Cupalo Conversations

Cupalo Conversations

By Lauren HannonBusinessEntrepreneurship
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Cupalo Conversations episodes

  • Episode #16 Beyond the Rolodex: Authentic Networking & Human Connection with Ryan McKesson

    00:00 What is "Networking"

    02:53 The Benefits of Networking
    04:46 Embracing Imposter Syndrome & Networking Nerves
    07:54 Leveraging LinkedIn to Build and Foster Relationships
    15:32 Closing the Loop
    18:29 How to Approach Follow Ups
    24:45 Networking Flops
    In this episode of Cupalo Conversations, Ryan McKesson with 15+ years of sales experience quells the stigma around networking and celebrates the importance of authentic connections. Not just for professional but for personal growth.
    Introducing the concept of NATO networking (not attached to outcome), Ryan shares his thoughtful approach to reaching out to people with confidence in his value proposition and with authenticity and genuine curiosity. He emphasizes the value of meeting people where they're at, listening to their stories, and sharing something relevant such a good book recommendation.
    Being in sales, Ryan also shares an all-too-often underutilized practice of "closing the loop" with referral partners as well as the importance of personalization and follow-ups. He often leverages LinkedIn and shares his thoughts on how to do cold outreach.
    Overall, the conversation highlights the value of networking as a means of learning, growing, and connecting with others.
    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/

    35 min
  • Episode #15 Risky Business: Uncertain Impact of AI on White-Collar Jobs with Jason Grey

    00:00 The AI Buzz, Why Now?

    03:18 Advancements in AI: From Data Availability to Training Larger Models
    04:27 AI's Impact on Software Engineering Jobs
    09:10 Deterring Computer Science Degrees
    12:36 AI's Acceleration Metric
    15:18 Reducing Headcount, Shrinking Engineering Teams
    19:39 AI Impact On White Collar Professions
    25:51 Distrust in Companies & Self-Governance in AI Usage
    28:36 The Pace of Progress
    31:26 Opportunities to Leverage AI Tools for Skill Enhancement and Income Generation
    Jason Grey, a fervent early adopter of AI and machine learning, knows firsthand the power and mystique surrounding this transformative technology. In this unsettling episode of Cupalo Conversations, Jason confronts the stark reality: AI's impending impact on the job market. Foreshadowing a future where white-collar professions, like software engineering and law, will face a staggering reduction in available jobs.
    A double-edged sword, while AI it enhances efficiency, it also threatens traditional roles. With companies primarily focused on profitability, individuals must cautiously navigate AI's societal implications, self-regulating its usage while preparing for possible disruptions.
    His advice to aspiring computer scientists: don't pursue a degree in Computer Science unless you're ready to specialize in ML and math.
    However, amidst the looming uncertainty, Jason also highlights the potential positives AI brings. Recent advancements, fueled by abundant data and larger models, have propelled AI into unforeseen territories. Tools like ChatGPT exemplify this progress, enabling fluid human-computer interactions. Multimodal models, trained across various data types, promise better understanding and translation capabilities. AI tools offer avenues for skill enhancement and income generation. Jason encourages individuals to embrace continuous learning and adaptability.
    Tune in to gain invaluable insights into the evolving landscape of AI, its implications on the job market, and strategies for navigating its impact on society and individual careers.
    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/

    38 min
  • Episode #14 Unfiltered: A Tech Entrepreneur’s Layoff Survival Guide with Tim Bornholdt

    00:00 Introduction

    01:20 Tim's TEDx Talk
    06:33 The Layoff Journey
    08:33 Anticipating Layoffs and Preparation
    13:19 Losing Confidence After a Layoff
    16:11 The Importance of Networking/Human Connection
    19:53 The Impact of AI and Large Language Models
    23:04 Using AI in the job search
    26:02 Applicability of AI in job search
    27:33 Navigating self-identity and job search
    32:27 The Reality of Being an Entrepreneur & Finding Purpose
    41:06 Saying yes to experiences
    In this episode of Cupalo Conversations, Tim Bornholdt a passionate technologist and seasoned entrepreneur shares raw insights into being laid off and the subsequent job search. Tim's illustrious career includes giving a TEDx talk on AI, founding numerous organizations and crafting apps used by millions including the Great Clips and Little Free Library app. However, despite his impressive track record, he was not immune to the harsh realities of corporate downsizing, finding himself unexpectedly thrust into the chaos of unemployment earlier this year.
    Tim opens up about the profound impact a layoff has on one's sense of self-worth and confidence as well as the pervasive imposter syndrome. Through his candid narrative, Tim unveils the stark truth of the layoff experience, exposing the raw emotions and psychological toll that accompany such upheaval.
    Amidst the darkness, Tim emerges as a beacon of resilience and hope, offering invaluable insights and strategies for navigating the waters of job hunting in the tech industry. He emphasizes the critical importance of human connections in finding both solace and a renewed sense of purpose, urging listeners to seek out meaningful interactions. Furthermore, Tim advocates for the strategic utilization of AI tools to streamline the job search process, sharing practical tips on leveraging technology to enhance efficiency and effectiveness including building and leveraging your own GPT.
    This episode provides a poignant exploration of the trials and tribulations faced by those grappling with unemployment in the digital age. Join us as we uncover the unvarnished truth of Tim Bornholdt's journey, and discover the resilience and fortitude required to weather the storm and emerge stronger on the other side.
    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/

