The Multipreneur: He Makes $10M/Year With 6 Businesses | Starter Story

October 8, 2025

AI Summary

5 min read

Greg Eisenberg runs a holding company called Late Checkout that generates eight figures in revenue and mid-seven figures in profit across six businesses. He started them all with zero dollars. The key insight from his story is not about hustle or luck — it is a repeatable system for identifying problems, building an audience around them, and then creating a product. He calls this the ACP funnel, and he has used it for 15 years.

Eisenberg’s path began with a formative failure. After selling his first startup to WeWork, he became head of product there and watched the company collapse from a $47 billion valuation into a cash crisis. That experience taught him a hard lesson: he never wanted to build an unprofitable venture-backed company again. He wanted a model that combined freedom with the creativity of building multiple businesses. That model became "multipreneurship" — running several smaller, profitable businesses instead of one giant, fragile one.

The ACP Funnel: Audience, Community, Product

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What you'll learn

1 (01:28) **Introduction: The Multipreneur Making $10M/Year** - Pat introduces Greg Eisenberg, who runs six businesses generating over $10M in revenue with $5M+ profit, all started with zero dollars.
2 (02:40) **Who Greg Is and His Holding Company** - Greg describes his holding company, Late Checkout, and breaks down his six businesses.
3 (04:31) **Origin Story: From School Shooting to WeWork** - Greg shares his background, including a traumatic school shooting at age 17 that motivated him to pursue big goals.
4 (06:59) **First Business: LCA Innovation Agency** - Greg launches LCA, an innovation agency charging $1.5M/year per client (Nike, Dropbox, Shopify, TikTok).
5 (10:15) **Transition to Multipreneur: Learning from Failure** - Greg tried starting a second business (Nice Break) directly with a product, which failed.
6 (11:01) **Scaling with Boring Marketer and AI Tools** - Greg started a Twitter account called Boring Marketer, built a community, and created an AI-assisted SEO tool.
7 (11:30) **Hiring Strategy: Nerds in Residence and Cold DMs** - Greg explains how he hires operators to run his companies.

+ Full timestamped outline available in the app

Guests on this episode

Greg Eisenberg

Show Notes

The Multipreneur: He Makes $10M/Year With 6 Businesses

This is the breakdown of how Greg Isenberg makes over $10M/year with 6 businesses.

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------ Keywords: online business, business ideas, startup advice, startup stories, micro saas, business growth

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