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Gregory Milano on Strategy, Resilience, and Long-Term Thinking
Stand by, this episode is jam packed full of great info! This week, Ryan Derousseau, CFP®, EA, sits down with Gregory Milano, founder and CEO of Fortuna Advisors, to unpack his journey from investment banking to building a strategic consulting firm that has now endured for nearly 17 years.
Gregory shares how Fortuna Advisors was born out of the financial crisis, after his specialty group at Credit Suisse was let go. While the moment felt uncertain, it ultimately created the opening to build the exact business he had been envisioning: one that allowed him to work deeply with a small number of companies instead of superficially with many.
Drawing on his engineering background, early career experience inside large manufacturing and aerospace companies, and decades as an advisor, Gregory offers a candid look at what really happens inside organizations, and why textbook solutions often fall apart in the real world. He also opens up about the extreme volatility of running a consulting business, the hard lessons learned during downturns, and how Fortuna evolved to survive and grow.
In this episode, you’ll learn:
• How Fortuna Advisors was founded during the financial crisis
• Why walking away from investment banking pay was one of the hardest decisions
• How an engineering background shaped Gregory’s approach to strategy and problem-solving
• What extreme revenue volatility looks like in a consulting business
• Why recency bias is dangerous during good times
• How being careful with fixed costs protects a business in downturns
• Lessons learned from product ideas that were “too early” for the market
• How Fortuna is making value-based management accessible to smaller companies
• Why successful leaders balance short-term execution with long-term investment
• Practical advice for solopreneurs on timing, flexibility, and rolling with change
This episode is a grounded, experience-driven conversation about resilience, adaptability, and building a business that can survive both boom times and inevitable downturns.
—-
Connect with Gregory Milano
LinkedIn: https://www.linkedin.com/in/greg-milano/
Website: https://fortuna-advisors.com/
Connect with Ryan Derousseau, CFP
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/ryanderousseau
Website: https://thinkingcapfinancial.com
View all episodes
By Ryan Derousseau, CFP®, EAStand by, this episode is jam packed full of great info! This week, Ryan Derousseau, CFP®, EA, sits down with Gregory Milano, founder and CEO of Fortuna Advisors, to unpack his journey from investment banking to building a strategic consulting firm that has now endured for nearly 17 years.
Gregory shares how Fortuna Advisors was born out of the financial crisis, after his specialty group at Credit Suisse was let go. While the moment felt uncertain, it ultimately created the opening to build the exact business he had been envisioning: one that allowed him to work deeply with a small number of companies instead of superficially with many.
Drawing on his engineering background, early career experience inside large manufacturing and aerospace companies, and decades as an advisor, Gregory offers a candid look at what really happens inside organizations, and why textbook solutions often fall apart in the real world. He also opens up about the extreme volatility of running a consulting business, the hard lessons learned during downturns, and how Fortuna evolved to survive and grow.
In this episode, you’ll learn:
• How Fortuna Advisors was founded during the financial crisis
• Why walking away from investment banking pay was one of the hardest decisions
• How an engineering background shaped Gregory’s approach to strategy and problem-solving
• What extreme revenue volatility looks like in a consulting business
• Why recency bias is dangerous during good times
• How being careful with fixed costs protects a business in downturns
• Lessons learned from product ideas that were “too early” for the market
• How Fortuna is making value-based management accessible to smaller companies
• Why successful leaders balance short-term execution with long-term investment
• Practical advice for solopreneurs on timing, flexibility, and rolling with change
This episode is a grounded, experience-driven conversation about resilience, adaptability, and building a business that can survive both boom times and inevitable downturns.
—-
Connect with Gregory Milano
LinkedIn: https://www.linkedin.com/in/greg-milano/
Website: https://fortuna-advisors.com/
Connect with Ryan Derousseau, CFP
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/ryanderousseau
Website: https://thinkingcapfinancial.com