Cupalo Conversations

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!

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0:00 Introduction and Technical Setup

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/

00:00 Introduction and Christian's Journey

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.

00:00 Introduction and Jayant's Journey

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.

00:00 Introduction and Background

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.

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/

00:00 Introduction and Background

02:04 Building High-Performing Teams

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.

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.

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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.

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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/