Late Checkout Revenue Explained: Modeling Greg Isenberg’s Earnings From Studio, Fund, and Agency

Late Checkout revenue explained is what founders keep asking me for, so here’s a clear, source-backed model you can tweak for your own assumptions.
I’ll break down how the agency, studio, and fund each make money, how those streams interact, and how to estimate Greg Isenberg’s earnings without relying on clickbait.
I’ll also show you what public breadcrumbs exist and how to update the model as new data appears.

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1) What Late Checkout actually is

Late Checkout is a holding company with three arms: an agency (design and product), a studio (builds/acquires products), and a fund (invests in startups).
Greg Isenberg describes himself as CEO of Late Checkout and frames it as “building community-based internet businesses.” Greg Isenberglatecheckout.substack.com
Late Checkout Agency positions as a “design firm for the AI age,” selling strategy, product, and execution to companies. Late Checkout

2) Why modeling matters before you believe any revenue number

Private companies don’t publish audited financials, so you model with the signals you do have.
Signals include team size, hiring velocity, client logos, pricing posture, and the founder’s own year-in-review commentary. YouTubehoneybunny.money

3) Agency revenue: the three lines that likely matter most

Project work, monthly retainers, and accelerators or workshops are the usual stack for product design firms like LCA.
LCA’s site emphasizes founder-speed strategy plus AI-native product work, which typically commands premium pricing. Late Checkout
I assume a project–retainer mix with average effective rates reflecting senior-team delivery and founder involvement.

4) Pricing and utilization assumptions I use

I model effective blended rates rather than list prices.
I assume 60–75% delivery utilization on revenue teams and 10–20% for leadership time on pre-sales and IP.
I assume 10–20% pass-through for tools or contractors baked into COGS to keep gross margin realistic.

5) Gross margin and EBITDA targets for an AI-first design firm

For a senior, founder-led shop, I use 45–60% gross margin after direct delivery costs.
I then target 20–30% EBITDA at scale given strong inbound and productized delivery.
If hiring outpaces sales, I haircut margin before applying any valuation multiple.

6) Public breadcrumbs and third-party estimates (treat with caution)

Third-party scrapers estimate LCA revenue in the mid-single-digit millions, while narrative profiles sometimes cite eight-figure run rates.
I treat these as directional only, not facts, and I build ranges that can absorb error. CompWorththebizhubco.com

7) Studio economics: services → IP → equity

The studio builds or acquires products that can spin off revenue or exit for equity value.
I model studio cash flow as low in the short term with lumpy upside from product wins or small acquisitions.
I attribute value using conservative revenue multiples or last-round prices with a liquidity haircut.

8) Fund economics in one minute

Management fees are typically 1.5–2.5% of committed capital per year, and carry is usually around 20% of fund profits. CartaHolloway
For modeling LCA’s fund, I plug in a modest AUM guess, apply a 2% fee for operating income, and value carry only on realized or very high-confidence marks.
Unrealized marks are vanity until distribution, so I discount them heavily.

9) Advisory and distribution that feed the funnel

Greg lists advisory work with companies like Reddit and previously TikTok, which boosts pipeline and pricing power even when equity is illiquid. Greg Isenberglatecheckout.substack.com
His weekly publishing and YouTube compound the same effect by creating inbound for the agency and studio. Greg Isenberg

10) Parallel operators like Boring Ads and why they matter

Boring Ads shows him as an investing founder-client, which signals cross-pollination between service ecosystems. boringads.com
I model this as incremental cash flow and lead-sharing rather than a primary revenue line unless we see audited P&L.

11) How I turn those pieces into a base-case P&L

I start with agency top line using headcount × utilization × effective rate.
I add studio revenue only if a product is public and charging, or else I carry it at near zero with optionality.
I add fund management fees as operating income and model carry only beyond a threshold of realized returns.

12) Example numbers you can tweak (purely illustrative)

Conservative case: $6M agency revenue at 22% EBITDA, $0.2M fees, $0 studio cash, for ~$1.5M EBITDA before founder comp.
Base case: $8M agency at 25% EBITDA, $0.3M fees, small studio ARR $0.3M, for ~$2.3M EBITDA.
Upside case: $10M agency at 28% EBITDA, $0.4M fees, studio hits $1M ARR, plus a $2–5M realized or secondary event.
I haircut private upside by 30–50% for liquidity risk before calling it “earnings.”

