Caine Tighe – Freelancer to CTO of DuckDuckGo (#26)

Biography

Caine Tighe is the CTO and first employee of DuckDuckGo, the Internet privacy company that empowers you to seamlessly take control of your personal information online, without any tradeoffs. This private search engine is #4 in the U.S., Germany, Australia and dozens of other countries, answering over 9 billion queries in 2018.

Prior to DuckDuckGo, Caine founded and ran opensesame labs, a startup consultancy focusing on companies with great ideas struggling to execute them.

Click Here –> For more information about tech careers

Episode Summary

“We did 9 billion searches in 2018 with less than 70 people. We’re at 40 million searches a day now”

—Caine Tighe

Caine Tighe is the CTO of the upstart web search company DuckDuckGo that is slowly and surely taking a bite out of Google through laser-sharp focus on their one big weakness: privacy. 

Along his journey in tech, he’s transformed from a computer programmer to CTO to a leading thinker on privacy, all while living outside of the usual tech hubs.

In this episode we’ll cover:

  1. How Caine met his partner and co-founder of DuckDuckGo, Gabriel Weinberg
  2. The culture at DuckDuckGo and the amount of effort Caine puts in to ensure his employees are happy
  3. How DuckDuckGo is competing against Google
  4. Why understanding how you spend your time is absolutely essential

Key Milestones

[3:01] – Caine founded his first company Open Sesame Labs because he noticed that many people around Cambridge had great ideas but a poor product. Caine also discovered difficulties in collecting money from clients when they go under.
[6:56] – How Caine learned how to code from a Russian programmer who would delete the program every time he found a bug
[9:51] – Caine talks about meeting his partner, Gabriel Weinberg, while working as a consultant, or a freelance programmer.
[12:47] – What was it like working at DuckDuckGo in the early days?
[17:15] – The early days of hiring at DuckDuckGo were all inbound, so there was very little recruiting. This worked for 4 of 5 years, but when there were obvious gaps, the company grew to have internal recruiters sourcing talent. Now, there is also a huge mobile component to the DuckDuckGo team.
[21:01] – What is the best way to get promoted at DuckDuckGo?
[24:35] – Caine Tighe talks about the culture at DuckDuckGo
[27:42] What is the circle of competence. And why its extremely important to KNOW how you spend your time.
30:12 – Caine’s current challenges as the CTO of DuckDuckGo? How does he spend his days? How does he use Maslow’s hierarchy of need?
34:14 – Why investing in your employees is a great strategy for long term company success.
36:14 – How is DuckDuckGo competing against Google?
44:37 – Tips for getting involved in the intersection of privacy, security and technology. Also what is the difference between privacy and security in Caine’s opinion?
48:32 – Understanding how you spend your time will transform your life and career! Very important advice for listeners

Transcript

intro: 00:19 [Inaudible].

Grant Ingersoll: 00:19 Hello and welcome everyone to the Develomentor podcast. Each and every episode we want to give you insight into a variety of careers in technology. I’m your host Grant Ingersoll, the CTO and co founder of LucidWorks. To date so far we’ve interviewed a variety of guests ranging from the Csuite of publicly traded companies to self-taught developers working in a variety of industries. To that end today’s guest is the CTO of the upstart web search company, DuckDuckGo. That is slowly and surely taking a bite out of Google through laser sharp focus on their one big weakness, privacy along his journey in tech.

He’s transformed from a computer programmer to CTO to a leading thinker on privacy all while living outside of the usual tech hubs like Silicon Valley. True to that privacy forum he’s actually a pretty tough person to do background research on for podcasts since he doesn’t have a lot of public persona.

Grant Ingersoll: 01:13 So I’m going to have to be on my toes for this interview. At any rate, please welcome to the show Caine Tighe. Caine, great to have you here.

Caine Tighe: 01:21 Thanks.

Grant Ingersoll: 01:22 Hey Caine, so, you know, thanks for taking the time to join me. I mentioned the lead in that you’re, you know, I usually like to do some career research through LinkedIn and that I couldn’t really find a lot on there. So how about we just start off by having you introduce yourself, your background, perhaps some of your schooling and, and then we’ll take it from there.

Caine Tighe: 01:41 Sure, sounds good. So I went to, I mean I guess, my professional career started when I was a, as most people do at 15, 16. I was just exchanging logic boards on computers and kind of was cutting my teeth and programming since I was younger. Materially though, like I founded and ran a small consultancy that was focused on companies with great ideas that were struggling to execute them called Open Sesame Labs. And then after that like you said, I was the first employee and now CTO of DuckDuckGo you know, an internet privacy company that empower you to seamlessly take control of your personal information online.

Grant Ingersoll: 02:29 Yeah, I definitely want to dig in on that. CTO role, but tell me a little bit more about the consulting at open Sesame. So you, you started this company, was it just you? Did you have some partners?

Caine Tighe: 02:41 So I went to union college and I and it’s connected in New York and I dabbled in computer science, math and physics. You know, the, the three Musketeers as it was, like my mother’s a pediatric cardiovascular surgeon and everyone always asks me what, whether or not she was going to push me into medicine. But she did a pretty good job of letting me love the computer and find my poetry with that.

