Two Coffees In

About Two Coffees In

Two Coffees In is the anti-hustle podcast for seasoned professionals navigating layoffs, burnout, and career reinvention in the age of AI. Hosted by Ashok & Lu—two ex-colleagues who gave their all to corporate—we bring you honest conversations about what work really looks like today. No frameworks. Just real talk over coffee.

Publisher

Ashok Venkatraj & Luciana Madeira

Category

business

Language

en

Explicit

No

First episode

9 Mar 2026

Latest episode

3 Sept 2026

Latest episodes

9 episodes in the feed.

1. 

   3 Sept 2026

   Is Coaching Worth It ? A Real Convo with Executive Coach Lisa

   Is coaching worth it—or is it just another career expense that sounds good in theory? In this episode of Two Coffees In, Luciana and Ashok sit down with executive coach and leadership-development expert Lisa Graham, to get an honest answer. Lisa spent years as a senior HR leader before founding Lisa Graham Coaching, LLC, where she helps emerging and experienced leaders move past the patterns that keep them stuck. Together, they unpack what coaching actually is—and what it is not—while separating it from therapy, consulting, and simply having a supportive friend. They also explore the real challenges showing up in today’s workforce: burnout versus exhaustion, career uncertainty, layoffs, AI anxiety, remote-work whiplash, and the “fine but unfulfilled” feeling that keeps many high performers in place. Lisa shares who gets the most from coaching, how to know whether a coach is the right fit, when coaching does not work, and what to do if formal coaching is not accessible right now. If you are good at your job but unsure what comes next, this conversation may give you the question—or the push—you need to move forward.

2. 

   15 Jul 2026

   Rethinking Education and Preparing Kids for the Future in the Age of AI

   Title: Rethinking Education and Preparing Kids for the Future in the Age of AI Key takeaways: AI is changing the future of work faster than traditional education can adapt. Critical thinking, curiosity, and communication matter more than degrees alone. Real-world skills and interdisciplinary learning are becoming more valuable. Parents should focus on helping kids learn how to think, reflect, and adapt. Social media, COVID, and AI have reshaped how young people learn and connect. Humility, focus, and self-directed learning will be key future skills. Clear problem-solving and strong communication are essential in an AI-driven world. Connect with Ravi Manikundalam @ https://www.linkedin.com/in/ravimanikundalam/ (https://www.linkedin.com/in/ravimanikundalam/) Ashok Venkatraj @ https://www.linkedin.com/in/ashokvenkatraj/ (https://www.linkedin.com/in/ashokvenkatraj/) Luciana Madeira @ https://www.linkedin.com/in/lucianamadeira/ (https://www.linkedin.com/in/lucianamadeira/)

3. 

   2 Jun 2026

   From CTO to Business Owner With James Jean

   From quitting a comfortable IBM job to living in a 296-square-foot RV and running both a digital agency and a fencing company, James Jean has rebuilt work and life from the ground up. In this episode of Two Coffees In, Ashok and Luciana dig into why he chose to “AI-proof” his career, how his faith shapes his refusal to use generative AI, and what it takes to juggle a creative tech shop and a 50/50 family fence business with his son. If you’ve ever heard that “get out” voice about corporate life, this conversation gives a candid look at the risks, tradeoffs, and freedom on the other side. Connect with us: Ashok Venkatraj: linkedin.com/in/ashokvenkatraj (http://linkedin.com/in/ashokvenkatraj) Luciana Madeira: linkedin.com/in/lucianamadeira (http://linkedin.com/in/lucianamadeira) James Jean @ https://goodneighborsfenceco.com/ (https://goodneighborsfenceco.com/)

4. 

   19 May 2026

   Tech Support by Day, Jokes by Night - With Comedian Kazeem

   What does it actually look like to hold 3 identities—IT professional, standup comedian, dad—without collapsing any of them? In this episode, Ashok and Lu sit down with Kazeem Rahman (KazeemComedy) to find out. Kazeem's path wasn't linear: pre-pharmacy at UT, an accidental pivot into IT, years of writing jokes on the side before finally committing to standup. He talks about why he mines his own perspective instead of his helpdesk queue, what years of bombing at open mics taught him about communication and pressure, and why the Houston–Austin late-night circuit was its own kind of MBA. We get into what shifts when you become a parent, why some comics double down while others quietly exit, and how to navigate a creative life when your partner comes from a more traditional "degree–job–paycheck" world. No "quit your job and follow your passion" advice here. Just a more honest frame: treat your creative work as a core part of staying functional—not a luxury you'll get to someday. Connect with us: Ashok: linkedin.com/in/ashokvenkatraj (http://linkedin.com/in/ashokvenkatraj) Lu: linkedin.com/in/lucianamadeira (http://linkedin.com/in/lucianamadeira) Kazeem: youtube.com/@KazeemComedy (http://youtube.com/@KazeemComedy)

5. 

