
Cupalo Conversations
In each episode of Cupalo Conversations, Lauren Hannon founder of Cupalo delves into insightful conversations with a diverse and exceptional lineup of guests. Each episode is a deep dive into the grit that lives between the lines of success stories, offering listeners a unique perspective on the challenges and triumphs of each guest. From software engineering leaders to financial experts, authors to fellow founders, and an array of rabble rousers in between, Lauren explores the multifaceted world of staffing, scaling development teams, building businesses, personal development, and more.
Latest episodes

Nov 27, 2024 • 36min
Episode #46 Artificial Intelligence: Super Power OR Super Problem with Jason Louer
Is AI the ultimate tool to unlock human potential, or are we trading our privacy and humanity for convenience?
In this episode of Cupalo Conversations, host Lauren Hannon chats with Jason Louer, a seasoned engineer and leader, about the transformative impact of AI on engineering, business, and everyday life. They dive into AI as a force multiplier, its potential to bridge the skills gap, and how it enhances both technical and communication abilities. Jason highlights the importance of aligning AI with real-world business problems and using it as a learning tool while tackling the pressing issue of job security in the AI-driven era.
Beyond the workplace, they discuss how AI empowers non-technical individuals to streamline daily tasks, unlocking new levels of efficiency. However, the conversation takes a sobering turn as they address AI's darker side, such as its misuse in global surveillance by unchecked governments—echoing Orwellian warnings from 1984. Jason underscores that despite AI's power, there’s no substitute for human experience—our ability to learn, feel, and authentically connect remains irreplaceable.
This episode explores the balance between leveraging AI for innovation and safeguarding humanity's core values, making it a must-listen for anyone curious about the opportunities and challenges of artificial intelligence.
00:00 Jason's Journey in Data Engineering
04:47 AI As A Force Multiplier
08:08 Bridging Skills Gap with AI
12:53 The Risk of Underdevelopment At the Use of AI
14:58 AI's Impact on Technical Jobs
17:09 Embracing AI Tools for Value Creation
18:21 Leadership Leveraging AI
21:23 AI's Role in Everyday Life
25:06 The Negative Side to AI
31:48 No Substitution for Human Experience
Though Jason works for the American Red Cross, the opinions expressed represent his own and do not reflect the views of his employer.

Nov 14, 2024 • 39min
Episode #45 Sh*tHappens: Inventing "The Poopcopter" a Dog Waste Removal Drone with Caleb Olson
For the dog feces handler in all of us—meet the Poopcopter, the drone that steps in and picks up, so you don’t have to.
In this episode of Cupalo Conversations, join host Lauren Hannon as she interviews Caleb Olson, the creator of the Poopcopter, a groundbreaking drone designed to automate dog waste removal. Caleb reveals the journey behind his innovative invention, diving into its design, functionality, and the technical challenges he’s overcome. With hundreds of hours invested, Caleb discusses balancing a full-time job with his passion project and offers advice for aspiring inventors on time management, the importance of feedback, and leveraging cross-disciplinary knowledge.
As a software engineer, Caleb is most comfortable in the technical realm, but he shares the trials of navigating the business side, from patents to potential public speaking opportunities. Key insights include the value of passion in problem-solving, the power of collaboration, and the importance of taking the first step. Tune in to discover how Caleb’s journey exemplifies the intersection of hardware and software, and how innovation can emerge from unexpected places. Perfect for tech enthusiasts, aspiring inventors, and anyone fascinated by real-world applications of cutting-edge tech!
00:00 Introduction to Caleb Olson, Inventor of The Poopcopter
05:00 Challenges and Innovations in Design
06:23 Patent Process & Intellectual Property
08:54 Caleb's Other Inventions
13:59 Problem Solving & the Passion Behind the Invention
16:42 Staving Off Cultural Pressures
18:42 Navigating External Opinions and Advice
25:28 Staying in Your Lane: The Importance of Specialization
30:44 Embracing Public Challenges and Personal Growth
33:17 To Try Or Not to Try: Overcoming Fear
Connect with Lauren Hannon
Sign up for "Cupalo Newsletter" (Lauren's email newsletter): https://cupalo.substack.com/
Follow Lauren on LinkedIn: / hannonlauren
Check out Cupalo's website: https://cupalo.io

