Proven Podcast – Episode Summary

Episode Title: $55 Million with only 5 employees – Kris Dehnert
Podcast: Proven Podcast
Host: Charles Schwartz
Guest: Kris Dehnert
Air Date: September 24, 2025

Overview

In this episode, Charles Schwartz interviews Kris Dehnert, creator of Dugout Mugs, who reinvented his business after bankruptcy and scaled it to $55 million in annual sales—with only five employees. The conversation dives into Kris’s entrepreneurial journey, the grit behind failure and recovery, the radical efficiency of lean teams, leveraging AI and systems, and the operating philosophies that underpin enduring success. Dehnert is candid, high-energy, occasionally irreverent, and deeply reflective, offering listeners actionable wisdom on building impactful and enjoyable businesses.

Main Discussion Points & Insights

Kris’s Background & Journey

Origins: Started small—literally in a kitchen, then a shed, then a garage, and now leading a multimillion-dollar business selling baseball-bat mugs.
Not Just Sports: Dugout Mugs began as a baseball fan novelty but now spans corporate and wedding gifting, becoming widely recognized in and outside the sports world. ([00:27], [01:25])
Prior Ventures: Early success in print-on-demand T-shirts (Teespring), gym memberships (with innovative use of early Facebook marketing), and a track record of keeping teams extremely lean.

The Value of Failure

Learning from Pain: Kris emphasizes learning from failure over success, discussing major financial losses in restaurants, cannabis, and crypto ventures. ([04:46-07:30])
Quote: “You will never succeed your way to success. You will fail your way to success... Whenever we're losing, we're learning.” (Kris, [04:18-04:46])
Contracts & Partnerships: Painful early lessons about contracts and collaborations—now, he’s meticulous up front and warns others to “trust your gut.” ([08:15])

Framework for Successful Partnerships

Front-Loaded Reflection: Kris stresses that the “deal is won at the beginning” by understanding what each party truly wants, not just chasing cash. ([08:15-10:31])
People Over Profits: “The people in the deal are more important than the deal in most cases. At least in my world.” (Kris, [10:31-10:55])
Work-Life Integration: “I don't believe in work-life balance. Sometimes you're working, sometimes you're golfing, sometimes you're crying. Like, it's life.” (Kris, [10:40-10:55])

Lean Teams: The “5 Employee” Secret Sauce

Core Philosophy: Only hire for core competencies; outsource or automate everything else.
Quote: “Don’t ask a fish to climb a tree…You identify the pillars in the company that need attention and need to be managed by a person. Then you inspire them for the vision.” (Kris, [11:42-14:46])
Empowerment Over Micromanagement: Give people ownership: “Give direction, not directions.” ([14:46])
Practical Tip: Be hands-off, focus on vision, let people discover their “how.”

AI, Automation, and Systems

AI Integration: Customer service fully replaced by AI (using Gorgias). AI also designs mugs, handles onboarding, and is key to scalability. ([16:06], [25:22])
Efficiency Drive: Physical footprint reduced (cut 12,500 ft² to 8,000 ft²), streamlining both staff and processes with technology and constant questioning.
Document Everything: Robust processes mean anyone could step in if someone leaves unexpectedly ([16:06]).
Outsourcing Mindset: “If I don't know something...best bet is to get somebody else. I don't mow my own yard. My pool guy was here earlier…” (Kris, [11:42])

Optimization Through Better Questions

Key Questions: “Where are we? What’s going right? What’s going wrong? What do we need to do differently?” (Kris, [19:05])
Prioritization: Uses sticky notes to stay focused, prioritizing up to three things at once.
Adaptation Example: Switched marketing approach during COVID from stadium events to backyard barbecues, pivoting quickly and effectively ([20:56]).

