From 5by to WeWork to Late Checkout is the line that best explains Greg Isenberg’s wealth curve and how each chapter funded the next.
I’m laying out a simple timeline, the deal moments that mattered, and the operating choices that turned cash into compounding.
I’ll cite first-party sources and credible trackers, then translate each event into a “what this did to net worth” takeaway you can copy.

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1) 2012–2013: 5by launches and sells in 11 months

5by, a mobile video discovery app, is founded and quickly gains heat.
StumbleUpon acquires 5by in September 2013 for an undisclosed sum. TechCrunch
Coverage the following year underscores 5by’s role in StumbleUpon’s mobile strategy. Forbes
Net-worth effect: First real liquidity event.
Founder lesson: Tiny team + clear wedge can exit fast in momentum markets.

2) What the 5by exit unlocked

The acquisition gave Greg both capital and credibility.
That combo bought time to hunt the next product and opened doors with future acquirers and advisors.
Net-worth effect: Cash cushion + brand → higher risk tolerance and better deal flow.

3) 2016: Islands—the “community messaging for campuses” wedge

Islands targets college communities with a focused messaging experience.
The thesis rhymes with “unbundling” long before it’s a mainstream operator talking point.
Net-worth effect: Equity in a second swing with a clearer buyer universe.

4) 2017–2018: Fundraising and traction signals

Islands raises seed capital and ships into campus networks.
The product sits in a category acquirers understand: community and IRL coordination.
Net-worth effect: Paper value rises but is illiquid.
Risk: Category shifts and platform dependencies can rewrite outcomes overnight.

5) June 13, 2019: WeWork acquires Islands

PitchBook flags the deal and investor set.
Tracxn lists the acquisition date. PitchBookTracxn
Greg’s own bio confirms the sale and his post-deal role. Greg Isenberg
Net-worth effect: Second liquidity event + stock/comp package.
Founder lesson: Build where strategic buyers need distribution and community DNA.

6) 2019–2020: Head of Product Strategy at WeWork

Greg serves briefly as Head of Product Strategy after the Islands acquisition.
Public profiles and the Late Checkout Substack “About” page corroborate the role. THE ORGlatecheckout.substack.com
Net-worth effect: Salary + equity + network at a hyper-visible brand.
Skill gain: Enterprise product exposure and BD muscles that later help land premium agency work.

7) The WeWork reset and the operator takeaways

The WeWork saga hardens an operator’s instincts around burn, focus, and optionality.
Seeing a rocket ship wobble makes “cash-flow first” more than a slogan.
Net-worth effect: Sets the stage for a holdco built on durable margins.

8) 2020: Late Checkout is born

Late Checkout positions as an agency, studio, and fund building community-based products.
The official site is explicit about the three-arm model. latecheckout.studio
Net-worth effect: A controllable profit engine that can fund equity bets.
Founder lesson: Services → IP → ownership.

9) The agency engine—how money actually hits the account

Late Checkout sells product strategy, design, and now AI-native execution on projects and retainers.
Founder credibility and media reduce CAC and raise pricing power.
Net-worth effect: EBITDA today that can be capitalized at 4–7× in private markets.
For practical pricing signals and deck craft, see our post: The Ultimate Guide to Pitch Decks.

10) The studio arm—turning services into IP

Client problems become reusable products.
Winners can spin off ARR or exit for step-function gains.
Net-worth effect: Lumpy but asymmetric upside layered on top of services.
If you’re valuing these bets, read: AI Startup Valuations: The Reality Check You Need.

11) The fund arm—fees now, carry later

A small fund adds 2%-ish fees and long-dated carry.
Carry only matters at DPI, not on paper marks.
Net-worth effect: Modest operating income with lottery-ticket upside.
For investor-grade metrics, start here: Investor Metrics that Matter.

12) 2023–2024: Public breadcrumbs on revenue scale

A December 28, 2024 teardown pegs Late Checkout around $833K MRR (≈$10M ARR).
Treat it as a directional clue, not audited GAAP. Starter Story
Net-worth effect: If true and margins hold, owner distributions + private-market value lift the curve.

