From Green Beret to Blackhawk Pilot to Financial Planner: Nick O'Kelly on Risk, Family, and Starting Over
What a Green Beret turned Blackhawk pilot turned financial planner learned about risk, family, and starting over.
In this episode of The Long Game, Mitch Long talks with Nick O’Kelly about military life, aviation, family, and the road that led him into financial planning. Nick shares how he went from struggling in college to becoming a Green Beret, then a Blackhawk pilot, before eventually starting over in a new career after leaving the military.
They also get into the mindset shift of moving from service into sales, how Nick built his practice, and why his approach to financial planning starts with the end state in mind. It is a grounded conversation about discipline, family, long-term thinking, and helping people make better financial decisions.
WHAT WE TALK ABOUT
Nick O’Kelly’s path from college to Special Forces Serving as a Green Beret in Okinawa Becoming a Blackhawk pilot and flying in special operations Why he left the military and started over The challenge of moving from service into sales How Cadence Wealth Partners approaches financial planning Why Nick starts with the end state in mind Helping clients stay steady when markets get shaky Family, coaching, and being intentional with time Why trust and referrals matter in a growing practice
CHAPTERS
00:00 – Mitch and Nick connect over their military family background 00:11 – Nick on high school, college, and joining the military 01:00 – Special Forces training and becoming a Green Beret 01:30 – Serving in Okinawa and starting a family 01:50 – Aviation, flight school, and becoming a Blackhawk pilot 02:10 – Flying with the 160th Special Operations Aviation Regiment 02:26 – Mitch on growing up in a military family 02:47 – Why Nick left the military 03:24 – Building a plan before leaving service 03:40 – Becoming a finance nerd and earning the CFP designation 04:06 – The hardest part of starting in the business 04:30 – The mindset shift from quiet professional to finding clients 05:15 – Mitch on sales, listening, and helping people solve problems 06:18 – Nick explains Cadence Wealth Partners and how they plan backward 07:00 – How they review plans and keep clients focused long term 07:37 – Market swings, fear, and staying the course 09:06 – Nick on family, kids, and youth sports 10:27 – Coaching baseball and protecting time with family 11:35 – The joke behind “undefeated dad” 12:13 – Military culture, parenting, and adjusting expectations at home 13:24 – Nick on building value and growing through referrals 14:18 – Mitch on relationships that have lasted decades 14:58 – Why trust matters more than transactions 15:00 – Nick on growth, hiring, and expanding the practice