost the confidence of the market while peers were failing. Buffett’s name signaled the firm was a good investment being beaten down by circumstances that would reverse.
    • Buffett asked for a verbal commitment that Goldman would not sell shares before he did, and declined to put it in writing. He waved off the worry with the line that five billion dollars going bad would not even be a bad hurricane for Berkshire, an insurer.
    • Most trading is done on reputation, not paper. Blankfein says people buy and sell bonds worth enormous sums without written contracts, relying on probity, because anyone who reneges will never eat lunch in this town again.
    • On risk and regulation, he argues you cannot legislate risk away. Trying to prevent the hundred year storm also forgoes the 99 in between years of growth, and a good risk manager sometimes has to encourage people to take risk, not suppress it.
    • The best traders have resilience. They bounce back, focus on new information rather than the past, and adapt quickly instead of staying gunshy after a loss.
    • The difference between someone who is really good and someone who cannot make it is small. He compares it to a golf tournament won by one stroke with six people tied for second, and notes much of life is winner take all at razor thin margins.
    • Luck matters enormously. He became Goldman CEO partly because his predecessor was nominated to be Treasury Secretary, a reference to Hank Paulson, and the timing of opportunities is often out of your control.
    • He is skeptical of the word genius. He says he can usually see how successful people do what they do, with Elon Musk as a rare exception, and that powerful people are more normal, more insecure, and more flawed than outsiders assume.
    • On democratized investing, he thinks apps that make markets accessible are good in their own terms, but gamifying trading with confetti and high fives can mask real danger for people who can lose more than they can afford.
    • He has missed plenty. He thought SpaceX was overpriced at a 100 billion dollar valuation, now discussed near a trillion and three quarters, and passed on early cellular because he could not imagine why anyone would carry a bulky phone when payphones existed. He says he missed far more than he got.
    • He frames a supportive spouse as more game changing than almost any investment, and warns that a bad marriage, with custody fights and property settlements, is financially and personally worse than being lonely.
    • He has not paid a bill in over 40 years. His wife Laura, a former lawyer he says now chairs Barnard College, runs a bill paying service and manages the household economy. He generates the money, she distributes it.
    • He grew up in an East New York, Brooklyn housing project, the son of a postal worker, and carried money anxiety well into his 30s. He recalls buying a vacation home that cost more than all their savings, with his wife unable to make the math work until they remembered the down payment.
    • A 500 dollar financial aid check, handed to him without shame as a college freshman around 1971, shaped his philosophy on giving. He learned it is not enough to give people what they need, you have to give it in a way that feels dignified.
    • He embraces the give with your warm hand, not your cold hand idea, the notion of giving while alive so you can experience the joy, which connects to the spirit of the book Die With Zero.
    • He admits ambivalence about giving to his kids, the strange feeling of resenting that they have what he provided, and notes the heavy burden carried by children of prominent people who must prove they earned their place.
    • He describes himself as wired for anxiety, inherited from his father, and says looking around corners for what could go wrong actually suited a career in a risky business with a big balance sheet.
    • When he made partner, a senior partner gave him rules of the road, including avoiding misconduct, being conservative on taxes, setting up a charitable foundation, and living so that no more than three of the nine paragraphs in his eventual obituary would be about Goldman. He says he stayed too long to pass that test.
    • He reads history as a discipline, favoring Barbara Tuchman, Robert Caro’s The Power Broker, Ron Chernow, Rick Atkinson, and Stephen Ambrose. His core belief, borrowed from Mark Twain, is that history does not repeat but it rhymes, which is why he would not bet against America.

    Detailed Summary

    The three sectors he actually invests in

    The headline answer to where the former Goldman CEO is putting his money is simple: big tech, energy, and financial services. He says he has been focused on those three areas for a long time, and that his outperformance is a function of where he aimed rather than any unusual investing gift. Energy is natural because he has a background trading it. Financial services is natural because he spent nearly 40 years inside the industry. Tech is where he is most heavily concentrated, and he expects to stay there for good reason, citing the threshold of large changes in technology. He owns the major hyperscalers by category, the Googles, Microsofts, and Nvidias, plus a tier just below, offering Oracle and Larry Ellison as a polite example of a slightly riskier second tier name. He is careful to say he thinks in categories rather than fixed tickers because he changes his positions all the time.

