Dug Song: Values over valuation—reflections on building Duo Security and leading with purpose
Download MP3Welcome to Inside the Network. I'm Sid Trivedi.
Ross Haleliuk:I am Ross Haleliuk.
Mahendra Ramsinghani:And I am Mahendra Ramsinghani. We have spent decades building, investing, and researching cybersecurity companies.
Sid Trivedi:On this podcast, we invite you to join us inside the network where we bring the best founders, operators, and investors building the future of cyber.
Ross Haleliuk:We will talk about the hard parts of the founder journey, launching companies, getting to product market fit, raising capital, and scaling to an exit.
Mahendra Ramsinghani:And, yes, we will also be talking about epic failures.
Sid Trivedi:But, Mahendra, we're here to make the founder journey easier.
Mahendra Ramsinghani:That is correct, Sid. But we cannot make
Ross Haleliuk:it too much easier because startups are hard, And, of course, you already knew that. Alright, you two. Enough. Let's get started with this week's episode.
Mahendra Ramsinghani:Our guest today is Dug Song. Dug is best known as the cofounder and former CEO of Duo Security, a company that transformed the way organizations approach security by making it simple, effective, and accessible. Under Dug's leadership, Duo grew from a small startup in Ann Arbor, Michigan to a global powerhouse with over 50,000 customers. The company was acquired by Cisco in eight years for over $2,000,000,000. And here's the best part.
Mahendra Ramsinghani:Duo is probably the only cybersecurity company that consumed less than $20,000,000 to reach a unicorn status. In a day and age when the focus is on valuations and hype, Dug's focus continues to be on values and serving the customer. He is actually the only unicorn CEO we know who is embarrassed by that term unicorn. Dug Zimpak goes well beyond business success. A self proclaimed software communist and a lifelong hacker, he has spent his career challenging the status quo, be it in security, company culture, or styles of leadership.
Mahendra Ramsinghani:From his early working days on OpenBSD and OpenSSH to founding Arbor Networks and now shaping the next wave of innovation and entrepreneurs, Dug's philosophy has always been clear, or shall we say Dug's dynasty, the Song dynasty has always been clear. Put people first, solve real problems, and challenge the entire industry to do better. In today's conversation, we'll explore his journey from a gritty childhood in Baltimore spent hacking to his approach of building a business, why he believes security can be better than a used car lemon market, and above all, how to build a culture that matters. Get ready for an insightful, no nonsense conversation with one of the cybersecurity's most original thinkers. Let us dive in.
Sid Trivedi:Hi, Dug. Welcome to Inside the Network.
Dug Song:Hey, Sid. Hey, Mahendra. Hey, Ross.
Sid Trivedi:Let's get started with your early life way before Duo, and let's talk about you as a kid. You started using computers when you were around eight years old doing data entry for your father's liquor store. I believe that was in West Baltimore. You grew up as a Korean immigrant and, you know, somebody who was working right from the the early days. What lessons did you learn during those early days that later shaped your mindset as an entrepreneur?
Dug Song:Yeah. Well, I guess part of that was realizing how difficult entrepreneurship was. My dad, again, had had two liquor stores. So the first was in West Baltimore, the second later was in Jessup, Maryland, about a mile from the state penitentiary. And in both cases, these were not the best places you'd wanna set that up.
Dug Song:And so so for a long time, I probably had a somewhat negative impression, actually, of of building businesses and of of all that. Although, I was proud proud of what my dad did as I thought it was cool to go with him to the store. I thought it was not so cool that I worked for so long for him for no money, but, you know, that was the the price of having roof over my head. But, yeah, I mean, I I saw my dad build it from nothing. And and maybe more importantly, build it in community with folks that, you know, for me, formative in my life in a different way.
Dug Song:Many folks later in my career helped me with, you know, access to opportunity and so forth. But in my dad's store, I saw a lot of people who had basically none. And my my dad had hired some homeless teens who lived in the motel next door. He also hired a a returned citizen from the the penitentiary who lived in a abandoned milk truck in our parking lot. And so I I saw pretty early how business could actually be a positive force for good in creating kind of opportunity for folks.
Dug Song:And, anyway, it has has some bearing on on how I thought about building the company later, but my company later. But those early days, sort of seeing my dad kind of make something from nothing and and and bring a lot of people with him along the way was sort of the biggest impression left of me that, you know, business could be a positive force, right, in society.
Sid Trivedi:And was it your father who got you into to data entry and tech and computers in those early days, or was it just yourself? You said, hey. Like, computers are a useful thing in this case?
Dug Song:No. No. No. Eight years old in the eighties. I've no impression of of computing outside of what my father had brought home, but he was a he was a gadget freak.
Dug Song:And so you you name kinda any piece of consumer technology. We had probably the earliest version of it, the v one of everything, of a of a bread maker, first CD ROM sorry, CD player, and early, you know, PC, XT, AT sort of days running a liquor store off of software that I don't know where he found. It's called Retail Mate, but it was one of the first piece of software, I think, for for retail that I'd ever heard of. But, yeah, it was it was it was my access to a lot more opportunity online pre Internet with BBSs and all that kind of things. So so I'm I'm very glad that he was a gadget freak, you know, that that definitely rubbed off on me.
Ross Haleliuk:Dug, while at the University of Michigan, you joined the hacker collective VooVoo alongside the future tech leaders like WhatsApp's Yan Koom and Napster's Sean Fanning. Can you share a story of how the group's culture impacted the way you would eventually build companies?
Dug Song:Yeah. Yeah. I mean, you know, the group was never intended to build companies. You know, we were just a bunch of misfits on a misfit island working on, you know, computer security really as a hobby, and and each of us coming for a different place. Right?
Dug Song:We they led us there. Some of us coming more from the kind of, you know, legacy sort of BBS kind of world. Others of us I think Matt Conover, who was the founder of Boohoo, was I think it was 14 years old, 14 year old Mormon kid in Salt Lake City. And we never knew any of this until we met at the first DEFCON event that we all went to, and we were shocked sort of seeing what each other looked like and, you know, learning more about each other's backgrounds. But it really was sort of motley crew of a bunch of folks who were just just hacking for the fun of it.
Dug Song:And the Wu ethos that I think was really, I think, really critical, right, to to all of our kind of collect success collective success was that it was it was sort of a band of brothers trying to work together on interesting projects, learning from each other, building it's like you know, I grew up skateboarding and doing graffiti, punk rock, and hacking. These were, like, you know, my teenage hobbies were all sort of transgression, I guess, in some way or another. But what's unique kind of about all of them is that they're they're gift cultures. You know? They sort of really build upon kind of the contributions of their members, people pushing past and on top of kind of what anyone else has ever done.
Dug Song:And so so, yeah, we validate each other for the inspiration that we had, right, for each other in in creating new technology. And a lot of those projects were things that we ended up working together on. Like like, Napster was a was a project, right, that Sean Fanning was working on because he he didn't have access to all the music, you know, that he wanted. And so at a time where many of us were burning and trading kind of, you know, CDRs, all this kind of stuff, sharing music, pirate music that way. Nabs represent a way to do that online that we just thought would be cool for us and turned out to be, well, very disruptive, right, to the music industry at large.
Dug Song:And so, anyway, so the other thing that I think Wu also did from a culture ethos perspective was everyone had really big ideas. You know, we were all just working on on projects that ultimately just scratched our own niches, but turns out there are many, many more people that had similar issues or concerns that led to kind of big opportunities from these these things that we created. So so, yeah, there was there was a just a a basic belief in our ability to use technology to solve these kind of interesting problems, and, again, a a very supportive culture ethos of us all learning together how to do that.
Ross Haleliuk:It is interesting because the hacker collective culture has essentially created and shaped what we know today as the cybersecurity industry. But then if we look at the present day, there is no like, there is no longer that culture. So what replaced it?
Dug Song:Yeah.
Ross Haleliuk:What is the new incarnation of the of the hacker collective?
Dug Song:You know, I don't I don't I don't like to think that that's really true. I think that there are probably still folks out there that are kind of building things. Well, here's what I'll say. I think there's still very strong hacker culture at large writ large in the open source community. Right?
Dug Song:We're open source. You know? I'm here in Ann Arbor, which is an old hippie town, you know, the birthplace of the pseudo anti war movement and birthplace of punk rock, know, icky pop, and all these bands and stuff. And I sort of feel like open source folks are, like, software communists or software hippies. Right?
Dug Song:Like, you know, sort of have still carry that kind of belief and ethos and kind of working together, right, on on on on a shared sort of comments. And I I think that does exist in some way. It's just that when money came into the security community in the way of a security industry being born, right, of our efforts, it made people somewhat less less interested to share or that some of this went into much smaller sort of groups and forums in which that sharing was sharing was happening in a different way. So I I know that there are still groups out there kind of, you know, working on projects and doing things together, but but it is weird. I still hang out with a there's a private group I have of a bunch of us old hackers from that era of WooWoo and Teso and ADM and all these kind of elite hacker groups or whatever, mostly European.
Dug Song:And it's it is interesting. You know, a lot of Zulu meant, like, I don't even know where this stuff happens anymore, but it does. You know? I mean, in places like China or, you know, places like Iceland or there's always gonna be kids with technology who are doing things, but if they're not supposed to. So
Sid Trivedi:One more question on W00tW00t, Dug. Did you and the did did you and the the rest of the hacker collective know that you would go on and do these amazing things? I mean, it's just pretty incredible to see that the quality of companies that have come out of a relatively small hacker collective.
