Avery Pennarun On Selling His College Startup To IBM And Raising $115 Million To Build A Secure Network

Avery Pennarun launched his first successful startup in college. He is now on his second tech startup, and investors have been more than eager to help fund it. The venture, Tailscale has attracted funding from top-tier investors like Accel, Heavybit, Insight Partners, and Uncork Capital.

In this episode, you will learn:

• The future of the internet (and how it may be different than you expect)
• The incredible value of reading books and surrounding yourself with advisors

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About Avery Pennarun:

Avery Pennarun didn’t set out to be a technology entrepreneur; what he really likes is coding.

But examining the trail of new products and businesses he left in my wake, he seems to fit the entrepreneur definition. Avery’s favorite thing to do is take business ideas and turn them into working hardware/software products. His favorite phase of any project is the one where nobody knows what to do and everything seems impossible. As he got older, Avery seems to be getting better at the later phases too.

Specialties: Programming (Go, Rust, Python, C, C++, x86/68k/PPC assembly, SQL, Delphi, and several others), Operating Systems (Linux, FreeBSD, MacOS, Windows, iOS, Android), low-level driver design, network protocol design, logs processing, embedded systems, APIs, installers/uninstallers, user interfaces, and product strategy.

Avery is also good at marketing poetry, recruitment, team building, impressing venture capitalists, creating new business processes, technical support, and even some sales.

Connect with Avery Pennarun:

• Crunchbase
• LinkedIn
• Facebook

Read the Full Transcription of the Interview:

Alejandro: Already hello everyone and welcome to the deal maker show. So today. We have a really exciting founder. You know a founder that is a repeated founder so we’re gonna be really learning here about the full cycle about building scaling financing and exiting. And obviously now you know he has a company that is saying a rocket ship. So I guess without furtherdo. Let’s welcome our guest today Avery Pennarun: Pinarum welcome to the show. So originally borning ontario.

Avery Pennarun: Hello Thanks for having me.

Alejandro: There in Canada so give us a little bit of our walkthrough memory lane. How was life growing up.

Avery Pennarun: Life growing up. Well I was born in Thunder Bay Ontario which is is pretty far north and it’s about a 4 hour drive from anywhere even significantly sized so it was quiet I had a at a quiet upbringing in the outskirts of this. City. So. There was lots of nature and stuff like that and I do like nature but I’ve I’ve learned since leaving there that I also like big cities. So I like to go back and forth.

Alejandro: So with all the nature and everything. How do you get into computers.

Avery Pennarun: Well, that’s that’s the thing with all those nature and everything there was not that much to do so we had a computer and I got pretty into that as soon as what my dad bought brought home a modem when I was maybe None ears old I got really interested in this ability to like meet people and communicate with people that I otherwise would never be able to meet because it was you know a 10 minute walk down the street just to find anybody. Um, so yeah, online is was was a pretty big change for me.

Alejandro: Now you know in your case you went on and and you studied engineering and right a time where you were in school I mean you decided you know there was a cool project that you wanted to do with with a fellow co-founder there. You know you thought it was just going to be a project but it ended up taking a live of its own. So So walk us through that journey.