    42 min
  • Episode #13 What's Old Is New Again & the Software Engineering Journey with Dan Chamberlain

    00:00 Getting into Technology

    03:57 Software Engineering & the Corporate Structure

    06:12 Defining Career "Progression" for a Software Engineer

    08:39 Staying in Love with the Craft of Software Engineering

    12:22 Engineering Leaders Keeping Their Hands Dirty

    16:44 Next Generation of Engineers & Overcoming Doom/Gloom

    23:10 Finding Joy in Your Job

    23:39 Know Your Why

    27:29 Advice to a Younger Self

    31:39 Personal and Professional Goals for 2024


    In this episode of Cupalo Conversations engineering leader Dan Chamberlain shares his belief that, when it comes to technology, "what's old is new again." From his early days nerding out on AOL to leading engineering teams at Fortune 500 companies, Dan brings us along his software engineering journey

    A parallel may be drawn between engineers' love for patterns and the very essence of technology itself. Dan reveals that, while the list of technologies grows, the fundamentals are the same. Much like the world around us, tech follows intricate patterns. And despite the ever-evolving landscape, there is comfort in recognizing these patterns.


    Instead of being afraid of what's to come, Dan empowers engineers (and our non-techie listeners) to anticipate trends, adapt swiftly, and embrace the cyclical nature of innovation and the limitless possibilities it presents. Reminding us that "what's old is new again" and everything is going to be all right.


    Connect with Lauren HannonSign 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/



    33 min
  • Episode #12 Career Crossroads: Practical Tips for Navigating Job Transitions with Andrew Altenbach

    00:00 Financial Preparedness for Job Transitions

    08:17 Managing Retirement Accounts
    19:03 Importance of Documentation and Organization
    20:30 Best Practices for Document Storage
    24:30 Other Pragmatic Benefits Coverage to Consider
    26:11 Individual Disability Insurance Coverage
    28:24 The Value of Working with an Advisor
    33:24 The Importance of Education and Listening in Advisor-Client Relationships
    34:11 Remember to Ask Yourself: What Do I Want?
    In episode 12 of the Cupalo Conversations podcast, financial advisor Andrew Altenbach of the Bulfinch Group offers a consoling hand to those navigating turbulent seas of career transitions. Whether it's the thrilling leap from being a full-time employee to an entrepreneur, or the unexpected plunge into the realm of unemployment, Andrew provides listeners with an array of options for navigating these new waters.
    We discuss the pragmatic housekeeping stuff such as what to do with your group benefits including retirement accounts, health insurance, disability, and life insurance. Andrew urges individuals to seek guidance as well as to exercise good document storage practices throughout their careers to make transitions like these easier.
    For anyone navigating the uncharted territories of unemployment or entrepreneurship, you'll emerge from this journey not just unscathed, but empowered to conquer whatever career challenges lie ahead.
    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/

    40 min
  • Episode #11 Flipping the Script: Making FAILURE Your Greatest Asset with Jonathan Leftwich

