Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch FF 016: Chad Fowler, CTO @ Wunderlist, App Of The Year 2013 About this episode To win a signed copy of Venture Deals by Brad Feld, click the link below and like our Facebook page and you will be entered into the competition. https://www.facebook.com/The-Twenty-Minute-VC-769935093077190/timeline/ Chad Fowler is the CTO at 6Wunderkinder (acquired by Microsoft), the company behind the wildly successful Wunderlist, previously cited by Michael Treskow and Mattias Ljungman on the show as their must have productivity app. Prior to 6Wunderkinder, Chad was the Senior VP of technology of the daily deals site, Living Social and before that we was CTO at InfoEther, a Ruby and Ruby-On-Rails consultancy firm. Fowler is also the host and organiser of numerous tech conferences and wrote "The Passionate Programmer", a career guide for software developers. In Today's Episode You Will Learn: 1.) Where did it all begin for Chad and how did he make the move from his musician dreams to CTO of tech startups? 2.) As an American, working in Europe, how does Europe's tech community compare to the US? 3.) Wunderlist was the App of the Year, what does Chad believes makes it so special? 4.) Is there more to go in improving the consumer feel of enterprise software? 5.) How did Chad go about creating a product with such habit forming ability? 6.) Question from Carolina Brochado @ Atomico: What is it like moving from a small manned startup to a giant corporation like Microsoft? Items Mentioned in Today's Show: Chad's Fave Book: The E Myth Revisited by Michael Gerber As always you can follow Harry, The Twenty Minute VC and Chad on Twitter here! If you would like to see a more colourful side of Harry with many a mojito session, you can follow him on Instagram here!
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? This is the 20 Minute VC with your host Harry Stebbings and for this very special episode of Founder's Friday, I'm delighted to welcome an incredible entrepreneur in the form of Chad Fowler. Chad is the CTO at Wunderkinda, the brains behind the wildly successful productivity app Wunderlist, previously cited by previous guests Michael Tresco of Axel and Matthias Looman of Atomico as their must-have productivity app. And prior to joining Wunderkinda, Chad was Senior VP of Technology of the daily deals site Living Social and before that he was Chief Technology Officer at InfoEva, a Ruby and Ruby on Rails consultancy service.
0:41 Harry Stebbings? Fowler is also the host and organizer of numerous tech conferences and wrote The Passionate Programmer, a career guide for software developers. But before we hear Chad's amazing story today, if you listened to our episode with Kamal, you will know that Brad Feld has offered an amazing prize for the listeners of the 20 Minute VC. So for your chance to win a signed copy of Venture Deals, the bible of venture capital, all you have to do is click the link below and like our Facebook page. If you are thinking, I did the tweet last time in Kamal's episode, so I'm already entered, would you like to improve your chances? If you would, both the tweet and the Facebook page will ensure that you are prioritized.
1:22 Harry Stebbings? So make sure you increase your chances and tweet the previous link and like the Facebook page. Finally, are you a small business owner or entrepreneur with potential intellectual property? If so, ensure that your IP is properly protected by calling my dear friend Chris at Vidar Law on 312 895 4993 or visit Vidar's website on www.vidarlaw.com. They will help you with everything from copyrights to trademarks to patents. They're absolutely awesome guys, so definitely check them out. Thank you so much and we will now delve into this incredible episode with Chad Fowler. So without further ado, it is time for me to shut up. Chad Fowler, the floor is yours.
2:13 Speaker 01 You have now arrived at your destination.
2:16 Harry Stebbings? Well Chad, welcome to this very special episode of the 20 Minute VC. It's absolutely fantastic to have you on the show. Thank you so much for joining us.
2:24 Speaker 02 And thank you for asking me.
2:26 Harry Stebbings? Can you kick us off today by giving us a little snapshot of your past and providing a little insight into your career before Wunderkinda? And how the Wunderlist job came about?
2:36 Speaker 02 Okay, sure. I have a somewhat long history now, relative to most of the people that I work with these days, it seems, in technology. I came into technology via music and the connection there makes absolutely no sense, other than I was really into video games and wanted to learn how they worked. And so therefore discovered a passion that was similar to that that I had for writing music and performing music. Which led me to sort of leave my music career to rot, or maybe put on hold, I like to think of it.
3:14 Harry Stebbings? Temporarily paused.