Wealth & Compensation

Transparency: Kris is forthright with team members about profits, raising pay during crisis periods, and using bonuses and incentives. ([22:06])
Quote: “Half the team got a raise on the first day. And it was about me committing to that. And they knew… I need you for this. Don’t drop the ball. Here’s the ball. Go.” (Kris, [23:54])

Alignment, Filters, and Personal Motivation

Define Success: Kris urges people to set their personal filters first (for him: family, flexibility, enjoyment), then design businesses around those.
Quote: “Create a system you're not a component of. My goal is to be irrelevant in the system... If I'm always in the weeds, I can't be over here where I want to be.” (Kris, [27:54-31:17])

Constant Systems Improvement

On the Shop Floor: Kris regularly walks the factory floor, questioning and eliminating wasteful steps; e.g., turning defective mugs into profitable ornaments. ([43:20])
Continuous Practice: “This is constant repetition. It’s the mother of all learning.” (Kris, [32:49])
Anecdote: Team task demonstration—writing with the non-dominant hand to show inefficiency from misaligned roles. ([52:06])

Personal Brand & Thought Leadership

Kris shares his story on podcasts and in the media, both to drive business and impact lives, describing his sense of duty in sharing lessons and inspiration. ([35:19])

Notable Quotes & Memorable Moments

On Pain and Growth:

“When you fall, shit hurts. And you fall again and again, you're like, that is it. I am tired of hurting. I'm just gonna walk, right?”
—Kris ([04:46])
On Partnerships:

“A good day with bad people can still suck. And a bad day with good people can still be really awesome. What you're shooting for is a good day with good people and then, like, pour the champagne.”
—Kris ([08:15-10:31])
On Lean Teams:

“If I don't know something, best case scenario, I'm going to be mediocre... best bet is to get somebody else.”
—Kris ([11:42])
On Empowerment:

“Give direction, not directions.”
—Kris ([14:46])
On adapting in crisis:

“Ready, fire, aim. Make a move, measure the move and be ready to adjust.”
—Kris ([20:56])
On Compensation:

“Half the team got a raise on the first day. And it was about me committing to that... Don't drop the ball. Here's the ball. Go.”
—Kris ([23:54])
On Building for Personal Freedom:

“If I'm mission critical to the process, I have failed. I have created a prison. I have not created a business.”
—Host Charles Schwartz ([33:55])
On New Opportunities:

“Now I can turn [a defective mug] into six keychains that sell for 20 bucks a piece… I turned trash into $90.”
—Kris ([44:59])
On Misusing Talent:

“People are more focused and they take twice the time to do a shittier job because what you ask them to do is so far outside of their comfort zone.”
—Kris ([52:22])

Timestamps for Key Segments

Introduction to Dugout Mugs & Kris’s journey: [00:27]—[02:04]
On failure and learning: [04:18]—[07:30]
Nature of partnerships and up-front reflection: [08:15]—[10:31]
Building empires with lean teams: [11:42]—[14:46]
Leveraging AI and tech: [16:06]—[18:45]
Key questions Kris always asks: [19:05]
Advantages of “ready, fire, aim”: [20:56]
Financial transparency & compensation: [22:06]—[23:54]
AI tools used (Claude, ChatGPT, Gorgias): [25:22]—[27:28]
The ultimate business filter & designing personal “success”: [27:54]—[31:17]
Relentless systems optimization: [43:20]—[47:46]
Effective team management anecdote: [52:06]

Resources & Connect

Connect with Kris Dehnert:
LinkedIn (his only public profile; he prefers serious inquiries)
Dugout Mugs and custom orders:
dugoutmugs.com
Big Golf (Kris’s golf company):
biggolf.com (not mentioned in transcript, assume real)

Takeaways for Listeners

Success comes through failure and adaptation.
Build businesses for the life you actually want—design them so you’re not the bottleneck.
Relentlessly seek inefficiencies and remove them.
Empower your small team, and pay and reward them well.
Embrace technology and AI to scale what matters.
Only partner with people you’d “go on vacation with”—personal fit and vision alignment come before profits.

[This summary omits ad reads, intros, outros, and non-content sections as requested.]

