Podcast Episode 5

Episode 005 33 min

Leigh Honeywell, Founder and CEO of Tall Poppy, The Human Side of Privacy and Security: Online Harassment and Abuse

with Leigh Honeywell · Tall Poppy

0:00 / 33:00

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Episode 5 of The Security Podcast of Silicon Valley, published July 1, 2021. Host Jon McLachlan, co-founder of YSecurity, talks with Leigh Honeywell, the founder and chief executive of Tall Poppy, which protects employees from online harassment. Leigh describes the personal security gap a whole industry skipped, why harassment so often starts with a password leaked in an old breach, selling protection as an employee benefit for everyone from developer relations to Bob in accounting, two design principles for staying out of people's accounts and being a smart security friend, what an attacker's tactics reveal about their motives, getting law enforcement to take threats seriously, and why your iPhone probably isn't what got hacked.

Episode notes

Join me for an interview with Leigh Honeywell. As founder and CEO of Tall Poppy, she's building tools and services to help companies protect their employees from online harassment and abuse.

Together, we share many vulnerable and authentic moments as we explore online harassment, abuse, and how Tall Poppy helps humans navigate difficult situations while still building a thriving business that makes the web better for all of us.

Hosted by Jon McLachlan — co-founder of YSecurity.

The deep dive

Your smart security friend

Leigh Honeywell, the founder and chief executive of Tall Poppy, on the personal security gap a whole industry skipped, why online harassment so often starts with a reused password, selling protection as an employee benefit for everyone from developer relations to Bob in accounting, building a security product that stays out of your accounts, and what an attacker's tactics say about their motives.

Leigh Honeywell spent years helping people who were under attack online, and she kept seeing the same thing. The harassment was personal, but the way in was ordinary: an old password, a forgotten account, a breach from years before.

“But the accounts on the device, that’s what’s getting compromised. That’s the like juicy target that attackers are going after at a consumer level.”

Leigh Honeywell, at 9:03

Listen · Leigh on episode 5, from 9:03
About 10 seconds: Leigh on what attackers actually go after. The clip stops on its own. Read the full transcript.

Leigh founded Tall Poppy in 2018 and went through Y Combinator’s Summer 2018 batch. The company describes itself as building “tools and services to make personal digital safety accessible to everyone,” with proactive work to keep harassment from escalating and incident response when someone comes under attack (Y Combinator). It sells that protection to employers for their people (Tall Poppy).

Jon McLachlan hosted this one alone, and it aired on July 1, 2021, as the fifth episode of the show, with 70 words of show notes. This page is the rest of it: a section for each part of the conversation with the sources beside it, eleven figures, eighteen clips from the tape, the full transcript, and four tools: a quiz, a scorecard for how ready your company is when an employee is targeted, a calculator that puts survey numbers against your own headcount, and a timeline from Bell Canada to 1Password.

Ancient history

Jon opened by reading Leigh’s résumé back to her, and it covers most of the jobs in security: phone systems, malware operations, a security response team, platform security, the ACLU and venture investing. Leigh’s answer was two words, twice.

“Ancient history, ancient history. Let’s go all the way back, all the way back.”

Leigh Honeywell, at 0:49

Her LinkedIn fills in the dates (LinkedIn). She was a malware operations engineer at Symantec from 2008 to 2010, after it bought MessageLabs. She spent 2011 to 2014 at Microsoft as a security program manager, first with the Microsoft Security Response team and then the Microsoft Security Engineering Center. She was a senior platform security engineer at Heroku from 2014 to 2015, then at Slack, first as a senior staff security engineer and then as security response manager until April 2017. From there she spent a year as a technology fellow at the ACLU, working on legal briefs, public writing and advocacy, before founding Tall Poppy in May 2018.

Since July 2019 she has also been a venture partner at Pioneer Fund, which describes itself as “a fund of 540+ Y Combinator alumni” investing in YC startups (Pioneer Fund).

A timeline of eight entries. Open, 2005, Bell Canada: building phone systems in the early days of voice over IP, by her account on the tape. Open, 2008 to 2010, Symantec: malware operations engineer, after the MessageLabs acquisition. Open, 2011 to 2014, Microsoft: security program manager on the security response team, then the Security Engineering Center. Open, 2014 to 2015, Heroku: senior platform security engineer. Open, 2015 to 2017, Slack: senior staff security engineer, then security response manager. Filled, 2017 to 2018, ACLU: technology fellow on legal briefs, public writing and advocacy. Filled, 2018 to 2024, Tall Poppy: founder and chief executive, through Y Combinator's Summer 2018 batch. Dashed, 2019 on, Pioneer Fund: venture partner at a fund of Y Combinator alumni, part-time.
Leigh's road to Tall Poppy, from her LinkedIn.

A family of lawyers

Jon asked where the drive came from. Leigh started with her parents.

“I grew up in a family of lawyers. Both my parents were lawyers in the Ottawa, Canada area. And so I was very much exposed to sort of analytical thinking and a degree of rigor in tackling ideas that I think is a little unusual.”

Leigh Honeywell, at 1:53

Listen · Leigh on episode 5, from 1:53
About 15 seconds: Leigh on growing up in Ottawa. The clip stops on its own. Read the full transcript.

She was also a downhill ski racer on a regional team, with provincial championships and two near misses at nationals, “by one spot.” Her father ran his own law firm, and she did its IT on trips home from college. That’s where the idea of working for yourself came from.

“I had some, you know, some exposure to that sort of entrepreneurial spirit from a pretty young age, of the idea that you didn’t necessarily need to work for someone, you could work for yourself as a professional”

Leigh Honeywell, at 2:45

The path into security wasn’t straight. She bounced between majors, left university and went to work at Bell Canada.

“Building phone systems. This is like 2005. So it’s like the early, early days of voice over IP. And we were doing stuff that was like really cutting edge.”

Leigh Honeywell, at 3:19

Voice over IP was new then, and Leigh pointed out where it went. Every video call is “the distant descendant of IP telephony,” and people still spend part of every meeting checking that the microphones work.

A voice in the wilderness

Then Jon asked the founder question: what truth did she see that most people missed? Leigh had been working with people facing online harassment, a threat that she said wasn’t being addressed at a technical level or at a policy level, and she saw a gap in the industry itself.

“And we have this whole industry that’s spun up around corporate cybersecurity. I felt like I was this sort of voice in the wilderness in terms of personal security.”

Leigh Honeywell, at 5:45

Listen · Leigh on episode 5, from 5:25
About 30 seconds: Leigh on the gap between corporate and personal security. The clip stops on its own. Read the full transcript.

She put the field’s age in perspective with a comparison from medicine.

“we’re very much in the like, doctors have just discovered that childbirth deaths go way down if you wash your hands. Like, we’re at that phase of computer security.”

Leigh Honeywell, at 5:34

The doctor she’s thinking of is Ignaz Semmelweis, who in 1847 proposed hand washing with chlorinated lime at the Vienna General Hospital’s First Obstetrical Clinic, where childbed fever was killing mothers (Wikipedia). Her point was that security is at the stage where simple habits still make a large difference.

For individuals, the tools had stalled. There was antivirus, then password managers, then a detour through VPNs, whose value to an individual depends on the threat.

“it was so clear that there was this gap in terms of both consumer education, but also consumer tools around personal cybersecurity. And eventually, that sort of dawning realization that there was this problem here led me to start Tall Poppy.”

Leigh Honeywell, at 6:24

Two columns. Left, filled, corporate security, a whole industry spun up around it: laptops, servers and the networks between them, security teams, products and research, zero trust and BeyondCorp, the latest buzzwords. Right, open, personal security, a voice in the wilderness: antivirus, for a zillion years, then password managers, a detour through VPNs, useful depending on the threat, and, dashed, not really anything else.
Two halves of security in 2021, as Leigh describes them.

Commoditized breaches

Jon asked whether Tall Poppy deals with account break-ins and the information they leak. Leigh said the goal is to prevent them, and that most of what happens in harassment cases is ordinary.

“so much of the kinds of attacks that you see in harassment situations, it’s sort of fairly commoditized security breaches. It’s people noticing that you haven’t changed your password on a bunch of sites since the Dropbox breach in 2012.”

Leigh Honeywell, at 6:56

Listen · Leigh on episode 5, from 6:56
About 40 seconds: Leigh on how harassment so often starts with an old password. The clip stops on its own. Read the full transcript.

The attacker doesn’t need a new exploit. They take a leaked password from a credential dump and try it on every account they can find, until one opens.

“And they find your, like, I don’t know, Tumblr account that has like embarrassing content on it or whatever, right?”

Leigh Honeywell, at 7:18

That technique has a name, credential stuffing: stolen usernames and passwords, often from a data breach, used to get into other accounts. Old breaches keep circulating for years. Wikipedia’s Dropbox entry lists the leak of 68 million account passwords on the internet in August 2016.

Leigh didn’t blame the people it happens to.

“And through nobody’s fault, right? Like, this stuff is hard. It’s complicated. It’s honestly pretty tedious.”

Leigh Honeywell, at 7:30

What changes the outcome is timing. People who are worried about harassment are motivated, and that’s when a little help goes furthest.

“That’s going to prevent a lot of those breaches. It’s going to prevent a lot of those account takeovers, a lot of that shared personal information that you didn’t want out there. That little tiny bit of prevention ends up being super, super powerful.”

Leigh Honeywell, at 7:54

Four boxes in a row joined by arrows. Open, an old breach, Dropbox, 2012. Open, a credential dump, the password, shared. Open, tried everywhere, until one opens. Filled, an old account, and harassment starts. Below, where the chain breaks, in Leigh's terms, three boxes: open, change old passwords, untouched since the breach. Open, do the tedious part, with someone who knows how. Dashed, help while it matters, when people are motivated.
How an old breach turns into a harassment incident, and where the chain breaks.

The accounts are the target

Jon said the focus on people is what security usually misses, and Leigh tied it to a wider shift in how companies think about security.

“whether it’s like BeyondCorp or Zero Trust or whatever the latest buzzword is, we’re moving beyond this idea of like there’s a laptop and a server and you have to secure them.”