But I’m open Sesame labs was a company that I founded because I was noticing that at least around Cambridge, there Cambridge, mass, there was a lot of companies that had these really cool ideas and you know, somebody would write a whole bunch of software that like, it was just not good. And then when the product would start to do as they were identifying product market fit and as they were you know, pursuing those ideas, they would run into this, or at least some of the companies would invariably run into this issue where the product just wasn’t up to snuff.

Caine Tighe: 03:43 And so I really enjoyed working on multiple projects at the same time, keeping really, really busy. I did that by myself and I had somebody do the accounting and making people pay because I had a hard time with that when I was 20. And, I really had a hard time cause I really wanted, I wanted to forget about the money. It always like fell by the wayside.

I was convinced that, you know, if you do good, good, we’ll come to you. And so I would hope the money would follow. And it turned out sometimes companies would go under owing me three, five, $10,000. But that was okay cause you know, I I still had a once, once I made that mistake enough, I I got someone to collect for me and that was good. But others and other than him, I didn’t really have my friend Barrett other than him, I didn’t really have anyone helping too much on the programming side except for my network of people.

Grant Ingersoll: 04:40 Yeah. I mean, that’s, I think one of the interesting challenges around being that individual consultant, you know, it’s often feast or famine and, and the thing that you know, you’re actually really good at, like in your case programming often means that there’s these other things that you just don’t want to do, like build collections and, and things like that. You, you hit on an interesting thing there. That’s your, your, I don’t know if it was your mom’s statement or yours, but this notion of finding your poetry, explain a little bit more what you, what you mean by that?

Caine Tighe: 05:16 Well, I mean, you know, it’s the computer, when I mean, when I was young, I was about 10, you know, 10 years old. When I really found the computer, I was lucky to have, you know, have the opportunity to work on an old computer and play with it. And it was clear my mom always had this idea that there was poetry in things.

Ffor me it was very clear early on that the computer digital watches cars, things that were related to complicated engineering problems, like I would always take them apart and put them back together. And the computer really stuck for me. I, my first, I bought it off of UBID if anyone actually remembers that site 266 megahertz. You know, I don’t even know what the, what it was at the time, two gigabyte hard drive, 128 bags around my $2,000, my entire life savings. Just to get on Netcom. But I mean it was clearly my poetry. I just, I know I was that kid that everyone was yelling at to get off the phone cause I was always just dialed into the internet making trouble.

Grant Ingersoll: 06:28 Yeah. It was back in the good old days of AOL shipping out CDs so that you could get on the internet and all that good stuff. So that early computer, I mean, were you programming right off the bat or was it more of a tinkering and taking apart or like what I would do is like, just try to figure out how I could run my favorite game on it. I didn’t much care about the other stuff in those early days. I just had to figure out how to get the game I wanted to play loaded.

Caine Tighe: 06:56 I mean, at first it was for me it was programming like I took to it because [inaudible], you know, net addition to her heart surgery, there were, I was, she was starting a noninvasive glucose monitoring company and we had programmers there all the time. And, and I was like, I don’t understand how this works. Like I understand someone explained it to me and she introduced me to this Russian programmer who every time he found a bug in one of my programs, he’d delete the entire program. And so I made calculator after calculator after calculator.

And, and it was, it was a really great experience for me. I was programming. Yeah. Then, and then [inaudible] turned into trying to get the red hat Linux for dummies phase, where like I wanted to get Linux to run perfectly on my laptop, which was an absolute nightmare at the time. And I just found it fun to try to get every little module to work, every driver to load and then kind of cut my teeth on some kernel programming then. And driver programming and,

Grant Ingersoll: 08:09 Well, let me, let me make sure I heard you correct. This is a programmer friend of yours. Every time he found a bug he would delete the program.

Caine Tighe: 08:20 Yep.

Grant Ingersoll: 08:21 And so you had to start over from scratch.

Caine Tighe: 08:24 Yup.

Grant Ingersoll: 08:26 That is, that’s such a like a old school teaching program, right?

Caine Tighe: 08:30 It was like, you know, kind of Sisyphean in that way. But it was, it was a, it was a really good experience because I focus it like, it taught me early on to really focus on making sure that my, the way that it was written was in a way that it could be understood and that I could understand it again. Yeah. I really, I really focused on, on that. And, and that kind of informed some of my loves and some of my hates about programming, which we can get into if you want composition versus inheritance and other things like that. But yeah, that’s where it started. It all started pretty young.

Grant Ingersoll: 09:15 That’s a pretty amazing mentorship, although I don’t even know how in programming you ever graduate from that school. Let me guess. You pretty much would be deleting every program ever because they always have bugs.

Caine Tighe: 09:31 You get up one day and leave.

Grant Ingersoll: 09:32 Yeah, no, that’s fantastic. Although like, like you said, I think that’s a great way to learn a little bit draconian I’m sure. But Oh, so, so you’re at open Sesame or you’ve got this consultancy and then did you go straight from that to DuckDuckGo? Or was there any transition period?

