The Long Game with Mitch Long
Mitch Long spent thirty years in insurance — long enough to know what actually works. Now he sits down with business owners and founders for the conversations that don't make it onto LinkedIn: how they started, what they got wrong, and why the basics still win.
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About the show
The Long Game is Mitch Long talking with business owners, founders, and people who've been around long enough to have something real to say. He started in insurance with a pager and a roll of quarters; thirty years later he's still showing up. The conversations are about how people got started, what they'd do differently, and why the fundamentals outlast the trends. Every so often Mitch and his son Adam break off into First and Long — their ongoing back-and-forth about the NFL and their long-suffering Steelers, a SportsEpreneur series.
Hosts
Mitch Long
Mitch Long has spent three decades in insurance and runs KazInsurance, a KazSource brand. On The Long Game he draws on that experience to talk with business owners and founders about the slow, unglamorous work of building something that lasts.
Recent episodes
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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.
Full show notes
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
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NASCAR, Family, and Starting Over with Chip Goode
What 19 years on pit road taught Chip Goode about pressure, family, and building a second career.
Full show notes
In this episode of The Long Game, Mitch Long talks with Chip Goode about sports, NASCAR, family, and how he made the jump from pit road into insurance. It starts with football and the NFL Draft, but the bigger story is about work, timing, and knowing when it is time to build something new.
Chip shares how he spent 19 years on NASCAR pit crews, what that life demanded, and why he eventually needed a different path for his family. He also gets into the move into insurance, buying an agency, and what it means to have more control over your work and your time.
WHAT WE TALK ABOUT The NFL Draft and why both Mitch and Chip still believe in building through the line Why Aaron Rodgers feels like more trouble than he is worth Growing up in Statesville around racing From football and basketball to NASCAR pit crews What pit road demands physically and mentally The pressure of never missing a race Marriage, kids, and the cost of being gone every weekend Knowing when it was time to leave NASCAR How Chip found his way into insurance Why owning an independent agency gave him more freedom
CHAPTERS 00:20 – Mitch checks in with Chip and the conversation starts with business 00:46 – Rate increases, tighter underwriting, and a tougher insurance market 01:10 – NFL Draft talk and why Chip likes the Panthers building up front 02:34 – Steelers fans, draft night, and the Aaron Rodgers question 04:29 – Why teams get stuck chasing average instead of finding their quarterback 06:44 – Chip on growing up in Statesville and being around racing early 07:00 – Football, basketball, UNC Charlotte, and getting into NASCAR 07:53 – Chad Little, Jeff Burton, Juan Pablo Montoya, and life on pit crews 09:06 – How Chip first got into the sport through his dad 10:43 – Getting into Victory Lane as a kid 11:00 – From helping on weekends to jumping over the wall in 1998 12:27 – The physical and mental side of being on a pit crew 13:52 – Meeting his wife and balancing racing with family life 15:00 – A streak of 730 straight Cup races 16:26 – Why family eventually changed the way he saw the job 18:04 – Coaching, showing up for kids, and the value of flexibility 20:27 – His daughters, college, and musical theater 22:07 – Why Chip moved from NASCAR into insurance 23:23 – The call that pushed him toward Farm Bureau 24:00 – Getting licensed while still working race weekends 25:01 – The chance meeting that led to buying an agency 26:13 – What independence changed for Chip as an owner 29:00 – Mitch on starting over in sales and learning to live on what you produce 30:00 – Faith, timing, and the checks that showed up right when they were needed
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Slade Lewis on Leadership, Follow-Up, and the Future of Insurance
What strong leaders do, why follow-up still wins, and how insurance is changing fast without losing the human part.
Full show notes
In this episode of The Long Game, Mitch Long talks with Slade Lewis about how he got into insurance, the turns his career took along the way, and how he ended up in a leadership role at Pinnacle. They also get into sales, management, technology, and what has changed in the business over time.
It is a practical conversation about relationships, follow-up, and how to lead people well. It also gets into AI, rising premiums, and why clients still need a real person they can call when something goes wrong.
WHAT WE TALK ABOUT How Slade Lewis got into insurance Starting out at Jefferson Pilot Leaving insurance and coming back What makes a strong manager Why follow-up still matters in sales How Zoom, DocuSign, and technology changed client meetings Where AI is starting to change insurance What rising premiums are doing to clients and agencies Why the human side of the business still matters Slade’s high school typing champion story
CHAPTERS 00:21 – Mitch kicks off the conversation from the road 01:03 – Slade on growing up in Hampstead and going to UNC 02:30 – A journalism degree with a concentration in advertising 03:09 – Slade’s first job in insurance with Jefferson Pilot 04:00 – Moving from service into sales 04:27 – The bulldog hair company car story 06:14 – Leaving insurance for pharmaceutical sales and coming back 07:20 – Product roles, UnitedHealthcare, and becoming a broker 08:26 – Slade’s current role and how he thinks about leadership 10:48 – The biggest sales challenges in insurance today 12:00 – Why answering calls and following up still separates people 13:34 – How client meetings shifted from face-to-face to Zoom 14:20 – Technology, DocuSign, and doing business across states 14:57 – Why AI may transform agencies faster than expected 15:58 – The caution around database underwriting and automation 16:50 – How AI is already shaping health insurance underwriting 17:41 – Rising health insurance costs and the pressure on employers 18:35 – Standard rate increases in the small group market 19:20 – Looking for options when traditional carriers say no 19:43 – Auto and homeowners insurance costs keep climbing 20:18 – Roof issues, storm risk, and what is driving property costs 21:36 – Slade reveals he was his high school typing champion
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First & Long: The Steelers Are Stuck and We're Not Okay
Welcome to First & Long — a father-son football conversation between Mitch and Adam Long. Steelers fans, NFL obsessives, and yes, they've already argued about this.