Nov 7, 2024 • 30min
Episode #44 How to Think Like a Business Owner: From Craftsperson to CEO with Brad Koehn
In this episode of Cupalo Conversations, Brad Koehn shares invaluable insights on the shift from employee to business owner, diving into the mindset changes required to build a profitable business.
Brad discusses the unique challenges craftsperson business owners face, especially those who excel at their trade but struggle to develop essential business skills. He emphasizes seeing your business as a "money-making machine" and highlights strategies for structuring it for potential exits.
Listeners will learn the importance of shifting from individual craftsmanship to team-focused leadership, the pros and cons of product vs. service-based models, and tips for building a sustainable, adaptable business.
Key Takeaways:
Work on your business, not in it, to ensure growth.
Treat your business as a structured money-making machine.
Leverage technology and outsourcing to manage workload.
Transition from personal skillset to team and leadership development.
Balance autonomy with the solopreneur lifestyle's limitations.
Sales, marketing, and emotional resilience are essential skills.
Start planning your business exit strategy early on.
Service businesses often offer greater stability than product-based models.
Adaptability is critical for long-term business success.
00:00 The Transition from Employee to Business Owner
03:38 More Running the Bakery & Less Baking
06:40 The Solopreneur Lifestyle and Its Challenges
12:43 Word of Caution to Craftspeople Business Owners
16:42 Product vs. Service Company: The Business Model Debate
19:17 Building a Business with an Exit Strategy
24:23 Entrepreneurship Through Acquisition
27:14 Navigating Fear in Business Ownership
Connect with Lauren Hannon
Sign up for "Cupalo Newsletter" (Lauren's email newsletter): https://cupalo.substack.com/
Follow Lauren on LinkedIn: / hannonlauren
Check out Cupalo's website: https://cupalo.io

Oct 31, 2024 • 30min
Episode #43 Life on the Line with Chef Tony Andiario
In this episode of Cupalo Conversations, host Lauren Hannon sits down with celebrated chef Tony Andiario, the James Beard semifinalist and co-owner of the acclaimed West Chester, PA restaurant, Andiario. Tony shares his remarkable journey from a graphic design graduate to a highly regarded chef whose restaurant is one of the most sought-after dining experiences in the Philadelphia suburbs.
Tune in to hear Tony’s honest insights on the culinary world—the often-grueling physical demands, the misconceptions of the "celebrity chef" lifestyle, and his joy in crafting approachable, unfussy food that anyone can enjoy. He shares how family gatherings around food and watching cooking shows with his father ignited his passion, ultimately leading him to pursue cooking over graphic design at age 25.
Tony’s culinary philosophy centers on simplicity, quality ingredients, and creating a comfortable atmosphere for diners, and he encourages everyone to find joy in cooking at home. Discover what Tony would choose for his last meal and how the simple act of sharing food with loved ones fuels his love for the kitchen.
Key takeaways
Tony's culinary journey began with family gatherings centered around food.
His passion for cooking was influenced by watching cooking shows with his father.
He transitioned from graphic design to culinary school at 25, driven by a desire to pursue cooking.
The physical demands of being a chef can be challenging, especially as one ages.
Tony believes that the chef celebrity craze can misrepresent the realities of the profession.
He finds joy in the creativity and craftsmanship involved in cooking.
Approachable food that is not fussy is what Tony aims to create in his restaurant.
Tony's ideal last meal would be simple, comforting food shared with friends and family.
He encourages others to find joy in cooking at home rather than feeling pressured to switch careers.
Good ingredients from farmers markets can enhance the cooking experience.
00:00 Introduction to Tony & His Circuitous Route to the Kitchen
07:48 The Physical Toll of Being a Chef
14:56 To Find Your Calling in Food
19:49 The Best Part of Being a Chef
22:48 Food Over Fussy
26:04 Tony's Ideal Last Meal on Earth
Connect with Lauren Hannon
Sign up for "Cupalo Newsletter" (Lauren's email newsletter): https://cupalo.substack.com/
Follow Lauren on LinkedIn: / hannonlauren
Check out Cupalo's website: https://cupalo.io