Caine Tighe: 09:51 So I had met Gabe prior to all of that online, you know, like, I mean, Gabriel Weinberg, the CEO, founder of DuckDuckGo my, you know, is my mentor as well. I met him on, on hacker news and then we started to exchanging emails. But the point is, is my transition kind of was that he was working on a company or was a advising or head angel invested or both? Usually there together.

A company called WakeMate, which was a kind of a sleep cycle, a device that you would have on your wrist. Hmm. And it would determine your, you know, your rhythm and your REM sleep and when appropriate to gently wake you up based on your movement. But it was like a better signal to noise then just putting your phone’s accelerometer on the bed. Anyways, I thought it was a pretty sweet idea and they were having trouble executing, which was kind of the mission statement of my little.

Caine Tighe: 10:57 I mean, consultancy sounds so nice. Like, you know, overly important. It was more just me contracting and banging on the software. But you know, and then I met him there and I, I tried to bail that company out. Didn’t exactly work with all the technical stuff that was going on there and how it was organized. But I, you know, got to meet Gabe and work with him more closely and then I started volunteering my time on his Android application for DuckDuckGo.

Just cause I was like, this would be cool, you know, just to see how it works cause how is he working on search, where’s the index, how is that working, you know? At least if I could make some API calls I could get a better idea of the architecture of what he was working on. And after that I’ll just, I just kept working for him.

Grant Ingersoll: 11:52 Yeah, I mean, interesting. I mean I think you hit on some really key things there and this just even in my own career of, you know, that volunteering with something like open source or you know, in this case a kind of a shared source or open source, however you want to look at it. You know, just the people you meet and then being open to, to what comes next is sounds like a pretty key thing. It sounds like you have a few of those kinds of serendipitous moments.

You know, first off it sounds like you have an incredible mother who, who would just encourage you to go out and explore and then, you know, and then you kind of come in to randomly meeting Gabe on the internet and the rest is history. So then, you know, take me into DuckDuckGo a little bit in into your role as, as CTO and kind of fill in our guests a little bit about what’s all like, what is your day to day look like in that role?

Caine Tighe: 12:47 Sure. So I think the one thing that I missed here in my transition was that I could have worked for other startups cause like I, yeah, it was like literally my entire thing was like going to look for startups. But the thing that I was also looking for was mentorship. Like figuring out how to spend my time effectively. So that’s that was a huge draw to DuckDuckGo because like Gabe just knew and still knows more than I do and it’s been a very fruitful relationship for me to like figure out how I’m supposed to spend my time.

And I think, and at duck duck go, what I originally was doing was identifying what was preventing people from using the site. In the early days what that was, was like, you know, our competitors, we’re working on videos or acquiring YouTube or you know, working on their own image indexes and they had Google maps and Bing maps and all that other stuff. And so I was just trying to fill out

Caine Tighe: 13:55 [Inaudible] major verticals through, you know resolving the user’s intention on the way in. Is it a MAPI query? Is it a newsy query?An imaging query? And trying to like filter that intent to the appropriate vertical and identify an upstream provider. Because in search there are a lot of valuable API APIs and a lot of valuable data sets that are not just, you know, from Google or from anyone in particular. And we were looking to identify those and kind of treat those as commodity and build a private search experience that the key value there was supposed to be that it was a private, a private search engine, not like the world’s best search engine or most technologically advanced or whatever.

Grant Ingersoll: 14:42 Yeah, I mean, you know, w was the privacy thing. I’m trying to remember, you know, I’ve been a long time DuckDuckGo user as, as you know, and but you know, it was the privacy thing, always the cornerstone or I kind of seem to recall there was kind of a, an inflection point where you all really just latched on to, Hey, let’s really take and pound on this now. Right? I try to drive this wedge as deep as we can because the world is waking up to the fact that, you know, everybody’s trying to monetize them.

Caine Tighe: 15:15 Right? So, yeah, you’re right. This site was started in Oh eight. And the basic premise was before privacy was to leverage structured data to provide a better search experience. And then as a Gabriel, I wasn’t involved at the time as Gabriel was working on that idea. Mmm. The idea of privacy came in through feedback and they were like, what about I P logs? What about user agent logs?

What about all this? And Gabriel, it was like deleted. And there’s like this really funny like Reddit thread where someone was mentioning this stuff and Gabe just decided in that moment that he completely agreed with that ideology and basically set the no collection. You know, we do, we do not collect or store or share private information and personal information. Then from there, you know, that’s, that’s the product and, and what has led to our vision, which is to raise the standard of trust online and the mission, which is to be the company people trust most with our online privacy.

Grant Ingersoll: 16:23 Yeah. That’s fantastic. And I think so important. And so, you know, in many ways you’ve grown up with this company as well, right. You know, you kind of come in, you’re the, you’re the sole programmer kinda, well I suppose though Gabe is programming too, but you, you’re, you’re wiring together all these things and then you know, you slowly, but you know, again, kind of talking about Sisyphean tasks, you’re, you’re slowly but surely rolling this Boulder up the Hill that is internet search competing against these behemoths.

