
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

Jul 3, 2024 • 40min
Episode #26 The Human-AI Duo: Job Searching Reimagined with Pranay Joshi of Skip Round
00:00 Introduction and Inception of Skip Round
02:33 The Broken Job Search Process
05:03 Resume Limitations & Resume Etiquette
07:58 AI Coach for Interview Preparation
11:07 Human Psychology and the Job Search Process
13:32 The NAIL Framework for Successful Job Searching
16:30 The Importance of Goal Setting & Continuous Introspection
21:10 Career vs. Job: Serving a Purpose
24:35 Acres of Diamonds & Self Awareness
27:09 Downsides of Using LinkedIn for Job Searching
29:14 Taking Control of Social Media Platforms
30:29 Magic of Contributing to LinkedIn32:52 Challenges of Being a Solopreneuer & the Generosity of Others
35:13 Challenges and Support of Being a Solo Founder
35:56 The Importance of Human Connection
In this insightful episode of Cupalo Conversations, host Lauren Hannon sits down with Pranay Joshi, the visionary founder of Skip Round. The episode delves into the innovative solutions Skip Round offers to job seekers, aiming to revolutionize the job application and interview preparation process.
From crafting custom resumes and cover letters to providing an AI-powered coach for interview preparation, Skip Round equips users with the essential tools to succeed.
Pranay discusses the flaws in the current job search process and how Skip Round aims to address these issues. He emphasizes the need for adaptability and storytelling in interviews and points out the limitations of traditional resumes.
Pranay introduces the Nail Framework, which focuses on Networking, Introspection, Learning, and Applying. This holistic approach to job searching encourages job seekers to build connections, understand themselves better, continuously learn, and apply their knowledge effectively. The conversation delves into the psychological aspects of job searching, emphasizing the importance of goal setting and introspection. Pranay shares how Skip Round incorporates AI to provide interview practice and prompts for introspection, helping users prepare mentally and emotionally for their job search.
The episode concludes with a discussion on the power of human connection. Pranay talks about his mission to make the world feel smaller and sweeter by helping people find jobs they love and connecting them with opportunities that resonate with their purpose.
Pranay shares his inspiring vision of a utopian world where everyone loves their job. He believes that when people are passionate about their work, they are more productive and fulfilled. Skip Round, according to Pranay, is the first tangible step towards achieving this vision by empowering job seekers to find roles they are genuinely excited about.
This episode is a must-listen for anyone in the job market or those interested in the future of job search technologies. Pranay Joshi's passion for helping people find their ideal careers shines through, making this an engaging and motivational conversation.
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/

Jun 27, 2024 • 32min
Episode #25 In Sickness & In Health: Financial Preparedness & Emotional Resilience with Ullas Perez
00:00 Journey from Engineering to Motivational Speaking
05:40 Navigating Health Challenges and Financial Preparedness
11:30 Stigma & Shame Around Having a Disability
14:26 The Power of Your Subconscious Mind
22:13 Making Money & Building Wealth Are Different Skill Sets
23:31 Making Peace with Negative Thoughts
26:15 Ullas's Definition of Wealth: Happiness, Health, and Money
28:31 To All Women Listeners: Be Better Stewards of Your Money
In this enlightening and very candid episode of the Cupalo Conversation podcast, host Lauren Hannon sits down with Ullas Perez, a seasoned technology leader with a remarkable career journey. From leading engineering teams and boasting an impactful seven-year tenure at The Boeing Company, the discussion takes a poignant turn as Ullas opens up about the unexpected health crisis that derailed her career.
After coming into contact with black mold, Ullas suffered from chronic health issues that ultimately forced her to leave the workforce. Despite this challenging setback, Ullas and her husband were financially prepared, thanks to her disability insurance coverage, which helped them navigate the financial turmoil.
Throughout the episode, Ullas emphasizes the importance of financial and emotional preparedness in facing life's harsh realities, such as job loss, income loss, sickness, and death.
She passionately discusses her mission to help others create a life of abundance and purpose through motivational speaking and financial education. By sharing her personal experiences and insights, Ullas aims to empower listeners to proactively plan for uncertainties and build resilience in the face of adversity.
Tune in to this episode for a heartfelt conversation that blends personal storytelling with practical advice on navigating the unpredictable challenges of life.
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/

