How Greg Isenberg Makes Money is simpler than the mystique suggests and more diversified than a single “agency income” line.
I’m breaking down each income stream with sources, my take on how the flywheel works, and what founders can copy without copying the man.

For a deeper profile, see our blog post: Greg Isenberg Net Worth: All You Must Know About Him.

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1) The quick map of Greg’s income streams

I start with the five buckets he’s known for.
Late Checkout (agency, studio, fund).
Company exits (5by, Islands).
Advisory roles (Reddit, TikTok).
Media (YouTube, newsletter, podcast, courses).
Angel and fund bets.
His 2024 “Year-in-Review” confirms he actively tracks and optimizes the mix. YouTube

Why it matters.
Services throw off cash today.
Ownership creates step-function upside tomorrow.
Distribution lowers acquisition costs across all of it.

2) Late Checkout, the operating engine

Late Checkout is positioned as a design-and-product firm with a studio and fund attached.
That means client revenue now and optionality later. Late Checkout
He describes Late Checkout as a holding company that “builds community-based internet businesses,” which frames everything as ownable distribution. Greg Isenberg

Founder takeaway.
Run a service that cash-flows.
Reinvest the profits into products and equity.
For metrics to watch, see our blog post: Investor Metrics that Matter: A Founder’s 2025 Guide.

3) How the agency makes money (and why clients pay)

Agencies make money on scoped projects, retainers, and accelerators.
Late Checkout sells product strategy, design, AI-native workflows, and GTM work. Late Checkout
Pricing power comes from brand, proof, and speed.

Signals to price higher.
Clear POV on “community-first” products.
Credible founder-led team.
Public content that pre-sells expertise.
For pitch materials that support premium pricing, see our blog post: The Ultimate Guide to Pitch Decks.

4) The studio + fund: small checks, big upside

Late Checkout also creates and invests in products and early-stage companies.
Public trackers show investments in consumer and dev-tools, which I treat as asymmetric upside versus core agency cash. MessariPitchBook

Reality check.
Studio/fund returns are lumpy and illiquid.
They compound over multi-year cycles.
For valuation sanity, see our blog post: AI Startup Valuations: The Reality Check You Need.

5) Exit #1: 5by → StumbleUpon

Greg founded video discovery app 5by and sold it to StumbleUpon in 2013.
Terms were undisclosed, but the acquisition is well documented by TechCrunch, Forbes, and others. TechCrunchForbesBetaKit

What that means.
Cash and credibility to self-fund later bets.
Proof he can build, sell, and ship.

6) Exit #2: Islands → WeWork

He later founded Islands, a community messaging app, which WeWork acquired.
Post-acquisition, he served briefly as Head of Product Strategy at WeWork. Greg IsenbergLinkedIn

Why founders should care.
A second exit de-risks the next chapter.
It also expands the network for advisory and deal flow.

7) Advisory roles: cash, equity, or both

Greg cites advisory work with Reddit and TikTok.
His site and profiles list these roles, and NFX references the TikTok advisor title in its intro. Greg Isenberglatecheckout.substack.comNFX

How advisors get paid.
Some mix of cash, options, and brand exposure.
When it’s options, the upside is back-weighted and uncertain.

8) Media engine: YouTube, newsletter, podcast

He publishes aggressively across YouTube, podcast feeds, and a newsletter. YouTube+1Substack
Direct ad revenue is usually small versus service income, but media drives clients, course sales, and deal flow.
Third-party trackers show modest YouTube ad estimates compared to agency economics, which supports this point. StarStat.yt

Copyable move.
Publish once.
Repurpose everywhere.
Route interest into high-margin offers.

9) Courses and community products

He’s sold cohort courses like Community College and web3-era programs like Crypto College.
Courses turn attention into cash and seed future clients.

Design principle.
Teach the playbook you sell.
Sell the playbook you teach.

10) Boring Ads and Boring Marketing

You’ll see him associated with Boring Ads and Boring Marketing.
Boring Ads features his testimonial and notes he invested, which signals involvement rather than P&L specifics. boringads.com
Boring Marketing markets AI-driven organic growth and automation services. boringmarketing.com

How it fits.
Parallel operators create additional cash flow and cross-sell into Late Checkout clients.
Treat any “ad spend” numbers as client budget, not agency revenue.

11) The Year-in-Review growth signal

In his 2024 review, Greg discusses portfolio allocation and performance.
Summaries highlight a 38% net-worth increase, which I treat as self-reported but directionally useful. YouTubesummiz.ai

Translation.
He’s compounding by simplifying, focusing, and letting distribution do work.
For raising while you simplify, see our blog post: Raising Capital in 2025: The Complete Founder’s Playbook.

