What do nuclear submarines and boardrooms have in common? High-stakes decision-making, leadership under pressure, and conversations that matter more than commands.

This week, I sit down with Matt DiGeronimo, former submarine officer turned leadership strategist, author, and speaker. We talk about:

• Why “mental judo” beats mental warfare
• How to influence without triggering resistance
• The hidden dangers of binary thinking
• Why nuance, clarity, and intellectual humility are the new superpowers in leadership

If you’ve ever wanted to improve how you lead, listen, and communicate, this episode is a must-watch.

Matt's Books:
https://www.amazon.com/stores/Matt-DiGeronimo/author/B08YWZ6CYZ?ref=dbs_a_def_rwt_sims_vu00_r2_c1&isDramIntegrated=true&shoppingPortalEnabled=true&ccs_id=53333962-f2e7-4add-b921-b260487e6ca3

Matt's Website:
https://medium.com/ ⁨@mjdigeronimo⁩  
https://substack.com/@mattdigeronimo 

Matt's YouTube Channel:
https://www.youtube.com/@mjdigeronimo/videos 

In this episode, I’m joined by Bennett Maxwell, founder of Dirty Dough—the cookie company that’s not only disrupting the dessert space, but also taking on billion-dollar competitors in the process. What started as a side hustle quickly turned into a national brand—and a legal battle with industry giant Crumbl.

But Bennett’s story isn’t just about cookies or courtrooms. It’s about resilience, purpose, and the deeper meaning behind entrepreneurship. From building a wildly successful franchise system to launching his own podcast, Deeper Than Dough, Bennett’s journey is packed with lessons in grit, growth, and going against the grain.

If you've ever felt reluctant to take the leap—or wondered how far your values can take you in business—this conversation is one you won’t want to miss.

Dirty Dough
https://dirtydoughcookies.com

Today, I’m excited to introduce a guest who lives at the intersection of technology and entrepreneurship, Bill Boulden.

Bill is a Fractional CTO who specializes in taking ideas from concept to finished product, helping non-technical founders and CEOs navigate the complex world of software development. 

Through services like Power Hours where he claims can save thousands of dollars and multiple headaches, VIP Days to solve big developer blockers, and full-scale Fractional CTO engagements, Bill guides startups to launch their MVPs efficiently and effectively. His expertise spans AWS architecture, React, Serverless, Node.js, DevOps, and more—offering a rare combination of technical brilliance and development acumen.

Bill’s clients rave about his ability to distill complex technical strategies into actionable insights, ensuring that projects not only meet deadlines but exceed expectations. Whether it’s scaling a startup or helping founders avoid costly pitfalls, Bill’s impact is undeniable.

In this episode, we’ll dive into Bill’s journey, uncover what it takes to turn tech ideas into reality, and explore the lessons he’s learned along the way. 
If you’re a founder wondering how to bring your tech vision to life, this is an episode you won’t want to miss!

Bill's Contact Information:
https://www.billboulden.com 
[email protected]

More information on The Reluctant Entrepreneur Podcast is available here:
https://www.mikekonrad.com/podcast 

Chapters:
00:00:00 Introducing Bill Balden: The Fractional CTO Revolution  
00:03:33 Why Coding Should be Taught in Schools  
00:05:40 Journey from Programmer to CTO  
00:08:39 Understanding the MVP Concept
00:11:32 Balancing Tech Skills and Market Insight
00:14:37 The Universal Language of Music  
00:17:49 Transformative Marketing Strategies: From Traditional Ads to Conscious Marketing
00:20:50 Becoming an Authority-Based Influencer
00:23:47 Navigating Entrepreneurial Feast or Famine  
00:26:48 Navigating Uncertainty in Clean Tech Investments
00:29:36 Importance of Execution in Startup Success
00:32:21 The Rise of Electric Cars and Market Dynamics  
00:35:11 Evolution of the Music Industry  
00:38:12 Cultural Nuances in Business Negotiations  
00:40:54 The Value of Startup Equity: When Shares Become Worthwhile  
00:43:46 The Hype Cycle of Emerging Technologies
00:47:41 Choosing the Right Service for Clients
00:49:40 Balancing Leadership and Technical Tasks  
00:52:36 Calibrating Success from Missed Attempts  
00:55:44 The Fractional Lifestyle: Balancing Startups and Family  
00:58:39 The Significance of Trivial Opinions in Nuclear Science and Coding
01:02:01 Kia's Rebranding Strategy and its Impact  
01:04:05 The Rise of Stellantis in the Automotive Industry
01:06:48 Discover "The Reluctant Entrepreneur" Book and Resources

Today I’m joined by Scott Trumpolt. Scott Trumpolt is the founder of Trumpolt Compensation Design Solutions, a consultancy dedicated to helping organizations attract, motivate, and retain top talent through smart, customized compensation strategies. 

With years of experience in human resources and compensation design, Scott has worked with companies of all sizes—from fast-growing startups to large global enterprises—across a broad range of industries.