Avery Pennarun: Sure? Well I went to the university of Waterloo in Waterloo Ontario None thing a lot of people don’t know about the university of Waterloo is that they have this co-op program where unlike a regular internship at Waterloo you do. four months of school and then four months of work and four months of school and four months of work so by the time you graduated you usually had about None different jobs so that you have a much better idea of what you want to do when you grow up and so one of the things me and my roommate decided to do is for None of those four month terms we thought okay, well maybe we want to be an entrepreneur when we grow up. So why don’t we try starting a company and it’ll be fine because we’ll probably screw up a whole bunch of stuff but we’ll just do it for four months and see how it goes and so what we did sort of leading up to that four months is we we built a product which happened to be a a network appliance server that you could use to share your internet connection. This was in the early two thousand s late 1990 s um so the people were still using modems and stuff and I’d observed that a bunch of companies would have maybe None computer in a corner with a modem and people would line up everyone in the office 1 by 1 to try get online and check their email and we knew this this linux thing. Was available now and you could use that to share a modem across everybody in the in the office so they wouldn’t have to line up. They could just check their email from their computer so we built a little product to make that easier and by the time our four month period started. The product was ready and it was time to start selling it so we sold it to a few people. We were pretty proud of ourselves because we could build this box for $1000 in parts and sell it for $2000 um, and then we were going to try to just shut down the company at the end of the four months but what we learned is that people like this product so much that they kept phoning us. Um. And and wanting you know, recommending it to their friends who would then phone us and say hey I want to buy this device and as starving students when you could buy something for a thousand and sell it for 2000. It was hard to turn that down. So the company sort of got a little bit out of control after that. Um, at one point I got called out of an exam that I was writing because someone has an urgent tech support question. And we realized things were getting ah out of control so we brought in a few other people who could do none line technical support. Next thing you know there was http://a.com crash we were graduating we decided it was time to expand the company so we ended up raising some money right? after the dot com crash which is a little bit scary. And eventually you know to make a super long story short. All this viral growth ended up and in us so selling to Ibm and in 2008.

Alejandro: And what was it like to run a company after the crash. What was that like.

Avery Pennarun: So I think the most interesting thing about that. Obviously it was hard to raise money. Everybody was super super conservative about investing in tech companies right? after the dot com crash being a canadian at that time was actually kind of a benefit because canadians are always a little bit conservative so the investors in Canada had. Not invested on the way up in the dot com thing because they thought it was too crazy but then they still had money left after the big dot com crash unlike a lot of the us investors who who they really broke the bank and so we got canadian investors. The downside is canadian investors can be a little bit. Um I don’t know what the word is. Old school or or hesitant or you know the numbers are always smaller and they always. They’re always pushing you for sort of more old school financial metrics even when it’s not that relevant this is especially true back then I think canadian investors have come a long way in the last twenty years but it it was tough raising money and it was. We raised less money than a comparable company would have raised if the market hadn’t been under the same conditions but the good news is we learned how to be really really frugal with that money which is an important lesson because a lot of companies who raised a lot more money than us 2 years earlier were already bankrupt by the time we were talking about working because they just never learned how to. How to operate in a ah more constrained environment.

Alejandro: And tell us about the process with Ibm because obviously you know incredible a journey and outcome first a company first exit I mean that’s obviously not the norm and and more importantly, being in Canada where probably the startup ecosystem was almost nonexistent. So at what point does Ibm you know, come knocking and and what was that like.

Avery Pennarun: So that was that that was a really interesting experience. So this none product it grew from just a modem sharing product to by that time we had added a bunch of features the most important feature that we added was what we called a virtual server so you could run. I guess nowadays you just call it a container it was before docker showed up but you could take this network appliance that we sold you insert a Cd and it would because people use cds back then because the internet was still slow. So you’d insert the Cd and it would install a linux environment. Including an application directly on to this appliance and get it running in in sort of None nutes instead of having to go through a complicated installation process. Um and much like containers today. It was sort of revolutionary because you weren’t messing around with all the other environment stuff on your computer. You just put in the app and the app would just work no matter what. And it was on this physical appliance so it was really good for deploying things to small businesses that otherwise would have been hard to deploy to small businesses. 1 of the things that up until toward the end of our cycle with that company. We hadn’t really figured out was that it’s better to focus on something really tight and small. And appeal to a particular market really strongly than it is to make just something cool and technical. We sort of got sidetracked by a lot of tech enthusiasts who were really excited about the cool technological capabilities of our product but it’s kind of hard to make a bunch of money selling the tech enthusiasts when we implemented this virtual server feature. Created this really interesting new business development opportunity where you could work with the the vendors of apps who wanted their apps to be easier to install in a small business. Um, but didn’t have the technology to do that. So there were a couple of apps that we started working with None of them was an accounting package. Ah, that that actually went pretty well because now all of a sudden this accounting package. No longer required you to set up a windows machine and the installation process went down from like four days to 10 minutes but then another package that we started work another company. We’re working with was Ibm. We made it easy to install lotus Domino which is part of Lotus notes. And also easy to install ibm t v two and both of these packages are famously incredibly complicated to install and Ibm at that time was at that time maybe 2006 or so was still kind of bitter about Microsoft stealing dos from them. And we’re really worried about Microsoft Outlook in exchange taking over everything so they really wanted to try to get Microsoft our sorry lotus notes and domino into smaller businesses and tailski are sorry excuse me our company was the the pathway to make that possible so they got really excited about it at none we were working together.