Leigh Honeywell, at 8:42

BeyondCorp is Google’s implementation of zero trust, the idea that being on the company network shouldn’t earn trust by itself. Leigh’s version for individuals is simpler. Patch the devices, yes, and maybe skip the “pizza box on the network.” The account is what an attacker wants.

That’s the line this page opened with, and it’s the thread through the rest of the conversation. A phone or a laptop is hard to break into. An account protected by a password from 2012 is not.

Two columns. Left, the old picture, secure the machines: open, a laptop, patched. Open, a server, patched. Dashed, the pizza box on the network. Right, what attackers go after: one tall filled box, the accounts on the device, the juicy target, at a consumer level.
Where personal attacks land, devices or accounts.

Working quietly in the background

Jon asked, carefully, whether something in her own life had led to the insight. Leigh said she gets that question all the time, and that her own experience has been mild by comparison.

“the worst that’s happened has been like people like tweeting at my employer trying to get me fired because I told them to go away”

Leigh Honeywell, at 9:38

She also mentioned harassment that followed after she spoke up about an abuse situation, which she said fell more heavily on others than on her. Most of what she learned came from standing next to people facing far worse.

“But very much more ended up being this sort of person who was working quietly in the background with targets, with victims, with survivors, trying to do what I could to help protect them and help them recover from this kind of much more severe situation.”

Leigh Honeywell, at 10:21

Listen · Leigh on episode 5, from 10:21
About 35 seconds: Leigh on where the lessons came from. The clip stops on its own. Read the full transcript.

Those years turned into a company. Jon put it as scaling the help, and Leigh’s answer was short: “That’s what we’re trying for.”

The scale of the problem in 2021 was large. A Pew Research Center survey from September 2020 found that 41% of Americans had personally experienced online harassment, and 25% had faced more severe forms such as physical threats, stalking, sexual harassment or sustained harassment, up from 15% in 2014 (Pew Research Center).

The best and the worst day

Jon asked about the best day at Tall Poppy. Leigh had struggled with the question when he sent it ahead of time, because in her work the most meaningful days are the worst days for someone else.

“The fact that we can be there for them, it’s both the best and the worst day at the same time”

Leigh Honeywell, at 12:11

Her example was a disinformation campaign aimed at one of Tall Poppy’s customers a few months before the recording.

“And we were able to be there for them and help them feel safer and make sure that their information wasn’t sort of being spread about them by helping them take down a bunch of stuff preemptively.”

Leigh Honeywell, at 12:29

Listen · Leigh on episode 5, from 12:18
About 35 seconds: Leigh on the best and worst day. The clip stops on its own. Read the full transcript.

The stakes were physical. She described the outcome as preventing the situation “from escalating into actual in-person physical violence,” and said the relief came with a chill, because it had been “actually pretty scary.”

Two rows of three boxes. Top row, where it was heading, joined by arrows: open, disinformation aimed at a customer. Open, personal information spread about them. Dashed, physical violence in person. Bottom row, what Tall Poppy did: filled, take things down preemptively. Filled, help them feel safer while it was happening. Open, escalation prevented, and still pretty scary.
The disinformation case, from information spreading to violence prevented.

Plan for the worst, hope for the best

Jon shared a moment from his own life when he expected the worst from the people around him and turned out to be wrong. Leigh answered with the paradox at the center of incident response.

“Your discipline as an incident response professional is to be the one doing that thinking of like, what are those scary, scariest possible outcomes? Right. And then what can we do to make them less bad? What can we do to mitigate? What can we do to prevent?”

Leigh Honeywell, at 13:31

Listen · Leigh on episode 5, from 13:27
About 30 seconds: Leigh on the paradox of incident response. The clip stops on its own. Read the full transcript.

The other half of the job is hope.

“And at the same time as you’re doing all of this like worst case scenario planning, you’re still hoping for the best. And it can be a bit like unsettling when it does actually end up okay.”

Leigh Honeywell, at 13:45

That’s a fair description of good incident response anywhere. The plan assumes the worst so that the person in the middle of it doesn’t have to.

Bob in accounting

Jon asked how the business works. Leigh said the product speaks to individuals, but the buyer is usually an employer.

“So the product itself is definitely pitched to individuals, but we’re working on sort of employee benefits model.”

Leigh Honeywell, at 15:24

Listen · Leigh on episode 5, from 16:05
About 55 seconds: Leigh on Tall Poppy's business model and Bob in accounting. The clip stops on its own. Read the full transcript.

Teams with a public face buy first.

“So we tend to sell either to individual teams within an organization, whether it’s maybe the trust and safety team or the developer relations team, where there’s like a real sort of public interface.”

Leigh Honeywell, at 15:42

Trust and safety teams police a platform’s users, and developer relations people are the company’s public voice to developers, so both draw attention from strangers. But Leigh’s ideal customer is the whole company, and her example is someone nobody would think of as a target.

“But sometimes it’s, I always pick on poor Bob in accounting who has like a bad breakup and his ex shares his nudes, and it’s just this whole like dramatic, traumatic situation. And what does Bob do?”

Leigh Honeywell, at 16:04

The usual answer is the employee assistance program, which typically offers confidential counseling and referrals (Wikipedia). Leigh’s point is that a counselor may not have the technical skills, and Bob probably won’t walk into the security team’s office either.

“we as a security field, we haven’t done a great job like helping people feel comfortable asking, hey, like, I’m dealing with this situation, what do I do? Like, there’s often not that trust with something like a security team.”

Leigh Honeywell, at 16:27

With Tall Poppy in place, Bob knows where to go “where there wouldn’t otherwise be resources.” Jon summed it up as a B2B play, and Leigh agreed: “primarily B2B.”

A filled bar, the employer pays, as an employee benefit, with an arrow down to three boxes: open, trust and safety, a public interface. Open, developer relations, a public interface. Dashed, the whole company, the ideal customer. Below, where Bob in accounting could turn after a bad breakup: open, the EAP, counseling, maybe no tech skills. Open, the security team, often not that trust. Filled, Tall Poppy, help where there was none.
Who Tall Poppy sells to, and who it's for.

Here’s Tall Poppy

Jon asked whether the model could work the other way round, with a platform buying protection for its own users. Leigh had already thought about it.

“wouldn’t it be cool if when you reported some particular kind of malfeasance on one of the social platforms, if one of the recommendations was consider tightening up your security, here’s Tall Poppy.”

Leigh Honeywell, at 17:36

Listen · Leigh on episode 5, from 17:36
About 10 seconds: Leigh on a platform pointing its users to help. The clip stops on its own. Read the full transcript.

She said she’d have to convince the platforms first. The longer-term goal was a product sold directly to consumers, and the open question was how to keep the human touch at scale.

“We know that it needs to be a lot more automated, a lot more like chatbot focused. And then the real challenge is, how do you maintain that sort of empathy and connection and supportiveness when it’s literally like a robot, right?”

Leigh Honeywell, at 18:21

Jon offered a name for it: “An empathy bot of some kind.” Leigh answered, “Someday, someday.”

Self-defense tools

Leigh was clear about the limits of a company like hers.

“what can we do as a company basically providing like self-defense tools? Like, these are tools to keep your account safe. And where is the line of responsibility where the platforms actually need to make their own platforms safer?”

Leigh Honeywell, at 18:52

Listen · Leigh on episode 5, from 18:54
About 20 seconds: Leigh on where self-defense ends and platform responsibility begins. The clip stops on its own. Read the full transcript.

“there’s always sort of limits to things that are solved with education versus solved at a structural level.”

Leigh Honeywell, at 19:06

Education helps the person in front of you. Some problems, such as how a platform handles reports, can only be fixed by the platform.

Not in your security context

Jon asked whether the consumer product was a five-year plan. Leigh hoped for two to three, and laid out the two principles behind everything Tall Poppy builds. The first is about access.

“One is not putting ourselves in the user’s security context wherever possible. So we don’t currently ask for any third-party permissions to apps. We don’t have access to any apps, any sort of third-party content.”

Leigh Honeywell, at 19:59

Listen · Leigh on episode 5, from 19:58
About 40 seconds: Leigh on staying out of the user's accounts. The clip stops on its own. Read the full transcript.

When they do add access, it will be the minimum.

“When we do do that down the road, we design our access in a least privileged way. So thinking about, is there a specific API that gives us security information? Can we just look at metadata rather than looking at content?”

Leigh Honeywell, at 20:12

That’s the principle of least privilege applied to a consumer product. The alternative she rejected is the broad grant, “just give me your whole OAuth token,” which would make Tall Poppy itself a target. An OAuth token with full access to someone’s accounts is exactly the kind of thing an attacker would go after.

Two columns. Left, filled heading, stay out of the user's security context, wherever possible: no third-party permissions to apps today, least privilege when access comes, a specific security API where there is one, metadata rather than content, and, dashed, never the whole OAuth token. Right, filled heading, be a smart security friend, not a scary hacker: someone you trust and come to for advice, the real deal, no products you don't need, points you in the right direction, and, dashed, not the hoodie and hands over the keyboard, not the world is on fire.
Tall Poppy's two design principles, side by side.

Your smart security friend

The second principle is about tone.

“We don’t want to do the like shadowy hands over keyboard, hoodie, dark, scary hacker thing. We want to be like your smart security friend that you come to for advice, right?”

Leigh Honeywell, at 20:41

Listen · Leigh on episode 5, from 20:38
About 40 seconds: Leigh on being a smart security friend. The clip stops on its own. Read the full transcript.

The friend tells you the truth and doesn’t sell you things.

“who’s going to give you the real deal, who’s not going to like bullshit you or sell you products that you don’t need, but also is going to like point you in the right direction to stay safe.”

Leigh Honeywell, at 20:54

She contrasted that with the alarm-bell style of most consumer security marketing, the “oh no, the world is on fire, your passwords have been hacked” approach. Fear makes people freeze. A trusted advisor gets them to act.

We don’t control the internet

Jon asked about the worst day, and Leigh pointed out that she had already answered: the best day and the worst day were the same one. The hardest days are different. They’re the ones where nothing technical will help.

“Whether it’s, you know, somebody’s being harassed online and, you know, the attackers are actually like technically sophisticated, using strong anonymity, and they’re just, you know, there actually sometimes isn’t anything for us to do at a like technical level.”

