Podcast Episode 22

Episode 022 35 min

Michael Crandell, CEO at Bitwarden Inc., on Open Source Security

with Michael Crandell · Bitwarden Inc.

0:00 / 35:00

Also on Spotify, Apple Podcasts, YouTube, Podbean, Player FM

Episode 22 of The Security Podcast of Silicon Valley, published October 1, 2022. Host Jon McLachlan talks with Michael Crandell, then CEO of Bitwarden, the open source password manager. The conversation covers why a secure password must be unique and complex, a sweet spot of about 14 characters, the knob between security and ease of use, a company built by one founder, Kyle Spearrin, a new CEO's mantra not to break what works, the best day in customer support, a free version that's free forever with no tracking, how free users bring Bitwarden to work, the trust playbook for selling to enterprises from SOC 2 and SOC 3 to an SLA, leaning in with a buyer's security team, a worst day that repeats, what sets Bitwarden apart, why almost nobody rebuilds an open source app with eight or 10 clients, end-to-end encryption next to self-hosting and data residency, a fully remote company whose four values spell GRIT, an interview question about age 16, passwords and passwordless together, Face ID filling a password, password rules and a comic's routine, and Bitwarden Send. About 35 minutes.

Episode notes

In this inspiring episode of a YSecurity.io production, we are joined by Michael Crandell, CEO of Bitwarden Inc., who shares the vision, journey, and the profound wisdom behind Bitwarden's success. Bitwarden stands at the forefront of enhancing collaboration, bolstering security, and amplifying productivity through the synergy of open source and community engagement, offering an intuitive solution for securing passwords and sensitive information.

Michael delves into the ethos of Bitwarden, emphasizing how the open-source model not only fosters innovation and transparency but also cultivates a sense of belonging and contribution among its users. He reflects on the journey of Bitwarden, from its inception to becoming a pivotal tool for individuals and organizations worldwide in managing their digital security.

Listeners will be captivated by Michael's insights into the challenges and triumphs of building a security platform that prioritizes ease of use without compromising on robustness. The conversation sheds light on the unique advantages of leveraging community feedback and collaboration to refine and evolve security solutions, underscoring the critical role of open-source principles in the dynamic landscape of cybersecurity.

This episode is a testament to the power of community-driven development and the potential of open source to revolutionize how we think about and implement security in our digital lives. Michael's vision for Bitwarden and his deep understanding of the interplay between technology, security, and community engagement offer invaluable perspectives for anyone interested in the future of cybersecurity.

Tune into this YSecurity.io production for an engaging and enlightening conversation with Michael Crandell. Whether you're deeply involved in the tech industry, passionate about open-source projects, or simply looking for effective ways to secure your digital footprint, this episode provides a compelling look at the impact of community and open source on advancing security and productivity. Join us as we explore the inspirational journey of Bitwarden and the vision that drives its mission to make the digital world a safer place for everyone.

Hosted by Jon McLachlan — co-founder of YSecurity.

The deep dive

A world where no one gets hacked

Michael Crandell, then CEO of Bitwarden: passwords that are unique and complex, the knob between security and ease of use, a free version with no catch, the trust playbook for selling to enterprises, why copying an open source app doesn't pay, end-to-end encryption next to self-hosting, four values that spell GRIT, passwords next to passwordless, and Send.

Episode 22 of The Security Podcast of Silicon Valley aired on October 1, 2022, with Jon McLachlan hosting. The guest was Michael Crandell, then CEO of Bitwarden, the open source password manager (Podbean, Apple Podcasts, Spotify). The episode is called “Michael Crandell, CEO at Bitwarden Inc., on Open Source Security.”

Jon introduced Bitwarden as an open source password manager for individuals, teams and business organizations, and Michael as Entrepreneur of the Year at the South Coast Business and Technology Award. Bitwarden’s site states the aim Michael described on the tape: “Bitwarden envisions a world where no one gets hacked” (Bitwarden).

This page follows the conversation in order: a section for each part of it, thirteen figures, eight clips from the tape, a Bitwarden video on Send, the full transcript, and five tools: a quiz, a scorecard for your team’s passwords, a calculator for what a slow security review costs, a timeline, and a to-do list. Where the decodes of the tape disagree on a word, the transcript puts its best guess in brackets, and the page doesn’t quote or retell those words.

From eFax to Bitwarden

Michael’s LinkedIn lists the path: executive vice president at eFax.com from 1996 to 2000, CEO of Celebros from 2003 to 2007, CEO and founder of RightScale from June 2007 to October 2018, a year of advising, and CEO of Bitwarden from November 2019 (LinkedIn). Wikipedia names Michael as one of RightScale’s three founders. RightScale sold software as a service for managing cloud computing across providers, and Flexera Software bought it in 2018 (Wikipedia).

On the tape, Michael had been at Bitwarden for almost three years. With software, Michael said, people sometimes forget how much quality matters in the user experience, and Bitwarden pays a lot of attention to it.

Four cards. eFax.com, 1996 to 2000: executive vice president. Celebros, 2003 to 2007: CEO. RightScale, 2007 to 2018: CEO, and one of its three founders, cloud management software, bought by Flexera in 2018. Filled, Bitwarden, from November 2019: CEO until February 2026, then an advisor. Below: between RightScale and Bitwarden, a year of advising. On the tape, Michael had been at Bitwarden for almost three years.
Michael's path to Bitwarden. Sources: LinkedIn, Wikipedia and the episode.

Unique and complex

Jon asked what problem password management solves. At a high level, Michael said, it’s about making security easy.

“We know that to be secure, a password needs to be unique and complex.”

Michael Crandell, at 2:12

Unique, so that a breach of one password doesn’t compromise the user’s other accounts. Complex, so a person can’t guess it and a computer can’t crack it. Michael put the sweet spot at about 14 characters. Together, those two qualities make passwords hard for almost anyone to remember.

A password manager creates unique, complex passwords, stores them with the websites and accounts they belong to, and fills them in for you.

“it’s a double win. It’s both more secure and easier to use”

Michael Crandell, at 3:02

That’s something the security world doesn’t often get, Michael said.

Listen · Michael Crandell on episode 22, from 2:12
About 35 seconds: Michael on unique and complex passwords, and why people can't remember them. The clip stops on its own. Read the full transcript.
Three cards. Unique: so a breach of one password doesn't open the user's other accounts. Complex: so a person can't guess it and a computer can't crack it, with a sweet spot of about 14 characters. Dashed, the problem: together, those two qualities make passwords hard for almost anyone to remember. An arrow down to a filled card, a password manager: creates unique, complex passwords, stores them with the right websites and accounts, and fills them in, more secure and easier to use. Then: "We know that to be secure, a password needs to be unique and complex." Michael, at 2:12
What a password manager solves. Source: the episode.

The knob

Jon described a knob that keeps turning up in security problems. Turn it one way and security goes up. Turn it the other way and the user’s experience improves, and the choice feels like a compromise.

“And whenever I bump into a problem like that in the security space, I think of it as a cop-out.”

Jon McLachlan, at 3:29

Jon wants both security and usability. Michael said the trade-off shows up almost everywhere in security.

“normally more secure means less convenient. So it’s a tightrope that every security product has to walk.”

Michael Crandell, at 3:48

Secure and easy to use, together, is what drew Michael to password management, and to Bitwarden.

Episode 30 takes the same question to another password manager: Dominik Schürmann of heylogin, a password manager with no master password, on why security that prevents adoption doesn’t help (episode 30).

Three cards. Turn it one way: security goes up. Turn it the other way: the user's experience improves. Filled, what Jon wants: both, since a trade-off means the problem needs a more creative answer. Below: Michael says the trade-off shows up almost everywhere in security, and every security product walks that line. A password manager is the rare tool that's more secure and easier to use at once. Then: "normally more secure means less convenient." Michael, at 3:48
The knob between security and ease of use. Source: the episode.

Built by one founder

Michael joined a company that Kyle Spearrin had already founded. Kyle, the founder and CTO, built Bitwarden alone, set out to do better than the competition, and made it open source. Starting a company often means quitting a job, Michael said, and that carries risk.

Bitwarden’s first release came on August 10, 2016: apps for iOS and Android, browser extensions for Chrome and Opera, and a web vault (Wikipedia).

Don’t break what works

Jon asked what it was like to come in as CEO next to a founder who was also the CTO.

“One of my mantras when I joined Bitwarden was not to screw up anything that’s already working.”

Michael Crandell, at 5:26

What Kyle had built was simple. It does what you need, does no more, and stays out of your way. It was open source and built around a community, and the company kept growing that community around the world. Anyone can look at the code, review it, vet it and contribute to it, and many people do. Jon’s view: enable people, and participation becomes power.