Before launching his own firm, Scott served in senior compensation roles at several companies, where he developed a reputation for aligning pay practices with business performance, culture, and long-term strategic goals. 

His expertise spans executive compensation, incentive design, salary benchmarking, pay equity, and total rewards strategy. Scott is known for his pragmatic, data-driven approach and his ability to translate complex compensation issues into clear, actionable solutions. 

He founded Trumpolt Compensation Design Solutions to give companies access to high-quality, customized compensation support without the overhead of a large consulting firm.

Scott’s path to entrepreneurship wasn’t born out of a desire to run a business for business’s sake—but from a deep understanding of a problem that needed solving: how companies design, implement, and manage compensation plans that actually work.

In the first half of our conversation, Scott opens up about his journey—from the leap into business ownership to the highs, lows, and lessons learned along the way. Then, in the second half, we get into what he knows best: compensation strategy. 

We talk about the difference in expectations between baby boomers and millennials, how a well-crafted comp plan can attract top talent, and the surprising ways in which companies often get compensation wrong.

If you’re a business owner, HR leader, or just curious about how smart compensation design can impact everything from recruitment to retention—this episode is for you.

Scott's Company:
Trumpolt Compensation Design Solutions
https://hrcompensationconsulting.com

Chapters:
00:00:00 Introduction to The Reluctant Entrepreneur Podcast  
00:02:39 Transition from Corporate HR to Entrepreneurship
00:05:37 The Journey of a Reluctant Entrepreneur
00:08:31 Exploring Global Compensation Differences
00:11:29 Evaluating the Market Value of Your Work
00:14:15 Managing Career Uncertainty and Control
00:16:57 Building Multiple Revenue Streams
00:19:53 Building a Career Architecture: A Personal Journey
00:22:56 Why 80% of Businesses Fail: Lack of Adaptability and Skill Acquisition
00:25:39 Overcoming Business Challenges and Staying Motivated
00:28:40 Strategies for Balancing Business and Niche Services
00:31:41 Finding Passion and Delegation in Business
00:34:19 Misconceptions About Compensation Design 
00:37:06 Crafting Effective Compensation Plans: Market-Based and Transparent
00:40:08 Unique Compensation Strategy in a Small Company
00:43:13 Career Architecture for Employee Growth and Retention
00:45:56 Enhancing Employee Engagement Through HR Strategies
00:49:00 Pay Transparency and Career Development
00:51:43 Importance of Career Development and Employee Engagement
00:54:30 Prioritizing Company Culture Over Salary
00:57:12 Building a Values-Based Startup Culture
01:01:03 Defining Success in Entrepreneurship
01:03:07 Redefining Success and the Limitations of Wealth
01:05:42 The Reluctant Entrepreneur - Anatomy of a Business Startup: From Uncertainty to Success

Welcome to The Reluctant Entrepreneur Podcast—where we dive into the real stories behind entrepreneurship, the highs, the lows, and everything in between. Today, we have a fantastic guest who knows all about building careers, businesses, and meaningful conversations.  

Joining me is Bryce Batts, the founder of Career Collective, a seasoned career and business coach, and the host of the Wine After Work podcast. 

With a passion for helping professionals find their true calling and entrepreneurs build sustainable businesses, Bryce has guided countless individuals through career transitions, personal branding, and the mindset shifts needed for success.  

But Bryce doesn’t just talk business—she also brings insightful, candid conversations to her podcast, Wine After Work, where she sits down with inspiring guests over a glass of wine to discuss work, life, and everything in between.  

Today, we’re going to talk about her entrepreneurial journey, the lessons she’s learned as a coach, and the power of networking and personal branding. Plus, we’ll get a behind-the-scenes look at Wine After Work and what it takes to host a successful podcast.  

Bryce's Company:
Career Collective
https://www.mycareercollective.com

Dr. Kyle Hulsebus, a third-generation chiropractor and health and human potential specialist. With over 40 years immersed in the philosophy of health and well-being, Dr. Kyle brings a wealth of knowledge to our discussion. 
 
Beyond his chiropractic practice, Dr. Kyle is an author, speaker, and educator dedicated to aligning individuals and organizations to a state of wholeness. His unique approach integrates physical health with mental and spiritual well-being, aiming to achieve mastery across all seven areas of life. 

Dr. Kyle's commitment to continuous learning is evident in his extensive study of over 13,000 books across multiple disciplines, enriching his syncretic knowledge. His proprietary system assists clients in balancing their personal and professional lives, fostering alignment within organizations. Drawing from his practices in aikido, tai chi, and ballroom dance, Dr. Kyle delivers content in a unique and engaging style.

Dr. Kyle’s "The 40 Over 40" initiative offers 40 practical tips designed to enhance health and longevity for individuals over 40. These tips encompass various aspects of well-being, including physical health, mental clarity, and emotional balance. They range from simple practices like mindful breathing and daily walks to more reflective activities such as meditation and goal setting. Collectively, these recommendations aim to empower individuals to lead healthier, more fulfilling lives as they age.
 
