Sometimes getting random DMs in your online community doesn’t always work out like you want it to.  

Picture this, you're Aubrey, a cybersecurity pro thriving in a fast-paced tech scene. Everything’s going smoothly until you try to do a nice thing - offering some extra tickets to a local disco costume party. Sounds harmless, right…right!? 

Enter Ted: a seemingly well-meaning but totally clueless guy who doesn’t quite get the boundaries. What starts as a small gesture develops into a series of awkward DMs, boundary-pushing, and what we’d call very awkward exchanges, oof!

Got a tech tale of your own or some workplace drama? Hit us up at jellyfish.co/offthevpn. And don’t worry—we’ll keep it Off the VPN.

Highlights:

• Ted Doesn’t Get the Memo: You gotta read the room yo! 
• Aubrey Goes CSI: It all starts with the phone number
• Community Vigilance: Moderators, we love you, thanks for keeping communities safe!

Jump into the conversation:
(00:00) Intro
(03:47) Aubrey’s generous ticket giveaway
(07:02) Ted’s unsolicited messages start flooding in
(09:10) Boundaries set, but Ted doesn’t get the hint
(12:55) Crossing over the cybersecurity line
(17:02) When online turns real
(20:52) Aubrey plays CSI on Ted
(25:40) Community moderators step in
(28:09) The moral of the story: Privacy, people

Imagine you’re our good friend Logan (aka the Wolverine) and work is steady – yay!  When all of a sudden a “low priority” side project made it to the CEO’s radar…bummer. 

Chaos begins, stress rises, deadlines shift, and communication has flown out the window. What was once a simple task is now a ticking time bomb. With a small team and virtually no additional resources, Logan’s feeling the summer heat early. As icing on the cake, throw in an MIA manager while the CEO presses for a demo that isn’t even ready.

Want to ask us something or share your own work drama? Hit us up at jellyfish.co/offthevpn. And don’t worry—we’ll keep it Off the VPN.

Highlights:

• Low prio is High Prio: When “no rush” actually  means “drop everything now”
• Communication Void: Weekly updates on Slack with nothing but a thumbs up
• CEO Curveballs: The art of war in urgent demands from the Big Boss 

Jump into the conversation:
(00:00) Intro

(01:47) A nightmare on techstreet

(03:33) Logan: solo support and side quests

(05:16) The “side project” that’s not side

(10:12) Priorities lost in translation

(13:49) Professor X wants the integration

(15:40) CEO’s surprise: where’s the demo button?

(18:58) New deadline, instant chaos, Logan’s dread

(21:12) Panic mode: calling all hands

Lily’s onboarding plan? Hit the ground running. Bart’s plan? Monitor her calendar like it’s a live-action thriller. From week one, it’s all tension, mixed signals, and a staff engineer just trying to do her job.

This episode follows the slow-motion implosion of a tech team where one EM’s insecurities create a ripple effect of firings, confusion, and eventually, some pretty unconventional tactics from leadership. There’s a spy, some corporate melodrama, and a reminder that being good at your job can really tick off the wrong people.

Got a question you’d like answered on the show? Drop us a line at jellyfish.co/offthevpn. And don’t worry! We promise to keep it Off the VPN.

Highlights:

• Spy Games: When leadership plants someone on your team just to confirm your EM is the problem
• Calendar Chaos: Lily tries to onboard, Bart tries to control every meeting she has
• Skip-Level SOS: Why going around your manager might’ve saved this entire mess earlier

Jump into the conversation:
(00:00) Intro
(00:13) Bruises, burnout, and beach dreams
(01:46) Lil Instinct lands the job, kinda
(03:11) Bart shows up weird from day one
(04:53) Trusting your gut when it’s sus
(07:11) New gig, same mess, calendar police
(09:30) Bart micromanages like it’s his hobby
(13:52) Being helpful somehow makes it worse
(18:52) Should’ve gone skip-level yesterday
(26:36) Surprise! The new guy was a spy
(29:45) Bart’s gone and finally, peace returns
(34:38) Tech trauma is real, but so is recovery

While Jasmine is enjoying her office sauna, our friend, “Hank” is ready to burn bridges. So the heat is high across the board, but while one situation has vacation vibes, the other is centered around an overqualified engineer.
 
This week, we’re getting into the chaos of tech teams, where legacy systems, ego battles, and one very opinionated senior dev threaten to tear it all down. From the drama of refactoring a hot mess of code to meetings derailed by a team member who just can’t help but feel strongly opinionated, the struggle is real.

Want to ask us something or share your own work drama? Hit us up at jellyfish.co/offthevpn. And don’t worry—we’ll keep it Off the VPN.

Highlights:

• Egos on Fire: When one dev’s talent causes a maelstrom of team-wide burnout.
• Spaghetti Code & Sabotaged Meetings: How a single codebase becomes the stuff of nightmares.
• The Price of Talent: What happens when you let one person dominate the team’s rhythm?