Avery Pennarun: And then they decided they didn’t want competitors to have the same capability so they ended up buying us just for that one feature.

Alejandro: So wow I mean in in the double digit None So I mean quite a an outcome for for someone of your age. How old were you at that point.

Avery Pennarun: At that point, let me let me count for second I was in my late twenty s I Guess at that time Obviously I didn’t make all that money our investors took back some of it but it was It was a reasonably good exit.

Alejandro: That’s incredible. That’s incredible. Yeah, no kidding now if for you what what happened next after the exit.

Avery Pennarun: After that I I went into the banking industry for a little while I knew someone in the the banking world. Um, and they were trying to commercialize their internal banking software that they developed for themselves and try to sell it to other banks. Ah, and and he wanted me to help them build a tech company out of that that was a really interesting experience. But unfortunately it was cut short by the financial disaster in 2008 2009 that turned out to be the worst possible time to be trying to sell things to banks. And so we decided not to do that. That’s when I ended up moving on to work at Google for a few years

Alejandro: And in Google you were for None ars or so now you know that’s quite a lot of years I guess say up until then you know you you had done more of your own thing and but I guess that working for such ah an amazing you know much bigger company like Google you know, perhaps that gave you. The the perspective and visibility into also how a bigger company operates. So I guess what did you learn from the experience at Google.

Avery Pennarun: But it’s funny I remember my first year at Google I was because I was so accustomed to doing things on my own I was pretty sure that it wasn’t going to work out. They made me a good offer I’m like okay I can’t turn down the offer. But. I didn’t spend my signing bonus for the whole first twelve months because if you quit during the first twelve months you have to give back a prorated amount of your signing bonus and I’m like as no way I’m going to last twelve months of this place I better. Just keep this money in the bank and then I ended up working there for 7 years which was as much of a surprise to me as it was to all of my friends and probably people at Google. But the yeah the experience was really interesting just seeing how a big successful really megacorporation operates now Google is a pretty unique, big successful megacorporation. So it’s not exactly like working at other big companies but certainly having all the structures in place. It was very interesting. What am i. My first manager is there I asked him like is it does it make it harder trying to do do things when there’s basically an infinite amount of money available because I’m only used to doing things with a limited amount of money available and what he said to me was. You’ve heard about trying to do more with less You’re very familiar with doing more with less and at Google what you have to do is set your sites on doing much more with more and it’s it’s a different optimization goal Google doesn’t need you to do regular amounts of stuff because it won’t make a blip in the bottom line Google needs you to swing for the absolute. Stratosphere um, and you can spend a bunch of money doing it because they have a lot of money but it needs to be big successes. They’re not interested in small successes and that was a really so big change in in my outler.

Alejandro: I hear you now at Google you did you did spend quite a bit of time I mean the question that comes to mind now is so you did your none company. You know writing university you had a fantastic success. You know, successful outcome and. Why did it take you so long to launch the next company because as they say once an entrepreneur always an entrepreneur, especially if you had a ah positive a positive outcome. So what took took you so long.

