The Dad Edge Podcast

Most of us grow up thinking success means staying busy, staying strong, and never stopping. But what happens when the career that defined you is gone? Michael Kay spent decades as a financial planner and NYU instructor helping high achievers build wealth — until he realized the most important investments had nothing to do with portfolios. He's the host of the Chapter X Podcast and author of How to Craft Your Chapter X, and he's spent years guiding successful men through the emotional and psychological shift from career identity to a purposeful next chapter. He's been married to his college sweetheart Wendy since 1977, is a dad of two, and a grandfather of three.
This conversation goes deep on the patterns we inherit from our fathers, what it actually means to listen instead of just waiting to respond, and why retirement without intention is a trap most men never see coming. If you've ever tied your worth to what you do instead of who you are, this one is for you.
Timeline Summary
[1:02] Larry introduces the June Alliance promo — signed copy of The Pursuit of Legendary Fatherhood plus three bonus courses for new members
[3:01] Michael joins in studio, sharing what it means to be a dad and grandfather first
[3:48] Larry invites Michael to describe growing up with a demanding, workaholic father who didn't spare physical discipline
[5:29] Michael reflects on how watching his father — who had no model himself — taught him what he would never do with his own children
[9:49] Michael shares what he learned from his father's dedication as a sixth-grade teacher who taught every student at their own reading level
[10:42] Michael's musical upbringing — his uncle was good enough to play with Duke Ellington, and Michael took weekly lessons from a New York Philharmonic trumpeter at 14
[17:55] A butcher named Al Roth becomes a turning point — the first man Michael ever saw who loved his family openly, and what that lit up in him
[22:31] Larry asks how Michael and Wendy have navigated 49 years of marriage, especially given the communication models neither of them grew up with
[26:36] Michael breaks down how men and women process differently — and why creating space instead of rushing to solve is the real skill in marriage
[29:47] What deep listening actually looks like in practice, and why a "yeah, but" response signals that no one was listening at all
[34:26] The origin of "Chapter X" — and how an eighth-grade algebra class planted the idea that every next season of life is something to solve for
[40:19] Why the book is not about money — it's about reclaiming the curious, unfinished person you were before your career became your identity
[43:33] The eulogy exercise: Michael and Larry on why writing your own eulogy is one of the most powerful things a man can do to realign his actions with his values
[47:37] The hard truth that 98% of daily activity often isn't in alignment with what you'd want said about you at the end
[49:44] Michael tells his 50-years-younger self to stop taking himself so seriously, start listening better, and soften the edges
Five Key Takeaways
Nothing happens in a vacuum. The way your father treated you was shaped by everything that happened to him before you arrived. Understanding the roots of that behavior doesn't excuse it, but it changes how you carry it forward.
You only break a cycle when something from outside enters your normal. For Michael, that was Al Roth — a marine turned butcher who loved his family loudly and openly. You can't change patterns you can't see, and sometimes it takes a single outside example to show you another way.
Men and women don't process information the same way, and pretending otherwise is what creates most communication breakdowns. Allowing space, taking things in small chunks, and saying "let me think about that" are not signs of weakness — they're how you stop reacting and start responding.
Retirement without intention is just drift. Most high-achieving men have never asked themselves who they are without the title. Chapter X isn't about winding down; it's about solving for what comes next before the career disappears and leaves a vacuum behind it.
Your eulogy is your roadmap. What you want your spouse, your kids, your grandchildren to say about you at the end is the truest picture of what you actually value. The gap between that and how you spent last Tuesday is worth sitting with.
Links & Resources
The Dad Edge Alliance (June promo — signed book + bonus courses) — https://thedadedge.com/join
Episode show notes and links — https://thedadedge.com/1494
Kid Questions resource — https://thedadedge.com/kidquestions
Michael Kay's website, blog, and podcast — https://michaelfkay.com/
Contact Michael directly — mk@michaelfk.com
How to Craft Your Chapter X — available on Amazon, Barnes & Noble, and at michaelfk.com
Closing
Michael Kay has been figuring out what matters most for a long time, and everything he shared in this conversation — from a demanding father who had no model of his own, to a butcher named Al who showed him what a loving man actually looks like — points to the same truth: the way we show up is almost always about where we came from, until we decide it isn't. If this episode hit close to home, send it to a man in your life who's chasing the next thing without knowing why. Rate and review the show so more dads find these conversations, and follow along so you don't miss what's coming next. Go out and live legendary.