The best day

Michael’s best day was every day, an answer Michael called a little corny. More seriously, it was the first time a support email came in thanking Bitwarden for the product and cheering the team on. Most support messages are about problems and complaints. Bitwarden gets messages of “Bitwarden love” almost every day.

They come from the free version, full-featured and free forever, in keeping with open source. Many people sign up for the paid version as a way to support the work of keeping people safe online. It’s a core belief at Bitwarden that everybody has the right to be safe online, Michael said.

“Everybody should have that right.”

Michael Crandell, at 7:26

Listen · Michael Crandell on episode 22, from 6:34
About 30 seconds: Michael on the support emails that thank Bitwarden. The clip stops on its own. Read the full transcript.

Nobody is the product

Jon pointed out that Bitwarden needs back-end components to run. Anyone could run all of it, since it’s open source, but a SaaS that’s set up and ready to go, for free, is convenient.

Michael tied the free version to that aim. Some people hear “free” and suspect a trick: the users are the product, or someone sells ads against their data.

“We don’t track users, we don’t capture any information.”

Michael Crandell, at 8:44

Free users who love the product tell others, and many bring Bitwarden to work. That’s where Bitwarden makes its money, mostly with business versions: Enterprise for the largest companies, and Teams for smaller ones.

Four boxes joined by arrows. Free version: free forever. People love it, and tell others. Brought to work: Teams, Enterprise. Filled, revenue: business versions. Below: Teams serves smaller businesses, and Enterprise serves the largest companies. Some free users sign up for the paid version anyway, to support the work. No tracking of users, and no information captured about them. Then Bitwarden's press room today: "Bitwarden envisions a world where no one gets hacked."
How a free version pays, as Michael described it. Sources: the episode and Bitwarden.

From consumer to business

Jon asked whether Michael helped Bitwarden pivot from consumers to businesses. Michael helped the emphasis. Kyle had already built the Teams and Enterprise versions, and Michael knew from experience what enterprises need and want.

One of the first things Michael did was build up Bitwarden’s security and compliance profile:

  • A SOC 2 and SOC 3 audit, and the discipline of those practices, so customers could trust Bitwarden.
  • A HIPAA audit.
  • More frequent penetration tests and source code audits.
  • GDPR and CCPA compliance, for privacy.
  • An SLA for larger customers.

“This is not a brand new playbook, but it’s one that I had been through.”

Michael Crandell, at 10:43

Michael sent listeners to bitwarden.com/compliance. As of November 11, 2026, that page lists ISO 27001, SOC 2 and SOC 3, HIPAA, CCPA and CPRA, GDPR, and the Data Privacy Framework. It also lists annual source code audits and penetration tests for each client, annual network security assessments, and a bug bounty on HackerOne (Bitwarden). Wikipedia notes a security assessment, code audit and cryptographic analysis by Cure53 in October 2018 (Wikipedia).

GDPR is a European Union regulation on information privacy, adopted on April 14, 2016 and in effect since May 25, 2018 (Wikipedia). The California Consumer Privacy Act was signed on June 28, 2018 and took effect on January 1, 2020 (Wikipedia).

Two rows of cards. Filled, SOC 2 and SOC 3: an audit, and the discipline of its practices, so customers could trust Bitwarden. HIPAA: an audit. Tests and audits: penetration tests and source code audits, more often. Privacy: GDPR and CCPA compliance. An SLA: for larger customers, who expect one. A page for it: bitwarden.com/compliance, with the certifications and measures. Below: as of November 11, 2026, that page lists ISO 27001, SOC 2 and SOC 3, HIPAA, CCPA and CPRA, GDPR and the Data Privacy Framework, plus annual source code audits and penetration tests for each client, and a bug bounty. Then: "This is not a brand new playbook, but it's one that I had been through." Michael, at 10:43
The trust playbook Michael brought to Bitwarden. Sources: the episode and Bitwarden.

Lean in with the security team

At larger companies, Michael learned, several teams review a purchase: usually a security team, the business folks, procurement and IT.

“with security teams, you either kind of lean in and get a sense of trust early on, or you don’t.”

Michael Crandell, at 11:48

Lean in, and the path tends to be smoother. Otherwise you fight a losing battle, because you haven’t done what their policies require. Michael called that understandable, since they all have policies to follow. Jon agreed: security teams have a tough job, they’re in the same community, and they’re trying to protect their business.

Jon, who has worked on many business-to-business plays, called the certifications Michael listed serious contributions to a product’s security, more than checkboxes. The calculator further down puts a number on a review that stalls.

Four compartments: filled, security team, then business, procurement and IT. Below, two cards. Filled, lean in early: trust comes early, and the path tends to be smoother. Dashed, hold back: a losing battle, because you haven't done what their policies require. Then: "with security teams, you either kind of lean in and get a sense of trust early on, or you don't." Michael, at 11:48
Who reviews a purchase at a larger company. Source: the episode.

A worst day with a template

Jon asked about a worst day. Michael has one, and it repeats.

“It’s the same day over and over.”

Michael Crandell, at 12:43

Government agencies, in the U.S. or overseas, contact Bitwarden about data breaches that are being exposed on the dark web. You can hardly read the news without a new breach or a ransomware attack. What bothers Michael most is a breach that came from insecure password practices and could have been avoided. Rolling out password management at a company is simple, and so is signing up yourself.

Jon shares the feeling. The technology exists to stop nearly every kind of breach, Jon said, and it takes effort to commit to raising the security bar. Michael takes it as motivation to get more people onto the platform.

Listen · Michael Crandell on episode 22, from 12:46
About 40 seconds: Michael on the worst day that repeats. The clip stops on its own. Read the full transcript.

What sets Bitwarden apart

Jon asked what makes Bitwarden special. Michael’s list:

  • Open source. Developers and security professionals around the world vet the product, and anyone can read every line of code.
  • Versions for the largest enterprises, with integrations for single sign-on and directory services.
  • Self-hosting, for companies that want it.
  • Versions for everyone from big companies to individual users.
  • A full-featured free version, free forever, with no strings attached.

The free version helped build a community of over 5 million users, by Michael’s count on the tape. The product has been translated into almost 50 languages, largely by that community.

Jon wondered aloud why anyone would use anything else. Michael said Bitwarden wonders that sometimes too.

A numbered list. 1, open source: developers and security professionals around the world vet it, and anyone can read every line of code. 2, versions for the largest enterprises, with single sign-on and directory services. 3, self-hosting, for companies that want it. 4, versions for everyone, from big companies to individual users. 5, a full-featured free version, free forever, with no strings attached. Below, two numbers: over 5 million users, by Michael's count on the tape, and almost 50 languages, translated largely by the community.
What sets Bitwarden apart, in Michael's list. Source: the episode.

Couldn’t someone copy it?

Jon asked the naive question: with the code open, couldn’t someone copy the whole business? In a way, Michael said. Open source licenses require whoever copies the code to open source what they build too. It hasn’t happened much.

“we try to remember that imitation is the sincerest form of flattery.”

Michael Crandell, at 17:21

Wikipedia lists Bitwarden’s licenses: AGPL-3.0 for the server, GPL-3.0 for the clients, and proprietary terms for some modules (Wikipedia).

What open source gives Bitwarden, as Michael put it:

  • Anyone can check the encryption. People can see how Bitwarden handles sensitive data, how it encrypts and where. They can confirm that all their data is end-to-end encrypted, so Bitwarden can’t touch it. Researchers look at it.
  • Anyone can build on it. People contribute, build on the code and add modules.
  • Larger companies prefer it. Open source reduces their risk and their cost. If a provider goes away, they still have the source code.

The danger to the business is small, because so few people build Bitwarden from scratch to use it. Traditional open source was infrastructure. In the days of MySQL, people downloaded the database, built it and ran it. Bitwarden is an app with admin features and eight or 10 clients: iOS, Android, Windows, Mac, Linux, five or six browsers and a command line. Building and running all of that isn’t worth it against the license cost and support, and IT managers would rather license it.

MySQL is a free and open-source relational database. Its first version appeared on May 23, 1995 (Wikipedia).

Jon’s answer: let the people who wrote the software run it.

“They know it best. They know how to configure it.”

Jon McLachlan, at 20:05

A multi-tenant service is more efficient, Jon added, and passes the savings and the expertise on to every customer.

“We get the benefit of open source, but we don’t really have to compete against ourselves.”

Michael Crandell, at 20:17

Listen · Michael Crandell on episode 22, from 19:05
About 30 seconds: Michael on why companies license an open source app. The clip stops on its own. Read the full transcript.
Two cards. Traditional open source: infrastructure, and in the days of MySQL, people downloaded the database, built it and ran it. Filled, Bitwarden: an app with admin features and eight or 10 clients, iOS, Android, Windows, Mac, Linux, five or six browsers and a command line. Below: the licenses require anyone who copies the code to open source what they build too. Larger companies prefer open source: less risk, less cost, and the code stays if a provider goes away. Building and running all those clients isn't worth it against the license cost and support, so IT managers license it. Then: "We get the benefit of open source, but we don't really have to compete against ourselves." Michael, at 20:17
Why copying an open source app doesn't pay. Sources: the episode and Wikipedia.

