
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

Sep 12, 2024 • 35min
Episode #36 Behind Closed Doors: An Exposé on American Finances with Underwriter Joe Coulter
00:00 Joe's Journey into the Mortgage Industry
02:52 Behind Closed Doors: Million Dollar Homes
05:25 The Buying Power of High Dollar Earners
10:42 Savings & Investments of "Rich" Americans
13:18 Earnings and Buying Power of "Average" Americans
15:14 Americans and Their Debt
17:32 Impact of Rise in Interest Rates & Home Values
21:22 Cautionary Tales and Warnings on Cash Out Refinancing
27:55 When & How to Seek Expert Advice on Home Buying
In this fun and yet sobering episode of the Cupalo Conversations podcast, host Lauren Hannon sits down with Joe Coulter, a senior underwriter with over 15 years of experience and more than 10,000 mortgage loans under his belt. Together, they explore the often hidden truths about how Americans—both average and affluent—really manage their money.
From paycheck-to-paycheck living in multi-million-dollar homes to the common mistakes people make with cash-out refinances, Joe pulls back the curtain on the financial habits that most of us don’t talk about with friends such as...
How even those with $100,000+ monthly paychecks may be one missed payment away from returning their luxury cars.
The pitfalls of repeatedly using home equity to pay off debt and the long-term consequences.
Why pouring hundreds of thousands (or millions) into home renovations rarely pays off in full.
Rich in juicy stories and expert advice, Joe unveils what real Americans are earning, spending, and struggling with in today’s economy. Don’t miss this fascinating behind-the-scenes look at personal finance!
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 5, 2024 • 26min
Episode #35 Beyond the W-2: Navigating Non-Traditional Loans with Karen Lagasse
0:00 Introduction and Technical Setup
00:09 Introducing Karen Lagasse and Her Experience in the Mortgage Industry
01:56 The Most Challenging Real Estate Market
04:12 The Impact of Unemployment and Layoffs on Borrowers
08:03 The Impact of Layoffs on Borrowers
09:38 Qualifying for a Mortgage and Self Employment
16:05 Non-Traditional Loan Programs on Investment Properties
23:44 Excitement for the Future and Refinancing Opportunities
n this episode of Cupalo Conversations, host Lauren Hannon sits down with her mother, Karen Lagasse, a senior loan officer (NMLS#44031) with Northpoint Mortgage, Inc. (NMLS #1515). Together, they delve into the intricacies of non-traditional loan programs, focusing particularly on the challenges faced by self-employed individuals who are rich in assets but may lack the conventional income documentation required for traditional loans.
Karen shares her expert insights on the importance of financial planning for aspiring entrepreneurs, emphasizing the need to be prepared to file two years of tax returns as a self-employed individual. She also highlights alternative loan options, such as bank statement programs, which can be a lifeline for those who don’t meet conventional criteria.
The conversation also touches on investment properties, where Karen discusses loan programs that consider the debt service coverage ratio (DSCR) and the use of rental income to qualify for loans. She underscores the significance of planning ahead, particularly when transitioning from a W-2 job to self-employment, and how this shift can impact one’s ability to purchase a primary residence.
Listeners will gain valuable advice on navigating the mortgage landscape, understanding the impact of rates and market conditions, and the importance of staying informed to seize opportunities, such as refinancing when rates are favorable. This episode is a must-listen for anyone considering an entrepreneurial path or looking to invest in real estate with a non-traditional loan.
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/

Aug 29, 2024 • 34min
Episode #34 Becoming An Independent Contractor with Aaron Loes
00:00 Introduction and Aaron's Journey into Tech
03:41 Making the Transition: From Full-Time Employee to Independent Contractor
04:45 How to Set Up Your Own Business
06:03 The Importance of Seeking Expert Advice
08:12 Overcoming Concerns About Independent Contracting
13:00 Financial Aspects of Independent Contracting: Earning Potential and Costs
14:47 Simplifying Payroll: Using Services for Contractors
15:45 The Financial Aspects of Contracting
19:58 Maintaining Control of Your Schedule
22:28 Contracting as an Alternative to Management
25:45 Building a Network in the Contracting Community
27:20 The Importance of Research and Preparation
29:06 Factors for Returning to FTE/Salaried Positions
In this episode of Cupalo Conversations, host Lauren Hannon sits down with Aaron Loes, a seasoned full-stack software engineer, to delve into the world of independent contracting. Aaron shares his journey into technology and offers a comprehensive guide to setting up a contracting business, covering everything from registering your business to navigating tax obligations.
The discussion highlights the unique benefits and challenges of contracting, including the satisfaction of earning money through your own efforts, managing finances like invoicing and payroll, and exploring flexible retirement options. Aaron emphasizes how contracting allows engineers to continue doing what they love without being pushed into management roles, offering more control and flexibility in their careers.
Aaron also underscores the importance of building a strong network and seeking advice from others in the contracting community. He encourages those considering the leap into contracting to do their research, prepare thoroughly, and take advantage of the potential for higher earning and personal satisfaction that contracting offers.
If interested in taking the leap, tune in here to learn how and to maybe get that little extra encouragement needed to do so.
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/

