While the process of acquiring businesses is exciting, managing a large portfolio of acquired companies shifts the CEO's job dramatically. The role becomes less about the 'chase' of deals and growth, and more about managing personnel issues, retaining key talent from acquired firms, and solving interpersonal conflicts—a draining reality of scale.

Due diligence cannot quantify a team's crucial soft skills. When an acquirer forces change aggressively post-close, they risk an exodus of these skills and key talent, maximizing the chance of the investment failing. A partnership approach that preserves talent for at least the first year is a much safer strategy.

Many M&A teams focus solely on closing the deal, a critical execution task. The best acquirers succeed by designing a parallel process where integration planning and value creation strategies are developed simultaneously with due diligence, ensuring post-close success.

An acquisition target with a valuation that seems 'too good to be true' is a major red flag. The low price often conceals deep-seated issues, such as warring co-founders or founders secretly planning to compete post-acquisition. Diligence on people and their motivations is more critical than just analyzing the financials in these cases.

Instead of a linear process, treat M&A as a spiral. Constantly revisit and adjust deal structure, diligence findings, and integration plans. A discovery in one area (e.g., diligence) should trigger a reassessment of the others (e.g., deal structure), ensuring a cohesive and de-risked outcome.

Three dangerous mindsets, or "coats of conviction," derail M&A deals. They are: reactive positioning (chasing auctions), integration negligence (delaying planning), and the model mirage (trusting an untested financial model). A disciplined, proactive process is the antidote to these common pitfalls.

For iCapital, an acquisition is not complete until both the technology and the people are fully integrated into a "one-eye capital" culture. The CEO emphasizes that people integration is even more critical than tech integration, as a failure on the cultural front means the entire acquisition fails.

The key to post-acquisition integration isn't a perfect plan, but spending significant time on the ground with the acquired team. Leaders must earn the right to lead by demonstrating consistency and empathy over weeks and months, as initial promises are met with skepticism. A single presentation won't win anyone over.

The reality of selling a company is not a simple transaction. It's a grueling, months-long process that functions as a demanding second job for the founder, who must keep it secret from their team while simultaneously running the core business at full capacity.