And at the same time, like I imagine in your role as CTO, you’re, you’re bringing on new people. You’re, you’re having to build out infrastructure within the company to support a larger and larger staff. You know, talk a little bit about how you go about building a team like that and convincing people to join and what you look for.

Caine Tighe: 17:15 So there been in many eras to this. The original era was what we called inbound hiring. We basically did no external recruitment or anything like that. I mean, we would occasionally post on hacker news, the who’s hiring thread, but all of our requests came inbound. People just proposing that they would be a good fit for the company and we’d evaluate people as they came in. That worked for a great very many years and probably four or five.

Then we had to refactor the entire thing as like, we had obvious needs that were not necessarily being filled. And so like in terms of building, I find it to be pretty different. Like building a team is different than just building the entire engineering organization as the first employee. I’ve built more than just the engineering team here cause I feel like the culture is even more important than necessarily the hiring.

Caine Tighe: 18:20 It’s actually surprisingly my favorite part of the company. Mmm. But I guess the way that I think about how to build an effective team is to make people feel safe at work. And so I, yeah, I guess I focus on culture. Our current hiring methodology is we have internal recruiters, Mmm. Two of them that are primarily focused on identifying the needs of the organization and then sourcing those positions.

But another good example of building a team was up until, you know, a year and a half ago. We are, yeah, two years ago, a year and a half ago, we didn’t have a mobile team. We had, we were working with a third party to do that. And then we had to bring it, we had to bring it in house. And I think there, what happened was, is we had identified a really great mobile developer in our, our engagement with the contracting firm.

Caine Tighe: 19:17 And I just basically said to the leader of the contracting firm, would you mind parting with the subcontractor? And he said, kind of, but not tremendously. And I said, okay, well, you, I basically took a bid on that. Yeah, he, she came in and, and basically formed the beginning of that team and then helped me think about and identify the criteria. For example, do we care about cross-platform mobile engineers? Do we care about specialists?

What is the mix of specialists across platform? And what type of culture do we want to build within the mobile team? And from there I think we, we take a mental models first principles approach to building the teams instead of assimilating them into the company. So things are pretty you know, independent in terms of the functional teams in the company.

Grant Ingersoll: 20:15 Interesting. I mean, and, and you know, this is one of the things that even in my own transition into a C level role of, you know, getting it, you just have to shift the way you think. And so I want to pull on that thread a little bit more around culture and the mental models there. And could you maybe go a layer deeper you know, to the extent you can talk about how you, how you think about those things and how you go about creating that.

Cause frankly, like early days of my company, it was something we honestly screwed up and it took a bit to get a to get it fixed, if you will, to get it is sustainable to get something that people really feel good about. You know? So talk a little bit more about that for me, if you will.

Caine Tighe: 21:01 Sure. So like, this is what I’ve learned the most. Mmm. And this, you know, you hit the nail on the head. I really have grown up with the company which has been a tremendous opportunity for me. Aye. The way in which we incentivize and promote people within the company is based on their ability to contain complexity, which is just another way for saying leadership.

So I think [inaudible] that the most important thing you can do is provide people a problem statement and set expectations about what it is that you want done and then to basically make sure that they have appropriate advisory and then just be done. You know, let, let them try to solve the problem. And, and then if they do without any problems, great, give them something a little bit more complicated. If they don’t, that’s a little bit sad, but you also have to hold them accountable for it.

So foundationally, I think, you know, when you work at this company, the incentivization structure and the advancement structure is all based on Mmm. Leadership, your ability to do more impactful things for the company. And there’s a lot of opportunity for that.

Grant Ingersoll: 22:21 Yeah. No, it’s interesting cause I mean like, like you said, you’ve grown into this role. I mean, it was just something where Gabe helped you out a lot. I mean, any, any particular inspirational that, you know, I don’t know, books or anything that really helped you see the light on these things? Cause you know, like you go from being this individual consultant where you’re, you know, the only one you’re accountable to is to yourself, obviously to your customers a little bit too.

But, but then all of a sudden, you know, you’ve got, I don’t know how many engineers and product people you have these days, but I’m going to guess it’s more than 20, so, you know, not all of a sudden. Yeah. And so now you’re, you know, you’ve got hierarchies, you’ve got managers, you’ve got teams. You know, you’re managing teams, you know, what was that growth part like for you and how did you go about scaling yourself?

Caine Tighe: 23:09 So, yeah, that’s a great question. We have a leadership library. There’s, you know, we could go into books. The advantage by, I can’t remember, is Patrick, we NC, Oni, I think maybe principles in life and work by Ray Daleo. You know, the hard thing about hard things, these are kind of like, you know, the best hits, you know, greatest hits, like you should read them. And you don’t have to read them, listen to them in your car or bike or whatever you on your walks.

And it’s just, it’ll just, I feel like it just made, made me happier and it made me being a leader is a lonely thing even if you’ve been there the whole time. Because it just is, it is, it can be lonely. And I think hearing that and being reinforced over the books does help. Tying back to my, my programming, the way that I thought about building the organization is the way that I think about programs.