Dug Song:No. I don't think no. Safe to say none of us had inclination that, you know, we we we've kinda build, you know, successful businesses, right, from what we were doing. I mean, some cases, you know, we had interest. You know?
Dug Song:Certainly, was a tech scene happening, and there was, you know, the rise of the Internet bubble and all those kind of things. But most of us felt like, in some respects, we had missed some of that. You know? And so we were just screwing around with stuff, exploring things for for the sake of sort of a better understanding how this stuff works. We're finding ways to sort of, you know, if not one up each other, you know, sort of beat those systems.
Dug Song:You know? And so, you know, a lot of I think what leads particularly young adolescent men to this sort of space is, you know, it it's a it's a little bit of bravado. It's a little bit of male ego sort of looking to take on these sort of challenges, and and and there's a whole socialization around sort of hack the hacker community that's it's also pretty toxic as actually as a result of that. But I do think the the positive angles on that are that people figure out how to sort of it is adversarial. Right?
Dug Song:You sort of beat each other at these things. And I'm not a team sports guy in any respect, but I do think that hacking is one of those things that comes close. Right? Because you sort of work as a group to kinda figure out how to go after something, a piece of software, a group, another group, another institution, organization. And and, again, there's a there's a real sense of accomplishment.
Dug Song:Right? And when and when you've accomplished those goals you're after, right, going after it. So but, yeah, I I I think that kind of ethos applied to tech means that you'll have founders who will be successful almost no matter what. You know you know, Israel is a classic example, right, where, you know, you have all these young 20 in Unit 8200, and, you know, they they're given sort of the budget if not the budget, at least the the the scope of responsibility of, like, an NSA and all this. And so they're they're driven by mission.
Dug Song:They're given all the resources. They have a bunch of training and a short amount of time, which is to go and accomplish some pretty outsized goals, ton of responsibility, It sets a purpose. And so what do they do after, you know, a couple years and they're they no longer sort of have to do that as part of the military? Well, they go into companies. And so, you know, so, you know, for me, sort of the that that Israeli program is is, like, a natural kind of breeding ground for the kind of entrepreneurial mindset and problem solving and, you know, hacker ethos, right, that leads to all these kind of which is why we've seen so much success out of that that market.
Dug Song:So
Mahendra Ramsinghani:You know, Dug, continuing on that cultural national ethos of when you look at Israel and 8200, you once gave a keynote titled Bad Koreans Do Good. Now, you know, there is, of course, expectations of certain stereotypes. You talked about the male ego. You talked about toxicity. You talked about how the collective cybersecurity world looks at Israeli founders.
Mahendra Ramsinghani:Talk to us about the the Koreans. You know? There is not much that has been celebrated about Koreans. You're clearly a leader in the community. And tell us about the culture.
Mahendra Ramsinghani:What were some positives? What were some pressures on you growing up in a Korean family?
Dug Song:Yeah. Well, I think, you know, East Asian, South Asian, actually, most immigrant cultures, you know, especially, you know, for for transplants here at The US. You know, it's it's after you're a doctor, lawyer, engineer. Right? Sort of, you know, you take your pick, but you you have three choices.
Dug Song:And, you know, that wasn't necessarily that different for me, you know, the sort of set of high expectations. But but to be frank, you know, my both my parents were busy working. So I was a latchkey kid. Like, many kids were in the eighties. I didn't see my parents typical until 9PM when they came home from work.
Dug Song:And so from the 3PM when I came back from school and then fed myself and my sister some cans of Denny Moore beef stew and or ho Hormel chili out of some some cans and microwave. You know, I was kind of on my own. And so so, you know, the expectations for me were just get the grades, do well in school, learn to learn, and then the rest will be okay. I think it's true for a lot of immigrant families. Right?
Dug Song:There's a the heavy focus on education and and academic achievement leading to, again, sort of a natural sort of arc to success in some way. In my case, you know, it I'm gonna say it came naturally, but I was I was fortunate that, you know, the the the grades were pretty straightforward for me to to get. And the rest of the time, I could go screw around and, you know, skateboard, spend all my time in the streets or online hacking or, you know, getting into other trouble. And it was fortunate that, again, my my my parents were unlike many other sort of Korean American parents in that they were they were very flexible in terms of what they saw me do and success. I also lost my father when I was 18.
Dug Song:So, you know, he was, you know, carjacked, stabbed 11 times, all this, and I you know, occupational hazard in in kind of running liquor stores, right, in in bad places. And so from from college onward, I basically had to kind of make it work on my own. So I worked three jobs and kind of do all this stuff, and and so I I think my mom was just happy that I was productive and not not getting into too much trouble. I did have some bit of issue as a freshman. I got some I got caught hacking at the university, but, you know, that's how I ended up with a job working for university for four years doing security and protecting them from people like me.
Dug Song:And I was very proud of the fact that I I could end up paying for my my tuition and extra my my sisters later through school with it. And so so I don't know. I mean, I think, you know, people often think of particularly East Asians and South Asians, right, as kind of model minorities, all this kind of thing, but forgetting that, actually, some of these communities have the widest disparity in terms of, you know, income and wealth and and all this. And so so I say, like, there's good Koreans or there's so called bad Koreans, quote, unquote. I just mean to say, like, you know, I was sort of the kind of Korean in group in a in a liquor store.
Dug Song:You know, sort of different sort of family or home life. And and so, again, you know, I think bad Koreans can
Mahendra Ramsinghani:do pretty can do good too. So And then, Dug, what advice would you have for or how do you see the next generation where there is this constant internal debate amongst the immigrant community? We grew up with a certain set of values, but then here is America, which is all about entrepreneurship, all about breaking tradition, all about forging a new path. But how do you align those two when you look at the next generation?
Dug Song:What advice would you have for the next generation of Koreans? Yeah. Well, you know, it's just where I I mean, the the South Asian community has sort of demonstrated. I mean, again, look at Silicon Valley, look at, like, Thai, and look at, you know, look at all the the CEOs now of all companies. Right?
Dug Song:And how how much success there has been, right, from the DESI community in this. And you see how sometimes that traditional focus on things like education can be an amazing grounding for the kind of uniquely American kind of ambition to go and and create companies, to break with tradition, to start things, and not just be great at executing. We're getting have getting things done, but in in innovating. Right? Solving problems that we don't fully understand often by doing things we've never done before.
Dug Song:And so that sort of risk taking ambition, right, which is I think a I'm a I'm a say it's uniquely American, but I think that is the American dream. Like, people come to this country, right, wanting to go and and forge their own path and create success and all that kind of thing. And if you pair that up with, again, the kind of just, you know, cultural sort of focus and discipline on on education and the, you know, value and hard work and and all this kind of thing, you know, it's just think it's unstoppable. And, you know, there's a there's a bit of advice I do give, Asian dad advice, Not me, but actually, I I I reference Jack Ma, you know, the former CEO of Alibaba, on on what an entrepreneurial career actually looks like. I tell kids, like, it's not it's not what you think.
Dug Song:You know? You you you go to Silicon Valley, and it's like, oh, you should be, like, Steve Jobs or Bill Gates or no. Any of these folks that have, you know, dropped out of Mark Zuckerberg, gonna drop out of college, you know, go start a company. And what you see kids doing when they do that is, like, you have a hundred and one sort of bar crawl apps right, looking for the the closest, like, bar special or something. This is not this is not a real problem or a real business.
Dug Song:And so Jack's rubric on this is quite different. He says, like, in your teens, learn to learn. Right? Very Asian, stereotypically. In your in your twenties, follow a good leader, not a good company, because you always have the opportunity to go do a good company.
Dug Song:Right? Why park yourself at a Microsoft or a Google or whatever if, you know, you can go and if you want to be an entrepreneur, go follow a good entrepreneur. Right? See how they move. See how they execute with all all the resources needed.
Dug Song:See how they recruit people into that program, right, that are well beyond kind of anything that they they deserve to be, anyone they deserve to be hiring at the stage of their business, because there's a magic to that, right, to assembling kind of that and and and what that kind of entrepreneurial leadership and the risk taking and decision making look like. And it's not even really risk taking. It's about how you abate risk, right, which is what those those folks do really remarkably. And then in your thirties, figure out what you're good at. You know?
Dug Song:Find find the industry or path or figuring out what your highest contribution is. And then your forties, then you start. And that's that's very different than, I think, the American sort of model of, at least, tech entrepreneurship. We're like, oh, drop out of school, you know, raise a bunch of money. And but it actually tracks, right, with the results we see, where we know that, you know, entrepreneurs who have had more professional experience and seem you know, figured out what problems are worth solving the world and kinda how they're best suited to do it actually are much more effective in building really significant companies.
Dug Song:And then the continuation of that is is, you know, in your fifties, then you then you just return to better young people. Right? So now you're you could be that good leader. Other people follow. And then your sixties, you should be drinking a daiquiri on the beach.
Dug Song:And so, you know, I I really like that rubric, which is my Asian dad sort of model for entrepreneurship. But, again, I think I don't take credit for it. It's Jack Ma who is much more smart much smarter than I am.
Sid Trivedi:Well, talking about your twenties and thirties, let's talk about that early career that that you had. And, you you know, you spent seven years at a company called Arbor Networks. You started off as a founding engineer. You built a whole bunch of security tools. D SNIF is one of them that's well documented.
Sid Trivedi:You can easily search it on Wikipedia and and learn about, you know, the password sniffing capability that you provided. When you look back at those, you know, early kind of formation years in your career, was there a pivotal learning moment or something you and and this could be a positive learning moment. It could also be a failure that you that you experienced that helped you and shaped you as a leader and as an innovator?
