Podcast Episode 8

Episode 008 46 min

Fredrick Lee, CSO of Gusto: Why is authentic diversity essential for epic security teams?

with Fredrick Lee · Gusto

0:00 / 46:00

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Episode 8 of The Security Podcast of Silicon Valley, published August 24, 2021. Host Jon McLachlan talks with Fredrick Lee, known as Flee, then the chief security officer at Gusto, after roles at Square, NetSuite, Twilio, Betfair, Fortify Software and Bank of America. Flee traces a path from computer magazines and 2600 to a security community built on sharing, compares security to free form jazz, and describes the CISO as the one who puts the band together. The talk covers risk as the place where opportunity is, two days at Gusto worth being proud of, data custodians, why diversity is technically correct for threat models, hiring for aptitude over certifications, security savior syndrome, and a security team that scales past its headcount. About 46 minutes.

Episode notes

In this deeply insightful episode of a YSecurity.io production, we are honored to have Fredrick Lee ("Flee"), the Chief Security Officer at Gusto, share his experiences and the profound impact of diversity on building engineering and security teams. Flee's journey from his childhood, through his formative years at a boarding school in the deep south, to his role as a leading figure in cybersecurity, is not only inspiring but also illuminates the critical role diversity plays in fostering innovation and resilience.

Flee recounts his early fascination with computers and his discovery of the hacker magazine 2600, which opened a new world of security challenges and opportunities. Inspired by pioneers like John Lee (John Threat), Flee's narrative is a testament to the power of representation and the importance of diverse role models in the tech space. His journey is a reflection of how a community of diverse outcasts, connected by their passion for computing, can shape one's path in cybersecurity.

The conversation then shifts to the core of diversity's value in engineering and security teams. Flee articulates why building diverse teams is not just a social imperative but a technical necessity. He explains how diversity brings a multitude of perspectives that enhance problem-solving and innovation, leading to more resilient teams and products. Flee argues that the varied experiences and backgrounds of a diverse team contribute to a richer understanding of security challenges and more creative solutions.

Collaboration and open-source are highlighted as vital components of the security community, promoting a culture of sharing and collective growth. Flee shares how these practices have been instrumental in his work and the broader cybersecurity landscape, enhancing the community's ability to respond to threats and vulnerabilities effectively.

One of the most poignant moments of the interview comes when Flee describes his best days as the CSO at Gusto, particularly in the wake of George Floyd's murder. He reflects on the significance of empathy, leadership, and the responsibility of organizations to not only acknowledge societal issues but to actively contribute to positive change.

Join us for an unforgettable conversation with Fredrick Lee on the indispensable role of diversity in building effective, resilient, and innovative security teams. Whether you're in the cybersecurity field, passionate about diversity and inclusion, or interested in the intersection of social justice and technology, this episode offers invaluable insights into the power of diversity as both a moral and technical imperative for the future of tech.

Hosted by Jon McLachlan — co-founder of YSecurity.

The deep dive

Lived experience is a threat model

Fredrick Lee, known as Flee, then the chief security officer at Gusto: magazines, BASIC and 2600, learning by sharing on IRC and Usenet, security as free form jazz, a CISO who puts the band together, risk as the place where opportunity is, two days at Gusto worth being proud of, data custodians, small progress and angry optimists, bringing your full self to work, lived experience in threat models, hiring for aptitude over certifications, security savior syndrome, and a security team that scales past its headcount.

Episode 8 of The Security Podcast of Silicon Valley came out on August 24, 2021, with Jon McLachlan hosting. The guest was Fredrick Lee, known as Flee, then the chief security officer at Gusto, which makes payroll, benefits and HR software for U.S. businesses (Podbean, LinkedIn, Gusto).

Flee’s case is that a security team does its job better when its people differ from each other and bring all of themselves to work. Each person’s lived experience feeds a threat model, so a team that looks alike can miss a threat that someone else would see at once.

This page follows the conversation in order: a section for each part of it, eleven figures, thirteen clips from the tape, Flee’s op-ed on data custody, the full transcript, and five tools: a quiz, a scorecard for security savior syndrome, a calculator for how far each security person stretches as a company grows, 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 developer to security chief

Jon’s introduction ran through Flee’s career, newest first: chief security officer at Gusto, head of information security at Square, director of security at NetSuite (part of Oracle), lead security engineer at Twilio, security manager at Betfair, security researcher at Fortify Software, a VP at Bank of America, and a Java developer at Transcore. Flee said the list traces a career through the dot-com crashes.

LinkedIn dates the Gusto role from March 2019 to July 2023, and the Square role from December 2016 to February 2019. It lists the first role as senior systems developer at Intelis, starting October 1999 (LinkedIn). Bank Innovation reported in March 2019 that Gusto had hired Flee as chief security officer, reporting to co-founder and CTO Edward Kim, with growing the security team as a first task (Bank Innovation).

Jon remembered running into Flee at BSides and at RSA, and coming away each time with a warm feeling about the way Flee spoke about security and team building.

Eight cards. 1999 to 2002: developer roles at Intelis and Transcore. 2002 to 2007: Bank of America, VP. 2007 to 2010: Fortify Software, software security researcher. 2010 to 2012: Betfair, U.S. information security manager. 2012 to 2014: Twilio, lead security engineer. 2014 to 2016: NetSuite, director of security. 2016 to 2019: Square, where Flee led information security. Filled, at the episode: Gusto, chief security officer, from March 2019.
Flee's path before the episode. Sources: the episode and LinkedIn.

Magazines, BASIC and 2600

Jon asked how Flee became interested in security. Flee learned from computer magazines: articles on what people did with computers, with sample programs in BASIC to type into a Tandy or a Commodore 64. Then came a magazine called 2600.

Wikipedia describes 2600: The Hacker Quarterly as a seasonal publication of technical articles, many of them written and submitted by its readers, on hacking, telephone switching systems and Internet protocols. It launched in January 1984, and its name comes from a 2600 hertz tone (Wikipedia).

Much of what people worked on came down to puzzles. Flee has a phrase for that approach to learning.

“aggressive exploration and aggressive education.”

Fredrick Lee, at 5:42

Jon liked how positive it sounds.

Learning by sharing

Flee credited the security community of those early days, and pointed to how powerful IRC and Usenet were.

“it was all about sharing.”

Fredrick Lee, at 8:41

People asked each other what they had learned, how an operating system or a university’s computers worked, why someone built a thing a certain way, how to obfuscate code or crack software. The community isn’t perfect and it’s far from friendly, Flee said, which is something it works on. One lesson stayed with Flee.

“we’re better when we collaborate”

Fredrick Lee, at 9:08

Jon called it a truth most people miss.

“sharing our experiences is how teams become stronger than some of their individual parts”

Jon McLachlan, at 9:21

Wikipedia describes IRC as a text-based chat system built for group discussion in channels, created in August 1988 (Wikipedia), and Usenet as a worldwide distributed discussion system, set up in 1980, where people post articles to newsgroups (Wikipedia).

Listen · Fredrick Lee on episode 8, from 8:39
About 35 seconds: Flee on the sharing that taught the field. The clip stops on its own. Read the full transcript.
Three boxes joined by arrows: magazines with programs in BASIC, 2600, a hacker quarterly, and, filled, IRC and Usenet, people who share. Below, three questions people asked each other: what have you learned? How does this operating system work? Why did you build it that way? Quote: "we're better when we collaborate"
From magazines to a community that shares. Sources: the episode and Wikipedia.

Security as free form jazz

Flee still sees that spirit in Silicon Valley, above all in open source. Being a hacker, or a curious computer user, goes hand in hand with it.

“we’re just here for the purity of the puzzle.”

Fredrick Lee, at 9:45

Progress comes from taking someone else’s knowledge and doing a slight riff on top of it. Someone lays down a melody, someone else riffs on it, it turns into something new, and the next person riffs on that.

“it feels a lot like almost like free form jazz.”

Fredrick Lee, at 10:02

Flee is passionate about music, and puts security, jazz and hip hop together: do it yourself, explore past the boundaries people said existed, and reuse what’s already there. Jon heard an art underneath all of it. When a team finds its groove, it can build something cool fast and surprise everyone in the room. Wikipedia describes free jazz, also called free form jazz, as an experimental approach to improvisation from the late 1950s and early 1960s, when musicians broke down conventions such as regular tempos and chord changes (Wikipedia).

Listen · Fredrick Lee on episode 8, from 9:57
About 20 seconds: Flee on security as a riff on what came before. The clip stops on its own. Read the full transcript.

The CISO puts the band together

Jon asked what a day in the life of a CSO looks like. Flee sees a lot of misconceptions about the role, what the job is day to day, and what makes someone qualified for it. In a new generation of CISOs, many didn’t take the job on purpose. Flee joked that the company needed one, the person was there, and wasn’t smart enough to say no.

Most people in security are deeply technical and want to stay that way. The CISO’s job is different.

“getting these various band members together and making their individual performances into a song”

Fredrick Lee, at 12:07

The goal is a strong team that keeps a security culture going. Culture matters because no team can stop every bad thing. Something new is always waiting to be found, by some kid tinkering on the internet, and Flee called the idea that CISOs can prevent all bad outcomes false.

What a CISO can do is build a culture of security and resiliency: common practices and operating rhythms that make what the company ships more secure today than it was two days ago, with more and more people across the company doing the work of security.

“They win by getting the entire company to embrace security”

Fredrick Lee, at 13:37

Flee called communication fundamental: explaining risk to the whole organization, in a way that’s right-sized for the business.

Listen · Fredrick Lee on episode 8, from 12:00
About 15 seconds: Flee on the CISO as the one who puts the band together. The clip stops on its own. Read the full transcript.
Listen · Fredrick Lee on episode 8, from 12:56
About 35 seconds: Flee on culture over prevention. The clip stops on its own. Read the full transcript.
Three cards. Prevention alone: something new is always waiting to be found, so no team stops every bad outcome. Filled, a culture: common practices and operating rhythms, with more people across the company doing security work. Communication: risk explained to the whole organization, at the right size for the business. Quote: "They win by getting the entire company to embrace security"
What a CISO builds, in Flee's words. Source: the episode.

Where the opportunity is

Flee doesn’t think security should eliminate risk.

“Risk is where opportunity is, right?”

Fredrick Lee, at 14:20

An investor in the stock market takes a bet for the chance of an oversized outcome. The internet as we know it exists because people took risks. Flee went back to the late 1990s, when people bought Beanie Babies on eBay. Putting a credit card number on the internet, trusting that a stranger would get paid and nobody would steal the rest of your money, sounded crazy. Jon agreed it was insane at the time. Math and cryptography made it safer: SSL, known now as TLS. A booming industry followed.

