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| A new way to build… | The "Constellation Software" model is one of the most whispered-about secrets in elite finance. Mark Leonard built a $70B empire by buying "boring" vertical software companies—the ones that run grain elevators, local libraries, or parking garages—and holding them forever. | But the old playbook had a massive overhead problem: The Human Tax. Even if the software was "boring" and "sticky," you still needed a small army of support reps, manual testers, account managers, and data entry clerks for every single acquisition. This meant you couldn't justify buying companies below a certain size because the "Management Fee" (the cost of the humans required to run it) would eat all the profit. | Today, that barrier has evaporated. AI has turned the "Permanent Equity" model into a high-margin automation game. | | Ship the message as fast as you think | | Founders spend too much time drafting the same kinds of messages. Wispr Flow turns spoken thinking into final-draft writing so you can record investor updates, product briefs, and run-of-the-mill status notes by voice. Use saved snippets for recurring intros, insert calendar links by voice, and keep comms consistent across the team. It preserves your tone, fixes punctuation, and formats lists so you send confident messages fast. Works on Mac, Windows, and iPhone. Try Wispr Flow for founders. | Start flowing free |
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| | Three massive shifts have collided to make the "Automated Rollup" the highest-leverage play in tech right now: | 1. The Death of the Human Overhead | Five years ago, a $2M ARR company required 10–15 people to function. Today, an AI-native operator can use "Agentic Workflows" to automate 80% of those roles. | Customer Support: LLMs with access to your documentation handle 90% of tickets with zero latency. DevOps/Maintenance: AI coding assistants manage bug fixes and security patches for legacy codebases. Reporting/Admin: Automated agents handle the complex cross-company reporting that used to require a Finance team.
| 2. The "Zombie Startup" Clearance Sale | The VC market of 2021 was a fever dream. Thousands of companies raised $10M–$20M rounds at $100M valuations. Many of these companies are actually great businesses—they have $3M–$5M in ARR and loyal customers—but they are "failures" in the eyes of VCs who only care about $1B+ outcomes. | These VCs have written these deals to zero. The founders are burned out from trying to "grow at all costs." The Opportunity: You can buy these assets for 1x–2x revenue, strip out the venture-fueled bloat, and turn them into cash-flow machines overnight.
| 3. The Return of the "Rational Operator" | For the first time in a decade, high-status talent is looking at "boring" $2M ARR companies as the ultimate prize. Experienced operators are realizing that owning 50% of a profitable, automated niche business is better than owning 2% of a "Unicorn" that might never exit. | | Are you looking to fundraise? Here is how I can help: | |
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