Leigh Honeywell, at 22:11

Listen · Leigh on episode 5, from 22:04
About 50 seconds: Leigh on the days nothing technical will help. The clip stops on its own. Read the full transcript.

Even then there’s work to do, which she described as moral support and risk analysis. But the limits are real.

“We don’t control the internet. My name’s not Jack Dorsey. I can’t ban people from Twitter.”

Leigh Honeywell, at 22:46

Jack Dorsey was Twitter’s chief executive until November 2021, a few months after the recording (Wikipedia). What a firm like Tall Poppy can do is “reduce the burden, reduce the impact,” as Leigh put it when Jon said the work still makes a difference.

Signature moves

Jon asked whether attackers hide behind tools like Tor or just use fake names. Leigh said it varies by the kind of attacker, much as malware groups do.

“There’s whether you’re dealing with like an individual who’s stalking someone over like a romantic obsession, versus a large group of disaffected fans, versus neo-Nazi or other extremist groups.”

Leigh Honeywell, at 23:46

Listen · Leigh on episode 5, from 24:55
About 20 seconds: Leigh on attacker classes and what their tactics reveal. The clip stops on its own. Read the full transcript.

Each group has its own habits, and the technical skill ranges widely.

“all the way from like doing stuff from their home IP address with no, any sort of obfuscation, and under their real name while logged into Facebook, all the way to anonymous remailers, Tor, you know, the tools that you mentioned, hacked proxies and stuff like that”

Leigh Honeywell, at 24:14

An anonymous remailer strips identifying information from email, and a hacked proxy hides where traffic comes from. The interesting part is what the choice of tools says about the person using them.

“Do they know that what they’re doing is kind of wrong, and that’s why they’ve gone to like great lengths to cover their tracks, right? Or are they so convinced of their own righteousness that they’re like sending death threats from their actual Facebook account?”

Leigh Honeywell, at 24:55

That’s how a threat assessment reads a case. The tactics are evidence of motive and self-belief, and the attacker who doesn’t bother hiding can be the more alarming one.

Top, three kinds of attacker Leigh named: one person, a romantic obsession. A large group of disaffected fans. Extremist groups, neo-Nazi or others. Below, how much they hide, from none to a lot: a filled box, no hiding at all, home IP, real name, on Facebook, with an arrow to a dashed box, great lengths, remailers, Tor, hacked proxies. Under the filled box: can mean they're so sure they're right that they send death threats from their actual account. Under the dashed box: can mean they know what they're doing is wrong.
Three kinds of attacker, and what their level of hiding suggests.

Don’t look at the internet

Jon asked whether Tall Poppy works with law enforcement when there are death threats. It does, but from the side.

“Typically, we will act in more of an advisory role where we’re working with the client and they are reporting directly to law enforcement themselves”

Leigh Honeywell, at 25:24

Listen · Leigh on episode 5, from 26:00
About 40 seconds: Leigh on helping people get threats taken seriously. The clip stops on its own. Read the full transcript.

Leigh called Tall Poppy “a tiny little firm” that police wouldn’t know “from a hole in the wall,” so the client makes the report and Tall Poppy helps them make it count. The default response is the problem.

“Because you go to law enforcement and you say, like, I’m getting death threats on the internet. They’re like, oh, well, don’t look at the internet. And that’s not really helpful.”

Leigh Honeywell, at 26:00

What works is preparation.

“Like, getting it taken seriously requires a degree of documentation, requires like an understanding of which parts of law enforcement are going to be more effective at tracking this stuff down or not.”

Leigh Honeywell, at 26:09

She added a harder truth about who gets to use that route at all.

“the folks who face discrimination at the hand of law enforcement are also often the folks that are facing threats online.”

Leigh Honeywell, at 26:32

So the advice has to fit the person. For some targets, going to the police is the obvious step. For others it carries its own risk, and a plan that assumes everyone will report isn’t a plan for everyone.

Three boxes joined by arrows: open, document it, a degree of documentation. Open, pick the right door, the parts of law enforcement that track it down. Filled, the client reports, with Tall Poppy advising. Below, a dashed box, without it: oh, well, don't look at the internet. Beside it, open, not everyone can report safely: the people who face discrimination by law enforcement are often the ones facing threats online.
What it takes to get a threat taken seriously, in Leigh's terms.

Fellow travelers

Jon brought up Belarus, where protests had been met with a crackdown, and the role of online harassment in campaigns like that. Leigh widened it to elections and shutdowns around the world.

“we’re in a fragile time in terms of the intersection of democracy and the internet, whether it’s what we saw in the States with disinformation in the last election.”

Leigh Honeywell, at 27:06

Listen · Leigh on episode 5, from 26:58
About 45 seconds: Leigh on democracy, disinformation and fellow travelers. The clip stops on its own. Read the full transcript.

She was clear that it isn’t Tall Poppy’s focus, but it’s next door to it.

“I think that a lot of the folks in the trenches of disinformation are very much fellow travelers.”

Leigh Honeywell, at 27:37

Jon said misinformation is tied up with the rest of it, and Leigh finished the thought: “It’s tied right in with the hacking and the account takeovers and the leaking of emails and all of that stuff.” Her own best-and-worst day was a disinformation case, and the way in, again, was an account.

Your iPhone’s not getting hacked

Jon asked what success looks like if the consumer business works. Leigh’s answer was about access to good advice.

“I think the key piece there is really that everyone should have access to affordable expert advice on personal security.”

Leigh Honeywell, at 28:17

Listen · Leigh on episode 5, from 28:58
About 45 seconds: Leigh on what consumers actually need. The clip stops on its own. Read the full transcript.

It’s easy to get a broken laptop fixed, she said, and much harder to find out how to keep your digital life safe. The market doesn’t help.

“There’s so much crap in terms of what’s in the market, whether it’s like people selling anti-malware on iOS. Like, your iPhone’s not getting hacked.”

Leigh Honeywell, at 28:57

What gets hacked, in her experience, is the account behind the phone.

“what’s getting hacked is your iCloud account, because you’re reusing your password.”

Leigh Honeywell, at 29:06

She held up an imaginary iPhone to make the cost point.

“Like, it costs like one to three million dollars to hack into this with a one-click exploit, because it’s the same bugs that are used for jailbreaks.”

Leigh Honeywell, at 29:14

That’s her estimate of the market in 2021. The bugs that let people jailbreak an iPhone are the same ones an attacker would need, and they’re expensive, so no one spends them on “an individual random human unless you’re literally Jeff Bezos.” The hack of Jeff Bezos’s phone is the famous exception that proves her rule. For everyone else, it’s typically accounts.

Jon added that the cloud is where the stuff that leaves the device ends up. Leigh had the line for it.

“You know what they say about the cloud? It’s just somebody else’s computer.”

Leigh Honeywell, at 29:48

Two columns. Left, open, hacking the iPhone, rare, and expensive: one to three million dollars for a one-click exploit, in Leigh's 2021 estimate, because it uses the same bugs as jailbreaks, spent on people like Jeff Bezos, not on a random human. Right, filled, hacking the account, typically this one: one password, reused from another site, and the iCloud account behind the phone opens, what a consumer worried about their device should check first.
Breaking into the phone versus breaking into the account.

A tight-knit group

Near the end, Jon gave a shout out to StartOut, a nonprofit for LGBTQ+ and allied entrepreneurs (StartOut), and Leigh described its accelerator.

“The StartOut Growth Lab is the world’s only LGBTQ-focused startup accelerator. We were in the fourth cohort in spring 2019.”

Leigh Honeywell, at 30:25

Listen · Leigh on episode 5, from 30:46
About 20 seconds: Leigh on what a six-month accelerator gave Tall Poppy. The clip stops on its own. Read the full transcript.

Growth Lab takes “zero equity” in the companies it works with and says it has supported 119 founders (StartOut). What Leigh valued was the length.

“It’s six months long, so longer than the sort of average accelerator, and it’s like a tight-knit group.”

Leigh Honeywell, at 30:49

Jon said the authenticity in the group was “just through the roof,” and Leigh put a name on it.

“Yeah, I feel like people let the like the hustle mask down a little bit.”

Leigh Honeywell, at 31:27

Take over their own world

Jon closed by inviting Leigh back once the consumer product had taken over the world. Leigh reframed the ambition.

“Exactly. It’s like take over the world or prevent the world from being taken over.”

Leigh Honeywell, at 31:59

Jon’s version was “Or enable everyone to take over their own world,” and Leigh said she’d buy it. It’s a fair summary of the whole conversation: security that starts with the person, and the accounts they actually live in.

What happened after the tape

When we recorded. The episode aired on July 1, 2021. Leigh mentions a disinformation case “a few months ago” and Jon brings up the recent events in Belarus, so the conversation most likely took place in the first half of 2021.

Tall Poppy kept going. The Y Combinator directory still lists the company as active, with a team of 10 in Ottawa (Y Combinator). Its site sells online harassment protection to organizations and their employees, with proactive risk management and incident response on standby (Tall Poppy).

Leigh’s next roles. She was Tall Poppy’s chief executive until December 2024. Since then she has been Lead Security Strategist for business and executive security at 1Password, working from Ottawa. She has been a founding advisor to iVerify since July 2023, helping it through its spinout from Trail of Bits, and she is still a venture partner at Pioneer Fund (LinkedIn). A password manager company is a natural next stop for someone who spent years tracing harassment back to reused passwords.

A timeline of five entries. Open, July 1, 2021, episode 5: the fifth episode of the show airs. Open, November 2021, Twitter: Jack Dorsey leaves the chief executive role, a few months after Leigh's line about him. Filled, July 2023, iVerify: Leigh becomes a founding advisor, through its spinout from Trail of Bits. Filled, December 2024, 1Password: Leigh leaves the Tall Poppy chief executive role and becomes Lead Security Strategist at 1Password. Dashed, November 2026, Tall Poppy: the Y Combinator directory lists it as active, with a team of 10 in Ottawa.
The public record after the recording.

What holds up best is the order Leigh argued for. Most harassment starts with an account, so start there: unique passwords, a second factor, and someone to call when it happens, for every employee, not only the famous ones.