Square looked like the same kind of idea: hand your card to a stranger who taps numbers into a phone. Payroll worked the same way: take sensitive personal data and make it useful, to pay people and give them benefits. Each bet built a large company. Part of the CISO’s job, Flee said, is to help the company take risks. That means explaining what risk the company has, and finding ways to take it safely. Flee called it pragmatic risk taking, an idea learned through Sam Quigley, and said security should enable the business.

“we’re there to actually be business enablers and not people actually say no.”

Fredrick Lee, at 16:36

The other half of the job is resiliency, in case a risk doesn’t pay off.

“I’m more interested in being able to fail quickly and recover quickly and safely”

Fredrick Lee, at 17:01

That beats a promise to eliminate every vulnerability, Flee said, because it keeps the business moving at speed while it protects customers. Wikipedia says Beanie Babies were the most bought and sold items on eBay, about 10% of all listings in 1997 (Wikipedia), and describes TLS as a cryptographic protocol for secure communication over a network (Wikipedia).

Listen · Fredrick Lee on episode 8, from 14:11
About 25 seconds: Flee on why security shouldn't eliminate risk. The clip stops on its own. Read the full transcript.
Listen · Fredrick Lee on episode 8, from 15:25
About 25 seconds: Flee on the bets behind Square and eBay. The clip stops on its own. Read the full transcript.
Three cards. eBay, late 1990s: a card number on the internet, paid to a stranger, with SSL, now TLS, making it safer. Square: hand your card to a stranger who taps numbers into a phone. Payroll: sensitive personal data, used to pay people and give them benefits. Below, three boxes joined by arrows for the CISO's part: explain the risk you have, take it safely, and, filled, recover quickly and safely. Quote: "Risk is where opportunity is, right?"
Three bets that sounded crazy, and the CISO's part in them. Sources: the episode and Wikipedia.

Two days to be proud of

Jon asked for a single best day at Gusto. Flee asked to talk about more than one.

The first came in the summer of 2020, during the protests that followed the murder of George Floyd. Wikipedia dates the murder to May 25, 2020, in Minneapolis (Wikipedia). Gusto stopped.

“we’re going to just stop what we’re doing right now.”

Fredrick Lee, at 18:38

The company held an all-hands for everyone: what was happening in the community, how employees felt about it, and what Gusto could do to show up and offer more support. Follow-on actions came after that day.

“We’re here to build a better society and a better future.”

Fredrick Lee, at 19:25

It was the first company Flee had worked at that was willing to do that. Other companies had talked about diversity, and Jon named the gap that talk leaves.

“It’s nice to hear it, but then it’s like, then what happens?”

Jon McLachlan, at 19:50

Listen · Fredrick Lee on episode 8, from 18:34
About 15 seconds: Flee on the day Gusto stopped to talk. The clip stops on its own. Read the full transcript.

The second best day started with an internal issue in how engineering worked. It wasn’t a security defect or a compromise, and Flee kept the details private. Flee explained the problem, the engineers took it on, and they fixed something they had thought couldn’t be solved.

“all the engineers got on board.”

Fredrick Lee, at 20:30

They were probably quicker about it than Flee was, because they had taken in why it mattered to the people who use Gusto. To Flee, that proved the culture was working.

Two cards. Filled, summer 2020: after the murder of George Floyd on May 25, 2020, Gusto stopped work for an all-hands about what was happening, how people felt, and what the company could do. An engineering fix: engineers took on a problem they had believed was unsolvable, and fixed it, probably faster than Flee. Quote: "we're going to just stop what we're doing right now."
Two days at Gusto worth being proud of. Sources: the episode and Wikipedia.

Custodians of the data

What the engineers took in is a view Flee talks about inside Gusto.

“We don’t own any data at Gusto.”

Fredrick Lee, at 21:34

The company owns little data, Flee said. It is a data custodian.

“that data really is just a proxy for a human.”

Fredrick Lee, at 21:41

The zeros and ones stand for real people who depend on Gusto to do a good job with them.

“being good custodians and good shepherds of that data”

Fredrick Lee, at 21:58

Flee wants nobody to have a negative surprise from Gusto, and wants the company proud and transparent about how it uses data. Jon repeated those words back.

Flee had made the same case in a TechCrunch op-ed on February 7, 2020, “CCPA won’t be enough to fix tech’s data entitlement problem.” It argues for building systems around data custodianship, with the principle of least privilege, and says “No company is entitled to data; they are entrusted with it.” (TechCrunch). Wikipedia describes least privilege as giving each part of a system access only to what its legitimate purpose needs (Wikipedia).

Listen · Fredrick Lee on episode 8, from 21:32
About 30 seconds: Flee on data custodians. The clip stops on its own. Read the full transcript.
Two cards. Data owner: the company treats the data as its own. Filled, data custodian: the company holds data for people, and each record stands for a human. Below: no negative surprises, so be open and proud about how the data gets used. TechCrunch, February 7, 2020: build systems around data custody, with least privilege. Quote: "that data really is just a proxy for a human."
Owner or custodian: two ways to hold data. Sources: the episode, TechCrunch and Wikipedia.

Small progress over time

Change needs a catalyst, Flee said, and the resiliency to keep at it. The first security engineer or the first CISO at a company makes a lot of small progress.

“that small progress over a duration is what fundamentally actually changes the company.”

Fredrick Lee, at 24:03

Security people may look grumpy, Flee said, but they’re some of the biggest optimists in the world, because they know what a better future could look like. Jon took it from there: we picture that future, then build toward it.

“build little roads and struts to help bring us towards there”

Jon McLachlan, at 24:23

Listen · Fredrick Lee on episode 8, from 23:59
About 20 seconds: Flee on small progress and optimism. The clip stops on its own. Read the full transcript.

Bring your full self

Jon talked about bumping into people who are different from us, and bringing our full selves to the table. Those small moments, in Jon’s view, lead to change and to more open minds. Flee called it a passion area, and wants more security people to bring all of themselves to work.

The security community can be toxic, and Flee wrestles with how much of its culture is good. Some of it needs to be erased: sexism, gatekeeping, homophobia, transphobia and racism.

“Bigotry has no place in security.”

Fredrick Lee, at 27:38

In the early days, most people in the field never even saw each other.

“security used to always be a refuge for the nerdy outcasts.”

Fredrick Lee, at 27:49

Flee used to joke that if you got into security, there was probably something wrong with you.

Diversity is technically correct

The field’s problem at the time of the episode, Flee said, was getting more diversity. Diversity matters for more than it being the right thing to do, though it should be done for that reason too, Flee said. Even more so, it’s technically the correct thing to do.

Part of the job in security is thinking about every bad thing that can happen, and how to mitigate it. Each person brings a different view of the world to that.

“we all have these lived experiences that feed into our personal threat models”

Fredrick Lee, at 29:40

Flee’s example was a payment app like Venmo, whose feed can show where people spend money. If everyone around you can see that you went to a gay bar, in a place that’s less accepting, the consequences can be physical and real. A security team without that diversity can miss it.

“you might literally miss that aspect.”

Fredrick Lee, at 30:44

Jon added a second gap: a team can have the diversity while people hold part of themselves back. Flee agreed, and went further.

“making it psychologically safe for somebody to actually be who they are is also important.”

Fredrick Lee, at 30:58

Another of Flee’s examples comes from culture. In a more patriarchal society, a feature that shows who reached out to a young woman, say a random man on LinkedIn, can bring negative consequences for her. People with that background can point out the cultural differences while a product is being built.

Payment apps raise a related question: whether a product makes it easy for an abuser to keep reaching someone, for example through the note on a one-dollar payment. The security industry can improve those cases, Flee said, and that’s much of the reason for this view.

“security teams, in order to be successful, must be diverse.”

Fredrick Lee, at 33:40

Flee wants it to be easier for people who are different to build long careers in security. The test should be whether someone can do the job.

“can you be a good security practitioner? It shouldn’t matter who you date, who you marry”

Fredrick Lee, at 34:02

Wikipedia describes a threat model as a process for identifying and listing potential threats, and prioritizing the countermeasures (Wikipedia), and psychological safety as the belief that you won’t be punished or humiliated for speaking up with ideas, questions, concerns or mistakes (Wikipedia).

Listen · Fredrick Lee on episode 8, from 29:20
About 25 seconds: Flee on why diversity is technically correct. The clip stops on its own. Read the full transcript.
Three boxes joined by arrows: lived experience, what you've seen, feeds a threat model, what could go wrong, and, filled, the product, with fewer missed harms. Below, three examples from the episode. A payment feed shows where someone spent money, at a gay bar for example, in a place that isn't accepting. A contact list shows who reached out to a young woman, in a more patriarchal society. A payment note lets an abuser keep reaching someone, for the price of a dollar. Quote: "security teams, in order to be successful, must be diverse."
Lived experience as an input to a threat model. Sources: the episode and Wikipedia.

Hiring for aptitude

Jon has built teams in the Valley, and has seen what happens when differences and different experiences are set up as a team’s strengths.

“a camaraderie that you would otherwise miss”

Jon McLachlan, at 34:39

That leads to better products and more innovation, in Jon’s experience, and to people who feel part of something bigger. Jon asked what signal Flee looks for when interviewing someone for a senior security role.

With senior leaders, Flee looks at how they think about what a good security hire looks like. Flee has zero certifications.

“I am certifiable, but I’m not certified.”

Fredrick Lee, at 35:42

A good sign is a leader who knows the core attributes and aptitude a person needs to be effective in cybersecurity. A bad sign is a list: these tools, these certifications, this school. Jon compared that to nails on a chalkboard, and Flee could see the rejection on Jon’s face.

What Flee wants to hear is a test of whether someone can walk through something that looks like a threat model, and natural aptitudes such as curiosity and creative thinking.

“really strong at translation and really strong at communication”

Fredrick Lee, at 36:36

A leader who says that lights Flee up.

A leader who welcomes passions outside security is open to all walks of life. A life outside the field shows a full person.

“you’re not just pigeonholed into this one identity”

Fredrick Lee, at 37:08

People often treat problems with diversity as a white male problem, Flee said, and that isn’t true.

“Everybody can have some kind of bias.”

Fredrick Lee, at 37:29

Flee tries to tease out a leader’s biases, and how the leader could broaden their horizons. Bias isn’t limited to one demographic, Flee said, and every group in the Bay Area has some to challenge.

“We are diverse, but we’re not integrated here in the Bay Area.”

Fredrick Lee, at 38:29

Jon agreed that there’s work left.

“The future is not here yet.”

Jon McLachlan, at 38:35

Listen · Fredrick Lee on episode 8, from 36:19
About 20 seconds: Flee on what a good hiring answer sounds like. The clip stops on its own. Read the full transcript.
Two cards. A bad sign: a list of these tools, these certifications, this school. Filled, a good sign: a threat model walkthrough, curiosity, creative thinking, strong translation and communication, and passions outside security. Below: bias isn't limited to one demographic, so Flee tries to tease out each leader's biases. Quote: "I am certifiable, but I'm not certified."
What Flee listens for in a security leader's hiring answer. Source: the episode.