Dug Song:Yeah. Well, from innovation perspective, I think the other thing I realized quickly is that in many cases, security, the emperor has no clothes. Right? Like, as a as a security person, you know, your your sort of job as a professional paranoia is to dispel dispel all these myths about, like, this this piece of software is really secure or this these systems are viable. Like, a teenager, right, with a little bit of time on their hands and and Internet access can actually really do a lot of damage.
Dug Song:They can kinda figure all this stuff out. And so so, yeah, I mean, a lot of my activities early in my career, if you will, was was simply just breaking other people's software. And being on the offensive side of of security and technology, you realize really quickly that, actually, a lot of these companies and a lot of these products are not you know, they're not anything that you can do. I remember when we broke Checkpoint firewall one. You know, we found, like, nine ways through this thing and, you reverse engineered all their authentication protocols, their their VPN protocols, and, you know, it led folks like Marcus Random to contemplate whether some of the things we found were actually Massad backdoors, right, in in these systems because they were, like, zero knowledge sort of exploits against their authentication protocols and so forth.
Dug Song:And we printed this all at Black Hat. It was interesting to me to see the response, and I remember talking to Nir Zuk about this years later who had built all this and because he had to go and rewrite Checkpoint firewall. It's with Checkpoint NG. NG was a result of us basically destroying his his first product. Right?
Dug Song:And so and, you know, the thing you kinda realize as a young, somewhat brash attacker or, you know, security researcher is that, actually, you know, there's there's, you know, there's so many more problems still to be solved, and, actually, some of these solutions actually create their own problems. And so for me, you know, it's just kind of this realization that, wait a second. You know, it's sort of like I don't say the empire is all closed, but, you know, in in some cases, you know, security products are some of the most dangerous because they have so much access. Right? And they and they they sit in very important positions of privilege and management and control that, again, they're they're huge targets, right, for attackers to go after.
Dug Song:We know this now, right, seeing kind of all this this happened, but back then, you know, it was sort of assumed that, no. These these systems, these firewalls, and all these, you know, are are sort of inviolable. But and so for me, it created this perspective that there's there's real opportunity to go after still in security that you could build where you even as, like, a small new startup. And so, anyway, the the other side of that was from pretty from Arbor, you know, two other things. One was kind of we we built that company to create kind of a whole new category of infrastructure security for the global carriers, a time where, you know you know, a single teenage attacker like Mafia Boy in Canada could command thousands of machines to go point at a, I don't know, a bank and hold them hostage, and nothing no one could do anything about it.
Dug Song:You know? Sort of realized that, wow, there's a fundamental issue in terms of security on the Internet that is still unsolved. And so we we worked really hard to create, you know, these kind of systems as as global solutions from the from the jump, and we're pretty successful in doing so. Just the timing was quite difficult as the market had imploded trying to sell to global carriers when they were putting their execs in jail during the telecom nuclear winter in the early two thousands that followed the first Internet bubble being burst, taught me really quickly about the the need to be sort of nimble in business. And so so a couple things.
Dug Song:One, you know, Arbor was a good experience, but a difficult one in some ways because we built what I thought was an amazing culture and team. You know? Every company since since Arbor, have had a group chat like IRC just like we did in any of our hacking groups, not the center of it, until, you know, Slack or HipChat first, and then your Slack came and created the the real opportunity in that market. But but we had a very online, very open source, very hacker sort of culture, right, to all this that I've learned was was really fundamental to building great products. The parts of that really got away from us, you know, by the time we were on third CEO, fourth head of sales.
Dug Song:You can really lose the soul of the business sometimes that way. And so, again, one of the things I I I learned sort of deeply from an experience that was difficult for me at Arbor was how important culture and leadership really are. Because in in a technology company, you have nothing else. You don't have factories or machines or land or, you know, all you have are people. And if you cannot lead those people well with integrity, with vision, with purpose, with care, with with inspiration, you really can't accomplish more, right, together than than you could apart.
Dug Song:And so you the balcony of of really organizational sort of leadership is something that I I I came to really respect and value deeply when when it came time to start something my own company later.
Ross Haleliuk:After spending years in cybersecurity, you took a fairly unusual detour joining a peer to peer TV startup around the time when YouTube also launched. Could you talk more towards how did stepping outside of security broaden your perspective as a technologist, and, also, which of the new ideas and perspectives did you later bring back into security? Thanks, Ross. This is an important one because I, you know, I think I used
Dug Song:to joke with this about I used to joke with a friend, Tom Tajik, who's a very well known security hacker, researcher, and, you know, erstwhile founder, about how all of us who are secure serious about security, care about it deeply or kinda grew up in it, all have to leave. Because at some point, you realize how how bad the industry is. It's sort of like, you know, crunch all you want. You know, they'll someone else will always make more. You know, it's an adversarial thing, so your your software doesn't go out of style or is obsoleted by it is broken, right, frankly, by by attackers or bypassed or all these kind of things.
Dug Song:And so so it's not a matter of just getting ahead, but to stay ahead, right, in security in a way that that is there's a real cost, right, of of innovation. And but but also because of that, customers are accustomed to buying things that they don't really need. And and, you know, we we're not mature as a market, as an industry, in security engineering the way that, for instance, like like NASA or even, you know, you know, here on on Earth, you know, our our terrestrial sort of transportation safety boards are. Right? Like, a a plane falls to the sky only the same way maybe once or maybe twice because that's why everyone has black boxes.
Dug Song:That's why, you know, there's an, you know, TSP that looks at the root cause analysis and does all this, and we sort of stop kind of things from happening. But but in security, it's like, wow. Even the same organization sometimes are breached multiple times the same way. So, you know, it's like Groundhog Day in in the worst way, oh, in Oregon, where things were not burning, were not getting better, and there's this hamster wheel of pain, right, that companies are on. And so I do think sometimes, you know, because of that, security can be a lemon market, meaning it's like a used car market.
Dug Song:People buy something. They don't know if it's any good or not until they've after they've driven it off the lot, then it breaks down. They're like, oh, crap. I didn't realize this was no good. But by that time, you know, there's a company that's already made money, and they weren't and so I think there's a there's a fundamental problem in security that way that for a lot of a lot of security people, right, people who actually grew up in this or really care about it deeply in this way and identify with it, sometimes take a really cynical view of which is, you know, wow.
Dug Song:The industry is is is snake oil or bad and blah blah blah. And, you know, there's definitely some some element of that truth to that, and that's why I left. You know, I left security in a go to inner TV because I felt it was more honest living, and I felt like I was tired of trying to convince anybody that these things are real problems or trying to compete against, you know, competitors who had were selling a bunch of air. Right? Like, you buy a box, put it in the network, nothing's hap nothing happens, and the vendor see says, see?
Dug Song:You're more secure. Nothing's happening. And I just was growing tired of that kind of, you know, lack of value proposition and and and challenge, right, in in the market. And so, anyway, we built this inner TV company. It was our it was basically, like, atoning for my sins with Napster.
Dug Song:You know, it was live streaming peer to peer TV, very hard, difficult technical problem to solve, and one that we partner, right, with, you know, the traditional kind of industry players to go and extend the reach, right, of terrestrial broadcast or satellite to to Internet viewers and so forth. But, anyway, you know, it was it struggled for other reasons. It's doing fine now, but, well, it turns out that, basically, you don't need peer to peer. It doesn't matter to having a theoretically perfect distribution of video over application that are multicast, you know, where one person one household gets the stream for the World Cup and shares with everyone else, right, on their subnet. Doesn't matter.
Dug Song:Right? Unicast streams, polluting the backbone, all this stuff are just fine when it turns out it's it's all a big game theoretic model anyway of eyeball providers dumping kind of the ports to the content providers in settlement free sort of ping agreements at the major Internet exchanges, and no one's paying for anything. Right? So, like, it turns out that's just fine. And so there's there's other ways that the world really works that kinda, you know, meant that our approach wasn't needed.
Dug Song:But the lessons I learned other than technical around that were that you can build a business through word-of-mouth. Right? Like, Zattoo is a company that spent almost nothing on marketing and did almost everything to engineer a viral acquisition model, right, where we we did track kind of the viral k coefficient of of invites per user to any other user. We figured out how to drive engagement right on the platform. We figured out how to, again, scale these these audiences, right, with with offers and and things that we could test in real time, right, and not not have to take out a billboard ad and then see what happened the next month.
Dug Song:Right? And so so there was a there was a consumer kind of marketing angle, frankly, that I picked up from Zattu that we did apply to some of what we did at Duo to make security something that was much more accessible, widen the market for but, yeah, it all came
Mahendra Ramsinghani:from doing Internet TV. So, Dug, as you look at your career arc, you know, Ann Arbor or maybe going back to, you know, West Baltimore, Ann Arbor, then Zurich I mean, from Zurich, you could have moved to literally any part of the world, you know, London, Silicon Valley, which is like this crucible or a magnet for people such as yourselves. But you've been extremely loyal to your roots in Ann Arbor. You know, I my one of my most vivid memories of you in Ann Arbor is, like, you know, there's a cafe outside Zinger Bend, Sweetwater, where I was sitting, and I hear this loud noise, and it literally jolts me. And I see the noise with the your skateboard hitting that brick, you know, paved path outside Zingerman's, and I see Dug's song like skateboarding pie.