Full show notes
In this episode, Mitch and Adam talk about the NFL Draft, the Steelers, the Bills, and a couple of Pittsburgh trip stories that did not exactly go to plan.
They also get into quarterbacks, roster building, fan frustration, and why teams still have to win up front. It is a loose football conversation, but the main point is clear: quick fixes usually are not enough.
WHAT WE TALK ABOUT
Pittsburgh trip stories and hotel disasters Why the draft always starts arguments The case for building the line before chasing a quarterback Why where a quarterback lands matters Whether the Steelers should give Will Howard a shot Why the Steelers feel stuck in the middle Why teams still win in the trenches Whether Buffalo is doing enough around Josh Allen
CHAPTERS
00:01 – Mitch sets up a talk about the draft and Pittsburgh trips 00:18 – Adam’s advice on where not to stay in Pittsburgh 00:43 – The hotel story that went bad fast 01:50 – The legendary bar encounter in Pittsburgh 02:19 – Running into the same guy again in Virginia 02:45 – Mitch and Adam get into the draft 03:06 – Adam on the Raiders, Fernando Mendoza, and Kirk Cousins 05:30 – Mitch makes the case for trading the top pick 09:30 – Why quarterback success depends on where a player lands 12:37 – Mobility, protection, and what the Steelers lacked last year 15:24 – Adam on play calling and helping players succeed 17:25 – What the Steelers should target in the draft 19:57 – Jeremiah Love, offensive line help, and winning in the trenches 23:37 – Mitch on following the draft without pretending to know every prospect 25:16 – The argument for seeing what Will Howard can do 27:42 – Why Adam does not want Aaron Rodgers back 30:31 – The cost of being scared to have a losing season 35:15 – Bo Nix, the Broncos, and what could have been 38:42 – Mitch turns to the Bills and Josh Allen 41:52 – Why Buffalo may be at a key point
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50 Years in Business with Wes Connor
What 50 years in insurance teaches about relationships, change, and why the basics still matter.
Full show notes
In this episode of The Long Game, Mitch Long sits down with Wes Connor to talk about how he got into insurance, what kept him in it, and what 50 years in the business has taught him.
They get into family business, remote selling, hiring challenges, commercial and personal lines, and why life insurance still stands apart from products people are required to buy. It’s a grounded look at what still matters in the business, what has changed, and why the basics still win.
WHAT WE TALK ABOUT
- How Wes Connor got into insurance in 1975 - From kitchen table sales to DocuSign and video calls - Why relationships still matter in a more digital business - Working with family across generations - Hiring challenges in today’s insurance market - Commercial versus personal lines in a changing market - Why life insurance feels different from mandatory coverage - Disability, long-term care, and planning before it’s too lateCHAPTERS
00:20 – Mitch welcomes Wes Connor 00:41 – How Wes got into the insurance business 03:15 – Starting out and falling in love with the work 05:21 – How selling insurance has changed over the years 08:00 – Podcasts, technology, and the next generation in the business 11:00 – Working with family and building an agency over time 12:00 – Hiring challenges and the shortage of new agents 16:23 – Disability insurance, income protection, and planning gaps 16:52 – Wes breaks down his agency’s commercial and personal lines mix 19:19 – Why selling life insurance is more satisfying 21:00 – Real examples of how life insurance changes outcomes for families 23:29 – Long-term care, aging, and staying healthy
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The Long Game: Meet Mitch Long
Why stories beat pitches, why showing up still matters, and what this series is about.
Full show notes
Eric Kasimov sits down with Mitch Long to kick off The Long Game. Mitch has been in the insurance business for over 30 years. He started with a pager and a roll of quarters. He built his book by showing up every Tuesday until people just started handing him the business. Now he's here to have conversations with business owners about how they got where they are — the real version, not the LinkedIn version.
What We Talk About:
- Criminal justice major to insurance salesman
- The 93-year-old woman and the bell story
- Why face-to-face still matters (and why it's not enough anymore)
- Pagers, Blackberries, and the quarantine pivot
- The buggy whip salesman problem
- NIL, college sports, and what it means to stay relevant
Chapters:
- 00:14 – What this show is and how conversations work
- 01:00 – Mitch's path into insurance
- 02:05 – College degrees as ticket punches
- 04:08 – Stories over structure
- 05:48 – The power of getting people talking
- 07:00 – The 93-year-old woman and the bell
- 08:27 – Podcasting as a way to connect
- 10:00 – Feeling heard in a distracted world
- 12:06 – 22 years of working together
- 13:00 – Old school meets new school
- 14:00 – Generation Jones
- 15:00 – Tangents are the point
- 16:08 – Face-to-face vs. Zoom
- 17:15 – NIL and staying relevant
- 19:00 – Aging up in college sports
- 20:17 – Opting in or opting out
- 21:30 – Adjusting how you reach people
- 23:00 – The Walmart joke and resilience
- 23:45 – Pagers, payphones, and quarters
- 25:00 – The quarantine as a reset year
- 26:00 – Blackberry, Gateway, and what happens when you don't evolve
- 28:00 – The buggy whip salesman
- 30:00 – Mitch's grandfather sold matches
- 32:30 – NIL and financial literacy
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