    How the portfolio is really built: single stocks over ETFs

    Asked to describe his portfolio as a pie chart, Blankfein says he is about 98 percent in risky assets, with roughly 95 of those points in equities. He pushes back on the idea that index funds are safe, pointing out that a diversified equity ETF is still equities and still risky, just spread out, and very different from debt or short term money markets. Within his equity sleeve he leans into single stocks, framing it as somewhere between a quarter and a third in ETFs and the rest in individual names, and conceding it might be as extreme as 10 percent ETFs and 90 percent single stocks. The reason is preference, not theory. Picking and trading names is what he likes to do, and he is honest that this is a hobby pursued by a professional, not a model for someone investing for a living.

    How he actually trades: an iPad, a phone, and a network

    He trades every day, by himself, with no team. There is no Bloomberg terminal and no desk of analysts. He uses an iPad and a phone, and admits it takes discipline not to glance at his screen mid conversation. The market, he says, is like music playing in the background while he does other things. His information edge is relational. People text him, he texts back, and then he calls because he is tired of fixing typos with what he calls his fat fingers. He follows general and business news, reads a stack of newspapers starting with the New York Post, and treats companies like little stories, almost like gossip. He even notes, with some delight, that he still watches commercials on Netflix, a small window into a frugality that never fully left him.

    The advice he gives young investors, and what Buffett would say

    For a normal person, his counsel is the opposite of his own behavior. He would hold a diversified portfolio of equities like an S&P 500 fund, naming the SPY and VOO tickers and saying he personally uses VOO. Because of the importance of technology, he might add a tech oriented ETF for extra tilt, while noting the broad index is already tech heavy by market cap. He endorses the host’s plain 90 percent index and 10 percent bonds split as sensible and says it mirrors what Warren Buffett would advise. His one piece of age based guidance is that younger investors should accept more risk through equities, because they have time to recover, while older investors should grow more conservative and focus on not losing what they have rather than maximizing returns.

    The Warren Buffett handshake that backed Goldman in 2008

    The most cinematic story in the conversation is Buffett’s roughly five billion dollar investment in Goldman during the financial crisis, structured as a preferred stock that sits between a loan and equity. Blankfein describes a deal done largely on trust. When he offered to walk Buffett through everything he was worried about, Buffett replied that he knew Lloyd well enough to know he worried enough for the both of them. Buffett also asked, verbally and without writing, for a commitment that Goldman would not sell shares before he did. Blankfein is clear that the cash itself was almost irrelevant, since Goldman had money. What the firm lacked was the confidence of a frightened market, and Buffett’s willingness to invest before things improved supplied exactly that signal. Buffett, he stresses, was acting for his own shareholders, not as a rescuer, which is precisely what made the vote of confidence credible.

    Why you cannot legislate risk out of the system

    Reflecting on the post crisis regulatory push to make sure 2008 never happened again, Blankfein makes a careful argument about the price of safety. Once you are in the business of taking risk, anything can happen, and trying to legislate it away has a hidden cost. You may think you are protecting the world from the hundred year storm, but you also forgo the 99 years of growth in between. He extends this inside the firm too. After a period of big losses, partners had become gunshy and were talking themselves out of every idea. A good risk manager, he argues, sometimes has to promote risk taking rather than repress it, because without risk there is no growth, no entrepreneurship, and no progress. The flip side is real: take risk and there is a meaningful chance you fail and lose other people’s money, which is a terrible outcome. But the alternative, never risking anything, buys comfort at the cost of ever moving forward.

    Small margins, big outcomes, and the role of luck

    Asked what separated the traders who could not outperform from the rest, Blankfein says the gap between the very good and those who cannot make it is surprisingly small. He likens it to a golf tournament decided by a single stroke with six players tied for second, and to acting, where the best performer gets every role and the second best waits tables. Much of life, he says, is winner take all at tiny margins. Luck compounds this. He freely credits fortune for his own rise, noting he became CEO in part because his predecessor was tapped to be Treasury Secretary. He is also skeptical of the genius label. He can usually see how accomplished people do what they do, with Elon Musk a rare exception, and insists the powerful are more normal, more insecure, and more driven by their flaws than outsiders imagine.