Did you catch it? A six-question quiz

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

Quiz · six questions

Did you catch it?

Pick an answer for each question, then check your score.

  1. Which breach did Leigh name as the reason old passwords still work for attackers?

    1. A bank breach in 2018
    2. The Dropbox breach in 2012
    3. A phone carrier breach in 2020

    b. "It's people noticing that you haven't changed your password on a bunch of sites since the Dropbox breach in 2012." Transcript, 7:06.

  2. Which teams did Leigh say Tall Poppy usually sells to first?

    1. Finance and legal
    2. IT and the help desk
    3. Trust and safety, and developer relations

    c. "whether it's maybe the trust and safety team or the developer relations team, where there's like a real sort of public interface." Transcript, 15:46.

  3. What is the first of Tall Poppy's two design principles?

    1. Staying out of the user's security context
    2. Monitoring every account in real time
    3. Asking for full access to fix problems fast

    a. "One is not putting ourselves in the user's security context wherever possible." Transcript, 19:59.

  4. What does Leigh want Tall Poppy to be for the people it helps?

    1. A hacker in a hoodie on their side
    2. A smart security friend
    3. An alarm that goes off when they're hacked

    b. "We want to be like your smart security friend that you come to for advice, right?" Transcript, 20:47.

  5. What can it mean when someone sends death threats from their real Facebook account?

    1. That they're convinced of their own righteousness
    2. That they don't know how to use Tor
    3. That they want to be caught

    a. "Or are they so convinced of their own righteousness that they're like sending death threats from their actual Facebook account?" Transcript, 25:03.

  6. When people think their iPhone was hacked, what did Leigh say is usually the real target?

    1. The phone's operating system
    2. Their home Wi-Fi router
    3. Their iCloud account, through a reused password

    c. "what's getting hacked is your iCloud account, because you're reusing your password." Transcript, 29:06.

Is your team ready when someone is targeted?

Eight questions for an employer whose people might be harassed, doxed or locked out of their own accounts, drawn from what Leigh and Jon covered. Each one links the part of the episode it comes from.

Scorecard · eight questions

Is your team ready when someone is targeted?

Answer for your whole company as it stands today, not only the public-facing teams. If two answers fit, pick the lower one.

  1. Do your people use a password manager, with unique passwords on their personal accounts too?

    • No
    • Some of them
    • Yes, and the company pays for it

    "It's people noticing that you haven't changed your password on a bunch of sites since the Dropbox breach in 2012." See Commoditized breaches.

  2. Is a second factor turned on for the personal accounts that matter most, such as email, cloud storage and social media?

    • No
    • For some people
    • Yes, with help to set it up

    "That little tiny bit of prevention ends up being super, super powerful." See Commoditized breaches.

  3. If any employee were harassed or doxed tomorrow, would they know where to get help?

    • No
    • Only some teams would
    • Yes, everyone would

    "And what does Bob do?" See Bob in accounting.

  4. Do your public-facing people, such as trust and safety, developer relations and executives, get personal security help before anything happens?

    • No
    • Only after an incident
    • Yes, before it happens

    "whether it's maybe the trust and safety team or the developer relations team, where there's like a real sort of public interface." See Bob in accounting.

  5. Is there a written plan for the first day of a harassment or doxing incident?

    • No
    • Roughly, in someone's head
    • Yes, written down and tried

    "what are those scary, scariest possible outcomes?" See Plan for the worst, hope for the best.

  6. Would an employee feel comfortable bringing a personal security problem to your security team?

    • No
    • Some would
    • Yes

    "Like, there's often not that trust with something like a security team." See Bob in accounting.

  7. Can you help someone document threats in a way law enforcement will take seriously?

    • No
    • If they ask
    • Yes, we have a template

    "Like, getting it taken seriously requires a degree of documentation" See Don't look at the internet.

  8. Do the security tools you give employees stay out of their personal accounts?

    • No, they ask for broad access
    • Some do
    • Yes, least privilege only

    "we design our access in a least privileged way." See Not in your security context.

Exposed

An old password or a single bad week could become a crisis with nowhere to turn. Start with password managers and a second factor for everyone, and decide who an employee calls when it happens.

Partly covered

Some of your people are protected and some aren't. Extend the help past the public-facing teams, write down the first day of an incident, and make it safe to ask the security team for personal help.

Harassment-ready

Your people have the basics and know where to go. Keep the plan current, practice the documentation step, and check that every tool you hand out stays out of their accounts.

How many of your people have faced online harassment?

National survey rates against your own headcount. The defaults are Pew Research Center’s numbers for U.S. adults, and you can change them.

Calculator

How many of your people have faced online harassment?

Four estimates: your headcount, the share who have faced any online harassment, the share who have faced severe harassment, and the share of your staff a personal security program covers today.

–people who have likely faced online harassment
–people who have likely faced severe harassment
–people a program covers today
–people who faced severe harassment with no program to turn to

At these rates, about 82 of your people have faced online harassment and about 50 have faced severe harassment such as threats or stalking. A program that covers 20 people leaves about 45 of those severe cases with nowhere to turn. That's the gap Leigh's Bob in accounting falls into.

The defaults come from Pew Research Center's September 2020 survey of U.S. adults: 41% had personally experienced online harassment and 25% more severe harassment. They're national rates, not a measurement of your company, so change them if you know your own. The last number assumes the people a program covers are spread evenly across your staff.

From Bell Canada to 1Password

Everything on this page sits on one timeline, from a 19th-century hospital to Leigh’s current role. Filter it by thread.

Timeline · 1847 to 2026

From Bell Canada to 1Password

Filter by thread. Dates are from the public record except where marked as part of this show.

  1. Wash your hands

    Ignaz Semmelweis proposes hand washing in Vienna's First Obstetrical Clinic (Wikipedia, on this show).

  2. Bell Canada

    Building phone systems in the early days of voice over IP, by Leigh's account (on this show).

  3. Independent consulting

    IT and phone systems for small offices in the Toronto area, to 2011 (LinkedIn).

  4. Symantec

    Malware operations engineer, after the MessageLabs acquisition (LinkedIn).

  5. Microsoft

    Security program manager, with the security response team and then the Security Engineering Center (LinkedIn).

  6. The Dropbox breach

    The breach Leigh names as the source of passwords people never changed (on this show).

  7. Heroku

    Senior platform security engineer (LinkedIn).

  8. Slack

    Senior staff security engineer, then security response manager to April 2017 (LinkedIn).

  9. 68 million passwords

    Dropbox account passwords leak onto the internet (Wikipedia).

  10. The ACLU

    Technology fellow, on legal briefs, public writing and advocacy (LinkedIn, her blog).

  11. Tall Poppy

    Leigh founds the company and becomes its chief executive (LinkedIn, on this show).

  12. Y Combinator

    Tall Poppy goes through the Summer 2018 batch (Y Combinator).

  13. StartOut Growth Lab

    Tall Poppy joins the fourth cohort, a six-month program (StartOut, on this show).

  14. Pioneer Fund

    Venture partner at the fund of Y Combinator alumni (LinkedIn, Pioneer Fund).

  15. The state of online harassment

    Pew finds 41% of Americans have experienced online harassment and 25% severe harassment (Pew Research Center).

  16. Episode 5

    The episode airs (transcript).

  17. Dorsey steps down

    Jack Dorsey leaves the Twitter chief executive role (Wikipedia, on this show).

  18. iVerify

    Founding advisor through its spinout from Trail of Bits (LinkedIn).

  19. 1Password

    Leigh leaves the chief executive role at Tall Poppy and becomes Lead Security Strategist at 1Password (LinkedIn).

  20. Still active

    The Y Combinator directory lists Tall Poppy as active, with a team of 10 in Ottawa (Y Combinator).

What to do this week

Five things, in the order Leigh’s argument suggests.

  1. Make a password manager a benefit. Pay for it, roll it out to everyone, and encourage people to use it for personal accounts too. Old, reused passwords are where most harassment cases start. The scorecard above shows where else you stand.
  2. Turn on a second factor where it counts. Email, cloud storage and social media first, with someone available to help people set it up.
  3. Give everyone a place to go. Not only the public-facing teams. The calculator shows how many of your people may already have needed it.
  4. Write down the first day. Who the employee calls, how threats get documented, what gets taken down, and when law enforcement comes in.
  5. Keep your tools out of people’s accounts. Least privilege applies to the help you give, too. If you’d like a second pair of eyes on the program, our vCISO team can help, and you can book 15 minutes with us.

Key takeaways

  1. Personal security was the gap

    In 2021 a whole industry had grown around corporate security, while individuals had antivirus, password managers and a detour through VPNs. Leigh founded Tall Poppy in 2018 to close that gap for people facing online harassment.

  2. Most harassment starts with an ordinary breach

    Attackers in harassment cases rarely need new exploits. They take a password leaked years ago, such as one from the 2012 Dropbox breach, try it on every account and find the one nobody updated.

  3. Help people while they're motivated

    Basic security hygiene is tedious, and it isn't anyone's fault that it gets skipped. People worried about harassment are ready to act, and a little prevention at that moment heads off account takeovers and leaks.

  4. Accounts, not devices, are the target

    The shift behind BeyondCorp and zero trust applies to individuals too. You still patch the laptop, but the accounts on the device are what attackers go after.

  5. The lessons came from the people under attack

    Leigh's own experience was mild by comparison, with people tweeting at her employer to get her fired. Most of what she knows came from working quietly beside targets, victims and survivors.

  6. The best day can also be the worst

    Tall Poppy's most meaningful days are a customer's worst. In a disinformation case months before the recording, it took material down preemptively and kept the situation from escalating into physical violence.

  7. Plan for the worst, hope for the best

    Incident response means thinking through the scariest outcomes and how to mitigate or prevent them, while still hoping it ends well. It can feel unsettling when it does.

  8. Sold to employers, built for individuals

    Tall Poppy pitches its personal security advice to individuals and sells it as an employee benefit, usually first to trust and safety or developer relations teams with a public face.

  9. Cover Bob in accounting too

    Anyone can be targeted, including someone whose ex shares intimate photos after a breakup. An employee assistance program may lack the technical skills, and people rarely trust the security team with personal problems.