Jump into the conversation:

(00:00) Intro

(03:52) The Tale of Maria

(05:54) Legacy systems built by one person

(06:30) No documentation or code reviews

(09:01) Refactoring an old convoluted system

(11:20) Balancing tech debt and new features

(17:36) Maria managing more than just Hank’s KPIs

(21:36) Psychological safety with Hank

(24:47) Hank’s behavior impacts team morale

(28:54) Leadership challenges for Maria

(32:22) Emotional toll of managing Han

Jasmine bought a sauna and “Deb” lost her job. One of those stories is relaxing—the other, not so much. This week, Allison brings a tale straight from the tech trenches: a PM asks for a little backup on a big customer call, and somehow ends up ousted from the team. From calendar drama to missed deadlines and a total breakdown in trust, this one’s got everything except a single honest conversation.

Got a question you’d like answered on the show? Drop us a line at jellyfish.co/offthevpn. And don’t worry! We promise to keep it Off the VPN. 

Highlights:

• The Vibes Are Immaculate… Until They’re Not: When leadership excitement turns into a pressure cooker.
• Fake Demos & Fast Deadlines: How a half-baked prototype turns into an urgent, must-ship-now nightmare.
• Burnout & Moving On: What happens when work keeps piling up and the recognition is absent?

Jump into the conversation:
(00:00) Intro
(03:08) A classic PM vs EM power struggle
(04:26) Deb asks for help on a customer call
(07:24) Missed deadlines and broken expectations
(10:56) Performance issues derail the launch
(12:29) EM questions Deb’s 1:1s with data
(14:49) Control, ego, and influence at play
(18:02) Deb gets cut out without warning
(22:59) Bad PM-EM dynamics hurt everyone
(25:28) Crashing out together, one story point at a time

Escalations, stress, and a side of existential crisis—just another day in tech. 

Ever wondered how to handle high-stakes incidents, and then realized just how much of IT work can be automated? This episode jumps into the weird world of tech jobs that shouldn’t be full-time but somehow are. Is it a win-win, or just corporate oblivion at its finest? And what happens when you’re so good at your job that you automate your way out of it? Let’s find out.

Got a question you’d like answered on the show? Drop us a line at jellyfish.co/offthevpn. And don’t worry! We promise to keep it Off the VPN.

Highlights:

• The Hive Mind Effect: How working through chaos turns coworkers into an eerily synchronized unit.
• The Growing Tech Knowledge Gap: When outdated systems and hiring missteps lead to jobs that shouldn’t exist.
• AI, Automation, and Ethics: The fine line between streamlining workflows and making yourself obsolete.

Jump into the conversation:
(00:00) Intro

(01:30) The hive mind effect at work

(04:23) Automating yourself out of a job

(06:50) Digital evidence and IT headaches

(10:10) Cloud security and legal risks

(14:18) AI, automation, and job fears

(17:03) The ethics of doing less work

(20:27) Why tech hiring goes wrong

(22:15) The growing tech knowledge gap

(24:41) Generative AI and fear-driven choices

New year, same chaos. Allison and Jasmine are back with a tech industry tale that has it all:  job-hopping, fake demos, impossible deadlines, and promotions sliding into the void. From conference standing ovations to the reality of shipping a mediocre product, we’re recounting a story about what happens when expectations don’t match the execution. Can a tooltip ruin your life? Let’s find out!  

Got a question you’d like answered on the show? Drop us a line at jellyfish.co/offthevpn. And don’t worry! We promise to keep it Off the VPN.

Highlights:

• Vibes Are Immaculate… Until They’re Not: When leadership excitement turns into a pressure cooker.
• Fake Demos & Fast Deadlines: How a half-baked prototype turns into an urgent, must-ship-now nightmare.
• Burnout & Moving On: What happens when work keeps piling up and the recognition is absent? 

Jump into the conversation:
(00:00) Getting back into the swing of things

(01:19) Aaron’s story of tech highs and lows
(03:03) Dream jobs and the engineering rollercoaster

(04:47) Conference demos: Big wins, big risks

(08:19) Leadership shifts, reorgs, and trouble ahead

(10:48) The White Whale of “Vizzy”

(14:03) Fake demos, big promises, execs want it now

(17:31) Product managers and realistic deadlines

(24:16) Chasing a promotion that never comes

(28:43) Silent rejection, a final push, and an empty win

(32:57) Burnout hits: Knowing when it’s time to go

Is it really the Holiday Season in Tech without some year-end chaos? In this episode of Off the VPN, we get into a caroling mood and talk about the festive quirks of the Tech industry while we Make the Yuletide gay. From hypothetical code freeze nightmares to awkward holiday Zoom parties, it’s all about navigating the end-of-year madness. Put your stockings up above the fireplace, and tune in for some “juicy” holiday cheer (or coal).