    Reputation is the real contract

    A recurring theme is that the financial world runs on reputation more than paperwork. Blankfein notes that most of what traders do is not written down. People buy and sell bonds and other instruments that settle days later, relying on probity rather than signed contracts, because anyone who lies or reneges will never eat lunch in this town again. He references the casual texts between Elon Musk and Larry Ellison around the Twitter acquisition as proof that big does not mean complicated. There are big things that are simple and little things that are complicated. Documentation is good when execution is far off, but when a deal will be performed in two days, dotting every i is often pointless. The point is not that documents do not matter, it is that trust and reputation are the load bearing structure.

    A supportive spouse as the highest return asset

    The conversation turns personal when both men agree that a supportive partner may be the single most game changing factor in a life, more than any investment. Blankfein adds the inverse warning: a bad marriage, with breakups, custody battles, and property settlements, is worse than loneliness. He credits his wife Laura, a former big firm lawyer he says now chairs Barnard College, with handling everything when his career moved the family overseas, from the car to the house to the kids’ schooling, while he took the visible victory laps at work. He has not paid a bill in over 40 years. Laura manages a bill paying service and runs the household finances. As he puts it, he is in charge of generating the money and she is in charge of distributing it. The host contrasts this with his own monthly money meetings with his wife, a discipline he picked up from a personal finance author friend.

    Money scars, the 500 dollar check, and giving with a warm hand

    Blankfein grew up in an East New York housing project, the son of a postal worker who had earlier lost a job, in a household where rent was scarce. He calls himself an urban hick who barely left Brooklyn as a kid. That scarcity left a mark that lasted into his 30s. He tells the story of buying a small beach house that cost more than all their savings, and of his wife driving 30 miles while failing to make the closing math work, until they realized she had forgotten to count the 10 percent down payment. The most resonant memory is a 500 dollar financial aid check handed to him as a freshman around 1971, made out on the spot by a clerk with a generosity of spirit that let him receive it without shame. That experience shaped a lifelong view that giving well means preserving dignity, and he now co chairs a financial aid campaign at his university. It also connects to his embrace of the idea of giving with your warm hand rather than your cold hand, giving while alive so you can feel the joy, the same spirit as the book Die With Zero. He is candid about a strange ambivalence, the way he can resent that his kids enjoy what he himself gave them.

    Robinhood, confetti, and the misses

    On apps like Robinhood, Blankfein takes a balanced view. Democratizing investing and making assets accessible is good in its own terms, and advertising can pull people toward markets they would otherwise ignore. But if you make trading too much like a video game, with confetti and high fives, you can mask the danger and lure people who cannot afford to lose into losing more than they can. He is equally frank about his own misses. He thought SpaceX was overpriced at a 100 billion dollar valuation, a figure now discussed near a trillion and three quarters. He passed on early cellular because he could not imagine why anyone would carry a bulky phone with payphones everywhere. His blunt summary is that he missed far more than he got, and that nobody is great at predicting the future.

    The obituary test, thick skin, and staying too long

    When Blankfein made partner, a senior partner assigned to acculturate new partners gave him rules of the road: avoid anything that would today be called misconduct, be rigorous and conservative on taxes, set up and actually use a charitable foundation, and keep enough balance that, if your obituary runs nine paragraphs, no more than three are about Goldman. Blankfein says he failed that last test by staying too long, even titling his memoir around the firm. He also reflects on having a thick skin, recalling unflattering press and concluding that he could take a punch, a trait not everyone has and one he did not know he possessed until he was tested. He is careful to say this does not make people who cannot take a punch bad, just differently wired.

    Why he reads history: it rhymes

    The final stretch is a love letter to reading history. Blankfein favors Barbara Tuchman, whose A Distant Mirror he has read twice and whose Guns of August he calls fantastic and influential, along with Robert Caro’s The Power Broker on Robert Moses, Ron Chernow’s biographies, Rick Atkinson’s Revolution series, and Stephen Ambrose’s Undaunted Courage. He describes rereading the Robert Moses book after 40 years of trying to get things done and finding his appreciation for the achievements rise, even as the flaws stayed the same, because he had changed. He ties history directly to markets through the Mark Twain line that history does not repeat but it rhymes. Patterns recur, every generation maximizes its own crises and minimizes resolved ones, and reading about the black plague, the McCarthy era, or the Vietnam draft is how he stays calm. His conclusion, echoing a sentiment often attributed to Buffett, is that he would not bet against America, a country he describes as mostly good and able to improve.