Avery Pennarun: So before I joined Google I had I actually had an idea for my last next startup already I was going to make wi-fi routers and this was um, this was none or so and wi-fi routers were were quite bad at the time they’re still kind of bad. But I had a long list of things that I thought should be better about wi-fi writers and I noticed like my first startup we made linuxbased appliances for network sharing. It’s a lot like you know it took a thousand dollars in proponents like a full size computer to do what by 2010? you could build. You could just buy a linkxys router from the store for $80 and it did pretty much the same stuff. Plus it had wi-fi in it. But these routers were not that good. They were missing a bunch of stuff that I figured ought to be in these products but when I did the market analysis I’m like okay from an engineering point of view. We can build a way better router than any of these other routers that are on the market and we can do it for a reasonable price. From a marketing point of view I don’t know how to get these things into people’s hands because nowadays the way people get wi-fi routers and that was true in 2010 and it’s even more true now is that your isp provides None to you right? They hook up your internet and they drop it in your apartment and isps are not buying. Routers because they’re so good or because they solve the customer s problem. They buy routers entirely because you can buy. You can get a whole bunch of them on mass and mass mass control them right? And that’s not the best way for people to get the best experience but I couldn’t think of a way to go to market and sort of overcome that problem and I think sort of my. Yeah I decided not to start the startup because I couldn’t figure it out and I think based on all of the there were a bunch of wifire road or startups starting around none and going to around twenty twenty ish and I think they all ran into that problem and most of them failed for that reason. So I think that was sort of borne out. Reason I ended up joining Google was one of my friends gave me a hint that this Google fiber thing was coming along and Google Fiber was going to be an isp but they were going to be a different kind of isp that cared about user experience a lot more and so what I ended up doing at Google was working on wi-fi routers as part of an isp. Where we could actually focus specifically on making sure people had a really good experience and making sure that the customer support costs were really low, but the channel to getting to market was somebody else’s problem which was the Isb. So I got pulled in because it was the project I wanted to do anyway. Um.

Alejandro: So got it.

Avery Pennarun: And we were doing pretty well up until sort of and this is one of the problems with with Google they sort of lost interest all of a sudden if in Google fiber and then my project sort of got stopped.

Alejandro: Okay, so then at what point does say you know tail scale. The idea you know, really come knocking and and why did you think it was a good idea to give your notice and and go after it.

Avery Pennarun: So I give my notice I guess when they they paused Google Fiber Development I didn’t actually know what I was going to do next at that time. So I took I guess it turned out to be about six months off just just relaxing and playing video games trying to decide what I wanted to do next. And one of the things I was sort of angry about at the time is like well look Google that got this short attention span and he ties back to this like trying to do much more with more it turns out like doing much more with more is not really what I’m good at I’m actually better at doing more with less and in fact there’s a lot of people out there who need to do more with less and Google like being inside Google you lose touch with that kind of people and so tailscale is a bit of a joke. It’s the the opposite of internet scale the vast majority of problems faced by the vast majority of developers in the world are nothing like Google’s problems right? They’re much more like look I’ve got one computer my entire ad base can fit on this computer. It’ll scale to none users no problem on this one computer but I really need to take care of this one computer and I need to get rid of all this overhead created by the computer so I can actually solve the problem and so tailscale is sort of the motivation is a little bit of a. A reaction to the fact that the whole world by then had been copying Google’s techniques to scale things up to extremely high scale when not every problem needs to be scaled that much. And so tailscale is all about like let’s solve like make the easy problems easy because other people are making the hard problems possible. Ah, that’s that’s a good question. It’s it’s a little complicated to answer. It’s it’s ah it’s a combination of None or 3 different business models that works really well together.

Alejandro: So then how do you guys make money at tellscale. What’s the business model.

Avery Pennarun: Ah there’s a really great talk from ah Alan gross who who titles his talk gtm 3.0 but the the general concept is this sort of hybrid model. So individuals. Developers usually at home adopt tailscale to play with it because they’ve got raspberry pis or home automation systems or 3 d printers or whatever they just want to connect their devices to each other but they get really excited about it then they tell their friends and then you know their friends use it and they get excited so you have this huge word of mouth growth but all of this is on the free plan. Individuals we don’t try to extract money from individuals but some of these developers will then bring it to work and get value from the same kind of connectivity tool but at work and then they will tell their friends at work and eventually you know the the value they’re getting from a commercial point of view is very different than the kind of value they get as individuals at home. And the value is definitely worth paying for so at work they’ll pay the pay the monthly fee and then interestingly some fraction of those people. Um, get so excited about using tailscale on their development team at work that they go to the it team and say look on the development side. We’ve got this amazing connectivity tool called tailscale it’s solving all our problems. For the rest of the company we have this terrible vpn that’s twenty plus years old that everybody hates you should ditch the terrible vpn and you should put tailscale across the whole company instead and then I won’t have to use None tools and everybody else will benefit from this wonderful tool that we found and it’s really an interesting business model because. It flips from the being the sort of bottom-up product-led growth adoption of individuals 1 by 1 to now you’re talking to the Cio or the Vp of engineering or the Cto and saying like hey we’re going to rule something out across the whole company. Ah, it’s a top-down sale. They want to buy a bunch a whole bunch of licenses at once and roll out a whole bunch at once. So if you look at the adoption curve it sort of stops starts off like a few people a few people a few people and then jump suddenly now you’ve added a None seats or something like that and that’s where most of the real money is and the the vpn market is tens of billions of dollars a year. And most vpns that everybody is using nowadays are terrible.

