Coffee Meets Cloud

This week, we’re joined by Sheridan Guest for a conversation that starts with an unexpected career pivot from pre-med to tech sales, and quickly expands into something much bigger: how we communicate, adapt, parent, and stay human in a world increasingly shaped by AI.
Sheridan shares what cold calling Canada and Boston taught her about reading the room, why becoming a mother changed the way she approaches people at work, and how emotional intelligence can be just as important as technical skill.
Then we dig into the harder questions around AI. What happens when kids begin turning to AI for connection and advice? Are productivity tools actually giving us more time—or just creating more space for another form of digital distraction? And how do we use AI to remove the administrative noise from our lives without outsourcing the thinking, relationships, and experiences that actually matter?
Along the way, we talk ChatGPT, Claude, Copilot, Slackbot, the Voynich manuscript, AI guardrails, parenting in the digital age, and why the goal shouldn’t be to automate everything.
Because maybe the most important question isn’t “What can AI do for us?”
It’s “What are we going to do with the time it gives us back?”

This week on Coffee Meets Cloud, we’re covering the full spectrum of modern survival: overpriced energy drinks, a Jonas Brothers wardrobe malfunction, high school prank wars that have gone way too far, Southern hurricane prep, college football superstitions, and why everything suddenly costs a small fortune.
We also get into one very real AI win—when ChatGPT managed to navigate an Atlanta parking nightmare that Apple Maps couldn’t—and talk about why tools like AI are becoming surprisingly useful in everyday life.
Plus: Waffle House lore, questionable hurricane food choices, Jesus candles, Nick Saban’s redemption arc, and the sacred rituals of college football Saturdays.
It’s chaotic, practical, nostalgic, and exactly the kind of conversation you’d expect over coffee.

This week, we’re fully embracing false fall—and everything that comes with it. We’re talking Atlanta traffic and suburban sprawl, DIY projects that take three times longer than YouTube promised, college football, Joro spider chaos, neighborhood Halloween contests, and why the internet seems determined to turn everything into outrage.
Then we get nostalgic. From Cool Whip containers and mason jars to homemade Christmas decorations and screen-free family traditions, we’re asking what we’re really chasing when we say we want the holidays to feel like they did in the ’90s—and why, as parents, we might just be the keepers of the magic now.
Plus: TV recommendations, plant struggles, fire safety lessons learned the hard way, and the usual Coffee Meets Cloud detours.

This week, we’re unpacking some of the biggest conversations coming out of Dreamforce—from responsible AI and protecting human creativity to the growing reality of surveillance pricing and just how much of our data retailers can use against us. Plus, we kick things off with flight anxiety, questionable airplane etiquette, and the eternal debate: drive or fly?

What happens when the career goal you’ve been chasing turns out not to be the one you actually want?
This week on Coffee Meets Cloud, Caramie, Cassandra, and Rachel talk career pivots, personal development, and why great leaders should help people grow, even when that growth eventually takes them somewhere else. From protecting time to learn to shadowing other roles and refusing to accept “stay in your lane” leadership, we’re talking about what it really takes to figure out where you want your career to go.
Then things get a little more existential.
AI is moving fast. Like... uncomfortably fast. We dig into the growing conversation around AI risk, whether regulation can possibly keep pace, why so many people still aren’t paying attention, and why none of those concerns are stopping us from using AI every day.
Plus, Dreamforce 2026 is almost here, Usher is playing Dreamfest, hotel prices are offensive, asking for help might actually be a superpower, football is officially back, and the SEC has some explaining to do.
Your career doesn’t have to follow the plan you made five years ago, and changing direction doesn’t mean you failed. Sometimes figuring out what you don’t want is exactly how you get closer to what you do.
Grab your coffee and join us.

For this throwback episode, we’re revisiting one of our early favorites featuring Betsy Robinson, Founder & CEO of Tier 4 Group and Board President of Women in Tech Atlanta, and a conversation that challenged one of the most persistent ideas about career growth: that success means continuously climbing upward.
Betsy introduces the idea of a career lattice, where lateral moves, pivots, new experiences, and sometimes even stepping sideways can create far more valuable opportunities than chasing the next title.
We talk about what it looks like to build a career around your goals and values instead of someone else’s definition of advancement, why unconventional career moves can become some of the most important ones, and how to recognize when the traditional ladder simply isn’t taking you where you actually want to go.
And because this is Coffee Meets Cloud, career strategy isn’t the only thing on the agenda. We also attempt to keep up with the latest slang from the younger generation.
Whether you heard this episode the first time around or you’re discovering it for the first time, it’s worth a listen.

What do household budgets, Dreamforce FOMO, latchkey kids, difficult conversations, and teaching a nine year old to own his mistakes have in common? More than you might think.
This week, Caramie, Cassandra, and Rachel talk about the ways context shapes how we experience everything from money and parenting to work and relationships. Caramie shares how she is using AI as a “Household CFO” to tackle consumer debt and reduce financial stress, which turns into a conversation about ChatGPT, Claude, Rocket Money, spreadsheets, and why the best tool is often the one that works the way your brain works.
The conversation then shifts to a viral discussion about leaving kids home alone, how socioeconomic circumstances influence our definitions of safety, and why there is rarely one universal answer to parenting decisions.
From there, the hosts dig into something that affects nearly every relationship: the words we choose. They explore the difference between intent and impact, why absolutes like “always” and “never” can derail a conversation, and how learning to respond instead of react can completely change an interaction.
Finally, a parenting challenge becomes a lesson that applies just as much to adults in the workplace: accountability has to be communicated. Owning a mistake does not mean shrinking yourself. Sometimes it means doing exactly the opposite.
As Cassandra puts it: Take up the space you own.

This week, we're asking the important questions: Why did adulthood look so much easier when our parents were doing it? How did we survive childhood with no location tracking, questionable car safety, and instructions to just come home when the streetlights came on? And which things from our childhood actually deserve a comeback?
We're talking about the surprisingly hard parts of being a grown-up, the parenting choices that would send today's internet into a spiral, and the things we desperately want to bring back. Some things were absolutely better left in the past. Others? We may have overcorrected.
Plus, we debate the ultimate question: would we actually want to live in a world without smartphones again?

This week, we’re questioning the things we’ve accepted as fact simply because someone told us they were true. From swallowed gum and tongue maps to the infamous five-monkeys experiment and the workplace classic, “we’ve always done it this way,” we’re talking about why bad information—and bad habits—stick around.
Plus, the usual side quests: duvet cover rage, dangerous kitchen tools, parenting trial and error, the art of negotiation, and a surprisingly passionate amount of pickle talk.
Sometimes the smartest thing you can do is ask: Wait… is that actually true?

This week, we’re talking about the increasingly blurry line between using AI and letting AI do everything for you—from earning Trailhead badges to writing painfully obvious workplace messages and helping candidates fake their way through interviews.
We also get into dual enrollment, why high school from home is absolutely not entering our WFH households, the importance of knowing when a hire just isn’t working out, and why sometimes everyone needs to close the laptop and touch grass.
Plus: recurring school nightmares and the debate that really matters—which OG boy band was actually the best?