    Notable Quotes

    “I invest in risky assets. That’s what’s fun for me.”

    Lloyd Blankfein, describing his own portfolio, which he says is roughly 98 percent risky assets

    “It’s been good to be bullish on big tech, and I’ll stop being bullish on it when it stops going up.”

    Lloyd Blankfein, on why he stays concentrated in technology

    “I’m not at a computer. I don’t have a computer. I have an iPad.”

    Lloyd Blankfein, on how he day trades every day, alone and with no team

    “To me, the market is like music. It’s out there. It’s going on.”

    Lloyd Blankfein, on why trading daily feels like a hobby rather than work

    “Look, $5 billion if it all goes bad, that’s not even a bad hurricane on the East Coast.”

    Warren Buffett to Lloyd Blankfein, waving off the risk of his 2008 investment in Goldman Sachs

    “The difference between somebody who’s really, really good and somebody who can’t make it is not that great.”

    Lloyd Blankfein, on the thin margin between the best and the rest

    “You may think you’re protecting the world from the hundred-year storm, but you’re also going to forego the 99 years of in between when there was growth.”

    Lloyd Blankfein, on the cost of trying to legislate risk out of markets after 2008

    “I’m in charge of generating the money, and she’s in charge of distributing it.”

    Lloyd Blankfein, on his 40-plus-year marriage to Laura and why he has not paid a bill in decades

    “History doesn’t repeat, but to paraphrase Mark Twain, it rhymes.”

    Lloyd Blankfein, on why reading history keeps the present in proportion

    Watch the full conversation with Lloyd Blankfein on the My First Million podcast here.

    Related Reading

    • Lloyd Blankfein (Wikipedia) background on the former Goldman Sachs chairman and CEO whose investing views anchor the conversation.
    • My First Million podcast the show where this interview took place, for the full back catalog of investor and founder conversations.
    • Berkshire Hathaway primary source on Warren Buffett’s company, which made the roughly five billion dollar Goldman investment in 2008.
    • Vanguard S&P 500 ETF (VOO) the diversified index fund Blankfein names as the sensible core holding for a normal investor.
    • Die With Zero by Bill Perkins the book behind the give with your warm hand, not your cold hand philosophy discussed near the end.

  • Dan Shipper’s Most Contrarian AI Predictions for 2026: Why the Job Apocalypse Is a Myth, SaaS Will Boom, PMs and Designers Win, and CLIs Are Already Over

    Dan Shipper, the CEO and founder of Every, returned to Lenny’s Podcast for round two of AI predictions. His last appearance produced one of the most prescient calls of the year: that non-technical people would build serious work inside Claude Code. He was unbelievably right. This conversation is the follow-up, a tour of his most contrarian forecasts for how AI is actually changing the way we work, who wins, who loses, and what almost every commentator is getting wrong about the next twelve to twenty-four months.

    TLDW

    Shipper argues that the AI job apocalypse is a myth, that SaaS is going to boom rather than die, that product managers and full-stack designers are the biggest winners of the agent era, that personal agents inside Codex and Claude Code will quietly replace the browser as the primary work surface, that every company will run a single shared super-agent in Slack instead of a fleet of per-user bots, that the CLI moment is already over, that pull requests are going to flood organizations from non-technical staff, that forward-deployed engineers who garden company agents become the new senior role, that GPT-5.5 still cannot match a real senior engineer on architectural judgment, that AI-generated internal writing is fine and probably better than what most humans produce, that CEOs and middle managers have not adapted yet but soon will be forced to, that the edge of AI lives wherever a curious human is using it rather than in San Francisco, and that the only durable strategy is to ride the models and keep playing with whatever ships next. The whole conversation balances aggressive AI bullishness with an equally strong bet on humans, on creativity, and on the unavoidable need for someone to care for every agent that gets deployed.