Jun 20, 2024 • 39min
Episode #24 Cross-Cultural Synergies in Tech & Nearshore Staff Augmentation with Mateo Bervejillo
00:00 Mateo's Journey from Law to Outsourcing
09:14 The Main Pain Points for Leaders in Technology
11:57 Advantages of a Near Shore Staffing Model
13:45 Thriving Tech Scene in Latin America
18:24 Correlation Between US Economy & Latin American Talent
23:02 Compensation Discrepancy Between Onshore & Offshore Talent
25:35 Behind the Scenes: Staff Augmentation Sales Role
33:03 Professionalism & Innovation at Xseed
In this engaging episode of Cupalo Conversations, Lauren Hannon talks shop with Mateo Bervejillo, the CEO of Xseed Solutions, to explore the burgeoning field of nearshore staff augmentation and its impact on the tech industry. Xseed Solutions is known for providing top-tier Latin American talent, and Mateo shares his insights on why this region has become a hotspot for tech talent.
Mateo explains the advantages of nearshore staff augmentation, particularly for U.S. companies looking to scale efficiently. He highlights how this model offers not only cost benefits but also significant reductions in time zone and cultural barriers. Mateo emphasizes how shared values and business practices foster better collaboration and integration between teams from these regions.
The conversation delves into the rapid growth of the tech industry in Latin America. Mateo discusses how countries like Mexico, Brazil, and Argentina have become key players in the global tech market, with a robust pipeline of skilled professionals.
Throughout the episode, Mateo Bervejillo provides valuable insights into the strategic advantages of leveraging Latin American talent for tech projects. He underscores the importance of geographic proximity, cultural closeness, and the interconnectedness of the economies in fostering a successful collaboration between the U.S. and Latin America.
This episode is a must-listen for anyone interested in understanding the dynamics of nearshore staff augmentation and the significant role that Latin American talent plays in the global tech ecosystem.
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/

Jun 13, 2024 • 36min
Episode #23 Demystifying the Path to Big Tech: Insights From a 3x FAANG Engineer with Andy Wong
00:00 Journey into Software Engineering
05:18 Coding Bootcamps Hot Take
10:04 FAANG Interview Process
14:30 Smaller Orgs Idolatry of FANNG Companies Dispelled
18:05 Are FAANG Engineers Really That Much Better?
25:57 The Role of Luck in A Successful Career
30:11 Andy's Advice For Those Seeking an Influencer's Advice
In this episode of Cupalo Conversations, host Lauren Hannon pulls back the curtain a little on the world of big tech with three-time FAANG engineer, Andy Wong. Despite his impressive software engineering career at Google, Amazon, and Meta/Facebook, what sets Andy apart is his unconventional background. As an English and Psychology major who transitioned into tech through a coding bootcamp, Andy offers a refreshing perspective on achieving success in the industry without a traditional Computer Science degree.
Andy humbly attributes much of his journey to luck and being in the right place at the right time, debunking the myth of overnight success. He shares invaluable insights on how to prepare for FAANG interviews, emphasizing the importance of leveraging online resources and staying persistent.
One of the most surprising revelations from Andy is the mutual admiration between startups and big tech organizations. While startups often idolize big tech, Andy reveals that the reverse is also true, shedding light on the symbiotic relationship between these entities.
Throughout the conversation, Andy demystifies the aura surrounding big tech, offering a refreshingly human perspective on what it's like to work in these renowned organizations. His circuitous journey from liberal arts to tech is not only inspiring but also a testament to the diverse paths one can take to achieve success in the industry.
Tune in to Cupalo Conversations for an insightful and approachable exploration of the FAANG world with Andy Wong.
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/

Jun 6, 2024 • 39min
Episode #22 In Defense of Culture: Preserving Authenticity in an Algorithmic Era with Ben Wise
00:00 Introduction to Ghostwriting as a Career
07:03 In Ghostwriting Who Is the Author?
09:53 Adopting Another's Voice and SME
16:00 A LinkedIn Ghostwriter's Critique of LinkedIn
18:03 The Opaque and Ever-Changing Algorithm of LinkedIn
19:45 LinkedIn as a Tool, Not the End Goal
24:25 The Line Between Vulnerability & Oversharing on Social Media
30:38 Luck, an Essential Ingredient to Success in Business
32:57 Successful Marketing for Founders
In this episode of Cupalo Conversations, Lauren Hannon interviews Ben Wise the founder of Storyd a US-based ghostwriting studio that helps 7+ figure founders turn their expertise and stories into compelling LinkedIn content in as little as two hours a month.
Ben shocks audiences with the admission that, despite being a highly successful LinkedIn ghostwriter, he wouldn't be on LinkedIn (or any social media) if he didn't have to.
Social media platforms such as LinkedIn incentivize users to conform to algorithmically favorable personas, prioritizing superficial posts and contributions at the expense of true self-expression, high quality content, and meaningful interactions. Ben also calls attention to the platform's opaque and ever-changing algorithms as a source of frustration and disillusionment.
Ben shares insights from his own journey navigating these platforms, from his initial foray into content creation on Quora and Upwork to founding his own ghostwriting business, Storyd. Throughout the episode, Ben emphasizes the importance of building trust with one's audience and staying true to oneself, even in the face of digital media pressures. He advocates for a marketing approach grounded in authenticity and customer satisfaction, rather than chasing fleeting success.
Listeners will come away with a deeper understanding of the challenges posed by algorithm-driven platforms like LinkedIn and a renewed appreciation for the power of authentic storytelling in building meaningful connections both online and offline.
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/