13) Translating operating profit into founder earnings

I assume a founder draw or salary plus distributions.
I keep a cash buffer of 3–6 months expenses in the business and move excess to owner holdco after tax.
I avoid double counting if the founder also books speaking, course, or media income personally.

14) Valuing the agency arm without wishful thinking

I capitalize agency EBITDA at 4–7× depending on concentration, growth, and founder dependence.
I reduce the founder’s stake by realistic employee participation and retention grants.
I do not apply SaaS multiples to services, even if the output is “AI-native.”

15) Valuing the studio and fund without marking your own homework

I value studio bets at cost or last external price with a haircut until revenue is durable or a sale happens.
I value fund carry at zero until DPI or near-certain exits, and I only include management fees as operating income.
I refresh the model semi-annually against new public data.

16) What the exits tell us about capital to fund the machine

Greg sold 5by to StumbleUpon and Islands to WeWork, which plausibly seeded later self-funding. TechCrunchBetaKit
He also served briefly as Head of Product Strategy at WeWork post-acquisition, which supports the operator-advisor narrative. Greg Isenberg

17) Updating the model with first-party signals

Greg’s “Year in Review” videos and write-ups provide allocation, simplification goals, and performance tone.
I use these to nudge margins or growth assumptions, but I do not lift unaudited numbers verbatim. YouTubehoneybunny.money

18) Sensitivity analysis: the four levers that move Late Checkout most

Average project size, utilization, senior mix, and sales cycle speed swing agency EBITDA the most.
Studio outcomes and fund DPI add step-function changes and can dominate any single-year P&L.
A single product exit or secondary can outweigh twelve months of services profit.

19) Common mistakes when modeling an operator-studio-fund stack

Treating managed ad spend as agency revenue is wrong.
Capitalizing content impressions into dollar value without a pipeline model is wrong.
Ignoring founder time allocation between selling and building is wrong.

20) Founder playbook if you want to copy the structure

Ship a cash-flowing specialty service first, then layer a studio for product and a small fund or angel program.
Use media to drop CAC across every line of business and to win higher-margin, “founder-taste” work.
Institutionalize finance early so your model stays honest and fundable.

For more on positioning and metrics that investors actually care about, see our blog posts: Investor Metrics that Matter: A Founder’s 2025 Guide, The Ultimate Guide to Pitch Decks, AI Startup Valuations, and Series A Valuation.    

If you want Greg’s broader story for context, read our profile: Greg Isenberg Net Worth: All You Must Know About Him.

FAQs

How does Late Checkout make money at the agency level
It sells design, product strategy, and AI-native execution on projects and retainers. Late Checkout

What is the studio and how could it dwarf services
The studio builds or acquires products that can throw off ARR or sell, creating lumpy but large upside.
I model it at low near-term cash with optionality until traction is public.

How do fund fees and carry translate into real cash
Fees are paid annually on committed capital and show up as operating income.
Carry only crystallizes when profits are distributed, which can take years. CartaHolloway

Are there any public revenue numbers for Late Checkout
Only third-party estimates and narrative teardowns exist, so I use ranges and caution. CompWorththebizhubco.com

What signals should I watch to refine this model
Hiring pace, senior design roles, new product launches, fund size announcements, and founder year-in-review updates. YouTubehoneybunny.money

Do Greg’s past exits matter to current earnings
Yes, because past liquidity can fund new teams, experiments, and deal flow without outside capital. TechCrunch

How do advisory roles factor into revenue
Advisory may pay cash, equity, or both, and it boosts pipeline and credibility for the agency and studio. Greg Isenberglatecheckout.substack.com

What multiple should I use to value the agency
I use 4–7× EBITDA depending on growth, concentration, and dependence on the founder.
I avoid SaaS multiples for services.

How risky is it to count unrealized fund marks or studio paper gains
Very risky, so I haircut or exclude until cash hits the bank.
This keeps the model honest and bankable.

Where can I learn more about building investor-ready models and decks
Start with our posts on investor metrics, pitch decks, and AI-era valuation sanity checks here and here.  

Conclusion

Late Checkout revenue explained comes down to cash-flow from the agency, optionality from the studio, and time-shifted upside from fund carry and exits.
Model each stream separately, haircut what’s illiquid, and use first-party signals to update your range.
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