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.

LINKS to a few 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)
thevibemarketer.com (community for people into marketing with AI)
ideabrowser.com (the #1 place to find startup ideas and trends on the internet)

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.

i found a github repo that lets you spin up an ai agency with ai employees

engineers, designers, growth marketers, product managers

each role runs as its own agent and they coordinate to ship ideas

10k+ stars in under 7 days

1. engineering (7 agents)
frontend, backend, mobile, ai, devops, prototyping, senior development

2. design (7)
ui/ux, research, architecture, branding, visual storytelling, image generation

3. marketing (8)
growth hacking, content, twitter, tiktok, instagram, reddit, app store

4. product (3)
sprint prioritization, trend research, feedback synthesis

5. project management (5)
production, coordination, operations, experimentation

6. testing (7)
qa, performance analysis, api testing, quality verification

7. support (6)
customer service, analytics, finance, legal, executive reporting

8. spatial computing (6)
xr, visionos, webxr, metal, vision pro

9. specialized (6)
multi agent orchestration, data analytics, sales, distribution

what i like about this approach is the framing

instead of one big ai agent trying to do everything, you structure it more like a company. specialized agents, clear responsibilities, workflows between them

im curious to see what this actually feels like in practice and if its any good (do your own research)

but as always will share what i learn in public on LI, X, IG and my pod the startup ideas podcast

one thing is for certain and it reminds me

the future belongs to those who tinker with software like this

CEO of Late Checkout, a portfolio of internet companies

4000 people laid off today at Block (almost half the company) and the reason is AI

“we're already seeing that the intelligence tools we’re creating and using, paired with smaller and flatter teams, are enabling a new way of working which fundamentally changes what it means to build and run a company. and that's accelerating rapidly” - jack dorsey

this is unfortunate yet just the beginning. hundreds of thousands if not millions will lose their jobs.

New jobs will be created and many will become entrepreneurs and build ai native businesses

send this to a friend

note: i've noticed in uptick on http://ideabrowser.com of people looking for startup, ideas trends who've been recently laid off

"Things I wish someone told me before I almost gave up on OpenClaw"

the future of building saas

1/ start with a sub-niche inside a big market
2/ map their daily workflow end-to-end
3/ identify where money changes hands
4/ spot the repetitive mechanical steps
5/ quantify the cost of those steps
6/ create scroll-stopping content around that workflow
7/ study which posts get saves, replies, and dms
8/ double down on the organic angles that convert
9/ run paid ads on proven organic winners
10/ capture emails from day one
11/ manually perform the workflow yourself
12/ document every step precisely
13/ separate judgment tasks from mechanical tasks
14/ turn mechanical tasks into structured agent workflows
15/ design agents to complete full tasks, not suggestions
16/ connect to real tools: email, slack, notion, crm, stripe
17/ add orchestration, retries, and verification checks
18/ store user preferences + long-term memory
19/ launch narrow with high-touch onboarding
20/ publish measurable proof: revenue, hours saved, errors reduced
21/ move pricing from per-seat → per-task
22/ shift to outcome pricing tied to revenue created
23/ increase pricing as value compounds
24/ expand into adjacent workflows within the same niche
25/ orchestrate multiple agents across the full lifecycle
26/ build switching costs through data + memory
27/ turn power users into public case studies
28/ hire operators from inside the niche
29/ reinvest profits into distribution + product depth
30/ become the default execution layer for that sub-niche

this is how 3 person teams build 100m companies

what a time to be building

note: find startup ideas on ideabrowser.com

how to build an ai native vertical saas in the claude cowork era:

1. pick a sub-niche inside a large, profitable market
2. map one recurring workflow that drives revenue or saves time
3. write the workflow step-by-step like you’re training an intern
4. separate mechanical steps from judgment calls
5. connect claude to the actual stack: crm, sheets, inbox, slides, contracts
6. remove exports and copy-paste from the process
7. collapse raw data → reasoning → finished output into one session
8. store every output so context compounds over time
9. turn your best prompts into named, reusable commands
10. build memory around the niche (not generic instructions)
11. package the result as a finished outcome
12. price per report, per memo, per meeting, per deliverable
13. publish the workflow collapsing in real time for distribution
14. use organic traction as signal before running paid ads
15. expand into adjacent workflows inside the same vertical
16. layer governance and approvals where required
17. become the default operating layer for that sub niche
18. repeat the model in the next vertical once memory and distribution compound
19. good times

claude can now sit inside real enterprise tools:

– google workspace
– excel + powerpoint
– crm systems
– prospecting tools like apollo + clay
– traffic data like similarweb
– contracts via docusign
- etc etc

that means the model sees the full workflow

the opportunity for you

find a niche.
collapse a workflow.
package the outcome.
own the memory.
expand from there.

that’s how ai native saas gets built now

it's a wonderful time to be building

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FUN FACTS

 9️⃣ Enneagram: I’m a #9, The Peacemaker (also known as the easygoing and emotionally stable)!
 🇳🇮 My family roots are in Nicaragua
🌮 My favorite food is tacos
💪🏽 Kettlebell workouts any day
🤼‍♂️ My favorite WWE storyteller is The Rock
👨‍👩‍👧 Proud husband and dad.

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Greg Isenberg

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The Battle

Greg Isenberg

Cesar Romero 🎙

Followers

Posts

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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