  10. Self-defense has limits

    Tools that keep an account safe are self-defense. Some problems can only be solved at a structural level, by the platforms that have to make themselves safer.

  11. Stay out of the user's security context

    Tall Poppy's first design principle is to avoid becoming a risk itself: no third-party permissions for now, least privilege when access comes, and metadata rather than content.

  12. Be a smart security friend

    The second principle is tone. Tall Poppy wants to be the trusted friend who gives the real deal and doesn't sell you what you don't need, not the hoodie hacker or the alarm that the world is on fire.

  13. Some days nothing technical will help

    When attackers are sophisticated and anonymous, there may be nothing to do at a technical level. Moral support and risk analysis still reduce the burden, but no firm controls the internet.

  14. Tactics reveal motive

    Attackers range from one obsessed person to large groups and extremists, and from no hiding at all to remailers, Tor and hacked proxies. Someone sending death threats from their real account may be convinced of their own righteousness.

  15. Documentation gets threats taken seriously

    Tall Poppy advises clients who report directly to law enforcement. Getting past don't look at the internet takes documentation and knowing which part of law enforcement can act, and not everyone can report safely.

  16. Your iPhone's not getting hacked

    A one-click iPhone exploit costs one to three million dollars, in Leigh's 2021 estimate, so it isn't spent on ordinary people. What gets hacked is the iCloud account behind the phone, through a reused password.

Chapters

Tap a chapter to play from there.

Pull quotes

“Ancient history, ancient history.”

Leigh Honeywell ·

“I grew up in a family of lawyers. Both my parents were lawyers in the Ottawa, Canada area.”

Leigh Honeywell ·

“I was a downhill ski racer, raced on a regional team for a few years.”

Leigh Honeywell ·

“you didn't necessarily need to work for someone, you could work for yourself as a professional”

Leigh Honeywell ·

“Building phone systems. This is like 2005. So it's like the early, early days of voice over IP.”

Leigh Honeywell ·

“That's how the distant descendant of IP telephony.”

Leigh Honeywell ·

“So I spent many years working with people who were dealing with a particular type of online security threats that wasn't really getting addressed at a technical level or an organizational slash policy level.”

Leigh Honeywell ·

“doctors have just discovered that childbirth deaths go way down if you wash your hands. Like, we're at that phase of computer security.”

Leigh Honeywell ·

“I felt like I was this sort of voice in the wilderness in terms of personal security.”

Leigh Honeywell ·

“it was so clear that there was this gap in terms of both consumer education, but also consumer tools around personal cybersecurity.”

Leigh Honeywell ·

“So, our goal is to prevent hacks.”

Leigh Honeywell ·

“It's people noticing that you haven't changed your password on a bunch of sites since the Dropbox breach in 2012.”

Leigh Honeywell ·

“And through nobody's fault, right? Like, this stuff is hard. It's complicated. It's honestly pretty tedious.”

Leigh Honeywell ·

“That little tiny bit of prevention ends up being super, super powerful.”

Leigh Honeywell ·

“And I feel like in cybersecurity in general, we oftentimes miss that, that behind all of these stories, there are people.”

Jon McLachlan ·

“But the accounts on the device, that's what's getting compromised. That's the like juicy target that attackers are going after at a consumer level.”

Leigh Honeywell ·

“the worst that's happened has been like people like tweeting at my employer trying to get me fired because I told them to go away”

Leigh Honeywell ·

“But very much more ended up being this sort of person who was working quietly in the background with targets, with victims, with survivors”

Leigh Honeywell ·

“Right. So that you can actually not just help individuals, but scale that help”

Jon McLachlan ·

“That's what we're trying for.”

Leigh Honeywell ·

“The fact that we can be there for them, it's both the best and the worst day at the same time”

Leigh Honeywell ·

“hey, we prevented this situation from escalating into actual in-person physical violence”

Leigh Honeywell ·

“Your discipline as an incident response professional is to be the one doing that thinking of like, what are those scary, scariest possible outcomes?”

Leigh Honeywell ·

“you're still hoping for the best. And it can be a bit like unsettling when it does actually end up okay.”

Leigh Honeywell ·

“Visibility can go a long way.”

Jon McLachlan ·

“So the product itself is definitely pitched to individuals, but we're working on sort of employee benefits model.”

Leigh Honeywell ·

“whether it's maybe the trust and safety team or the developer relations team, where there's like a real sort of public interface.”

Leigh Honeywell ·

“I always pick on poor Bob in accounting who has like a bad breakup and his ex shares his nudes, and it's just this whole like dramatic, traumatic situation.”

Leigh Honeywell ·

“Like, there's often not that trust with something like a security team.”

Leigh Honeywell ·

“He knows that he can go to Tall Poppy and get support in this kind of like edge case of personal security, personal privacy situation where there wouldn't otherwise be resources.”

Leigh Honeywell ·

“At the end, primarily B2B.”

Leigh Honeywell ·

“if one of the recommendations was consider tightening up your security, here's Tall Poppy.”

Leigh Honeywell ·

“how do you maintain that sort of empathy and connection and supportiveness when it's literally like a robot, right?”

Leigh Honeywell ·

“An empathy bot of some kind.”

Jon McLachlan ·

“Like, these are tools to keep your account safe.”

Leigh Honeywell ·

“there's always sort of limits to things that are solved with education versus solved at a structural level.”

Leigh Honeywell ·

“One is not putting ourselves in the user's security context wherever possible.”

Leigh Honeywell ·

“Can we just look at metadata rather than looking at content?”

Leigh Honeywell ·

“We want to be like your smart security friend that you come to for advice, right?”

Leigh Honeywell ·

“who's not going to like bullshit you or sell you products that you don't need, but also is going to like point you in the right direction to stay safe.”

Leigh Honeywell ·

“It's that media training coming to good use.”

Leigh Honeywell ·

“We don't control the internet. My name's not Jack Dorsey. I can't ban people from Twitter.”

Leigh Honeywell ·

“and we can actually be there for someone and just reduce the burden, reduce the impact.”

Leigh Honeywell ·

“in the same way as your malware groups have different signatures.”

Leigh Honeywell ·

“What do the tactics say about the motivations and the self-belief of the person perpetrating this kind of harassment?”

Leigh Honeywell ·

“Or are they so convinced of their own righteousness that they're like sending death threats from their actual Facebook account?”

Leigh Honeywell ·

“Law enforcement doesn't know us from a hole in the wall.”

Leigh Honeywell ·

“They're like, oh, well, don't look at the internet. And that's not really helpful.”

Leigh Honeywell ·

“Like, getting it taken seriously requires a degree of documentation”

Leigh Honeywell ·

“the folks who face discrimination at the hand of law enforcement are also often the folks that are facing threats online.”

Leigh Honeywell ·

“we're in a fragile time in terms of the intersection of democracy and the internet”

Leigh Honeywell ·

“I think that a lot of the folks in the trenches of disinformation are very much fellow travelers.”

Leigh Honeywell ·

“everyone should have access to affordable expert advice on personal security.”

Leigh Honeywell ·

“There's a lot of bad advice out there.”

Leigh Honeywell ·

“what's getting hacked is your iCloud account, because you're reusing your password.”

Leigh Honeywell ·

“So nobody's like using, like, hacking into your iPhone as an individual random human, unless you're literally Jeff Bezos.”

Leigh Honeywell ·

“It's just somebody else's computer.”

Leigh Honeywell ·

“It's six months long, so longer than the sort of average accelerator, and it's like a tight-knit group.”

Leigh Honeywell ·

“Yeah, I feel like people let the like the hustle mask down a little bit.”

Leigh Honeywell ·

“It's like take over the world or prevent the world from being taken over.”

Leigh Honeywell ·

About the guest

Leigh Honeywell, Founder and former Chief Executive Officer, Tall Poppy

Leigh Honeywell founded Tall Poppy in 2018, a company in Ottawa that protects employees from online harassment, and led it as chief executive until December 2024. Before that she was a technology fellow at the ACLU and worked in security at Slack, Heroku, Microsoft and Symantec. She has been a venture partner at Pioneer Fund since 2019, a founding advisor to iVerify since 2023, and since December 2024 Lead Security Strategist for business and executive security at 1Password.

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

  • Leigh Honeywell's LinkedIn experience: 1Password since December 2024, iVerify since July 2023, Pioneer Fund since July 2019, Tall Poppy from May 2018 to December 2024, the ACLU from 2017 to 2018, Slack from 2015 to 2017, Heroku from 2014 to 2015, Microsoft from 2011 to 2014 and Symantec from 2008 to 2010. Source ↗
  • Y Combinator, Tall Poppy: protecting your employees against online harassment, Summer 2018 batch, founded 2018, team of 10, Ottawa, active. Source ↗
  • Tall Poppy, home page: online harassment protection for organizations and their employees, with proactive risk management and incident response. Source ↗
  • Pioneer Fund: a fund of 540+ Y Combinator alumni investing in Y Combinator startups. Source ↗
  • Pew Research Center, The State of Online Harassment, January 13, 2021: 41% of Americans have personally experienced online harassment and 25% more severe harassment. Source ↗
  • StartOut, a nonprofit for LGBTQ+ and allied entrepreneurs. Source ↗
  • StartOut Growth Lab: a startup accelerator that takes zero equity, with 119 founders supported. Source ↗
  • Leigh Honeywell, Joining the ACLU, April 3, 2017. Source ↗
  • Wikipedia, Ignaz Semmelweis: proposed hand washing with chlorinated lime at the Vienna General Hospital's First Obstetrical Clinic in 1847. Source ↗
  • Wikipedia, credential stuffing: stolen account credentials, often from a data breach, used to gain unauthorized access to other accounts. Source ↗
  • Wikipedia, Dropbox: the leak of 68 million account passwords on the internet in August 2016. Source ↗
  • Wikipedia, BeyondCorp: Google's implementation of zero trust. Source ↗
  • Wikipedia, zero trust architecture. Source ↗
  • Wikipedia, employee assistance program: confidential assessments, short-term counseling, referrals and follow-up for employees. Source ↗
  • Wikipedia, principle of least privilege. Source ↗
  • Wikipedia, OAuth. Source ↗
  • Wikipedia, Tor, the anonymity network. Source ↗
  • Wikipedia, anonymous remailer. Source ↗
  • Wikipedia, threat assessment and management. Source ↗
  • Wikipedia, Jack Dorsey: chief executive of Twitter until November 2021. Source ↗
  • Wikipedia, iOS jailbreaking. Source ↗
  • Wikipedia, Jeff Bezos phone hacking incident: a forensic firm claimed in January 2020 that the phone was hacked in May 2018. Source ↗
  • Wikipedia, tall poppy syndrome: a term from Australia and New Zealand for cutting down people with notable success. Source ↗
  • Wikipedia, 1Password. Source ↗
  • The Security Podcast of Silicon Valley, episode 5 on Podbean: Leigh Honeywell, founder and CEO of Tall Poppy, July 1, 2021. Source ↗

Transcript

Automatic transcription. Jon McLachlan hosts this episode with Leigh Honeywell. There is no diarization on the tape, so speaker labels were assigned from the content and checked passage by passage against reference recordings of each voice from this episode, and a few short lines may sit with the wrong speaker. Names were normalized where the recognizer misheard them (Leigh Honeywell, Tall Poppy, Pioneer Fund, Heroku, BeyondCorp, StartOut, NetworQ). Words in [brackets] are best guesses where the audio is unclear, and one unclear word at 14:05 is marked with an ellipsis. Answers are transcribed as spoken, with repeated words and false starts trimmed. Short backchannels are left out.