Aug 22, 2024 • 38min
Episode #33 Discipline: The Bridge Between Dreams and Success with Christian Leva
00:00 Introduction and Christian's Journey
07:15 The Root of All Success is Discipline
10:29 Leveraging the Initial Rush of Motivation
15:02 Working Harder on Yourself Than You Do on Your Day Job
18:08 The Skill of Setting Goals
26:27 The Meaning of Success
29:15 The Un-glorified Role of Hard Work in Success
32:36 Constant Learning and Accomplishing Complex Objectives
34:34 Cautionary Note for Dreamers and Goal Setters
In this compelling episode of Cupalo Conversations, host Lauren Hannon sits down with Christian Leva, a distinguished leader in KPMG's application security and controls practice. Christian offers listeners a deep dive into his remarkable journey in consulting and application security, revealing the discipline and determination that have driven his professional success.
But Christian's achievements don’t stop at the office. Outside of his career, he has won three gold medals at the Junior Olympics, earned his pilot's license, and completed his scuba recertification. These personal milestones highlight his relentless pursuit of new goals and his commitment to pushing beyond boundaries, both professionally and personally.
Throughout the conversation, Christian emphasizes the crucial role of discipline in achieving success. He shares his meticulous process of goal-setting, continuous learning, and his annual review of goals to ensure he stays on track. Christian underscores the hard work and sacrifices behind every accomplishment, cautioning against the dangers of dreaming without action.
At the heart of this discussion is a powerful message: Discipline is the bridge between dreams and success. Christian’s passion for storytelling and his insights into the importance of finishing what you start serve as a compelling reminder that discipline is the foundation of all success.
Tune in to discover how Christian Leva raises discipline to the level it deserves and how his approach can inspire you to achieve your own dreams.
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/

Aug 15, 2024 • 40min
Episode #32 Fixer Upper: Saving Businesses & Projects from Total Failure with Jayant Chaudhary
00:00 Introduction and Jayant's Journey
03:40 The Importance of Literature
06:27 Fixing Troubled Projects: A Systematic Approach
11:03 Estimation Challenges and Building Trust
17:56 Challenges Faced by Startups: Software vs Product Phase
22:22 Prioritizing Customer Feedback for Effective Delivery
25:32 Addressing Low Morale & Fragile Egos in Teams
29:38 A Checklist for Successful Project Execution
33:15 Applying Principles of Process and Delivery to Personal Growth
37:16 Being a Fixer in Organizations & Working Yourself Out of a Job
In this episode of Cupalo Conversations, host Lauren Hannon sits down with Jayant Chaudhary, the visionary founder of eProxim, a technology leader renowned for his expertise in rescuing failing businesses and large-scale projects. Jayant shares compelling "war stories" from his career, detailing how he has helped enterprises and startups on the brink of failure.
Throughout the conversation, Jayant underscores the value of transparency, honesty, and adherence to best practices as foundational principles for success. He also discusses the unique challenges faced by startups and enterprise organizations, noting that creating a product involves far more complexity than merely developing software. Jayant stresses the importance of taking customer feedback seriously to prioritize and deliver effective solutions. He emphasizes the critical importance of non-functional requirements like security and certification, which are often overlooked by startups struggling to ship their first product.
Additionally, Jayant offers insights into boosting employee morale by fostering teamwork and recognizing individual contributions. He provides a practical checklist of key areas to focus on, including following a process, test-driven development, maintaining strong interpersonal relationships, managing the project life cycle, and adhering to a consistent delivery cadence. These principles, he notes, are not only applicable to organizational success but also to personal growth and career advancement.
Finally, Jayant reflects on his role as a "fixer" in organizations, describing how it offers a unique variety of challenges and the opportunity to solve diverse problems, ultimately making a significant impact.
Tune in to learn Jayant's methodical approach for righting these wayward ships and getting companies/projects back on track!
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/