Angry optimists

What Flee loves about security people is that they’re angry optimists. They look at the world and say it could be better. Jon called it a wonderful description.

Security savior syndrome

Jon noted how stressful and visible security gets when things go wrong, and pointed to the recent T-Mobile breach. Jon asked what advice Flee had for people helping their company through a ransomware attack or a data breach. Wikipedia says T-Mobile confirmed the breach on August 16, 2021, and two days later said the stolen records covered more than 40 million former and prospective customers and 7.8 million current postpaid customers (Wikipedia).

Flee had a name for the trap.

“this thing that I call security savior syndrome”

Fredrick Lee, at 39:32

Security people and security teams come to believe they must carry the burden of every bad outcome, and prevent every one of them.

“That will quickly burn you out.”

Fredrick Lee, at 39:47

Flee’s first advice is forgiveness, for yourself.

“we cannot prevent every single bad outcome.”

Fredrick Lee, at 40:00

Everyone in security should at least consider therapy, Flee said, and practice mindfulness. Build relationships inside your company, so you have support.

“You’re not supposed to be in this alone”

Fredrick Lee, at 40:44

Where the company allows it, and Flee said not every company does, shift the culture so the business owns its risk decisions.

“business owners own the risk and the outcome from their decisions as opposed to security.”

Fredrick Lee, at 40:58

Then security isn’t on the hook for fixing someone else’s mistakes, and can come at a problem from a helping angle. Episode 7 made a similar case: the business makes the risk decision, and security explains the risk in terms it can decide on.

Take a vacation at least once a quarter, ideally a week each quarter, to recharge. Flee called security a marathon. The work is many small changes that add up over time, and some bad things will still happen. In a crisis, show calm, which also helps your own stress.

“at least display the demeanor of calmness.”

Fredrick Lee, at 42:12

People look to security almost like mom and dad, so security’s reaction gets amplified. Tell the CEO an incident will destroy the company, and the CEO believes it and gets stressed. The stress circles back to you, spreads to your team and peers, and feeds on itself.

Mind your physical health too, and watch for substance abuse. Flee sees a culture in the field that celebrates drinking, and doesn’t judge anyone for it.

“alcohol is not a solution for stress.”

Fredrick Lee, at 43:29

You don’t need a therapist to talk things through, Flee said.

“You can literally have your security peers be your therapy”

Fredrick Lee, at 44:10

Flee named IRC as an outlet, and Slack and Discord for younger people. Jon singled out the advice on risk ownership.

“it’s a great way to scale a security culture across an organization.”

Jon McLachlan, at 44:32

Responsibility stops sitting in one place and spreads everywhere. Wikipedia notes that the World Health Organization describes occupational burnout as a work-related phenomenon from chronic workplace stress that hasn’t been successfully managed (Wikipedia).

Listen · Fredrick Lee on episode 8, from 39:31
About 30 seconds: Flee on security savior syndrome. The clip stops on its own. Read the full transcript.
A filled card for the syndrome: security comes to believe it must carry every bad outcome and prevent all of them. Below, eight numbered ways out: forgive yourself, since no one prevents every bad outcome. Consider therapy, and practice mindfulness. Build relationships inside the company. Let business owners own the risk of their decisions. Take about a week off every quarter. Stay calm in a crisis, since security's reaction gets amplified. Mind your health, and watch for substance abuse. Talk things through with security peers. Quote: "That will quickly burn you out."
Security savior syndrome, and the ways out of it. Source: the episode.

Scaling past headcount

As a company grows, Jon said, its security team may not grow as fast, so each security person has fewer resources for a larger group of people. Flee agreed, and called it reality, with good reasons behind it.

“Security should be like a highly leveraged discipline.”

Fredrick Lee, at 45:01

Security people can do a lot, but that doesn’t mean they should be superheroes and burn themselves out. A good security team can scale better than a lot of engineering teams. It will never be the size of engineering or marketing, while it’s responsible for helping every department, so the ratio looks small next to the rest.

Flee called that part of the fun of the challenge. The calculator below shows how far each security person stretches as a company grows. Jon closed by thanking Flee for the perspectives on diversity, security and team building.

Listen · Fredrick Lee on episode 8, from 44:53
About 15 seconds: Flee on why the security team never keeps pace. The clip stops on its own. Read the full transcript.
Three boxes joined by arrows: the company grows fast, security grows slower, and, filled, reach, where every team does some security work. Below: with the calculator's defaults, 300 people and 5 in security is 60 people per security person. At 40% growth a year and one security hire a year, that becomes about 84 in two years. A security team never matches engineering or marketing in size, and it helps every department. Quote: "Security should be like a highly leveraged discipline."
Why the security team never keeps pace, and how it reaches further. Source: the episode.

What happened after the tape

Reddit’s security chief. On July 31, 2023, SecurityWeek reported that Reddit had hired Flee as CISO, overseeing information security, privacy and compliance risks and reporting to CTO Chris Slowe (SecurityWeek). Cybersecurity Dive reported the same day that Flee would lead Reddit’s privacy and security teams, after serving as chief security officer and head of IT at Gusto from 2019 (Cybersecurity Dive). LinkedIn lists the Reddit role from July 2023 through October 2026 (LinkedIn).

Gusto kept growing. Wikipedia says Gusto launched as ZenPayroll on December 11, 2012, took its current name in September 2015, and was valued at $9.6 billion in 2023, with $500 million in annual revenue. It agreed to buy Guideline for about $600 million in August 2025, bought Mosey in April 2026, and passed $1 billion in annual revenue by early 2026 (Wikipedia).

Square became Block. On December 10, 2021, Square, Inc. changed its name to Block, Inc. (Wikipedia). Reddit went public in March 2024, raising $600 million (Wikipedia).

A timeline. August 24, 2021: this episode, with Flee as Gusto's chief security officer. December 10, 2021: Square, Inc. changes its name to Block, Inc. July 2023, filled: Flee joins Reddit as CISO, overseeing security, privacy and compliance risks. March 2024: Reddit goes public, raising $600 million. August 2025: Gusto agrees to buy Guideline for about $600 million. Early 2026: Gusto's revenue passes $1 billion a year. October 2026, filled: LinkedIn lists the Reddit role through this month.
Flee, Gusto, Square and Reddit after the episode. Sources: SecurityWeek, Cybersecurity Dive, LinkedIn and Wikipedia.

The same themes on this show. Episode 2 had Andrew Gontarczyk, then the CISO of Pure Storage, on building a security team and hiring for execution and delivery. Episode 17 had Sean Cassidy, then the first head of security at Asana, on hiring software engineers and teaching them security, and a high-trust culture. Episode 46 had Polina Morozov, then a security recruiter at Grammarly, on green flags and red flags in hiring. Episode 5 had Leigh Honeywell of Tall Poppy on online harassment and personal security. Episode 80 had Ted Harrington on the hacker inside everyone and why curiosity matters.

Did you catch it? A seven-question quiz

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

Quiz · seven questions

Did you catch it?

Pick an answer to see whether you caught it.

  1. How did Flee describe the early days of the security community on IRC and Usenet?

    b. "it was all about sharing." Transcript, 8:41.

  2. What kind of music does Flee compare progress in security to?

    a. "it feels a lot like almost like free form jazz." Transcript, 10:02.

  3. What does Flee say about the idea that CISOs can prevent every bad outcome?

    c. Flee called the idea that CISOs can prevent all bad outcomes false. See The CISO puts the band together.

  4. Where does Flee say opportunity is?

    b. "Risk is where opportunity is, right?" Transcript, 14:20.

  5. What does Flee call a company that holds people's data?

    a. "being good custodians and good shepherds of that data" Transcript, 21:58.

  6. Why does Flee say diversity is technically correct for a security team?

    c. "we all have these lived experiences that feed into our personal threat models" Transcript, 29:40.

  7. What does Flee call the belief that security has to carry every bad outcome?

    a. "this thing that I call security savior syndrome" Transcript, 39:32.

Is your security team carrying it all?

Eight questions on security savior syndrome, built from Flee’s advice. Each tip links the section behind it.

Scorecard · eight questions

Is your security team carrying it all?

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

  1. Who owns the risk when a team ships something or changes a process?

    • Security, by default
    • Security, with input from the team
    • The business owner, with security's advice

    Flee's advice is to move the risk and the outcome to business owners. See Security savior syndrome.

  2. What does your security program promise the company?

    • That nothing bad will happen
    • Fewer incidents
    • Fast, safe recovery when something does happen

    Flee called the idea that CISOs can prevent all bad outcomes false. See The CISO puts the band together.

  3. Do people on the security team take real time off?

    • Rarely
    • A week now and then
    • About a week every quarter

    Flee recommends a week each quarter. See Security savior syndrome.

  4. In an incident, how does security talk to leadership?

    • In alarm
    • Calmly, but making it up as we go
    • Calmly, with a plan we've practiced

    "at least display the demeanor of calmness." See Security savior syndrome.

  5. After an incident, what does the review look for?

    • Someone to blame
    • The cause, with some blame
    • The fix and the lesson, with no blame

    "we cannot prevent every single bad outcome." See Security savior syndrome.

  6. Does security have allies across the company it can lean on in a crisis?

    • Few
    • In some teams
    • In most teams

    "You're not supposed to be in this alone" See Security savior syndrome.

  7. Do your security people have peers outside the company to talk things through with?

    • No
    • A few, informally
    • Yes, in regular groups or communities

    "You can literally have your security peers be your therapy" See Security savior syndrome.

  8. How much of the security work do other teams own?

    • Security does it all
    • Some teams share it
    • Most teams own part of it

    "They win by getting the entire company to embrace security" See The CISO puts the band together.

Carrying it all

Start by naming a business owner for each big risk, and book the team's time off.

Sharing some of the load

Practice the incident plan, and drop the blame from the review.

Built to last

Keep the time off, the peers and the shared ownership on a schedule.

Will your security team keep up?

The calculator runs Jon’s point from Scaling past headcount: as a company grows, each security person covers more people.

Calculator

Will your security team keep up?

Four numbers: people at the company today, how fast the company grows each year, people on the security team today, and security hires you plan each year.

60people per security person today
84people per security person in two years
3security hires a year to hold today's ratio

With 300 people and a security team of 5, each security person covers about 60 people. If the company grows 40% a year and security adds 1 a year, that becomes about 84 people per security person in two years. Holding today's ratio would take about 3 security hires a year.

The defaults are placeholders, so put in your own numbers. Growth is compounded once a year. Flee's answer to a rising ratio: other teams own part of the security work, so the security team doesn't have to grow at the company's pace.