    Thoughts

    The most useful frame Shipper gives is that models commoditize yesterday’s human competence. Every time a frontier model crosses a new bar, the work that used to define seniority becomes cheap. The senior engineer who could carry a refactor in their head, the PM who could write a coherent strategy doc, the designer who could ship a polished landing page in a week. That competence is now frozen, codified, and available on tap. The interesting question is not whether models will keep eating tasks. They will. The interesting question is what humans do with the suddenly cheap raw material underneath them. Shipper’s answer is that humans climb the stack: they go up a level, find a new problem worth framing, and use the commoditized competence as feedstock for something that did not exist before. That treadmill is the actual engine of value creation, and it is why he can be simultaneously AI pilled and bullish on hiring.

    His SaaS take is the spiciest call of the episode and probably the most defensible. The crowd consensus is that agents will gut SaaS because an AI can just write the form filler, the dashboard, the workflow. Shipper points out the obvious counterfactual: agents do not reduce the number of people using SaaS, they increase it. A marketing lead who could never touch the data warehouse can now stand up a PostHog query through Codex. A founder who never opened Vanta can run a SOC 2 prep through an agent. The result is more users, more accounts, and a much fatter top of funnel for every horizontal tool. The second-order effect is even more interesting. When the SaaS tool runs inside the user’s agent, the user supplies the tokens. Vendor margins improve, not collapse. If he is right, the next two years are going to be brutal for the SaaS-is-dead thesis pieces and very good for the public software multiples.

    The PM and designer bet is where this gets personal for anyone in product. For a decade the bottleneck in shipping anything was engineering capacity. A PM with spiky product sense had to negotiate their vision through a roadmap, a sprint, a review, and a release. Designers had to convince an engineer that the third state of the empty screen was actually worth building. Both of those constraints are dissolving fast. A PM who can prompt Codex into a working prototype on Friday afternoon, then iterate it live in front of a customer on Monday, is doing the job of a small team. A designer who can ship a fully functional landing page in their own style, without negotiating with anyone, is suddenly the most leveraged person in the company. The scarce skill is no longer execution. It is taste, judgment, and the willingness to decide what is worth building. That has always been the real PM and design job. AI just stripped away the parts that were not.

    The quietest but most important prediction is that agents need humans, permanently. Every benchmark advance reveals a new layer of judgment the model cannot frame on its own. When the agent finishes the task, there is always a senior human who sees the deeper problem the model patched over. Shipper calls this gardening, and it is the basis for the new forward-deployed engineer role. The companies winning right now are the ones that put a real person next to every agent, watching what it does, course-correcting in Slack, and noticing when the output drifts. The dream of autonomous AI workflows is a stage in a journey, not the destination. The destination looks more like a thoughtful operator with a small cluster of agents they trust and constantly tend. That is a much more humane future than the discourse suggests, and it is the one Every is already living.

    The final advice, ride the models, sounds glib but is the single most actionable line in the episode. Most professional anxiety about AI dissolves the moment you actually use the newest model on real work. Most professional advantage accrues to the people who do that one thing consistently. The edge does not live in San Francisco where the labs build the things. It lives wherever a curious human meets a real workflow and discovers something the labs have not noticed. A PM in Iowa willing to try Codex on a Tuesday night can be further ahead than a research engineer who has only used the model on its evals. Pair that with Shipper’s closing motto, do things worth writing about and write things worth reading, and you have a pretty complete operating system for the next two years.

