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).

I bought 50% of a business 1.5 years ago, and it’ll do $2-3M of free cash-flow this year.  

I got paid back my original investment in 6 months.

It got me thinking...

This is the golden era to buy a venture-backed business. 

Startups are going OUT OF BUSINESS left, right and center.

They want to raise more VC, but they can’t. Raised too much in the ZIRP era and tons of VCs still on sidelines.

They want to sell, but they can’t. Anti-trust and high interest rates are making big acquirers more cautious.

They want to go IPO, but they can’t. There are 85% less IPOs in 2023 than 2021. The bar to IPO is sky high.

So what’s going to happen?

The amount of startups going out of business is skyrocketing.

They either shut down.

Or they sell for pennies on the dollar.

Maybe that’s where you come in.

You see, a lot of these businesses are great businesses.

Some of these products are

But they’ve just raised too much capital.

Many founders are just going to want to move on.

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

This is how they’ll do it:

Step 1: Acquire businesses at an attractive price
Step 2: Create internet distribution to scale customer base
Step 3: Build AI-assisted software to increase margins
Step 4: Recycle cash-flow to buy more businesses

I did this 1.5 years ago.

1) Bought 50% of http://boringmarketing.com, best SEO implementors on the planet
2) Scaled Boring Marketer audience and community to 40,000+
3) Built a suite of AI tools that makes http://boringmarketing.com unbeatable at SEO and helps get our margins to 50% 
4) Using cash-flow to buy a new businesses (more on those soon)

We were able to partner with the best team on the planet because to create a high-margin, asset light business.

Even VCs I know want to talk to me about cash-flow businesses.

Some are even getting involved on the size of their day-jobs.

All of sudden cash flow is cool.

Those "boring" internet businesses powered by audiences, community, SEO (cc @boringmarketer
) are top of mind.

And unlike VC-backed business (most fail, few win massively), there are tons of  "middle class" cash-flowing  internet businesses. Especially tons of AI wrapper ones.

I see http://boringmarketing.com doing AI-assisted SEO for LOT of these profitable Internet businesses. They are EVERYWHERE.

More and more folks will either snap these businesses up or start them.

So, as the VC market starts to crack.

It’s the golden era for buying. A way more surefire path towards wealth creation.

I figured I'd share how I'm thinking about it in case it's valuable to someone.

If it's valuable, share and let me know.

Buying cash-flow companies is the NEW building venture-backed companies.

Meet Marques "MKBHD" Brownlee. 30 years old, has 18.3M subscribers, 4.2B views and makes $3M+/year.

But you haven’t met him at 10 years old giddy over his 79th subscriber.

This video is his 100th video. A must watch for anyone that puts creative work out on the internet.

It reminded me that “perfection kills progress”.

At age 10, MKBHD wasn’t the best tech reviewer on the internet. But that didn’t stop him.

In the first 6 months of putting out videos, Marques had already posted 200+ videos.

The guy was just unapologetically hitting publish on videos.

And did you watch the intro to this video? 

I mean, that intro got me fired up, but it wasn't exactly a Scorsese film. 

Many of us get  lost in the “comparison trap”.

You don’t start something because you don’t think you’re good enough.

The reality is you aren’t good enough until you start something.

Marques didn’t wait.

He published his work.

From the video: “I hope I get more subscribers if I upload great videos everyday”

It turns out he did. 18M+ of them.

MKBHD shipped 100 videos to get 74 subs.

MrBeast shipped 100 videos to get 760 subs. 

PewDiePie shipped 100 videos to get 2500 subs. 

You get the idea.

Hit publish first, get good later.

You should sign up to gregisenberg.com to hear more stories like this. You'll get a weekly email with free startup ideas, frameworks on how to win on the internet. Subscribing only takes 2 seconds and is free at gregisenberg.com.

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

What are some best practices for publishing content?

What no-one tells you about starting a startup (but I wish they did):

- You most likely won't make life changing money but will probably make "car changing" money or "house changing" money
- Your mental health is always at risk
- You are always drinking your own kool-aid
- You don't need to create the next Facebook
- You'll learn every time you fail ("failing forward")
- You are constantly are getting rejected
- You'll realize distribution is oxygen
- The novelty of being a founder will wear off
- Cash-flow is like an "exit" every year
- If you truly enjoy working with your team, you've won the lottery
- It's a beautiful ride

We created a 5 day email course to create businesses without investors and with internet audiences: 
https://lnkd.in/eYnzEi9B

welcome to my $7331 home office setup in miami: 

