Greg Isenberg

Late Checkout

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.

CEO & Co-Founder 

Reddit, Inc.

Advisor

TikTok

WeWork

- I defined and adjusted holistic technology product strategy for WeWork apps
- I joined WeWork via Islands acquisition where I served as Founder/CEO

Head of Product Strategy

Islands

Islands was a community platform for colleges. Imagine Discord but for college campuses.

Islands was backed by Greylock, Scott Belsky, Erik Torenberg, Howard Lindzon and others.

Founder & CEO (acquired by WeWork)

StumbleUpon 

I was on the StumbleUpon management team, with a focus on leading StumbleUpon video, corporate development and product advisory.

StumbleUpon was one of the largest social media websites by referring traffic. StumbleUpon was acquired by Expa.

CEO, 5by (Acquired by Expa)

The best videos on the internet, guaranteed. 

5by was the winner of one of the best apps of 2014 named by Google 
"​ 5by is my favorite app" - ReCode

CEO & Founder (Acquired by StumbleUpon)

Stock-Trak / WallStreetSurvivor

Wall Street Survivor is the most popular stock market simulator on the internet. It was acquired in 2017

Stock-Trak is the web’s leading financial simulation for the college-level investment classes and allows students to manage a virtual portfolio of stocks, options, bonds, futures and mutual funds.It is used by over 80% of the top U.S. Business Schools. It was acquired in June 2013.

Partner, VP Product & Investor (Acquired)

StressLimitDesign

stresslimitdesign was a product design shop focused on helping brands like Microsoft and Fedex build fantastic digital experiences.

I was in charge of business development, marketing and helped with product/marketing strategies for clients.

Partner & Chief Marketing Officer

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

I'm the CEO/Co-Founder of Late Checkout, a holding company building businesses powered by community. 

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)

so yesterday, i meet this entrepreneur and they hit me with the line 'we don't do ads. all our growth is 100% organic'

and there's this awkward pause... you know the one. they're waiting for me to go 'wow, you're so pure and noble'

but in my head i'm like 'weird flex but ok'

look, i get it. starting organic is smart. build that audience, community, newsletter and put in the hard work. i always start organic personally.

but acting like never touching ads is some kinda entrepreneur merit badge feels off to me.

ads aren't the devil. they're a tool. a pretty damn useful one at that.

let me break it down:

1. ads force you to nail your messaging. you can't afford to be wishy-washy when you're paying for eyeballs.

2. you gotta create optimized landing pages for different audiences. suddenly you're learning about your market segments real quick.

3. you get hard data on what actually works, not just what you think works. your gut feeling means jack when the numbers are staring you in the face.

if you find profitable channels, why the hell wouldn't you pour gas on that fire?

but it's not just about the wins. even the Ls are valuable. bad ads tell you what doesn't work before you waste months or years scaling the wrong thing.

don't get me wrong, i'm not saying 'ads or die'. 

but i am saying don't close doors just to feel superior.

as founders we need to use every tool in the box. test, learn, iterate.

that gives us the most amount leverage. helps us in case we don't want to raise vc, helps us when we want to sell, helps us sleep at night.

your 'organic only' policy might be costing you more than your first ad campaign ever would.

note: i recommend boringads.com if youre looking for an agency that will build profitable ad campaigns. they use ai/their own software to help optimized. they are waitlist only at the moment. loved it so much, i invested.

forget virtual reality, the next big thing is actual reality

--

if startup ideas are your thing, i put together a database of 30+ startup ideas below (some software, some irl ones, some could be pretty profitable) 

grab it while you can https://lnkd.in/dGt8Cch4

CEO of Late Checkout, a holding company for businesses powered by community

Clearest path to $10M liquid:

1. Pick your niche. "AI for solopreneurs" not "business tips" riches are in the niches. own your lane.

2. Hit 250,000 impressions/month. one viral hit can do it. but consistency wins. post daily. engage. be THE person in your space.

3. Convert 0.5% to leads = 1250 organic leads/month irresistible lead magnet. so good they'd be dumb not to grab it. calculator, ebook, whatever. just make it valuable.

4. Monetize leads immediately. each lead nets you $1 from affiliate sales or ads 1250 leads = $1250 to reinvest

5. Buy more leads. spend that $1250 on leads at $2 each 1250 / 2 = 625 additional leads

6. Total monthly leads: 1875 1250 organic + 625 purchased you're now a lead generation machine

7. Nurture like crazy. weekly newsletter or free community content. give so much value they feel guilty not paying you.

8. Ask the community what you can build for them. Prioritize painpoints

9. Launch $30/month offer. aim for $300+ per customer annually. make it feel like a no-brainer. their "tip" to you for all the free value.

10. Convert 3% of total leads = 56 new customers/month 1875 * 0.03 = 56 trust = cash. if you've done 1-7 right, this is easy.

