Random but Memorable

Is shadow AI quietly creating risk inside your business? 🤖🔐 In this episode of Random but Memorable, you’ll learn what happens when employees adopt AI tools faster than teams can track them.

Amy Gebhardt, Senior Engineering Manager at 1Password, joins the show to unpack the security and visibility challenges behind shadow AI. The pair also discuss tokenmaxxing: a carefree approach to prompts, model calls, and AI agents that can lead to eyewatering bills. Learn why AI spend is so difficult to manage and how your team can spot waste without killing useful experimentation.

In Watchtower Weekly, we look at how AI agents are changing the speed of cyberattacks, and why visibility, access controls, and credential management matter more than ever. 

Finally, in #Ask1Password, we share our favorite underrated 1Password tips and features.

🏰  Watchtower Weekly

AI is changing the speed of cyberattacks

• An AI-Assisted Cyber Attack: Inside a Unit 42 Investigation
• AI agents carried out every step of this ransomware attack – then left the victim an 80-page security audit

🎙  Guest Interview – Amy Gebhardt

Amy Gebhardt, Senior Engineering Manager at 1Password, unpacks tokenmaxxing and the visibility challenges behind shadow AI.

• 👉 AI spend management with 1Password SaaS Manager
• 📄 1Password blog: The tokenmaxxing bill is due: Take control of AI spend
• 📲 Follow Amy Gebhardt on LinkedIn

🗣 #Ask1Password – Ask Us Anything! 

Please send us an email at: [email protected]

Ask us a question in the 1Password Community forum

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Editor's note: The views and opinions expressed by the interviewee don't represent the opinions of 1Password.

We all know AI models are getting better at finding software vulnerabilities. But can they fix them without creating new problems? In this episode, Wade sits down with Keith Hoodlet, 1Password’s Director of Security Research, to discuss new findings from Off-by-1 Labs.

Plus, how quickly does good cybersecurity start saving you money? 💸🔐 In Watchtower Weekly, we look at the rising cost of data breaches, and why investing in security might be far cheaper than dealing with the fallout. Using the latest numbers from IBM’s 2026 Cost of a Data Breach report, we explore how AI-enabled attacks are changing the economics of cybercrime. 📈

In #Ask1Password, we share our best tips for convincing your family to start using 1Password, especially if you’re already using it at work. 🧑‍🧑‍🧒‍🧒

🏰  Watchtower Weekly

Data breach costs climb as AI-powered attacks surge

🎙  Guest Interview – Keith Hoodlet

🗣 #Ask1Password – Ask Us Anything! 

Please send us an email at: [email protected]

Ask us a question in the 1Password Community forum

This week:

👉 Get a free 1Password Families membership when you use 1Password Business

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Editor's note: The views and opinions expressed by the interviewee don't represent the opinions of 1Password.

We’re back for a brand-new season! 🎉 And we're kicking things off with an evolving security risk in the AI space: prompt injection attacks..🤖⚠️

In Watchtower Weekly, we discuss how prompt injection has evolved from chatbot jailbreaks into a serious business risk. As AI tools start reading emails, documents, code, and other sensitive data, we go beyond the headlines to unpack the real-world impact of this attack vector. 

To dig deeper, Wade sits down with Johann Rehberger, independent AI security researcher and author of Embrace The Red. Johann explains how malicious instructions can hide inside the content AI tools process, and what organizations can do to reduce the blast radius.

Plus, in #Ask1Password, we explain the purpose of the Developer option in the 1Password desktop app, and how it helps protect SSH keys, environment secrets, and AI-powered development.

👉 Get started with 1Password developer tools

🏰  Watchtower Weekly

Prompt injection attacks pose growing risk to generative AI

🎙  Guest Interview – Johann Rehberger

🗣 #Ask1Password – Ask Us Anything! 

Please send us an email at: [email protected]

Ask us a question in the 1Password Community forum

This week:

👉 Get started with 1Password developer tools

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Editor's note: The views and opinions expressed by the interviewee don't represent the opinions of 1Password.