1) apple studio display - my fav purchase of 2023 9.2/10 ($2000)
2) branch furniture desk/chair - super clean desk, nice back support 8.5/10 ($800)
3) logitech mx master 3s mouse - sometimes looses connection to bluetooth 7/10 ($83)
4) daft punk signed record by giorgio moroder - he wished me hbd, this fires me up when i look at it, 10/10 (priceless)

5) shure mv7 microphone - pretty sure joe rogan uses these shures, so you can sound as good as the top podcasters in the world. loses points because the shure software kinda sucks 8.5/10  ($249)

6) collectible bus - i have a replica of the public bus i took as a kid to go to school, reminds me of where i came from 9.5/10 ($30)

7) 1970s Burl Laminate and Chrome Bar Cabinet/bookshelf, i like the look. 9/10  ($422)

8) google home max - these are just allright (they discontinued them). i've been thinking of getting more into the hi-fi speaker game in my office. open to recommendations 6.8/10  ($180)

9) branch smart file cabinet - i like the minimal, sleek look but i need something bigger. 8/10  ($239)

10) epiphone zakk wylde les paul custom guitar - had this since 2006, reminds me that i shouldn't just stare at the computer all the time 9/10 ($1000)

11) 14" macbook pro m2 - 13 inch too small, 15 inch too big. i often think about getting an apple mac studio for more power, but the laptop is just so convenient 8.7/10  ($2000)

12) neewer 2 packs advanced 2.4G 660 LED Video lights - i love these for recording pods or when i have a big meeting coming up, price was around $200. i also bought the neewer 12.2"x11.4" foldable softbox diffuser on top of it for  8.5/10 ($40)

13) candles - it's a vibe to light candles in your office sometimes. avoid scented candles and dont burn them all day because youre breathing it in. as with most things, the poison is in the dosage  sometimes its fun to just write about your life. ($50)

i definitely missed a bunch of stuff in here, but that's the gist of it. you can zoom into the pics and see what you find.

i've noticed the more ive made my office a sanctuary, the better the work has come from it. i used to be one of those work from starbucks type people. not anymore. i see the value in a space that you love.

i'd love to see what your workstation looks like. pics appreciated. comment below.

hope you enjoyed reading this as much as i enjoyed writing this. this was fun to write.   

not everything on business/startup twitter needs to be so serious, clickbaity or controversial. 

it could just be writing about your life and seeing who's interested.

reminds me of the old internet.

if you enjoyed this, subscribe for free to my newsletter gregisenberg.com. You’ll get free startup ideas and frameworks to help you win on the internet

This is a kinda uncomfortable ask but I'll do it anyway.

If this post gets lots of comments, I'll know to keep creating content for you. 

Have you ever liked one of my LinkedIn posts? 

I write about:

1. Internet communities
2. Cash-flowing internet businesses
3. Holding companies (aka multipreneurship)

I have an ask. If you ever liked one of my posts.

Come join my weekly newsletter at gregisenberg.com (and see my new website)

You'll get free startup ideas, frameworks on how to win on the internet, early access (and discounts) to products I co-create and updates for my weekly podcasts.

I get to know you better, and you get free startup ideas that could get you to finally quit your 9-5 or build the company of your dreams.

Win-win?

See you there.

gregisenberg.com • 1 min read

I speak to lots of founders and their eyes light up when I tell them this:

The greatest chance of making your first $1M or $10M is creating some cash-flowing internet assets and taking dividends.

Keep team small, AI-powered, global, use audiences & communities to power distribution.

Cash-flow is an exit every year. This is something I try to never forget.

You don't need to "pray for an exit" and hope Google buys you for $500M.

And you don't need permission from VCs for a secondary transaction.

Basically, you wire yourself some money and renovate your house.

It's beautiful.

You don't have the safety net of a bank account of $3M from VCs.

I will say, I miss that.

But the mentality away from "burning cash" to "growing cash" is what will make you wealthy.

And once your eyes open up to a dividend model, you'll realize it's a healthier way of doing business for the majority of businesses.

It's an organic way of doing business. Healthier for customers to your team. 

I love it.

My team put together a free 5 day email course on building a company without investors using the "ACP funnel" around building internet audiences/communities.

If that's your thing, you can grab it below:

https://lnkd.in/eYnzEi9B

Why do we call $1B startups unicorns? I've owned equity in companies that have raised billions in VC and the stock ended up worth $0.

The amount of venture capital you raised used to be a badge of honor.

You’d hear about how much a company raised and you were ready to give them a giant pat on the back. 

Nowadays, when I hear someone has raised hundreds of millions of dollars, I cringe. 

Employees probably won't make a $1. That's the harsh truth.

When founders say they've raised a small number with a great business, I’m impressed. 