12) The holding-company flywheel

The model is clean.
Agency cash funds studio experiments.
Winning products and investments add equity.
Media lowers CAC for everything.
His own about page frames Late Checkout exactly this way. Greg Isenberg

Why this wins.
Cash today.
Equity tomorrow.
Distribution forever.

13) How the dollars likely stack in a typical year

Services and retainers are the base.
Courses, workshops, and speaking stack on top.
Media monetizes lightly but feeds the pipeline.
Angel and fund marks show up sporadically.
Advisory equity is the wild card.

Manage your mix.
Score each stream by cash speed, effort, and upside.
Shift time toward high-margin, high-optionality work.
For term-sheet tactics when upside appears, see our blog post: How to Negotiate Your First Term Sheet Like a Pro.

14) Pricing power from niche POV

Community-first design is a differentiated POV.
Specialization supports higher rates and lower churn.
Proof beats pitch.
Publish the proof in public.

Internal link for positioning.
For pricing and perception lessons, see our blog post: Why Alex Hormozi Says Marketing Perception Can Outperform Product Quality.

15) Risk profile you shouldn’t ignore

Agencies are people-heavy and cyclical.
Advisory equity is illiquid.
Angel checks can go to zero.
Media platforms change algorithms.

Counter.
Diversify streams.
Own distribution.
Hold more cash than you think.

16) What founders can copy this quarter

Ship a paid service anchored to a clear POV.
Start a weekly publishing cadence.
Productize one internal workflow into a mini-offer.
Make a tiny LP or angel check only where you also add value.

Do this next.
For outreach templates, see our blog post: Elevating Your Investor Outreach: 13 Follow-Up Email Templates.

17) How to think about valuation and multiples

Value the agency on EBITDA and a private-market multiple.
Value the studio/fund at cost or last round, then haircut for liquidity.
Ignore vanity metrics.
Institutionalize finance even if you’re indie.

Go deeper.
See our blog post: Series A Valuation: How to Determine Your Startup’s Worth.

18) Media → Deal flow → Ownership

The real power of media is not AdSense.
It’s proprietary deal flow.
Warm intros.
Better talent.
Higher conversion.
Greg’s channel cadence shows this is a deliberate growth engine. YouTube

Founder move.
Track Media-to-Revenue as a KPI.
Treat content like distribution infrastructure.

19) The “services-to-equity” ladder

Start with cash services.
Earn advisory equity when you drive outcomes.
Parlay into angel checks.
Spin out products with clients as design partners.

Related reads.
For a contrarian wealth lens, see our blog post: Why Alex Hormozi Prioritizes Profitability Over Revenue.

20) 2025 outlook for the Isenberg model

AI-native services increase margins.
Studio bets get cheaper to test.
Media gets louder and more shoppable.
Expect more cash from services and more optionality from products and investments.
The core play doesn’t change.
Own audience.
Own IP.
Own equity.

FAQs

How does Late Checkout actually make money
It sells product strategy, design, AI workflows, and GTM work on projects and retainers. Late Checkout

Did Greg really sell two companies before Late Checkout
Yes.
5by was acquired by StumbleUpon and Islands was acquired by WeWork. TechCrunchGreg Isenberg

Are his advisory roles confirmed anywhere public
Yes.
He lists Reddit and TikTok on his site and Substack profile, and NFX references TikTok advisor. Greg Isenberglatecheckout.substack.comNFX

Is media a major cash driver for him
It helps, but the bigger lever is how media drives clients and deal flow.
Ad revenue itself is typically smaller relative to services. StarStat.yt

Does he run a fund
Yes, Late Checkout operates a studio and a fund investing in early-stage, community-centric companies. Messari

What’s the point of Boring Ads and Boring Marketing in his mix
They add parallel cash-flow and distribution ops, and cross-sell into his ecosystem. boringads.comboringmarketing.com

Did he disclose his exact income or net worth
No exact dollar figures.
His 2024 review provides directional updates and allocation insights. YouTube

What’s the single move a founder should copy first
Launch a specialized service tied to a strong POV and publish weekly to create inbound demand.

If I want to raise money while I build this, where do I start
Start with our blog post: Raising Capital in 2025: The Complete Founder’s Playbook.

Where can I read more comparisons to other operator-creators
See our posts on Sam Altman Net Worth 2025 and Alex Hormozi Net Worth 2025.

Conclusion

How Greg Isenberg Makes Money comes down to a flywheel that any founder can adapt.
Cash-flowing services fund product and equity.
Distribution reduces CAC and increases pricing power.
Optionality compounds over years, not weeks.
Subscribe to Capitaly.vc Substack (https://capitaly.substack.com/) to raise capital at the speed of AI.

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