May 30, 2024 • 39min
Episode #21 The Art of the Job Search: How to Achieve a Career Nirvana with Katie McIntyre
00:00 Katie's Journey: Holding Down 8 Jobs and Making $1 Million a Year
04:08 The Importance of Introspection in the Job Search Process
05:53 No Such Thing as a "Dream Job"
10:09 The Key to Effective Resumes & the Importance of Networking / Outreach
17:34 Interview Practice & Dealing with Interview Rejection
26:59 How to Approach the Salary Negotiation Process
33:27 2024 Tech Job Market Conditions & the Power of Human Connections
In this 21st episode of Cupalo Conversations, Lauren Hannon sits down with High Performance Coach Katie McIntyre from CareerSprout, who has helped countless individuals secure coveted $200k to $500k+ job offers at companies they admire and doing work they genuinely enjoy.
The conversation delves deep into the multifaceted job search process, offering invaluable advice on crafting resumes that stand out, moving beyond the limitations of Easy Apply, eliciting responses through targeted outreach, honing interviewing as a new skill, and navigating complex salary negotiations. Katie challenges the conventional approach to job seeking, urging listeners to prioritize envisioning the life they desire over fixating solely on job titles or what someone else is doing.
Listeners gain insights into positioning themselves effectively for networking meetings and interviews, emphasizing the importance of authenticity over perfection.
Katie highlights the significant distinction between excelling at one's job and mastering the art of interviewing, stressing the need for practice and continuous refinement. Moreover, Katie shares invaluable strategies for interview preparation and communication, advocating for a consultative and approachable demeanor rather than a know-it-all attitude. She underscores the significance of expressing gratitude when receiving offers, asserting that a well-executed job search strategy should render negotiation unnecessary.
Throughout the episode, Katie offers practical tips on honing interview skills, reframing job search approaches, and achieving what she terms "job nirvana" – the ideal alignment of professional fulfillment and personal satisfaction. Tune in to uncover the secrets to navigating the competitive landscape of high-paying dream jobs with confidence and authenticity.
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/

May 23, 2024 • 40min
Episode #20 Making Fire with Your Hands: Sales as a Life Skill with Mickeli Bedore
04:24 Sales as a Life Skill
10:41 Prospecting: Know Your Customer
15:35 Hierarchy of Purpose in Sales
18:52 Rapid Revenue Growth Consulting
29:24 Making Fire with Your Hands
33:35 To Entrepreneur Or To Not Entrepreneur. That is the Question.
In this episode of Cupalo Conversations Mickeli Bedore a former top sales performer for IBM, Oracle, & Verizon and 5x start up founder shares his journey into sales and emphasizes the importance of sales as a life skill. Mickeli emphasizes the importance of cultivating great communication skills and constantly practicing sales, just like any other sport or discipline. It's not something you're just born with and can set it and forget it.
He discusses the misconceptions and stigma surrounding sales and explains the mindset and approach to successful prospecting. He also highlights the significance of prioritizing your own needs and the needs of the customer over the product or service being sold.
The conversation explores the concept of making fire with your hands, which means being able to support yourself without depending on someone else. As a serial entrepreneur, Mickeli advises listeners to follow their calling which may be a 9to5 job, investing, or business ownership.
Tune in to learn more about the art and science of selling as well as what it means to make fire with your hands.
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/