End to end, or on your own servers

Jon asked a follow-up. If everything is end-to-end encrypted and Bitwarden can’t see the data, why would a business run the whole stack on its own servers?

End-to-end encryption means nobody in between, in transit or in storage, can see your data, and neither can the company that provides the product, Michael said.

“We just do not have access to it, because it’s encrypted.”

Michael Crandell, at 21:35

Michael called it a zero-knowledge approach, popular over the last half dozen years. Some companies still want to self-host, sometimes for regulatory reasons. A company in Switzerland, for example, may have to keep all its data inside Swiss borders. That’s data residency, and running the server there meets it. Bitwarden found it productive to skip arguments with customers about which way they want, and to offer both.

Jon keeps hearing about data governance and data residency, and hopes storage can sit behind a layer that keeps multi-tenancy and still meets those rules. Michael expects more of it, with privacy requirements coming from the EU.

Listen · Michael Crandell on episode 22, from 21:48
About 35 seconds: Michael on why some companies self-host anyway. The clip stops on its own. Read the full transcript.
Two cards. End-to-end encrypted service: nobody in between, in transit or in storage, can see the data, and neither can the provider, a zero-knowledge approach. Self-hosted: the company runs the server where it needs to, for example a company in Switzerland keeping its data inside Swiss borders. An arrow down to a filled card: Bitwarden offers both, and skips the argument about which one a customer should want. Then: "We just do not have access to it, because it's encrypted." Michael, at 21:35
End-to-end encryption and self-hosting, side by side. Source: the episode.

A remote company that spells GRIT

Jon asked what joining Bitwarden would feel like. They’d love to have Jon, Michael said. Bitwarden was fully remote, with people in about 22 U.S. states, 20 or more countries and six continents. That let the company hire the best people from almost anywhere in the world, and lean into diversity on the team. A global customer base calls for a global team.

The company had four values: gratitude, responsibility, inclusion and transparency.

“But together, they spell the word grit, which I think is really necessary.”

Michael Crandell, at 24:32

A company that lasts and keeps innovating needs staying power, Michael said, because not all of it is easy. Jon liked the word for the entrepreneurial mindset it brings.

Listen · Michael Crandell on episode 22, from 24:12
About 40 seconds: Michael on four values that spell GRIT. The clip stops on its own. Read the full transcript.
Four compartments spelling GRIT. Filled, G: gratitude. R: responsibility. I: inclusion. T: transparency. Below: fully remote at the time, about 22 U.S. states, 20 or more countries, six continents. Hiring from almost anywhere, for a global customer base. A company that lasts needs staying power, because not all of it is easy. Then: "But together, they spell the word grit, which I think is really necessary." Michael, at 24:32
Four values, one word. Source: the episode.

The interview question about age 16

Michael still interviewed everyone who joined Bitwarden. Outsiders may think a technology company is all about technical wizardry, Michael said, but people build the technology. Michael’s question for every candidate: what did you like to do when you were 16 years old?

“You tend to get authentic answers, because it’s not a question that anyone rehearses for in a job interview.”

Michael Crandell, at 25:56

The question isn’t hard, and it shows something about the candidate as a person. Jon liked that it has nothing to do with the technical pieces, and that it lets a candidate share a passion that’s still there.

Passwords and passwordless

Jon asked about all the talk of going passwordless.

“First, passwords are not going away.”

Michael Crandell, at 26:48

Passwords are built into so much of computing that changing all those systems will take a long time. Passwordless technologies are already here and useful: biometrics such as Touch ID, Face ID and Android biometrics, and security keys. Bitwarden supported the common ones and planned to keep up as passwordless evolves.

“So we look at it really as an and, not an or.”

Michael Crandell, at 27:34

People will want tools that let them use the best method each time. Kyle has a saying about the company’s name: there’s a reason the word pass, or password, isn’t in it. The larger goal is helping people authenticate safely online, with a password or without one.

WebAuthn is the W3C web standard that websites use to sign people in with WebAuthn credentials, commonly known as passkeys. Its first level became a W3C Recommendation on March 4, 2019 (Wikipedia). Episode 61 goes back to the start: Taher Elgamal, known as the father of SSL, on how the password became the way everyone logs in (episode 61).

Listen · Michael Crandell on episode 22, from 27:34
About 30 seconds: Michael on passwords and passwordless together, and the name Bitwarden. The clip stops on its own. Read the full transcript.
Three cards. Passwords: built into so much of computing that changing those systems will take a long time. Passwordless, already here: biometrics such as Touch ID, Face ID and Android biometrics, and security keys. Filled, both: tools that let people use the best method each time. Below: on an iPhone, Face ID opens Bitwarden and Bitwarden fills the password, a passwordless experience on a password site. Underneath, a secret or a certificate still passes. Kyle Spearrin's point: the name Bitwarden has no pass or password in it, and the goal is signing in safely, with a password or without one. Then: "So we look at it really as an and, not an or." Michael, at 27:34
Passwords and passwordless, together. Source: the episode.

Face ID fills the password

One of Michael’s favorite features is on the iPhone. Password managers can plug into the phone’s password autofill. On a site that asks for a password, Michael taps the password button, Bitwarden comes up, Face ID opens it, and the password fills in.

“So even though it’s a password-based site, the experience is pretty much passwordless”

Michael Crandell, at 28:53

Jon pointed to what sits underneath: secure enclaves and protected memory in iOS that users never think about. Episode 92 goes further into that hardware, with Jasson Casey of Beyond Identity on the secure coprocessors already in phones and laptops (episode 92).

At the bottom of it all is still a secret, Michael added: a certificate, or something like a password, that passes under the covers. Most people aren’t opinionated about technology. They want to get their work done the quickest, easiest way. So make the password site easy, and make the passwordless one easy too.

Episode 19 makes a related point from the identity side: Aaron Painter of Nametag on why passkeys still validate the device (episode 19).

Password rules, and a comic

Jon’s pet peeve: password rules that cap length at around 32 characters and demand certain kinds of characters, so you hit reset on your password manager’s generator until a password fits.

Michael knew a comic’s routine on how those rules evolved. In the beginning, everyone had one password and used it everywhere. Then sites said that wasn’t secure enough and asked for a capital letter, so everyone capitalized the first letter. The routine moves on to special characters, numbers and the rest. It got laughs because it’s what everybody did.

Send, and what’s next

Michael’s picture of success started with password management, where Bitwarden had grown fast for a couple of years and planned to keep up the pace of innovation. Beyond that: more tools and products for developers, and more passwordless authentication.

Then the adjacencies, such as Bitwarden Send. It sends a piece of text or a file, end-to-end encrypted, to anyone, whether they use Bitwarden or not, with the same zero-knowledge trust as the rest of the product. You can set an expiration date. Companies like that, because they don’t want data piling up that a deposition or another legal proceeding could expose.

“They want to know that things are temporary.”

Michael Crandell, at 33:13

Michael compared it to the tape recording that self-destructed in the Mission Impossible TV series: the message gets through, then goes away. Larger companies were asking for more of it. All of it sits under one aim: helping people stay safe online and do business faster, safely, starting with authentication that’s simple, secure and convenient.

Jon would use it to give a guest the Wi-Fi password for the day, so the password isn’t left on a phone that later gets lost.

Wikipedia describes Send the same way: end-to-end encrypted text in the free version, and files in the paid versions (Wikipedia). Bitwarden’s own video walks through a send, with options for an expiration date, access limits and a password.

Bitwarden's video on Send, under two minutes, posted on June 26, 2026. Bitwarden made it. Watch on YouTube.
Listen · Michael Crandell on episode 22, from 32:39
About 35 seconds: Michael on Bitwarden Send. The clip stops on its own. Read the full transcript.
Four boxes joined by arrows. Text or a file, your choice. Encrypted, end to end. To anyone, Bitwarden user or not. Filled, then gone, on the date you set. Below: companies don't want data piling up that a deposition or another legal proceeding could expose. Wikipedia: text in the free version, files in the paid versions. Jon's use: the Wi-Fi password for a guest, for the day. Then: "They want to know that things are temporary." Michael, at 33:13
Send: a message that expires. Sources: the episode and Wikipedia.

Come have a look

“Please come have a look at Bitwarden. It’s free.”

Michael Crandell, at 34:35

Don’t get caught out by a password mishap, Michael said. Once you start, you get an aha moment, where security and ease of use come together, and you won’t go back.