Got a question you’d like answered on the show? Drop us a line at jellyfish.co/offthevpn. And don’t worry! We promise to keep it Off the VPN. 

Highlights:

• Tech & Festivities: Allison and Jasmine unpack the unique energy of the season in tech—deploy freezes, year-end wrap-ups, and on-call rotation woes.
• Cheers or Coal: A holiday-themed “would you rather” game puts the duo to the test with scenarios like Zoom caroling and CEO TikTok dances.
• Holiday Hilarity: Feeling micromanaged by endless check-ins? Jasmine and Allison share a story about a team lead who insists on multiple daily meetings and offer strategies to push back on inefficient management.

Jump into the conversation:
(00:00) Kicking off with holiday vibes and tech quirks

(03:12) Snow days, ski masks, and heated blanket dreams

(06:25) The chaos of year-end product deployment 

(09:38) Choose your coal: Holiday bugs or January incidents?

(12:51) Zoom caroling vs. company hoodies: The ultimate debate

(15:42) Year-end reviews: Feedback nightmares or holiday cheer?

(18:49) CEO TikTok trends: Cringe-worthy or genius?

(22:15) Surviving holiday mishaps in the tech world

(27:01) Wrapping up with holiday fails and festive laughs

The year in tech, decoded and all wrapped up! Today’s episode looks back and closes the book on 2024 with special guest Patrick Austin, Founding Editor at IT Brew. From the disruption of Artificial Intelligence to news headlines that shook the balance of the industry, Patrick, Jasmine, and Allison break down the great, the terrible, and the absolutely bizarre tech moments that defined 2024.

Whether you’re curious about tech’s biggest wins and mishaps, the “weirdo” tech innovations, or how to keep track of the buzzing news line, this episode’s for you! 

Got a question you’d like answered on the show? Slide into our DMs at jellyfish.co/offthevpn. And don’t worry! We promise to keep it Off The VPN.

Highlights:

• Weirdest Tech Headlines of The Year: From breakup-text summarizers to hologram brides, we bring you the year’s most jaw-dropping tech headlines.
• Tech News Overload: Patrick shares his go-to strategies for staying informed without burning out and panicking.
• Manifesting For a Smarter Tech Future Today: We’re all in this together, and hope to see that manifest in 2025. We’re looking forward to more ethical developments to AI, new technologies, and apartment-friendly saunas (yes, really). 

Jump into the conversation:

(00:00) Wrapping up 2024 in tech with Patrick Austin

(03:56) Patrick’s path from IT to tech journalism

(06:01) Two headlines and a lie: the AI edition

(16:03) The smart spoon debate: tech innovation or just plain weird?

(21:14) Keeping up with tech news: tips for avoiding overload

(27:42) AI controversies: from helpful tools to ethical dilemmas

(33:15) Manifestations for 2025: ethical AI and informed leaders

(38:37) Apartment-friendly saunas and other fun predictions

There’s a new era of networking in tech, and it’s not all polished LinkedIn posts, Zoom mixers, or networking events. Today’s episode of Off The VPN discusses the modern rules of tech networking with special guest Meghan Halton, Senior Engineering Manager at Kibeam Learning. From the awkward icebreakers to the pressure of LinkedIn profile management,  Meghan, Jasmine, and Allison break down what’s really worth the hype—and what’s not worth the time.

Whether you’re figuring out how to maximize online and offline events, building genuine connections, or debating what to share on LinkedIn, today’s episode gives us a fresh perspective. So, if you’re wondering what the absolute essentials are, this one’s for you!

Got a question you’d like answered on the show? Slide into our DMs at jellyfish.co/offthevpn. And don’t worry! We promise to keep it Off The VPN. 

Highlights:

• LinkedIn: Essential Tool or Necessary Evil? Meghan and the hosts share their love-hate relationship with LinkedIn, from the professional wins to the social media burnout.
• Virtual Networking: Connection or Just Convenience? The pros and cons of remote-only networking events, plus tips on creating real connections online.
• Mastering the Art of Conference Mingling: Whether it’s a happy hour or a speed networking game, Jasmine, Allison, and Meghan discuss the secrets to turning conference mixers into genuine networking wins.

Jump into the conversation:
(00:00) Today’s topic: navigating tech networking with Meghan
(03:12) The LinkedIn debate: love it or leave it?
(09:24) Virtual networking events: connection vs. convenience
(15:46) In-person conferences: making real connections in tech
(21:13) Mixer moments: how to handle conference happy hours
(27:48) Imposter syndrome at conferences: advice for newcomers
(32:22) Networking games: icebreakers or cringe-worthy activities?
(37:09) Maintaining professional connections: pro-tips from Meghan