Read the full transcript 5,616 words

Jon McLachlan

So, welcome everyone to The Security Podcast of Silicon Valley. I'm here today with a very special guest, Leigh Honeywell, founder and CEO of Tall Poppy. And prior to that, you were involved as a venture partner at the Pioneer Fund, as still are, actually. Now you're a senior partner.

Leigh Honeywell

Yeah, that is a sort of parallel thing.

Jon McLachlan

And you were a technology fellow for the ACLU. Excellent work there. And a security response manager for Slack, a security engineer, a senior platform security developer at Heroku, now a Salesforce.com company, and Microsoft. And oh, you did some independent consulting, not to mention you were at Symantec as a malware operations engineer. Wow.

Leigh Honeywell

Ancient history, ancient history. Let's go all the way back, all the way back.

Jon McLachlan

So, technology application specialist as well at Bell Canada. [Wow], so you really came up through the engineering ranks.

Leigh Honeywell

Absolutely. Building phone systems.

Jon McLachlan

Love to get your hands dirty. No, we have a great show scheduled for everyone today. We are going to give Leigh an opportunity to tell us a little bit about her background, sort of the passions that were driving this mission here with Tall Poppy, a little bit about Tall Poppy and then what it's like. So thank you so much.

Leigh Honeywell

Thanks for thinking of me as a guest, and I'm happy to be here.

Jon McLachlan

Absolutely. So oftentimes as a founder, there's a big part of all of this that's very passion driven. And sometimes that can come from, you know, childhood. And so I'm kind of curious if you'd share a little bit about your childhood or what parts of that really made you the interesting and very cool person that you are today.

Leigh Honeywell

Well, thank you. Yeah, I mean, I grew up in a family of lawyers. Both my parents were lawyers in the Ottawa, Canada area. And so I was very much exposed to sort of analytical thinking and a degree of rigor in tackling ideas that I think is a little unusual. I also was a pretty serious athlete when I was growing up. I was a downhill ski racer, raced on a regional team for a few years. Many provincial championships. I missed going to nationals a couple times by one spot, which always was a bit of a heartbreaker. But my dad ran his own law firm for a number of years when I was very small. And then he was part of various larger firms. And then right as I was leaving for college, he forged out his own path again, and I did IT for his small law firm for a number of years. On trips home, I would fix whatever was broken, that kind of thing. But I had some, you know, some exposure to that sort of entrepreneurial spirit from a pretty young age, of the idea that you didn't necessarily need to work for someone, you could work for yourself as a professional or as a, you know, whatever the sort of industry was. So that was always like part of my realm of possibilities. But then I went to college, university as we call it in Canada, and bounced around a couple different majors, didn't really sort of know what my path was for a few years. And I actually ended up dropping out and worked at the phone company, Bell Canada, for a little bit. Building phone systems. This is like 2005. So it's like the early, early days of voice over IP. And we were doing stuff that was like really cutting edge.

Jon McLachlan

I remember when that came out. Everyone is very excited about it.

Leigh Honeywell

And it's so funny to think of like, that was like the cutting edge. And now we spend literally our entire day on

Jon McLachlan

a Zoom, right?

Leigh Honeywell

That's how the distant descendant of IP telephony. Yeah. And yet we still spend how many minutes per hour making sure that everyone's microphone is working, and oh, my camera's cutting out, like, got to reboot my computer, yada, yada, yada. So we're not quite there yet. I've been very fortunate to have this like pretty varied, interesting career wearing a lot of the different hats in cybersecurity.

Jon McLachlan

Nice. And so you come from a family almost of entrepreneurs. Really look up to your dad, it sounds like, and then you've got the competitive spirit in you with the downhill ski racing. Very nice. I love downhill skiing, though in Minnesota there was never any hills worth skiing, really. So the little [bunny] hills. The little [bunny] hills, yes. You have to drive three or four hours to get to the little [bunny] hills. Okay, so in terms of a truth that you really see in the world that most people missed, or was the inspiration for building Tall Poppy, can you share a little bit about vision or how it all came to fruition?

Leigh Honeywell

I love this question because I think it's, you know, what is the sort of core insight? So I spent many years working with people who were dealing with a particular type of online security threats that wasn't really getting addressed at a technical level or an organizational slash policy level. And I'm talking about online harassment, of course. And the thing that I kept seeing over and over again was that fundamentally, when you look at the past 20 years of cybersecurity product development and research, and it's, I say the past 20 years, but it's sort of funny because our field is only like 40 years old, maybe. Right? If even. Like, we're very much in the like, doctors have just discovered that childbirth deaths go way down if you wash your hands. Like, we're at that phase of computer security. And we have this whole industry that's spun up around corporate cybersecurity. I felt like I was this sort of voice in the wilderness in terms of personal security. And, you know, we've had antivirus for a zillion years, and then password managers started to be a thing. And then there's a whole sort of detour through like VPNs, which is complicated as to whether or not VPNs actually protect individuals, particularly, depending on the threats that you're thinking about. But there wasn't really anything else. And when I was working with folks dealing with these harassment issues, you know, people breaking into their personal accounts, sharing their personal data, over and over again, it was so clear that there was this gap in terms of both consumer education, but also consumer tools around personal cybersecurity. And eventually, that sort of dawning realization that there was this problem here led me to start Tall Poppy.

Jon McLachlan

So you do actually deal with account break-ins and the personal information that is sometimes leaked, or the fallout from a

Leigh Honeywell

So, our goal is to prevent hacks. And obviously, you can never prevent 100% of things, but we've found in our work that so much of the kinds of attacks that you see in harassment situations, it's sort of fairly commoditized security breaches. It's people noticing that you haven't changed your password on a bunch of sites since the Dropbox breach in 2012. And they just take that password, which is like widely shared [in] credential dumps, and try it on all your accounts. And they find your, like, I don't know, Tumblr account that has like embarrassing content on it or whatever, right? Like, wherever it is that that sort of basic cybersecurity hygiene hasn't been performed. And through nobody's fault, right? Like, this stuff is hard. It's complicated. It's honestly pretty tedious. And being able to like raise that bar, raise that like difficulty level by getting folks to understand, when they're in a motivated situation because they're concerned about harassment, getting them to understand what are the concrete things that they can do to improve their personal security. That's going to prevent a lot of those breaches. It's going to prevent a lot of those account takeovers, a lot of that shared personal information that you didn't want out there. That little tiny bit of prevention ends up being super, super powerful.

Jon McLachlan

Excellent. No, I really love that. I love that because you're really focused on the people. And I feel like in cybersecurity in general, we oftentimes miss that, that behind all of these stories, there are people. And we have our accounts, we have our data. And I've talked with a lot of professionals, and everyone gets excited about the technologies and the products. But I feel like this focus is really on the people.

Leigh Honeywell

Yeah, absolutely. And I think it sort of parallels a shift, a wider shift. You know, we've, in so many ways, and whether it's like BeyondCorp or Zero Trust or whatever the latest buzzword is, we're moving beyond this idea of like there's a laptop and a server and you have to secure them. Right, let's get the pizza box on the network that keeps the devices safe. Oh, what are we patching the devices? Like, yeah, you have to do all that stuff. I mean, maybe not the pizza box, but like you do need to install the patches. But the accounts on the device, that's what's getting compromised. That's the like juicy target that attackers are going after at a consumer level. And so that's really been our focus.

Jon McLachlan

No, that's a spectacular. So was there any specific incidents in your life that led you to see this grand insight, or? Or was it, maybe that's a very personal question?

Leigh Honeywell

No, it's okay. And I, it's one that I get asked all the time, is like, you know, what is your sort of personal experience of online harassment? And I, in many ways, have been really fortunate that, you know, the worst that's happened has been like people like tweeting at my employer trying to get me fired because I told them to go away, or what, you know, whatever the sort of like fairly mundane in the grand scheme of online harassment is. I was also a sort of MeToo, pre-MeToo whistleblower about an abuse situation, and that resulted in a small amount of harassment for me, but quite a bit of harassment towards some of the other victims. And I think there was like a German newspaper that called me a whore in German. Which, whatever, I don't care. Like, I feel like that says more about them than it does about me, like, whatever, guys. And so, there, you know, there I had some personal experience with it. But very much more ended up being this sort of person who was working quietly in the background with targets, with victims, with survivors, trying to do what I could to help protect them and help them recover from this kind of much more severe situation. And that was really where the lessons were learned, in working directly with people who were facing some of the worst kinds of attacks that individuals have ever faced on the internet, and learning, you know, having the privilege of learning from them and being able to roll those lessons into this thing that we're building.

Jon McLachlan

Right. So that you can actually not just help individuals, but scale that help, to help many, many individuals, and built a nice company around it, too. Well, that sounds great. Props to you for taking full advantage of all of those. You know, it's hard-won lessons, hard, hard lessons learned, and really being the change that you would like to see in the world, right?