Alejandro: Very cool now. How did you go about putting the band together for the company.

Avery Pennarun: Ah, so we started off with three cofounders. there was me there was a person I met at Google doing interestingly because we both had been working on high scale logs processing me for the Google fiber service and him for a different service internally. Um, we kind of hit it off from a technical point of view and then another one of my friends who actually worked with me who was one part one of my classmates at the university of Waterloo and also ended up working with me at my first startup he had just gotten out of a. Another startup that he was working on at the time and was available and he said like hey it would be great to work with you again. You have any good ideas and I’m like well as a matter of fact I do have a good idea. Um, so yeah, the band came together there and just like from all of the contacts that the 3 of us had made in the preceding. You know, 20 years of our careers. Um, it was. Relatively easy to fill the team with some um, amazing people that we sort of met along the way because a lot of people this this idea of like why don’t we just do things the easy way. Why don’t we make a product that makes it possible for everybody to do things the easy way really resonated with a certain group of especially engineers.

Alejandro: Nice now in terms of the financing I mean you guys have raised quite a bit of money for this business. How much capital have you guys raised for tailscale.

Avery Pennarun: Total capital raised is a hundred and fifteen million usd

Alejandro: Now in your case you raise quite a bit more than what you needed ah because you saw that there was going to be some financial turmoil. So how did you think this through what was the thought process and.

Avery Pennarun: Sure well we raised 3 rounds so far. None one was 3000000 in our seed round then we raised 12000000 series a and then we raised $100000000 series b about a year and a half after that companies only been around about 3 years

Alejandro: And how do you go about that.

Avery Pennarun: Ah, so the market is is clearly or up until very recently was much more exuberant than it was in 2001 when I started my first company. Um the the series. So the none I think was you know we raised it because we wanted to hire some people that wanted to work with us but couldn’t do it for free. Um, we could have lasted pretty long on that $3000000 but when the series um the series a basically came together on its own because several investors saw how things were going just with our initial launch and wanted to get in and I remember. At 1 point because I was refusing meetings with investors because like guys we have $3000000 I don’t need more money but someone came to one of our existing investors and said like Avery Pennarun: or said can you pass along a message to Avery Pennarun: name your terms name your price we want in and I’m like okay well anybody that desperate I shouldn’t talk to them because I don’t want to work with. Investors who are that desperate so like close that one down but then within a couple weeks. There were 3 other investors who came in and said like can you tell Avery Pennarun: the same thing I I want it also and our investors are like okay Avery Pennarun: this is what you call a global maximum. You’re never going to get a better deal than this you should just do the series a right now if you’re ever planning to do a series a and I’m like all right? Well I guess. Sooner earlier later. We’re going to do a series a so we raised the series a but one of the bits of advice we got and this was in 2020? Um, one of the bits of advice we got is like don’t push your valuation too hard. You can hard. You can start a bidding more right now they all said name your price you know. Presumably There’s an actual limit to that you can’t actually name your price to any number you want but they’ll go pretty high. They’ll probably go higher than they should but be careful because if you set the valuation too high. It’s going to be hard to raise a series b so I took that advice to heart and we set a cap for how high we were going to let the valuation go at the series. A.

Alejandro: Now.