What happened after the tape

A $100 million round. On September 6, 2022, Bitwarden announced a $100 million growth investment led by PSG, with Battery Ventures taking part (Business Wire, Wikipedia). The episode came out on October 1.

Passwordless.dev joined Bitwarden. In January 2023, Bitwarden bought the Swedish startup, which gave developers an open-source way to add passwordless sign-in based on WebAuthn and FIDO2. Bitwarden also launched a beta that lets other developers add Touch ID, Face ID and Windows Hello sign-in to their apps (TechCrunch, Wikipedia). Both match what Michael named for the future: tools for developers, and passwordless.

Audit reports went public. In February 2023, Bitwarden released network security and security assessment reports by Cure53, from work done in May and October 2022 (Wikipedia).

An authenticator of its own. On May 1, 2024, Bitwarden launched Bitwarden Authenticator, a multi-factor authentication app (Wikipedia, Android Authority).

A bug that raised questions. In October 2024, a change to the desktop app’s dependencies added a restricted-use SDK that could stop some people from building the app from source, and some worried Bitwarden was moving away from open source. Kyle Spearrin called it “merely a bug” the company planned to resolve (The Register, Wikipedia).

Michael stepped down in February 2026. Michael Sullivan replaced Michael as CEO (Wikipedia), and Michael’s LinkedIn lists an advisor role at Bitwarden since then (LinkedIn).

From 5 million to 15 million. On July 28, 2026, Bitwarden said it had passed 15 million users and 80,000 businesses (Business Wire). On the tape, Michael counted over 5 million.

A timeline. September 6, 2022, $100 million: a growth investment, led by PSG. October 1, 2022, episode 22: Michael on the show. January 2023, Passwordless.dev: Bitwarden buys it, for developers adding passwordless sign-in. February 2023, audit reports: Cure53 reports from May and October 2022 go public. May 1, 2024, an authenticator: Bitwarden Authenticator, for multi-factor authentication. October 2024, an SDK question: a dependency change raises open source questions, and Kyle Spearrin calls it a bug. February 2026, a new CEO: Michael Sullivan takes over, and Michael stays on as an advisor. July 28, 2026, 15 million users: and 80,000 businesses, and on the tape, Michael counted over 5 million.
After the tape: a funding round, Passwordless.dev, audit reports, an authenticator, a new CEO and 15 million users. Sources: Business Wire, TechCrunch, Wikipedia and LinkedIn.

Did you catch it? A seven-question quiz

Seven questions from the episode. Each answer links the moment in the transcript or its section.

Quiz · seven questions

Did you catch it?

Pick an answer to see whether you caught it.

  1. What two qualities does a secure password need, in Michael's words?

    a. "We know that to be secure, a password needs to be unique and complex." Transcript, 2:12.

  2. Where did Michael put the sweet spot for password length?

    c. Long enough, and still easy with a password manager. See Unique and complex.

  3. What was one of Michael's mantras on joining Bitwarden?

    b. "One of my mantras when I joined Bitwarden was not to screw up anything that's already working." Transcript, 5:26.

  4. Where does Bitwarden make its money, as Michael described it?

    c. Free users bring Bitwarden to work. See Nobody is the product.

  5. Why don't companies build Bitwarden from its open source code to save the license?

    a. IT managers would rather license it. See Couldn't someone copy it?.

  6. What did Bitwarden's four values spell?

    b. "But together, they spell the word grit, which I think is really necessary." Transcript, 24:32.

  7. How does Michael see passwords and passwordless?

    a. "So we look at it really as an and, not an or." Transcript, 27:34.

How safe are your team’s passwords?

Eight questions on how your team makes, stores and shares passwords, built from the episode. Each tip links the section behind it.

Scorecard · eight questions

How safe are your team's passwords?

Answer for your team as it works today. If two answers fit, pick the lower one.

  1. Does everyone on your team use a password manager?

    • No
    • Some of us
    • Yes, everyone

    A password manager makes passwords more secure and easier to use at once. See Unique and complex.

  2. Is every account's password unique?

    • No, many are reused
    • Mostly
    • Yes, every one

    A unique password keeps one breach from opening other accounts. See Unique and complex.

  3. Who makes new passwords?

    • People, from memory
    • People, following rules
    • A generator, long and random

    Michael put the sweet spot at about 14 characters. See Unique and complex.

  4. Is your password manager tied to single sign-on and your directory?

    • No
    • Partly
    • Yes

    The largest companies ask for those integrations first. See What sets Bitwarden apart.

  5. Do people sign in with biometrics or a security key where they can?

    • No
    • Some do
    • Yes

    Passwords and passwordless work together. See Passwords and passwordless.

  6. How do people share a password or a sensitive file?

    • In chat or email
    • In a shared vault, with some chat
    • Encrypted, with an expiration date

    What expires can't pile up in inboxes. See Send, and what's next.

  7. Would you know if your team's accounts turned up in a breach?

    • No
    • Only from the news
    • Yes, we watch for it

    Michael's worst day is a breach notice that repeats. See A worst day with a template.

  8. Do your own password rules allow long passwords without character games?

    • No, short limits and character rules
    • Some of both
    • Yes

    Rules that cap length push people into games. See Password rules, and a comic.

Reused and remembered

Passwords live in people's heads and get reused. Start with a password manager for everyone, and unique passwords from a generator.

Getting there

Most passwords are stored and unique. Tie the manager to single sign-on, and move sharing to links that expire.

Unique, stored and shared safely

Keep biometrics and security keys in the mix, and watch for breaches that name your accounts.

What does a slow security review cost?

Michael’s advice for selling to larger companies: lean in with their security team early, or fight a losing battle. This calculator puts a number on a review that drags.

Calculator

What does a slow security review cost?

Four numbers: deals a quarter that go through a buyer's security review, what a deal is worth, the weeks a review adds, and the share of those deals that stall out.

$192,000a year in deals that stall
$480,000a quarter waiting on review
48deal-weeks of delay a quarter
$48,000a quarter in deals that stall

At 8 deals a quarter worth $60,000 each, $480,000 waits on security review every quarter. At 6 weeks each, that's 48 deal-weeks of delay. If 10% stall out, that's $48,000 a quarter, $192,000 a year.

The calculator counts a stalled deal as lost and four quarters to a year. The default numbers are placeholders, yours to change. Michael gave no figures for these on the tape.

From eFax to 15 million users

Michael’s path, Bitwarden’s history, the field around it, and this show. Filter by topic.

Timeline

From eFax to 15 million users

  1. MySQL

    The first version of the open-source database appears (Wikipedia, on this page).

  2. eFax.com

    Michael becomes executive vice president (LinkedIn).

  3. Celebros

    Michael becomes CEO (LinkedIn).

  4. RightScale

    Founded, with Michael among its three founders (Wikipedia).

  5. GDPR adopted

    The European Union's information privacy regulation (Wikipedia).

  6. Bitwarden's first release

    Apps for iOS and Android, extensions for Chrome and Opera, and a web vault (Wikipedia).

  7. Flexera buys RightScale

    Michael ran it as CEO until October (Wikipedia, LinkedIn).

  8. GDPR takes effect

    Two years after adoption (Wikipedia).

  9. CCPA signed

    California's consumer privacy law (Wikipedia).

  10. A Cure53 audit

    Security assessment, code audit and cryptographic analysis (Wikipedia).

  11. WebAuthn

    Level 1 becomes a W3C Recommendation (Wikipedia, on this page).

  12. Michael joins Bitwarden

    As CEO (LinkedIn).

  13. CCPA takes effect

    California's consumer privacy law goes into force (Wikipedia).

  14. Episode 19

    Aaron Painter of Nametag on why a password is not a passport (episode page).

  15. $100 million

    A growth investment led by PSG (Business Wire).

  16. Episode 22

    Michael on the show (Podbean, transcript).

  17. Passwordless.dev

    Bitwarden buys the Swedish startup (TechCrunch).

  18. Cure53 reports

    From assessments in May and October 2022 (Wikipedia).

  19. Episode 30

    Dominik Schürmann of heylogin, a password manager with no master password (episode page).

  20. Bitwarden Authenticator

    A multi-factor authentication app (Wikipedia).

  21. An SDK question

    Kyle Spearrin calls the dependency change a bug (The Register).

  22. Episode 61

    Taher Elgamal on how the password became the way everyone logs in (episode page).

  23. A new CEO

    Michael Sullivan replaces Michael, who stays on as an advisor (Wikipedia, LinkedIn).

  24. Episode 92

    Jasson Casey of Beyond Identity on identity as the security boundary (episode page).

  25. A video on Send

    Bitwarden posts a walkthrough (YouTube, on this page).

  26. 15 million users

    And 80,000 businesses (Business Wire).

What to do this week

Five things, in the order of the episode.

