Episode
Ep 505: Using A "Pillow Test" To Make The Hard Business Decisions On The Way To $3.5B AUM with Andrew Rosen
- Podcast
- Financial Advisor Success
- Published
- Sep 1, 2026
- Duration seconds
- 5432
- Processing state
not_requested
Actions
POST https://stenobird.com/v1/public/podcasts/financial-advisor-success-1002597/episodes/ep-505-using-a-pillow-test-to-make-the-hard-business-decisions-on-the-way-to-3-5b-aum-with-andrew-rosen/transcription-requests
Idempotently request low-priority transcript generation for this episode.GET https://stenobird.com/podcast/financial-advisor-success-1002597/ep-505-using-a-pillow-test-to-make-the-hard-business-decisions-on-the-way-to-3-5b-aum-with-andrew-rosen.md
Read the agent-friendly Markdown representation of this episode resource.
Summary
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