The Anti-VC: Greg Isenberg and Late Checkout

How Greg Isenberg is Rewriting Company Building Rules

This isn't just another investor story. It's about someone who looked at the venture capital model - with its 2/20 fees, 10-year fund cycles, and obsession with unicorns - and decided to build something entirely different.

Welcome to the world of Late Checkout Capital, where small bets and community ownership are replacing the traditional venture model. And where Greg Isenberg is proving that in the era of digital communities, the real opportunity isn't in hunting unicorns - it's in nurturing foals.

Before we start, here’s a fun little trivia; last year I publicly applied for Late Checkout’s Growth Manager role (with a Twitter post). It went semi-viral, and had a great conversation with Theo (Greg’s co-founder). Even though I didn’t get the role, I appreciate their honesty in the process. They still have plenty of open roles, in case you are in search of a new job.

TLDR

Greg Isenberg is building a different kind of investment firm. While VCs write million-dollar checks hunting unicorns, Late Checkout writes $100K-$500K checks buying undervalued digital communities. Through his "buy, build, and bridge" strategy, Greg is proving that building ten $100M companies might be smarter than chasing one billion-dollar outcome. This isn't just another investment thesis - it's a fundamental rethinking of how value is created in the digital age.

What’s To Come In This Issue:

• How the traditional VC model is breaking, and why community-based businesses are the future

• From selling his first startup at 22 to developing a contrarian investment thesis, Greg’s Journey

• Inside Late Checkout's "buy, build, and bridge" methodology for turning small communities into valuable assets

• How Greg's philosophy translates into practice through real community acquisitions and growth

• Deep dive into the manifesto that's challenging traditional notions of business building

• Where Greg sees the next wave of opportunity in digital community building

The Great Disillusionment

Greg himself

The venture capital model is not for everyone. For every unicorn success, thousands of sacrifices are made. The traditional VC world has a simple formula: Raise big money. Write big checks. Hunt unicorns. Pray for the one investment that returns the entire fund.

This model worked in an era where building software companies required millions in capital. But something has shifted in the digital landscape. While venture capitalists are still writing bigger checks and chasing bigger exits, a new kind of opportunity has emerged in their blind spot.

Through his writing, Greg identifies three fundamental shifts in the market:

1) The Great Unbundling

The era of monolithic platforms is ending. Where Facebook once dominated all social interaction, we're now seeing the rise of focused, niche communities.

• Discord communities are turning into million-dollar businesses

• Subreddits are launching successful products

• Facebook Groups are becoming marketplaces

• Slack channels are evolving into media companies

These aren't just user groups - they're micro-economies waiting to be built. Yet traditional investors largely ignore these opportunities. Too small. Not scalable enough. No clear exit path. The very reasons VCs passed on these communities were exactly what makes them valuable.

2) The Creator Evolution

The first wave of the creator economy was about individuals building personal brands. The second wave, as Greg notes in his newsletter, is about creators building sustainable businesses. They don't just want followers - they want ownership. They don't just want reach - they want revenue.

3) The Investment Desert

Between the angel checks under $50,000 and the VC checks over $1 million lies a vast desert of opportunity. Communities too successful for angel investment but too "small" for traditional venture capital. It's in this desert that Greg spotted his oasis.

There is an opportunity exists in three intersecting trends:

Greg spotted this early on

This isn’t just a gap in the market. It is a completely overlooked market in itself.

Greg's Journey

Before Greg became the community kingpin, he lived the traditional startup life. At 13, he was already showing signs of entrepreneurial spirit, flipping items on eBay and learning the fundamentals of value creation.

By 22, he had already tasted success, selling his first company, 5by, to StumbleUpon. But instead of following the typical founder path - raising bigger rounds, chasing bigger exits - Greg started noticing patterns that others missed.

Then came the chapter that would reshape his entire perspective on business building. As a product leader at WeWork, Greg had a front-row seat to one of the most spectacular implosions in startup history. He watched as billions in venture capital transformed into valuable lessons about the dangers of growth at all costs.

The experience crystallized something he had been thinking about since his early entrepreneurial days: Maybe the real opportunity wasn't in building what VCs wanted to fund. Maybe it was in building what customers actually wanted to use.