Mahendra Ramsinghani:So, I mean, you've been very loyal to the community in Ann Arbor. In fact, I remember that you also created a community at at a brewery, a local brewery. You you'd repurpose that for a entrepreneurial community. Tell us about this notion of geography, entrepreneurship. What draws people like you to certain geographies?
Dug Song:Yeah. Well, you know, I I I happen to I didn't ever have an intention to be in Michigan. I was in Maryland when I was applying for college. I applied mostly to small liberal arts colleges in New England, thinking I was gonna go major in philosophy at a small liberal arts school, and I happened to apply to Michigan because I had a friend who went a year ahead of me and wrote back saying how great it was and how the application was so cheap. So that was it.
Dug Song:You know? It was a cheap application, and I I did it because my friend said, hey. It's a good it's a good fallback option or something. Turned out, it was the best decision I ever made. I I only realized this after I went to go visit some of these schools in New England, Williams and so forth, and realized, wow.
Dug Song:It's just a bunch of just a bunch of white kids drinking in the woods. Like, that's like not that's just like not not for me. And so I went to Michigan in part also because, you know, I'll just say, I I explored the network from afar when I was still in high school, and I'd never seen a place with the kind of network for students with the number of commercial unises, as well as a what they call a center for it was a supercomputing center, but they call it center for parallel computing, the craze, and all these systems that I had not seen anywhere except NASA Ames. And won't really talk about that right right now either, but, basically, you know, I was amazed that a public research university would have all these kind of resources for its students. And so that's one of the reasons I went.
Dug Song:That's the best decision I ever made. It was it was great. The the difficult to hear me was that Ann Arbor is such a small town, and I was used to, you know, hanging out in cities. But, you know, it was it was it's a amazing undergraduate experience, great place. And and what I came to appreciate was every place is about something.
Dug Song:Right? Like and then Paul Graham once said something like this, like, you know, New York is about money, and LA is about fame. Right? And and when I was growing up, you know, being in the shadow of DC, you know, DC was about power. You know, San Francisco was about disruption, right, whatever that was.
Dug Song:But a place like Ann Arbor, you know, Ann Arbor was naturally about ideas. It's a sort of deep rooted place. Like, it didn't matter how much money you had. Didn't matter what like, it was all about ideas and what crazy ideas you had, and this goes all the way back, right, to the hippie movement and the student movement and, you know, all these kinds of things. There's a culture here, right, to kinda round this.
Dug Song:It's very, very deep. And so I love that. I love the fact that I could be inspired. Like, the Conor O'Neill's, you know, local Irish pub trivia night, you know, hearing all these amazing people sort of killing it. Because, like, oh, man.
Dug Song:That person seems sounds like a world expert on, I don't know, Parkinson's disease or, like, whatever nerve neurodegenerative disease because they are. You know? They're actually actually the world after they're in a bunch of books or or even other people, like, I'm a theory of revolution or I love being a place where there are people where it's about those kind of ideas, and it wasn't just tech. And so though I love tech, I sort of feel like tech is just sort of an approach or a skill set, a tool in your toolkit to apply to all kinds of interesting problems, but there's so the world is a much wider place and so amorous. I I kind of fell in love with the community of of people and ideas and idealists here.
Dug Song:The other thing I I'd say also is that and I grew up in, you know, in Baltimore and DC in a community of, like, skateboarders and punk rock and all that kind of stuff. And I'll just say, you know, like, my first concert music show was a a very important band to me now. Well, you know, then too called called Fugazi, which was I kinda imprinted on, and this is a punk rock band that was very much about community. And every show had nonprofits and would donate money to, you know, all this kind of stuff. But I I think punk rock in general is sort of contrarian and very much about community.
Dug Song:And and for me, a large part of that mindset you know, if there's, like, a security mindset, which we understand, like, punk mindset is sort of resisting this pressure to conform but without being just contrarian, which is its own kind of conformity. Right? And so I feel like, you know, from that experience in kind of punk and growing up, I I learned how to sort of rebel meaningfully. I just sort of stand for something with integrity. And and here in Ann Arbor, you know, with all these kind of big thinkers and stuff, I sort of feel like I learned a lesson that, you know, the world is really resistant to change and progress.
Dug Song:And so it's like purpose and meaning and impact requires sort of deep intention and actually sometimes subversion. And from hacking, like, we're pretty good at that. So and so I I just feel like I'm in the right place. I feel like this is my home. This is my people.
Dug Song:This is the community that I care about, and it's the community that helped me build my company. And so, yeah, I feel I feel like place matters, and my ambition is to be a good neighbor, be a contributing member of my community. And, also, it's fun. It's fun being a part of a place where you know people, see them kind of build alongside or with you for many years, and where you're rooting for them just as much as they're rooting for you.
Mahendra Ramsinghani:And so And, you know, it makes complete sense, Dug. One sort of observation that I remember having in Ann Arbor, which I kind of sorely miss in San Francisco, is that you could walk down and bump into somebody who was working on nanotechnology. You could walk down and bump into somebody who was working on biotech, cancer research. All this confluence of different brilliant minds in a very small place was so amazing. And the valley, look, it is a sort of somewhat of a monoculture in its own way.
Mahendra Ramsinghani:There are now changes occurring, but I I see why you you speak of Ann Arbor as a place of ideas. Talking
Sid Trivedi:about Ann Arbor being a place of ideas, Dug, you and John Oberheide, your cofounder duo, came up with a little idea that ended up becoming a pretty big company. You've talked about the early days in the past and other conversations, and and you've said that neither of you had any intention of building a company when you got started, you know, tinkering on the idea for what ended up becoming Duo Security. Could you talk a little bit about those early days, and how did you switch from that how did that mindset shift happen from, you know, tinkering to actually building a business?
Dug Song:Yeah. Good question. I I think for a lot of technical founders, and I consider myself one, though I was CEO of Duo, I was you know, I mean, I grew up hacking, and, you know, my my role had always been at that when all these other companies although at Zattu, the inner TV company, I was actually managing engineering. Was VP engineering, not a cofounder, where I kinda learned some management rope kinda learned the management ropes in someone else's business first. But with Duo, you know, the idea for Duo kinda came out of working at Barracuda Networks.
Dug Song:You know, Barracuda was a company and and I don't know if you had similar journeys yourselves or see this with other founders, but I tell people all the time, there's a time to earn. There's a time to learn. I think Mark Sester had something like this. But, you know, my my point of view on this is there's so many lessons that are better learned on someone else's dime than than your own. And so I've kinda flip flopped my career for kinda starting a business or then joining someone else's or starting you know?
Dug Song:Because, you know, you you can learn a lot, right, from what other people are doing. And Barracuda, man, I I was I wasn't there long, but it was it made an impression in a big way for me because they had opened an Ann Arbor office. The the company was based out of California. The founder had been Michigan alum, Dean Draco. But I'll be honest with you.
Dug Song:I had friends of mine who were making fun of me for going there. They're like, wait a second, Dug. You're building all this, like, super sophisticated anomaly detection behavioral anomaly detection kind of systems in your past in both Anza and in both the at Arbor Networks, right, for wide area as well as for, like, all the big banks and financials. Like, why would you go do open source spam appliance company? Like, what what's that about?
Dug Song:And I didn't have a great answer for them other than I saw them kind of picking up into the market that didn't seem to be well served, right, which are, smaller businesses and folks, you know and and I I felt kind of deeply that I watched as as security had spread beyond kind of the purview of just the banks, hospitals, and governments that had things to protect than to every other target of of chance, not of choice, right, that attackers were going after with these, you know, phishing campaigns and everything else, sort of indiscriminate hacking. And so I left Barracuda after learning that there was a real market opportunity in democratizing security. Right? Because, I mean, Barracuda was amazing in lot of ways. They were building a version of something like Cisco or someone else might have Blue Coat might have at, like, a tenth of the cost.
Dug Song:Right? And with a model that everyone said, oh, you know, you crack the hood on, like, one of their boxes. You're like, wait a second. This is, four year old Intel cell alarm processor. Like, why would anyone run this?
Dug Song:Like, what is this about? And but you realize that they're they were it was kinda wild. And, again, I don't wanna share too much about kind of their their process or method or or speak any way would be interpreted natively, but they were very clever or in terms of how they sourced not only components and assembled kind of their their their platforms. Although, I would say that they had, like, a new Harvard generation every two weeks. Kinda kinda wild.
Dug Song:But even how they source their talent. Right? They were they would pull people out of the gym after seeing them, like, wow. That guy is, like, in here all the time. First in, last out.
Dug Song:Let's put them on the phones and have them sell cybersecurity, like, totally strange, but kind of amazing right now. They were focused on kinda building operational sort of excellence, right, and what they were doing in in ways that were pretty pretty different. But, anyway, long story short, you know, Barracuda was one where I saw the opportunity for for security to be to really be much more mass market. I just thought that we could do without the channel and without the hardware, but I didn't know how or what we would do. All I saw were there were companies that were being hacked that didn't seem to have any options.
Dug Song:You know? Like, who was actually solving for their needs? Are they really gonna go deploy a firewall? Because and my my my first company straight out of college was a security consultancy. You know?
Dug Song:Was for all the big banks in casinos and UN and and and so forth. But the small businesses, they they had no chance, right, at at securing themselves meaningfully. And so so we didn't know. We didn't know what it would be, and we were screwing around with. And, actually, when I when I left Barracuda, because I was there to help, you know, them prepare for what would be their IPO.
Dug Song:And when I left, you know, pre IPO, my wife was six months pregnant with her second child. She's like, what have you been doing? Like, I do not understand this logic. And for me, it was it was more that, no. No.