Oct 24, 2024 • 44min
Episode #42 The Miraculous & the Macabre: Weird Catholic Handbook with Author Michael Lichens
Do you savor a good ol' fashioned ghost story? Do you enjoy stepping into a room filled to brim with human bones? What about facing your mortality head on?
Well, well, well. Do I have a podcast (and a book) for YOU!
In this Cupalo Conversations podcast, Lauren Hannon interviews Michael Lichens, an author and editor with a deep passion for the overlooked aspects of Christian history. They discuss Michael's latest book, 'Weird Catholic Handbook,' exploring themes such as ossuaries, saints, relics, and the phenomenon of incorruptibility.
Michael retells the tail of some of America's most famous ghost stories and exorcisms, providing a historical perspective on these topics and how they relate to modern spirituality.
In this conversation, Michael J. Lichens discusses the resurgence of spirituality in uncertain times, exploring haunted and holy places in the U.S., the impact of historical tragedies on spirituality, and the importance of imagination in understanding history.
He reflects on the sensitivity to everyday spaces, the role of unusual experiences in deepening faith, and the confrontation with the fear of death. Lichens also addresses skepticism towards the miraculous and emphasizes the need to revive the tradition of storytelling as a means of connecting with our shared human experience.
00:00 Introduction to Michael Lichens and His Journey
02:34 Newly Published Weird Catholic Handbook
03:19 Bone Churches: Their History & Spiritual Complexity
07:37 Catholic Saints and Relics
08:55 Phenomenon of Saintly Incorruptibility
12:59 Ghost Stories & Exorcisms
21:20 The Rise of Spirituality in Post War & Modern Times
22:46 Haunted & Holy United States
28:03 Sensitivity to the Lives of Those Who Came Before
30:24 The Role of the Unusual in Deepening Faith
33:00 Confronting the Fear of Death
35:30 Addressing Skepticism Towards the Miraculous
39:15 Understanding Human Nature Through History
41:32 Reviving the Tradition of Storytelling
Tune in and discover the bizarre and extraordinary stories that have shaped Catholicism and our human history with Michael Lichens and his "Weird Catholic Handbook"
Connect with Lauren Hannon
Sign up for "Cupalo Newsletter" (Lauren's email newsletter): https://cupalo.substack.com/
Follow Lauren on LinkedIn: / hannonlauren
Check out Cupalo's website: https://cupalo.io

Oct 17, 2024 • 34min
Episode #41 Kids Over Corporate: Family, Faith, and Modern Parenting with Ally Hieronymus
Ally is thriving in what some might consider "today's abnormal" as a stay-at-home mom of five soon to be six kiddos!
In this episode of Cupalo Conversations, host Lauren Hannon interviews Ally Hieronymus, a former pastry chef and culinary artist turned stay-at-home mom of five (soon to be six). Ally shares her heartfelt journey to embracing the joy and challenges of raising a large family in today’s world. They discuss the stigma that often surrounds moms of many children—how strangers make forward or rude comments about the number of kids and their close age gaps.
Ally opens up about her faith-driven approach to parenting, acknowledging her imperfections while surrendering to God's will. She reflects on the pros and cons of technology for modern parents, from building a supportive community to dealing with the pressure of feeling inadequate. Despite stepping away from her culinary career, Ally's passion for creativity now centers on raising her children to become the best people they can be.
Join this honest, faith-filled conversation about modern parenting, large families, and embracing what some may consider "today’s abnormal." Whether you’re a parent, aspiring mom, or someone interested in faith and family dynamics, this episode is for you.
Tune in for a heartfelt conversation that sheds light on the beauty of large families and how Ally is thriving in what some might consider "today's abnormal."
#Motherhood #LargeFamily #FaithAndFamily #ParentingJourney #StayAtHomeMom #RaisingKids #ParentingIn2024 #CupaloConversations #LaurenHannon00:00 Intro to Ally & Her Journey to Entrepreneurship & Motherhood
06:38 Scratching the Entrepreneurial Itch
09:05 Motherhood as a Vocation
11:31 Holding Fast to Joy & Remaining Steadfast in Faith
13:57 Discrimination & Misunderstanding
17:37 The Labels We Carry: Stay-at-Home Moms vs. Trad Wives
20:06 Accepting the Role of Stay-at-Home Mom
22:20 Technology's Double-Edged Sword in Parenting
27:45 Finding Balance: Homeschooling and Future Endeavors
30:29 Navigating Public Perception & Beseeching Respect
Connect with Lauren Hannon
Sign up for "Cupalo Newsletter" (Lauren's email newsletter): https://cupalo.substack.com/
Follow Lauren on LinkedIn: / hannonlauren
Check out Cupalo's website: https://cupalo.io

