Ep 505: Using A "Pillow Test" To Make The Hard Business Decisions On The Way To $3.5B AUM with Andrew Rosen

How do you know you're making the right decision, especially when every option comes with trade-offs? Whether you're making career decisions or leading a growing advisory firm, today's guest offers practical lessons on building a business that aligns with your values while creating long-term success.  Andrew Rosen is the Executive Chairman of Diversified, LLC, and in this episode, he shares the decision-making framework he calls the "pillow test," a simple but powerful way to evaluate career moves, business opportunities, and strategic decisions. Listen in as Andrew explains how this mindset shaped his career, from choosing a lower-paying role with greater long-term opportunity to navigating acquisitions, ownership transitions, and decisions around private equity investment. You'll learn how Diversified evolved from founder-led ownership to a partner-owned firm, what matters just as much as technical expertise when earning clients' trust, and more. For show notes and more visit: https://www.kitces.com/505