Always-on access might sound convenient, but it can quietly become a serious security risk. 🔐⚠️ In this bonus episode of Random but Memorable, we’re joined by Rom Carmel, VP of Product Management at 1Password, to introduce 1Password Privileged Access. 

Rom breaks down what privileged access management actually means, and why permanent permissions can leave companies exposed. He also explains how “just-in-time” and “just enough” access can protect teams and their most critical systems, without slowing everyone down. 

We also explore what happens when AI agents start needing access too, and why securing humans, machines, and agents is quickly becoming one of the biggest challenges for modern organizations. 👩‍💻

Learn more: Introducing 1Password Privileged Access

☑️ Listener Survey – Giveaway! 

WE NEED YOU! Our 2026 listener survey is now live, and we’d love to hear from you.

👉 TAKE THE SURVEY HERE

Have a favourite guest? Secretly skip a segment? Now’s your chance to let us know — honestly, we want to hear it all.

As a thank you, we’re giving three lucky listeners a free year of 1Password just for taking part. The survey takes less than five minutes and you can stay anonymous if you want to (but you’ll need to pop in your email address to enter the giveaway).  

📅 Giveaway ends: August 31, 2026

📜 Full Ts & Cs below.

🗣 #Ask1Password – Ask Us Anything! 

Please send us an email at: [email protected]

Ask us a question in the 1Password Community forum

📲  Follow Us…

❤️  Review Us...

If you're loving the show, please leave us a review on Apple Podcasts or wherever you listen to podcasts.

Giveaway Terms and conditions

NO PURCHASE NECESSARY. Open only to participants who are the age of majority where they reside. To enter, complete our 2026 listener survey and enter a valid email address. 3 winners will be selected at random to receive 1 free year of 1Password Families, valued at approximately $71.88 USD. The winners will be notified via direct message or email within 14 days after the giveaway ends and must respond within 30 days to claim the prize. 1Password reserves the right to modify or terminate the giveaway at any time. Personal information collected will only be used for giveaway administration. The giveaway runs from July 7, 2026 (09:00AM ET) - August 31, 2026. (12:00AM ET)

Fact or fiction? 🕵️‍♀️ In this bonus episode, Wade puts Sara and Jayden to the test with a series of cybersecurity myths, urban legends, and viral social media claims.

Can criminals steal your fingerprints from a selfie? Does Incognito Mode really hide everything you do? Is your phone secretly listening to serve you ads? And should you actually worry about public USB chargers or smart TVs? 🫆📲

Follow along and see if you can separate the facts from the fear mongering! By the end, you’ll know what’s worth worrying about and what’s not. 😅

☑️ Listener Survey – Giveaway! 

WE NEED YOU! Our 2026 listener survey is now live, and we’d love to hear from you.

👉 TAKE THE SURVEY HERE

Have a favourite guest? Secretly skip a segment? Now’s your chance to let us know — honestly, we want to hear it all.

As a thank you, we’re giving three lucky listeners a free year of 1Password just for taking part. The survey takes less than five minutes and you can stay anonymous if you want to (but you’ll need to pop in your email address to enter the giveaway).  

📅 Giveaway ends: August 31, 2026

📜 Full Ts & Cs below.

🗣 #Ask1Password – Ask Us Anything! 

Please send us an email at: [email protected]

Ask us a question in the 1Password Community forum

📲  Follow Us…

❤️  Review Us...

If you're loving the show, please leave us a review on Apple Podcasts or wherever you listen to podcasts.

Giveaway Terms and conditions

NO PURCHASE NECESSARY. Open only to participants who are the age of majority where they reside. To enter, complete our 2026 listener survey and enter a valid email address. 3 winners will be selected at random to receive 1 free year of 1Password Families, valued at approximately $71.88 USD. The winners will be notified via direct message or email within 14 days after the giveaway ends and must respond within 30 days to claim the prize. 1Password reserves the right to modify or terminate the giveaway at any time. Personal information collected will only be used for giveaway administration. The giveaway runs from July 7, 2026 (09:00AM ET) - August 31, 2026. (12:00AM ET)

You asked, we answered! 🎙️🔐 In this bonus episode of Random but Memorable, we’re tackling listener questions from Reddit and the 1Password Community.