Oct 10, 2024 • 50min
Episode #40 The Great Escape: From 9-to-5 Grind to 6-Figure Freedom with Daniel Vassallo
Ever thought of quitting your soulless full time job to work for yourself? What about when you're making $500k+???
In this episode of Cupalo Conversations, host Lauren Hannon sits down with Daniel Vassallo, a former Amazon software engineer turned entrepreneur, Twitter influencer, and founder of the Small Bets Community. Daniel shares his bold transition from a cushy $500,000+corporate job to the uncertain world of self-employment. With over four years of savings, he took the leap, driven by the conviction that full-time employment wasn’t the right fit for him.
Daniel introduces his powerful concept of "small bets"—embracing smaller, manageable ventures to mitigate risks in business. He talks about redefining success beyond financial gain and highlights the unpredictability of the market and of life in general. A cautionary reminder to remove the blinders and recognize that life is multi-dimensional.
If you're an aspiring entrepreneur seeking freedom from the 9to5 grind, as well as advice on lifestyle design and navigating uncertainty, Daniel’s journey will inspire you.
Key Takeaways:
Why Daniel left a lucrative corporate job to follow his entrepreneurial calling.
The role financial security plays in making bold decisions.
How "small bets" can reduce business risk and enhance personal satisfaction.
The importance of resilience, adaptability, and community in achieving success.
Why finding joy in the journey is as crucial as reaching the destination.
#DanielVassallo #Entrepreneurship #SmallBets #FinancialIndependence #LifestyleDesign #CupaloConversations #LaurenHannon #Amazon #SelfEmployment #businesssuccess
00:00 Daniel's Journey into Corporate America
07:55 Leaving the High-Paying Job & $100,000s on the Table
12:27 Luck Blindness: Acknowledging the Randomness of Life
18:17 Post- Amazon: Early Ventures and Lessons Learned
26:44 The Strategy of Small Bets
31:04 Measuring Success Outside of Full Time Employment
37:22 Passion Project to Commercial Project
40:58 The Trues Measure of Success: Making Yourself Proud
Connect with Lauren Hannon
Sign up for "Cupalo Newsletter" (Lauren's email newsletter): https://cupalo.substack.com/
Follow Lauren on LinkedIn: / hannonlauren
Check out Cupalo's website: https://cupalo.io

Oct 3, 2024 • 31min
Episode #39 Semper Fi: Loyalty, Learning, & Leading in Tech with Marine Veteran Jared Olhoft
Jared Olhoft, a former U.S. Marine and a technology leader in the Twin Cities, discusses his remarkable transition from military service to tech leadership. He emphasizes how military principles shaped his approach, moving from authoritarian methods to adaptive leadership. Listeners learn about the importance of continuous learning, maintaining a balance between self-care and loyalty, and the benefits of networking. Jared also highlights how diverse experiences, particularly those of veterans, can enhance leadership perspectives in the corporate world.

