Greg Isenberg

CEO of Late Checkout, a holding company for community-based businesses

I'm the CEO/Co-Founder of Late Checkout, a holding company with a portfolio of internet businesses. 

Previously, I was the Head of Product Strategy at WeWork, an Advisor at TikTok and an Advisor at Reddit. I was the Founder/CEO of Islands, a messaging/community app that was acquired by WeWork.  I was the Founder/CEO of 5by, a leading video discovery app which got acquired by StumbleUpon.  I helped build one of the internet's most popular financial education communities Wall Street Survivor (acquired). 

I've helped build communities and technology products for brands like Microsoft, FedEX, NASCAR, TechCrunch and Wordpress. 

I've been featured on places like Vanity Fair, Forbes, Mashable, Fortune Magazine, L.A Times and have won Webby Awards.

I share my thoughts on Twitter @gregisenberg (say hello).

LINKS to some of my companies in my holdco🔗

gregisenberg.com (my guides, podcast, sign up to my weekly newsletter for updates)
latecheckout.agency (product design agency that works with executives from Dropbox to Nike to Shopify)
boringmarketing.com (agency to get you ranked on google)
boringads.com (agency that creates profitable ad campaigns)

CEO & Co-Founder 

Late Checkout is a holding company that builds, acquires and incubates cash-flowing businesses that are powered by internet audiences and communities.

Learn more about our businesses at https://latecheckout.studio and work with us.

Apple JUST quietly announced something that’s a lot BIGGER than it looks: "the Mini Apps Partner Program"

Apple is admitting that the future of software is embedded, lightweight, vertical mini-apps distributed inside bigger app

For founders who want to make $$ building apps:

1. Apple just legitimized the “superapp” model for the West.

China has WeChat mini-programs. India has PhonePe Switch. The West has… nothing. Apple just opened the door. You can now run HTML/JS mini-apps inside a native host and earn 85% on qualifying purchases. That’s Apple-sanctioned platform piggybacking.

2. Distribution arbitrage becomes real again.

You don’t need to convince users to download your app. Just partner with a host app and drop in a mini-app. This is a cheat code for early traction. Think: travel apps hosting niche tools, fitness apps hosting mini workouts, marketplaces hosting micro-utilities.

3. Apple is creating a new economy layer: “embedded SaaS.”

Imagine: CRM mini-apps inside vertical tools. Math solver mini-apps inside education apps. Calendar mini-apps inside productivity apps. The TAM for tools that don’t need standalone installs just went vertical.

4. Developers get an 85% revenue share.

This is Apple basically saying: “We want this ecosystem to grow, and we’re willing to cut our take rate.” When Apple lowers its cut, I pay attention because they see a platform shift coming.

5. AI makes this 10× more important.

LLM-powered micro-apps (calculators, planners, agents, coaches, niche utilities) are tiny by design. They’re perfect mini-apps. Apple just created infrastructure for AI-native micro utilities to live inside bigger apps with built-in commerce.

6. Host apps become new “distribution landlords.”

If you own an app with traffic, you become a platform. You can host mini-apps, take a cut, and build a developer ecosystem around you.

 It’s a new monetization model for existing apps with audiences.

7. This unlocks a wave of second-order opportunities.

- Agencies helping apps become mini-app hosts
- Mini-app dev shops
- “Shopify for mini-apps” toolkits
- Mini-app marketplaces
- Analytics for mini-app performance
- Discovery engines for mini-apps
- For more startup ideas/trends... sign up to https://ideabrowser.com 

TLDR;

Apple just turned every high-traffic app into a potential superapp and every indie developer into a potential platform partner.

The App Store is becoming modular, composable, and layered. The next decade of consumer apps will look less like standalone products and more like ecosystems stitched together with mini-apps.

This is quietly one of the biggest distribution unlocks in years.

CEO of Late Checkout, a portfolio of internet companies

2026 AI predictions

1. SaaS and agents merge completely in 2026. Every SaaS product becomes an agent platform, and every agent platform builds SaaS features. The ones that don't adapt die or get bought for pennies. 