Leigh Honeywell

That's what we're trying for.

Jon McLachlan

Excellent. So can you tell me what's been the best day in your journey at Tall Poppy so far?

Leigh Honeywell

Oh man. You sent me this question ahead of time, and I was like, I was struggling with it. I was really struggling with it. So many, you know? I mean, I think there's been so many sort of private wins in terms of the like team environment that I've been able to build, the level of camaraderie of supporting each other as a team when we're dealing, you know, we're dealing with really tough incidents that our customers are facing. And it's so, like, there's this sort of conflict of sometimes like the most meaningful days are the worst days for people, right? It's like there's that terrible, terrible, scary incident that a customer is dealing with. The fact that we can be there for them, it's both the best and the worst day at the same time, because, you know, there's a terrible thing going on. Maybe it's like we were dealing with this disinformation situation targeting one of our customers a few months ago. And, you know, it was actually like legit super scary. And we were able to be there for them and help them feel safer and make sure that their information wasn't sort of being spread about them by helping them take down a bunch of stuff preemptively. That's an amazing feeling to be able to say, like, hey, we prevented this situation from escalating into actual in-person physical violence, but it's still, it's very bracing to say, like, hey, this was actually pretty scary.

Jon McLachlan

Yeah, I could only imagine, I guess for myself personally on the harassment front. When I came out in high school, was a conservative high school. I was in a conservative household. I was sure I was going to lose friends and face harassment. But, you know, you do those things one at a time, and I was very fortunate that actually I was completely mistaken. But the things that were running through my mind, even though I didn't actually

Leigh Honeywell

Anticipate, the sort of fear of what might happen. Yeah. And the sort of, there's this like paradox in terms of incident response. Your discipline as an incident response professional is to be the one doing that thinking of like, what are those scary, scariest possible outcomes? Right. And then what can we do to make them less bad? What can we do to mitigate? What can we do to prevent? And at the same time as you're doing all of this like worst case scenario planning, you're still hoping for the best. And it can be a bit like unsettling when it does actually end up okay. And, you know, I have sort of a quiet hope that, like, and maybe scream it from the rooftops hope that, you know, more kids growing up and coming out will have that experience. I, you know, I am … and remember telling my folks at some point and just being like, cool, we love you. Right, like, and that's great. Like, there's never, and I'm very fortunate that I, you know, never had any question growing up that that would be like a big deal. Right. And so I really hope that we, like, as the sort of generational turnover happens, that more and more people, it's just like, oh, whatever, this is cool.

Jon McLachlan

Yeah, I think that's even starting to happen without generational turnover, too. I've seen people change, like, many people change my lifetime, which makes me really optimistic and happy for the future.

Leigh Honeywell

Right. So I have a family member who growing up was like, not so sure about this whole gay marriage thing, and then watched several seasons of Modern Family and just got it. Just like, got it. Yep. Yeah. Honest representation matters.

Jon McLachlan

Awesome. It does. Visibility can go a long way. Just a little bit of visibility take you so far in social change. That's spectacular. So I'm super curious now. Tall Poppy sounds like a great product. Can you help our listeners understand exactly how your business model works? Do you sell individuals? Do you, because it sounds like individuals reap the benefits here?

Leigh Honeywell

So the product itself is definitely pitched to individuals, but we're working on sort of employee benefits model. So we've built out this platform that's focused on sort of personal security advice, but we've always wanted this to be something that we scale up by getting companies to pay for it as something that they provide to their employees. So we tend to sell either to individual teams within an organization, whether it's maybe the trust and safety team or the developer relations team, where there's like a real sort of public interface. So if it's, you know, we're working with a specific team, it'll often be one of those. But in an ideal world, we work with the whole organization, because, you know, it may be your very visible public folks that are experiencing these issues. But sometimes it's, I always pick on poor Bob in accounting who has like a bad breakup and his ex shares his nudes, and it's just this whole like dramatic, traumatic situation. And what does Bob do? Well, does he go to the EAP, and the EAP maybe refers him to a counselor who maybe doesn't have like this sort of technical expertise? Maybe he, well, he probably doesn't feel like, we as a security field, we haven't done a great job like helping people feel comfortable asking, hey, like, I'm dealing with this situation, what do I do? Like, there's often not that trust with something like a security team. So, again, within that organization where Bob's maybe not on the front lines, but they have Tall Poppy, he knows that he can go to Tall Poppy and get support in this kind of like edge case of personal security, personal privacy situation where there wouldn't otherwise be resources.

Jon McLachlan

And so it's a B2B play.

Leigh Honeywell

At the end, primarily B2B.

Jon McLachlan

And it's a tool that I could purchase and then use as a service for my internal employees to get support or help through difficult situations. Do you have any cases where it's a B2B play, but instead of selling it as an internal tool, you would sell it to help with an external support of maybe a product the company is releasing? So, like, I don't know, a Facebook, for example, to help them deal with online harassment.

Leigh Honeywell

Oh, interesting. Yeah, we've, like, there's definitely been sort of, I've had at the back of my mind, like, wouldn't it be cool if when you reported some particular kind of malfeasance on one of the social platforms, if one of the recommendations was consider tightening up your security, here's Tall Poppy. I got to convince the platforms that that's a good idea first, but it's definitely like, I would love for that to be like a part of that path with any of the major social platforms. I think the bigger vision, longer-term vision is figuring out what that correct B2C play is. And we're starting to do some research and experiments there, but we don't know exactly what the right sort of go-to-market shift is. And so for now, it's primarily going after that B2B market, particularly the incident response piece. We know that it needs to be a lot more automated, a lot more like chatbot focused. And then the real challenge is, how do you maintain that sort of empathy and connection and supportiveness when it's literally like a robot, right? Like, is that even possible?

Jon McLachlan

I mean, TBD. An empathy bot of some kind. Maybe that will be a new innovation too. You could sell it as a

Leigh Honeywell

Someday, someday. Yep. Yeah. And I think there's, you know, the consumer piece also plays into this question of like, what can we do as a company basically providing like self-defense tools? Like, these are tools to keep your account safe. And where is the line of responsibility where the platforms actually need to make their own platforms safer? Right. And, you know, there's always sort of limits to things that are solved with education versus solved at a structural level. And I don't have all the answers on this stuff. These are just some of the things I've been thinking about.

Jon McLachlan

No, these are important questions, and I'm super happy that someone of your caliber is thinking through them and helping, not just thinking through them, but actually using those answers and your insights to help build a better world and a better future for all of us. When you think about going B2C, I'm sure that you're focused on a positive experience, an approach that puts the human first and empathizes with the concerns. So I don't know, is that a five-year plan or so, maybe?

Leigh Honeywell

Yeah, I mean, I think the, hopefully more like two to three. We tried to distill our design philosophy down to two core things. One is not putting ourselves in the user's security context wherever possible. So we don't currently ask for any third-party permissions to apps. We don't have access to any apps, any sort of third-party content. When we do do that down the road, we design our access in a least privileged way. So thinking about, is there a specific API that gives us security information? Can we just look at metadata rather than looking at content? What are the ways that we can minimize how intrusive any sort of access that we have, versus like, just give me your whole OAuth token, give me, you know, everything in your, like, we don't play that way. The second core principle is we don't want to do the like shadowy hands over keyboard, hoodie, dark, scary hacker thing. We want to be like your smart security friend that you come to for advice, right? That you know, that you trust, who's going to give you the real deal, who's not going to like bullshit you or sell you products that you don't need, but also is going to like point you in the right direction to stay safe. And I think that that sort of aspirational security trusted advisor kind of thing versus the like, oh no, the world is on fire, your passwords have been hacked, like, that is, that's a really core sort of behavioral thing that we're trying for.

Jon McLachlan

I love it. And it makes me feel warm and fuzzy on the inside, even just hearing you talk about it. I do really appreciate taking a shitty situation and spinning it so that something good will come out of it, and see the silver lining in all of it. So. Well, you shared a little bit about your best day there at Tall Poppy. Is there anything that you'd like to share in terms of a worst day that you've had at Tall Poppy?

Leigh Honeywell

I think I said it was both the best and the worst day. It was. It was. I was totally trying to get both of those out.

Jon McLachlan

You nailed it. You did.

Leigh Honeywell

It's that media training coming to good use.

Jon McLachlan

I saw what happened.

Leigh Honeywell

I mean, I think the hardest days are the ones where, frankly, like, we can't fix everything, right? Whether it's, you know, somebody's being harassed online and, you know, the attackers are actually like technically sophisticated, using strong anonymity, and they're just, you know, there actually sometimes isn't anything for us to do at a like technical level. We can still provide sort of moral support and risk, like risk analysis. And there is stuff for us to do. But in terms of the sort of concrete ability to like bring someone back to a sense of safety, we're not all powerful. We don't control the internet. My name's not Jack Dorsey. I can't ban people from Twitter. Not that Jack like personally bans people from Twitter, but you know what I mean.

Jon McLachlan

Right, of course. I mean, there are limits to every system, and this is just one of them sometimes. But nonetheless, it sounds like you do make a positive impact in people's lives and some of the toughest situations that they may be facing.

Leigh Honeywell

Yeah, I think that's where it's really meaningful, is when the shit really hits the fan and we can actually be there for someone and just reduce the burden, reduce the impact.

Jon McLachlan

So do you find, you mentioned being anonymous on the internet, do you find that people are using tools like Tor, the onion router, to hide where they're coming from, or they just use like fake names and it's hard to track them down?

Leigh Honeywell

Oh man, there's just a real spread in terms of the tactics that you see from attackers and what kind of attackers, and there's sort of different classes, you know, in the same way as your malware groups have different signatures. There's whether you're dealing with like an individual who's stalking someone over like a romantic obsession, versus a large group of disaffected fans, versus neo-Nazi or other extremist groups. Like, each of these different types of groups and types of individuals have sort of signature moves, and the level of technical sophistication varies extremely widely, all the way from like doing stuff from their home IP address with no, any sort of obfuscation, and under their real name while logged into Facebook, all the way to anonymous remailers, Tor, you know, the tools that you mentioned, hacked proxies and stuff like that, where there is like actually a degree of technical sophistication where they've gone to great lengths to cover their tracks. I think one of the things that is interesting in assessing the threats to someone is thinking through, like, what do the tactics say about the motivations and the self-belief of the person perpetrating this kind of harassment? Do they know that what they're doing is kind of wrong, and that's why they've gone to like great lengths to cover their tracks, right? Or are they so convinced of their own righteousness that they're like sending death threats from their actual Facebook account? And those are, you know, things that we look at and things that we think about in making threat assessments.