Sep 26, 2024 • 44min
Episode #38 A Day in the Life of a C-Suite Tech Exec with Marc Kermisch
00:00 Introduction: Marc Kermisch & His Journey to the C Suite
03:02 Life as a CTO/CIO
05:47 The Technical Aptitude Spectrum
08:57 Leaders Needing to Be Led: Seeking Mentorship as an Executive
12:26 Overcoming Self-Doubt
16:44 Career Progression Beyond the C-Suite
19:48 Navigating Politics and Bureaucracy at the Top
24:18 Behind Those Feel-Good Mission Statements
30:36 Carrying the Weight of Layoffs as a C-Suite Exec
37:36 Understanding the C-Suite Perspective
In this episode of the Cupalo Conversations podcast, host Lauren Hannon sits down with Marc Kermisch, a renowned Twin Cities tech leader who has held C-suite positions at Red Wing Shoe Co, Bluestem Brands, OptumRX, and CNH Industrial. Marc shares his incredible journey from an English major to CTO/CIO, shedding light on the real struggles and emotional challenges of leadership at the top.
In this honest conversation, Marc opens up about the tremendous responsibility and often personal sacrifice that comes with the job of being an executive. Marc emphasizes the need for ongoing mentorship the higher you climb on the ladder. How self-doubt and navigating corporate politics persist at the top and what it's like to wade through those waters. The importance of continuous learning and self-awareness in leadership success.
They also discuss the emotional toll of layoffs and balancing leadership decisions with empathy as well as what a "real" mission statement means in driving company goals.
Tune in to hear Marc’s story of embracing challenges, learning from setbacks, and making a lasting impact as a tech leader. Whether you're climbing the corporate ladder or looking to develop your leadership skills, this episode offers valuable takeaways for personal and professional growth
Connect with Lauren Hannon
Sign up for "Cupalo Newsletter" (Lauren's email newsletter): https://cupalo.substack.com/
Follow Lauren on LinkedIn: / hannonlauren
Check out Cupalo's website: https://cupalo.io/

Sep 19, 2024 • 36min
Episode #37 Ten-Ten-Ten: The Goal Setting Blueprint with Kurt Schmidt
00:00 Introduction to Kurt Schmidt and His Journey
03:17 Crafting Life with Strategic Precision
08:12 Striking the Balance Between Future Goals & Present Living
10:05 The Importance of Socializing Goals
14:35 The Myth of the Self-Made Individual
17:02 The Antithesis of Planning: Living Spontaneously
19:36 10-10-10 Framework Explained
22:41 Daily Rituals and Self-Reflection
27:35 Dealing with Negative/Cynical People
31:26 Reflections on Legacy & Mortality
34:00 Future Aspirations and Community Building
In this episode of Cupalo Conversations, host Lauren Hannon sits down with Kurt Schmidt, a business leader with over 20 years of experience in growing professional service firms. Kurt shares his journey from a successful action sports athlete to leading a company’s growth from 50 to 500 employees and becoming the founder of Schmidt Consulting Group.
They dive deep into his book, “The TEN-TEN-TEN Blueprint: Craft Your Life With Strategic Precision,” where Kurt outlines a powerful framework for goal setting with 10 years, 10 months, and 10 weeks in mind. Discover why it’s crucial to socialize your goals—sharing your plans with others to ensure support and accountability. Kurt emphasizes that no one achieves success alone and debunks the myth of the self-made individual.
Lastly, Kurt also touches on the significance of leaving a legacy, living a life you can be proud of, and how to take control of your future with actionable strategies.
Tune in to learn more about goal setting with the TEN-TEN-TEN framework so you can ultimately make yourself proud and live the life you always dreamed of.
Connect with Lauren Hannon
Sign up for "Cupalo Newsletter" (Lauren's email newsletter): https://cupalo.substack.com/
Follow Lauren on LinkedIn: / hannonlauren
Check out Cupalo's website: https://cupalo.io/