The Thesis Evolution

This realization led to a series of experiments. Instead of raising a traditional fund, Greg started testing a different approach. Small check sizes. Quick turnarounds. Active operation instead of passive investment.

Each deal taught him something new about what worked in the new digital economy:

These lessons would eventually form the foundation of Late Checkout's investment thesis.

The Investment Strategy

Greg's approach to investing bears little resemblance to traditional venture capital. Through his Late Checkout newsletter and Multipreneur Manifesto, he outlines a methodology that's more reminiscent of old-school business building than modern startup investing.

The Core Thesis

"Stop trying to build one billion-dollar company," he wrote in his manifesto. "Build ten $100 million ones instead."

This isn't just a catchy phrase - it's the foundation of a completely different approach to value creation. While VCs spread big bets across many companies hoping for one massive winner, Greg makes focused bets on smaller opportunities he can actively grow.

The Acquisition Criteria

Through his published content, Greg outlines what he looks for:

Check Size Sweet Spot

• Investments between $100K-$500K (even less for beginners)

• Too small for institutional capital

• Big enough to have proven traction

• Small enough to be overlooked

Community Fundamentals

• Engaged user base

• Clear niche focus

• Basic monetization in place

• Single operator (or a small team) running things

Growth Potential

• Multiple revenue stream possibilities

• Cross-promotion opportunities

• Tool and infrastructure needs

• Scaling potential

The Operating Principles

But what truly sets Late Checkout apart isn't just what they buy - it's how they operate. Greg's published frameworks show a systematic approach to community growth:

The Buy Phase

• Find undervalued communities

• Evaluate engagement metrics

• Assess monetization potential

• Structure intelligent deals

The Build Phase

• Improve user experience

• Add revenue streams

• Enhance tools and systems

• Maintain community authenticity

The Bridge Phase

• Connect complementary communities

• Share resources across properties

• Build common infrastructure

• Create network effects

Growth Framework

Unlike the traditional venture model of "grow at all costs," Greg advocates for what he calls "sustainable scaling." This includes:

1. Revenue First

• Focus on actual money-making

• Multiple revenue streams

• Clear unit economics

• Sustainable growth rates

2. Community Health

• Member engagement metrics

• Content quality measures

• Moderation systems

• Culture preservation

3. Operational Efficiency

• Shared resources across properties

• Common technology infrastructure

• Knowledge transfer systems

• Team optimization

This framework isn't theoretical - it's battle-tested across multiple acquisitions and shared openly through Greg's content and case studies.

Case Studies in Community Building

Through his Late Checkout newsletter and public content, Greg shares his approach to community acquisition and growth. Let's look at how his frameworks translate into practice.

The Buy-Build-Bridge Model

"Buy, Build, and Bridge isn't just a strategy, it's a repeatable system for turning undervalued communities into thriving businesses."

Greg Isenberg

We talked about it above, but this system shows up consistently across his investments:

Islands: The Community-First Product

Perhaps the most interesting implementation of Greg's thesis isn't about buying communities - it's about building products for them. Through his public content, he shares how Islands emerged from studying community needs:

Islands X WeWork

1. Find Existing Behavior

• Study how communities currently operate

• Identify common pain points

• Look for manual workarounds

• Spot repetitive tasks

2. Build Targeted Solutions

• Focus on specific use cases

• Keep it simple and focused

• Solve real problems

• Listen to user feedback

Islands was acquired by WeWork, where Greg became the Head of Product Strategy.

Pattern Recognition

Across his investments and content, clear patterns emerge in what Greg looks for:

1. Community Characteristics

• Natural gathering points

• Organic engagement

• Clear shared interests

• Basic monetization potential

2. Growth Indicators

• Word-of-mouth growth

• Active discussions

• Regular user-generated content

• Strong retention

3. Monetization Opportunities

• Multiple revenue stream potential

• Clear value proposition

• Willing-to-pay audience

• Scalable economics

Key Learnings

Through his newsletter, Greg shares crucial insights from implementing this strategy:

Community First, Product Second

• Don't disrupt what's working

• Enhance existing behavior

• Keep community trust

• Build what users need

Value Creation Over Growth

• Focus on sustainable metrics

• Build multiple revenue streams

• Maintain healthy unit economics

• Grow through value, not hype

The Multipreneur Philosophy

While others were chasing unicorns, Greg was developing what he calls "The Multipreneur Manifesto" - a different vision for building wealth and value in the digital age.

