What if the worst thing that ever happened to you ended up building the best parts of your life?
At 21 years old, Chris Kiefer lost his father to pancreatic cancer.
It could have broken him.
Instead, it forced him to confront something most people don’t confront until much later in life:
You do not have unlimited time.
That loss changed the career Chris chose, the woman he married, the brother he became, the father he wanted to be, the businesses he built, and ultimately the man he became.
And Chris says something in this episode that may stop you in your tracks:
He’s reached a point where he can actually be grateful for what happened.
Not because losing his father wasn’t devastating.
But because of the fruit that grew from the pain.
This episode is about what happens when adversity doesn’t just hurt you—it reorders your entire life.
In this episode of Built for the Cold, Joe sits down with entrepreneur, father of five, and founder of Boolean Automation, Chris Kiefer, for a conversation about loss, fatherhood, faith, technology, entrepreneurship, and what actually matters when life strips away the illusion that you have unlimited time.
Chris was only 21 when his father was diagnosed with pancreatic cancer and passed away.
Before that moment, Chris was headed toward what looked like a successful and predictable future in aerospace engineering. He interned at Lockheed Martin, performed well, and had a job waiting for him after graduation.
Then his perspective changed.
Instead of moving across the country and chasing the career he thought he wanted, Chris returned home, became deeply involved in his younger brother’s life, eventually walked away from engineering, became an entrepreneur, married young, and began building an entirely different life.
Chris explains why one question transformed the way he processed his father's death:
“What is the worst thing that ever happened to you—and how was it also the best thing that ever happened to you?”
The conversation goes deep into the small moments that define fatherhood—the five-minute phone calls, showing up to games nobody else cares about, celebrating insignificant victories that are significant because your child cares about them—and why Chris now measures fatherhood by whether his children will someday want to call him with those same little wins.
Joe and Chris also examine the battle modern entrepreneurs face between ambition and presence, especially as technology, business, social media, and AI constantly demand more attention.
From there, the conversation turns toward AI and the future.
Rather than approaching technology purely from fear, Chris explains why he chooses “Team Optimism,” how he uses AI creatively with his children, why technological efficiency tends to create more—not less—opportunity, and why he believes entrepreneurs with a strong moral compass need to actively participate in the next technological revolution.
Chris also breaks down how he built Boolean Automation, an extremely specialized company helping large painting contractors automate their businesses, and why the internet and AI are creating opportunities for entrepreneurs to solve problems at a level of specificity that previously would have been impossible.
Ultimately, this episode isn't just about grief, AI, entrepreneurship, or parenting.
It's about deciding what adversity is going to produce in you.
You don't get to rewrite what happened.
But you do get to decide what you build from it.
KEY HIGHLIGHTS
- Losing his father at 21: How pancreatic cancer and the death of Chris's father radically changed his trajectory.
- The question that reframed tragedy:
“What is the worst thing that's ever happened to you—and how was it also the best thing that's ever happened to you?” - Pain can reorder your priorities: Why Chris walked away from the expected Lockheed Martin engineering path and returned home.
- Adversity accelerated maturity: Chris believes losing his father forced him to develop perspective he otherwise may not have gained for another decade.
- Presence over prestige: Chris once felt embarrassed that his father was “just” a PE teacher. As an adult, he realized his father's presence mattered infinitely more than an impressive title.
- The moments your kids remember: Why a five-minute phone call after basketball practice can matter more than accomplishments, money, or status.
- The left-handed layup: Chris shares the emotional story of winning a meaningless recreational basketball game—and realizing the only person he desperately wanted to call was his dad.
- A different definition of fatherhood: Success isn't simply providing for your children. It's becoming the person they still want to call when something small goes right.
- Ambition versus presence: The internal battle entrepreneurs face when their mind is constantly trying to consume, learn, build, and stay ahead.
- Breaking the technology addiction: Chris discusses removing social media from his phone during Lent and realizing just how automatic the habit had become.
- Raising kids in an AI world: Instead of immediately fearing AI, Chris is experimenting with ways to use it to create, teach, connect, and reinforce positive messages with his children.
- “Team Optimism”: Why Chris would rather believe technology can be used for good and be wrong than spend his life expecting the worst.
- AI as an amplifier: Technology itself isn't necessarily the problem—the character and intention of the person wielding it matter.
- Why cheaper creation creates more creation: Chris explains why dramatically reducing the cost of software, music, automation, and content may increase human experimentation rather than eliminate it.
- Faith in the age of AI: Why technological advancement doesn't change Chris's belief that humanity remains extraordinarily small compared with God and creation.
- His bigger mission: Chris wants to help 1,000 Christians start or acquire businesses during his lifetime.
- The power of extreme specialization: How Boolean Automation built an entire business around automating systems specifically for painting companies.
- The opportunity of the internet: Hyper-specific expertise that once couldn't support a company can now attract precisely the right customers from around the world.
- The central Built for the Cold lesson:
You cannot control every adversity that enters your life. You can control what you allow that adversity to build.
Connect with Chris
The Pursuit of Purpose Podcast: https://podcasts.apple.com/us/podcast/the-pursuit-of-purpose/id1337457439
https://helloboolean.com/
Connect with Joe
Instagram: https://www.instagram.com/joewannerofficial/
LinkedIn: https://www.linkedin.com/in/joe-wanner-19632bab/
Website: https://www.thejoewanner.com
Make a Cold connection with exercise physiologist, sales coach, and much more @JoeWannerOfficial on Instagram