Dug Song:No. I there's a problem to be solved here. I don't know what it is. All I know is who I wanna serve. Right?
Dug Song:That there's, like I wanna build security from the 99%, not the 1%. Like, attackers are going after everybody, and no one has a focus on kind of how how you solve that. And so I said, I don't I don't know what that is, but, you know, I I just think I can do that in a way that's that different, maybe better than what Vericat had done, but I had no idea what that would be. I just felt compelled to go in and try. And and it was some of these activities.
Dug Song:Like, I remember seeing a small auto body shop here in Michigan get get hacked by an attacker who siphoned 3,000,000 out of them, right, in this in this wire transfer and their bank, Comerica. There's a there's a lawsuit you can look up on this. Comerica Experimental was the the business. You know, the small auto body shop sued their bank who had issued them RSA tokens. And you look at this, and you're like, wait a second.
Dug Song:The bank did everything right. Right? They extended the best security available to them, right, to the small customer, and they still got hacked, and they still have the money. And so who's at fault? And he realized that, wait.
Dug Song:This is, a bad situation all around. And and so anyway so, you know, Jono, I pulled in after I left Barracuda to go start something, but we didn't know what it would be. And I remember tell telling Jon, like, I don't know what we're gonna do, but let's let's let's go have some fun explore. He was in in the second year of his PhD, so he was still a student, and and we just started hacking. I had, like, came up with a bunch of different ideas.
Dug Song:It was kind of a kind of a woo woo style kind of situation. Like, this you know, here's, like, 20 different things we could kinda work on as we did, and we tried kinda it was just fun to hack with him. John was my my student intern at Arbor, and so I knew what he was capable of, and he's, like, a ten year younger version of me. So, yeah, it was it was it was a lot of fun just to hack around. But then we came across, you know, something which was a bunch of these folks we were talking to.
Dug Song:Know, these these customers were like, you know, the biggest problem we have is is account takeover. I mean, they didn't call it that at the time, but there have, you know, people losing their passwords to to phishing attacks and all that kind of thing and then taking over kind of the infrastructure or other business. And so we we figured that we had to go and solve that problem. I didn't really want to go into two factor authentication until, in fact, when we looked at all this and we had in fact, we had actually worked with a reseller that got us access to me more of their customers just to do some customer discovery, do some customer reviews, and figure out kind of what problems we're facing and all this. And it was actually very disappointing to us.
Dug Song:We realized that actually, you know, strong but usable and deployable two factor allocation for this end of the market is something that is a huge opportunity that no one's really addressing. And I was pretty depressed because, know, that's like a thirty five year old industry, you know, security in, like, the eighties and stuff. And so so I didn't wanna do two factor, and neither really did Janu, but but it's end up being what was most impactful and important for the customers that we wanted to serve, and then we just kept going from there. But but, yeah, that was that was kinda what Barracuda was about and leading us into kind of this opportunity.
Ross Haleliuk:What was so unique about Duo is that the company didn't really invent the multifactor authentication. As you mentioned, it was a thirty five year old market. But what it did do, it made it easy to deploy. It made it very easy to manage. It made it very easy to operationalize.
Ross Haleliuk:And it can indeed be said that Duo was the first company in security that has gotten to a multibillion dollar exit not because it invented some kind of a new way of securing infrastructure, but because of the user experience. And what are your thoughts around the importance of of UX in in cybersecurity?
Dug Song:Yeah. No. I think I think it's just it was just overlooked. I I think attackers had already changed their MO. Right?
Dug Song:You know? And I was I was one of them. Right? Like, why did I real build these stuff? Because I realized that actually it's much easier to just tailgate users in Right.
Dug Song:To access to systems and environments than than try to break through firewalls. Although I did that too. And, you know, users have always been through that that that weak link, and access is always king, right, for attackers. Right? If you have access and, you know, to what users can do, you bypass all other security controls, right, where you can simply put on the janitor's uniform and roam the casino freely, right, like a casino heist.
Dug Song:And so, yeah, we we realized quickly that there were kind of three massive defects in terms of how strong authentication was being done. One was not usable. Right? The hardware key, it was the numbers that change every minute, and, you know, all this is just not really anything anyone wants to do. Right?
Dug Song:So you basically just frustrate your users, not the attackers. The second was that, again, there's a tremendous cost, right, to actually deploying this stuff. Right? Putting little tiny computers in the pockets of every employee. It's like, you know, having to not lose them or put them in the wash or, you know, whatever.
Dug Song:It's it's just not tenable. And, of course, integrating that right in the path of every login, right, that you have to protect is just really painful. And then the last is, you know, it just it didn't provide for many buyers, for many customers kind of the cost benefit, right, of what you know, they they needed to protect themselves. They didn't understand how this would actually really stop the problem as a measure measure first or last resort. Right?
Dug Song:Like, you know, at the time, we were sort of so focused on, like, well, prevention detection is so much more important than prevention because the attackers will always get in. I was like, this is this is sort of fatalistic. But this notion of, you know, the attackers will always sort of get in, and you just need to be able to detect them and respond fast enough. I'm like, well, there's a whole class of, you know, business problems, right, in terms of that impact. Like, when I siphon out your money at 04:30PM on a Friday, you know, just past the Fedwire you know, ahead of the Fedwire, you know, limit, and you're not getting that money back.
Dug Song:There's no way to cover it. Like, that is a game over sort of problem, right, for a lot of businesses. And, you know, I think it'll only later that VCs sort of understood this when some of their portfolio companies were the ones kind of, you know, losing money out of, like, a $10,000,000 a round, all being siphoned out by an attacker and no recovery. Now those are things that I think sort of shifted sort of the mindset of investors thinking about this stuff too. But but, no, I think of security engineering and design engineering as being two sides of the same coin.
Dug Song:Right? Not not opposite. Everyone thinks, oh, security and usability. They're opposites, diametrically opposed. Right?
Dug Song:You you can't have one without sort of sacrificing the other. But my point of view is that actually security engineering, design engineering are the same thing. It's how do you make the right things happen by default? And so we just had a a strong focus on how do we make the strongest security the easiest for people to go deploy and use. It turns out, you know, we were at the right place at the right time with the rise of the cloud and the ability to deploy sort of services even to not software applications, but hardware sort of devices, right, via the cloud with a device actually already sitting in everyone's pockets in the form of a cell phone, right, or smartphone, right, with applications that we could deliver.
Dug Song:You know, we could create, you know, traditional sort of Orange Book terminology, a trusted path, right, to that user outside of kind of the main in line sort of band of of access. We had all all the pieces we needed to go and create something that would actually be much better, but also easier to use. And so that was really the focus. And, again, as as as particularly smartphones got better. I didn't for many, many years, I didn't have a smartphone.
Dug Song:I you know, John was all about it, thought because I think the smart I think the iPhone was less than two years old when we started Duo. And I was like, oh, it's a fad. What's that crap? You know? I I love you know?
Dug Song:Like, I remember I never had a BlackBerry, but I always wanted one. I always thought the keyboard was so cool. But, no, I was I was admittedly a pessimist when it came to smartphone adoption. John was like, no. No.
Dug Song:No. This is happening. But I also didn't trust it. You know, part of it was like, I don't I don't think you know, John, like, you you and I know, like, we can hack the hell out of this thing. Like, this is probably not a very safe platform.
Dug Song:We we know we can probably take this thing to the cleaners if we wanted to, but it turns out, you know, that all got better. We had friends at all these places, at Google and at Apple, who built security in instead of waiting it for debolted on. And so for instance, there's no, like, antivirus market for iOS. There never will be and never should be because, you know, they they built in a secure element. Right?
Dug Song:A hardware root of trust, a trusted execution environment, road attestation protocols, secure boot sequence, road attestation protocol. We all these things that is basically, again, the sort of delivery of the dream of the eighties or nineties, right, of the orange book. Right? Trusted computing base, all that stuff. So, you know, it's it's kind of amazing how far we've actually come in security in some ways, but really in the consumer sort of security in the consumer sort of product world, right, not as much the security industry per se, which might be a little bit controversial to say, but you know, that's my story.
Dug Song:I'm sticking to it. So, yeah, so that's that's kind of my perspective. And and, increasingly, I think the future for security is more of that. Right? Security that no one has to see, no one has to deal with because it's just built in versus being bolted on.
Dug Song:And it's integral part, right, of any of the systems that we're using largely because these hyperscaler platforms and, you know, vendors, they own the horizontal and the vertical. Right? The Microsofts, the Apples, the Googles, etcetera.
Mahendra Ramsinghani:You clearly the decisions that you made, Dug, at Duo when it came to user experience and design, the decisions you made that led to solid engineering, that translated into a lot of customers, a lot of economic value. What 50,000 customers, economic value would say two plus billion that that Cisco paid when they acquired Duo. How did you continuing that arc of making decisions between user experience, between engineering, how did you navigate the situation between Cisco versus saying, we could take this company public? So it's it's sort of classic classic diversion of the roads to say, should I turn left? Should I turn right?
Dug Song:Yeah. That's that's a that's a tough one that I haven't really talked very much very very much about. Yeah. It's complicated. I'll put it this way.
Dug Song:I think every CEO and founder and every CEO and every board, you know, have fiduciary responsibility, right, to seek the best outcome for for for a company and its shareholders. And, you know, Duo was one that we're you know, we were one of the best performing SaaS companies of all time. Like, people don't really know a lot of this, but, you know, there's a point every year which Duo was cash flow positive, right, for almost all of our lifetime. I never had to necessarily go out and raise money, and we had a lot of folks come to us typically at the end of the year because I would basically blow them off. I had investors kind of reach out, and I'd say, look.
