Off the VPN

Off the VPN

Download on the App Store

Off the VPN episodes

  • Her majesty, the principal engineer

    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


    41 min
  • If you want to escalate, we can escalate

    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

    29 min
  • 10x engineer or 10x scammer?

    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


    36 min
  • The feature that ruined my life

    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


    32 min
  • The dev who saved Christmas

    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

    32 min
  • We need to talk about 2024

    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

    43 min
  • You’re not doing networking wrong

    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

    43 min
  • Some teams can't be saved

    Ever feel like you’re the only one actually working? Or that your “team-building” aren’t exactly inspiring team spirit? On this episode of Off the VPN, Allison and Jasmine run through the good, the bad, and ugly of building  tech team “synergy”.

    From the nightmare of being left on read by your whole team to the perils of “mandatory” trust falls, our hosts spill the tea on what makes ( and breaks) a solid team. Hang out for some laughs, a few rants, and maybe even a little actionable insight into what will help you survive team drama!

    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 Mystery of Team Silence: Allison and Jasmine unpack a wild tale of a tech team leaving one unlucky member completely on read. 
    • Toxic vs. Tight-Knit Teams: From the icy, every-person-for-themselves teams to overzealous bonding teams obsessed with trust falls how do you actually build a better team? 
    • Surviving Unnecessary Team-Building Exercises: Jasmine’s got some unorthodox ideas on turning team bonding into something less…cringeworthy. How can we set healthy boundaries in the workspace without mandatory team events?

    Jump into the conversation:

    (00:00) Today’s topic: team drama and tech tea

    (01:15) Left on read by the whole team – what’s the deal?

    (05:32) Toxic teams vs trust falls – handling extreme dynamics

    (10:44) Boundaries in bonding and the cringe of forced fun

    (15:08) Surviving “mandatory” team-building – pro tips from the hosts

    (20:25) When management steps in…or doesn’t

     

    37 min
  • GenAI Ghost Stories

    There’s something spooky on the horizon, and we’re not talking about ghosts and goblins. AI is changing the future of software development. And while change is scary, AI could be more about treats than tricks. So says Julia Neagu, CEO and Co-founder of Quotient AI. In this episode of Off the VPN, Julia sheds a little light on an AI-assisted future and reigns in some of our scariest AI expectations. Can AI control the weather? No. Should AI-assisted engineers get paid less? Also no. 


    For a full discussion on how AI is changing the developer role and why it won’t be taking over for software engineers anytime soon, be sure to give this episode a listen. And stick around for some seasonally appropriate terror tales from the darkest recesses of the tech industry—if you dare.


    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:

    • Developers vs. AI: Julia shares her take on how AI is transforming the developer role, debunking the myth that AI tools like ChatGPT will replace engineers. Instead, she emphasizes the evolving nature of engineering, where AI assists rather than replaces human creativity.
    • The Developer Pay Cut Debate: The hosts break down a shocking Reddit post where a manager slashed developer pay by 20%, believing AI could replace them. Jasmine, Allison, and Julia dive into the ethics and misconceptions surrounding AI in the workplace.
    • The Future of Engineering: Julia explores how AI will reshape the future of junior developer roles, highlighting the need for education to adapt to new tools and technologies while ensuring developers still build solid foundations in core engineering skills.

    Jump into the conversation:
    (00:00) Introducing Quotient AI’s Julia Neagu
    (02:35) AI transforms how developers work
    (08:20) Trick or Tech? Weird AI claims
    (13:47) Manager cuts developer pay due to AI
    (19:15) The future of junior devs in an AI world
    (23:58) Collaboration between developers and non-tech teams
    (30:10) AI's impact on engineering and future education

    36 min
  • Stand ups and other useless meetings

    Are we the only ones sitting in way too many meetings or what? How’s any work supposed to be done if we’re chit-chatting away on daily stand-ups? In this episode of Off the VPN, Allison and Jasmine talk about the overload of unnecessary meetings in the tech world — sharing listener stories and exploring the countless red flags of inefficient workplace practices. Tune in for laughs, advice, and some much-needed reality checks on how we handle our time in the tech world. Spoilers: It could have been an email.


    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:

    • Three Stand-Ups in a Day: Can you imagine giving the same status update three times in a single day? Jasmine and Allison break down the absurdity of excessive meetings and discuss how to streamline communication for better productivity.
    • Video On Debate: Should cameras be on or off during virtual meetings? A listener’s hot take sparks a conversation about remote work culture.
    • Micromanagement Overload: Feeling micromanaged by endless check-ins? Jasmine and Allison share a story about a team lead who insists on multiple daily meetings and offers strategies to push back on inefficient management.


    Jump into the conversation:
    (00:00) Back from vacation!
    (02:24) Today’s topic: Meetings – Why do we have so many?
    (04:00) How to decide if a meeting is necessary
    (08:33) “No customer will ever buy this feature!”
    (10:05) Questioning product development decisions in meetings
    (12:49) Being realistic with delivery dates
    (14:24) Managing time conflicts in project work
    (16:09)  Should cameras be on in meetings?
    (21:00) The story of too many stand-up meetings
    (25:01) How to handle meeting overload and find balance
    (29:59) Evaluating the ROI of long meetings
    (31:08) Being conscious of time spent in meetings

    38 min

About Off the VPN

From the publisher's feed

Is bringing up your software engineering salary a dating red flag? How do you strike a balance between career ambition and incendiary burnout? Is it ever okay to hold your code hostage in escrow? Navigating a career in tech raises a lot of tricky questions that aren’t exactly appropriate for the daily stand-up. So let’s take this off the VPN.