3:15 Speaker 02 Yeah, temporarily for 20 years so far, on pause. But I did kind of come into technology with the same mindset that one would approach music, which is, you know, you don't you don't become a musician to get a good job. That would be really stupid. Maybe some people do, but they're not very intelligent if they do. You do it because you think you can bring something special to it. And so I arrogantly entered the technology field with the same naive mindset as the kid that thought he was going to be a famous saxophonist someday, or famous rock star or something.
3:53 Speaker 02 Fast forwarding a bit, like by almost 20 years, I was most recently before Wunderlist, at Living Social in Washington DC. My company Infoether was acquired by Living Social as a talent acquisition. So we doubled the engineering team size and I came in and became VP of Engineering. I ultimately took over the entire technology team, filling in the management responsibilities for the CTO and co-founder Aaron Battalion.
4:23 Speaker 02 Uh, it was after that point, uh, after some time that I was approached by my friends in Berlin and convinced to move to Berlin and work on Wunderlist.
4:33 Harry Stebbings? And now you're in Europe. What do you believe that Europe has as a kind of competitive advantage over the US?
4:41 Speaker 02 Uh, it's kind of hard to say. Maybe there is no competitive advantage over the US and maybe that doesn't matter. Um, it used to. So, you know, it used to matter when, like, I remember going to Europe in the nineties, playing music and being completely disconnected from the rest of my world. But at this point, it's not like that anymore. It doesn't really matter where you are in the world. Uh, there are some cultural factors in, in Europe that I think we're still getting over that are a disadvantage. Europe has historically on the, in the tech industry been uh, kind of behind the United States, a little more conservative.
5:20 Speaker 02 But even that is sort of fading away. So for me, the advantage of Europe and specifically Berlin is just that it's a fabulous, very international place to be. Uh, and compared to most of the, the cities or in contrast to most of the cities in the US that have the same sort of international footprint, it is incredibly cheap to live and operate in. And that's not a Europe-wide advantage, but that is something very special about Berlin itself.
5:46 Harry Stebbings? Would you say then Berlin is a great place to start a startup at the moment?
5:50 Speaker 02 Oh, absolutely. Yeah. And, and in fact, it's a, it starts by being just a wonderful place to live. Um, you know, I've talked to a lot of investors recently who are asking about whether Berlin is a good place to go. Uh, investors and sort of LP level people. Um, and there is often this kind of like, what's the scene in Berlin question? To me, the, the advantage of Berlin is that people want to live there. That's the first thing. Like, it's just a cool place. It's cool if you're, if you're young and sort of alternative or, you know, you're interested in uh, even the more kind of conservative, old-school European values. You get kind of everything in Berlin.
6:33 Speaker 02 So when my wife and I first heard about the opportunity for Wunderlist. It was it was first Berlin that made me even open the email at the time because the subject said CTO Berlin and we just love Berlin. It really stands out among the European cities as a wonderful place to be. So with that in mind, it has been very easy for us at Wunderlist, for example, to attract international talent from almost all over the world and and certainly even the West Coast of the United States because it's a nice destination for people and a place where you can have a good lifestyle.
7:11 Harry Stebbings? And talking of Wunderlist standing out there to you in that email, in 2013, to-do list apps were really rather common, you know, as they are now. So what do you think made Wunderlist the all-star to-do list, you know, the app of the year it was? What made it so special?
7:29 Speaker 02 Simplicity primarily. Our our chief design officer, Benedict Lennert, he he always says that the advantages we had and have are technology, design, and simplicity. And and the design of it, it's it's absolutely beautiful. That's the thing that kind of first catches your eye. And and by that I mean visual design. But taking it another step further, what we have done is removed everything we could. And there's probably still more that we can remove. It's almost like this meditative mental exercise of looking at something that already seems like it is at its essence and figuring out what else you
8:08 Speaker 02 can take out. We we actually wrote a post that summarizes a career full of observations that I've had and that Benedict has had about business software. And it's called Why Business Software is Broken. And it's all about the the historical war between customers and suppliers of enterprise business software, where it's like this this self-defeating fight for features and complexity. It's all driven on fear. And it's driven on, you know, fear-based negotiation tactics. So I've been on the purchasing end of this at big companies in
8:49 Speaker 02 the past. And the way it sort of plays out is you're trying to negotiate a license for some business software, and you ask for everything you might ever possibly want, every ridiculous bit of complexity you can think of. And ultimately, if the the vendor can't say yes to everything, you can use that as a way to significantly drive down the price when you're comparing vendors. So vendors end up saying yes, which means the software that they create gets worse and worse and more complex over time. And it ultimately makes the experience for the customer way worse as well.