We cover everything from why some people are still skeptical of passkeys, to the role 1Password will play in a future where AI agents sign in and complete tasks on our behalf. Plus, we dig into 1Password Environments and how it helps developers securely manage secrets.

Allie, Matt, and Wade also reveal the cybersecurity misconceptions they’d love to retire for good.

Short, practical, and packed with listener questions — keep them coming at [email protected]

🗣 #Ask1Password – Ask Us Anything! 

Please send us an email at: [email protected]

Ask us a question in the 1Password Community forum

📲  Follow Us…

❤️  Review Us...

If you're loving the show, please leave us a review on Apple Podcasts or wherever you listen to podcasts.

Anyone can build software with AI now, and millions of people are giving it a try. But when AI can spin up an app in minutes, are security risks slipping through the cracks? 👀💻 In our season finale of Random but Memorable, we dive into the promise and pitfalls of building software with AI.

First, in Crash Course, Roo breaks down what vibe coding actually means, why it’s suddenly taken off, and how people are using AI tools to build apps, websites, games, and workflows. Then, in Watchtower Weekly, we look at the security risks, including exposed data and leaked API keys, and why AI-built apps still need real software guardrails.📲

Later, Wade sits down with Jeff Malnick, 1Password’s VP of Engineering for Developer & AI, to discuss how to start vibe coding without creating a cybersecurity risk. From code review and developer best practices to the future of AI-assisted software development, this conversation is packed with practical advice for anyone experimenting with AI and code.🤖👨‍💻

🏰  Watchtower Weekly

Thousands of Vibe-Coded Apps Expose Corporate and Personal Data

👨‍🏫  Crash Course

Vibe coding 👨‍💻

🎙  Guest Interview – Jeff Malnick

🗣 #Ask1Password – Ask Us Anything! 

Please send us an email at: [email protected]

Ask us a question in the 1Password Community forum

📲  Follow Us…

❤️  Review Us...

If you're loving the show, please leave us a review on Apple Podcasts or wherever you listen to podcasts.

Editor's note: The views and opinions expressed by the interviewee don't represent the opinions of 1Password.

Traveling soon? ✈️🔐 This week’s episode is your cybersecurity guide for life on the move. Learn how to keep your personal and professional data secure while navigating  airports,  public Wi-Fi, and local pickpockets. 

In Crash Course, we break down 1Password Travel Mode: what it is, how it works, and how it can help protect your most sensitive information when traveling.

Wade then sits down with Gerald Auger from Simply Cyber for a practical conversation about travel security. The pair cover vacation risks, business trips, free Wi-Fi, lost devices, and the simple habits that make traveling a whole lot safer. 🛜🏨

Plus, we reveal the winners of our 1Password giveaway!

🏰  Watchtower Weekly

Why Hackers Are Targeting the Education Sector

👨‍🏫  Crash Course

1Password's Travel Mode ✈️

🎙  Guest Interview – Gerald Auger

🗣 #Ask1Password – Ask Us Anything! 

Please send us an email at: [email protected]

Ask us a question in the 1Password Community forum

📲  Follow Us…

❤️  Review Us...

If you're loving the show, please leave us a review on Apple Podcasts or wherever you listen to podcasts.

Editor's note: The views and opinions expressed by the interviewee don't represent the opinions of 1Password.