I'll be honest with you — this conversation gave me chills more than once. JoJo Simmons grew up with one of the most recognizable names in music history, the son of Joseph "Run" Simmons, co-founder of Run-D.M.C. and a pioneer of hip hop culture. But what I've always respected about JoJo is that he's never coasted on that name. He's spent years carving out his own path in music, entertainment, and now podcasting, while quietly doing the harder work of becoming a present father and a committed husband.
We went everywhere in this conversation. We talked about what it was like growing up under a microscope, making the kinds of mistakes every teenager makes except having them show up on TMZ. We talked about his parents, how they kept love intact through divorce, how his mother made one of the hardest decisions a parent can make to protect her son, and how his dad evolved from tough love to open communication in a way that shaped the father JoJo is today. This episode is filled with wisdom I didn't expect and moments that made me stop and think about my own home.
JoJo has been married to his wife Denise for nearly seven years, together for 17. They're raising a ten-year-old daughter named Mia and a four-year-old son, Joseph, who is nonverbal and receiving occupational therapy. Watching JoJo talk about both of his kids, the way he's learning to hold space for his daughter as she grows into her own person, and the way he's modeling confidence and calm for his son, you can see a man who is fully in it. Not perfect. Fully in it.
He's also building something. His podcast and media community, For Good, launched just a year ago and it's already growing fast. The name says everything: it represents forever, and it represents putting good into the world. JoJo's vision for it goes beyond episodes and downloads. He wants festivals. He wants a movement. He wants people from every walk of life sitting in a room together feeling heard and seen. After spending an hour with him, I believe he'll build it.
 
Timeline Summary
[1:02] Growing up as the son of Run from Run-D.M.C. — the good and the hard of a very public childhood
[3:47] How JoJo's parents stayed committed to their kids' wellbeing despite divorce, and why he never felt an absence of love
[5:07] The arrest that showed up in the New York Times and TMZ, and the moment JoJo knew he had gone too far
[10:24] What his dad did specifically that shaped the father JoJo wants to be, including the shift from discipline to conversation
[14:28] Dad Edge June offer — signed copy of The Pursuit of Legendary Fatherhood, the Patience course, and more at thedadedge.com/join
[17:28] JoJo's mom: a single mother with a doctorate who ground every day, never spoke ill of his father, and made the hard call to send JoJo to live with his dad at 13
[22:23] How JoJo met Denise at McDonald's — two vegetarians, one bold move, and a phone call to her mother
[28:38] Ten years of dating, a breakup, a promise ring, and why the time apart made the relationship real
[32:21] How communication and being willing to ask "are we really this bad?" has kept their marriage intact through seven years
[36:56] Raising a ten-year-old daughter — learning to listen instead of lead, and why how you treat her now shapes who she'll accept later
[40:44] JoJo's morning routine: up at 5:30 a.m., candle lit, meditation music, 20–30 minutes of emotional regulation before the household wakes up
[44:54] Raising his four-year-old son Joseph — teaching both kids that they are the value in every room they walk into
[46:30] How JoJo thinks about raising kids in the public eye, protecting them from attaching their worth to fame
[49:39] How the For Good podcast started, what the name means, and the community and movement JoJo is building
[57:38] A ten-year dinner table visualization — what JoJo wants his wife and kids to say when they look back
 
Five Key Takeaways
Growing up in the spotlight teaches you fast that public mistakes carry a different weight — JoJo's arrest at a pivotal teenage moment became front-page news, and he now uses that experience to stay honest with his own kids about consequence and accountability without shame.

