His fatal flaw is how he conducts commercial conversations. The way he does it marks him as a lightweight. Not someone you aggressively recommend to your network or invite to give the keynote address at the annual meeting of the financial planners trade association.
What he missed is that "personal" does not mean about him. "Personal," when it comes to the vendor, means how smart you are about your niche expertise, how shrewd you are about presenting yourself, how much integrity you have and how you're disciplined enough not to wind up with a DUI.
In framing his sucess this Baby Boomer states things like, "I can afford to help out my mother financially." Much better would be, "The few past good years allowed me to invest in technology. That makes doing business easier for clients."
Commercial conversations are fierce business tools. They should be all-business. No one cares about anything but their business. Therefore, everything related to their business should be talked about as all-business. There are no exceptions.