When founders say they've raised nothing with a great business, I'm even more impressed.

No dilution, no investor updates, no external pressure.

People call companies that have hit the magical $1B valuation mark "unicorns" because of how dreamy it is to hit that milestone.

I don't know about you but it feels like the tides are shifting. Cash flow > valuation.

The real unicorns are the startups that have raised $0, small teams, generate $10M-$1B year of revenue, have brands people love and are cash machines.

Usually, these founders have multiple products, multiple companies, multiple income streams.

Sounds pretty awesome to me.

If it does to you too, here's some free resources for you:

1. The future of building startups: https://lnkd.in/ea9_ZQEU

2. Free 5 day course on the ACP funnel (building businesses around internet audiences and community) --> https://lnkd.in/eYnzEi9B

Enjoy.

I woke up to 2 cancelled podcast guests and 100 emails. But then I got this nice little "top voice" popup from LinkedIn. Tough day turned into a beautiful day.

Life's full of wonderful ups and downs. Enjoy the ride.

I’ve helped build internet communities that have generated 75M+ members & followers:

The most often question I get asked is:

How do I build a community from scratch?

1. Why you should care about community:

It's the best way to build a movement

It supercharges word-of-mouth

People want community more now than ever

Products built on top of communities scale fast

Start small. Start tiny.

2. 95% of communities can start as a simple group chat.

A community only needs a shared purpose and a place to thrive. Don’t overthink it.

Weak community leadership kills communities

3. 6 qualities of high-performing community leaders I’ve noticed:

1. Captivating
2. Consistent
3. Loud
4. Obsessed with the mission/people
5. Relentlessly helpful
6. Sincere

4. Invite-only works

95% of communities should begin as waitlists. B2B or B2C. Doesn’t matter.

Exclusivity and scarcity drives demand

Tip: waitlist communities outperform

5. Merch supercharges communities

You’d be surprised what designing incredible merch can do to a community

It gives them a “raison d’etre”

Tip: hire streetwear designers to design your merch

6. Get members where they want to go

The secret to community design: get members they want to go (ie: milestones etc)

The best communities: move members

7. Who we are

I’ve never found a community that thrived that didn’t have a compelling “who we are” story

Key points:

Describe the future utopia

Describe the cause with passion

Amplify the real reason they exist

Tip: tighten your who we are story and terrific things happen

8. Not all founding members are equal

Your first members set the tone. Choose wisely. 

These are the aspirational members, the members people like being around, the members who will spread your message.

9. Community/market fit

Founders obsess about product/market fit. But don’t obsess enough about community/market fit

9. Design rituals

Being in a Zoom call together isn’t community building

The goal:

Create daily/weekly rituals that make people feel alive and grateful to be a part of the community

Takeaways:

1. Human beings can’t help it: we need to belong
2. The long-term win is in building a community
3. Building a community is where art meets science. It's perfectly do-able

I hope this was fruitful for you. If you made it down here, here's a free 5 day course on how to use my ACP funnel to create a business powered by internet audiences and community https://lnkd.in/eYnzEi9B

Grab it while you can.

Lacework ($200M/year in revenue) is getting acquired for ~$200M. It was worth $8.3B 2 years ago.

The VC startup market is cracking.

This is the golden era to be buying distressed VC-assets and turning them into cash-flowing machines.

Go out there and buy some companies. They are cheaper than you think.

It's deal time.

--

My team put together a free 5 day email course on building a company without investors using the "ACP funnel" around building internet audiences/communities.

If that's your thing, you can grab it below:

https://lnkd.in/eYnzEi9B

I don't know why people don't talk about this...

The best job at a company isn't the CEO. It's the co-founder.

- WAY more equity than an advisor
- WAY less cash upfront than an investor
- WAY less responsibility (and stress) than the CEO

I highly recommend being a co-founder.

Tomorrow is the start of Q2 2024. I ask myself these questions at the beginning of every quarter.  

My business and personal life has been better ever since I started doing this little ritual.

Maybe this is helpful to someone. Sharing in case it is.

--

If this seems helpful, grab a free subscription to my newsletter at gregisenberg.com to become a better entrepreneur.

My life got 10x better (relationships, career, wealth etc) when I removed these words from my dictionary:

1. "I don’t disagree". There is nothing more lame than saying “I don't disagree”. You either agree or disagree or don’t know enough to commit. 

2. "Valuation". Just because a VC tells you how much your company is worth doesn't mean much. I worked at WeWork when we worth $47B and now it’s bankrupt. Replace the word valuation with cash-flow.

3. "I’m so jealous". Replace jealousy with inspiration. You see someone who is doing well, that’s inspiring. Even a stranger, clap loudly for them. Go them!