    Key Takeaways

    • The AI job apocalypse narrative is wrong. Models commoditize yesterday’s competence, then humans climb the stack and find new work to do with the cheap raw material.
    • Every has roughly doubled headcount in the last year despite being one of the most AI-forward companies in the world. The lived data point cuts directly against the doom thesis.
    • Shipper’s dual stance: simultaneously extremely AI pilled and very bullish on humans. He treats this as the only intellectually honest position right now.
    • Work will bifurcate. Companies will run one shared super-agent in Slack for everyone, and individuals will run their own personal agent inside Codex or Claude Code on their machine.
    • The personal agent inside Codex effectively becomes the new operating system. Instead of putting AI in the browser, you put a browser inside the AI.
    • The super-agent pattern is already real: Shopify has River, Ramp has its own, and Every runs Claudie inside Slack for internal consulting.
    • SaaS is not dying. Agents increase the user base of SaaS tools because non-technical people can finally drive them. Shipper would buy SaaS stocks today.
    • When SaaS runs inside an agent, the user brings their own tokens. Vendor margins improve because they no longer eat inference costs on every interaction.
    • The CLI era is already over. The magic was never the terminal. It was the AI plus the ability to see what the agent is doing. A good GUI captures the same benefits and more.
    • Pull requests are about to flood every company. Non-engineers can now ship code, run queries, and open tickets. Reviewing the output becomes the new bottleneck.
    • Open-source maintainers are already living in the future. Some receive thousands of agent-generated PRs per day and spin up thousands of Codex instances just to triage them.
    • Forward-deployed engineers are the new senior role. They live in Slack, garden the company’s agents, fix broken flows, and keep non-technical staff from doing damage.
    • Product managers with spiky product sense plus a little Codex fluency become extremely dangerous. Marcus at Every, formerly a PM at Axios, is the archetype.
    • Full-stack designers are the other big winner. They can build distinctive interfaces end to end without negotiating with engineering. The bottleneck on taste-driven product work disappears.
    • Designer hiring data has not yet caught up to the prediction. Shipper notes this and says check back in a year.
    • Sales is the role least changed so far. Top of funnel research has been turbocharged by agents, but the actual relationship and closing work remains human.
    • AI-generated internal writing is going mainstream and that is a good thing. Most humans are bad at strategy docs, quarterly plans, and PRs. AI drafts a coherent first pass that a human can refine.
    • Shipper says most of his email is now written by GPT-5.5 and Codex. He would honestly prefer the signature to say so.
    • Public writing, newsletters, and published essays still demand a human voice. Internal communication does not.
    • CEOs and middle managers have largely not adapted yet because their staff still does the work. That window is closing fast and will become an obvious career liability.
    • Your company will only go as far as your CEO goes in AI. The leadership ceiling becomes the AI ceiling.
    • Shipper’s senior engineer benchmark scores GPT-5.5 at roughly 62 out of 100. Real senior engineers sit at 85 to 90. Progress is real, but the gap on architectural judgment remains.
    • Models tend to patch problems locally instead of rewriting from first principles. A senior human still sees the deeper rework that the model avoids.
    • Every uses Notion-based agents to draft quarterly plans. The human edits, approves, and stands behind the output.
    • The hard rule on AI-generated communication: you have to read it and stand behind it before sending it. Pasting unread output is the only true no-no.
    • Every agent needs a human. Automation is a lie in the strong sense. The story of automation is the story of new and different humans being needed alongside it.
    • The reach test, organic daily usage, is the real signal that an AI product works. Benchmark scores are noisy. Daily reach is not.
    • Cursor’s SpaceX acquisition is a tell. Harnesses around models, not the models themselves, are where the strategic value is concentrating.
    • The edge of AI is not in San Francisco. It is wherever a real human meets a real workflow and discovers something the labs have not noticed yet.
    • A PM in Iowa willing to ride the models can be further ahead than a researcher in SF who only uses them on internal evals.
    • Ride the models. Use them for whatever you do. Try every new release the day it ships. That single behavior compounds faster than any other AI career strategy.
    • Shipper got bursitis, which he calls vibe coder elbow, from too much rapid agent-assisted coding while debugging his markdown editor Proof.
    • The closing motto for the year: do things worth writing about and write things worth reading.
    • Lenny will re-interview Shipper in roughly May 2027 to score the predictions.

    Detailed Summary

    Why The AI Job Apocalypse Is The Wrong Frame

    Shipper opens with the headline contrarian call. Benchmarks keep climbing. Models can now sustain seventeen-hour autonomous tasks at fifty percent accuracy. The pace is real and accelerating. None of that translates cleanly into mass unemployment. His mechanism: models codify yesterday’s human competence and make it cheap. The act of compressing past expertise into an API call is genuinely deflationary for the work it captures, but it is also raw material for the next layer of human work. He uses Every as his own data point. The company has roughly doubled in the past year despite being one of the most AI-forward outfits in media. Hiring goes up because agents create new categories of work that need humans, not because the agents fail. The discourse, he argues, is stuck modeling AI as substitution. The reality looks much more like leverage.