Giveaway Terms and conditions

NO PURCHASE NECESSARY. Open only to participants who are the age of majority where they reside. To enter, subscribe to the Random but Memorable YouTube channel and comment on our World Password Day Special with your favorite Random but Memorable tip or trick. 3 winners will be selected to receive 1 free year of 1Password Families, valued at approximately $71.88 USD. The winners will be notified via direct message or email within 14 days after the giveaway ends and must respond within 30 days to claim the prize. 1Password reserves the right to modify or terminate the giveaway at any time. By accepting the prize, the winner agrees to allow 1Password to use their name and comment for promotional purposes. Personal information collected will only be used for giveaway administration. The giveaway runs from May 12th, 2026 (09:00AM ET) - May 20th, 2025. (12:00AM ET)

In our World Password Day Special, we’re digging into credentials, identity, and authentication  — and where security is  heading next. 🔐✨

In Watchtower Weekly, we reveal how people are using AI to generate passwords… and why that might not be a great idea. Then, in Crash Course, you’ll learn about entropy — what it actually means, and what makes a password truly strong. 🔤

1Password CISO Jacob DePriest joins the show later on to talk about identity security and the future of authentication. We cover password hygiene in 2026, passkeys, “passwordless,” and the rise of AI agents needing access to our accounts.

Plus: we’re celebrating World Password Day with a giveaway — your chance to win a free year of 1Password. 🎉

🎁 World Password Day – Giveaway!

In celebration of World Password Day we’re running a giveaway! 🎉

👉 To enter, subscribe to Random but Memorable on YouTube and comment on this episode with your favorite 1Password tip or trick.

We’ll share 3 of our favorites on the next episode and they’ll each win 1 free year of 1Password! 

This giveaway is now open and closes at midnight on May 20th. Terms and conditions below.

🏰  Watchtower Weekly

AI Passwords Look Smart—But They're Full of Patterns

👨‍🏫  Crash Course

Entropy

🎙  Guest Interview – Jacob DePriest

🗣 #Ask1Password – Ask Us Anything! 

Please send us an email at: [email protected]

Ask us a question in the 1Password Community forum

📲  Follow Us…

❤️  Review Us...

If you're loving the show, please leave us a review on Apple Podcasts or wherever you listen to podcasts.

Editor's note: The views and opinions expressed by the interviewee don't represent the opinions of 1Password.

Giveaway Terms and conditions

NO PURCHASE NECESSARY. Open only to participants who are the age of majority where they reside. To enter, subscribe to the Random but Memorable YouTube channel and comment on our World Password Day Special with your favorite Random but Memorable tip or trick. 3 winners will be selected to receive 1 free year of 1Password Families, valued at approximately $71.88 USD. The winners will be notified via direct message or email within 14 days after the giveaway ends and must respond within 30 days to claim the prize. 1Password reserves the right to modify or terminate the giveaway at any time. By accepting the prize, the winner agrees to allow 1Password to use their name and comment for promotional purposes. Personal information collected will only be used for giveaway administration. The giveaway runs from May 12th, 2026 (09:00AM ET) - May 20th, 2025. (12:00AM ET)

So you’ve been hacked… Now what?! 😬🔐 We all think it won’t happen to us — until it does. In this episode, we take a break from prevention and focus on the important steps to follow if the worst actually happens.

Glenn Wilkinson, cybersecurity expert and co-founder of Agger Labs, explains what to do if you, someone you love, or your organization gets hacked. From compromised email accounts to ransomware and the high-stakes decisions that follow, Glenn shares clear advice on how to respond, recover, and stay calm under pressure. 😌📲

Plus, in Watchtower Weekly, we discuss Anthropic’s Project Glasswing and what it could mean for the future of AI and software vulnerabilities. Then, in Crash Course, we break down open-source security — the community-driven model that helps protect huge parts of the internet.

And in #Ask1Password, we share tips for helping your team actually adopt 1Password after a rollout.

🏰  Watchtower Weekly

The newest AI models: Claude Mythos and GPT-5.4-Cyber

👨‍🏫  Crash Course

Open Source Security

🎙  Guest Interview – Glenn Wilkinson

🗣 #Ask1Password – Ask Us Anything! 

Please send us an email at: [email protected]

Ask us a question in the 1Password Community forum

📲  Follow Us…

❤️  Review Us...

If you're loving the show, please leave us a review on Apple Podcasts or wherever you listen to podcasts.

Editor's note: The views and opinions expressed by the interviewee don't represent the opinions of 1Password.