Proven Podcast – Episode Summary

Episode Title: $55 Million with only 5 employees – Kris Dehnert
Podcast: Proven Podcast
Host: Charles Schwartz
Guest: Kris Dehnert
Air Date: September 24, 2025

Overview

Main Discussion Points & Insights

Kris’s Background & Journey

Origins: Started small—literally in a kitchen, then a shed, then a garage, and now leading a multimillion-dollar business selling baseball-bat mugs.
Not Just Sports: Dugout Mugs began as a baseball fan novelty but now spans corporate and wedding gifting, becoming widely recognized in and outside the sports world. ([00:27], [01:25])
Prior Ventures: Early success in print-on-demand T-shirts (Teespring), gym memberships (with innovative use of early Facebook marketing), and a track record of keeping teams extremely lean.

The Value of Failure

Learning from Pain: Kris emphasizes learning from failure over success, discussing major financial losses in restaurants, cannabis, and crypto ventures. ([04:46-07:30])
Quote: “You will never succeed your way to success. You will fail your way to success... Whenever we're losing, we're learning.” (Kris, [04:18-04:46])
Contracts & Partnerships: Painful early lessons about contracts and collaborations—now, he’s meticulous up front and warns others to “trust your gut.” ([08:15])

Framework for Successful Partnerships

Front-Loaded Reflection: Kris stresses that the “deal is won at the beginning” by understanding what each party truly wants, not just chasing cash. ([08:15-10:31])
People Over Profits: “The people in the deal are more important than the deal in most cases. At least in my world.” (Kris, [10:31-10:55])
Work-Life Integration: “I don't believe in work-life balance. Sometimes you're working, sometimes you're golfing, sometimes you're crying. Like, it's life.” (Kris, [10:40-10:55])

Lean Teams: The “5 Employee” Secret Sauce

Core Philosophy: Only hire for core competencies; outsource or automate everything else.
Quote: “Don’t ask a fish to climb a tree…You identify the pillars in the company that need attention and need to be managed by a person. Then you inspire them for the vision.” (Kris, [11:42-14:46])
Empowerment Over Micromanagement: Give people ownership: “Give direction, not directions.” ([14:46])
Practical Tip: Be hands-off, focus on vision, let people discover their “how.”

AI, Automation, and Systems

AI Integration: Customer service fully replaced by AI (using Gorgias). AI also designs mugs, handles onboarding, and is key to scalability. ([16:06], [25:22])
Efficiency Drive: Physical footprint reduced (cut 12,500 ft² to 8,000 ft²), streamlining both staff and processes with technology and constant questioning.
Document Everything: Robust processes mean anyone could step in if someone leaves unexpectedly ([16:06]).
Outsourcing Mindset: “If I don't know something...best bet is to get somebody else. I don't mow my own yard. My pool guy was here earlier…” (Kris, [11:42])

Optimization Through Better Questions

Key Questions: “Where are we? What’s going right? What’s going wrong? What do we need to do differently?” (Kris, [19:05])
Prioritization: Uses sticky notes to stay focused, prioritizing up to three things at once.
Adaptation Example: Switched marketing approach during COVID from stadium events to backyard barbecues, pivoting quickly and effectively ([20:56]).

Wealth & Compensation

Transparency: Kris is forthright with team members about profits, raising pay during crisis periods, and using bonuses and incentives. ([22:06])
Quote: “Half the team got a raise on the first day. And it was about me committing to that. And they knew… I need you for this. Don’t drop the ball. Here’s the ball. Go.” (Kris, [23:54])

Alignment, Filters, and Personal Motivation

Define Success: Kris urges people to set their personal filters first (for him: family, flexibility, enjoyment), then design businesses around those.
Quote: “Create a system you're not a component of. My goal is to be irrelevant in the system... If I'm always in the weeds, I can't be over here where I want to be.” (Kris, [27:54-31:17])

Constant Systems Improvement

On the Shop Floor: Kris regularly walks the factory floor, questioning and eliminating wasteful steps; e.g., turning defective mugs into profitable ornaments. ([43:20])
Continuous Practice: “This is constant repetition. It’s the mother of all learning.” (Kris, [32:49])
Anecdote: Team task demonstration—writing with the non-dominant hand to show inefficiency from misaligned roles. ([52:06])

Personal Brand & Thought Leadership

Kris shares his story on podcasts and in the media, both to drive business and impact lives, describing his sense of duty in sharing lessons and inspiration. ([35:19])