Dug Song:I'm busy building a company. If you wanted to chat, you know, why don't you come visit us in Ann Arbor at the end of the year in December in Michigan? Very few of them did. The smart ones all did, and they found that, you know, we were a company that we didn't really need a lot. And, you know, ultimately, you know, having raised hundred 19,000,000, I spent 14 of it to get to over a hundred million in ARR and kept going.
Dug Song:And so, you know, we so we were on the path to IPO, and and there were a bunch of things that were pretty remarkable about kinda what that path would have been in that you know, I think only a hundred companies had IPO ed, I think, since twenty two thousand five. I forget what it was. Well, anyway, there's there's whole this whole rubric that, you know, our our lead bankers had for us on on on how special Duo was, and, you know, I guess every banker will make you feel that way. But but here, they had, like, real details and and stats and so forth that were really interesting for us. And so when we did get sort of interest, you know, like Cisco came at us one year, and I was like, nope.
Dug Song:No interest. You know? Sorry. I still had to present to the board, though, that, you know, that that there was that there was interest. And and, of course, you know, I my board was long, the company.
Dug Song:No. No. Keep going. You know? Like, this is a distraction.
Dug Song:Don't worry about it. But but we did end up I ended up making sure that we ran a dual process because I said, look. Know, Ken, if if this is sort of from one, you know, I'll just say that this was not a great offer, but maybe there's gonna be others. And and, you know, there's I I believe I believe at the time we had a fiduciary duty to run down sort of a dual track and make sure that people understood what else was going on out there, our last look, basically, at the private markets before we went to the public. And and so I built out, you know, kind of all the things I needed to for our IPO.
Dug Song:We had our ops meeting, put together the the consortium bankers. We had built a public company board. I was I that's the thing I actually one of the things I missed. Other than my team, I miss the other team I had, which was my board, but I loved my board. I built a really good board with people I really, really respected and really still look up to and and still stay in touch with.
Dug Song:But by the end of day, when Cisco came back to us with a number that represented the largest multiple ever paid for a private software acquisition at the time, you know, I I took a pause for a a bit here with with with Pajano and and and my CFO at the time, who's not going to be my public company CFO. I I wanted him to be, but he was pretty clear he didn't want to be. And so we brought in another CFO, and that was fine. But I, you know, I think we had a difficult decision to make. You know?
Dug Song:Do we, you know, do we do that in the interest of our team and our our, you know, our our shareholders as well as our our investors and and expand this kind of journey with on with with Cisco's platform, or do we just keep going? You know? Why why get off the train now? And at the end of the day, you know, I think, you know, Cisco had a convincing argument that, in fact, you know, a lot of what the business could be on as part of kinda Cisco's broader security business, I think But when we joined, it was, a 2 and a billion article of the security business. By the time we exited, was, like, 5,000,000,000.
Dug Song:Right? By the time I left, right, I missed 5,000,000,000. And Duo was the fastest part of that. Right? Fast growing business within Cisco for many years.
Dug Song:But, you know, these these are hard decisions that come down to really sort of what what founders want to do. And, you know, I'm I'd be full credit to my board. I mean, they didn't beat me up too bad about it because, you know, by and large, they were like, why are you selling now? My son fucking oh, this is crazy. Like, we have and, you know, it's hard not to sort of look back at what could have been.
Dug Song:I try not to. Life is too short for regrets anyway. I don't really have any necessarily about about this, but it is you know, by the math of it, you know, kinda what what the business is doing today is we're like, yeah. Well, you know, that was a interesting decision. But, again, I think we we we did expand kind of that to what was, you know, from the 50,000, you know, customers we had coming into Cisco, but Cisco having many hundreds of thousands of more customers, right, that we go after, you know, meant something meaningful, and especially in ways that, you know, we were we we're still yet to build out.
Dug Song:We had done quite a bit of enterprise. You know, it's half of our business, but, obviously, Cisco had a ton of of really large enterprise customers and and relationships, and and I also had a very global business, right, where our our entire rest of world business was, you know, pretty small, right, like, 15% of what Duo was doing by the time we came in. And so, anyway, in any respects, it it made sense, right, for the continued scale and growth and, you know, trajectory of of Ooduo as a as a business and company. But, again, these are these are hard. And and any founder tells you otherwise, you know, either the company is doing not doing well or there's some other similar circumstances, but these are hard decisions, right, to have your baby, you know, sort of bought into another family.
Dug Song:And when I left, you know, I left, yeah, well, after Jono. I think Jono I left kinda two years after Jono did. I felt basically a central responsibility for, like, eight thousand people, right, that I came into the orbit of in the leadership of in in global security business Cisco versus the 800 people I brought into it. But we made tremendous impact, you know, and not just in terms of our business, but in terms of, you know, Cisco's. And so, you know, that for that, I'm I'm proud, and and hopefully hopefully, you know, g two came later.
Dug Song:Felt and saw this. I mean, contribution. Because, you know, we there there were sort of a SAS cabal we had within Cisco to kinda help build all this and kinda really, you know, help take the business next level. And and, again, it it did scale. Like, it it, like, doubled the global security business, right, in the time that we were there.
Dug Song:So, anyway so, you know, I don't like I said, life is too short for grits. I don't necessarily have any about kinda exiting the business, but you always wonder. Founders will always wonder about, like, what what else could have been? What would the other paths look like?
Sid Trivedi:You know, I remember doing a conversation with you, Mahendra, Chenxi in 2021 on the CyberSeed community. I remember this exact same question, and this was when you were at home sitting at your desk, and you actually pulled out the draft of the SWAT.
Dug Song:Right.
Sid Trivedi:You said, you know, I think about this. I think about this more than you think. It's
Dug Song:just Yeah. Yeah. Well, I I should probably not keep it by my desk. That's. I
Sid Trivedi:was gonna ask you if you still keep it. So clearly, you do.
Dug Song:No. No. It's at that's at home. I you know? Now now we have another office here now.
Dug Song:And then now we've been focusing on other things. We built a family office, built a foundation. We're kinda funding a lot of other people's companies. You know, I'm actually I'm actually not doing as much security investing as you might expect, you know, although I did just make another security investment yesterday. But, you know, I am I'm investing basically in almost everything else these days, like from mushrooms to space, And I haven't had lot of fun doing that, particularly in Michigan where there's a lot of interesting founders and companies tackling global problems, but in ways that are very specific to to what's here.
Dug Song:So
Sid Trivedi:Well, let's get into the final section and just, you know, broader lessons for founders. And, you know, one of your leadership mantras has been to build a learning organization. Could you talk a little bit about what this learning oriented culture is and why it matters for founders?
Dug Song:Yeah. Well, you know, I'll just say I think this was just an artifact of us being in Ann Arbor. Right? We talked about sort of the the culture of of ideas, but but, really, you know, what's Ann Arbor about, actually? The team the team the team, right, the winningest football program in history and national champions as of a little bit ago.
Dug Song:Frankly, a different kind of disruption, which I think is it really comes from sort of learning and doing. So, you know, I I think, you know, teamwork is important, but the ability to actually improve and learn together is actually the most important, right, as as for any team. Right? And and so, you know, like I told my my folks, right, just make sure we keep ourselves sort of at least Midwest humble. We weren't smarter or we didn't work any harder, and we weren't any better looking or anything like any of our competitors.
Dug Song:The the one thing we did better than any of our competitors was to find new routes of success, right, that that we could own. Because, know, just just and just like a college football team, like, we were to steal, like, Ohio State's playbook, there's some people that might argue that we did, but, you know, in some other ways. But us running their plays, why would we more successful than they were? Right? They they they figured out how to do this.
Dug Song:They they own that playbook. We need to build our own. And so in every part of the business, not just in tech or a product, but in sales and marketing and CS, we worked really hard to innovate. Right? Do things that other companies weren't.
Dug Song:In fact, when I hired my entire go to market team for Duo, we were pattern matching for something that we hadn't seen anywhere, which was high velocity, high volume inbound inside sales in a way that I'd only seen anything similar at at Barracuda. Right? But this was even smaller ASPs and even higher velocity deals. And when I looked around, it was my my early board. I was like, well, who else's business is like this?
Dug Song:And we're like, wait a second. Zendesk. Like, Zendesk was the comp, and that's why I hired all these Zendesk people. Went after I went after their, you know, head of North American sales or head of the marketing, and, you know, I even pulled in an adviser who then became later my COO, who was also from Zendesk and worked with these folks. But, basically, you know, that was the the commercial engine for the business because we had built Duo's go to market so differently.
Dug Song:And that only came as a result of, again, us trying things very different. Like, you know, we we started the business with $5 a day AdWords, testing a bunch of things, seeing what what people were interested in, trying to figure out if, again, there was a different signal in the market for security or people needing it than what was traditional, which was, like, you know, through resellers and VARs and, you know, the folks who were also consulting, right, to their to their clientele on security strategy. So for many of our customers, they they had nothing like that. They they weren't engaging security VARs or anything like this. And so so we tested our way to a bunch of that kind of stuff and found that, again, it worked.
Dug Song:And so over and over again, the only thing we did better than our competitors was we learned together new routes to success that our competitors never found or never took seriously. And and so the practical advice I'd have for founders in in thinking about how to do this is, well, one, you know, hiring in a sort of college town, you know, where you have a large research university where you have a lot of bright eyed, bushy tailed, you know, talent looking to to get into new things. Because, you know, the the majority of my my work for us to do, I'd never worked in tech. Right? Like, there's not a lot of that here in Michigan.