I literally started architecting the organization as a program and it came to my reel. I gave an, I had a lot of conversations about this over the years. And I think the right way to do it is the same way that you should write programs, which is to focus on a composition based model. Does a relationships instead of has a relationships and many companies, I mean again many maybe your listeners may not know, but DuckDuckGo is a purely remote organization.

Caine Tighe: 24:35 Like we don’t have, we do have a headquarters but like three people are there. There are more people in a satellite office than there are in our headquarters. So that’s also architect helped architect our organizational structure. And I think the, some of the key insights there are how we organize the, how we’ve been able to be productive is how we organize the company, which is around expectations and around behavior as opposed to around people.

So if somebody, you have a functional team, which is where you may be a front end engineer, where are you are participating in conversations about your functional expertise. Do you have an objective team in which you’re supposed to be, you know, working on a strategic imperative for the company, which is where you discuss your, you know, your work, your day to day work, which is not necessarily related to your functional expertise.

Caine Tighe: 25:26 And I think having those different conversations allows people to allows us to form an idea meritocracy where the most powerful people in terms of a functional expertise are people that are strongest at, in this particular case, running engineering, but they may not be the strongest strategic thinker. So trying to have like ha, you know, what is normally like a front end manager that manages five or six people and their entire lives including their professional development and everything like that. It doesn’t appreciate the separation of concerns and like separate requirements. And so we break all of those roles up.

And we have, you know, a functional team leader. We have a career advisor who just works on that. That’s not, that’s not the functional team leader. We have objective leaders. And, and that separation of concerns allows, it really celebrates people’s strengths, which is something that I really, I believe in and I think has gotten us to better throughput.

Grant Ingersoll: 26:34 Yeah. Wow. That’s, that’s, that’s super interesting. And I’ll be sure to link up in the show notes those books. But I mean, I think there’s some, some really interesting cultural ideas for, for company in there and couldn’t agree more with the, you know, being senior leadership is, is pretty lonely, although I don’t think anybody’s going to shut it to your, for any senior leader at any company.

Grant Ingersoll: 27:03 Shifting gears a little bit here, Caine, you know, kind of as you reflect on all of this, I hear two really interesting themes. One, you know, in crafting your career, you sought out mentorship and learning first and foremost and kind of pair that up with you know, what’s, of course things you love, but, you know, delve a little bit more into the mentorship side of it. Like I said, it sounds like you had an amazing one in your mom sounds like Gabe plays a lot of that role. You know, for our listeners who perhaps aren’t, haven’t thought about finding a mentor, what do you think are some key things that you really should look for there?

Caine Tighe: 27:42 Sure, I’m going to have to keep this podcast away from my mom. I think she’ll be too excited to hear how much I’ve talked about her. She won’t believe it that read from that. You know, I think there’s this idea called, you know, at a mental model called the circle of competence, which is something I believe Warren buffet, Bennett or doesn’t really matter. But the idea is that there are things that you certainly know, there are things that you think that, you know, and then there are things that you don’t know.

And that area, those concentric circles, like that particular area of the things that you think that, you know, that’s where you’re the most dangerous. Mmm. And I think I realized that pretty early on that like I had a fair amount of horsepower to like do things that I wanted to, but if I wasn’t putting that in the correct direction that I could go astray. And it was important to me to identify the appropriate way to spend my time.

Caine Tighe: 28:37 And honestly I was at 21, you know, a lot more, a lot or like it was a lot more immature. Yes. Less mature. You know, I would, I had more ego and know, gave, dealt with that and put me in my place a fair number of times. I think that it was important for me to have a strong mentor that could articulate and really get to the root cause of problems that we were facing as a company and how I could best use my time in a productive way.

I think that’s just really important for people to, to seek out and whether they do it through books or they want to construct a relationship with a mentor, you know, I think how you spend your time, there’s like nothing more important than that and understanding why you’re spending your time that way. And that’s really the crux of my mentor. You know, my mentor, mentee relationship.

Grant Ingersoll: 29:37 Yeah, no, that’s really interesting. I mean, I think especially like if you come from a programming background, sometimes it’s like, Oh, well let me just write a little more code. Right? And, and, and sometimes the answer is no, you shouldn’t write more code. And a whole lot of times the answer is you should delete code. I think you’re a, you’re Russian friend there was preparing you for the future there, but so some really important concepts there. So, so how do you think about prioritizing your time and in your role and CTO as a CTO?

Caine Tighe: 30:12 Mmm, yeah, that’s a, that’s, that’s a hard one. I think for me, it, eh, I’ve as you probably know, co-founding your own company, you replace yourself on a cadence. If you’re co if your company’s success is you know, succeeding, which is like first you do, you know, programming work and then you attempt to manage programming work and then manage, manage programming work and then everything starts to break and you need process.

And so for me, I have set my North star on doing what I think is, is most impactful for the company at any one time, which started with me identifying the things that we weren’t doing or the ways in which the organization was slow and then attempting however possible to fix that. In some cases it was hiring and some cases it was developing technical designs. And so in terms of prioritizing my time, finally what ended up happening was I was just asking myself what I could take off of Gabe, our CEO’s plate that kind of fell into my purview.