From 2600 to Reddit

Flee’s path, the field around it, and this show. Filter by topic.

Timeline

From 2600 to Reddit

  1. 2600 launches

    The hacker quarterly that Flee found as a reader (Wikipedia, on this page).

  2. IRC

    Internet Relay Chat is created, a text chat built for group channels (Wikipedia, on this page).

  3. eBay

    Founded as AuctionWeb. Beanie Babies were 10% of its listings in 1997 (Wikipedia, on this page).

  4. Intelis

    Senior systems developer, until August 2001 (LinkedIn).

  5. Transcore

    J2EE developer, until February 2002 (LinkedIn).

  6. Bank of America

    VP, until February 2007 (LinkedIn).

  7. Fortify Software

    Software security researcher, then principal researcher, until September 2010 (LinkedIn).

  8. Betfair

    U.S. information security manager, until August 2012 (LinkedIn).

  9. Twilio

    Lead security engineer, until March 2014 (LinkedIn).

  10. ZenPayroll launches

    The company renamed itself Gusto in September 2015 (Wikipedia).

  11. NetSuite

    Director of security, until December 2016 (LinkedIn).

  12. Square

    Head of information security, until February 2019 (LinkedIn).

  13. Empowering through security

    O'Reilly publishes an excerpt of Flee's keynote at its security conference in New York (O'Reilly).

  14. Gusto

    Chief security officer, reporting to CTO Edward Kim (Bank Innovation, on this page).

  15. The op-ed on data custody

    Flee's TechCrunch piece on the data entitlement problem (TechCrunch, on this page).

  16. George Floyd is murdered

    The protests that summer led to the day Gusto stopped to talk (Wikipedia, on this page).

  17. Episode 2

    Andrew Gontarczyk on building a security team (episode 2).

  18. Episode 5

    Leigh Honeywell on online harassment and personal security (episode 5).

  19. Episode 7

    Michael Brooks on why ignoring a risk accepts it (episode 7).

  20. T-Mobile's breach

    T-Mobile confirms a data breach, the one Jon mentions on the tape (Wikipedia, on this page).

  21. This episode

    Flee on the show, then the chief security officer at Gusto (Podbean).

  22. Square becomes Block

    Square, Inc. changes its name to Block, Inc. (Wikipedia, on this page).

  23. Episode 17

    Sean Cassidy on hiring software engineers and teaching them security (episode 17).

  24. Reddit

    CISO, overseeing security, privacy and compliance risks (SecurityWeek, on this page).

  25. Reddit goes public

    The offering raises $600 million (Wikipedia).

  26. Episode 46

    Polina Morozov on green flags and red flags in hiring (episode 46).

  27. Gusto and Guideline

    Gusto agrees to buy Guideline for about $600 million (Wikipedia).

  28. Episode 80

    Ted Harrington on curiosity and the hacker inside everyone (episode 80).

  29. The Reddit role ends

    LinkedIn lists the role through this month (LinkedIn).

What to do this week

Five things, in the order of the episode.

  1. Ask who a feature could hurt. In your next design review, ask how the feature could hurt someone in a different community, and bring in people who know that community, as in Diversity is technically correct.
  2. Put a threat model in the interview. Ask candidates to walk through something that looks like a threat model, and listen for curiosity and communication, as in Hiring for aptitude.
  3. Name an owner for each big risk. Have a business owner sign off on the risk and the outcome of each decision, as in Security savior syndrome. The scorecard covers the rest.
  4. Run the ratio. Put your numbers in the calculator, and pick the security work another team could own, as in Scaling past headcount.
  5. Get help with it. Our vCISO Services give you a senior security leader part time, with a team behind them, Product Security brings security engineers into your product reviews, and 24/7 Monitoring & Response watches your infrastructure and responds hands-on, so your team isn’t carrying it alone. If you want to talk it through, book 15 minutes with us.

Key takeaways

  1. Share what you learn

    The lesson Flee took from IRC and Usenet: people do better when they share what they learn and collaborate.

  2. Culture over prevention

    No CISO can prevent every bad outcome, so the job is a culture of security and resiliency, with the whole company doing security work.

  3. Help the business take risk

    eBay, Square and payroll software all sounded crazy. The CISO's job is to explain risk and help the company take it safely.

  4. Plan to recover

    Flee would rather fail quickly and recover quickly and safely than promise to eliminate every vulnerability.

  5. Hold data as a custodian

    A company doesn't own the data it holds. Each record stands for a person who depends on the company to protect it.

  6. Diversity finds threats

    Lived experiences feed threat models, so a team without diversity can miss a way a product harms someone.

  7. Make it safe to be yourself

    Jon's point: a team can have diversity while people hold back. Flee adds that it has to be psychologically safe to be who you are.

  8. Hire for aptitude

    Look for a threat model walkthrough, curiosity, creative thinking and strong communication. A list of tools, certifications and schools is a bad sign.

  9. Beware security savior syndrome

    Security can't carry every bad outcome. Forgive yourself, build support, take time off and stay calm in a crisis.

  10. Let the business own its risk

    When business owners own the risk of their decisions, security can help, and the culture scales.

  11. Scale past headcount

    The security team will never grow as fast as the company, so each security person has to reach further, with other teams doing part of the work.

Chapters

Tap a chapter to play from there.

Pull quotes

“aggressive exploration and aggressive education.”

Fredrick Lee ·

“it was all about sharing.”

Fredrick Lee ·

“we're better when we collaborate”

Fredrick Lee ·

“sharing our experiences is how teams become stronger than some of their individual parts”

Jon McLachlan ·

“we're just here for the purity of the puzzle.”

Fredrick Lee ·

“it feels a lot like almost like free form jazz.”

Fredrick Lee ·

“getting these various band members together and making their individual performances into a song”

Fredrick Lee ·

“They win by getting the entire company to embrace security”

Fredrick Lee ·

“Risk is where opportunity is, right?”

Fredrick Lee ·

“I'm more interested in being able to fail quickly and recover quickly and safely”

Fredrick Lee ·

“we're going to just stop what we're doing right now.”

Fredrick Lee ·

“We're here to build a better society and a better future.”

Fredrick Lee ·

“It's nice to hear it, but then it's like, then what happens?”

Jon McLachlan ·

“that data really is just a proxy for a human.”

Fredrick Lee ·

“being good custodians and good shepherds of that data”

Fredrick Lee ·

“that small progress over a duration is what fundamentally actually changes the company.”

Fredrick Lee ·

“Bigotry has no place in security.”

Fredrick Lee ·

“security used to always be a refuge for the nerdy outcasts.”

Fredrick Lee ·

“we all have these lived experiences that feed into our personal threat models”

Fredrick Lee ·

“you might literally miss that aspect.”

Fredrick Lee ·

“making it psychologically safe for somebody to actually be who they are is also important.”

Fredrick Lee ·

“security teams, in order to be successful, must be diverse.”

Fredrick Lee ·

“I am certifiable, but I'm not certified.”

Fredrick Lee ·

“really strong at translation and really strong at communication”

Fredrick Lee ·

“Everybody can have some kind of bias.”

Fredrick Lee ·

“We are diverse, but we're not integrated here in the Bay Area.”

Fredrick Lee ·

“this thing that I call security savior syndrome”

Fredrick Lee ·

“That will quickly burn you out.”

Fredrick Lee ·

“You're not supposed to be in this alone”

Fredrick Lee ·

“business owners own the risk and the outcome from their decisions as opposed to security.”

Fredrick Lee ·

“at least display the demeanor of calmness.”

Fredrick Lee ·

“alcohol is not a solution for stress.”

Fredrick Lee ·

“You can literally have your security peers be your therapy”

Fredrick Lee ·

“it's a great way to scale a security culture across an organization.”

Jon McLachlan ·

“Security should be like a highly leveraged discipline.”

Fredrick Lee ·

About the guest

Fredrick Lee, Chief Security Officer, Gusto

Fredrick Lee, known as Flee, was the chief security officer at Gusto at the time of this episode, a role LinkedIn dates from March 2019 to July 2023. LinkedIn lists earlier roles as head of information security at Square, director of security at NetSuite, lead security engineer at Twilio, U.S. information security manager at Betfair, security researcher at Fortify Software, VP at Bank of America, and developer roles at Transcore and Intelis. Reddit named Flee its CISO in July 2023, and LinkedIn lists that role through October 2026. Flee's 2020 TechCrunch op-ed argues that companies should hold personal data as custodians.

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 8 on Podbean: Fredrick Lee, CSO of Gusto, on why authentic diversity is essential for security teams. Source ↗
  • Fredrick Lee's experience on LinkedIn: Intelis, Transcore, Bank of America, Fortify Software, Betfair, Twilio, NetSuite, Square, Gusto and Reddit, with dates. Source ↗
  • Bank Innovation, March 2019: Gusto hires Flee as chief security officer, reporting to co-founder and CTO Edward Kim, with growing the security team as a first task. Source ↗
  • TechCrunch, February 7, 2020: Flee's op-ed on data custodianship and the principle of least privilege. Source ↗
  • O'Reilly, October 31, 2017: an excerpt of Flee's keynote at the O'Reilly Security Conference in New York. Source ↗
  • SecurityWeek, July 31, 2023: Reddit hires Flee as CISO, overseeing information security, privacy and compliance risks, reporting to CTO Chris Slowe. Source ↗
  • Cybersecurity Dive, July 31, 2023: Reddit names Flee CISO to lead its privacy and security teams. Source ↗
  • Wikipedia, 2600: The Hacker Quarterly: a seasonal publication of technical articles, many written by its readers, launched in January 1984. Source ↗
  • Wikipedia, Internet Relay Chat: a text-based chat system built for group discussion in channels, created in August 1988. Source ↗
  • Wikipedia, Usenet: a worldwide distributed discussion system, established in 1980, organized in newsgroups. Source ↗
  • Wikipedia, Free jazz: also known as free form jazz, an experimental approach to improvisation from the late 1950s and early 1960s. Source ↗
  • Wikipedia, eBay: founded in September 1995. Beanie Babies were about 10% of its listings in 1997. Source ↗
  • Wikipedia, Transport Layer Security: a cryptographic protocol for secure communication over a computer network. Source ↗
  • Wikipedia, Murder of George Floyd: May 25, 2020, in Minneapolis. Source ↗
  • Wikipedia, Principle of least privilege: each part of a system gets access only to what its legitimate purpose needs. Source ↗
  • Wikipedia, Threat model: a process for identifying and listing potential threats and prioritizing countermeasures. Source ↗
  • Wikipedia, Psychological safety: the belief that you won't be punished or humiliated for speaking up with ideas, questions, concerns or mistakes. Source ↗
  • Wikipedia, T-Mobile US: the company confirmed a data breach on August 16, 2021. Source ↗
  • Wikipedia, Occupational burnout: the WHO describes it as a work-related phenomenon from chronic workplace stress that hasn't been successfully managed. Source ↗
  • Wikipedia, Gusto: launched as ZenPayroll on December 11, 2012, renamed in September 2015, and past $1 billion in annual revenue by early 2026. Source ↗
  • Wikipedia, Block, Inc.: Square, Inc. changed its name to Block, Inc. on December 10, 2021. Source ↗
  • Wikipedia, Reddit: its initial public offering in March 2024 raised $600 million. Source ↗

Transcript

Automatic transcription. Jon McLachlan hosts this episode with Fredrick "Flee" Lee, then the chief security officer at Gusto. 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, Fredrick Lee, Flee, Gusto, Betfair, NetSuite, Twilio, Transcore, 2600, SPARCstation, Usenet, Venmo, T-Mobile). 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 9,492 words

Jon McLachlan

Hello everyone and welcome to the Security Podcast of Silicon Valley. Today we have a very special guest with us. Fredrick Lee, or Flee, as he sometimes prefers to be referred to, is the chief security officer at Gusto. Before being the chief security officer at Gusto, he was the head of information security at Square, the director of security at NetSuite, over at Oracle, the lead security engineer at Twilio. And you were at Betfair as a security manager, so starting to develop your leadership style there, I imagine. Fortify Software. It looks like you were a security researcher. Ooh, that sounds fun. Did some [red team]? A VP at Bank of America. Awesome. And before that, a Java developer at Transcore and a senior systems developer [at Intelis].