Aug 8, 2024 • 36min
Episode #31 Finding Your Working Genius with Marie Schutte
00:00 Introduction and Background
02:13 Discovering the 6 Working Geniuses
06:35 Discovering Our Frustrations
07:40 Applying the Working Genius Model in Teams
10:39 Aligning Roles with Working Geniuses
15:13 Setting Leaders Up for Success with Working Genius
19:12 Working Genius and Augmenting a Team
21:52 Origin of Our Geniuses and Change
24:25 Applying Working Genius to Personal Life
28:08 The Magic & the Beauty of Working Genius
30:31 Integration of Working Genius in Relationships
34:44 Taking Away the Shame of What We Want
In this episode of Cupalo Conversations, host Lauren Hannon delves into the transformative power of the Working Genius model with special guest Marie Schutte. They explore how this model can be a game-changer for teams, leaders, and individuals by identifying the types of tasks that energize and engage people, as well as those that drain them. This crucial insight fosters self-awareness, helping individuals understand their reactions, strengths, and areas for growth in both their professional and personal lives.
The Working Genius model consists of six geniuses: wonder, invention, discernment, galvanizing, enablement, and tenacity. Each of these geniuses represents a unique way in which individuals contribute to the creation and completion of tasks.
Marie shares her own working geniuses, discernment and galvanizing, and provides a detailed explanation of each genius:
Wonder - The ability to ponder possibilities and ask big questions.
Invention - The capacity to create new ideas and solutions.
Discernment - The knack for evaluating ideas and making sound judgments.
Galvanizing - The talent for rallying and motivating others to take action.
Enablement - The gift of providing support and assistance to make things happen.
Tenacity - The drive to push projects to completion and ensure quality results.
Marie discusses how understanding these geniuses can revolutionize team dynamics and effectiveness. She explains how the model can be integrated into team workshops and hiring processes to ensure that individuals are placed in roles that align with their natural strengths. By doing so, teams can enhance productivity, morale, and job satisfaction.
A key takeaway from the conversation is the importance of leaders being fully committed to the model. Marie emphasizes that for the Working Genius model to be truly effective, it must be continuously applied and integrated into everyday practices. She suggests incorporating the geniuses into team meetings and job descriptions to ensure alignment and maximize individual strengths.
The Working Genius model provides a common language and framework for individuals and teams to understand and appreciate their unique value and contributions. It encourages a culture of recognition and collaboration, where everyone's strengths are leveraged for collective success. This episode is a must-listen for anyone looking to boost their team's performance and create a more engaged and harmonious work environment.
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/

Aug 1, 2024 • 37min
Episode #30 Egoless Leadership: Building Teams with Integrity and Trust with Brian Johnson
00:00 Introduction and Background
02:04 Building High-Performing Teams
05:26 Investing in Team Building: Building a System
08:36 Vetting a Company's Culture: It's All About the People
12:34 Addressing Underperforming Team Members
19:38 Restoring Team Morale Following a Layoff
23:01 Unifying a Team Around a Vision
25:22 The Power of Self-Improvement in Leadership
33:06 The Importance of Going to Work on Yourself
In the 30th episode of Cupalo Conversations, host Lauren Hannon sits down with Brian Johnson, an IT leader with decades of experience, to explore an unconventional approach to building high-performing teams—slowly and deliberately. Oh, and without an ego. Brian shares invaluable insights on team building and leadership, emphasizing the critical importance of getting to know team members and fostering trust.
Throughout the discussion, Brian reveals that building a high-performing team requires more than just focusing on immediate tasks. It's about understanding individual roles, maintaining clear communication, and genuinely appreciating each team member's contributions. He highlights how leaders often overlook team dynamics in favor of urgent projects, leading to suboptimal performance.
Brian advocates for creating dedicated time and space to work on team dynamics and problem-solving, even within challenging corporate cultures. He also addresses the difficulties of team building in a poor culture and underscores the significance of finding a company with a supportive and positive environment.
Moreover, Brian shares his thoughtful process for evaluating a company's systems and culture when considering new opportunities, offering listeners practical advice on navigating their career paths.
Tune in to gain valuable perspectives on leadership and team development from an expert who believes in the power of patience and understanding in creating high-performing teams.
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/

Jul 25, 2024 • 38min
Episode #29 On Staying In Love With Your Craft with Sean Wesenberg
00:00 Introduction and Background
03:02 Software Engineer to People Leader
06:29 Balancing Act: Title, Status, Comp, and Passion
09:41 The Struggle to Stay in Love with Your Craft
13:53 The Pressure to Keep Learning & Expanding Your Skillset as an Engineer
17:09 Advice to Younger Self, Entry Level Engineer
19:01 The Role of Passion in Software Engineering
20:58 Addressing the Realty of Corporate America
24:37 The Next Generation of Engineers
29:06 Supporting Software Engineers' Development
31:35 Looking Ahead: The Next 20 Years
35:24 What About Working Less?
Join host Lauren Hannon in the 29th Cupalo Conversations episode as she chats with Sean Wesenberg, a software engineering veteran with over 20 years of experience. We dive into the raw and real aspects of tenured career and discuss finding ways to stay passionate about your craft after decades in the industry.
In this candid conversation, Sean opens up about his journey, sharing personal stories and hard-earned lessons on how to avoid boredom and keep the excitement alive in your career. He discusses the delicate balance between real life and career aspirations, offering practical advice on how to achieve both without sacrificing one for the other. Sean also talks about how his goals have evolved over time and how he's managed to adapt while staying true to his passion.
One of the key themes Sean emphasizes is the importance of continuous learning. Early in your career, staying on the bleeding edge of technology can be crucial for growth and advancement. However, he also advocates for the importance of self-care. Sean shares his perspective on not overworking yourself, taking breaks, and the value of stepping away from work to recharge.
This episode is a treasure trove of wisdom for all working professionals, but especially for software engineers. Whether you're just starting out or are a seasoned professional, Sean's insights will resonate with you. He reminds us that while dedication to your craft is important, so is taking care of yourself to sustain a long and fulfilling career.
Tune in to this episode of Cupalo Conversations to hear Sean Wesenberg's heartfelt advice on how to stay in love with your craft while maintaining a healthy work-life balance in this work-obsessed culture.
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/