    The Bifurcation: Super-Agents And Personal Agents

    Work splits into two surfaces. The first is the shared super-agent that lives in Slack and serves the whole company. Shopify has River. Ramp has its own. Every has Claudie. Each is a single, trusted, gardened agent that anyone in the company can talk to. The pattern has converged on one shared agent rather than one agent per person because agents need human attention to stay useful, and a single shared instance pools the gardening cost. The second surface is the personal agent inside Codex or Claude Code that runs on your machine and reaches into your local environment, your editor, your files, and through an embedded browser into the web. Shipper calls this the new operating system. Instead of the old paradigm of putting AI inside the browser, you put the browser inside the AI. The agent sees what you see, follows what you do, and works on your stuff in your context.

    The SaaS Bet: Up, Not Down

    The SaaS-is-dead thesis was the consensus call of late 2025. Shipper takes the other side and would buy software stocks now. Three arguments. First, agents make SaaS accessible to people who never could have used it directly. The total addressable user base inside every company goes up. Second, the business model improves when the user runs the SaaS through their own agent, because the user supplies the tokens. Vendors stop subsidizing inference. Third, SaaS spend in his observable universe is up, not down, and is concentrating on the tools that play well with agents. He frames the prediction as a sound bite for the cycle: buy SaaS stocks, the apocalypse is dumb.

    The CLI Era Is Already Over

    For a moment in early 2026 it looked like everyone was migrating to the terminal because Claude Code was a CLI. Shipper says the moment is finished. The actual leverage was never the terminal. It was the model plus the ability to watch and steer an agent live. A great GUI captures every advantage of the CLI without the friction. His own engineering team at Every has mostly moved off the CLI as their primary surface and onto Codex desktop. He frames it bluntly: we speed ran the CLI era, it was nice, and now we are done. Tooling for the next two years will be visual, multi-pane, multi-agent, and built around the human watching the work unfold.

    The Pull Request Flood And The Rise Of Forward-Deployed Engineers

    Once non-engineers can ship code, run queries, and file changes through agents, the volume of incoming work explodes. Open-source maintainers already report receiving thousands of agent-generated pull requests per day. Inside companies, the same thing happens to data teams, ops teams, and any function that owns a review gate. The bottleneck shifts from creation to evaluation. The job that emerges to absorb the flood is the forward-deployed engineer. This is a senior person who lives in Slack with the company’s agents, fixes their context, sharpens their instructions, and prevents non-technical colleagues from making well-meaning but incoherent changes. Nitesh at Every is the example Shipper returns to. The model is the same one the labs use internally: pair every important agent with a real engineer who gardens it.

    PMs And Full-Stack Designers Win The Decade

    The two roles Shipper is most bullish on are product manager and full-stack designer. For PMs, the entire job of coordinating a team to translate vision into code collapses into a Codex session. A PM with strong product instincts and a little technical literacy can now prototype, iterate, and even ship. The example is Marcus, formerly a PM at Axios, who took a year to fully internalize AI and now ships faster than most engineers. For designers, the model is similar. The Friday-night-side-project designer who used to be stuck explaining a vision can now build the vision themselves, with their own taste fully expressed. The scarce skill in both cases is the same: judgment about what to build and the courage to decide it is good. Execution capacity is no longer the constraint.

    The Senior Engineer Benchmark And What Models Still Miss

    Shipper has built his own benchmark to test whether coding models can actually do senior engineering work. GPT-5.5 scores around 62 out of 100. Real senior engineers sit closer to 85 or 90. The gap is not in syntax or test pass rates. It is in the willingness to step back, see that a piece of code is fundamentally the wrong shape, and rewrite it from first principles. Models almost universally patch locally. They take the instruction at face value, accept the existing code as a constraint, and optimize within it. A real senior engineer ignores the prompt when the prompt is wrong. This is the durable moat for senior technical judgment, and Shipper expects it to remain visible for at least another year of model releases.