Fredrick Lee

Wow. Yeah, that's going way back. You can see the entire history of Flee throughout the various different dot-com crashes and where I ended up. So it's always good and always interesting here.

Jon McLachlan

No, it sounds like you've always taken full advantage of your opportunities and have become this great leader here in the security worlds. I remember seeing you at BSides, and we bumped into each other also at RSA, and just always coming away with a really warm and fuzzy feeling on the inside about the way that you spoke about security and team building. And I don't even remember what the topics were that we were discussing, but it always had resonated with the values that I bring to the table as well. So let's go back even further. Maybe all the way back to childhood. Was there a moment in childhood that really helped define who you are or see the world? Clearly, you became interested in security at some point.

Fredrick Lee

Yeah, that actually did go back to childhood. I guess you can call it childhood per se. And, you know, obviously, for people who are done listening to audio only, you can't see. I am old. I am unapologetically [Gen X]. I love being [Gen X]. Getting older is a gift, and I love it. And so, like, I got into computers in general super young. And it was partially just because my parents, they put a high emphasis on exploration, building, and education. And anything that they could do to actually help us as children, you know, like learn more about the world, explore different hobbies and things like that, they were always super supportive of. Having said that, though, you know, I did grow up in Mississippi, which in general is just an impoverished area. We didn't grow up with money. And so my parents always were trying to figure out ways, different ways to actually expose us in a way that was economically feasible, but always supportive of us. And so for me, a lot of my exposure to computers actually came through various different schools, occasionally some neighbors, and obviously the library system in Mississippi, which actually is fairly decent. You know, obviously, it could be better, but for me, it was a great resource and a great outlet. What got me into security, one of the things that my dad was really adamant about was us just constantly learning and constantly reading. During the summer, for example, you know, I grew up in a, in Mississippi, what would be considered a small family. So I have three siblings. So there's actually four kids. In Mississippi, that's actually a small family.

Jon McLachlan

Wow, that's small.

Fredrick Lee

Yeah, and things like that. During the summer and things like that, yeah, you have four kids. What are you going to do with them? So, like, you know, literally at least once a week, my mom took us to the library, and we were required to pick out a book and read it. And then we do the same thing the next week, et cetera. And one of the other things my dad liked to do to supplement that is he actually took us to bookstores, even though we couldn't necessarily actually afford to buy things. The great thing about bookstores is you can actually just hang out there and actually read. So for me, as I was actually like dabbling in computers and a lot of the things that people are like familiar with, especially people that [are maybe in the] older generation, you'd pick up like a magazine, maybe something like even something like [Computer Shopper]. And oftentimes there would be articles about things that people were doing with computers, and hey, you have these little sample programs, and there you go. Here's something in BASIC [you'd actually go back and] type into your Tandy or your Commodore 64 or whatever. And eventually I stumbled across this magazine called 2600. As we speak, 2600, I'm a lifetime subscriber. I love this, man. Oh, dude.

Jon McLachlan

[It is] spectacular.

Fredrick Lee

And so as I was reading [them], oh, this seems really interesting. This is really cool because a lot of stuff that people worked on effectively were just puzzles, and it was puzzle solving. And it really didn't resonate with me, this idea of exploration. One of the things that especially caught my attention, though, especially, you know, later in life, was I came across these writings from a hacker. You know, his name is John Lee, John Threat. He was one of the primary members involved in the quote unquote hacker wars of the late 80s, early 90s. And it just triggered a light bulb in my head for several reasons. One, I actually thought what he was doing was really cool. Two, and more impactful, I guess, to me, especially younger, was he was the first hacker and first person, like real person using computers that looked like me. So, for the people who are just audio only, yeah, it's not a special effect if you see the video. I actually am Black. I love being Black. My plan is to continue doing that until I die. It's phenomenal.

Jon McLachlan

That sounds like a fabulous plan. [...]

Fredrick Lee

So far, it's actually working out pretty well for me. But to actually see, you know, John Lee, it's like, wait a second, this guy looks like me. And I actually didn't know his last name at the time. But yes, like [that was the] first Black, like real Black computer scientist that I had seen. And obviously he was also a Black hacker. And he just had like a wealth of knowledge and just his approach towards life, of what I qualify as aggressive exploration. And, you know, like aggressive exploration and aggressive education.

Jon McLachlan

I love how you phrase that. Aggressive exploration. It's so positive. I love it.

Fredrick Lee

Well, and it's because like you think about Jon, even you, like [you probably got] into security because you're really excited about learning new things and having challenges and things like that. Absolutely. And that's kind of like how I got into security. And fortunately, like laws were a little bit different and people didn't really understand the internet as much back then. So my aggressive exploration during like, you know, my teen years or early teen years was something I was actually allowed to continue doing. and actually, I learned a lot. I was fortunate enough to go to a residential high school, the school called Mississippi School for Math and Science. And there we had a wealth of access to computing infrastructure. Everything from just your classic SPARCstations. Yes, I'm that old. I used to play around on.

Jon McLachlan

So for the younger, [late] younger listeners, what is a SPARCstation?

Fredrick Lee

Oh, yeah, yeah, yeah. So SPARCstation was like one of, one of the primary like Unix type workstations provided by Sun Microsystems, the people who quote unquote used to say that they put the dot in the dot-com. And this is early infrastructure, early Silicon Valley, some like the earlier stuff actually going on with networking technology, just high performance computing, et cetera. And this was like super, super old days. And I was super excited. One, because I've been reading about RISC platforms and things like that. And actually, if you worked on a SPARC system, it was like, hey, okay, now I understand a little bit about what it is that you use in RISC architecture as opposed to some of the things that you're doing on the PC side. But my high school, we had a lot of facilities there, and fortunately or unfortunately, the teaching staff wasn't as familiar with computers. So a lot of the administration of computers essentially fell upon the students. And to some extent, I became a de facto sysadmin for the school. And it was like, well, we're actually all just learning. Everybody was learning. Everybody's learning. Yeah. Yeah. So I definitely had my missteps, got into a little bit of trouble. But eventually, with enough indoor suspension and confinement and things like that, I eventually got the message, like, hey, you know, these computers aren't just to play around with, aren't just to wreak havoc with. There's actually other things you can actually do. And I had some really great teachers, in particular, Jack Carter in Mississippi, who really actually helped put me on a better, more legal path for some of the things that I was actually doing, and actually corrected me to have a better fulfilling career than future. So it's not, I am grateful that I'm not in jail, but that probably [was the trajectory] I was [on]. But I was also grateful for the freedom and some of the support, not only that my teachers provided me, and not only that my parents provided me, but the security community that provided me. I think a lot of people just aren't aware of how powerful IRC and Usenet were at the time, and still are. And one of the things I love about the security community, and obviously we're not perfect at all. [I mean], it's far from friendly. It's far from friendly. Something we actually work on. But especially in those early days of the internet, it was all about sharing. Hey, what did you learn? What can you tell me? What can you tell me about this kind of operating system? What can you tell me about this university's computing system? What can you tell me about why you built something that you did? What can you tell me about obfuscating things that you've been working on? What can you tell me about like cracking software? All these other kinds of things. Maybe some of the targets [weren't as positive]. The lessons that you learned were truly positive. And the lesson of sharing information and that we're better when we collaborate was something that I always take with me.

Jon McLachlan

That sounds like a truth that most people miss, that you really latched on to nice and early.

Fredrick Lee

Oh, yeah.

Jon McLachlan

Collaboration and connecting with others and sharing our experiences is how teams become stronger than some of their individual parts, right?

Fredrick Lee

100% agree. 100% agree. And one of the great things about being here in Silicon Valley is that we still see some of that. And like in particular, especially in the open source world. So, like, for me, being a hacker or curious computer user and the open source world just go hand in hand, because it's all about, we're just here for the purity of the puzzle. I want to see what else I can actually do with this machine. I want to see what else we can actually do with humanity. I want to see what else we can actually do by taking somebody else's knowledge and just doing a slight riff on top of that. When I think about how we progress in technology and, in particular, security, it feels a lot like almost like free form jazz. It's like, oh, hey, there's some people who've actually just laid down a melody and hey, can you riff on top of that? Okay, well, now this actually has turned into something else itself. But now there's somebody else who's going to riff on top of that. It's one of the things actually I love [about] security. Also, full disclosure, I'm really passionate about music. This is like, for me, security and jazz and hip hop go hand in hand. It's all about do it yourself. It's all about exploring further beyond the boundaries that people have actually told us existed before and reutilizing things that we've already had in society, right? You think about like, hey, you know, I learned this thing in C, and now all of a sudden I now know how I can create [confirmable] flows. I can do some of these various different things. I can, you know, all these various things. And it's things that we actually just learn from each other. So that's one of the reasons why I'm almost always excited about security.

