From CTO to Business Owner With James Jean

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/]

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]

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.

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.

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.