Super Angel Joe Caruso in "Fearless Angel"

His bonhomie masks a keen intelligence that has, for decades, taken note of what makes or breaks founding teams. Joe Caruso is the CEO Whisperer, the Father Confessor to Founders. Joe’s an intrepid angel investor who goes where other angels fear to tread. This makes him a highly sought-after board member or advisor. I was privileged to sit down with him for an hour and to imbibe his wisdom and good humor. Typical Joe Caruso comment: “…you don't train a Labrador to flap its ears. It makes for a lousy butterfly.”

Here are some highlights of what we discussed:

• Joe Caruso Introduction
• Joe Caruso Bio
• How Joe Discovered He Wanted to Be the Father Confessor to CEOs
• How Roxbury Latin School, the One True School, Figured in Joe Caruso’s Formation
• Joe Caruso Drops Out of High School and Enrolls at Northeastern University
• Boston’s Unique Environment for Learning: Jeff Bezos Take Note
• “I'm in the cafeteria … and at the table is a newspaper from the prior June … and they had a list of starting salaries of all the people who graduated, and electrical engineers made more than anyone else, so I said I guess I'll be one of them.”
• “…co-op [work/study program at Northeastern] taught me that engineering wasn't my strong suit.”
• Outstanding Argument in Favor of Northeastern’s Co-op Program
• Delightful Story About Joe Caruso Considering Turning Down Harvard Business School
• Joe Caruso Had No Idea of the Value of Networking While at Harvard Business School!
• “I studied and ... I took no advantage of that [networking at HBS], which in retrospect was a huge missed opportunity.”
• How Doing Turnarounds Got Joe Caruso Involved with Level Up
• “Here's this 19-year-old kid, either freshman or sophomore at Princeton, that was going to drop out to start a company.”
• “It had gaming, location-based. As I kidded with him, it was very buzzword-compliant.”
• “If you give me a bright, passionate, high-integrity entrepreneur, that's the ticket of admission to at least me considering investing.”
• Semyon Dukach’s Answer to “Should I Start a Company?”
• “…you don't train a Labrador to flap its ears. It makes for a lousy butterfly.”
• “None of this is off-topic. … Our topic is human nature.”
• “So, be who you are. That also says, "complement who you are."”
• The Change in Business Plan of Which Joe Caruso is Proudest
• From Measuring Alpha Waves to Helping People Recover from Spinal Injuries
• Leveraging Personal Computers for Lab Automation
• The Particular Hell of VCs with Conflicting Interests
• Sal Daher Reads the Review from Listener bpaul2 – Reminds You to Leave a Review in iTunes
• Joe Caruso’s Favorite Pivot
• Joe Caruso’s First Investment
• Joe Caruso’s Parents Were Survivors of the Depression Era and thus Not Open to Entrepreneurship
• "We've gotta get you out of the basement."
• Joe Caruso’s Apologia for the Value of Boards – Directors vs. Advisors
• What Advice Do You Find Yourself Giving Over and Over?
• Joe Caruso’s Parting Thoughts