Jon McLachlan

No, that's, I love the analogy over to the music side of the house, because there is some, there's an art underneath all of the stuff. And it gets to the collaboration as well. When you find that riff and that groove, you can build something really cool very quickly. And you can surprise everyone in the room that happens to be there and share the experience, which is spectacular. So, as the CSO, so what is it like, just a day in the life of

Fredrick Lee

Yeah, the day in the life of CISO, Gusto, and just the day of the life of CISO in general. When you think about a CISO in general, what I actually think is actually a lot of misconceptions. And some of those misconceptions are really like, hey, what is the nature of the role? What do you do on a day-to-day basis? And even more so, what makes you qualified to be a CISO? One of the things that I have found, especially in what I call this new generation of CISOs, is oftentimes now, a lot of times people are CISOs, not necessarily voluntarily. It's like, hey, we needed one and you were here and you weren't smart enough to say no. Right? And that's very slightly tongue-in-cheek. What I've discovered inside of security is most of you inside of security are deeply technical and deeply passionate about being technical. But an interesting thing about being a CISO, and this actually goes back to this idea of collaboration, is part of your role at a CISO is getting these various band members together and making their individual performances into a song or into a [committee]. And it's something that's actually bigger than the individual parts. It's things I actually think about at the CISO, and in particular, you like here at Gusto and other places, is like, hey, how do you actually build a strong team that can perpetuate a security culture? And the reason why I talk about culture, and obviously people would think, hey, one of the things in your mind is the CISO, like, hey, how do you prevent all the bad things happening? The downside of taking the approach like, hey, I'm here to prevent all the bad things happening is that one, we know that's actually not possible. There's always going to be something new that we haven't discovered yet. There's going to be some other, you know, there's going to be some Jon, when Jon was eight, who's going to be tinkering on the internet and find some new exploit. There's going to be another Flee tinkering on the internet, find a new exploit. There's going to be another Sally tinkering on the internet, finding a new exploit. So, the notion that we as CISOs can prevent all bad outcomes is just false. What we can do is that we can help create a culture and environment of security and resiliency so that we can actually figure out, hey, what are they actually just common practices and things that operating rhythms that a company needs to provide more secure outcomes? So that the things you actually are shipping or building or how you actually provide it for your customers are more secure today than they were two days ago, and keeping that momentum going, and even more so, so that more and more people inside of the company are actually doing the work of security. Because that's fundamentally how companies win. They don't win by having one great security team or one great security person. They win by getting the entire company to embrace security and philosophies around it and to be proactive towards actually making better secure outcomes. One of the other things that I think [the CISOs have] to master is this idea of just communications in general. Some people, especially if those people probably aren't from like that Louisiana, Mississippi, Cajun area, they will definitely hear parts of my accent slip out. But you know, like one of the things that's fundamental is our ability to be effective communicators and to explain risk to the entire organization. So that's actually one of the things that is important [for our CISOs], managing that ability to communicate and talk about risk and talk about risk in a way that is right sized for the business. I don't believe that we should eliminate risk. Risk is where opportunity is, right? Hey, if you're investing in the stock market, you're taking a bet. And the idea is, like, hey, you want that risk because that risk is going to allow for an oversized outcome. We wouldn't have the internet as it is today if people weren't taking risks. Like, think about this back in the late 90s when eBay came out and everybody was buying Beanie Babies, et cetera, on eBay.

Jon McLachlan

Oh, I remember those.

Fredrick Lee

Yeah. Well, just think about how crazy it would have been, like how crazy it was, the idea that you're going to put your credit card information or payment information onto the internet and somehow another stranger is going to get paid and you're going to be able to keep the rest of your money, right? Nobody's going to steal your money. That's just a dumb, crazy idea.

Jon McLachlan

It was insane at the time. Saying that they're going to put your credit card information, and a computer is going to whisk away to some other computer, and they're not going to steal it.

Fredrick Lee

Yeah. And you don't even get [...] the very end. You have no idea who that, right, is even involved in this. But because we leverage just math and crypto and things like that, we had SSL, otherwise known as TLS now, to make that more secure. And now we have this entire booming industry, right? You know, when I think about some of the stuff that we did at Square, and I'm still super proud of what Square has built and what Square is continuing to build, a lot of that was like, hey, the dumbest idea ever. Hey, you want to give your credit card over to some random person and have them plug some numbers into their phone? Oh, that sounds super crazy and stupid. But by taking that risk, Square built a multi-billion dollar company. eBay and PayPal built multi-billion dollar companies. By us here at [Gusto] saying, like, hey, we're going to help you with your payroll, and we're going to take some of this sensitive PII and we're going to make that PII useful to you to give you benefits, get you paid, et cetera. That sounds crazy, and it was crazy at the time. But because of taking that risk, you know, now we have this approximately nine and a half billion dollar company that's flourishing. And that's part of the job of the CISO is actually help facilitate risk taking. Right, so one, you actually want to be able to actually correctly articulate risk and be able to actually communicate well to people inside of the company what risk means, what risk do we have. And then you want to actually figure out ways you can actually help facilitate safe risk taking. And it's kind of like this idea that I talk about, and I kind of learned it through Sam Quigley, this notion of pragmatic risk taking. Like, yeah, we're there to actually be business enablers and not people actually say no. So that's what I think of when I think of like the day to day.

Jon McLachlan

The day to day. Facilitate that top end growth, build the business, build something great, build a better future while [taking] calculated risks that are well understood and within reason.

Fredrick Lee

Yeah. And then, you know, the other part is then helping the company build resiliency in case those risks don't pay off. I'm more interested in being able to fail quickly and recover quickly and safely, than I am in saying, like, oh, I'm just going to eliminate all vulnerabilities. There's never going to be anything that actually comes across the board, et cetera. So I think it's more interesting to actually solve that problem, because that helps the business keep moving at speed while still protecting customers.

Jon McLachlan

No, that's spectacular. So, could you put your finger on maybe a single best day that you've had at Gusto so far?

Fredrick Lee

No, this is actually a great question. I've had so many great days at Gusto. I would say probably one of the single best days for me at Gusto. Oh, that's such a good question. There's so many of my, if you wouldn't mind, I want to talk about more than one. Oh, sure. Let's do it. Yeah.

Jon McLachlan

I love good days.

Fredrick Lee

Yeah, yeah. So one of my best days at Gusto was during the summer of, actually, literally just last summer, the summer of 2020, during, you know, like some of the uprising around the George Floyd and the Black Lives Matter protest and things like that. And the reason why one of those days is actually really important to me, and it was like one of my best days, I was personally impacted, not in a, hey, I was there and I was beaten up or something like that by malicious cops. I was deeply impacted once, just as a Black person, and as a Black person, I would argue to say I've been successful, but here in San Francisco, I live in San Francisco. I regularly get stopped by the police. Like, I regularly have to explain, like, no, this actually is my car. I actually live here. This actually is where I [center]. Like, having a company like Gusto, so when that occurred, Gusto just, we essentially said, like, hey, you know what, everybody, we're going to just stop what we're doing right now. And we're going to do a couple of things. Like, one, we're going to talk about this for the entire company. So we just had an all hands for the entire company saying, like, hey, this is what's going on in our community. So, at [Gusto], we truly believe that we are there for the community. We're part of all these ecosystems. And we want to make sure that we can always show up for anybody in our community to actually help them. And that includes our internal employees. And so, hey, let's talk about this. How are you feeling about this as an employee of [Gusto], actually just a member of American society? And not only do we actually talk about it, we say, but what can we do? What can we do to actually put things in action? What can we do to actually show up better and offer more support? And so, you know, we spent a lot of time just as a company just on that day, and then to follow-on actions afterwards. Like, hey, we're not just here to get money from the ecosystem. We're here to build a better society and a better future. So what are things that we can do to actually stand up and really be present for our internal employees, but also for everybody else outside in the ecosystem? And for me, that was actually deeply important. It resonated with me deeply because, first of all, that's actually the first time I've been at a company that was willing to do that. I've been at other companies that talk about diversity, that talk about these things. The [lip service]. First time, actually. Yeah, the [lip service] is one of the easiest things to do.

Jon McLachlan

It's nice to hear it, but then it's like, then what happens? You know?

Fredrick Lee

Yeah. And so we definitely put some action there. The other happy best day for me was when I discovered an internal issue, and I won't go into the details because I don't want my lawyers to beat me up later. But there's like an internal issue that I just wasn't excited about. And it was actually just one of the ways that our engineering team was operating. I was like, hey, you know what? We can do better than this. And I thought that we actually owed it to our customers. This wasn't like a security defect or something like that. Or it wasn't like, oh, no, the company's been compromised. But it was an area that I felt like we could make some significant improvement. And one of the things I was just super proud about is that all the engineers got on board. They were like, hey, Flee, hey, security team, we hear you. You explained this problem to us, and now we're going to act. And so this problem, and it's acting with a problem that previously the engineers just thought couldn't be solved. And they're like, hey, this seems really scary. And this is just how all engineering teams operate. But they were open to hearing the message from myself and other security practitioners inside of Gusto, and just immediately, no argument. It just went right into action. And this is actually what's like, and there's probably tons of listeners who have actually come across some similar things inside of their company that they weren't able to change. But this actually was a great day for me, because it's like, one, it actually was kind of like proving out that the culture that we wanted at Gusto was actually working, and that engineers themselves are like, oh, wow, yes, we totally got to do this. And they were probably more aggressive about getting it fixed and getting it fixed quicker than even I was, because they really internalized the message and the importance of protecting the people that use Gusto's platform. And one of the things I always talk about, [and we] talk about this inside of Gusto, is that we are not data owners. We don't own any data at Gusto. Actually, rather, we own very little data. What we are are data custodians. And that data really is just a proxy for a human. And people at Gusto really understand that those zeros and ones that [we're moving are] just like representations of an actual human in a human life who actually depends upon us to be doing a good job, being protective, being good custodians and good shepherds of that data, and making sure that nobody has a negative surprise from Gusto. And I don't want anybody to ever think that, hey, Gusto did something with my data and that we would ever be embarrassed to talk about it, right? Like, I want us to always be proud and transparent about how we actually utilize some of this data. I feel like there's always some kind of great day that I'm having [at Gusto] every day.

Jon McLachlan

I love those words. You want to be proud and transparent with everything that happens. No, that's really spectacular. And George Floyd, I remember when George Floyd happened, and my heart went out to everyone in Minneapolis and everyone that was impacted in the society in general. I was like, oh, the 2020s are going to be just like the 1960s again. And I actually grew up in Minneapolis. And so I really, when that was on the news, I was like, hey, I used to hang out right there. I went to school there, University of Minnesota. And I've always been irrationally excited about all things security. So in high school, I volunteered with the local police department. So here I was like doing ride-alongs with these police officers, and you would hear the stories, and I knew immediately, oh, this is ripe for change. Like, something needs to change. Like, we need to fix some of these underlying misconceptions. Racism was rampant, and homophobia, transphobia, sexism.

Fredrick Lee

Yes.

Jon McLachlan

It's all of it. I got up close and personal just because my passion drove me into exploring law enforcement, doing ride-alongs. And then later to see all of that unfold on the news, it was, it was unexpected. And I was disappointed that over the 20 years, it didn't change that much.

Fredrick Lee

Yeah, it's interesting, because change has to, change requires catalyst, and it requires resiliency to say like, hey, you know what? Yeah. And this is, I think, is really relevant, because you think about when you join a company, and especially if you're that first security engineer, that first CISO or whatever,

Jon McLachlan

Yep.