    02:02 Transitioning from Individual Contributor to Leader

    03:14 The Importance of Mentorship
    04:44 Understanding Failure and Success
    05:58 Risk & Nimbleness: Large Enterprises vs Startups
    07:54 Fear of Failure and Ostracization
    08:41 The Importance of Trust and Teamwork
    09:09 The Value of Networking and Building Relationships
    10:06 Jonathan's Experience with Improv
    12:16 Embracing Vulnerability and Trying New Things
    13:15 Fear of Peer Judgment
    14:57 Taboo Topics in Engineering
    16:16 Creating a Fail-Safe Environment
    18:29 Building Trust and Treating People Well
    19:36 Book Recommendations for Leadership
    20:33 Navigating Performance Improvement Plans
    24:49 Navigating a Layoff
    In the latest episode of Cupalo Conversations, host Lauren Hannon with engineering leader Jonathan Leftwich embrace the hairy/scary topic of failure and its indispensable role in achieving success.
    Drawing from his diverse experiences in professional powerlifting, stand-up comedy, and transitioning into engineering leadership roles, Jonathan emphasizes the pivotal lesson: one must be willing to fail in order to ultimately succeed.
    You're human. You're going to make mistakes. Put the ego aside and learn from the mistake. Learn from those around you. And move on to bigger and better things.
    This is important both within the context of work and without. Jonathan advocates for a mindset that welcomes vulnerability and is unafraid of looking foolish in pursuit of progress. This is often achieved by trusting in one's tribe. Jonathan emphasizes the significance of surrounding oneself with a supportive community that encourages resilience and offers assistance during setbacks.
    This episode of Cupalo Conversations serves as an inspiring reminder of the transformative power of failure. By reframing failure as an essential stepping stone towards success, listeners are encouraged to adopt a mindset of resilience, accountability, and unwavering trust in their journey towards personal and professional fulfillment.
    Connect with Lauren Hannon
    Sign up for "Cupalo Newsletter" (Lauren's email newsletter): https://cupalo.substack.com/
    Follow Lauren on LinkedIn: https://www.linkedin.com/in/hannonlauren/
    Check out Cupalo's website: https://cupalo.io/

    31 min
  • Episode #10 Time to Call Your Lawyer: Navigating Attorney Engagement & Negotiations with Cody Blades

    01:22 Attorneys for Everyone

    02:01 Contingency Based Arrangement
    04:10 Retainer Fee Structure
    06:01 Different Fee Arrangements
    07:42 How to Find the Right Attorney
    11:23 Negotiating with Your Attorney
    14:18 Understanding Employment Contracts
    15:42 Negotiating Your Employment Contract
    19:46 Negotiating After Leaving Employment
    20:42 Getting Help with Legal Matters
    25:04 Setting Up a Business or Side Hustle
    26:46 Protecting Personal Assets and Avoiding Co-mingling of Funds
    28:46 The Importance of Operating Agreements
    33:43 Fractional General Counsel and Assistant General Counsel
    38:19 Building a Personal Brand and Business Development
    In this episode of Cupalo Conversations, attorney Cody Blades delves into numerous unspoken aspects of working with attorneys and crucial yet frequently overlooked elements of legal counsel.
    Demystifying hourly rates, contingency fees, retainer agreements, flat fees as well as various engagement models, Cody empowers listeners to feel confident negotiating with their legal counsel. Cody shares practical tips and strategies for effectively communicating with legal representatives, advocating for one's interests, and achieving mutually beneficial outcomes.
    Delving into common pitfalls both employees and business owners make, from overlooking critical clauses in contracts to neglecting the importance of shareholder agreements, Cody offers actionable advice for employees AND entrepreneurs looking to navigate the legal landscape with confidence.
    Whether you're an employee negotiating a contract or a business owner navigating a lawsuit, this episode equips you with the knowledge and tools to navigate the attorney-client relationships with confidence and clarity. 🏛
    Connect with Lauren Hannon
    Sign up for "Cupalo Newsletter" (Lauren's email newsletter): https://cupalo.substack.com/
    Follow Lauren on LinkedIn: https://www.linkedin.com/in/hannonlauren/
    Check out Cupalo's website: https://cupalo.io/

    35 min
  • Episode #9 In the Mind of the Beholder: Brand, Beyond the Logo with Leigh Nunn

    00:48 What is a brand?

    04:25 The challenge of defining brand
    05:52 Understanding customers
    06:33 Intersection of brand and values
    09:28 Researching target audience
    10:58 Building the Cupalo brand
    14:25 Shift towards personal branding
    17:11 Building a Personal Brand
    18:11 Infusing personality into a brand
    22:38 Differentiating personal brand from marketing
    24:04 Navigating the pressure of self-promotion
    24:45 Authenticity and Self-Promotion
    27:29 Trial and Error in Content Creation
    29:42 Being the Guide vs. the Hero
    In this episode of Cupalo Conversations, Leigh Nunn, founder of Brandish, a brand and marketing services company, delves into the intricate concept of branding, exploring both corporate and personal branding dynamics.
    Leigh emphasizes that a brand extends beyond mere visual identifiers like logos or color schemes. Instead, it encapsulates the nuanced feelings and perceptions that customers associate with a business or individual. While businesses can influence these perceptions, the ultimate construction of a brand occurs within the minds of the audience.
    Grounded in the principle that "nobody cares about what you do. They care about what you can do for them," Leigh introduces the hero plot structure to illustrate this concept. Using the archetype of Luke Skywalker and Obi-Wan Kenobi from Star Wars, he elucidates how customers should be positioned as the heroes in their own narratives, with the brand assuming the role of the guiding mentor.
    In the context of branding and marketing, Leigh underscores the importance of aligning the brand's offerings with the customer's needs and desires. By adopting the role of the guide, businesses can effectively assist customers in navigating their journey, overcoming obstacles, and achieving their desired outcomes.
    Overall, this episode offers profound insights into branding strategies, authentic storytelling techniques, and the pivotal role of customer-centric approaches in building enduring and successful brands.
    Connect with Lauren Hannon
    Sign up for "Cupalo Newsletter" (Lauren's email newsletter): https://cupalo.substack.com/
    Follow Lauren on LinkedIn: https://www.linkedin.com/in/hannonlauren/
    Check out Cupalo's website: https://cupalo.io/