Dug Song:And so so I need to augment where needed, right, with a couple leaders here and there, right, from the Valley or or elsewhere. But but, again, the majority of my team had never worked tech or certainly had not worked in security. But we we did have the security people where we needed them, and we had, like, a deep bench of hackers like myself and Jono in Duo Labs and a bunch of our product side. But, like and we had just as many that weren't. And I think that was a huge part of our success because we had a very diverse team and diverse in in all the ways.
Dug Song:You know? 40% actually of Duo was was women and underrepresented minority, which is actually very different than cybersecurity, which I think is 11% typically. But we also hire people from all kinds of backgrounds that had no engineering background, whatever. You know? Again, like, a lot of my best hackers I ever worked with never had, like, a college degree or, you know, whatever sometimes.
Dug Song:And so so we could solve problems sort of from vantage point perspectives. And the largest part of, again, what we needed to be successful in doing so was building the kind of culture where that diversity of opinions or perspectives and ideas would lead to creativity, not conflict. You know? But I took to heart seriously what what Steve Jobs once said about creativity, which is that it's not about having some idea no one's ever had before. It's about combining and smashing together ideas from different domains, right, to lead to some different result.
Dug Song:And I believe that. I've seen that deeply. I mean, that's, again, a lot of what kept me here Ann Arbor. So many different interesting ideas. Like, when we were building Arbor Networks even, you know, that second company, there were folks I hired from epidemiology, right, who were helping us build, like, interesting viral models of self propagating worm, right, infection, right, within enterprise networks.
Dug Song:We never had would have had any idea about how to do that and then how to defend against that and build, like, these sort of cell containment sort of algorithms if had we not sort of had access to people who had these crazy other sort of ideas, or crazy it was, but, you know, very well trod and very watershed right in in other fields. And so so the one is, I think, start by having as as many different kinds of ideas and people as you can. We we practically on our website, we had one question and for in all of interviews, right, that we started with, which is what makes you unique? Right? What what makes you unique?
Dug Song:Because I don't need 10 people with the same background in any meeting. Right? I need if they all have the same ideas and same opinions, the same background, I need one of them, not 10 of them. Right? And so I I I need to understand, like, for any person we'd hire, especially in an early team, what do you think you is special that you can bring to us that we don't already have?
Dug Song:Right? How does that augment kind of our capability set, right, and then what we think we can do? And what do you know that we don't? What have you done that we haven't? All this kind of thing.
Dug Song:And so, you know, that was really important to us, and it it led to so many more interesting conversations about then how do we tackle this. And and, again but it just led to more challenges in terms of how we'd have to manage, but that's why I took management so seriously. So for early founders, like, let's say, you know, in building a learning organization where you're bringing in a diversity, right, of talent in this way, you have to get good at management. You have to really focus on, again, how do you elicit the best out of those kind of diverse teams? And, again, you know, you see elements of this in a lot of other even big companies.
Dug Song:Right? Like, I think Bezos has some really interesting lessons, right, to learn from from Amazon. Though only later, if he wrote some books or, like, someone wrote books about what he'd he'd done, we realized, oh, wait. That's just like us. Right?
Dug Song:Like, disagree and commit. And I say that all the time. Is he like, not disagree and commit? I say, well, you know, I I don't agree with that, but we're gonna we're all going to say you know, we're all gonna make sure that it happens. Right?
Dug Song:And I'll make some support that idea. And the only reason we did that is because we had a commitment to learning together and practically had rituals and operations to support that. You know? Blameless retrospectives, right, where we'd figure out what was right and not who was right. We had an unlimited book budget.
Dug Song:Right? Anyone who wanted to buy books and get smarter, well, why would we stop them? Know? Buy those books. When you're with them, put them on the shelf in the library and tell us what you learned.
Dug Song:Right? Share share it with others so we can all sort of benefit. We had rituals like appreciations, which, you know, ended or started or ended every meeting in the company, including all all hands meetings even. Three to five minutes of people thanking each other publicly for the things that they'd seen others on the team do that made the team successful. But that's how we learn because, you know, we spend all our time as leaders trying to impart kind of our ideas and wisdom or whatever, not wisdom, but, like, opinions, right, to to our teams at large.
Dug Song:But how do how do leaders ever hear about what's important, right, or what's working? And so, you know, we had these sort of cultural rituals, like appreciations, where also they need the fact that, you know, positive feedback is so much more important than negative. But, again, in in all hands meetings, you have someone call, hey. You know, babe, you know, thanks, you know, Zoe, for uploading those leads within twenty four hours from RSA. We had this, you know, this many sort of SAOs or opportunities created out of that.
Dug Song:But, anyway, anytime anyone did anything good, it was publicly called out in this way so that others could follow. And that's how we elevated and standardized excellence across our organization. It was not by accident. We built a culture of it and a culture that I didn't have to go and sort of be everywhere to sort of drive. Everyone, right, was sort of and in, you know, in some other ways, like, anytime we promote people, we we anyway, long story short, we had all kinds of system by which, again, we we supported an organizational learning in the business, and that came from taking kind of our job as managers seriously that, again, just like as, you know, engineers, you're you're building systems, right, of of code and all that kind of thing.
Dug Song:But as as managers and leaders, you're building systems of of people and and work, and and so we spent a lot of time really focusing on how to do that effectively, hiring, you know, folks from the university who also done, you know, instructional or, you know, curriculum design and does a whole l and d, learning and development sort of organization within Duo. We had, you know, training budgets for folks. We also had, again, a lot of internal conferences and ways in which we shared kind of our best practices with each other. Anyway, so there's a lot to it, but that's these days with founders, that's what I spend a lot of my time doing, just making sure that other founders have more in their toolbox to kind of achieve success from the lessons we learned in in trying to kinda build this stuff. But, you know, none of it's proprietary.
Dug Song:Don't and, also, none of it has to be done this way. I just think that there this probably is it's the
Mahendra Ramsinghani:most fun way to do it, right, where everyone grows together and everyone can kinda claim success as a team. Thank you, Dug. As you talk about spending more time with founders and you take this unique example of what Duo did in its culture, one fundamental question that comes up in this day and age is about capital efficiency or capital allocation, if you will. You know, we live in a day and age where seed rounds used to be $5.10, 15,000,000. Now, gosh, seed rounds have exceeded mean, the numbers are staggering.
Mahendra Ramsinghani:You know? You're approaching 500,000,000, billion dollar seed round.
Dug Song:My a round was 5,000,000. My seed round was 1,000,000, and I had no pre seed.
Mahendra Ramsinghani:So so I think this will be a great analogy. Walk us through your capital raising journey, but also share some advice with our audience, with our founders on how you manage every dollar so effectively, and what can founders do when they think about money and not boast about valuations as opposed to creating value?
Dug Song:Yeah. Well, part of this is also just maybe the culture difference or the Midwest where because tech isn't sexy here, you know, like, people look at you as a tech out of there, what do you do? I guess, what is that? You know, it sort of kinda weeds out a lot of I wanna say the I wanna say wantrepreneurs. I mean, that's that's kind of mean.
Dug Song:But but I mean to say that people don't care about those vanity metrics that are so important to people in the Valley. Like, I remember when when we kinda did this round that, you know, we became unicorn. The time, there's only, like, a hundred unicorns. Right? Is no.
Dug Song:Back back then, I was a bit embarrassed about it. I didn't really wanna talk about it. You know? I was like, you know, I was like, I don't so my team member's like, oh, we're joining the unicorn club. I was like, please don't say that again.
Dug Song:Like, this you know what? It's not none of that matters. Like, you know, like, do you see this this the new account we just closed? And, hey. Did we just deploy you know?
Dug Song:Like, we did you see we stopped the the Russians again at this You know, we had all kinds of other things to be proud of that were really about kind of our customers, right, and our our our you know, making them successful, not not a not about us. But part of that is this kind of this this look in in Michigan of of of of of, again, always looking outward. Right? Because, you know, Michigan has been the, you know, history of building industries through export in this way. And so whereas, again, I think in in some ways in the valley or places like New York City, you know, you you can sort of be caught up in these echo chambers, right, of of companies buying.
Dug Song:Like, would startups buy from startups and all I'm like, oh my god. This is, turtles all the way down. And so for us, you know, we were always focused on those kind of results. And, you know, even in the early setup, we had monitors in in our offices with every deal. Like, we built, you know, kind of these software dashboards for our business that when we closed deals, we'd see them pop up, and, you know, we all celebrate bang the gong, all this kind of thing.
Dug Song:You know, it was all that kind of stuff. And so for me, like, I know that historically in the security industry, there's been sort of this weird cultural divide, right, between sort of the product and tech folks and then sometimes the go to market teams and all that kind of stuff. I lived that, right, at these other companies, and I didn't want that for Duo. I just thought, look. You know, we're we're building an integrated sort of go to market where the product is the marketing.
Dug Song:When you kick the tires, try before you buy. You know, in SaaS, you know, you have to be product led because, you know, there's nothing to install or remove. You know, it's product is the demo, is the marketing. And so we worked to create a focus on the customer from the start. You know, every engineer I mean, it's kinda weird to say, but, like, every engineer at Duo, through my tenure anyway, had been part of a customer conversation directly at some point in their career.