Fredrick Lee

you're going to be making a lot of small progress. But that small progress over a duration is what fundamentally actually changes the company. And it is a funny thing to always say that security people, as grumpy as we could appear, probably some of the biggest optimists in the world, because they knew what a better future could look like. They knew what a better future could be.

Jon McLachlan

We all conjure that up in our heads and imagine like what that is going to look like, and then build little roads and struts to help bring us towards there, right?

Fredrick Lee

Yeah. Yeah. And I love the fact that you used to do ride-alongs with the police, because I mostly view most security people as being in that [D&D] good category. Yeah, you might be a little bit more like lawful good. My preference was chaotic good. I'm more of a [anybody].

Jon McLachlan

Oh, I definitely had a chaos side as well. In fact, during high school, while I was volunteering with those group of police explorers and doing the ride-alongs, I came out as gay. So that was quite the experience. And I was like, well, okay, there's a choice here. The choice is like, I could lead a double life and keep everything separate. And it didn't resonate with anything that I wanted to do or how I wanted to lead my life. And so, okay, merge everything together. And I remember coming out with all of those police. I was expecting there to be trouble, to be tension, to be issues. And surprisingly, I was just blown away by everyone's support, which was unexpected. In a conservative high school, in a conservative community, I was expecting to lose friends, but never happened. So it does really get better.

Fredrick Lee

Yeah, I love that story. And one is, I think one of the things I can love about your story is the fact that, one, you were actually willing as a high schooler actually come out. And I think we probably actually have a pretty significant age difference, but I know that some of the struggles for some of my peers and things like that, especially in high school, because we actually lived at the high school. And even more so, Mississippi is not the most tolerant state. But one of the things I think some of my peers had found, and it sounds like you found this as well, is that individuals can be really tolerant. And we, at least, one of the things I always try to keep in mind for me as a minority is I can't paint a broad brush against the police in general, because I actually know some phenomenal law enforcement agents. I also know some horrible people that should never have this job at all. And there's definitely work that can be done there. But I do think that there are things that we also have to keep an open mind, but at the same time, protect our peace. And what I mean by this, I would never ask a trans person here in San Francisco to go up and hug a cop. [It's like], oh, you just have to love the cops. Because there's been a lot of trauma and a lot of history. And some of the signs, you know, the burden shouldn't be placed upon the aggrieved party [to use this]. But it is useful to know that, hey, you know what? The entire world isn't like this. You can be different places. You can have different experiences, et cetera.

Jon McLachlan

As we go through our interactions and we bump into people that are different from us and very different from us, and we bring our full selves to the table, I think that's, those are the little granular components that actually lead to change, that lead to more open-mindedness.

Fredrick Lee

And well, this is actually one of my passion areas. I want more security people to bring their full [selves]. One of the things actually I like about our security community, and what is it, like, our security community can definitely be toxic. And I wrestle with that myself, like, how much of this is actually good? How much is bad? Because there are some significant portions of our culture that just need to be erased. Some of the rampant, just, sure, just straight up just sexism just needs to go away. The gatekeeping just needs to go away. The homophobia just needs to go away. The transphobia, the racism, et cetera. Bigotry has no place in security. I felt passionate about this because, way back in the day, back in my day, kids, one, most of us never even saw each other. We didn't know anything. And so security used to always be a refuge for the nerdy outcasts.

Jon McLachlan

The outcasts. Yeah, exactly.

Fredrick Lee

Yeah. And you could, I used to always joke that if you got into security, there was probably something wrong with you. Like, there's something [wrong].

Jon McLachlan

One of my professors, he took me aside and he was like, oh, I understand now why you're interested in security. It changes your relationship to power. And I was like, I hadn't thought of it like that. And I was taken aback. I was like, well, maybe.

Fredrick Lee

Well, no, I've been transparent. Like, part of the reason why I was so interested in being quote unquote in security or hacker, whatever you call it, is I recognize that me as a young Black kid in Mississippi, just the asymmetry of the power relationship is just horrible. But computers were a great equalizer. And like, hey, you know what? I don't really care about X, Y, and Z. And if I have a racist teacher, I can just change my grades now. If X, Y, and Z is happening in the community, I can, you know, manipulate somebody's information. So now that somebody is no longer getting billed for their electric income and those kinds of things. These are all things that [security act] provides for us. And I think that we are able to take advantage of some of that in our community. And I think especially when I think about now in modern security, we actually have real jobs. Like, first of all, it seemed like back in the day, getting a security job generally made you working for the feds. And because of my background, that was never going to happen. I could never work for the feds. But now we have to have these real security and you have a legal outlet. And the problems that we have, and this [can be interesting], and hopefully this resonates with some of your listeners, the problem that we have now in security is getting more diversity. And I think one of the reasons why diversity is so important in security isn't because, quote unquote, it's the right thing to do. [That's great]. We should be doing it because it's the right thing to do, but even more so, technically it's the correct thing to do. Part of our jobs in security is thinking about all of the bad things that can happen and how do we actually mitigate those. So we all have these lived experiences that feed into our personal threat models and how we actually view the world. For example, I have several queer relatives, and being queer in the South is a scary thing. So the way that they approach navigating society and the things they actually have to, that they want to disclose, what they don't want to disclose informs how they operate. And that's an input that's useful for a security team. You can actually envision, it's like, hey, maybe actually I use some of the public companies. You think about a product like Venmo. Whereas if you use Venmo here in San Francisco, it's like, hey, you know what? I was at [Martuni's], or I was, I paid a bill at [Martuni's], or I was, you actually, I don't think the Eagle ever accepted credit cards. Oh, hey, I've got the Eagle, and somebody saw me or had a video of me, or I paid somebody. That is innocuous here in San Francisco. Yeah.

Jon McLachlan

No one thinks twice about it.

Fredrick Lee

But yeah, yeah. But if you're like rural Alabama, and all of a sudden everybody sees that, hey, you're going to a gay bar or something like that, that can have very real physical consequences for somebody. And if your security team doesn't have that diversity, you might literally miss that aspect.

Jon McLachlan

But one of the things I think we even see, or even if you have the diversity, but people are not bringing their full selves to the table.

Fredrick Lee

Yes, right? Yes, even more so. And I think it's exactly. Yeah. So just [having the diversity isn't enough], making it psychologically safe for somebody to actually be who they are is also important. Think about some of the things. Another example, like, I am six foot one, six foot one, about 250 pounds. I'm a Black guy in San Francisco. Most people cross the street when they see me. I'm not scary. I don't think I'm scary. No, I don't think you're scary at all. No. But my threat profile, walking like in the [Tenderloin] late at night or something like that, it's completely different than one of my friends, Colleen. She's the head of security at Segment and Twilio. She's a much smaller woman. She's, I think, she might be five one, five two. And her threat profile is completely different. And I remember I was having a meetup with her, and I was like, hey, Colleen, let's go. We're going to go to this meetup. And she's like, oh, hey, how are you getting there? It's like, oh, I'm just going to walk. And she's like, oh, I'm going to take an Uber. And I was like, why? I have to walk through this neighborhood to get there, Flee. It's like walking through the same neighborhood. It's, Flee, you look like this. I look like this. And I've been accosted. I've, you know, she's had these experiences with people being hostile, et cetera. And that's just a completely different thing. And that definitely impacts how you want to think about security. When I think about it from a product standpoint, you know, here in California, in particular Silicon Valley, it's not a perfect community, but we are more accepting and we have a little bit more autonomy for things like women's rights and those kind of things. When you think about some areas like in sub-Saharan Africa, and these places where there's a lot more patriarchal society, where maybe a young woman who lives there doesn't actually fully [balloon] her accounts. And so if you're showing and demonstrating things like, oh, well, hey, who's this random guy that reached out to you on LinkedIn, and that actually appears in somebody else, somebody might say, this is against our culture. Why do I want to get out of it? Like, why is this woman doing that? And they could actually have negative consequences for her. Having people with that background that could actually point out those cultural differences and saying, hey, the thing that you're building sounds great, but here are some of the ways that this might impact somebody in my community or community that I'm familiar with. And this actually goes back to kind of the Venmo thing, even like Square Cash, et cetera. There's a lady at [GitHub], Danielle [Leong], she's a director of engineering there. And one of her passions has actually been calling out things around essentially just privacy issues inside of products. And one of them is like, hey, are you setting up some of these products to make it easy for an abuser to still reach out and contact somebody? So, for example, like, hey, you know, for an abusive ex or just an abusive person in general, spending a dollar to send somebody something via Venmo or PayPal, et cetera, just so you can actually add a message saying, hey, go kill yourself, or you're a horrible person, for some malicious people, that's worth it. But there are things that we can do as a security industry to improve those scenarios. And that's part of the, actually, that's, I think for me, that's one of the bulk of the reasons why security teams, in order to be successful, must be diverse.

Jon McLachlan

Right.

Fredrick Lee

And it's actually been a passion area for me. Like, obviously, I want to make it easier for me to be in the industry, but I also want to make it much easier for people [that look like] me or not like me, or fundamentally just different, to still have successful long-term careers inside of security. Like, at the end of the day, it should be all about, can you be a good security practitioner? It shouldn't matter who you date, who you marry, what kind of, if you have kids, what your skin color is, what your gender is, what your sexuality is, et cetera. It should really be about [the output that] we generate and our ability to help create more safe outcomes.

Jon McLachlan

That's spectacular. All of that resonates really well with me and all of my experiences too. I've done a bit of team building myself here in the Valley, and I've noticed that how you set up diversity and our differences and our different experiences as the strengths of the team, you facilitate a camaraderie that you would otherwise miss, right? And it leads to better products. It leads to thinking outside the box. It leads to more innovation. It leads to people feeling like they're contributing to something bigger than themselves and really bringing their full self to the table and really contributing. Everyone. Yeah. And so, given that diversity is this important aspect to building teams in general, security teams in particular, because we have to be the outside-the-box thinkers,

Fredrick Lee

Oh, 100%.

Jon McLachlan

when you interview someone for a senior security role, how do you flush that out? What's the signal that you look for? How do you, is there a strong yes signal that you hit it, or when you smell it? How do you build these sorts of teams?

Fredrick Lee

One of the things actually I look for, especially when I'm thinking about like senior leaders within security, is how do they think about what a good security hire looks like? And not like literally just physical, but like qualifications and things like that. My degree is in electrical computer engineering, right? Now, I don't have a degree [in] security. I have zero certifications, et cetera. I do joke around that I am certifiable, but I'm not certified. Sure. And, you know, the things I can look for is people who recognize what are the actual core fundamental attributes and aptitude that an individual needs to present in order to actually show that they can be effective in cybersecurity. So, like, when I hear a manager or a leader, or even just a senior security person, saying, like, hey, well, this person needs to know all these tools, or oh, this person needs to have these certifications, or they need to come from this school, or they have those,

Jon McLachlan

Kind of nails on a chalkboard, isn't it?