Jul 18, 2024 • 37min
Episode #28 On Cultivating the Next Generation of Leaders with Deb Kaplan
00:00 Introduction and Deb Kaplan's Journey
04:19 Attributes of a Leader
06:09 How To Build High Performing Teams
08:57 Aligning Core Values
11:49 Setting Direction, Vision, and Alignment
13:49 The Next Generation of Leaders
15:20 Disenchantment in Corporate America
21:47 Personal Responsibility in Leadership Development
23:36 Navigating Poor or Ineffective Leaders
27:07 The Role of Interpersonal Skills in Coaching Up
30:15 The Importance of Introspection in Personal Growth
33:38 Advice for Future Leaders: Curiosity is a Superpower
In this enlightening episode of Cupalo Conversations, host Lauren Hannon sits down with Deb Kaplan, a seasoned organization performance consultant, coach, and Dale Carnegie trainer. Deb shares her inspiring journey and delves into the essential attributes that define a successful leader. She underscores the significance of core values, the art of building high-performing teams, and the imperative of nurturing the next generation of leaders.
Throughout the conversation, Deb addresses some of the most pressing challenges faced by today's workforce, including the dynamics of remote work, the impact of layoffs, and the growing disenchantment among the younger generation. She emphasizes the necessity for leaders to adapt and foster a supportive environment. Simultaneously, she highlights the individual's responsibility to develop their own leadership skills, both within and outside the traditional workplace.
The episode explores the critical role of self-accountability and self-assessment in personal growth. Deb and Lauren discuss how organizations can play a pivotal role in supporting and enabling individuals on their career journeys. They also touch on the intriguing concept of "leaders wanting to be led" and how individual contributors can effectively coach upwards to their leaders.
Tune in to gain valuable insights from Deb Kaplan on how to cultivate leadership skills, foster a culture of high performance, and navigate the complex landscape of modern work environments. Whether you're a seasoned leader or an aspiring one, this episode is packed with practical advice and thought-provoking perspectives.
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/

Jul 11, 2024 • 41min
Episode #27 Workers' Comp 101: Do's/Don'ts for Employers, Employees, & I.C.s with Jeremy Lagasse
00:35 Jeremy's Journey to Becoming an Attorney
04:08 Evaluating the Strength of a Claim Against an Employer
07:56 Mistakes Employers Make in Workers' Compensation
12:46 Preserving Employee-Employer Relations Following a Claim
17:01 Help! I am an Employee and I've Been Injured at Work. What do I do?
29:15 Understanding the Classification of Independent Contractors & Work Comp Coverage
34:55 Additional Insurance Coverage: Personal Injury, Un-insured, Under-Insured
In this episode of Cupalo Conversations, host Lauren Hannon sits down with her big brother, Jeremy Lagasse an attorney and Partner at Aaron Ferguson Law. Jeremy specializes in Personal Injury and Workers' Compensation, making him a seasoned expert in the field. Their discussion provides invaluable insights for both employers and employees regarding the complexities of workers' compensation claims.
Jeremy provides sage advice to employers, emphasizing the importance of employers being well-informed about workers' compensation laws and procedures and allowing insurance companies to do their due diligence. He also outlines critical mistakes to avoid, such as undermining an employee's claim or terminating an employee around the time of their claim without seeking proper legal counsel in advance.
When it comes to employees, clear communication is absolutely critical and time sensitive. Jeremy stresses the need for employees to communicate (in writing) and promptly about their injuries to their employers. He underscores the importance of seeking appropriate medical care immediately after a workplace injury. Delays in treatment can exacerbate injuries and complicate claims.
As a last major topic of discussion, Jeremy highlights the often-overlooked need for independent contractors to have adequate workers' compensation coverage, especially when their work involves travel. Without proper coverage, contractors can face significant financial and legal risks.
Tune in to this informative episode of Cupalo Conversations to learn more about the intricacies of workers' compensation from an expert in the field, and gain practical tips to safeguard your rights and responsibilities in the workplace.
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/