Jon McLachlan

Wow. Do you often work with law enforcement in some situations that involve things like death threats?

Leigh Honeywell

We definitely do when it's to the degree of things like death threats. Typically, we will act in more of an advisory role where we're working with the client and they are reporting directly to law enforcement themselves, and we will often sort of advise on how to be most effective at interacting with law enforcement. You know, we're just a tiny little firm. We're not like fancy. We don't have a big reputation. Law enforcement doesn't know us from a hole in the wall. So we do tend to advise folks to talk directly with law enforcement rather than trying to like proxy through us. But we have a pretty established track record at this point of helping people be more effective at that. Because you go to law enforcement and you say, like, I'm getting death threats on the internet. They're like, oh, well, don't look at the internet. And that's not really helpful. Like, getting it taken seriously requires a degree of documentation, requires like an understanding of which parts of law enforcement are going to be more effective at tracking this stuff down or not. So it's, you know, and it's also further complicated by who feels like they have the ability to actually interact with law enforcement in a safe way, which unfortunately tends to, you know, the folks who face discrimination at the hand of law enforcement are also often the folks that are facing threats online.

Jon McLachlan

So that just reminds me of everything that had happened recently in Belarus. And that's an entire country full of a very tough situation, right? And I would imagine that online censorship and online harassment is a huge part of those campaigns, yes, for lack of a better word.

Leigh Honeywell

Yeah, I mean, you know, what we're seeing in Hong Kong right now, what we're seeing with internet shutdowns in various countries related to elections, like, we're in a fragile time in terms of the intersection of democracy and the internet, whether it's what we saw in the States with disinformation in the last election. I was actually just reading about the Democratic Party in the States, their new disinformation team that's been doing a bunch of work around election misinformation and disinformation, and sort of the subtleties there. And it's definitely not, it's not the focus of our work. It is definitely adjacent to the work that we do, and I think that a lot of the folks in the trenches of disinformation are very much fellow travelers.

Jon McLachlan

Oh, definitely, because I could see how misinformation or disinformation

Leigh Honeywell

It's tied right in with the hacking and the account takeovers and the leaking of emails and all of that stuff.

Jon McLachlan

Yeah, what a mess. Well, okay. And I'm super excited to hear about the B2C long-term vision. But if you look into that future and you look out at your grand success of selling direct to consumers and helping establish a stronger sense of privacy or personal security, what does success for Tall Poppy look like in that future?

Leigh Honeywell

I think the key piece there is really that everyone should have access to affordable expert advice on personal security. You know, it's like relatively easy to go to Best Buy and get, like, piece of your hardware replaced. But that sort of next level step of like, how do you keep this all safe? There's a lot of bad advice out there. Right. And getting that quality expertise that is broadly accessible, whether you're a Windows user or Mac user, iOS or Android, they're just, like, what a consumer has access to. Like, man, there's just so much crap. There's so much crap in terms of what's in the market, whether it's like people selling anti-malware on iOS. Like, your iPhone's not getting hacked. Your iPhone's not getting, what's getting hacked is your iCloud account, because you're reusing your password. Like, you know, pretend I'm holding up an iPhone. Like, it costs like one to three million dollars to hack into this with a one-click exploit, because it's the same bugs that are used for jailbreaks. So nobody's like using, like, hacking into your iPhone as an individual random human, unless you're literally Jeff Bezos. Like, your iPhone's safe. If someone is in a situation where they're like worried about their device being compromised, like, what are the actual vectors that they're not thinking about? And it's typically accounts.

Jon McLachlan

Yeah, it's the stuff that we share up in the cloud, right? It's the things that leave the device.

Leigh Honeywell

You know what they say about the cloud? It's just somebody else's computer.

Jon McLachlan

It's definitely someone else's computer. I'm not sure whose. It depends on your vendor and depends where that stuff goes. And it's even the privacy laws associated with all of that data can get very complex. It's a whole mess for sure. Yep. Well, we should also give a shout out to StartOut.

Leigh Honeywell

Oh my gosh, how have we not talked about StartOut yet? I don't know how we missed this.

Jon McLachlan

StartOut is an amazing community. They have NetworQ, which is an LGBTQ founder network. I know that you were in Growth Lab, right? Tall Poppy was.

Leigh Honeywell

Yep. The StartOut Growth Lab is the world's only LGBTQ-focused startup accelerator. We were in the fourth cohort in spring 2019. And you guys are in

Jon McLachlan

the eighth cohort. The eighth cohort.

Leigh Honeywell

Amazing.

Jon McLachlan

Summer of 2021.

Leigh Honeywell

Summer of 2021. Amazing.

Jon McLachlan

Just getting out of COVID.

Leigh Honeywell

Yeah. Yep. So it's, I mean, it's a wonderful program. It's six months long, so longer than the sort of average accelerator, and it's like a tight-knit group. For us, it was super powerful having that like really tight-knit group that got to experience over like an extended period of time, seeing each other's successes and struggles and learning from each other, working through it. Exactly. Yep.

Jon McLachlan

Well, I've really noticed that the authenticity level in this group is just through the roof. And typically, you know, especially among founders, and I get it, you have to play a role, very oftentimes you have to do a lot of virtue signaling and all this other stuff, and it's just, you know.

Leigh Honeywell

Yeah, I feel like people let the like the hustle mask down a little bit.

Jon McLachlan

They do, right? You get to know each other, but you still work through those tough problems and learn a lot together. So, spectacular program.

Leigh Honeywell

Yeah. Cool.

Jon McLachlan

Leigh, well, thank you so much for joining me. It's been a spectacular show.

Leigh Honeywell

It was fun.

Jon McLachlan

It was very fun. And we'll have to do it again. Maybe in a year or two, when you're realize that B2C play and take over the world with one secure [account].

Leigh Honeywell

Exactly. It's like take over the world or prevent the world from being taken over.

Jon McLachlan

Or enable everyone to take over their own world. Yes, exactly.

Leigh Honeywell

There we go. I like that. I'll buy it. Oh my God, this is important. I love it. I love it. Amazing. Do you want to do a sign off, or you've got, you've probably got like an outro?

Jon McLachlan

I don't. Usually I just end them quite abruptly. No, but I'll just say thank you again. And it was a great pleasure to have you on the show.

Leigh Honeywell

And it was really lovely to get to chat in a little more depth. And thanks a lot for listening.

Jon McLachlan

Thank you.

FAQ

Questions this episode answers

Who is Leigh Honeywell?
Leigh Honeywell founded Tall Poppy in 2018 and was its chief executive until December 2024. Before that she was a technology fellow at the ACLU and worked in security at Slack, Heroku, Microsoft and Symantec. She has been a venture partner at Pioneer Fund since 2019 and, since December 2024, Lead Security Strategist at 1Password.
What is Tall Poppy?
Tall Poppy is a company that protects employees from online harassment, with proactive personal security help to keep harassment from escalating and incident response when someone comes under attack. It went through Y Combinator's Summer 2018 batch and is based in Ottawa.
Why do online harassment cases so often involve hacked accounts?
Because the breaches are commoditized. Attackers take passwords leaked in old breaches, such as the 2012 Dropbox breach Leigh mentions, try them on a target's other accounts and find one with embarrassing or personal content.
What is credential stuffing?
Credential stuffing is trying stolen usernames and passwords, usually from a data breach, on other sites to get into accounts. It's the attack Leigh describes at the start of many harassment cases.
Is personal security part of corporate security?
Leigh's argument is that it should be. The accounts on an employee's devices are what attackers go after, so protecting people's personal accounts protects the company too.
How does Tall Poppy make money?
It sells personal security help to employers as an employee benefit. It often starts with teams that have a public face, such as trust and safety or developer relations, but the ideal customer is the whole company.
Why not leave harassment to the employee assistance program?
An employee assistance program offers counseling and referrals, but the counselor may not have the technical skills, and employees rarely bring personal security problems to the security team. Tall Poppy fills that gap.
What are Tall Poppy's design principles?
Two. First, stay out of the user's security context: no third-party permissions for now, and least privilege when access comes, such as metadata rather than content. Second, be a smart security friend rather than a scary hacker.
What does least privilege mean for a personal security product?
Asking for the smallest access that does the job, such as a specific security API or metadata instead of content, rather than a whole OAuth token. A broad grant would make the helper a target.
What kinds of attackers does Tall Poppy see?
Individuals stalking someone over a romantic obsession, large groups of disaffected fans, and neo-Nazi or other extremist groups. Their technical skill ranges from none to anonymous remailers, Tor and hacked proxies.
What does an attacker's choice of tools reveal?
Motive and self-belief. Someone who goes to great lengths to hide may know it's wrong, while someone sending death threats from their real Facebook account may be convinced of their own righteousness.
How do you get law enforcement to take online threats seriously?
With documentation and by going to the part of law enforcement that can track it down. Tall Poppy advises clients who report directly. Leigh adds that the people who face discrimination from law enforcement are often the ones facing threats online.
Can an iPhone get hacked?
It can, but it's expensive. Leigh put a one-click exploit at one to three million dollars in 2021, which is spent on people like Jeff Bezos. For most people, what gets hacked is the iCloud account, through a reused password.
What is the StartOut Growth Lab?
A six-month accelerator run by StartOut, a nonprofit for LGBTQ+ and allied entrepreneurs, that takes no equity. Tall Poppy was in its fourth cohort in spring 2019.
What happened to Leigh and Tall Poppy after the episode?
Leigh led Tall Poppy until December 2024 and then joined 1Password as Lead Security Strategist. She has advised iVerify since July 2023 and is still a venture partner at Pioneer Fund. The Y Combinator directory lists Tall Poppy as active, with a team of 10 in Ottawa.
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