  1. Count the reused passwords. Find the accounts your team protects with the same password, as in Unique and complex.
  2. Give everyone a password manager. Tie it to single sign-on and your directory, as in What sets Bitwarden apart. The scorecard shows where else to look.
  3. Share secrets that expire. Move passwords and sensitive files out of chat and email, as in Send, and what’s next.
  4. Prepare for the buyer’s review. Line up the reports, the tests and a page that shows them before a buyer’s security team asks, as in From consumer to business, and run your numbers through the calculator.
  5. Get help with it. Our Sales Support team answers security questionnaires and joins buyer calls as your security team, and SOC 2 Type 2 gets you to an audit report in as little as five months. Penetration Testing gives you the tests buyers ask for, and vCISO Services gives you a security leader to set priorities. If you want to talk it through, book 15 minutes with us.

Key takeaways

  1. Unique and complex, and easier

    A secure password is unique, so one breach doesn't open other accounts, and complex, so nobody can guess or crack it. Michael put the sweet spot at about 14 characters. Those qualities make passwords hard to remember, and a password manager makes them more secure and easier to use at once.

  2. Treat a trade-off as a hint

    Jon calls the knob between security and usability a cop-out, a sign the problem needs a more creative answer. Michael calls it a tightrope every security product walks, and a password manager is a rare tool that wins on both.

  3. Don't break what works

    Michael's mantra on joining Bitwarden: keep what Kyle Spearrin built. A simple product that stays out of the way, open source, and a community that reviews, vets and contributes.

  4. A free version can pay for itself

    Bitwarden's free version is full-featured and free forever, with no tracking. Free users tell others and bring Bitwarden to work, and the business versions, Enterprise and Teams, make the money.

  5. Earn the security team's trust early

    To sell to enterprises, Michael built up SOC 2 and SOC 3, a HIPAA audit, more pen tests and source code audits, GDPR and CCPA, an SLA and a compliance page. Lean in with the buyer's security team early, or fight a losing battle.

  6. Open source sells to enterprises

    Open source lets anyone check how the encryption works, invites contributions, and lowers a customer's risk and cost. Almost nobody builds an app with eight or 10 clients from scratch, so companies license it.

  7. Offer both, and skip the argument

    End-to-end encryption means nobody in between, and not the provider, can see the data. Some companies still need to self-host, for data residency or other rules, so Bitwarden offers both.

  8. Passwords and passwordless, together

    Passwords aren't going away, and passwordless is already here. Use the best method each time. Face ID can open a password manager that fills a password, and a secret still passes underneath.

Chapters

Tap a chapter to play from there.

Pull quotes

“We know that to be secure, a password needs to be unique and complex.”

Michael Crandell ·

“it's a double win. It's both more secure and easier to use”

Michael Crandell ·

“And whenever I bump into a problem like that in the security space, I think of it as a cop-out.”

Jon McLachlan ·

“normally more secure means less convenient. So it's a tightrope that every security product has to walk.”

Michael Crandell ·

“One of my mantras when I joined Bitwarden was not to screw up anything that's already working.”

Michael Crandell ·

“Everybody should have that right.”

Michael Crandell ·

“We don't track users, we don't capture any information.”

Michael Crandell ·

“This is not a brand new playbook, but it's one that I had been through.”

Michael Crandell ·

“with security teams, you either kind of lean in and get a sense of trust early on, or you don't.”

Michael Crandell ·

“It's the same day over and over.”

Michael Crandell ·

“we try to remember that imitation is the sincerest form of flattery.”

Michael Crandell ·

“They know it best. They know how to configure it.”

Jon McLachlan ·

“We get the benefit of open source, but we don't really have to compete against ourselves.”

Michael Crandell ·

“We just do not have access to it, because it's encrypted.”

Michael Crandell ·

“But together, they spell the word grit, which I think is really necessary.”

Michael Crandell ·

“You tend to get authentic answers, because it's not a question that anyone rehearses for in a job interview.”

Michael Crandell ·

“First, passwords are not going away.”

Michael Crandell ·

“So we look at it really as an and, not an or.”

Michael Crandell ·

“They want to know that things are temporary.”

Michael Crandell ·

“Please come have a look at Bitwarden. It's free.”

Michael Crandell ·

About the guest

Michael Crandell, Former CEO, Bitwarden

Michael Crandell was CEO of Bitwarden, the open source password manager, from November 2019 to February 2026, and has been an advisor to the company since, according to Michael's LinkedIn. Before Bitwarden, Michael was executive vice president at eFax.com, CEO of Celebros, and CEO of RightScale, a cloud management company Michael founded with two others and led until Flexera bought it in 2018. On this episode, Jon introduced Michael as Entrepreneur of the Year at the South Coast Business and Technology Award.

About the host

Jon McLachlan is co-founder of YSecurity, the on-demand cybersecurity team for startups, and of Cyberbase.ai. The Security Podcast of Silicon Valley is hosted by Jon McLachlan and Sasha Sinkevich. Jon McLachlan on LinkedIn ↗

Context and sources

  • Episode 22 on Podbean: Michael Crandell, CEO at Bitwarden Inc., on Open Source Security. Source ↗
  • Michael Crandell on LinkedIn: eFax.com from 1996, Celebros from 2003, RightScale from 2007 to 2018, Bitwarden CEO from November 2019 to February 2026, and advisor since. Source ↗
  • Bitwarden's compliance page, read November 11, 2026: ISO 27001, SOC 2 and SOC 3, HIPAA, CCPA and CPRA, GDPR, the Data Privacy Framework, annual source code audits and penetration tests, and a bug bounty. Source ↗
  • Bitwarden's press room: Bitwarden envisions a world where no one gets hacked. Source ↗
  • Business Wire (September 6, 2022): Bitwarden announces a $100 million growth investment led by PSG. Source ↗
  • TechCrunch (January 18, 2023): Bitwarden acquires Passwordless.dev to help companies authenticate users without passwords. Source ↗
  • Android Authority: Bitwarden launches its own free and open-source Authenticator app. Source ↗
  • The Register (October 24, 2024): concerns about a new SDK requirement in the Bitwarden desktop app. Source ↗
  • Business Wire (July 28, 2026): Bitwarden passes 15 million users and 80,000 businesses. Source ↗
  • Bitwarden on YouTube: Securely share sensitive information with Bitwarden Send, posted June 26, 2026. Source ↗
  • Wikipedia, Bitwarden: first released August 10, 2016 by Kyle Spearrin, its licenses, Send, its audits, its funding, Passwordless.dev, Bitwarden Authenticator, and the change of CEO in February 2026. Source ↗
  • Wikipedia, RightScale: cloud management software, founded in 2006 by three founders including Michael Crandell, and acquired by Flexera Software in 2018. Source ↗
  • Wikipedia, General Data Protection Regulation: adopted April 14, 2016, in effect since May 25, 2018. Source ↗
  • Wikipedia, California Consumer Privacy Act: signed June 28, 2018, in effect since January 1, 2020. Source ↗
  • Wikipedia, WebAuthn: the W3C web standard for WebAuthn credentials, commonly known as passkeys. Level 1 became a W3C Recommendation on March 4, 2019. Source ↗
  • Wikipedia, MySQL: a free and open-source relational database. The first version appeared on May 23, 1995. Source ↗

Transcript

Automatic transcription. Jon McLachlan hosts this episode with Michael Crandell, then CEO of Bitwarden. There is no diarization on the tape, so speaker labels were assigned from the content and checked against reference recordings of each voice from this episode, and a few short lines may sit with the wrong speaker. Names and terms were normalized where the recognizer misheard them (Jon McLachlan, Bitwarden, Kyle Spearrin, SaaS). Words in [brackets] are best guesses where the audio is unclear, and [...] marks words no decode made out. Speech is transcribed as spoken, though many repeated words and false starts are left out, and so are short backchannels such as "yeah" where they overlap the other speaker.

Read the full transcript 5,705 words

Jon McLachlan

Welcome everyone to another show. I'm here today with a very special guest, Michael Crandell, the CEO of Bitwarden. And for those of you who are less familiar with Bitwarden, Bitwarden is an open source password management solution for individuals, teams, and business organizations. Michael was named Entrepreneur of the Year at the South Coast Business and Technology Award. It's great to have you on the show, Michael.

Michael Crandell

Thanks. It's a pleasure to be here, Jon.

Jon McLachlan

So a lot of times the guests on this show will have some sort of a story or connection with their childhood, maybe something that really happened or brought about a formative moment way back in the day, something that really happened that makes you or led to sort of an interest in security. I'm curious, do you have any stories like that?

Michael Crandell

That's a great question. I think back when I was a kid, my mom let me take apart a bicycle, 100% take it apart to every single piece, and then put it back together, you know, kind of clean the pieces, oil them, et cetera. It really gave me an understanding of how component parts go together to create a whole. And also, maybe more importantly, how paying attention to the quality at the detail level ends up producing a much better product as a finished product. You know, I think that applies to many product-focused businesses, but certainly software development. So I see a big relevance there.

