The Cyber Boss Show™

What does it really take to build a career, stay competitive, and create access in today’s cybersecurity industry?

In Episode 25 of The Cyber Boss Show™, Dr. Ree sits down with Oluwadamilola Obamehinti, Founder & CEO of Cyber Culture®, for the first guest conversation of Season 3. Oluwadamilola shares her journey from cybersecurity professional and executive to entrepreneur, founder, speaker, and thought leader including the parts of building a business that technical expertise alone doesn’t prepare you for.

Together, Dr. Ree and Oluwadamilola unpack access and gatekeeping in cybersecurity, the hidden job market, representation in leadership, and why qualified professionals can still struggle to get opportunities in an industry that continues to talk about a talent shortage.

They also explore how AI is accelerating the pace of learning, why experience alone is no longer enough to stay competitive, the growing importance of thought leadership, and how cybersecurity professionals can begin turning their expertise into opportunities beyond their day jobs.

Be sure to follow Cyber Culture® and visit  www.cyberculture.io to learn more about the work Oluwadamilola is doing!

Connect with The Cyber Boss®

• Connect with Dr. Ree on IG: @dr.jeree
• Follow ReeTheCyberBoss on IG and Threads: @reethecyberboss
• Follow The Cyber Boss Show™ on Spotify and Apple Podcasts
• Learn more about ReeTheCyberBoss® at www.reethecyberboss.com

Welcome to Season 3 of The Cyber Boss Show™! Dr. Ree is back behind the mic and catching you up on where she’s been, what’s changed, and what’s next for ReeTheCyberBoss®.

In this welcome back episode, she talks about becoming Dr. Ree, the evolution of RTCB® into Cyber and Everything In Between, and what you can expect from this new season from cybersecurity and cyberpsychology to digital safety, career belonging, creators, human behavior, and the way technology shows up in our everyday lives.

Plus, Season 3 is bringing something new: guests. 👀

New conversations. More perspectives. Same Cyber Boss.

The mic is back on and we have a LOT to talk about.

Connect with The Cyber Boss®

• Connect with Dr. Ree on IG: @dr.jeree
• Follow ReeTheCyberBoss on IG and Threads: @reethecyberboss
• Follow The Cyber Boss Show™ on Spotify and Apple Podcasts
• Learn more about ReeTheCyberBoss® at www.reethecyberboss.com

Seven years ago, ReeTheCyberBoss® began as an idea. Today, Dr. Ree reflects on the lessons, beliefs, and expectations she had to unlearn to become The Cyber Boss®. In this anniversary episode, she shares the truth about hustle culture, perfectionism, boundaries, success, confidence, and what it means to evolve.

If you have ever felt pressure to prove yourself, perform perfection, or keep shrinking to fit into spaces you’ve already earned, this episode is for you.

Connect with The Cyber Boss®

• Connect with Dr. Ree on IG: @dr.jeree

• Follow The Cyber Boss Show™ on IG: @thecyberbosspod

• Explore the ReeTheCyberBoss® Ecosystem: www.reethecyberboss.com

• Learn More about The Cyber Boss Show™ at www.thecyberbosspod.com

For mothers balancing careers, children, leadership, and the invisible weight of “doing it all,” this episode is for you.

In this episode, Dr. Ree gets honest about what motherhood really looks like when you’re navigating tech, cybersecurity, leadership, and high-demand careers. Through the lens of cyberpsychology and personal experience, she unpacks mom guilt, cognitive overload, digital burnout, and the pressure to keep performing even when you’re exhausted.

This isn’t a conversation about having it all together. It’s about giving yourself permission to redefine success, set boundaries, and stop pretending you’re fine when you’re running on empty.

If you’ve ever felt like motherhood changed you, your ambition, or the way you move through the world, you are not alone.

Connect with The Cyber Boss®

• Connect with Dr. Ree on IG: @dr.jeree
• Follow The Cyber Boss Show™ on IG: @thecyberbosspod
• Explore the ReeTheCyberBoss® Ecosystem: www.reethecyberboss.com
• Learn More about The Cyber Boss Show™ at www.thecyberbosspod.com

Networking isn’t about working the room, it’s about building the right ecosystem. In this episode of The Cyber Boss Show™,
Dr. Ree reframes networking as a strategic, psychological, and relational skill not a personality trait or popularity contest. Traditional networking advice often emphasizes visibility, proximity, and constant giving, but that approach doesn’t always lead to meaningful opportunities or sustainable success.

You’ll learn how to build relationships that actually create access, advocacy, and long-term influence without overextending yourself, oversharing, or chasing spaces that don’t align with your goals.