    AI-Generated Writing Goes Mainstream

    Internal writing inside companies is quietly becoming AI-first and Shipper thinks it should. Quarterly plans, status updates, PR descriptions, strategy memos, recruiting outreach, most internal email. He runs his own inbox through GPT-5.5 and Codex and says he would honestly prefer if the recipient knew. The point is not that AI is a better writer in some absolute sense. The point is that most humans are not very good at these specific genres, and the model produces a coherent, structurally sound first draft that a human can guide and approve. The constraint is honesty: you read it, you understand it, you stand behind it. Public writing, like the newsletters Every publishes, still demands a human voice. Internal communication does not, and treating it as if it did is a tax on the organization.

    The CEO And Middle Manager Lag

    Shipper points to a population that has largely escaped AI adoption: senior leaders and middle managers. They have staff to do the work, so they have not been forced to pick up the tools personally. He thinks this is the single largest pocket of latent disruption coming in the next year. Your company will only go as far as your CEO goes in AI, because every decision about where to deploy agents, where to hire, and how to restructure work flows downstream from leadership taste. A leader who has not personally lived inside Codex or Claude Code for a few weeks cannot make those calls well. Expect this to flip fast and to become a visible career liability for executives who do not adapt.

    Ride The Models

    The closing advice is the simplest. Ride the models. Use AI for whatever you actually do. Try every new release the day it lands. Most of the professional anxiety around AI dissolves on contact with the work, and most of the durable advantage in the field belongs to the people who do this one thing consistently. Shipper notes that the edge of AI does not live in San Francisco. It lives wherever a curious operator meets a real workflow and notices something nobody at the labs has yet. A PM in Iowa willing to spend a Tuesday night exploring Codex can find capabilities researchers have not surfaced. Pair that with his motto, do things worth writing about and write things worth reading, and you have most of an operating system for the next two years.

    Notable Quotes

    “The AI job apocalypse is not really a thing. I am super super bullish on PMs and full-stack designers.”

    Dan Shipper, opening his contrarian thesis for the conversation

    “I’m simultaneously extremely AI pilled and very bullish on humans. Automation is a lie. Every agent needs a human.”

    Dan Shipper, on holding both sides of the AI debate at once

    “What models do in general is they make yesterday’s human competence cheap. And so, it becomes commoditized. It’s not valuable anymore. What humans do is we go in there and we’re like, yeah, we have all this frozen human competence from yesterday, how do I use this to make something new and interesting.”

    Dan Shipper, articulating the core engine behind his anti-apocalypse thesis

    “I would buy SaaS stocks right now. The SaaS apocalypse is dumb. What agents do is increase the number of users of SaaS, not get rid of it.”

    Dan Shipper, calling the consensus SaaS-is-dead thesis directly wrong

    “We speed ran the CLI era. It was nice while it lasted, but I think CLIs are over.”

    Dan Shipper, on why the terminal-first agent moment is already done

    “Most of my email is written by GPT-5.5 and Codex right now. And I honestly would prefer it to say that it’s coming from GPT-5.5.”

    Dan Shipper, on the new etiquette of AI-assisted communication

    “The edge of AI is not in San Francisco. The edge of AI is wherever AI meets a real human doing something.”

    Dan Shipper, on where the actual frontier of the field lives

    “The only thing you need to do is ride the models. And that means use them for whatever it is that you do.”

    Dan Shipper, distilling his career advice for the next two years

    “Do things worth writing about and write things worth reading.”

    Dan Shipper’s closing motto, lifted from his own operating system at Every

    Watch the full conversation with Dan Shipper on Lenny’s Podcast here. The re-interview to score these predictions is scheduled for roughly May 2027.

    Related Reading

    • Every. Dan Shipper’s company and the live laboratory for almost every prediction in this conversation, including Spiral, Cora, and Claudie.
    • The Allocation Economy by Dan Shipper. The earlier essay that frames humans as managers of AI labor and underpins much of the gardening-the-agent thesis here.
    • Claude Code by Anthropic. The agent surface Shipper called correctly last year and one of the two environments he predicts will become the new operating system for work.
    • Codex by OpenAI. Shipper’s current daily driver and the visual, multi-pane agent environment he uses for almost everything from coding to email.
    • The Writing Life by Annie Dillard. The book Shipper makes every Every employee read, and the source of the company’s stance on writing as a tool for noticing the future.