The way your parents handle their relationship with each other after a split shapes your children more than you realize — JoJo's parents never let him see the turmoil between them, and that protection of the family unit became one of the greatest gifts they gave him.

Marriage takes courage from both people — brushing arguments under the rug feels like peace in the short term but builds into the bigger blowups, and JoJo has learned to address issues in the moment rather than let them accumulate.

As a father of a daughter, your emotional regulation sets the template for what she will tolerate and accept in her own relationships — staying calm, listening deeply, and being the safe place she can come to at 2 a.m. at age 20 is the whole job.

You are the thermostat in your home, not the thermometer — JoJo wakes up at 5:30 every morning before the household starts because he knows the energy he brings into the day is the energy the whole family will operate in.

 
Links & Resources
Join the Dad Edge Alliance (June offer — signed book, Patience course, marriage course, and more) — https://www.thedadedge.com/join
Kid Questions resource — https://www.thedadedge.com/kidquestions
Full show notes for this episode — https://www.thedadedge.com/1493
For Good Podcast website — https://www.forgooduniverse.com
JoJo Simmons on Instagram — https://www.instagram.com/jojo_simmons
For Good Podcast on Instagram — https://www.instagram.com/forgoodpodcast
For Good Podcast on YouTube — https://www.youtube.com/@ForGoodPodcast
 
Closing
JoJo came into this conversation humble, honest, and more self-aware than I expected from someone who's been in the public eye since he was a teenager. That moment where he talked about looking back ten years from now at the dinner table — not asking for perfection, just asking that every person around that table felt seen, heard, and not forced into anything — that hit me. That's the goal. That's the whole thing. If this episode spoke to something you're working through in your own home, share it with another dad who needs to hear it. And if you haven't already, please follow The Dad Edge, leave a rating, and drop a review. Go out and live legendary.

Jenna Free is a counselor specializing in ADHD regulation who discovered her own diagnosis while drowning in grad school with two babies 17 months apart. She has since developed a full certification program teaching other mental health professionals her ADHD regulation method, and she runs ADHD regulation groups for clients from her home base in Calgary, Alberta.
In this episode, Jenna joined The Dad Edge Alliance for a live Q&A that goes far deeper than a typical ADHD conversation. The focus isn't the diagnosis itself — it's the nervous system, specifically how chronic fight-or-flight mode silently drives the impatience, compulsive behavior, crashes, and parenting struggles so many dads in this community experience. If you've ever wondered why you can't just logic your way into being calmer, this one's for you.
Most of us assume ADHD is about the brain you were born with. Jenna reframes it completely — the real problem isn't the diagnosis, it's the dysregulated nervous system underneath it, and that part is something you can actually change. This conversation pulls back the curtain on the frantic-crash cycle, the fight-flight-freeze-fawn response, why pressure feels like performance, and what it looks like to function from a regulated baseline instead of white-knuckling through the day.
This is especially powerful for any dad who has ever snapped at his kids in the morning, struggled to slow down, or quietly wondered whether go, go, go is actually working against him.
 
