Islands → WeWork: What That Acquisition Likely Meant for Greg Isenberg’s Net Worth (Scenario Analysis)

The Islands → WeWork acquisition is real, but the terms were undisclosed. Business Insider
So I built a clean, source-backed scenario model for how it could have impacted Greg Isenberg’s net worth.
I’ll show the facts we know, then three plausible outcomes with transparent assumptions you can tweak.

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What we actually know (facts only)

WeWork acquired Islands Media in 2019. PitchBook
Business Insider’s M&A rollup lists “Islands Media” with deal date April 2019 and a prior private valuation of $8.42M (from PitchBook). Business Insider
Tracxn also records the acquisition, showing Jun 13, 2019 on its timeline and total funding of ~$1.9M. Tracxn
Post-deal, Greg served as Head of Product Strategy at WeWork. latecheckout.substack.comTHE ORG
Months later, WeWork’s attempted IPO imploded and the valuation collapsed, which matters if any founder consideration was equity-heavy. Crunchbase NewsBusiness InsiderForbes

Why exact proceeds are unknowable

Terms weren’t filed.
Cash vs. stock vs. earnout wasn’t disclosed.
We can’t see vesting schedules or any secondary sales.
So the honest move is scenario analysis anchored to public breadcrumbs.

Modeling inputs I use (and why)

Last private marker: $8.42M valuation before acquisition (directional anchor, not price). Business Insider
Founder ownership: 35–60% range is typical at this stage given outside funding (~$1.9M) and a small team. Tracxn
Consideration mix: common in 2019 for WeWork deals to include cash + stock and retention. Business Insider
WeWork equity risk: post-2019 drawdown means stock could be marked down massively by 2023–2024. Forbes
Tax: I apply a ~37% effective rate to keep math conservative.
Salary: public profiles show roughly one year in-role, so I include a $300k–$500k retention comp line as a placeholder. THE ORG

Three plausible scenarios (all numbers are illustrative, math shown)

Low case → “Acqui-hire weighted to stock (which later went to ~zero)”
Assumptions: $6M headline price, 45% founder ownership, 20% cash / 80% stock, stock ends up worthless by 2025, $300k retention, 37% tax.
Result to founder (after tax + salary): ~$0.64M.
Intuition: minimal cash, stock wiped out by WeWork’s collapse. Forbes

Base case → “Mid-eight figure price with balanced mix, tiny stock recovery”
Assumptions: $12M price, 45% founder ownership, 50% cash / 50% stock, only 10% of stock value ultimately realized (e.g., partial sale or settlement), $400k retention, 37% tax.
Result to founder (after tax + salary): ~$2.27M.

High case → “Strategic buy, mostly cash, some stock value retained”
Assumptions: $25M price, 50% founder ownership, 70% cash / 30% stock, 25% of stock value realized, $500k retention, 37% tax.
Result to founder (after tax + salary): ~$6.60M.

Why the spread?
Because two levers dominate founder outcomes here: cash % at close and how much WeWork stock was actually monetized before the crash. Business InsiderForbes

What the Business Insider/PitchBook datapoint implies

BI shows Islands’ last private valuation at $8.42M and an undisclosed purchase price in April 2019.
If the price roughly tracked that private mark (plus or minus), the Base scenario looks directionally reasonable. Business Insider
If WeWork paid a strategic premium, the High case becomes plausible.
If it was a pure acqui-hire, the Low case is closer to reality.

How this likely changed Greg’s net-worth curve

Even at the Low/Base outcomes, a seven-figure cash outcome plus a year of comp is enough to seed the next hold-co move.
That lines up with the Late Checkout chapter starting soon after, where cash-flow (agency) funds upside (studio/fund). latecheckout.substack.com
If you’re modeling similar “services→studio→fund” stacks, start by valuing the agency on EBITDA × 4–7× and haircutting illiquid marks.
For a sanity check on private multiples, read: AI Startup Valuations: The Reality Check You Need.

Adjust the model for your own assumptions

Increase founder ownership if you believe dilution was lighter.
Increase the headline price if you have reason to believe it was strategic.
Set stock realization to near zero if you’re certain no liquidity happened before the crash.
Re-run the math and see how fast outcomes swing.

Sources to keep this honest

WeWork acquired Islands in 2019 (PitchBook brief). PitchBook
BI’s M&A list shows Islands Media with Apr 2019 date and prior $8.42M private value. Business Insider
Tracxn logs the acquisition and Islands’ ~$1.9M in funding with a Jun 13, 2019 acquisition date. Tracxn
Greg’s Head of Product Strategy role at WeWork is listed on his Substack About and org profiles. latecheckout.substack.comTHE ORG
WeWork’s IPO implosion and valuation collapse provide the macro context for equity-heavy deals. Crunchbase NewsBusiness InsiderForbes

Related reads on Capitaly.vc

For valuation mechanics, see: Investor Metrics that Matter: A Founder’s 2025 Guide.
For negotiation leverage, read: How to Negotiate Your First Term Sheet Like a Pro.
For the broader profile, see: Greg Isenberg Net Worth: All You Must Know About Him.

Bottom line

The Islands → WeWork deal likely added low- to mid-seven figures of realized cash to Greg Isenberg’s war chest, with WeWork equity contributing little to net worth unless he sold early. Forbes
That was enough to bankroll Late Checkout and the agency→studio→fund flywheel.
Subscribe to Capitaly.vc Substack (https://capitaly.substack.com/) to raise capital at the speed of AI.

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