Caine Tighe: 31:27 And where I’m at now with all of that is basically I set out to achieve a principal or something. Like I have the year of throughput, you know, and then I like try to identify by the ways in which duck duck go [inaudible] is having trouble. And then I identified technical designs for example, was one way that we were having [inaudible] in trouble. People were writing PRS and then there was not enough upfront thought and that was a new problem, surprise, which I’m sure many people are not surprised about.

Then we instituted technical designs and it instead of doing all this back and forth work, it became a vector, they would just go forward the entire time. And that was very valuable and it set expectations. Honestly that’s when I got really excited about culture because I realized how powerful this thing was. And I was under this, this really bad misconception where I was like, if what I want to fill out a technical design, you know, like do I feel like that’s red tape?

Caine Tighe: 32:30 Like is that disrespectful? And it really isn’t because when you think about it, those things, if you can remove yourself from the equation, they’re not about you. There are about everybody else. And making an ecosystem and a nice place to work. And I think now my primary focus is kind of transcended throughput into making the workplace, you know, making people feel safe at work because when they feel safe at work, it’s almost like Maslow’s hierarchy of needs. Like once all your people are, they’re not worried about how they’re perceived in the organization and all this stuff. They’re all moving in towards self actualization.

And when you get these people that are just thinking about how they’re driving their own future and they’re all in this growth mindset, there’s just such a better, the outcomes are just so much better because they’re synthesizing their own best interests with the best interests of the company and they’re actually being honest about those things. And so that’s really what I’ve been focused on. Mmm. Probably for the past nine months and it’s bearing a lot of fruit. But I don’t think I could have started there. You know, there was some groundwork that needed to be laid very similar to Maslow’s hierarchy of needs.

Grant Ingersoll: 33:43 That’s amazing. I mean, I think, you know, you hit on one of the things I’ve seen is as well as this creating contracts, you know, it’s, it’s not, in some ways the contracts like designs is also a future contract with yourself. Right. you know, by writing those down, by taking that time, I am communicating into the future. Right. And a lot of times you’re actually communicating to yourself in the future of, Hey, here’s what I thought at the time. And so it, it helps everybody just, it, it unlocks the bottlenecks because now you can communicate asynchronously and, and you can communicate across time as well, which is I think a, a really underappreciated idea in a small and fast-growing company. Right?

Caine Tighe: 34:31 Yeah. It’s, I mean it’s, it’s been really such an amazing experience that I’m grateful for. I mean, we did 9 billion searches in 2018 with less than 70 people. We’re at 40 million searches a day. Wow. 1% of the U S search market. It may not seem like a lot, but when we were sub 1 million a day, it seemed like you said, roll in this Boulder up the Hill.

And I really think that how really spending a lot of time in investing in your people, yeah, sometimes you overinvest but it’s very rare and usually on the other end, like if you identify the right people to bring into your company and you invest heavily in them, there’s, you know, there’s something on the other end of that that’s way, way greater than the amount of time you’ve invested. So it’s been an experience.

Grant Ingersoll: 35:22 That’s amazing. And then perhaps shifting gears a little bit and into kind of the here and now and forward. And I mean, I think you just kind of touched on this with, you know, you’re up against, you know, your 9 billion is a lot of searches, but you know, I mean, Google probably does that and I don’t know, 10 minutes or something like that, or an hour.

So, you know, you’re in this arms race against some really well funded behemoths and you know, barring government action around trust and all that kind of stuff, which, you know, there’s rumors of every now and then, but how do you, you know, think about that as a CTO in terms of competing you know, how do you find those arbitrage situations? How do you think about the strategy of, of being in that type of role? You know, the proverbial David and Goliath,

Caine Tighe: 36:14 Now we’re talking like, this is what I’m excited about. I’m actually, I’m prepared to talk about DuckDuckGo more than I am myself. So right. We started searching Oh eight and about two years ago. Like search was simple, right? It that go is, we’re designed to at that time, right? We always wanted to raise the standard of trust online. And the way we were doing that was through, I’m building the world’s most trusted search engine.

And then two years ago it had been just digging at us because we were making progress on this against Google and, and people care about privacy, right? Like 65% of Americans say that data privacy is the most pressing issue out of 16 different issues and more concerning than healthcare. Right? Well that was from USA today, a survey of two, 2000 adults. And, and I think that’s, that’s the market, right?

Caine Tighe: 37:15 So like it, people want this [inaudible] and well we realized as we were building the search engine was that we couldn’t protect them. People. We couldn’t raise the standard of trust online once they left the site. That was like pretty scary and we needed to solve that. So that’s when we decided to work on a seamless privacy protection beyond search.

In the last two years we worked on a solution called privacy essentials, which we launched on data privacy day, January 23rd of 18. It’s a holistic one stop shop for all your privacy, you know, all your online privacy needs, tracker blocking, better encryption will grade sites based on like how, you know, pernicious, they already are privacy and obviously there’s private search in there. And then when you look about, when you look at that and you push forward right to the future, in addition to protecting them off of your own site, like it’s very clear that, that’s not enough. You can’t just stop there.