The Core Philosophy

"The future belongs to people who can spot undervalued assets, know how to grow them, and can hold them forever" Greg writes in his manifesto.

This isn't just about buying businesses - it's about fundamentally rethinking how value is created in the digital age. The manifesto lays out several key principles:

1. Small is Beautiful

• Don't chase billion-dollar outcomes

• Focus on sustainable businesses

• Build multiple revenue streams

• Create compound growth

2. Own, Don't Rent

• Build lasting assets

• Control your destiny

• Create real equity

• Think in decades

3. Operate, Don't Speculate

• Active management over passive investing

• Hands-on growth

• Operational excellence

• Value creation through improvement

The Traditional VC Contrast

Greg's approach stands in stark contrast to traditional venture capital:

The Operating Framework

Through his content, Greg outlines a systematic approach to multipreneurship:

Portfolio Strategy

• Diversified but focused investments

• Complementary businesses

• Shared resources

• Network effects

Value Creation

• Improve operations

• Add revenue streams

• Build better tools

• Enhance user experience

Long-term Vision

• Build lasting businesses

• Create compound growth

• Develop infrastructure

• Foster ecosystems

The Long Game

Unlike the traditional startup world's focus on quick exits, Greg's philosophy emphasizes playing the long game by;

• Building Infrastructure (creating lasting value, developing systems, scaling operations)

• Focusing on Fundamentals (profit, engagement, sustainability)

• Thinking in Decades (network effects, value accumulation, compounding growth)

The Future of Digital Empire Building

Through his writing and podcast appearances, Greg paints a picture of where he sees digital business building heading - and it looks very different from the venture-backed startup world we know today.

The Late Checkout Empire

The Industry Evolution

In his Late Checkout newsletter, Greg outlines several key shifts he sees happening:

1. The Platform Shift

• From massive platforms to niche communities

• From rented audiences to owned spaces

• From scale obsession to engagement focus

• From growth hacking to community building

2. The Investment Evolution

• From fund structures to permanent capital

• From passive investing to active operation

• From unicorn hunting to zebra building

• From exit focus to perpetual ownership

3. The Business Model Shift

• From single revenue streams to multiple

• From user growth to user value

• From venture scale to sustainable scale

• From blitzscaling to steady growth

Greg sees several major opportunities emerging, which are all growth potentials. These include (but are not limited to);

Community Infrastructure;

• Tools for community operation

• Analytics and insights platforms

• Monetization infrastructure

• Growth frameworks

Digital Property Development

• Undervalued community acquisition

• Professional management

• Value-add operations

• Network building

New Operating Models

• Personal holding company structures

• Permanent capital vehicles

• Operational playbooks

• Scalable systems

Market Opportunities

Through these shifts, Greg identifies several key areas ripe for the multipreneur approach.

Vertical Communities

• Professional networks

• Hobby groups

• Interest-based communities

• Learning circles

Creator Infrastructure

• Monetization tools

• Engagement platforms

• Analytics systems

• Growth frameworks

Digital Property Management

• Community operations

• Content management

• Audience development

• Revenue optimization

The Next Phase

Looking ahead, Greg envisions a new kind of digital economy where value creation, a community-first approach, and long-term vision dominate.

In my personal opinion, this is the ultimate way for majority of the entrepreneurs. Building a unicorn is exhausting. It is only worth it if you have the necessary ambition.

Personally, I prefer a smaller, steady, and profitable income. But it might be still risky to have multiple, small bets. Thus, my own reflection on the multipreneurship thesis is this;

One main cash flow business > Smaller digital business > Alternative investments

I believe you should focus on creating a single cash flow business first. Then, automate it as much as possible and invest in smaller niche businesses. All the excess profit goes to an investment portfolio afterward.

A Final Thought

As Greg writes in his newsletter, "The future belongs to those who understand that real value isn't in the platform - it's in the people who call it home."

This vision represents more than just a new investment thesis. It's a fundamental rethinking of how value is created and captured in the digital age. While venture capital continues to chase the next big thing, Greg and Late Checkout are building an empire of small, profitable, sustainable businesses - proving that sometimes the best way to build something big is to think small.

See you in the next edition,

BA