May 16, 2024 • 32min
Episode #19 Your Online Impact: A Guide to Social Media Success with Diana Bagas
01:05 Launching "Launch" a Social Media Business
03:07 The Challenges of Social Media for Business Owners
06:23 How to Grow an Audience on Social Media & Leverage Paid Advertising
12:02 Choosing the Right Social Media Platforms for Your Business
16:42 Leveraging Personal and Company Pages on LinkedIn
18:20 The Importance of Consistency in Social Media
23:22 Cultivating a Brand Voice
25:55 Misconceptions About Social Media
27:36 Looking Ahead and Exciting Opportunities
In this episode of Cupalo Conversations social media guru Diana Bagas, the innovative mind behind Launch Social Media, emphasizes the transformative potential of social media for individuals and businesses alike. Focused on harnessing the power of social media for business growth, personal branding, career advancement, and network expansion.
Diana shares invaluable insights tailored for both business owners and professionals eager to make their mark in the digital sphere. She encourages businesses to leverage the highly impactful (and low cost) paid advertisements on platforms like LinkedIn, Facebook, and Instagram. She highlights the importance of leveraging LinkedIn to level up in your career, get that promotion or that new job, by sharing meaningful content and becoming known as a valuable contributor in the marketplace.
While hiring a social media expert is an option (just give Launch Social Media a holla), Diana encourages listeners to seize control of their online presence and master the art of making a significant impact in the digital landscape.
Tune in to discover how to take the reins of your social media journey and make waves in your industry.
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/

May 9, 2024 • 38min
Episode #18 Beyond the Gridiron:Life After the NFL with Brandon Archer
00:00 Brandon's Introduction to Football
05:03 Brandon's Career Highlights
09:33 Transitioning Out of Football into the "Real World"
12:47 Challenges Faced by Professional Athletes After the Game Ends
17:29 Transferring of Skills: From Sports Arena to Business World
24:38 Passion Projects: The Importance of Having a Hobby
28:13 Common Misconceptions About Professional Athletes
35:09 Goals for the Future: Sales and Marketing, YouTube, and Business Acquisition
In episode 18 of Cupalo Conversations, host Lauren Hannon sits down with her dear friend Brandon Archer, who brings a unique perspective as a former professional football player turned sales expert. Brandon's journey took him from the gridiron with the Indianapolis Colts, Denver Broncos, and the Rhinos Milano in Italy, to a successful career in IT Solutions sales, and now as the Director of Sales and Marketing at Kasota Stone.
The conversation delves into the challenges that often accompany the transition from professional sports to the corporate world. Brandon shares insights into the physical toll of the game, financial adjustments, and the identity shift that occurs when no longer being defined solely as a football player. Despite these hurdles, Brandon's resilience shines through as he emphasizes the importance of adaptability, competitiveness, and courage in both athletics and business.
Beyond his professional endeavors, Brandon reveals his passion for remote control airplanes, highlighting the significance of having a fulfilling hobby outside of work. He also addresses common misconceptions about professional athletes, shedding light on the realities of their physical and mental health struggles.
Looking ahead, Brandon discusses his aspirations for the future, which include excelling in his current role and venturing into the world of content creation with a YouTube channel focused on remote control hobbies.
Overall, episode 18 offers a captivating glimpse into the multifaceted journey of Brandon Archer, showcasing his unwavering determination and passion for both sports and business.
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/

May 2, 2024 • 34min
Episode #17 Managerial Maze: Why Managers Need Guidance Now More Than Ever with Alison Gretz
03:24 Transitioning from Craftsman to Manager
06:23 Investing in Better Frameworks and Tools for Leadership
08:42 Choosing the Right Path: Manager or Individual Contributor
12:28 Supporting Individuals Who Choose Not to Pursue Management
18:14 New Manager Challenges
20:45 Cultivating Self-Confidence
24:52 Leaders Want To Be Led
27:05 How Leaders Create A Psychologically Safe Workplace
31:00 2024 Goals and Aspirations
In this episode of Cupalo Conversations, we delve into the intricacies of leadership transitions with guest, Alison Gretz. Alison brings a wealth of experience from her diverse career spanning leadership roles in User Experience, creative, content design, and product design teams at both start-ups and Fortune 100 companies.
Alison discusses the common challenges individuals face when transitioning into management roles for the first time and the ones they face as they continue climbing the ladder. She emphasizes the lack of adequate support and preparation often provided to new managers, leading to feelings of isolation and imposter syndrome.
Furthermore, Alison addresses the pressure placed on craftsmen such as in design and software engineering roles to ascend into people leadership positions, despite their preference for remaining hands-on with their craft.
Drawing from her extensive background, Alison shares insights into alternative career paths for those who are not inclined towards traditional people management roles. She advocates for recognizing and valuing individual strengths, emphasizing the importance of allowing professionals to excel in their areas of expertise without imposing rigid career trajectories.
Alison also discusses her perspective on what makes a great leader, highlighting the importance of creating psychologically safe environments where individuals feel free to express their opinions openly. Feedback given and received as the bedrock of a great working dynamic.
Throughout the episode, Alison emphasizes the significance of mentorship, continuous learning, and self-awareness in navigating leadership transitions successfully. She encourages organizations to foster supportive environments that empower individuals to thrive in roles aligned with their passions and strengths.
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/