Dug Song:And and, yeah, they could even sign up on internally for sales calls, right, where, you know, our reps are talking to the customer because they need to hear that. Even if they wasn't even if weren't gonna say anything, they need to internalize that point of view. Like, what is the customer actually dealing with? Why did they come to us? What's the positive business outcome they're looking for, right, in in looking for our solution?
Dug Song:And it's created, like, a completely different empathy. And, like, at our all hands meetings, we'd have a customer there, you know, talking about kind of all this stuff because, you know, that that's why we have a business, right, at all. And and so, anyway, we've spent a lot of time kind of focusing on on that that kind of orientation. And as a result of that, it leads to a fluency with the operations of the business when when people, you know, can empathize. They commiserate.
Dug Song:Like, oh, yeah. That part of our customer journey really does suck. Like, I need to fix that. Right? Look.
Dug Song:And people care differently, right, when they sort of are have that sort of exposure and then point of view. The other thing we also did, you know, just pro tip for founders out there, we we we used to do a board report every six weeks. I had a very board meeting or very board calls. So we quarter quarterly board meetings, make quarter board calls, right, checking in on progress, quarter with the board to see if there's anything they could do to help. Ahead of each each one of them, I had a board report where as a Google document, I'd have each of my department heads write three to five paragraphs of the plans, progress, and problems in their business, sales, marketing, customer success, product, technology, or, you know, engineering, whatever.
Dug Song:And I'll write the preamble, which is the story of the business, and I'd share it with the board. And they comment on it right before the board meetings, and we focus our board discussion on the two of the topics of strategic concern. Right? I wouldn't just sit there reading the slides to them, and, you know, I'm not doing weather reporting. I'm I'm here to actually have us have a conversation about what we need to do with the the company.
Dug Song:And after a board meeting, we'd sanitize it. I would share it with the entire company. And so every year, we had eight of those reports, right, on Octave basis, right, every six weeks. The first of those every year was our strategic plan. You stapled that together, and it's the book of duo.
Dug Song:Every major decision, every major success, every major failure, every learning we ever had. And when I hired new people, not just executives, but even you know, we do hiring classes of, like, 30 people at a time. I I I used to do all the onboarding classes with with some of my team. We have them go and look at that. Read the last four, five, six board reports.
Dug Song:You know? You will know everything that we've done. And it was amazing. They have these, you know, even fairly fresh college graduates come out of sort of a first week at Duo where they've committed code, and they've also read kind of a year's worth of, you know, the every major business we made and all the numbers and everything, and they're like, I know kung fu now. Right?
Dug Song:It's just like they've he's, like, ready to go. And and so it was that kind of you know, actually, you mentioned Zingerman's earlier in the call, Mandara, but Zingerman's was a little bit of inspiration for some of this because, know, even as, like, a small well, 70,000,000 a year, a Jewish Jewish deli vertically integrated with all their these different businesses, they did open book finance. Right? They they shared all their their their numbers, operations with their entire team so people could actually have empathy for what they would have to do and and, again, come up with their own solutions, right, to how to improve the business and the margins, all this kind of stuff. That's what we did as well.
Dug Song:It just and it scaled really well. So, again, it led to outsized performance for us every year. Every year, you know, most of the years, we doubled the team and we tripled revenue. And so, yeah, you know, it was it was a way to align all of our team to the realities, operating realities of the business and and and and really see how to contribute because they they could then create their own commitments, right, in planning and toward what we'd have to do to to actually move the numbers, move the needle on these numbers, and and really help build something unique.
Sid Trivedi:Dug, we're getting to the end of our conversation. You've been fantastic throughout it all. One last question for you. Since your success with Duo, you talked a little bit about, you know, all the things you've done post Cisco. But one of those is you and your wife have spent your wife, Lynn, have spent quite a bit of time thinking about how to give back to the community and how to reshape philanthropy through impact.
Sid Trivedi:Maybe just share with our listeners just one example of an initiative that you've undertaken with your wife and and why you've done that. Yeah.
Dug Song:Well, we we started a foundation to give where we live, and the kind of scope of our giving tends to be know, Southeast Michigan, although we've done some in Baltimore where I'm from as well. But in both cases, you know, we're we're doing this to create community wealth, you know, to be good neighbors, to help build the community that we wanna be part of. And by community wealth, I don't mean just economic wealth, but, you know, social, cultural, environmental. Right? And so we think about sort of what it means to sort of build what refer to, you know, MLK on this.
Dug Song:Right? But Martin Luther King talked about the beloved community. Right? One free of, you know, hunger and hate. And I personally think that the tools that we can kind of apply and bring to serve our community in this way are the lessons that we've learned in many cases from from entrepreneurship.
Dug Song:Right? How to be successful doing these kind of things in ways that create much more shared prosperity and and and and wealth. And so so a lot of what we do these days is focusing on ecosystem building, making sure that many more people have the opportunity to do what we've done in terms of building a a a successful technology driven business. And an example of things that we funded that's kind of caught caught fire in Detroit, which is a super majority black city. It's the blackest city in the country.
Dug Song:Nearly 80% African American is called Black Tech Saturdays, and it's it's a movement, basically, that we've helped to fund and support in well, you have 12,000 members, you know, coming together to to build again a a culture of tech innovation that is welcoming and inclusive, right, of of people across all the experiences that that people have lived, right, in a city like Detroit. And so so those are things that we're really excited about, and there's some great companies we invested in out of all that. You know, it's we're trying to create sort of the virtuous cycle, right, of founders reinvesting kind of their not just their capital, but their expertise, right, into their ecosystems in this way. And so so, yeah, though Duo was the first unicorn, first multibillion dollar tech venture backed exit in Michigan, there have now been nine more. And we've, you know, thankfully been able to invest, you know, in some of that along the way, and and I think we can help drive a whole lot more than success in a place like Michigan that really needs it.
Dug Song:You know? We you know, Detroit's not completely out of the woods, but it is a beautiful and amazing and emerging ecosystem, particularly in tech and start up land. And I encourage any of you. Right? You were looking for amazing deals with founders who are built differently, you know, know, because you gotta be pretty resilient, right, to kinda build tech in a place like Detroit and resourceful and scrappy.
Dug Song:And and, again, like, it's every place about something. Detroit is about resilience. It's about grit. You know, these are folks who, again, who, again, has just been through hell and Mac. Right?
Dug Song:The first city in the country to have gone bankrupt and all. But, man, if you're looking for, like, resourceful founders, Detroit is full of them, and we're proud to be backing a lot of these folks. And so, anyways, investors, if you ever wanna look at at this stuff, let me know. We we're syndicating all kinds of deals. We we write a lot of first checks to a lot of founders, and you'd be surprised the scale and ambition of a bunch of these companies that are just like like, I just had one launch yesterday called Electric Plant Company, Electric Plant dot co, and they're doing planetary scale.
Dug Song:They're kinda building for plants. And number one, that's, like, a bit of mind bender, like, talking to plants and hearing what they're saying. But second is, like, the scale of what they're doing, which is, like, planetary scale. It's kinda amazing. We've got we've got very ambitious founders building very practical businesses from the start, global ambitions, but acting locally, and and so that's what we're supporting.
Dug Song:And if anyone wants everyone to join us on that, let
Mahendra Ramsinghani:me know. You know, we're happy to happy to partner with folks. Dug, as we wrap up, I wanna take this opportunity to thank you on behalf of all the founders in our community, obviously, on behalf of my cohosts, Ross and Sid. And I was trying to think that what are the best way that your image can be presented to our audience? So in my head, I have one side of you, Dug, which is the skateboarding, Dug, that I that that image is seared in my head with a laser.
Mahendra Ramsinghani:Mhmm. Okay. Right outside Zinger Min. Now when I look at you, and for the benefit of audience who may not have the pleasure of seeing you on camera, I see the shade of, like, a Dalai Lama like look that has come on your face. I mean, I was walking the document to you about the Dalai Lama literally last night, and I said, like, Dug's side profile is actually like the Dalai Lama.
Mahendra Ramsinghani:Okay. So if I draw this Venn diagram of a skateboarding Dalai Lama who's trusted in security, that is Dug's song for all of us. That's the song that you see that I feel like you're gonna leave behind. So thank you, Dug, for all the good work and amazing culture that you built at Duo. We have never heard such a story of not just thoughtfulness, but creativity, rituals, and above all, care about the customer.
Mahendra Ramsinghani:I think that is one thing that our industry really needs to build upon, and so thank you for blazing a path into this future.
Dug Song:Well, thank you, Mahendra. Thank you, Sid, and Ross. I I guess, know, I'll just leave with this. You know, I I don't know about Dalai Lama, but I will say, you know, my my father was a Buddhist monk back in the day, and, you know, I always left an impression on me, you know, this kind of story and history of of the Buddha and also, you know, sort of the Vow. Right?
Dug Song:Sort of if you've figured something out, you need to bring people with you. Sure. Right? In that enlightenment, if you will, and everything else. So I always happen to help, and that's one of the things I love about the startup and tech community is that sort of built on that ethos, right, of kinda giving back or maybe even giving first, right, as the tech stars people like to say.
Dug Song:So, yeah, proud to help. And and, again, like I say, if if if any founders ever benefit or learn anything from me, my only ask is that they do so for others as well. They pay for it.
Sid Trivedi:Thank you for joining us inside the network.
Ross Haleliuk:If you like this episode, please leave us a review and share it with others. If you really, really liked it and you have some feedback for us, wrap it on a bottle of Yamazaki and send it to me first.
Sid Trivedi:No. Don't do that. Mahindra gets too many gifts already. Please reach out by email or LinkedIn.