2.  Google continues to crush in 2026. OpenAI feels the heat. Doubles down into becoming a social company, lots of features that you'd think a Meta would create

3. Infinite-context entertainment kills pilot season. Netflix lets you continue cancelled shows just for yourself. AI generates new episodes of The Office or Friends dynamically based on your mood.

4. Micro-companies explode in volume and weirdness. Tiny AI-augmented businesses serving tiny online tribes become a real career path.

5. Personalized nutrient cocktails created by generative AI replace traditional OTC wellness. 

6. AI agents get their own wallets. Agents transact with each other using crypto for data, API calls, and compute. T

7. The return of the invite-only web. To escape the bot-flooded “dead internet,” the best platforms become gated and reputation-scored. T

8. Search is replaced by answer synthesis. Browsers read 50 sources and give you the conclusion. 

9. Hardware returns with a vengeance. Browser-based AI feels limiting, so AI pins, earbuds, and ambient devices take off. The smartphone’s decline becomes visible.

10. Google, Apple, and OpenAI accidentally build the new internet. Instead of browsing websites, people live inside model environments.

11. Personalized education unbundles the university. 

12. The first agent-driven media companies appear. Daily shows, newsletters, and entire channels run autonomously, with one human editor.

13. Local LLMs become the new privacy shield. A major hack scares the world and everyone shifts to on-device models that never touch the cloud.

14. The rise of analog status. “Analog” becomes the ultimate flex. Film cameras, handwritten notes, and acoustic instruments explode in value

15. Prediction markets replace user research. Companies test product ideas on 10,000 AI personas/know the outcome before writing code.

16. Software becomes disposable. Apps are generated, used for 72 hours, and deleted. 

17. A major university drops its computer science degree. It’s replaced by “agent systems,” “model psychology,” and “human interface architecture.”

18. Infinite apps replace the App Store. Micro-apps are generated inside ChatGPT or Gemini and traditional downloads collapse.

19. The first sovereign AI trade war begins. Nations ban the export of foundation models and treat foreign AI use as espionage.

20. Blue-collar trades become safe havens. Electricians, plumbers, and HVAC techs see wages skyrocket as white-collar automation accelerates.

21. The fastest wealth creation path in 2026 is spotting assets mispriced because people underestimate AI’s speed. 

22. 2026 should be an interesting year for AI. What do you think?

Note: grab a startup idea, a trend, and some prompts from ideabrowser.com and happy building.

late-checkout

the-room-where-it-happens

islands

dear founders,

build like the clock’s running out. the window is open but it won’t stay. for the first time in history, you have free distribution from social platforms and infinite leverage from AI tools. you can reach millions without permission.

the internet is handing out unfair advantages to anyone bold enough to use them so...

ship before you understand it. launch "ugly". talk to users every day. build what you wish existed. best ideas are the most obvious painful. go niche. no, go superniche. vertical is your moat.

clarity comes from commits. half your roadmap might be ego, delete it. make ugly things until they work. share prototypes that break.

kill what doesn’t grow. use AI as leverage, not decoration. test ten things before breakfast. delete your roadmap. double down on what works. design for clarity, not cleverness. brand before code. write daily. post your lessons.

find your first hundred users manually. distribution is the new product. attention is the new funding. taste is the new code. build small cults. scale later. automate boring things. keep the human parts human. study why things spread. study why things die. 

pricing is positioning. aesthetics are trust. make people feel something. ignore haters. build in weird corners of the internet. break things publicly. pivot loudly. consistency compounds. only raise VC if you dream of going IPO one day. otherwise, cash-flow is your BFF.

your network is distribution. your story is marketing. your design is psychology. ship like it’s day one. iterate like you’re behind. stay obsessed. learn faster. think longer. risk embarrassment. make noise. build the thing that keeps you up at night. money follows obsession. stay in motion. stay loud. stay building. distribution is an art form now.
 
AI makes it easy to make things; the hard part is making things that matter. build like the world’s ending in a year but your idea has to outlive it 

we’re living in a window of maximum leverage and minimum permission

im rooting for you.

best,

greg isenberg

just another founder rooting for you

note: find startup ideas at ideabrowser.com to get your creative juices flowing

A few days ago I hit 500,000 subscribers on YouTube after posting 705 videos for 4 years.