Like, and what we’ve realized is that it’s important for us to join the regulatory. So the way in which we’ve been pursuing that is understanding better, what some people may be familiar with is do not track. You know, 23% of people have, do not track on. 41% of those people had no idea that like, it’s completely voluntary. And that like, companies don’t, these, you know, your Googles, your Facebooks, Twitters, they don’t even, they don’t even appreciate that, that value and that three-quarters of the entire people expect that that would be followed and that it should be regulated. Mmm.

So that’s, that’s like a pretty interesting and compelling story to me. And it’s what really gets me up other than making the people in our organization feel safe, is how can we make other people feel safe online. And I think we need to empower regulation with information and that narrative. So that’s kind of, I think, you know, that and amongst some potential other product lines we may think about in the future. Yeah,

Grant Ingersoll: 39:53 That’s awesome. And just for the, for everyone listening, I’m staring at my notes for this interview and Google docs and the duck duck go privacy essentials is a rating it as a D right now. So [inaudible] you get this nice letter grade that is almost always a C uh for, for many sites unfortunately it was. So I can tell just in the way you’re talking about that this is,

Grant Ingersoll: 40:19 This has become quite a passion. Was this always a passion for you and you know, I’m so often in career advice, Oh, follow your passion, which I actually think is kind of, BS, it’s more find your passion and then go for it. Because especially in early on in your career, you just often don’t even know what you’re passionate about yet. I mean, good on you if you do, but you know, so how did that come about for you? Is it just purely out of working at DuckDuckGo go or were there inklings of it earlier on?

Caine Tighe: 40:50 I can’t say that I went into DuckDuckGo like with statistics on how many people or cared about Pew research on four point 5,000 respondents and committed some of these things. Do memory, you know, it’s, I think what I’ve always cared about is freedom. You know, I I committed contributed a lot to open source and when I was younger and, and I think privacy [inaudible] [inaudible] is a part, it’s a, it’s a fundamental human right and it’s [inaudible] you shouldn’t, when you’re observed, you may not have the freedom of thought and you’re typing your intentions and your thoughts into a search engine.

Caine Tighe: 41:40 And so I don’t, I think I was just kind of like, wow, games, really smart games, really cool. And like, wow, this is like a search engine and there’s an unlimited amount of technological playground for me to like contribute to. Then, you know, like I said, I was immature and young and, and I think as I kind of have grown with the company, as you said, I’ve come to realize that like this is much bigger. And like the implications of, you know, building of a vision and trying to take responsibility for raising the standard of trust online is something I really believe in. Yeah. So I guess I, you know, I have many passions, but this one’s really kind of got its teeth in right now.

Grant Ingersoll: 42:26 Yeah, that’s very cool. I mean, I, like I said, I love that, that you, you know, like sometimes it just happens later. You know, you don’t always have to know. And, and I think for our listeners out there, that’s a really key thing to remember and, and your career is you don’t always have to know.

And I often just in my own, I look at it as my career has been guided exploration, right? I kind of have an idea that I want to go in that general direction, but if I see something interesting over on the side, and I think you hinted at this, is especially in this field of technology, there’s interesting things everywhere. And so just get involved in, then you can, Oh Hey, let me go look over on the side. Maybe it’s just a day trip. Maybe it’s your lifelong career.

Caine Tighe: 43:11 Yeah, I mean I think that’s like, that’s, that’s a great way to put it. I mean, to me it’s, you know, I really believe in making your own luck and luck is preparation, meeting opportunity. I don’t know who said that, but I’ve always lived by that. And I think my passions have like played off of one another.

Know the computer was an obvious passion. And I, I’ve kind of like change that into, I’m more passionate about frankly, the cultural side of our company now, even though I do a lot of technology. Mmm. And then, you know, how that making a trustworthy company, because if you make a trustworthy company, the way that they are forensically making decisions is know in the service of raising the standard of trust online and how, again, all of those things feed off of one another. I think you’re exactly right. Like you’ll find it if you are honest.

Grant Ingersoll: 44:02 Yeah, no, that’s great. And that, and perhaps that’s a good,utie in or segue into to my last question. And,uI wanna I pretty much ask in some form of every, every guest,uwhich is, you know, Hey, so if somebody wants to get into this field around trust and privacy and perhaps we’ll throw security in there,uyou know, what do you recommend? What is, what are some, some keys that you found helpful in terms of somebody who wants to gain the technical to get up to speed on,uon these issues?

Caine Tighe: 44:37 Sure. Mmm. So I think that security is its own thing. You know, security, engineering and, and all of that is, it’s very difficult, very worthy work. And I think we use a lot of that work. And I think if you want to get, that’s a turtles all the way down type of deal security all the way down to cipher suites and like how the math works and there’s a lot of really amazing and fun stuff in there. Mmm.

So for that, my recommendation, Mmm. Would be to just go read and get involved in configure servers and understand, I understand to the best of your, to, to understand it the best of your ability, how to implement security protocols. Why, what’s the difference between assault and a nonce? Like why do the, why does that matter? Does it matter? Mmm. And, and that’s just a practice while practice, practice, practice, CS way. Privacy I think is, Mmm. From a technical perspective, it can be easy. It’s like that which you do not collect.