11. Year 1: 672 customers = $201,600 ARR 56 * 12 = 672 672 * $300 = $201,600 feels small? it's just the beginning.

12. Reinvest profits in lead buying. you're now profitable on each lead. buy more. turn your funnel into a vending machine.

13. Year 3: 5000 customers = $1.5M ARR compound growth is a beautiful thing.

14. Premium power upsell 20% to $100/month. another 5% to $500/month. New ARR: $2.7M (4000 x $300) + (1000 x $1200) + (250 x $6000) = $2.7M

15. 5 year growth plan 50% annual growth. Year 5 ARR: $9.11M

16. Exit for 3-5x ARR = $27M - $45M or keep it and enjoy your cash cow.

17. Cool tropical island you just bought my friend 

18. tell your grandchildren how you turned a tweet into generational wealth

Not saying this is easy but this is the path. No VC required. Optional.

Build audience, build community, sell product.

for some free guides for founders and startup ideas check out gregisenberg.com

Sabrina Ramonov 🍄

job titles are having an identity crisis 				                       

PMs are becoming engineers, engineers are becoming PMs

marketers are coding landing pages, devs are writing viral threads

designers are shipping full-stack apps, backend engineers are obsessing over UI

content creators are raising Series A, VCs are starting YouTube channels

data scientists are running A/B tests, growth hackers are building ML models

support reps are defining product roadmaps, founders are handling customer tickets

sales teams are building community, community managers are closing enterprise deals

CFOs are becoming startup CEOs, serial founders are becoming micro PE firms

solopreneurs are building holdcos, corporate suits are becoming indie hackers

Replit/Cursor AI builders are outpacing CS grads, drop out indiehackers are outearning PhDs

AI prompt engineers are replacing whole departments, traditional roles are learning to prompt

open-source maintainers are becoming influencers, TikTokers are contributing to GitHub

the line between building and distribution is gone

the most valuable person in 2025:

the one who can wear every hat and ship while everyone else is having meetings

careers are now skill Tetris fit odd-shaped abilities together clear rows or get stacked out

build, market, sell, repeat

i share everything i learn (ideas, frameworks etc) at gregisenberg.com (subscribe for free)

we're living in the startup golden age, and most are sleeping through it

a reel could beat a superbowl ad, a replit prompt could build prototype, a tweet could land 1000 customers etc etc

most startups dont even need to raise vc anymore

my friend, these are the good old days

--

i recommend downloading my free guide to come up with endless startup ideas with ai and reddit https://lnkd.in/e7YCy3YP

the $100m agency playbook for 2025

1. start with consulting (you're the product)
2. use AI to 10x productivity (work smarter, not harder)
3. build custom AI agents (digital clones of your expertise)
4. agents become the service (scalable you)
5. human touch becomes the luxury add-on

congrats, you've created an infinitely scalable business

old model: time for money
new model: agents for money

key to winning:

- best AI training data (your expertise)
- slickest UX for your robo-workforce
- strong community of people who love your brand 
- knowing when humans need to step in

2020: "we're a remote-first agency" 
2025: "our CEO is an API"

accenture has a $212B market cap and 733k employees. 

and “their margin is my opportunity”

You can take a slice of that $212b and build a mini version of them with like 10 employees is 1m agents

People always made fun of agencies. Especially in silicon valley.
“You have to scale with people. What kind of business is that lol”. Not anymore.
Scale with AI agents. Tech isn’t 100% ready yet, but get ready.

Might be one of the best businesses to be in. Happy building.

--

find winning startup ideas using reddit and AI here (for free) https://lnkd.in/e7YCy3YP

The next wave of successful founders won't be engineers. They'll be attention architects. Building is commoditized. Capturing mindshare is the new moat.

This inverts how so many of us went about building  startups

The new gatekeepers are algorithms, not VCs.

—

find winning startup ideas using reddit and AI here (for free) https://lnkd.in/e7YCy3YP

hear me out - we need to build a new school for marketing

"learn to market" is the new "learn to code"

make it free, global, all ages, IRL events in select cities

when tools came out like codeacademy etc around 2011 for developers it changed the game

1. Indian kids access Silicon Valley dreams
2. dropouts build startups
3. career switchers land FAANG
4. houses bought, parents retired, lives changed

it's amazing. "learn to code" was the ultimate hack

but that playbook's dead, let's admit it

we need the same for marketing, growth, taste (damn, i said it).

marketing is the new coding

come out of this knowing your way around ahrefs to google trends to meme pages.