Avery Pennarun: And then we instantly hit that cap. Everybody’s like okay well I cap super reasonable I’ll buy in at that and then we had to select our investors based on different criteria and it was actually pretty difficult because the investors who had gotten through this gate so far. Um, were all really good and so there was ah a little bit of a. You know they called this success problem but we actually struggled quite a bit to choose which investor we wanted to lead our series. A we did that and then you know as time went on then the motivation for raising our series b was quite different. We still hadn’t spent. Most of the money from our seed or series a I remember thinking as we were raising the series b that we had finally just finished spending our initial 3000000 from the seed and had barely begun digging into the None from our series a but we started getting advice from our investors in our network of advisors like hey the market. Has been really great, but it’s too great. This can’t go on forever and your numbers are looking super good right now. Are you confident that your numbers are going to keep looking that super great a year from now or should you take advantage of the good economy and your good statistics and they strongly recommended we do the latter. And and things were looking kind of shaky and so on the serious b we actually intentionally took the opposite strategy. We’re like okay things are great right now there’s no way the economy is going to keep going like this forever and it turned out that was a much more accurate prediction than I would normally be able to make so we got super lucky on the timing. Um, yeah, but yeah, with that one. We intentionally said okay, we’re not going to cap the valuation. We’re just going to go to raise a bunch of money and I sort of got taught. We were originally thinking of raising $30000000 because that would have been plenty but our investors are like well what if something happens.

Alejandro: They’re no kidding, no kidding basic timing.

Avery Pennarun: $30000000 might you know if you aim for a twenty twenty four month runway we might be still at the bottom of the market by the time that twenty four months runs out so’re like okay well why don’t we raise like 70000000. It’s like that’ll that’ll be ah you know that’ll last us for sure through the 2 years if if there’s a downturn. Ah. But then you I was talking to some other people. It’s like well okay, everybody’s going to be raising 70000000 I bet you’ll get a bunch of press if you raise None because it’s the magic 3 digits right? and I’m like okay well in some sense. This is a dumb thing to do and I’m I’m canadians who are especially conservative. It’s like there’s no way I need a hundred million dollars um

Alejandro: Yeah, yeah.

Avery Pennarun: But I think there’s there’s something to be said for just making a bunch of people angry at how much money you can raise for this this you know at the time None year old company. Um, and I think that will get people’s attention in the right Way. So. You know we we started talking about raising $100000000 and and again as with the series. A. There were a bunch of people interested and of course it was. There was some various you know disagreements about what the maximum valuation should be in staff but we ended up taking. Not not basing entirely on the valuation but choosing the best possible partners with a good valuation I think we did pretty great but it was intentionally so we can last out, whatever kind of weird economic downturns Happened. So we’re We’re intentionally not running out to spend this money as fast as we possibly can the goal for me was like let’s. Let’s make sure this company is not going to die no matter what and in the meantime if other people are getting tight on money because the economy starts going badly. That’s better for Us. We’ll be able to spend our way through the downturn instead of cutting our way through the downturn.

Alejandro: That’s amazing now for the people that are listening to get an idea of the scope and size of tail tailscale today I mean anything that you can share in terms of number of employees or anything else that you’re comfortable with.

Avery Pennarun: Ah, right now we are around 40 employees.

Alejandro: That’s incredible. Wow what? Ah what an output and for for it for the size that’s incredible now. Imagine you go to sleep tonight Avery Pennarun: and you wake up in a world where the vision of tellscale is fully realized what does that world look like.