9:23 Harry Stebbings? So do you think there's more room to go in terms of improving the consumerization of enterprise software?
9:29 Speaker 02 Oh, I mean, we're heading in the right direction, but definitely. And and the reason I say definitely is that. Uh, you know, Wunderlist is is a to do list application. Although I like to say technically it is a multi master, cross platform, mobile friendly distributed database system, but that's only because I'm a nerd.
9:49 Harry Stebbings? Cocktail party friend.
9:51 Speaker 02 Well, it is at the cocktail parties I go to.
9:56 Speaker 02 Wunderlist is one example, but. You know, enterprises run on a whole lot more than than to do lists and and a whole lot more than even just the productivity applications that we think about day to day. There are so many enterprise specific ones, domain specific ones. And I think even the consumer first approach.
10:18 Speaker 02 Is burdened by a an industry wide legacy of. This this thing that I was describing before, which is. Not really understanding, like we're all kind of sitting inside this this vacuum of how enterprise and business software has worked in the past. And even those of us who want to break through it, we it's hard for us to see. So with Wunderlist, for example, you know. We the the team before I joined had created something called WonderKit. And the DNA of the company was very much exactly what I'm talking about, this this simple consumer first approach. But WonderKit was their experience of going in with that mindset immediately.
11:00 Speaker 02 And completely losing their way. They they made something incredibly too complicated and they replicated the mistakes of the past and and they ultimately realized their mistakes, killed the product and went back to the basics of Wunderlist and realized the vision of Wunderkit by building on simple building blocks of Wunderlist instead of trying to create this complicated beast. And I would say that a lot of the companies that are that are trying to create simple, elegant, human-friendly software, they will they will have bad habits that they've learned that are hard to even recognize. And that's why I said earlier, it's kind of like a meditative, introspective process to even figure out what the essence of software is. And that's something
11:44 Speaker 02 that the team before I ever joined Wunderlist was really great at, and I think why we were App of the Year and and won so many other awards and and ultimately were acquired by Microsoft.
11:55 Harry Stebbings? And are there any features then that that you would like to add but still think would be in keeping with the minimalist aesthetics of the product?
12:02 Speaker 02 No, no, I I don't want to add any features. And that's not to say we won't, but personally, I would like to never add another feature to this piece of software. I think it's done. And I say that it's sort of a lie because I think the the product, the client of Wunderlist, is done and it's up to us to guard simplicity. And that's the promise we made, actually, in that post I was talking about why business software is broken, is that we would we would be the guardians of the simplicity of the product. That said, Wunderlist can and should be the thing that connects all of the other things in your your world that you need to get done.
12:42 Speaker 02 So, you know, there are all these different implicit and explicit inputs and outputs of the tasks you need to do in your daily life. For example, email is a big one. Calendar invitations are a big one. Trips coming up, conversations that you have via messaging applications, whatever they happen to be. Wunderlist can and should become the blue, the glue that recognizes those things, or at least allows you to explicitly input them in a seamless way. And helps you make sure that you don't forget them and you're doing things in the right order that you're able to prioritize. And then integrates with external services that could then help you accomplish them.
13:23 Harry Stebbings? And what are the most requested features by users have you had in in the past?
13:30 Speaker 02 Ah, in the past, um.
13:36 Speaker 02 The the biggest one that we held off on for an incredibly long amount of time was folders. So, you know, for those who haven't used Wunderlist, it is.
13:47 Speaker 02 A list of lists of things that you need to do and inside the lists are tasks and inside the tasks you have comments, files. Subtasks, et cetera. And for a long time, people had been requesting the ability to create folders and put lists in folders. So essentially just creating one more layer of hierarchy.
14:06 Speaker 02 And we held off for. A crazy amount of time really on doing that, even though many of us on the teams sort of knew we wanted it. It it was a an internal battle to hold off on doing that as long as we could. And that is sort of the way we we approach feature requests, even when they're coming from ourselves. Because we realized that we we were able to manage our work and lives with Wunderlist without the folders. And so we started to look for ways of working that emerged that would satisfy the needs of folders without introducing a new feature. Ultimately, we decided that folders really were an essential part of the experience for power users.
14:49 Speaker 02 And we added added it later this year, but I think it had been on the request list since the initial launch like four and a half years ago.
14:56 Harry Stebbings? And talking of kind of user experience there, both with Living Social and with Wunderlist, you created a product with really incredible habit-forming abilities with users. How did you go about creating this product and when when you were was user retention key to the building of it?