Jon McLachlan

Yeah, absolutely. Especially connecting the details to a user experience or how something might work.

Michael Crandell

Yeah, I mean, sometimes we forget about how important quality is in the user experience with software. And it's something we try to pay a lot of attention to with Bitwarden.

Jon McLachlan

And so speaking of Bitwarden, I like to think we've all heard about password management systems, but maybe you can share from your point of view, what's the core of password management? So what is that problem? What are we solving really, when we get right down to it?

Michael Crandell

At a high level, it's about making security easy. We know that to be secure, a password needs to be unique and complex. So it needs to be unique so that, should it somehow be breached, it doesn't compromise any other accounts that a user has. And it needs to be complex so that it can't be easily guessed or cracked by a computer. By the way, a sweet spot for uncrackable passwords, or very long time to crack a password, is about 14 characters long. But those two qualities make it hard to remember for almost everyone. [So] a password manager creates unique complex passwords for you, and it stores them in relation to the websites and accounts that you use, and then it pulls them up and automatically enters them for you. So in the end of the day, it's a double win. It's both more secure and easier to use, which is something that you don't often get in the security world.

Jon McLachlan

That's right. You know, oftentimes I find that when you bump into a problem in security, you find that you have a little knob, and you can turn that knob one way and it increases your security. And if you turn it the other way, it's actually increasing your user performance, and it almost feels like a compromise. And whenever I bump into a problem like that in the security space, I think of it as a cop-out. You know, we're just not being creative enough, we're not thinking about the problem the right way to have both, because I want both security and usability.

Michael Crandell

It's a nasty trade-off. It's almost omnipresent in security. I mean, normally more secure means less convenient. So it's a tightrope that every security product has to walk. And it was one of the things that really attracted me to password management and Bitwarden in particular, was the combination of secure and easy to use.

Jon McLachlan

And you've been with Bitwarden for almost three years now, right?

Michael Crandell

Almost three years, that's right. That's a pretty good chunk of time. It seems to have gone by fast. It's, we've been growing super fast, and a lot has been accomplished. By the way, I joined a company that was already founded by our founder and CTO, Kyle Spearrin. And he's an amazing guy with an amazing story. He basically built it single-handedly, by himself, based on the principle that he could do something better than the competition and, [in] a key insight, make it open source.

Jon McLachlan

Wow. So he really had that entrepreneurial drive and spirit, strong ownership.

Michael Crandell

Absolutely. As the story goes, he, you know, when you start a company, often you're leaving another job. So it's the old story, quit the job, start a new company. There's risk associated with that. I thought he was brilliant. Apparently he popped that question to his wife while they were both on a 5K run, which pretty much guarantees that you're not going to have a long conversation about it anyway. And she said, [gasp], and the rest is history.

Jon McLachlan

That's amazing. Yeah, 5K is about, what, 15 minutes or so? Yeah. So coming in as CEO and working with a founder CTO, what was that experience like?

Michael Crandell

It's been wonderful. One of my mantras when I joined Bitwarden was not to screw up anything that's already working. And what was already in place, what Kyle had built, was a system that was simple. It does what you need and doesn't do more and doesn't get in your way. It was open source, and it was very community-based. So Kyle did a great job, and I think we've continued that work in fostering a strong global community around the product. And of course, being open source helps a lot with that, because anyone can participate. Anyone can look at what we've done. They can review the code, they can vet it, and many people do. And they can also contribute to make it better.

Jon McLachlan

That's spectacular. That's how you build community, enable people, and then participation really becomes power in that sense.

Michael Crandell

Exactly. Exactly. I think one of your questions for me was, what's the best day I've had on my journey at Bitwarden?

Jon McLachlan

Yes, I'm just on the tip of my tongue. So what is your best day?

Michael Crandell

You know, it's a little corny, but I would say every day. Every day is. But seriously, it's probably the first day that I saw a customer support email that came in thanking Bitwarden for building such a great product and cheering us on. And I'm not kidding. As you know, most customer support communications are about problems and complaints, but we get a ton that are just about Bitwarden love, and we get them just about every day, which is why I say every day. And they come from the fact that we have a full-featured free version that's free forever. That kind of goes with the ethos of being open source. And so people appreciate that. And many people actually write in and sign up for the paid version, because they want a way to support what we're doing, which is helping people stay safe online. And it's a core belief of ours that everybody has the right to be safe online. Everybody should have that right. And that's why we do provide a basic full-featured version for free that anybody can use.

Jon McLachlan

That's very generous of you guys. So there's back-end components that are required to run, if you're going to run Bitwarden like entirely yourself. I'm sure you could, because everything's open source, right? But having a SaaS already set up and ready to go is quite convenient. And the fact that you provide that for free is in line with the community [participation is power], right?

Michael Crandell

Yeah, it's part of our core, you know, the significance of what we're trying to do to make a difference in the world, to make the world a better place. We imagine a world where nobody gets hacked. Very aspirational, but it's a great thing that people can believe in, both in our community, but also everybody on the team who works at Bitwarden. It's something you can get up in the morning and believe in. And, you know, just a word, I think some people go, oh, they go, oh, if it's free, it must be, somewhere there's a catch, right? Either the users are the product and we're somehow using advertising to them or using their information. We don't do that, absolutely, at all. We don't track users, we don't capture any information. The way it works is pretty simple. Free users love the product, and they talk about it, if they want to. If they love the product, they're welcome to tell others about it. And so many of them bring Bitwarden to work. And when they do, that's where we make money as a successful company. It's mostly with our business versions. We have an enterprise, a full enterprise version for very large companies, and a Teams version that serves smaller businesses. And that's how it works. And so no pressure on anyone, and the free users don't need to be worried about being misused in any way.

Jon McLachlan

No, that's amazing. And I'm sorry that we live in a world where we have to say things like that, even though it's a SaaS and we provide this great service for free, it's not used for marketing. And so you guys pivoted. Did you help the business pivot from a B2C, primarily a B2C play, into a combined B2C and B2B play?

Michael Crandell

I helped the emphasis there. Kyle had already created the Teams and Enterprise versions, but I do have experience in selling into enterprises and what they need and want. And so when I joined, one of the first things we did is really beef up our security and compliance profile. We went out and got a SOC 2, SOC 3 audit and went through, you know, the rigor of disciplining ourselves to those practices so that customers could trust us. We complemented that with a HIPAA audit. We started increasing the cadence of penetration tests and source code audits. We became GDPR and CCPA compliant from a privacy point of view. So we put a bunch of things together. We created an SLA for larger customers. That's something they expect. This is not a brand new playbook, but it's one that I had been through. So I helped us go through that process. And now at bitwarden.com/compliance, you can see all the wonderful certifications and compliance and security measures we take, just to help increase the validation of the trust that people have in us.

Jon McLachlan

No, that sounds like quite the journey. And under your leadership and guidance, it sounds quite successful. I've been in many B2B plays myself, and I know security is a big role. And you just rattled off all of the major players, all of the important, I don't want to call them checkboxes, but they're real and serious contributions towards the security of a product, through the certifications.

Michael Crandell

So one of the things I learned along the way, one of the things I learned is that for larger companies that are making acquisitions, they have different teams that analyze things. And there's usually a security team as well as the business folks, the procurement folks, the IT team. And with security teams, you either kind of lean in and get a sense of trust early on, or you don't. And if you lean in, then the path tends to be smoother, and you can create that trust early on. Or else you're just fighting a losing battle, because you haven't done the things that they are used to requiring as policies in their companies. And it's understandable, right? They all have policies they need to follow.

Jon McLachlan

Yeah, exactly. They have a tough job as well. And they're in the same community as we all are in the security space. And so it's easy to empathize with the asks that they have. And they're just trying to protect their business as well. Makes perfect sense. So tell me, has there been a worst day for you yet in Bitwarden?

Michael Crandell

Yes, there, there is a kind of a worse day. There's a template.

Jon McLachlan

Oh, there's a whole template for a worst day.

Michael Crandell

It's the same day over and over. We get contacted sometimes by government agencies, whether in the U.S. or overseas, to notify us of data breaches that have occurred, that are being exposed on the dark web, et cetera. And in addition, you know, you can hardly pick up the news anymore without reading about the latest data breach of this or that company, or ransomware. And what's rotten for me is when I read about or hear about these things that hit companies and people because of insecure password practices that could have been so easily avoided. So it's just more pressure. I wish we could all get the word out faster, because it is such a simple thing to roll out password management if you're in a company, or to sign up and use it yourself. And the protection is so much greater through that. That's really my worst day, is when I keep seeing this bad pattern repeat over and over.

