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If you’re new, not yet a subscriber, or just plain missed it, here are some of our recent editions.

🧶 Five Examples Of Founder Scrappiness. Examples of digging in when times are tough by some of the greats.
🎯 Leading Intercom’s AI Transformation. Des Traynor on zero-to-one mess, AI momentum, and leading with intent.
🎄 A Look Back At The Year That Was. Wrapping up 2025, with a look towards the future.

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Dark & Full Of Terrors (2026 Predictions)

As years tend to do, 2025 brought us much and more. In January, the big Orange guy became Commander in Chief of the U.S. for the 2nd time; shortly after, we had Liberation Day, riots and ICE raids, JD Vance killing the pope (jokes), and the murder of Charlie Kirk.

Technology went bananas again, kind of. AI ripped, but now the daily chat is that we are in bubble territory, Nvidia hit $5 trilly for a brief moment, and DeepSeek gave Silicon Valley a mini heart attack. On the non-AI side of business, tech and media—also known as the Flea Bottom economy—Deel became a spy agency, the media wars continued as one trust fund baby took on the world, and the IPO market came roaring back. Oh, and Taylor Swift got engaged, breaking the hearts of stalkers all across the globe.

Today, I will outline a few predictions for the coming year. Who will rise, who will fall, and what will our weird and wonderful world look like 12 months from now as we round into 2027. A caveat: I am certifiably unqualified to make a lot of these predictions—possibly all—so take them with a grain of salt. Here they are.

Last year’s scorecard

Before we dive in, let’s take a look at how I did on last year’s predictions. You can find a detailed write-up of how I scored these in a piece I wrote just a week ago if you’d like to go deeper.

I’d say I did reasonably well overall. None of the predictions were really going out on too much of a limb, but even so, I’d call the last set relatively correct.

1/ Tech in general continues its heel turn

We have a significant PR problem on our hands across the technology industry. Thanks to the growing wealth divide, Elon and DOGE, AI doomerism, prediction markets, and the big tech oligarchy narrative, the general population is looking at tech through Zohran-colored glasses.

Although I don’t have predictions of the burning of OpenAI’s offices or any other such ‘Hey, my Tesla is on fire’ type moments, I expect this trend to continue into 2026. Our job, as people in and around tech, is not to fight back, but to show leadership. Ship products that actually help people, pay people fairly, and offer equity. Oh, and stop calling people 'resources' might help too. Give them a reason not to hate us.

2/ AI continues to move us out of caves

In the last 50 years alone, technology has brought us: personal computers, the internet, smartphones, GPS, streaming entertainment, electric vehicles, mRNA vaccines that saved millions of lives, instant global communication, cloud computing, CRISPR gene editing, renewable energy at scale, e-commerce that delivers anything to your door in 24 hours, video calls that made remote work possible, and the ability to access the sum of human knowledge from a device in your pocket.

Go back further, and you will find a few other handy inventions like fire, agriculture, writing, and the wheel. Technology is the sole reason we are not rubbing sticks together in caves.

This will be the year AI has its true breakout moment: drug discovery, disease detection, robotics, and developer productivity. Pushing back against AI doomerism will be slow but steady positive momentum in everything that matters.

Overall productivity will drive real GDP growth across the globe. Although specific industries will be heavily affected (human drivers, for example), businesses that become more efficient don’t capitalize on said efficiency with mass layoffs, but instead do what they always do: invest in growth.

_{*If we play our cards right, with the help of AI, we’ll all be living on these O'Neill Cylinders in a few decades.}

My prediction is that, although doomerism will continue unabated, AI will have created more jobs than it has destroyed by the end of 2026.

3/ Australia + NYC’s social crackdown spreads

Australia recently showed global leadership by banning social media for children under the age of 16, and New York City followed suit by passing a bill requiring platforms to place warning labels on their apps (something psychologist Michael Inglis and I predicted 12 years ago on my old podcast).

I'm not actually convinced these regulations will work. But I'm over the moon anyway. Not because they'll immediately fix social media's damage to kids—the addiction, depression, and suicide rates—but because they create friction for Meta, TikTok, and Snapchat. Australia and NYC led the way. France has announced they plan to follow Australia, and many other countries will follow.

4/ Prediction markets become the next tech behemoths

Gambling hijacks the same reward circuits that we evolved for survival, turning uncertainty into crack cocaine for your dopamine system. Prediction markets are the worst type of gambling, as users delude themselves into thinking they are ‘forecasting,’ which feels somewhat more rational. As our brains continue to rot away, prediction markets will continue to take hold.

The worst part is that it’s a very interesting technology. It’s the absolute gutter-trash of our morality, but just like social media, this weed will spread far and wide. Polymarket and Kalshi will see their valuations 2-3x in 2026, deepening their cultural relevance, while Robinhood, DraftKings, and others continue to open markets for anything and everything.

5/ And get banned by the EU

Unlike the U.S., where Don Jr. has, put mildly, ‘ties’ to Kalshi and Polymarket and the administration is pro-crypto, the EU has no political incentive to accommodate these platforms and has banned them in many member states.

ChatGPT informs me that it’s difficult for the EU to blanket ban prediction markets, as such a ban would require it to enforce a single legal definition across all member states, which is politically and legally challenging. But if we know anything about Europe and regulations, there is a way.

6/ The ‘WeWork’ of human connection gains traction

In its heyday, WeWork had this incredible sheen of ‘bringing people together.’ And with a charismatic charlatan-like leader in Adam Neumann, venture capitalists were famously falling over each other to fund it. I predict 2026 will be the year we see a raft of IRL-type startups get funded. Why? Because the combination of social media with our COVID hangover has left us lonely as hell.

