The Story
Greg Eisenberg runs Late Checkout, a holding company doing eight figures in revenue with mid-seven figures in profit. He's been part of companies that raised billions of dollars, but makes more money and works less as CEO of his own holding company.
His origin story includes a life-changing moment at 17 - a school shooting where 19 people were shot. That experience made him realize life is short and he wanted to do big things.
- •"I realized as a 17-year-old that life is short and I wanted to do big things."
Greg later sold his company Islands (Discord for college students) to WeWork and became head of product strategy. When WeWork went from $47 billion valuation to near-bankruptcy, he vowed his next venture would be profitable from day one.
The Six Businesses
Late Checkout owns six companies:
- •LCA - Innovation agency working with Nike, Dropbox, Shopify, TikTok
- •YouProbablyNeedARobot.com - One of the biggest AI communities online
- •DesignScientist.com - Design agency
- •Boring Holdings (another holding company):
- •BoringMarketing.com - AI-assisted SEO business
- •BoringAds.com - AI-assisted ads agency
- •Multipreneur.co - Community for multipreneurs
The ACP Funnel
Greg's secret sauce for the last 15 years:
A = Audience
Build a social media audience (Twitter, Instagram, TikTok). Greg built a Twitter account of 10,000+ followers.
- •"10,000 people - anyone can get to 10,000 followers."
C = Community
Convert audience members to a place you own (emails, SMS, community). Greg hosted "orange wine disco parties" in Williamsburg basements and met his first clients there.
P = Product
Create the product they want most. After building trust at parties, he told people about LCA and they said "come into my office first thing Monday."
- •"The ACP funnel is the secret sauce that I've used for the last 15 years that I'm only now sharing with the world."
The $1.5M/Year Client Model
Instead of charging $1,500/month like most agencies:
- •"We charge on average $1.5 million a year. Why? Because if we come up with a whole new vision for where to take your company, often times those products generate 9 to 10 figures of revenue. $1.5 million sounds like a pretty good trade."
First year: $1.5M revenue with one big client and one half client
Second year: $5M+ revenue with a few clients at $1M each
Why Multipreneurship
Instead of one company doing $100K/month, have multiple companies doing $25K/month each:
- •Built-in insurance if one struggles
- •Protection from platform changes (Google, Instagram)
- •Compounding effects are "next level"
- •Cheaper and faster than ever to build with AI
- •"Not only is it cheaper than ever to build, faster than ever to build with AI, the compounding effects are super real."
Building Multiple Businesses
The Nice Break Failure
Started with product first - wrong approach. Closed it down.
Design Scientist Success
- •Started Twitter account around design inspiration
- •Got to a few thousand followers in weeks
- •Saw opportunity
- •Whipped up landing page, brand, and team in 72 hours
- •First year: 7 figures revenue, $450K profit
Boring Marketer Success
- •Started Twitter account about "boring" marketing (ads, SEO)
- •Built community
- •Created AI-assisted keyword research and SEO content tool
- •First year: $350K profit
- •Second year projection: $2-3M profit
Hiring Strategy
Two methods:
- •From communities: Reach out to most active "nerds in residence" - experts who care
- •Cold DMs: Find interesting people online, get their email, DM them
- •"The best people to hire actually work a job."
Idea Finding Tools
- •RedditList.com - Shows how fast subreddits are growing
- •GummySearch.com - Takes a subreddit and shows biggest problems
- •"It's your job as the entrepreneur, as the multipreneur, to solve them."
Other Tools
- •Framer (landing pages)
- •ConvertKit (email with automations)
- •VidIQ (YouTube competitive analysis + top questions in comments)
- •Slack (team communication)
- •Notion (entire team runs on it)
- •Figma (designs)
- •Loom (quick video updates)
Day in the Life
- •Wake up 6am
- •French press coffee
- •Watch sun come up outside
- •Plan 2-3 things that would make the day successful
- •45-minute afternoon workout
- •After work: activities without phone to reset
Key Advice
- •"I made the mistake of listening to the top entrepreneurs of my day who said go build a venture-backed company and scale it and be Mark Zuckerberg. I was living someone else's life."
Greg spent 12-13 years working 7am to 2am, 7 days a week.
- •"Everyone deep down knows what's for them and life is about getting to that truth. Find your truth, don't listen to what anyone says, and go after it."
Resources
- •Late Checkout: https://latecheckout.co/
- •Follow Greg: https://twitter.com/gregisenberg