Jon McLachlan

Yeah, I have exactly the same sentiment, especially, you know, you're talking about password, password-related breaches. We have the technology to solve basically all of the types of breaches out there. It just takes a certain amount of effort to go in and pull the trigger and commit to raising that security bar, right?

Michael Crandell

Exactly.

Jon McLachlan

And Bitwarden, it sounds like there is plenty of space available. It doesn't even cost anything, and it's available to both consumers and to businesses. I could imagine that's quite frustrating.

Michael Crandell

It is. It's frustrating to hear, but it's motivation to keep getting up every day and getting more and more people onto the platform.

Jon McLachlan

So share with me, there are a couple of different players out there in terms of password managers. Can you share with our listeners what makes Bitwarden special?

Michael Crandell

Absolutely. Number one, we're open source. And that makes a difference because the security of the product is vetted by lots of developers and security professionals around the world. Everybody can look at every line of code, how we do things, et cetera, and validate it. We also offer versions for the largest enterprises, with features typically around integration, integration with single sign-on systems or SSO systems, directory services. We offer self-hosting, the other leaders don't, for those companies that want to do that. And we have those versions for big companies all the way down to individual users. So that span is a differentiator for us. As I've mentioned, in keeping with the open source ethos, we believe strongly that the security of a password manager should be available to everybody worldwide. So we do have that full-featured free version, free forever, no strings attached. And it's helped us create what I think is the most vibrant community around a password manager across the globe. We have over 5 million users of the product who help spread the word, and the product has been translated into almost 50 languages. So it's a very global base, and that's another distinguishing feature of Bitwarden.

Jon McLachlan

Wow, that's incredible. Over 50 languages.

Michael Crandell

Yes.

Jon McLachlan

Was that a community effort?

Michael Crandell

It's largely driven by the community, yes.

Jon McLachlan

It makes me wonder why anyone would use anything else.

Michael Crandell

We wonder that sometimes too, Jon.

Jon McLachlan

Okay, so you mentioned a couple of times Bitwarden is open source, and you share that it means that anyone can audit it, that anyone can go in and look at the code. And because of your B2B efforts, those are being rolled into the open source version as well, I'm assuming, yes?

Michael Crandell

Yes.

Jon McLachlan

So really, anyone can take advantage of the world-class security that's being poured into the B2B product that's being sold to large institutions, large corporations.

Michael Crandell

Correct.

Jon McLachlan

And so what is it about being open source? Why does that matter? Like, is it, couldn't it be hurtful for your business? You know, just to ask the naive question, couldn't someone come along and copy the entire Bitwarden business with your open source product?

Michael Crandell

So in a way, they could. Remember that open source licenses require that whoever copies it open sources what they do also. And you know, that hasn't happened a lot, but when that happens, we try to remember that imitation is the sincerest form of flattery. But nobody's done that in any way that infringes on our business, really. How it works for us is, as I mentioned, it's more transparent. So anybody can look at how we're handling their sensitive data. Let's face it, it's about as sensitive as you can get. All your login credentials, how we do encryption, what's the level of encryption, where and how we use it. They can validate that all their data is end-to-end encrypted, so Bitwarden cannot touch it. And all of that's open to the world. We do get researchers looking at it, et cetera. And of course, it's open not just for reviewing, but for people to contribute, or build upon, or add modules. And finally, one of the advantages is that larger companies these days have come to prioritize using open source products whenever they can. It's actually been in movement, as I'm sure you know, for quite a while. And the reason is it reduces their risk, and it reduces their cost. You know, if they're worried about what happens if the provider of this product goes away, well, they have access to the source code. And open source, of course, tends to be more efficient, more economical from a cost point of view. As to what the danger is to our business, the reality is that very few people build Bitwarden from scratch in order to use it. That's a difference with Bitwarden, which is really an app and a set of clients, from traditional open source, which is more around infrastructure. So in the days of MySQL, people would download it, build it, and run it as a database, essentially a developer product. But as an end-user app with admin features for larger companies, and eight or 10 different clients for Bitwarden. So you're running, some people run it on iPhones, iOS, on Android phones, on Windows, on Mac, on Linux, on five or six different browsers, command line interface. When you add up all those clients, it's just not worth it against our license cost and support to go out and try and build all that and run it. And finally, if you think about it, anybody who would propose that, if you're inside a company and you say, hey, we could save a few bucks if I kind of build Bitwarden myself, I think the IT managers and directors would say, you know, just the internal management. Let's not do that. Let's just license it and [find out there].

Jon McLachlan

Right. Let the folks who wrote this software originally run the software. They know it best. They know how to configure it. It's more efficient if it's multi-tenant, and you can pass on the savings and expertise to all the customers, right?

Michael Crandell

Yes. So it's the best of [both] worlds. We get the benefit of open source, but we don't really have to compete against ourselves.

Jon McLachlan

So a quick question for you. You mentioned that everything is end-to-end encrypted. And so Bitwarden itself, as a product or even as a company, does not have any access to any of that encrypted data, which I think is beautiful and wonderful. That's exactly how it should work. But you also mentioned, and maybe some of our listeners caught it as well, that you have a version of Bitwarden that's available for on-prem deployment, if I understood correctly.

Michael Crandell

Correct. That's right.

Jon McLachlan

Don't those two product features bring you into the same level of security, or a very similar level of security? And I'm curious, who would drive a business to run that whole stack on-prem versus just take advantage of your fully end-to-end encrypted, already managed for you SaaS?

Michael Crandell

Right. The answer to that is really that, if we start with what does the end-to-end encryption buy you as a user or customer, with any product out there, it buys you the fact that nobody in between, during transmission or storage, or the company providing the product, in this case Bitwarden, can ever see your sensitive data. We just do not have access to it, because it's encrypted. So that's classically what's become popular in the last half dozen years, a zero-knowledge approach to security, which is, of course, a really strong one. Despite that fact, there are companies that have an orientation toward wanting to self-host something. Sometimes that can also be in relation to regulatory reasons versus security reasons. What do I mean by that? Maybe you're a company in Switzerland, and the law says that you need to locate all the data for your company within the Swiss borders. So [geolocation] or data residency. In that case, great. Run the server there, and you meet that criterion. And we found that it's productive not to get into arguments with customers about which way they want to do it, but just to provide both and let customers...

Jon McLachlan

No, that makes perfect sense. That's amazing. It's a pattern or a theme that I'm seeing crop up over and over again. It's the data governance and the data residency. And it's not the first time I've heard of this problem. So it'll be interesting to see if we can wrap all of our storage around some abstraction layer that lets us continue down that path of multi-tenancy and hit all of the important requirements that are bubbling up out of geolocation and their data.

Michael Crandell

It's going to be an interesting journey, Jon. It's not going away anytime soon. We see more and more, for example, recently from the EU around privacy requirements. So it's not getting any easier.

Jon McLachlan

How about Bitwarden as a company? How's your culture like? If I were to join there as a new employee, what would that feel?

Michael Crandell

Sure, we'd love to have you, by the way. [Let's start off.] We are a fully remote company. So we have people in somewhere around 22 states in the U.S., I think around 20 or more countries in the world, six continents. We're in Europe, Africa, Middle East, South America, North America, Australia, Asia Pacific, et cetera. So what that means is we're really able to hire the best people, because we can choose from almost anywhere in the world. That's been a real eye-opener for me. The first time I've been in a fully remote company, one of the reasons I joined. That's allowed us to lean into also into diversity on our team, which is the real strength. Our customer base is global, so it's important that our team members be global also. You know, our company values, every company has values. Ours are four: gratitude, responsibility, inclusion, and transparency. And I think, look, all of these are pretty self-evident to people. They certainly seem to appeal to the candidates we end up attracting. But together, they spell the word grit, which I think is really necessary. Yeah, it's really important for building a long-lasting company that continues to innovate over time, because not all of that journey is easy. You need to have stick-to-itiveness.

Jon McLachlan

Yeah, you need to have grit. You need to be prepared to face grit.

Michael Crandell

Yes.

Jon McLachlan

Yeah, I like that word. That's a good word. It brings with it a very entrepreneurial mindset and spirit, along with those four values. Speaking of hiring folks, do you have a favorite interview question?

Michael Crandell

I do. And that is, when I'm interviewing somebody, and by the way, I still interview everybody who joins Bitwarden. I just think it's super important. I learned long ago, even in technology companies, where sometimes outsiders think, oh, it's all about the technical wizardry of this or that product, at the end of the day, it's all about people in technology companies. People are what build the technology, right?

Jon McLachlan

Yes.

Michael Crandell

So I still interview everyone. My question is, what did you like to do when you were 16 years old?

Jon McLachlan

That's a great question. So you can, it's almost like that first question I asked, and I asked you...