Timeline Summary
[1:02] Jenna's background: how her own ADHD diagnosis in grad school — with a six-month-old and an 18-month-old at home — led her to develop the ADHD regulation method
[3:24] Why calendars and timers weren't enough: the frantic-crash cycle Jenna kept seeing in herself and every client she worked with
[4:13] The nervous system root cause: why almost every neurodivergent person (and most parents) is running in a chronic state of fight-or-flight
[6:36] Can you think your way out of it? Jenna explains why logic alone can't calm a dysregulated nervous system
[9:16] Alliance member Jason's question: where to start with regulation for yourself and how to notice when your son is sliding into dysregulation
[10:06] The first practical step — learning to physically feel dysregulation in your body: tight shoulders, rushing, impatience, holding your breath
[11:49] The rushing reframe every parent needs: shifting from "let's go, let's go" to "let's focus" and why that small shift changes the whole morning
[17:55] Breaking down all four modes: fight, flight, freeze, and fawn — including why people-pleasing is a survival response, not a personality trait
[25:26] Alliance member Chris's question: the "pressure to perform" cycle and why functioning in high-intensity fight-or-flight leads to hard crashes and compulsive avoidance
[30:21] Why a formal diagnosis may not matter: Jenna's framework focuses on nervous system regulation regardless of whether you have a label
[40:19] Dysregulation is contagious — but so is regulation: how Jenna's own internal work changed her husband without a single conversation about it
[42:16] Joanne's question: how to help a high-achieving son who struggles at school, and why the most powerful thing parents can do happens before they drop the kids off
[47:21] Jenna's upcoming book, Full Capacity, and why she believes regulation is the most ambitious thing a driven person can pursue
[54:12] The dreamer-freeze type: why a low-motivation, avoidant kid is just as dysregulated as a hyperactive one — it just looks different
[57:10] The host shares his own ADHD management tools — exercise and clean eating — and Jenna explains exactly why they work from a nervous system standpoint
 
Five Key Takeaways
You can't think your way out of fight-or-flight because it's not a thought problem — it's a nervous system problem. The primal part of your brain believes you're being chased by a bear, and no amount of self-talk will convince it otherwise until you address the physical and behavioral patterns keeping it on alert.

The frantic-crash cycle isn't a productivity style — it's a symptom. When you require pressure to get things done and then collapse afterward, you're not built that way; you've been trained into it. The only way out is to consciously lower the intensity during the good stretches, not just manage the crashes.

Rushing is one of the clearest signals your nervous system has flipped into survival mode. When you catch yourself rushing the kids in the morning, the fix isn't to push through faster — it's to physically slow down and shift from "let's go" to "let's focus," which calms everyone's system and actually gets you out the door more effectively.

Your regulation — or lack of it — is setting the baseline for your whole family. Kids and partners co-regulate with the people around them. You can't force your kids to be calm, but becoming a regulated, grounded presence does more than any conversation about breathing ever will.

Fight-or-flight doesn't always look like intensity. Freeze and avoidance are just as much a dysregulated state as frantic rushing — they're just the other end of the pendulum. A kid who looks unmotivated or a dad who procrastinates for two weeks is dealing with the same nervous system problem as the guy who can't slow down.

Links & Resources
The Dad Edge Alliance — https://thedadedge.com/join
Questions for the Car (free resource) — https://thedadedge.com/kidquestions
ADHD with Jenna Free (social media) — @adhdwithjennafree
Full Capacity HQ (upcoming content on regulation for ambitious people) — @fullcapacityhq
Episode Shownotes: http://thedadedge.com/1492
Closing
What Jenna laid out here isn't a quick fix — and she'd be the first one to tell you that. But there's something powerful in knowing that the part of you that snaps at your kids, crashes after a big push, or can't quite slow down no matter how much you want to — that part isn't a character flaw. It's a nervous system that's been running in survival mode, and it can be retrained. If this conversation hit close to home, share it with a dad you know who's quietly fighting the same battle. And if you're not yet part of the Alliance where conversations like this happen every month, head over to thedadedge.com/join. Follow the show, leave a rating and review, and help us get this in front of the dads who need it most.
Go out and live legendary.