In this episode, you’ll learn:

• Why traditional networking advice often falls short

• How to build a relationship ecosystem instead of a contact lis

• The dangers of over-giving and over-sharing

• How to create alignment, advocacy, and opportunity

• Moving beyond proximity to power toward sustainable influence

If you’re ready to move from transactional connections to intentional relationship building, this episode will change how you think about networking forever.

Connect with The Cyber Boss®

• Connect with Dr. Ree on IG: @dr.jeree

• Follow The Cyber Boss Show™ on IG: @thecyberbosspod

• Explore the ReeTheCyberBoss® Ecosystem: www.reethecyberboss.com

• Learn More about The Cyber Boss Show™ at www.thecyberbosspod.com

Are you choosing a paycheck over your peace? To kick off Women’s History Month, Dr. Ree dives deep into why boundaries aren’t about being difficult and how they can become sustainable.

Black women are often pushed into over-functioning roles, carrying a heavy load of emotional labor both digitally and in person. Using the lens of cyberpsychology and lived experience, Dr. Ree breaks down how to protect your mental health and advance professionally without burning out.

In this episode, we discuss:

• Why boundaries are a power move, not a professional risk.

• The "Overfunctioning" trap and how it affects Black women in tech and corporate spaces.

• The Cyberpsychology of digital boundaries: How to log off without anxiety.

• How to set firm boundaries without fear, guilt, or over-explaining.

This is a masterclass in self-advocacy and power without apology. It’s time to secure your peace just as much as you secure your career.

Connect with The Cyber Boss®

• Connect with Dr. Ree on IG: @dr.jeree
• Follow The Cyber Boss Show™ on IG: @thecyberbosspod
• Explore the ReeTheCyberBoss® Ecosystem: www.reethecyberboss.com
• Learn More about The Cyber Boss Show™ at www.thecyberbosspod.com

Love shouldn’t cost you your peace or your passwords.

In this episode, Dr. Ree breaks down how relationships can become cybersecurity risks. From shared passwords to emotional pressure, this conversation explores digital boundaries, trust, and self-protection without fear or shame.

Connect with The Cyber Boss®

• Connect with Dr. Ree on IG: @dr.jeree
• Follow The Cyber Boss Show™ on IG: @thecyberbosspod
• Explore the ReeTheCyberBoss® Ecosystem: www.reethecyberboss.com
• Learn More about The Cyber Boss Show™ at www.thecyberbosspod.com

Dating apps don’t treat everyone the same and that matters. In honor of Black History Month, Dr. Ree explores how culture, algorithms, and cyberpsychology shape dating experiences for Black users. This episode connects emotional safety, digital wellness, and cybersecurity in a deeply human way.

Dr. Ree discusses the following:

• Bias in dating algorithms

• Visibility vs invisibility

• Emotional labor online

• Cultural awareness as protection

• Digital wellness as self-preservation

Connect with The Cyber Boss®

• Connect with Dr. Ree on IG: @dr.jeree

• Follow The Cyber Boss Show™ on IG: @thecyberbosspod

• Explore the ReeTheCyberBoss® Ecosystem: www.reethecyberboss.com

• Learn More about The Cyber Boss Show™ at www.thecyberbosspod.com

Your love language doesn’t disappear online. It shows up in your texts, DMs, and expectations. In this episode, Dr. Ree connects love languages, attachment styles, and cyberpsychology to explain how emotional needs shape online behavior and cybersecurity risk. From oversharing to boundary struggles, this conversation helps you understand why you show up the way you do online and how to protect yourself without shutting down connection.

Connect with The Cyber Boss®

• Connect with Dr. Ree on IG: @dr.jeree

• Follow The Cyber Boss Show™ on IG: @thecyberbosspod

• Explore the ReeTheCyberBoss® Ecosystem: www.reethecyberboss.com

• Learn More about The Cyber Boss Show™ at www.thecyberbosspod.com

Music Disclaimer:

ReeTheCyberBoss® or Dr. Ree do not own the rights to the music used in this video. The music clip is brief and used for illustrative and commentary purposes. All rights remain with the original copyright owners.

February is all about love but no one talks about how love can be engineered.

In this episode of The Cyber Boss Show™, Dr. Ree breaks down how social engineering shows up in dating, relationships, and digital intimacy. From love bombing and urgency to emotional manipulation and romance scams, this conversation blends cybersecurity, cyberpsychology, and real-life dating dynamics to help you protect your heart and your data.

This isn’t about fear or paranoia; it’s about awareness, boundaries, and digital self-respect.

Connect with The Cyber Boss®

• Connect with Dr. Ree on IG: @dr.jeree

• Follow The Cyber Boss Show™ on IG: @thecyberbosspod

• Explore the ReeTheCyberBoss® Ecosystem: www.reethecyberboss.com

• Learn More about The Cyber Boss Show™ at www.thecyberbosspod.com