   11 May 2026

   Spot Fake Company Culture Before It's Too Late

   When a company tells you “we’re a family,” is that a green flag or the start of a slow-motion nightmare? In this episode of Two Coffees In, Ashok Venkatraj and Luciana “Lu” Madeira sit down with Dr. Amber Selking, Chief Leadership & Culture Development Officer at Lippert, to talk about how to spot fake company culture before you sign the offer and rearrange your whole life around the wrong job. Drawing on Amber’s experience leading culture and leadership transformations across global teams and high-pressure environments, they unpack: The difference between “performative” culture and the real thing when you’re on the outside looking in The red flags and green flags job seekers should look for in interviews, all-hands meetings, and leadership comms How broken cultures spill over into your family, health, and long-term career options Practical questions you can ask to test whether leaders live their values or just talk about them If you’re interviewing, quietly open to new roles, or trying to fix culture from the inside, this conversation gives you a grounded BS detector. Connect with us on LinkedIn: Ashok Venkatraj – Host, product & AI builder, co-creator of Two Coffees In: linkedin.com/in/ashokvenkatraj (http://linkedin.com/in/ashokvenkatraj) Luciana (Lu) Madeira, MBA – Host, senior IT and transformation leader at Lippert: linkedin.com/in/lucianamadeira (http://linkedin.com/in/lucianamadeira) Dr. Amber Selking – Founder, Selking Performance Group & Chief Leadership & Culture Development Officer at Lippert: linkedin.com/in/amberlattner (http://linkedin.com/in/amberlattner) For informational purposes only - Not professional advice.

6. 

   28 Apr 2026

   Is AI Causing Brain Rot?

   I used AI to write some emails. When I reread them later, something felt off. The words were right. The voice wasn't mine. That moment made me ask a question I'd been avoiding: is AI actually making me better at thinking — or am I just getting better at outsourcing it? This week, Lu and I sat down with no guest, no agenda, and no easy answers. Just an honest conversation about where AI has genuinely sharpened us — and where it's quietly taken something we didn't realize we were giving away. Focus. Judgment. The thinking muscle that only activates when you can't tap out. We're calling it AI brain rot. Not the meme. The version that creeps up on you. If you've ever reached for the prompt before you even tried — this episode is for you.

7. 

   7 Apr 2026

   Retiring Abroad : Worth giving up your Costco Card?

   Most "retire abroad" conversations skip the part where things get weird — healthcare paperwork, school enrollment in a language you're still learning, the moment you realize Costco won't be there in your new country. In this episode, Ashok and Lu sit down with Kartheek Hirode, a former Fortune 100 IT Director who walked away from corporate life and moved his family to Provence, France — few months ago. Not as a trial run. As the plan. We get into the real numbers: what healthcare actually costs, how he built a visa and tax strategy without losing his mind, and what surprised him most after the move that no spreadsheet flagged. Kartheek also opens up about how he decided he had "enough" — financially and mentally — and what he genuinely misses about the U.S. (it's not what you'd expect). No buzzwords. No fantasy. Just a grounded, honest conversation with someone people dream of achieving. TL;DR Guest Kartheek Hirode — recently retired Fortune 100 IT Director, now living in Provence, France with his family. What you'll learn How to calculate your real financial runway before making the move — including healthcare, taxes, and what savings actually buys you abroad. How to research the visa and residency requirement for any country on your list. How to evaluate schools, social life, and day-to-day friction when you're moving with kids — not just with a backpack. The mental shift required to stop optimizing for salary and start designing for time / autonomy — and how Kartheek made that call. First steps How to run an honest "enough" number for your own situation — and where to start research if you're seriously considering it.

8. 

   23 Mar 2026

   50 & Fired!

   “50 & Fired” goes inside what it’s really like to be restructured out of a senior role at 50—and what you do the week after the call. Ashok and Lu talk with executive leader Shay Tower about losing identity, status, and structure overnight, the black hole of LinkedIn, and the “cobwebs” metaphor from her coach that helped her move through fear instead of freezing. Shay Tower (https://www.linkedin.com/in/shay-tower-pmp/)is a seasoned program management leader who currently runs the IT Project Management Office at Austin Community College and previously led major global digital portfolios at General Motors, where she and Ashok first worked together. She brings deep experience turning strategy into execution, building high-performing teams, and guiding organizations through digital and cultural transformation. Now she’s using all of that to design a second act built on purpose, impact, and autonomy after a late-career layoff—showing that while a company can end your job, they don’t get to decide what you do next.

9. 

   9 Mar 2026

   No Time For Meditation & other Excuses we tell ourselves!

   No Time For Meditation (& Other Excuses We Tell Ourselves) dives into the lies we tell ourselves about why we “can’t” slow down, be still, or take care of our own minds. From “I’m too busy” to “my brain just doesn’t shut off,” we unpack the real reasons behind these excuses and how they keep us stuck on the productivity hamster wheel. In this episode, Selva, Lu & Ashok share practical, no-fluff ways to bring micro-moments of calm into real life—between meetings, after kids drop-off, or during that first sip of coffee — without needing a cushion, an app, or a 60-minute routine. If you’ve ever said “I know I should meditate” but never actually start, this one’s your gentle (and slightly uncomfortable) wake-up call. Our guest, Selva Kumaraswamy is a seasoned technology entrepreneur with over 25 years in the industry, having served as founding principal of a consulting practice, CEO of an early-stage startup, and CTO across multiple ventures. He is currently Co-Founder and CTO of Hawcx, a funded cybersecurity startup, and has spent more than two decades studying and practicing meditation and breath-work. With over 1,000 hours of formal meditation teacher training, he leads resilience and mindfulness workshops that blend ancient wisdom with modern professional life, bringing a unique lens on leadership at the intersection of innovation, mindfulness, and human performance.[riverside] Selva Kumaraswamy – Co-Founder & CTO, Hawcx (featured in TechCrunch) · selva@hawcx.com (mailto:selva@hawcx.com)

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

2 ratings

Spotify

5.0 / 5

1 ratings

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Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.