Codecademy meets Y Combinator
TikTok scroller to growth genius

not just education
economic empowerment at scale

this isn't just education it's economic empowerment at scale

let's democratize the ability to sell, not just the ability to build

the next great equalized isn't learning to code, it's learning to market

lives will change, I can't stop thinking about it

-- 

in the meantime, i share free tutorials and startup ideas on my pod

youtube: https://lnkd.in/ebpMJaHS 
apple: https://lnkd.in/eH9hfysC
spotify: https://lnkd.in/eqtNV4Kv

and i sent out free startup ideas and guides if you subscribe at gregisenberg.com

The most unstoppable person on the planet right now is someone who knows how to create video the algorithms love and someone who knows the new LLM tools like claude/v0/cursor etc better than 99.9% of people

millions of views daily. 

new product experiments weekly.

game over.

lots of noise about amazon, starbucks etc dragging employees back to offices 

but i have to be honest, the future of startups is in your pajamas, chatting with ai agents all day

here's a day in the life of your tech job in 2027 

9am: ai-sarah dms you: 

"morning boss! 15 tweets scheduled. engagement's up 40% from last week." you nod, impressed. 

sarah knows your audience better than you do at this point

ai-mike jumps in: 

"got our data rundown. analyzed 50 million user interactions since yesterday." 

you dm mike:

"bro, step it up. sarah's crushing it. where's our viral moment?"

ai mike, sounding almost hurt: 

"check your inbox."

ai mike prepped 20 short-form video concepts. 85% chance one goes viral if posted at 10am tomorrow."

you skim them. hate to admit it, but mike's probably right.

you to the "team": 

"nice work sarah. mike, solid concepts. let's workshop the top 3. i'll decide by 4pm."

as you wrap up, you realize you're playing office politics with code. welcome to 2027.

3pm: engineering standup 

ai-alex kicks off: "sup team. 

50 bugs squashed, 30 prs merged, 5 new features shipped." 

you: "any hiccups?" 

alex: "nothing major. had to rollback one deploy, but fixed and re-shipped in 3 minutes." 

ai-jamie chimes in: 

"i've optimized our database queries. we're now 30% faster." you nod, impressed: 

"nice work. what's next?" 

alex: "i've drafted architecture for that new feature. need your sign-off." you review it. it's solid, but you tweak a few things. can't let the ais have all the fun. 

as you wrap up, you realize you're now the coach of an ai dev team. 

your first coding job self is laughing hysterically. coding yourself is so 2023.

5PM: log off. 

realize you haven't spoken all day. your plants are staging an intervention (i dont blame them)

this isn't some far-off future. it's right around the corner.
freelancers will ping AI collaborators more than clients. 

solopreneurs will scale with digital teams, not human ones.

sure, big tech wants butts in seats but little companies, and new startups where you are in complete survival mode, yeah, you're holding onto your ai agents with your dear life

future of work isn't about your zip code it's about how many AI minions you can juggle and how optimized they are

im not saying this future is better. i feel like missing that human element is going to leave a gap and is less fun

but the reality is pandoras box has been opened and if you believe that all these tech companies are going back to work, you've been mistaken 

get ready for a world where your best colleague is a bunch of 1s and 0s and your office is wherever your laptop and unwashed coffee mug are

welcome to tech, 2027 edition. 

hope you like talking to robots.

need startup ideas? heres how i use ai to find 'em https://lnkd.in/e7YCy3YP

Niche internet communities are in high demand. And it's not stopping. 

But the best part isn't the traffic from Reddit. It's the ideas and trends.

My entire business is plan is listen to what people say on Reddit, and build internet products for them.

It keeps working.

It’s never been easier to find ideas to build and build ideas quickly

There are tons of bad startup ideas.

But ideas from subreddits are validated.

People are literally telling you what they want.

I’ve learned 3 main things about finding business ideas within reddit

1) There are more business ideas you have time for
2) Choosing the right subreddit to focus on is paramount (too big is bad, too small is bad, growing is good)
3) Prioritize by their willingness to pay/impact

Seriously bad advice:

It takes just as much work to start a big company, than it does a small one, so might as well go big or go home

This isn't true.

Sending people to Venus, way more difficult than unbundling a subreddit.

The 2024/2025 Reddit playbook:

1) Use AI/software to scrape painpoints
2) use AI + offshore/nearshore talent to build cheaply
3) Obsess over 1 marketing funnel 
4) Use SEO/Ads/content to drive traffic to funnel 
5) Target 60% gross margins
6) Print

19 weird tricks to find your $1M startup idea (saas, software, agencies etc)