Jamie Kozub and Chris Carter are the yin and yang behind Shit My Dad Taught Me, a podcast that's exploded to over 2.5 million views every month in barely 18 months. Together they also co-founded Burlington Dads, a community of 7,200 fathers that has raised over $1 million for local families and charities. But what makes these two men worth an hour of your time isn't the numbers. It's the two completely different roads that brought them here.
Jamie has never met his biological father and grew up 40 minutes outside Thunder Bay in a house with no working toilet and a potbelly stove for heat. With his dad working construction hundreds of miles away Monday through Saturday, Jamie was cooking dinner and raising his little brother at 12. He moved out at 15, worked the Sony store from two till ten every day through high school, and was making $130K a year by 18. Then at 19, after blowing $60,000 at the casino, he walked back in, handed over his driver's license, and banned himself from every casino in Ontario.
Chris had the opposite upbringing: a ten-out-of-ten dad who fed every kid who walked through the door and modeled what it means to raise daughters. Now a girl dad of two, Chris shares his number one piece of advice, just take them with you, and the story of the letter that confronted him at 340 pounds. A year later, he's lost nearly 100 pounds and is preparing for his first bodybuilding show at 42.
We also go to some deep waters in this one: their friend Matt's story of losing his father and grandfather to suicide, and my own 33 days of insomnia in 2017 and the counselor's words that changed my perception forever. This is a conversation about fatherhood, brotherhood, and building the communities that keep men alive and thriving. Don't miss it.
 
Timeline Summary
[1:02] Larry welcomes Jamie Kozub and Chris Carter, the yin and yang behind Shit My Dad Taught Me
[1:56] Jamie on never meeting his biological father and why he feels no void to fill
[2:58] Growing up outside Thunder Bay with no working toilet, a potbelly stove, and a dad gone Monday to Saturday
[10:33] Chris's number one girl dad advice: just take them with you, from boardrooms to private jets
[17:56] Moving out at 15, couch surfing, and working the Sony store from two till ten every day
[19:39] Making $130K at 18 and turning down a University of Miami scholarship
[20:28] Walking into the casino at 19 to ban himself from every casino in Ontario for five years
[26:35] Chris's dad and the barbecue pizza rule: everyone who walks through the door gets fed
[33:02] How Shit My Dad Taught Me reached 2.5 million monthly views through radical authenticity
[37:16] The Lexie J letter story that confronted Chris at 340 pounds and sparked his transformation
[42:18] Their friend Matt's story of loss and his commitment to breaking a generational cycle
[45:18] Larry opens up about 33 days of insomnia and the counselor's words that changed everything
[48:14] Pits and peaks: Chris's daily traditions for getting his girls to open up
[51:46] A warrior on a farm: why the biggest guy in the room works hardest at being gentle
[54:30] Jamie on raising boys who respect women, learn from losing, and greet every guest at the door
[56:47] Inside Burlington Dads: 14 events, a $75K golf tournament, and a $77K Christmas toy drive
 
Five Key Takeaways
You don't need a void filled to move forward; Jamie chose to honor the dad who raised him while letting go of the one who didn't, and turned a hard childhood into fuel instead of an excuse.

The simplest girl dad advice is also the best: take your kids with you everywhere so they never believe a glass ceiling exists.

Make your home the place where every kid is fed, welcomed, and safe, because you'd rather your kids make their choices under your roof than somewhere else.

Find the thing that confronts you before your family has to write you the letter; Chris lost nearly 100 pounds because he refused to put his daughters in that position.

Whatever pain you're carrying, you don't have to carry it alone; real communities of men exist, and guys like Jamie and Chris will always pick up the phone.

 
Links & Resources
Shit My Dad Taught Me — available on all platforms, including Spotify and YouTube
Follow Chris on Instagram — @chriscarterbd
Follow Jamie on Instagram — @jamiekozub
Burlington Dads on Facebook
Episode resources — https://thedadedge.com/1491
Join the Dad Edge Alliance — https://thedadedge.com/join
Questions for the Car free download — https://thedadedge.com/kidquestions
Closing
There's a moment in this episode where a 19-year-old kid making six figures walks into a casino, hands over his driver's license, and bans himself for five years because he knew the life he wanted required a different man. That's what taking responsibility actually looks like, and it's the thread running through this entire conversation, from Chris's 100-pound transformation to two men building a community of 7,200 dads who refuse to do life alone. If this one hit home, send it to the brother in your life who needs to hear that good men come together. Go out and live legendary.