15:14 Speaker 02 Sure, well, I I think in in both scenarios.
15:20 Speaker 02 The products were inherently habit forming. You know, with Living Social, of course, you're receiving a daily email and that's what you're signing up for, at least back then, when I was working on it. And so therefore it will create a habit as long as you continue to receive and look at the emails. With Wunderlist, the whole point is to drive your habits. So we kind of start off with an unfair advantage there in terms of habit formation. But I would say in both scenarios, the teams, the product designers and technology teams at Living Social and on Wunderlist were radically driven to to simple solutions and to avoiding complexity at all cost.
16:05 Speaker 02 And that's the core of how you can make something habit forming. You know, if you if you have a product that is complicated to work with and not a joy to work with, then it's going to be harder to get yourself into a habit of using it, even if you want to use it. So we have that as a foundation for habit formation. On top of that, of course, it is all about creating
16:29 Speaker 02 an experience that is, as I said, a joy to work with, but also doesn't get in your way. And that's where we get into really looking at funnel metrics and and removing barriers to usage in in a more engineering style approach. So with with Wunderlist, we literally never paid for advertisement. We never really poured gas on the top of the funnel because we were so obsessively focused with the next steps, with not losing people when they started using the product, with understanding what it was that that
17:07 Speaker 02 kept people in, that got people excited about the product, that that confused and frustrated them. And so it has, for us, it's all always been about engagement and monthly and daily active usage.
17:23 Harry Stebbings? And how did you measure that engagement? Did you do in terms of like when you had new updates or potentially new designs or features? Did you test in mass market testing or did you do very targeted niche testing within maybe the Wunderlist team?
17:39 Speaker 02 We experimented with a lot of different things. Sometimes it would just be like, we really believe in this feature. We're just going to launch it and we're going to to compare and contrast the the effects of the feature after we launch. We we are very fast when it comes to product development. So even in a scenario like that, it's easy for us to to make changes, tweak and and relaunch something if it doesn't work as expected. But we also built our own feature testing system, our own analytics frameworks. And we have recently made quite an investment of of time and energy into user testing of features,
18:21 Speaker 02 sometimes even before we develop them, so that we can get features into the hands of real people who aren't inside our heads and and see what makes sense to them. And that's been kind of a huge revelation, coming from a the engineering inspired, very data oriented approach to a broader, more human approach of just literally sitting with people and seeing what they do with the product.
18:47 Harry Stebbings? And we have to touch on now the the acquisition. A huge congratulations to you for that. And we've actually got a question from Carolina Brochado, a friend of ours who was on the show from Atomico with Mattias. And Carolina wanted to know, what is it like moving from a small man startup to a giant corporation like Microsoft? I mean, how's the company and your role changed since the acquisition?
19:12 Speaker 02 I think so. The way the question is is phrased is interesting because the question says like Microsoft. And I think the it would be really hard to generally answer this question. Because I can imagine it would be very different depending on where we went. For us, at this point in time. Joining Microsoft has been just like joining a larger version of ourselves to some extent. So in fact, when we when we first met the team at Microsoft, we were amazed and surprised at how well our visions overlapped and aligned.
19:50 Speaker 02 And so you probably won't even believe when I say it, but joining Microsoft has really just meant that we have more resources. We have more more people to talk to and learn from, more colleagues, I guess. But otherwise, it's very much like like it was before, only kind of amplified.
20:10 Harry Stebbings? And you've managed to retain your kind of startup culture within the Microsoft ecosystem.
20:16 Speaker 02 Yes, yeah, really, nothing has changed. We're we're operating in Berlin. We're a solid team, making decisions the same way we did before.
20:25 Speaker 02 Like I said, we, you know, we have freedom to to to do things exactly as we did in the past, but we have more help when we need it.
20:34 Harry Stebbings? And what advice then would you give to founding teams and startup employees contemplating selling their business to much larger companies? Worked for you, but what advice would you give to someone who potentially may not work for with maybe not the right acquirer?
20:50 Speaker 02 Uh, yeah, it's hard to say, you know, uh, when it it's kind of like these people who have success in one business. So they write a business book that's prescriptive about how to be successful in business.
21:02 Harry Stebbings? Most business books ever written, yeah.
21:04 Speaker 02 Yeah, in fact, I wrote a book like that about how to be successful in one's career. And I I fully understand that a lot of it was luck and a lot of it was stuff that only I would do.