13) 2024: “Year-in-Review” and the 38% net-worth jump

Greg’s own video covers allocation and performance.
Summaries call out a 38% net-worth increase, with ecosystem businesses like Boring Ads cited among drivers. YouTubesummiz.ai
Net-worth effect: Confirmation that the holdco model is compounding.

14) 2025: AI-native services and ecosystem bets

The content cadence shows a push into AI-assisted marketing, product, and ops.
His channel activity underlines “distribution as leverage” for the agency and products. YouTube
Net-worth effect: Higher margins and faster deal flow when media and delivery reinforce each other.

15) Inflection #1: First exit (5by)

Small team.
Fast timing.
Strategic buyer.
Wealth impact: The first dollar is the hardest.
It funds exploration and raises your ceiling for the next bet. TechCrunch
For more on early-stage deal readiness, see: Raising Capital in 2025.

16) Inflection #2: Second exit + strategic role (Islands → WeWork)

A second sale validates pattern recognition in community products.
The post-deal role compounds network and credibility. PitchBookGreg Isenberg
Wealth impact: Liquidity + career equity that later converts into premium agency demand.

17) Inflection #3: Agency EBITDA at scale

Repeatable delivery + strong brand → 20–30% EBITDA in a senior shop.
Even at mid-single-digit millions of revenue, owner distributions add up.
Wealth impact: Cash today and a private-market multiple tomorrow.
If you’re pitching this machine, review: Series A Funding Checklist 2025.

18) Inflection #4: Studio hits and secondaries

One product hit or a small secondary sale can add more to net worth than a year of services profit.
Wealth impact: Step-function jumps that reset the baseline.
To negotiate outcomes, read: How to Negotiate Your First Term Sheet Like a Pro.

19) Inflection #5: Media and advisory compound pricing power

Advisor roles at Reddit (and previously TikTok) and a heavy YouTube cadence funnel into sales velocity and rate cards. latecheckout.substack.comLinkedInYouTube
Wealth impact: Lower CAC, higher conversion, better clients.

20) Risks and drawdowns to model

Agencies are people-heavy and cyclical.
Studio and fund marks are illiquid until DPI.
Platforms change, which can hit distribution and demand.
Wealth impact: Expect volatility, hold more cash than feels comfortable, and haircut paper gains.

FAQs

Did Greg disclose the dollar value of either exit
No.
Both acquisitions are public, but terms were undisclosed. TechCrunchPitchBook

When exactly did WeWork buy Islands
Tracking sources place the acquisition in mid-2019, with Tracxn listing June 13, 2019. Tracxn

What is Late Checkout exactly
It’s a community + product design firm that operates as an agency, studio, and fund. latecheckout.studio

Is the $833K MRR a confirmed number
No.
It’s a public teardown estimate from December 28, 2024 and should be treated as directional. Starter Story

Did Greg confirm a 38% net-worth increase in 2024
He published a “Year-in-Review” video, and reputable summaries attribute the 38% figure to his recap.
Treat it as self-reported. YouTubesummiz.ai

What did the WeWork role contribute besides salary
Access to enterprise problems, partners, and talent, which later raises agency pricing power. THE ORG

Where can I learn more about his operator thesis
His Substack “About” and personal site frame the Late Checkout approach and advisor roles. latecheckout.substack.comGreg Isenberg

How should I value an agency like Late Checkout
Use EBITDA × private multiple (often 4–7×) and apply a founder-dependence discount.
Don’t use SaaS multiples.
For valuation sanity, see: AI Startup Valuations.

What’s the single most copyable move for founders
Stand up a profitable service, then convert repeat problems into studio IP while you publish weekly to lower CAC.
For outreach and follow-ups, use: 13 Templates for Investor Follow-Ups.

Where is a one-page primer on investor-grade metrics
Start here: Investor Metrics that Matter.

Conclusion

From 5by to WeWork to Late Checkout isn’t just a résumé line.
It’s a repeatable playbook of liquidity → cash-flow engine → equity optionality → media-powered distribution.
If you’re mapping your own net-worth inflection points, model cash first, haircut paper gains, and let distribution compound.
Subscribe to Capitaly.vc Substack (https://capitaly.substack.com/) to raise capital at the speed of AI.

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