In today's episode, we'll delve into Dr. Kyle's journey, exploring how his diverse experiences and holistic approach have shaped his entrepreneurial endeavors. We'll uncover insights into achieving balance and alignment, both individually and within organizations. And, well we'll dive into Dr. Kyle’s unique 40 Over 40 program, which offers 40 practical tips designed to enhance health and longevity for individuals over 40. These tips encompass various aspects of well-being, including physical health, mental clarity, and emotional balance. 

They range from simple practices like mindful breathing and daily walks to more reflective activities such as meditation and goal setting. Collectively, these recommendations aim to empower individuals to lead healthier, more fulfilling lives as they age.

Dr. Kyle 's Website:
https://drkylehulsebus.com

Dr. Kyle's' YouTube Channel:
https://www.youtube.com/@DrKyleHulsebus

Dr. Kyle's 40 Over 40 Series:
https://www.youtube.com/@DrKyleHulsebus/playlists

Dr.Kyle's Recommended Book:
Zen in the Art of Archery

by Eugen Herrigel (Author)
https://www.amazon.com/stores/Eugen-Herrigel/author/B000APRIPU?ref=ap_rdr&isDramIntegrated=true&shoppingPortalEnabled=true 

Stephanie Utterback is the founder and CEO of Epic BNB, a company that has carved out a unique space in the short-term rental industry. From navigating the challenges of entrepreneurship to building a brand that stands out in a competitive market, Stephanie has seen it all.  

In this episode, she takes us behind the scenes of her entrepreneurial journey—what inspired her to start Epic BNB, the obstacles she’s had to overcome, and the pivotal moments that shaped her success. 

We’ll talk about the realities of running a business in the short-term rental space, how to turn setbacks into stepping stones, and the advice she has for aspiring and current entrepreneurs looking to make their mark.  

If you’ve ever considered diving into the world of short-term rentals or wondered what it takes to build a thriving business from the ground up, you won’t want to miss this conversation. 

Stephanie's Business:
epicbnb
https://www.epicbnb.com
(615) 863-3444
[email protected]

Have you ever watched an ad that made you laugh out loud—and actually want to buy the product? 
That’s the magic of today’s guest, Joseph Wilkins, the founder of Funny Sales Videos. Joseph has mastered the art of blending humor with marketing to create viral, high-converting video campaigns that don’t just entertain but also drive real business results.  

In this episode, we dive into Joseph’s entrepreneurial journey, from his early career in traditional marketing to launching a company that helps brands connect with their audience through storytelling and comedy.

We’ll talk about the highs and lows of building a business in the ever-changing digital landscape, how resilience plays a key role in entrepreneurial success, and why humor is one of the most powerful tools in modern advertising.  

 Whether you’re an entrepreneur, marketer, or someone who just loves a good laugh, this episode is packed with insights on creativity, business growth, and standing out in a crowded marketplace.  
So sit back, relax, and get ready for an engaging conversation with Joseph Wilkins! 

Joseph's Company:
Funny Sales Videos
https://funnysalesvideos.com

My guest today is Dominic Rubino. Dominic Rubino is a seasoned entrepreneur and business coach with over 20 years of experience in the construction industry. He’s founded, developed, and sold multiple companies, focusing on implementing straightforward systems to help contractors work more efficiently and profitably. 

As the host of the Profit Tool Belt podcast, Dominic educates contractors on the business aspects of the construction industry. The podcast covers a wide range of topics, including time management, estimating, profitability, hiring, and company growth. Dominic interviews top business owners and experts to provide valuable insights to his audience. 

In addition to the Profit Tool Belt, Dominic hosts the Cabinet Maker Profit System podcast, further extending his reach within the construction sector. He is also the author of "Construction Millionaire Secrets," a book that reveals strategies for building a million-dollar contracting business through simple systems. 

Whether you’re a contractor, cabinet maker, or have or are thinking of embarking on virtually any other type of business, Dominic’s business Journey has taught him, and hopefully you, some valuable lessons.

Dominic's Company:
https://www.profittoolbelt.com

Today, I’m thrilled to have a very special guest, Tarra Stubbins, the founder and CEO of Take It Easy Group, a company specializing in providing fractional executive assistant services to help startups and businesses scale successfully.  

With over 20 years of experience as a personal assistant, Tarra spent a decade on the road supporting renowned musicians and entertainers, including The Rolling Stones, The Red Hot Chili Peppers, Kenny Rogers, Nickelback, and KISS. 

In 2007, after her extensive touring experience, Tarra established Take It Easy Personal Concierge Inc. to assist CEOs and entrepreneurs in managing their time and tasks effectively.  

Her passion for helping others succeed led to the creation of Take It Easy Group, focusing on offering experienced executive assistant services to seed and Series A companies aiming to scale efficiently. 

Tarra emphasizes the importance of time management, goal setting, and leveraging one's network as key strategies for success. She believes in empowering entrepreneurs to unlock their potential through better habits and effective delegation. 

Tarra's Company
Take it Easy Group
https://www.takeiteasygroup.com