Fredrick Lee

Yeah, I know. I visibly see the rejection on your face. And for me, it's like, oh, no, that's horrible. When I see somebody, oh, hey, you know what? I want to see if somebody can, can they actually walk me through something that looks like a threat model, even if they actually don't [know] those words to me. They have some of these natural aptitudes of curiosity, thinking creatively, et cetera. You know, when I hear people saying, hey, I look for somebody who's really strong at translation and really strong at communication, that makes my eyes light up. When they're saying, like, hey, I'm interested in somebody who has passions outside of security. Cause once [they like, if] somebody is open to a person having passions outside of security. Yeah. And that makes you realize, oh, they're actually just open to all walks of life. Like, I love the fact that your background is super shiny and it's [been] Ducati.

Jon McLachlan

It's an old Ducati. I don't have it anymore, but it was a very fun bike.

Fredrick Lee

But it conveys me like, oh, you are like a full person, and you're not just pigeonholed into this one identity, and that you're capable of actually seeing it, hey, there's actually value in other things besides just security. And that goes a long way. And this isn't to, and I think oftentimes people think, oh, hey, diversity or having issues with diversity is just like a white male problem. That is not true at all. That goes across the gamut. Everybody can have some kind of bias. And so when I really do try to actually tease out what those potentially are and how could they actually work to broaden their horizons, actually get rid of some of those biases. You know, like, I could totally be biased as a Black male and say, hey, I don't want to work with women or something like that. That's a [total day], from the South, and say, like, oh, hey, in southern culture, we're very homophobic, so I don't want to work with anybody that's, you know, LGBTQ, et cetera. It's like all these other kinds of things. So it's not just a area that we have to press upon, like, hey, we have to make sure that white males that we're hiring aren't [clients]. We have to do that across the board, because bias isn't exclusive to one demographic. It's all very capable of that. And if you look here in the Bay Area, you definitely know that this is not, every demographic in the Bay Area probably has some issues with bias against other demographics in the Bay Area that we have to challenge. And I can go on that soapbox forever about my issues with the Bay Area, air quotes, wokeness. We are diverse, but we're not integrated here in the Bay Area. So there's still a lot of work we have to do here as well.

Jon McLachlan

It's true. It's true. The future is not here yet. It's something that we are always chasing. We're always building towards something better.

Fredrick Lee

But I think that's what I love about security people. We're these angry optimists. We're like, no, it could be better. An angry optimist. Yes.

Jon McLachlan

That's a wonderful description. So I know sometimes security can be very stressful and highly visible, especially when the shit starts hitting the fan. I think like what just happened with T-Mobile, my heart goes out for all of the security engineers. Maybe, of course, Gusto, there's nothing like that. But if you had any words of advice for folks that find themselves in a little bit of a pickle, that are in the security space, that are helping their organization navigate a difficult situation, or maybe a ransomware attack or a data breach of some kind, what advice would you have for them?

Fredrick Lee

Yeah, tons. And I think, you know, one of the things [you kind of hit the head on], [...] towards is this thing that I call security savior syndrome, where oftentimes security people, security teams think that they have to carry the burden of all bad outcomes on their shoulders and prevent all bad outcomes at a company. That will quickly burn you out. And it's actually part of the reason we have so much burden on our industry. So first of all, I think one is that anybody in the security industry [has] to learn to give themselves forgiveness, because we cannot prevent every single bad outcome.

Jon McLachlan

And [self-forgiveness], which is such an important quality to bring with us wherever we go.

Fredrick Lee

Oh, yeah. And it's like one of the recommendations I have that for people in security, everybody in security should at least think about, consider getting therapy. It's just a useful thing, just in general. It'll make you better. Practice mindfulness. And I know it sounds like a little bit, you know, [hippie], new agey or whatever.

Jon McLachlan

No, no, not at all. I practice mindfulness.

Fredrick Lee

Yeah.

Jon McLachlan

Yes. Do my 10 minutes of meditation.

Fredrick Lee

It might sound weird talking from this like southern redneck, but those things are actually really important for like that long-term sanity for us in the community. The other thing is make sure that you're working on internal relationships with your company, so you have support. You're not supposed to be in this alone when you're actually going through some of these typical security issues. The other thing that I recommend, and this isn't, this isn't possible for everybody, so I do want to caveat that, is try to shift your company's culture so that business owners own the risk and the outcome from their decisions as opposed to security. And the reason why I mentioned that is that then you can actually really start reframing how you're thinking about some of these problems, like the issue going on with T-Mobile. Obviously, there's another thing going on with AT&T today [as we're recording] this, so that you, as a security practitioner, aren't on the hook for fixing somebody else's mistakes. Right. And so you can actually start approaching this more from a helping angle, as opposed to a CYA angle and some of those other things. This is actually really nuanced. It also depends on your company's culture about how you can approach that. The other thing that I recommend is security people, I would recommend security people to try to take a vacation at least once a quarter. Like, ideally, you should be taking like one week a quarter just to actually recharge yourself. This is, security is a marathon. This is not a sprint type of industry. You get into security because you're working on a lot of like small changes, a lot of things that over duration add up to better outcomes. But that doesn't mean you're going to prevent all negative outcomes. And so you have to be open to the fact that, hey, some bad things are going to happen. In the moment of a crisis, one of the important things for us as security practitioners to be able to do, and this actually will help your own stress, is to at least display the demeanor of calmness. Other people, especially when there's a crisis, they look towards security as almost being like mom and dad, right? And so whatever reaction we have, that just gets amplified. Yes. And so if we, throughout the organization. Yeah, so if you have a security incident and you're saying, like, hey, this is going to destroy the company, the CEO is totally going to help you, and they're going to believe it, and they're going to be really stressed out. And that stress is then going to circle back to you. And that stress then is going to actually trickle out to your team or your peers. [...] [We just think it's that]. Yes, exactly. [It's this] negative feedback loop is going to continue to amplify itself. And ultimately, that stress ends up being embodied into the security practitioners. So it just ultimately isn't helpful. The other thing I would say is, especially when you're in a stressful situation of security, be mindful of your physical health and be mindful of substance abuse. This is one of the things that I do think is actually somewhat negative in our culture. We do have a culture where we celebrate things like drinking and mind-altering substances and [stuff like] that. I'm not judging anybody for any of those things.

Jon McLachlan

Of course. But addiction's a disease.

Fredrick Lee

But it definitely can have a negative consequence towards the other stress that you're feeling. Like, alcohol is not a solution for stress. It can oftentimes make stress worse. And that goes with like other substances that people may abuse. And like I said, I'm not against people using drugs. I am a believer in better living through chemistry, et cetera. But I do think that [gives] responsible usage versus irresponsible usage. And hopefully, you know, [security of these] tricks will initiate it and make it easy for us to fall into some of those traps. So those are some things I think about. It's like, hey, you know, one, you know, making sure that you're actually, you know, relieving and forgiving yourself for security incidents, practicing mindfulness if you can. And that's something if you're open towards speaking to others. You don't necessarily have to have a therapist. You can literally have your security peers be your therapy, versus hanging out on IRC and complaining about, I guess, Slack and Discord for some of the younger people. Those are outlets for you. And trying to also shift the culture of your company so that business owners are actually on the hook for the risk as opposed to security.

Jon McLachlan

Right. Actually, that one in particular, your last one, shifting the risks onto the business owners, it's a great way to scale a security culture across an organization. Now it's not just one place that's responsible, it's everywhere that's responsible, right? And as your org grows, you may not, your security team may not grow at the same rate. So you will, relative to everybody else in the company, have less and less resources to work with a larger and larger set of folks.

Fredrick Lee

So your security team is never going to grow as fast as the rest of you are. And that's just reality. And there are good reasons for that, right? Security should be like a highly leveraged discipline. Most security people are just highly intelligent. We can do a lot. We're really capable. That doesn't mean that we should be superheroes and burn ourselves out. But I know that a good security team can scale in a way that's better than a lot of engineering teams. And so you're never going to be the same size as engineering teams. You're never going to be the same size as marketing teams. The interesting thing is that you are often going to be responsible for security of all the departments and helping everybody, which makes it even more of a weird ratio, because, yeah, the security ratio for the entire company is going to be really small compared to some of the others. But I think it's actually part of the fun of the challenge. I know that I've been talking a lot, Jon, since, [I apologize] for that. No, no, apologies. Not at all. It's wonderful. We are long-winded. We ramble.

Jon McLachlan

We will just close it up by saying a huge thanks to Flee for joining for the show. It's been a really interesting discussion. I love your perspectives on diversity and security and team building and what matters. A huge thanks for joining. Be sure to join us next time on the Security Podcast of Silicon Valley. Thanks, Flee.

FAQ

Questions this episode answers

Who is Fredrick Lee?
Fredrick Lee, known as Flee, was the chief security officer at Gusto on this August 2021 episode, after leading information security at Square and security at NetSuite, with earlier roles at Twilio, Betfair, Fortify Software and Bank of America. Reddit named Flee its CISO in July 2023.
What is security savior syndrome?
Flee's name for the belief that security people must carry every bad outcome and prevent all of them. It burns people out. Flee's advice includes forgiving yourself, building support inside the company, taking time off and staying calm in a crisis.
Why does Flee say diversity is technically correct?
Security means imagining what can go wrong, and lived experiences feed each person's threat model. A team that lacks diversity can miss a harm, such as a payment feed that shows a visit to a gay bar in a place that isn't accepting.
What is a data custodian?
Flee's term for a company that holds personal data in trust. Gusto owns little data, Flee said, and that data is a proxy for a human. Flee's 2020 TechCrunch op-ed argues for building systems around data custodianship.
What does Flee look for when hiring security leaders?
How a leader thinks about a good hire: a threat model walkthrough, curiosity, creative thinking, strong translation and communication, and passions outside security. A list of tools, certifications and schools is a bad sign.
Why should business owners own risk?
Flee's advice is to shift the culture so business owners own the risk and the outcome of their decisions. Security then isn't on the hook for others' mistakes, and Jon called it a way to scale a security culture.
Why shouldn't security try to eliminate risk?
Big outcomes need risk. Flee's examples are eBay, Square and payroll software, which all sounded crazy at first, and the CISO's job is to help the company take risk safely and recover fast.
Why does a security team never keep pace with the company?
The company grows faster than security can hire, so each security person covers more people. Flee's answer is a security team whose reach goes past its headcount, with other teams owning part of the work.
What happened after the episode?
Reddit named Flee its CISO in July 2023. Square became Block in December 2021, and Gusto passed $1 billion in annual revenue by early 2026.
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