The feeling of a "win" differs by company scale. In a large enterprise, success is the visceral impact of a launch reaching millions of customers instantly. In a startup, success is more about hitting internal milestones—shipping a feature or securing funding—which are incremental but deeply rewarding.

In deep enterprise plays, early ARR can be a misleading metric. The founder focused on a small number of customers with massive expansion potential ($10M+ ARR), prioritizing deep integration and value creation over premature scaling and surface-level growth.

Counterintuitively, targeting significantly larger deals forces extreme focus. A $5 billion fundraising goal might involve only 10 conversations, whereas a $5 million goal could involve 1,000. This massive scale filters for serious professionals and eliminates the distractions common in smaller-scale endeavors, simplifying the process.

Large companies view opportunities representing less than 1-10% of their total revenue as distractions. This creates a "sweet spot" for startups to build significant businesses in areas ignored by giants, turning a distraction into an opportunity.

For innovation arms inside massive companies like Cisco, early revenue is irrelevant—a $5 million success would be laughed at. The true measure of success is creating strategic options for the parent company to navigate future market shifts, not hitting traditional startup KPIs.

A working business model isn't always the right one. The founder pivoted Amigo AI away from a growing SMB segment because, while he saw a clear path to $10M ARR, he no longer believed it could become a billion-dollar company, making the opportunity cost too high.

Aim for "good enough" financial estimates to differentiate multi-million dollar opportunities from thousand-dollar ones. This high-level sorting is more valuable and efficient than creating detailed, yet still speculative, forecasts for every idea.

When establishing a new M&A function, the primary challenge is getting senior leaders to move beyond broad statements and make concrete strategic choices about which opportunities to actively ignore. This focus is crucial for effective execution and prevents wasted energy on opportunistic, unfocused deals.

Not all business problems are created equal. Time savings often translate to five-figure cost savings, which may not be compelling. The most powerful executive problems are "six-figure problems"—major risk mitigation (avoiding lawsuits), significant revenue generation, or replacing other large costs.