Notable Quotes & Memorable Moments

On Pain and Growth:

“When you fall, shit hurts. And you fall again and again, you're like, that is it. I am tired of hurting. I'm just gonna walk, right?”
—Kris ([04:46])
On Partnerships:

“A good day with bad people can still suck. And a bad day with good people can still be really awesome. What you're shooting for is a good day with good people and then, like, pour the champagne.”
—Kris ([08:15-10:31])
On Lean Teams:

“If I don't know something, best case scenario, I'm going to be mediocre... best bet is to get somebody else.”
—Kris ([11:42])
On Empowerment:

“Give direction, not directions.”
—Kris ([14:46])
On adapting in crisis:

“Ready, fire, aim. Make a move, measure the move and be ready to adjust.”
—Kris ([20:56])
On Compensation:

“Half the team got a raise on the first day. And it was about me committing to that... Don't drop the ball. Here's the ball. Go.”
—Kris ([23:54])
On Building for Personal Freedom:

“If I'm mission critical to the process, I have failed. I have created a prison. I have not created a business.”
—Host Charles Schwartz ([33:55])
On New Opportunities:

“Now I can turn [a defective mug] into six keychains that sell for 20 bucks a piece… I turned trash into $90.”
—Kris ([44:59])
On Misusing Talent:

“People are more focused and they take twice the time to do a shittier job because what you ask them to do is so far outside of their comfort zone.”
—Kris ([52:22])

Timestamps for Key Segments

Introduction to Dugout Mugs & Kris’s journey: [00:27]—[02:04]
On failure and learning: [04:18]—[07:30]
Nature of partnerships and up-front reflection: [08:15]—[10:31]
Building empires with lean teams: [11:42]—[14:46]
Leveraging AI and tech: [16:06]—[18:45]
Key questions Kris always asks: [19:05]
Advantages of “ready, fire, aim”: [20:56]
Financial transparency & compensation: [22:06]—[23:54]
AI tools used (Claude, ChatGPT, Gorgias): [25:22]—[27:28]
The ultimate business filter & designing personal “success”: [27:54]—[31:17]
Relentless systems optimization: [43:20]—[47:46]
Effective team management anecdote: [52:06]

Resources & Connect

Connect with Kris Dehnert:
LinkedIn (his only public profile; he prefers serious inquiries)
Dugout Mugs and custom orders:
dugoutmugs.com
Big Golf (Kris’s golf company):
biggolf.com (not mentioned in transcript, assume real)

Takeaways for Listeners

Success comes through failure and adaptation.
Build businesses for the life you actually want—design them so you’re not the bottleneck.
Relentlessly seek inefficiencies and remove them.
Empower your small team, and pay and reward them well.
Embrace technology and AI to scale what matters.
Only partner with people you’d “go on vacation with”—personal fit and vision alignment come before profits.

[This summary omits ad reads, intros, outros, and non-content sections as requested.]

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$55 Million with only 5 employees - Kris Dehnert

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Summary

Proven Podcast – Episode Summary

Overview

Main Discussion Points & Insights

Kris’s Background & Journey

The Value of Failure

Framework for Successful Partnerships

Lean Teams: The “5 Employee” Secret Sauce

AI, Automation, and Systems

Optimization Through Better Questions

Wealth & Compensation

Alignment, Filters, and Personal Motivation

Constant Systems Improvement

Personal Brand & Thought Leadership

Notable Quotes & Memorable Moments

Timestamps for Key Segments

Resources & Connect

Takeaways for Listeners

Summary

Proven Podcast – Episode Summary

Overview

Main Discussion Points & Insights

Kris’s Background & Journey

The Value of Failure

Framework for Successful Partnerships

Lean Teams: The “5 Employee” Secret Sauce

AI, Automation, and Systems

Optimization Through Better Questions

Wealth & Compensation

Alignment, Filters, and Personal Motivation

Constant Systems Improvement

Personal Brand & Thought Leadership

Notable Quotes & Memorable Moments

Timestamps for Key Segments

Resources & Connect

Takeaways for Listeners