Grant Ingersoll: 45:49 Yeah. But at the same time, you also still, you know, need the, you know, as my, a CEO loves to say, we’re, we’re still here to conduct commerce, right. So you’ve got to find a, you’ve got to find a way that, that you’re still you know, able to make money at the end of the day. And then, you know, and in your space, of course, there is a way, as you guys have proven to do that, which is, which is really cool hits that, you know, sometimes I think one of the things you’re really getting at is sometimes you just have to think differently about [inaudible].

Caine Tighe: 46:19 I mean, our implementations are very complicated because of our privacy constraints. Mmm, okay. Even we, you know, developing noninvasive feedback techniques to make sure that the products are correct, you know, that they’re engaging. Like there’s a lot of amazing work that you can do there.

I think what it comes down to with the privacy stuff is you need to really understand and do the intellectual labor to ensure that the software that you’re developing is doing what you’re intending it to do with respect to the user and respecting the user. You know, I have this phrase, Mmm. Where you know, that’s stolen straight out of Tron, which is, you know, we fight for the user. And I think that is how I view privacy within DuckDuckGo is doing the intellectual labor to understand where to fight and why and what, where the line is.

Caine Tighe: 47:19 Because there are so many lines with privacy that that exists that are not the same as with security. Security is like, can somebody like bang on this, you know, implementation and like break into it. Privacy is like how you, like you said, how you conduct a business. And I think yeah, if you want to get into the privacy space, it’s a lot less configuring engine ops or Apache or whatever and go into SSL labs and figuring out what your server is doing.

And it’s a lot more of thinking about how you might run a service and what you would collect and what you wouldn’t collect and taking a least collection model. Mmm. So I dunno if that helps, but there’s a lot of intellectual labor there for, you know, make ethics, deciding what you’re going to do.

Grant Ingersoll: 48:15 That makes sense. And so maybe I lied and I’ll ask for one more question, which is, you know, now that you kind of reflect back, you had a lot of good nuggets in there and super thankful for you joining me. But you know, perhaps just if you could sum up kind of your best career advice as you as reflect back, other than having a [inaudible] awesome mom, by the way. You know, how do you, how would you, you know, what would you recommend for people just as they go forward into their career?

Caine Tighe: 48:42 My number one piece of recommendation, which was obvious from when you, I said I might have to answer that question, was understand how you spend your time period. It has changed. Like it not only has that changed my life, it has changed everybody’s life that I’ve been involved in. If someone’s unhappy, I just literally started digging into how they spend their time.

If they hate it, it’s like walk me through Monday, walk me through Tuesday, walk me through Wednesday. Then you just keep exhaustively looking at how you spend your time. And if you understand how you spend your time, it’ll get you through the things that you don’t like, like traffic on the way to work. Mmm. If you at least understand it you can really have a better career. And make sure that I, that I mean it really is that simple. I know, I know it sounds kinda crazy, but just really understanding how you’re spending your time from a first principles perspective and not just being like, Oh, well I had to do that or whatever. Like get, write it in a spreadsheet, go crazy with it, really understand it.

Grant Ingersoll: 49:53 No, that’s, that’s awesome. And, and I think I, I don’t even know what the add on to that because I think there’s some truly Sage advice there. So I’ll just wrap up then with thank you so much, Caine, for joining me on the podcast. For our listeners, I’ll make sure to link up a number of things Caine mentioned in here are some of those books. A I to a second in particular hard thing about hard, hard things about hard things. We’ll make sure we link up duck, duck, go and some of the tools that came mentioned there, but.

Caine Tighe: 50:26 I’d also Gabe’s books. He wrote traction and then he just recently released a mental models book, which is pretty amazing as well. He wrote that with his wife so I can share those with you after and I would highly recommend that is when I kind of got those over the past 10 years for free.

Grant Ingersoll: 50:44 Awesome. That’s a, that’s so cool. And that killer advisor finding a good mentor I think is, is so critical. So Caine, thank you so much for joining me today. Likewise. 

Caine Tighe: Thanks a lot grant

Grant Ingersoll: 51:01 Thank you. As always to our listeners for taking the time to listen. If you’d like to show, we’d love for you to subscribe on Apple podcasts or whatever your favorite podcast app is. You can also visit us at develomentor.com to hear older episodes as well as find other content on careers in technology. Most importantly, if you like the show, please tell your friends. Referrals are the lifeblood of any podcast. If you have any feedback on this episode or any episode where you’d like to be a guest, drop us an email at [email protected] Finally, we here at Develomentor hope that each and each and every episode helps you move that one step closer to finding your path

Outro: 52:00 [Inaudible].

Additional Resources

Selected Links from the episode:
Circle of Competence – a concept by Warren Buffet and Charlie Munger

Books mentioned:
The Advantage by Patrick Lencioni
Principles by Ray Dalio
The Hard Thing about Hard Things by Ben Horowitz
Traction by Gabriel Weinberg
Super Thinking by Gabriel Weinberg

CONNECT WITH CAINE TIGHE
Twitter
Website

CONNECT WITH GRANT INGERSOLL
LinkedIn
Twitter