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.

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

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.

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

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.

These 15 techniques pretty much 10x the quality/output of ANYTHING you vibe code with Gemini 3 etc

Pliancy

VP of Business Operations

As the VP of Operations at Pliancy, I collaborate with our people to ensure they have the best experience working and thriving in their role. I work cross-functionally to ensure our team and culture drive home Pliancy's vision with newer initiatives like learning and development. I also believe in data-driven decision-making and insights. I believe in aiding teammates at all levels of Pliancy to lead together and build solutions for the greater good. We use these practices to improve operational management and empower our people to challenge the status quo in our industry.

VP of Operations

Director Of Operations

Outpost Security

Outpost Security is a cybersecurity advisory brand launched by Pliancy. As the founding executive, I led the vision, positioning, and rollout of the offering — working across strategy, design, operations, and GTM execution.

Founding Executive

FOG Ventures

FOG Ventures was created to invest and support innovative founders that are helping create toolbox 2.0 for the modern day operator. We’re backed by the world's top COOs & CFOs at tech’s most prominent startups. We do not just invest in what we believe in — as active operators, we’re investing in products we actually love and use.

Investor

Operators Guild

Operators Guild is an independent, invitation-only group of the world’s top finance, operations, and high-growth technology leaders. Scaling a company is hard. We are working together to share best practices, help one another solve similar problems, and invest in the operator community. We meet and connect regularly to support each other as we create the next generation of high-growth companies and company leaders.

Member

RiseTech

RiseTech provides managed IT services to small and medium sized businesses in Silicon Valley, CA to help them get the most out of their technology.

Founder

Sereniti IT Services

Operations Manager

Santa Cruz Community Credit Union

Branch Manager

Member Service Supervisor

Member Service Representative

VP of Ops @ Pliancy | Empowering Tomorrow's Technology Leaders

Chaos is a choice. I build the opposite.

I’m an operator who thrives in ambiguity — the kind where things don’t exist yet, but need to.
I build the systems, functions, and teams that bring order, momentum, and clarity to complex work.

At Pliancy, I lead business operations and finance for a mission-driven IT services firm supporting the operators, founders, and investors building the next generation of breakthrough companies. I also launched Outpost Security — a new advisory brand designed to help clients rethink security without the fear-mongering and jargon. I build from scratch, lead with context, and scale what works.

My work lives at the intersection of systems thinking, strategic execution, and long-term trust.
Whether it’s designing workflows, rallying teams, or turning loose ideas into operational engines, I’m drawn to problems that don’t come with a playbook.

I’m data-driven but people-centered. I persist with patience. I challenge the status quo without burning the bridges behind me. I love big ideas — but I’m obsessed with the hard, quiet work of actually making them happen.

If you’re building something new, solving hard problems, or rethinking how your org works — let’s connect.

taplio

The Battle

Greg Isenberg

Patricio Pace, MBA

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taplio

The Battle

Greg Isenberg

Patricio Pace, MBA

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Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Greg Isenberg's LinkedIn Performance

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