Think wethrowparties.com (sorry, the domain is already taken), a party marketplace where dedicated party hosts plan and prepare themed parties that users can sign up to join. Kind of like Meetup meets a frat party. Speaking of Adam Neumann, I actually always loved the WeLive idea, which is somewhat analogous to his mysterious new company, Flow. WeWork vibes, but in your apartment building. Incredible right?!

7/ ‘Founder brand’ matures into ‘founder media’

First came brand, then came employer brand, and then founder brand. 2026 will be the year that things heat up even more as the job of a founder CEO becomes more and more communications-heavy. How do you show up on podcasts? Do you have a social following? Do you own your own media channels?

I believe we are about to see an explosion of founder media. Cheeky Pint, with Stripe’s John Collison, is an excellent example of a founder who owns their own channel (or show, as it’s technically hosted on Stripe’s YouTube). Collison is a rare case in 2025; but not for long. Another example is California Governor Gavin Newsom, who launched his show, This Is Gavin Newsom, earlier this year. Both Collison and Newsom are betting on the power of the parasocial relationship to build trust with their audiences. I expect more of this in 2026.

8/ Theo Von becomes the biggest podcaster in the world

I was talking with a friend recently about the rise of podcasts. He had just recommended Shane & Matt’s Secret Podcast, Sourcery, and others to me, then the topic of Rogan came up. “I honestly love him, but I can’t listen anymore,” he said, “I find his conspiracism just too much for me to handle.” This is how I’ve felt about Rogan for years. I think he’s one of the kindest-hearted guys on Earth. But he’s seen through a partisan lens now, which Theo is not.

I have listened to Theo’s podcast since he did it solo from his kitchen bench. I’m not sure I’ve seen a more empathetic guy, who also happens to be the funniest man in the world right now. Theo, as opposed to what the liberal media says, is great at sharing both sides of the story. Recently, he had a Jewish-Israeli rabbi on the show, followed by a Palestinian comedian the next. He interviewed Trump and JD, but also interviewed Bernie Sanders and Ro Khanna. I expect Rogan’s show to recede, and in 2026 (or the subsequent years), the Rat King to take the crown of world’s biggest podcaster.

9/ Trump starts a war with Venezuela (which spreads to Colombia)

As I mentioned in the introduction, I’m wholly unqualified to talk about geopolitics in any meaningful sense. That being said, Trump and the U.S. are for sure going to start a war with Venezuela. There doesn’t seem to be any sense to it from any vantage point I have seen or heard, apart from oil, of course.

I also predict some degree of escalation from other Latin American powers. Mexico’s Claudia Sheinbaum has already gone on record as opposing U.S. intervention in the region. But, the most likely escalatory country might be Colombia, for the pure fact that its leader, Gustavo Petro, not only alleged that Trump is a pedophile in a recent speech, but also sits firmly on the far left politically. Trump has already threatened Petro that he is “next.” Considering the President’s vengeful streak against his political enemies, I could see this spilling over.

10/ Brainrot and conspiracism on the right continues

The thing that keeps me up at night most in 2025 is brainrot and conspiracism. I have many friends and family members who have lost their grip on reality and can no longer think critically. Everything is a globalist conspiracy. Look at the top podcasts in the world; you have Rogan, Tucker Carlson, and Candace Owens all in the top 10. Not to mention, Fuentes will continue to rise, Elon will continue to devolve on Twitter, and RFK will anti-vax. What I find interesting is that in 2025, it’s much more of a right-wing phenomenon, with 35% of Republicans prone to embrace conspiracy theories, 20% of Independents, yet only 14% of Democrats.

11/ Empathy makes a roaring comeback (as MAGA recedes)

I don’t know how to make this prediction concrete, but I predict that empathy will make a comeback. The Trump Administration will continue to mock immigrants, sure, but it won’t be received as well as it was in 2025. We are already seeing massive pushback from what the left calls the Manosphere, with Rogan, Andrew Schulz, Theo, and others all backing away from their 2025 endorsement. Add to the fact that MAGA is fracturing from infighting, and they are losing members—the number of Republicans who identify as MAGA, instead of traditional Republicans, has dropped 10-21% (depending on the source) since its peak in March—I predict a continuation of this and somewhat of a return to, shall we say, nicer values.

12/ Eat/tax the rich gathers momentum

In Thomas Piketty's famous book, Capital in the Twenty-First Century, he argued that global inequality will continue unabated to dangerous levels for one straightforward reason: r > g.

When the rate of return on capital (r) is greater than the rate of economic growth (g), wealth inequality spirals: Inherited wealth grows faster than earned income, the rich get richer automatically, not through merit or productivity, and we enter into a neo-Gilded Age of what Karl Marx would see as the proletariat versus the bourgeoisie.

Elon may become a trillionaire in 2026, and with inflation and rising cost-of-living pressures worldwide, this will be one of the catalysts for the movement gathering momentum. Don’t expect this to go away; expect a revolution.

Summary / Future

2026 will be a year of contradictions. AI will solve real problems while people fear it. We'll regulate social media while prediction markets explode. Empathy will resurge while conspiracism spreads. The decisions we make in 2026—as founders, leaders, and citizens—will determine whether technology remains a force that pulls us out of caves or pushes us back into them.

My bet is that we'll get a bit of both. Dark times ahead? Maybe. But also full of opportunity for those willing to lead with empathy, build with purpose, and think beyond the next quarter. Here's to 2026. Let's make it count.

Extra reading

• New Year, New Newsletter - Our 2024 Plan - January, 2024

• Chasing Lenny & Open Source CEO - Year 1 Recap - March, 2024

• My 12 Takes Of Christmas - December, 2024

• A Look Back At The Year That Was - December, 2025

And that's it! You can follow me on Twitter and LinkedIn, and also don’t forget to check out Athyna while you’re at it.

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TOOLS WE RECOMMEND 🛠️

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