Jess Hilarious has built a career on telling the truth in a way that makes people laugh and feel seen, from the Baltimore open mic scene to Wild 'N Out, starring on Rel, her hit podcast Carefully Reckless, and now co-hosting The Breakfast Club. But in this conversation, we go somewhere most people have never heard her go: what it really took to become the mother and co-parent she is today.
Jess got pregnant at 19, raised in a strict church household, terrified to tell her parents she even had a boyfriend. She opens up about the first six months after her son Ashton was born, when she didn't want to be a mom at all, and the breakdown on her knees in her mother's house that ended with her baby smirking up at her from the crib. That was the moment everything changed.
We also walk through the hard road with her son's father, Jerome. The cheating, the other girl at Ashton's first birthday party, and the public comment that revealed he had a second child on the way. Instead of staying at war, Jess chose to understand the trauma behind his behavior, and the two of them took actual co-parenting vows: for better or for worse, till death do we parent.
As a father of four boys, I know how many men in our community are navigating co-parenting right now, and this episode is packed with hard-won wisdom on boundaries, accountability, and putting your kids first. Jess's new book, Til Death Do We Parent, brings her trademark humor and honesty to all of it, and this conversation is the perfect introduction.
 
Timeline Summary
[1:01] Larry welcomes comedian, actress, and Breakfast Club co-host Jess Hilarious to the show
[1:48] Jess opens up about not wanting to be a mom for the first six months after her son was born
[3:15] Telling Jerome she was pregnant at 19 and his unexpectedly joyful reaction
[4:25] A charge on her record, no job offers, and moving back in with her mom after Ashton arrived
[4:52] The breakdown in her mom's house: "why would you pick me to be your mother?"
[7:17] Telling her parents at 8 PM: her dad's ten-second breathing technique and her mom's prayer
[15:02] The funeral story at age eight that proved Jess was born funny
[17:43] Martin Lawrence's brother calls and Jess fakes ten years of stand-up experience
[18:41] Opening for Martin Lawrence in front of 13,000 people in Baltimore after five open mics
[25:05] Rome brings another girl to Ashton's first birthday party
[26:57] Leaving a good man for one more chance, then learning about Rome's second child from a public comment
[31:14] Understanding Rome's trauma: losing his mother at ten and finding her himself
[33:32] The co-parenting vows: "I take you, Jerome James, to be my lawfully wedded co-parent"
[35:22] Dating selfishly and taking accountability for the men she brought around Ashton
[38:15] The 1 AM phone call that made her husband draw the line on boundaries
[42:58] Larry shares meeting his biological father by chance in a St. Louis Starbucks at age 30
 
Five Key Takeaways
Treat co-parenting like a vow you can't walk away from, because your child is watching how you show up for better or for worse.
Your kids absorb every ounce of tension between you and your ex, and defiance at school is often a reflection of the energy they're consuming at home.
Understanding the trauma behind your ex's behavior won't excuse it, but it can free you from resentment and make a real friendship possible.
When you have kids, you date as a package, so anyone who isn't building a bond with your child isn't actually good for you either.
Boundaries protect every relationship you have, and putting "friendship hours" around your co-parent isn't disrespect, it's what keeps your marriage and your co-parenting healthy.
 
Links & Resources
Til Death Do We Parent by Jess Hilarious: https://www.amazon.com/Til-Death-Do-We-Parent/dp/1668059355
Jess's website — https://jesshilariousofficial.com
Follow Jess on Instagram — @jesshilarious_official
Follow Jess on Twitter and Snapchat — @jess_hilarious
Jess Hilarious Official on Facebook
Episode resources — https://thedadedge.com/1490
Questions for the Car free download — https://thedadedge.com/questions
The Dad Edge Alliance — http://thedadedge.com/join
 
Closing
There's a moment in this episode where Jess describes falling to her knees, asking her infant son why he chose her as his mother, and looking up to see him smirking at her from the crib as if to say "I'm here, so put on your big girl panties." That's the kind of raw honesty that changes how you see your own parenting story. If you're navigating co-parenting, boundaries, or just the weight of feeling unready, share this one with a brother who needs it. Go out and live legendary.