CRAZY because I also wanted to quit like 500k times in the early days.

I still remember in 2022 recording in a tiny closet with my laptop balanced on a laundry basket, trying not to wake anyone up, wondering if the world needed another dude about startups and convincing myself that maybe a few hundred people would find it useful if I kept going.

And for a long time, I'd be happy if 1000 people watched my stuff. It took me 12 months to hit 10k subs, 12 months to hit 20k subs, 12 months to hit 100k subs and 12 months to hit 500k months.

Somewhere in the middle of the bad lighting, bad audio, and bad confidence, founders started messaging me.

They were using the videos to make decisions, ship products, and try things they had been avoiding for months.

That was the moment I realized I had to keep going because something I made in a tiny closet was suddenly showing up in someone else’s life at exactly the right moment, and when you feel that connection for the first time, it changes the way you see the whole project.

It also made me realize how many builders are out there trying to make sense of AI, trying to design from scratch, trying to turn weird ideas into tiny businesses, trying to find leverage in a world that moves faster than anyone ever prepares you for.

(here is the channel link if you want to sub https://lnkd.in/ebpMJaHS)

The 500K is cool i guess, but the cooler part is the collective energy around it  thousands of strangers learning, experimenting, arguing, DMing, building, and pushing their luck a little harder each week.

Being a small piece of that current feels like the real milestone. That's the cool part.

Half a million people now show up. Millions of views a month. Millions of minutes. A giant, invisible room of people who decided something I said was worth their attention.

That still stops me and i want to thank you from the bottom of my heart.

I’m still here with the same goal I started  the channel with:

Be useful, share a BOATLOAD of startup ideas and growth tactics, serve up tutorials on how to use AI to do big things and watch some of you take those ideas and become wildly successful in your own way.

Thanks for being here. I can't say for certain I know what 2026 and beyond hold for me  The Startup ideas Podcast.

If you keep going, I'll keep going.

Let’s see where we go next.

We’re about to see the largest boom in micro-companies in history. 

1 person to 10-people businesses that generate real cash, serve tiny but passionate communities, and operate with leverage (organic social, AI etc) that used to require mega teams

Once people realize they can earn a meaningful living by building something tiny and strange that fits a community they actually understand, everything shifts like ambition, lifestyle, career arcs, even how people think about “success.”

Some people will build two or three of these.
Some will build twenty.
Some will build one that accidentally becomes big.

You can literally feel the shift happening.

Just an increasing number of people quietly opting out of the traditional paths and choosing to build a life around small companies that actually work.

i woke up this morning, opened Stripe's BFCM site, and had one of those strange founder moments where the internet folds in on itself. you scroll past giants like Cursor, Crumbl Cookies, Pepsi… and then your own holdco site is sitting right there in the mix like it snuck into the VIP section without anyone noticing.

I saw the Late Checkout logo this AM and I had to ask myself if I had my coffee today.

it’s a surreal feeling because Stripe is one of those companies you quietly build your entire business on. you use it every day, you never think about the infrastructure beneath you, and then suddenly the people you admire are putting you shoulder to shoulder with brands you’ve ordered from, learned from, or competed with.

our portfolio : ideabrowser for startup ideas and trends, LCA for design firm for the AI age, boring marketing for marketing with AI. 

Stripe powers a lot of it. subscriptions, sales, most experiments, most silly landing page we spin up at 2am.

so seeing us on their BFCM site felt like a full-circle moment. a tiny reminder that people are watching what you’re building even when your head’s down doing the work.

grateful, a little stunned, and fired up to keep going.

note: and if you want to build out startup ideas with AI, our ideabrowser.com black friday sale is live powered by the same Stripe rails that brought this full-circle moment to life. for more details on the sale ideabrowser.com/pricing

30 ways to find your next $10K+ MRR idea for 2026:

1. Read GitHub issues and look for recurring pain points developers ignore.

2. Set Reddit alerts for “I wish someone would build…” and validate demand.

3. Build an agent around a single recurring vertical Upwork task that pays well.

4. Monitor API changelogs and build integrations the day they launch.

5. Summarize 1-star Chrome Store reviews with ChatGPT and fix the top three complaints. 

6. Audit browser DevTools to see what power users still do manually.

7. Reverse-engineer topProduct Hunt hits, then apply AI to improve them.

8. Read YouTube tutorial comments to see what viewers still can’t figure out.

9. Watch Twitch streamers and note what workflows interrupt their flow.

10. Scan job listings for repeated “must-know” tools; build easier versions.

11. Dig through graveyard from companies like Google and ship the best abandoned projects.

12. Implement new AI research papers as usable web apps.

13. Explore niche subreddits and find problems that appear every week.

14. Review SaaS feature requests and build what the big players delay.

15. Connect open-source tools that don’t yet talk to each other.

16. Track “Chrome extension for X” search volume to spot new demand.

17. Feed GPT the top extension descriptions and ask for adjacent product ideas.

18. Use Perplexity Deep research etc to mine  podcast transcripts on people's daily frustrations they’re telling you what to build.

19. Follow changelogs and tech-stack migrations of popular startups; build the missing glue.

20. Look at Zapier’s most-used zaps and each one could be an autonomous agent.

21. Track “AI for X” or “agent for X” search queries with SerpAPI.

22. Analyze public Notion templates and build vertical agents around them.

23. Browse LinkedIn for people describing manual data tasks and productize one.

24. Watch how startups use ChatGPT for customer support and make a vertical agent from it.

25. Rebuild niche directories (lawyers, therapists, realtors) as AI concierge services.

26. Create agents that plug into boring SaaS categories: procurement, compliance, HR ops.

27. Read changelogs from AI model providers; build tooling the day new capabilities appear.

28. Find spreadsheets that companies rely on and replace them with AI dashboards.

29. Identify agencies that charge per project and productize their work into recurring SaaS with agents.

30. I built a tool that automates a lot of this, http://
ideabrowser.com and we give away 1 free startup idea per day with paid plans for AI agents to help you. Maybe it'll get your creative juices flowing

TLDR;

– The next big idea is probably hidden in a comment thread.
– Every complaint online is a free focus group.
– Every repetitive task is a business model waiting for an agent.
– The internet keeps leaving clues, just gotta listen

MCKINSEY JUST DROPPED THEIR 2025 AI REPORT and HERE’S THE SUMMARY:

1/ 90% of companies “use AI,” but 67% are still stuck in pilot mode. Corporate AI theater is alive and well lol.

2/ 62% of orgs are experimenting with AI agents, 23% are scaling AI agents. Most are in tech and healthcare.

3/ The impact gap is massive. 64% say AI helps innovation, but 39% see real EBIT gains. 

4/ The high performers (top 6%) think bigger. They rebuild workflows, set growth goals, and invest real budgets not just POCs.

5/ Leaders who own AI personally are 3x more likely to scale it. Makes sense.

6/ The winners use AI to transform how work gets done, not just speed it up.

7/ The average company measures efficiency. The best ones measure how fast their agents can act.

8/ Risk management is catching up with 51% have already seen AI backfire, mostly from inaccuracy.

9/ The workforce impact is foggy. 32% expect cuts, 13% expect growth, everyone else is guessing.

10/ AI adoption is mainstream, but true transformation hasn’t started. Early days.

i think the best city to build a startup from is usually the city you as the founder are the happiest and can lock in the hardest

shopify started in ottawa. supercell from helsinki. spotify from stockholm etc

your output is tied to your environment, your focus, your happiness

everything is a wrapper.

money is a wrapper for time.
time is a wrapper for energy.
energy is a wrapper for attention.
attention is a wrapper for emotion.
emotion is a wrapper for storytelling.
storytelling is a wrapper for identity.
identity is a wrapper for belonging.
belonging is a wrapper for survival.
products are wrappers for problems.
brands are wrappers for trust.
AI is a wrapper for leverage.

HOW TO WIN IN THE AI AGE 

You are competing against people who copy what exists and let AI remake it.

Most design, writing and product work comes from AI copying existing references in generic mode, which is why the internet feels like an endless conveyor belt of bland.

The moment you push past that baseline and force the model to do something uncomfortable, you separate yourself from the entire curve. Giving it original ideas + references outside your niche. 