4. "Too small". When i look back at the projects that have turned into something impactful, they’ve all started off “too small”. I guess there is no "too small" of a project. Markets mature, markets grow.

5. "Revenue". Replaced with profit. Revenue never mattered as a measure to how a business is doing, profit always did. Revenue matters to them, profit matters to you.

6. "I'm so busy". Replace this with "I'm focused on what matters most." Being busy obviously doesn't mean you're being productive. 

7. "I'm stressed" - Stress is a choice. Replace this with "I'm taking it one step at a time." Focus on what you can control and let go of the rest. Letting go is freedom.

8. "I'm not lucky". This is small-time thinking. Of course, people are going to be richer than you, better looking than you, more connected to you but it doesn't mean that you can win the game you're playing.

9. "I can't". Replace "I can't" with "How can I?" This shift puts you in a problem solving mindset, so you overcome challenges instead of surrendering to them. You're about to get really creative to figure this out.

10. "It's all been done before". Replace this with "How can I add my unique touch?" Originality comes from personalization, not from an untouched idea.

11. "That's just how it's done". Who cares how it's normally done. The best ideas come from turning it on its head. Replace with "What if there's a better way?"

12. "Keep your cards close to your chest". I used to cling to my ideas like secret treasures, fearing theft more than obscurity. But ideas in isolation wither. Sharing my craziest thoughts led to collaborations that turned pipe dreams into pipelines. 

13. "Scale fast or fail fast". The Silicon Valley mantra. I chased growth like a high, only to realize I was scaling a house of cards. I raised from literally the world’s best VCs only to learn this the hard way. Sustainable scaling is an art form—it's about knowing when to push and when to pause. Sometimes, the fastest way up is to slow down and strengthen your foundation.

If you disagree/agree with me, let me know.

What else do you stop yourself from saying these days?

-- 

If this resonated, you'll enjoy my post on my predictions in the tech industry (and where you can build profitable internet startups:

https://lnkd.in/esvNmFfz 

I went to SF/LA recently. My biggest takeaways:

1. If you stay in SF long enough, you'll probably raise a VC round
2. If you stay in LA long enough, you'll probably be a vlogger

Do things you actually want to do, not what others want you to do.

28 founder rules that they never teach you:

1. Cash-flow is like an "exit" every year

2. Networking events are 99% a waste of time 

3. Your mental health is always at risk

4. You most likely won't make life changing money but will probably make "car changing" money or "house changing" money

5. Remote teams need culture, too

6. Obscurity is the enemy, not competition 

7. Monetize early, avoid premature traction obsession

8. You are always drinking your own kool-aid

9. Earning trust allows charging premium prices

10. You are in the trust business 

11. Own your own media as much as you can 

12. Revenue makes users, users don't make revenue

13. You don't need to create the next Google (and probably shouldn't)

14. You'll learn every time you fail ("failing forward")

15. You are constantly are getting rejected (and that's okay)

16. Intuitive design wins, explain less

17. The novelty of being a founder will wear off

18. If you truly enjoy working with your team, you've won the lottery

19. Avoid feature bloat, cherish minimalism

20. Micro-virality outperforms macro-splashes

21. Cynics recycle fear, visionaries seed possibility gardens

22. Ignore skeptics, trust your creative callings wholeheartedly

23. Avoid burn rate, become profitable 

24. Chase dividends, not valuation

25. Optimal pricing errs towards simplicity

26. Find App Stores that are growing quickly but aren't giants. Build there

27. You'll realize distribution is oxygen

28. It's a beautiful ride

For more frameworks how to win as a founder and free startup ideas, subscribe below:

gregisenberg.com

My biggest flex is I bought a 3500 square foot house in the mountains outside Montreal, on a lake, with 20% down payment and these are the details. And yes, those numbers are Canadian dollars ($1 USD = $1.36 CAD)

I got lucky. I bought in 2020, and found a place that had natural beauty and was inexpensive.

The payback on my professional life has been huge.

- I get my best ideas in nature, disconnected from the hustle & bustle of Miami, NYC and SF.
- I know that if all else fails, I can always retreat to that home. That makes me take more risks in my business. Since I've bought this home, my holdco went from $0 to 8 figures in revenue.

And personally, it's a game changer.

I grow blueberries in the summer, have a cedar sauna I use to unwind, make fires to keep warm and do the simple things in life with friends and family.

Highly recommend.

The hardest part is many people have to wait for another pandemic for an opportunity like this. 

But, I still believe there are pockets of beautiful places in this earth 90 minutes or less from major airports, worth investing in. 

Game changer.

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