Michael Crandell

About childhood. Yep. You tend to get authentic answers, because it's not a question that anyone rehearses for in a job interview. So it's new. It's not all that tough. Hopefully most people remember when they were 16. They think about it for a minute, and it just helps share something about them as a person.

Jon McLachlan

That's really amazing. I love that. It really has nothing to do with the technical pieces. And it's an opportunity for a candidate, perhaps, to share a passion that was there when they were 16. It's still there when, you know, wherever their life has taken them. So in the news, if you look at the news, there's a lot of chatter about going passwordless and this, that, and the other thing, like replacing passwords. What do you make of all of that? And how do you see that dialogue kind of fitting into Bitwarden as a company, and your position in the market?

Michael Crandell

First, passwords are not going away. They're embedded in so much of what we do on computers that it's going to take a long time for all those systems to evolve and change. At the same time, passwordless technologies are already here, and they're super useful. Things like biometrics that we use, Touch ID, Face ID, Android biometrics, et cetera, security keys. So there are a variety of passwordless technologies already in use, and have been for a while. And Bitwarden already supports all the common passwordless technologies, and we'll continue to do that as passwordless evolves, which of course it will. So we look at it really as an and, not an or. People will use passwords and passwordless approaches to authentication, and they'll want tools that let them use the best method in each situation. So that's what we're shooting for. There's a saying that our founder Kyle uses, which is, there is a reason that the word pass or password is not in the company name Bitwarden. It's because we're really focused on a larger goal, which is helping people authenticate safely online, whether through a password or through a passwordless technology.

Jon McLachlan

So you're adapting and changing with the environment, and actually incorporating those new technologies into your ecosystem.

Michael Crandell

Yes. I mean, one of my favorite features, I happen to be an iPhone user, and as you know, there's a password autofill feature kind of built into the iPhone, or capability that different password managers can plug into. So when I'm going to a site and it asks for a password, I click the password button, it brings up Bitwarden, and I authenticate into Bitwarden with Face ID, and that automatically fills the password. So even though it's a password-based site, the experience is pretty much passwordless, because all I'm doing is opening the phone up to my face, and I end up logging into any password-based site. So that's an example of how we've already incorporated passwordless technology into the flow.

Jon McLachlan

No, that's spectacular. And this is how all of these different technology stacks can work together to bring a better user experience, because at the end of the day, it is all about people. And I think when security is done right, it is seamless, and it does not interrupt the flow of your day, but at the same time, it is also very strong. And I know that the Face ID that you just mentioned, behind the scenes, underneath the hood, if you were to peek into iOS, it's using secure enclaves and protected memory and all of those great features that we don't even need to think about as users when we use that.

Michael Crandell

Sure. And of course, at the bottom of it all is a secret. You could think of it as something like a password that gets transferred in order to authenticate you. So even they're passwordless from a user point of view, but under the covers, there's still a certificate or a secret that does get passed. And I think it's important to recognize that end users, most people are not opinionated about technology. They just want to get their work done in the quickest, easiest, best way. So it depends whatever you need to do. If you're on a password-based site, make that easy. If it's passwordless, make that easy. Next question.

Jon McLachlan

Next question, yeah. No, I couldn't agree more. One of the things that still drives me crazy is when there are all of those restrictions on what sort of, what a password should look like. And they only go up to like 32 characters, and you kind of have to figure it out, and you have to play games with like the password length and the types of characters in the password, and hit reset a couple of times until you get one that has all of the right types of characters, and your new random password for your password manager. That stuff is super frustrating.

Michael Crandell

There's a comic who did a whole comedy routine on the evolution of that. He's [...].

Jon McLachlan

I think I've seen this.

Michael Crandell

Yeah, you've seen this, I think so. In the beginning was the password, and we all had our password, and we used it everywhere. And then some sites said, stop, that's not secure enough, I need a capital letter. So we all, as a group, we all jointly decided to capitalize the first letter in our password. Of course, everybody's laughing, because he was so right on. It's what everybody did.

Jon McLachlan

And then he does the special character and the number and all the other requirements.

Michael Crandell

Yes.

Jon McLachlan

It's funny because it's true.

Michael Crandell

Yes.

Jon McLachlan

It wasn't George Carlin, but it's just like George Carlin. It's funny because it's true. We'll have to put a link to that in the notes. All right. So when we look into the future, you look into the future, I'll let you decide how far you want to look into the future. But when we look into that future, and you see Bitwarden as an amazing, smashing success, what does that look like? What does the success look like?

Michael Crandell

Starting from today, in the last couple of years, we've been growing really fast in the password management space. So we're not going to let up the pace of innovation there. That's a major focus and emphasis for us, and a lot more growth in our future. But we'll also expand, Jon, by offering more tools and products for developers, first off, and then also more capabilities that incorporate passwordless authentication approaches. So both of those are going to be emphasis points. And then there are also other adjacencies. For example, we have a feature in Bitwarden called Bitwarden Send, and it allows you to send a piece of text or a file, also end-to-end encrypted, to anyone, whether they're a Bitwarden user or not, with that same zero knowledge trust and sense of security that we have in the rest of the product. And also, one of the nice features about that is you can set a specific expiration date for that message. Companies in particular like that, because they don't want to be building up data that gets exposed during a deposition or some other legal proceeding. They want to know that things are temporary.

Jon McLachlan

Yeah.

Michael Crandell

And you want to know that it's not living around in your [sent] folder or somebody else's inbox forever. So I think of it as, I go back to the Mission Impossible TV series, where they had that tape recording that self-destructed after 15 seconds. So this is similar to that. Your message can be transmitted, and then it goes away. And we get a lot of requests around enhancing that functionality for larger companies. So that's another area. All of it's going to come under the umbrella of helping people stay safe online and doing business faster, safely. And it all starts with simple, secure, and convenient authentication.

Jon McLachlan

No, that sounds amazing. I would use that feature all of the time. You know, when someone comes over and they're like, hey, what's the Wi-Fi password? And do they have Bitwarden? I don't know. Maybe. Oh, you can send them the secret. You can send them the password. You can send it, share it just for the day, you know, doesn't need to be forever. So when they get a new phone or they lose their phone, your password's not just dangling in someone else's device that's now in the hands of who knows who, right?

Michael Crandell

Well, check it out.

Jon McLachlan

I will definitely be checking it out. Michael, this has been amazing. Thank you so much for joining me. Would you like to leave our listeners with any parting words of wisdom?

Michael Crandell

Absolutely. Please come have a look at Bitwarden. It's free. Don't be one of those folks who gets caught with your pants down because of a password mishap. Once you get into it, you're going to have an aha moment of where security and ease of use come together, and you'll never go back.

Jon McLachlan

I'm going to go check it out myself right now. Well, I want to thank Michael again. Thank you. And thank all of our listeners for joining for this episode. Stay tuned for the next episode of the Security Podcast in Silicon Valley.

Michael Crandell

Thank you, Jon. It's great to be on the show.

FAQ

Questions this episode answers

What makes a password secure?
On this episode, Michael Crandell said a secure password is unique, so a breach of one doesn't compromise other accounts, and complex, so it can't be guessed or cracked by a computer. Michael put the sweet spot at about 14 characters.
How does Bitwarden make money if the free version is free forever?
Michael Crandell said free users love the product, tell others and bring Bitwarden to work. Bitwarden makes its money mostly from its business versions: Enterprise for the largest companies and Teams for smaller ones. It doesn't track users or capture their information.
What did Bitwarden do to sell to enterprises?
A SOC 2 and SOC 3 audit, a HIPAA audit, more frequent penetration tests and source code audits, GDPR and CCPA compliance, an SLA for larger customers, and a compliance page at bitwarden.com/compliance.
Couldn't someone copy Bitwarden's open source code and compete?
Michael Crandell said open source licenses require copiers to open source their work too, and that few people build Bitwarden from scratch. It's an app with eight or 10 clients, and building and running them isn't worth it against the license cost and support.
Why self-host Bitwarden if it's end-to-end encrypted?
End-to-end encryption means nobody in between, and not Bitwarden, can see the data. Some companies self-host for regulatory reasons, such as a Swiss company that must keep data inside Swiss borders. Bitwarden offers both.
What do Bitwarden's values spell?
On this episode, Michael Crandell listed four values: gratitude, responsibility, inclusion and transparency. Together they spell grit.
Are passwords going away?
Michael Crandell said no. Passwords are embedded in so much of computing that change will take a long time, while passwordless technologies such as biometrics and security keys are already here. Bitwarden treats them as working together.
What happened at Bitwarden after the episode?
Bitwarden announced a $100 million growth investment led by PSG in September 2022, bought Passwordless.dev in January 2023, and launched Bitwarden Authenticator in May 2024. Michael Crandell stepped down as CEO in February 2026, and in July 2026 Bitwarden said it had passed 15 million users and 80,000 businesses.
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