The people who win are the ones who insist on originality in a world that keeps asking for “good enough.” 

The reason this matters is because default effort produces default outcomes, and default outcomes disappear instantly in a feed that never stops moving. 

I bet these default startups have more and more friction standing out going further as AI makes startup making more like a machine.

People can FEEL the difference between something generated and something directed, between something assembled and something authored. AI will happily produce the average case forever, but it will never choose to take the creative risk that changes how something feels. And that's where the alpha is!!!

Anyone can generate. Almost no one curates, edits, reworks, reshapes, interrogates, or pushes until the thing becomes unmistakably theirs. 

The edge is in the taste you bring to the model, the choices you make that the average user will never even see, and the willingness to throw away nine versions to get to the tenth that feels alive.

In a world where everyone has access to the same tools, the only real advantage is the person who refuses to behave like a default setting.

There’s a whole new generation of founders who are going to buy businesses and turn them into holding companies with software and AI: 

how they’ll do it:

step 1: acquire niche business at an attractive price
step 2: create internet distribution to scale customer base
step 3: build AI-assisted software to increase margins/make product more attractive 
step 4: recycle cash-flow to buy more businesses

THANKSGIVING THOUGHT:

the measure of a good life is something I call the pinch me ratio.

it’s how often you pause in the middle of a normal day and think, “wow… I actually get to live like this.”

sometimes it comes from tiny things: a quiet hot coffee in the morning, sunlight hitting your office just right, the peace of knowing nobody owns your calendar.

and sometimes it comes from the big stuff, the moments where your 16 year old self would look at your life and say...

“are you kidding me? we get to do that for work!?”

those moments matter JUST as much as the small ones.

together they tell you whether you’re actually living the life you spent years trying to build, or just sprinting past all the parts that make it worth building.

when my ratio is high, everything feels aligned. when it’s low, it’s usually a sign I’ve drifted into autopilot.

this thanksgiving is a nice reset for the pinch me ratio. 

count the tiny and big things that make you pause and think “yeah, this is pretty great.” 

it’s a simple way to notice the parts of your life that are actually working.

i want you to have a good life.

keep going.

happy thanksgiving my pinch me people.

vibe coding is eating SaaS...this is probably happening more than we think

I’m obsessed with the new Google Gemini Pro 3

THE ONE STARTUP SKILL FOUNDERS IGNORE UNTIL IT’S TOO LATE: your burn, your cash, and your collections.

I didn’t take it seriously at first either. Everything always looked fine on the Google Doc. The dashboards were green, the weekly updates sounded good, and the financial model was always optimistic enough to buy a little confidence. Then I’d open the bank account and realize the truth lived there, not in the documents. That gap between the story and the balance was the thing that eventually forced me to build a simple way to stay close to the numbers, because nothing else was dependable.

Even with a strong CFO, I learned that as the founder you still need enough understanding to sense when something is drifting. Nobody cares about the survival of the company the way you do, and nobody feels the risk the way you do when it’s your money and your runway on the line. Staying close is self-preservation not micromanagement.

For me it starts with a Monday check-in where I update a 13-week cash view, look at the same five numbers, and spot anything that’s moving in the wrong direction. It takes fifteen minutes, and it prevents surprises. Friday is a short block to approve spend and chase invoices before they turn into real problems. Once a month I close the books with a checklist, run variance, and send a one-page summary that forces clarity instead of stories. Big decisions run through a bear/base/bull scenario so emotion doesn’t lead the company off a cliff. I keep a lightweight data room updated so opportunities never catch me unprepared. Corporate cards follow policy because trust doesn’t scale. And I think about dilution in months of runway, not in headline round sizes.

None of this is glamorous. It’s just consistent. And consistency is what keeps your mental picture aligned with what’s actually happening, not what you hope is happening. I’ve seen incredible teams with great products get blindsided because they weren’t looking at their numbers often enough and the drift caught up to them all at once.

If product/market fit is what gets you excited in the morning, this is the thing that lets you sleep at night.

Sharing it in case one founder out there is drifting more than they realize. 💸

Full whiteboarding session where I explain this in more depth is now live on YouTube below:

https://lnkd.in/eMcbss9r

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