    35 min
  • Episode #8 Culture Unveiled: Decoding Taboo Topics in Corporate America

    00:00 New Chapter

    00:40 What is Culture?
    02:21 The Evolution of Culture in Corporate America
    06:58 Different Experiences of Company Culture
    09:05 Respecting Different Skill Sets
    11:29 The Role of Core Values in Culture
    13:36 Balancing Culture and Compensation
    18:20 Compensation Discrepancies
    21:58 Belonging and the Challenges of Hybrid Work Models
    22:40 Hybrid Work Models and Culture
    28:06 Focus for 2024: Service and Culture
    31:29 Layoffs Are Not The Answer
    34:20 The Importance of How Leaders Show Up
    35:06 Conclusion and Gratitude
    In this eye-opening episode of Cupalo Conversations, Patrick Bergstrom the CTO & Co-Founder of CultureKey brings the misunderstood yet crucial topic of culture into the foreground and exposes some of the critical flaws observed in Corporate America.
    Patrick highlights the detrimental consequences of neglecting or failing to uphold a strong organizational culture. How short-sighted cost-cutting measures, such as layoffs and inequitable compensation, undermine long-term vision and harm innovation, productivity, and ultimately profitability.
    Throughout the conversation, Patrick advocates for a culture-first approach, emphasizing the need for companies to prioritize people over profits. By fostering a culture that values open dialogue and transparency between employees and leaders, especially on the topics of compensation and variable work arrangements, organizations not only create a psychological safe work environment but can ultimately achieve greater success in the long run.
    Join Lauren and Patrick as they explore the transformative power of prioritizing culture in driving positive change within Corporate America, ultimately paving the way for greater employee satisfaction, engagement, and retention. And therefore, greater innovation, productivity, and profitability.
    Connect with Lauren Hannon
    Sign up for "Cupalo Newsletter" (Lauren's email newsletter): https://cupalo.substack.com/
    Follow Lauren on LinkedIn: https://www.linkedin.com/in/hannonlauren/
    Check out Cupalo's website: https://cupalo.io/

    35 min
  • Episode #7 Embracing Fractional Leadership in Tech: Insights from Fractional CTO Guillermo Fisher

    00:00 Intro

    00:58 Journey Into Consulting
    04:27 Working with Start Up Clients
    04:57 Fractional Work: Part Time or Full Time Commitment
    07:02 Market Readiness For Fractional Tech Leadership
    11:16 Advice for Aspiring Fractional Leaders
    15:06 Unexpected Benefits to Fractional Consulting
    23:54 Closing Remarks
    In this episode of Cupalo Conversations, host Lauren Hannon discusses Fractional Tech Leadership with Guillermo Fisher, the founder of Kuzaa and a seasoned professional with over two decades building high-performing dev teams and resilient cloud architectures.
    Throughout the discussion, Guillermo shares invaluable insights from his recent journey from full-time employee to solo entrepreneur and fractional CTO. He candidly offers advice for aspiring fractional leaders, emphasizing the importance of committing full-time to the role and being prepared for the initial financial challenges. He shares his perspective on how fractional leaders bring unique expertise and experience to the table, benefiting companies at various stages of growth.
    Moreover, Guillermo and Lauren delve into the market's readiness to embrace fractional tech leadership. He provides compelling insights into the benefits of fractional leaders and how they contribute to the success of organizations. He discusses the evolving landscape of tech leadership and the potential for further acceptance and adoption of fractional roles in the market.
    Overall, this episode provides a deep dive into the world of fractional tech leadership with something worthwhile for both aspiring fractional tech leaders and organizations seeking to leverage fractional expertise.
    Connect with Lauren Hannon
    Sign up for "Cupalo Newsletter" (Lauren's email newsletter): https://cupalo.substack.com/
    Follow Lauren on LinkedIn: https://www.linkedin.com/in/hannonlauren/
    Check out Cupalo's website: https://cupalo.io/

    26 min

About Cupalo Conversations

From the publisher's feed

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…