Avery Pennarun: So when we write down our vision statement. The the super short version is is is the new internet. So the risk of getting a little bit technical um I remember back in 9094, you could buy a windows computer and it did not have Tcpip on it. Right? Like the internet was a thing that not everybody had and I remember you had to like add on this tool called trumpet winsockck to to add internet support to your windows machine and then windows 95 came along and added Tcpip to it. It’s fast forward to now twenty five plus years later even if you buy a watch and it doesn’t have tcp ip on it. You’re like what’s wrong with this watch. It doesn’t do anything. It’s broken right? The internet is everywhere every single electronic device now has got internet stuff in it. Um, and that’s how you know in that time span we went from like you can you don’t really care about the internet that much. It’s a new interesting thing. It’s everywhere but the internet itself has a bunch of problems with it that have sort of evolved over time we can talk about that if if you want but like the you know the cloud is partly a symptom of the fact that you can’t even connect to your own devices anymore right? like I could have a server at home that can do everything I need. But if I’m not at home I can’t use it right? It’s this weird problem if I instead take the same stuff and rent time in the cloud then I can access it when I’m not at home. There’s a bunch of security problems. But at least I can access it run and not at home. So I think the future is a little bit. You can sort of picture it as a pendulum back of the 1960 s there were Ibm mainframes. Microsoft came along and pulled things toward the pc now everybody’s got their own computers. Ah excuse me. But now we’re in the world of like mobile devices in the cloud. We’ve all got our own computers. Our mobile devices are more powerful than the pcs we had ten years ago but our mobile devices are useless without the cloud if you took away the cloud these super fancy supercomputers could do nothing right? I think things are going to shift a little bit back the other way I think these computers that we hold in our pockets can do things without needing the cloud without having to pay rent to the Google Amazon Microsoft of the world. And I think tailscale can make that possible I think tailscale could be the next thing that like 30 years from now. It would be weird not to have it on your computer because like the internet’s broken if you don’t have it.

Alejandro: That’s amazing now we’re talking here about the future. So let’s talk about the present and let’s talk about the past. Let’s see if I was to put you into a time machine and I was able to bring you back to bring you back to perhaps Waterloo when you were you know, studying engineering and. Let’s say you had the opportunity of speaking with that younger self and given that what the giving that None younger self a piece of advice before launching a business. What would that be and why given what you know now after you know having run None companies and.

Avery Pennarun: All right I guess I give myself probably None interlocking bits of advice that would have completely changed my career trajectory for the better. 1 of them is whatever it is. You’re trying to do when you start a company somebody has done this before there’s somebody out there. Who knows how to do this better than you can build it from none principles if you can find that person and ask them for advice even if it’s for just 1 hour it can it can completely stop you from making horrific mistakes that are going to set you back by years. And 1 of the things we’ve been doing with tailscale that I didn’t do in my first company is we have an extensive network of advisors. But I ask for advice on all kinds of things and most of the time the advice is like relatively obvious and nothing special but every now and then once every month or two I get this like brilliant nugget of advice that I would never have guessed that. Avoids a huge problem that I was about to create for myself like the difference between success and failure can be like None little bit of advice that you get from somebody so you need to go out and look for that advice. No matter how smart you are you think you are and I thought I was pretty smart back then ah the next bit of advice is actually a very specific instance of that this book called crossing the chasm. Which I really love because it is basically the story of my first company and it was given to me by None of the investors in my first company who said like Avery Pennarun: I’ve been thinking about your company a lot I just read this book this describes everything you’ve done wrong. Strategically if you had not made the mistakes that this book lays out your company would be None times or None times more successful. And I read the book and I’m like crap. It’s absolutely true. Everything in this book I mean every chapter is a lot of people think you should do this. But if you do this then this will happen and you should do this instead every single chapter. Oh I did think I should do that I did do that and that is what happened and crap that is what I should do instead and. When we by the time we sold to Ibm I have been putting putting the advice in that book into practice for a couple of years and it completely changed the trajectory trajectory of my company right? The reason we could exit. Ibm the reason we could build these partnerships with application vendors was because of following the strategy in that book so with tailscale twenty years later I’m using the advice in that book and it is working out like a lot of the stuff that’s working great at tailscale is just because I read it in a book and it you know it’s almost embarrassing to say that but I’m absolutely certain like this is this is a smart book by a smart person and everybody should read it if they’re starting a tech company.

Alejandro: I Love it now for the people that are listening Avery Pennarun:. What is the best way for them to reach out to say hi.

Avery Pennarun: I’m on Twitter a lot so you can find me on Twitter at appnmoir which I imagine will show up in the description of this podcast. Um, you can also email me. Ah, for’re using tailscale. You can feel free to email support at tailscale. We. We answer all support requests whether for paying customers or non-paying customers which is a thing that we place or we value highly being able to give everybody support regardless of payment. And I’ve also been a blog app in word ca where I write about technical staff and business stuff.

Alejandro: So amazing. Well heyber. Thank you? So so much for being on the dealmaker show. It has been an honor to have you with us today.

Avery Pennarun: Thank you, It’s great.

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