21:14 Harry Stebbings? And the links for chance book can be found in the show notes, not to worry, stampede.
21:19 Speaker 02 Oh, thank you.
21:22 Speaker 02 So I guess.
21:25 Speaker 02 I can say that what we did was we evaluated whether there would be a fit in the same way that you would evaluate an employer when you're being interviewed and essentially interviewing them for a job. At least that's the way I looked at it, and I think the rest of our management team did. We thought, is this someone that I really want to work with for a long time? Do they understand what I'm trying to do? And when I say I, I mean the company at this point. Do they understand what I'm trying to do? Do our goals align?
22:01 Speaker 02 And will I be able to work in a way that that makes me and my team comfortable? And for us, the answer to that just consistently was a yes. And so we went ahead with the deal, and it has so far worked out very well and proven to live up to our expectations.
22:20 Harry Stebbings? And if it's okay with you, we're going to dive now into a quickfire round.
22:25 Speaker 02 I'm not very quick, but we can try.
22:28 Harry Stebbings? So your favorite book and why?
22:32 Speaker 02 Maybe it's not my favorite, but one I always reference is The E-Myth Revisited by Gerber. And the reason is, and just be warned, it is really hard to read if you don't like the style. It's a conversational style. E stands for entrepreneurial. It's about why small businesses fail. And the why of it is that he lays out a strategy in a way of basically a systems thinking approach to business that you could apply from any scale to your own personal career up through running a large company.
23:05 Harry Stebbings? And then career highlights, what would it be?
23:08 Speaker 02 Career highlight, working at Microsoft, obviously, on Wanderlust. Before that, though.
23:14 Harry Stebbings? Well done, ticking the box there.
23:16 Speaker 02 But before that, very honestly, when I was at GE, I had the opportunity to start a development center in Bangalore, which was the most educational experience of my career and my life. And if anyone has a chance to put themselves in a culturally uncomfortable situation like that, I would highly recommend it.
23:37 Harry Stebbings? When I say successful founder, who's the first person that comes to mind?
23:43 Speaker 02 Steve Jobs, but only because I'm brainwashed.
23:47 Harry Stebbings? Your favourite newsletter or blog?
23:50 Speaker 02 Um, I don't read them anymore, so I don't have one.
23:53 Harry Stebbings? Okay, uh, and then your entry into angel investing with Side Stage, is there more to come? Or is it a one-off fall in love with the product?
24:01 Speaker 02 There is more to come, yeah, uh, and I'm, I'm quietly doing some things now that I'll get a little louder about later this year.
24:09 Harry Stebbings? And then finally, the next five years for you and for Wunderlist.
24:14 Speaker 02 Uh, so for me and Wunderlist, it is integrate deeply into, to Microsoft, be the layer that connects things in terms of tasks, things you need to get done, and continue to both learn from one of the largest, most important technology organisations ever, but also spread the Wunderlist culture and way throughout the company.
24:37 Harry Stebbings? Well Chad, it's been an absolute pleasure having you on the 20 Minute VC. Thank you so much for joining us today.
24:43 Speaker 02 Thank you.
24:43 Harry Stebbings? An amazing story from the legend that is Chad Fowler, and a huge hand to Chad for giving up his time to be on the show today. And don't forget your chance to win the signed copy of Venture Deals by Brad Feld. All you have to do is click the link in the description of this show or on the website at www dot the twenty minute vc dot com and like our Facebook page. And if you want to be prioritised, click the click to tweet link in the show notes of our previous episode with Kamal, and your chances will be significantly increased and you'll be placed on a prioritised list. Before we leave you today though, we live in a world of secrets, but secrets can be incredibly important for startups to protect themselves. So ensure that you have trade secret rights in place, allowing you the right
25:28 Harry Stebbings? to take action against anyone who breaches an agreement or confidential relationship, or even who steals or uses other improper means to obtain secret information. To get this vital layer of protection, give my buddy Chris at Vidal Law a call on three one two eight nine five four nine nine three, or visit their site at www dot vidal law dot com. Thank you so much as always for your continued support, and we would love to hear what you thought of today's show. And you can let us know by emailing me harry at the twenty minute vc dot com, all in letters. And we look so forward to seeing you in the next episode.
Previous 20 VC 077: Part 2: Kamal Ravikant: The Future Of Venture Capital Next 20 VC 078: BETAWORKS WEEK: Matt Hartman, Director of Seed Investments @ Betaworks Page updated October 26, 2026 · transcript and summary are machine-generated