1. Analyze ChatGPT's "I can't do that" responses. AI limitations = opportunities for human-AI hybrid tools

2. Analyze popular Replit templates and forks. What devs are building fast = opportunities for advanced tools

3. Study v0's most requested components. UI patterns in demand = ideas for design tools or libraries

4. Study Fiverr's fastest-growing gig categories. Emerging skills = new SaaS tool ideas

5. Monitor Reddit's fastest-growing niche communities. New subcultures = untapped markets

6. Analyze Shopify app store's top-rated plugins. Popular features = standalone SaaS potential

7. Study big tech companies' API deprecation notices. Discontinued services = gaps to fill

8. Monitor trending GitHub repos in non-tech categories. Techies solving non-tech problems = market validation

9. Analyze YouTube tutorials with highest engagement. Complex processes = automation opportunities

10. Study VC firms' job boards for portfolio companies. Shared needs across startups = B2B SaaS ideas

11. Monitor changes in App Store & Play Store policies. New restrictions = opportunities for alternative platforms

12. Analyze Substack's top-earning newsletters. Paid content niches = ideas for premium tools and software

13. Study browser extension stores' trending section. Simple tools with traction = ideas for full-fledged products

14. Monitor Vercel's analytics for fastest-growing deployment types. Emerging web tech = opportunities for dev tools and services

15. Study popular LangChain templates and use cases. Common AI workflows = ideas for no-code AI builders

16. Analyze Hacker News' "Show HN" posts. Developer pain points = ideas for dev tools

17. Study Kickstarter projects that hit 1000%+ funding. Overserved niches = ready markets for expansion

18. Analyze trending topics on tech-focused Discord servers. Developer chatter = early signs of next big thing

19. Monitor Stack Overflow's most upvoted unanswered questions. Unsolved dev problems = ideas for breakthrough tools

Cool, you’re now an idea machine. And not just any ideas. Validated ones. 

That’s beautiful.

i put together a guide on how i use AI and Reddit to come up with endless startup ideas --> get it for free while you can https://lnkd.in/e7YCy3YP

reflections on my 20s - a 3 page essay on making friendships, moving to sf/la/nyc etc

for more stories like this go to gregisenberg.com and smash subscribe.

YouTube JUST announced this new thing called Hype and it's lowkey genius

imagine you're scrolling and see a wonderful video from some small creator. you wanna do more than just like or share. enter Hype. 

okay, here's how it works 

you get 3 "Hypes" a week to boost videos you dig. it's like a supercharged upvote. 

more Hypes = higher on a special leaderboard.

but here's the thing

it only works for creators under 500K subs and vids less than a week old. plus there's a "small creator bonus" so the little guys can compete.

why's this smart

1. turns passive viewers into active supporters (people want to support the up and comers!)
2. gives smaller creators a shot at blowing up
3. YouTube gets more engagement without messing with the algorithm
4. promotes niches so everything isn't watching the same thing (increase watch time)

"In just the first four weeks of our beta tests in Turkey, Taiwan, and Brazil, users hyped over 5 million times across more than 50,000 unique channels" - YT Team

it's not about killing the big creators. it's about giving the underdogs a chance to be seen.

it currently being tested 

let's be real, social's been feeling stale. same big accounts, same content, rinse and repeat.

you either dont get seen or you go ballistic. 

Hype. it's like CPR for the internet dream. suddenly, that person making weird videos in their bedroom could be tomorrow's viral sensation.

just like the good ole days.

it's bringing back that wild west vibe of early YouTube. when any random video could blow up overnight.

i totally can see a hype-type feature for platforms like X/Twitter too. i hope it takes off.

it's about keeping the internet weird, creative, and unpredictable.

so yeah, Hype might just save us from an endless feed of polished corporate content and put the "social" back in social media. maybe its the domino we need to get other social platforms to do the same.

let's see who/what the internet decides to make famous next.

time to make the internet weird again.

I'm playing with the weirdest new viral social app. It's called SocialAI.

Imagine X/Twitter, but you have millions of followers.  Except the catch is they are all AI. You have 0 human followers.

Here's how it works:

You post a status update. Could be anything.

"I'm thinking of quitting my job to start a llama farm."

Instantly, you get thousands of replies. All AI-generated.

Some offer encouragement:

"Follow your dreams! Llamas are the future of sustainable agriculture."

Others play devil's advocate:

"Have you considered the economic viability of llama farming in your region?"

It's like having a personal board of advisors, therapists, and cheerleaders. All in your pocket.

The creator calls it a "tool for therapy, journaling, or simply feeling heard."

But here's where it gets interesting:

It's addictive. Really addictive.

I found myself posting more and more. Craving that instant hit of attention and feedback.

It felt good. Too good.

I can see how some people might prefer AI followers to real people. They always said the right thing. They were always there. 

And this is the harsh truth about social:

Most people don't get heard on social. They scream into a void and no one pays attention.

Is this the future of social media? A personalized echo chamber where we're all the main character in our own show?

Or is it a dark mirror, reflecting our deepest insecurities and need for validation? 

I'm not sure. But I see the appeal.

What do you think? Would you try it? Or does the idea of an AI-powered social network make you want to throw your phone in the ocean?

I'm genuinely curious. 

Do you hate it or love it.

Taplio

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