Oct 9, 2015 · 26m · 20vc
FF 016: Chad Fowler, CTO @ Wunderlist, App Of The Year 2013
0:00 / 0:00
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The 20 Minute VC, host Harry Stebbings interviews Chad Fowler, CTO of Wunderkinder, about his career transition from music to software leadership, the design principles behind Wunderlist's success, and lessons learned from the company's acquisition by Microsoft.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 25.2% of the talking time here. How this is scored →
Harry as informed peer 2.1 Guest teaching 3.6 Guest disagreement 2.0 Harry pushing back 0.4
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 12:03 Firm refusal of new product features
Chad directly shuts down Harry's prompt regarding feature additions with 'No, no, I don't want to add any features,' firmly rejecting the premise that a successful product must continually add features.
Hardest push from Harry ▶ 20:10 Pressing on startup culture retentionHarry follows up on Chad's glowing account of joining Microsoft by specifically challenging whether Wunderlist actually managed to preserve its authentic startup culture inside a giant corporation.
Biggest teaching moment ▶ 8:00 Exposing the dynamics of enterprise software bloatChad gives a detailed breakdown of B2B procurement dynamics, teaching Harry how enterprise buyers demand excessive features as pricing leverage, which ultimately ruins software user experience.
Harry holds his own ▶ 9:23 Framing enterprise software consumerization trendHarry displays sharp domain knowledge by introducing the consumerization of enterprise software trend and skillfully matching Chad's technical jargon with playful banter.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Book Giveaway Contest and Vidal Law Sponsorship | 1 | 1 | 0 | 0 | The segment begins with host housekeeping, book contest promotions, and sponsor readings before introducing Chad Fowler. Chad gives a polite, narrative overview of his transition from music to software engineering without friction or debate. | |
| Evaluating Berlin and Europe as Global Tech Hubs | 2 | 4 | 4 | 1 | Chad mildly pushes back on Harry's premise about Europe having a competitive advantage over the US, claiming location matters less now. He then educates Harry on the specific affordability and lifestyle appeal of Berlin rather than broader European tech advantages. | |
| The Power of Simplicity in Wunderlist's Product Design | 2 | 5 | 1 | 0 | Harry asks what made Wunderlist stand out in a crowded 2013 market. Chad delivers an insightful explanation of feature removal and details how fear-based enterprise software procurement creates bloated products. | |
| Enterprise Consumerization and Lessons from Wunderkit | 3 | 4 | 1 | 0 | Harry demonstrates good understanding of industry trends by asking about the consumerization of enterprise software and engaging in light technical banter. Chad candidly shares the lesson of Wunderkit's failure and why companies struggle to overcome complex software legacy habits. | |
| Protecting Minimalist Aesthetics and Future Integrations | 2 | 5 | 5 | 1 | Chad forcefully shuts down Harry's question about desired new features by flatly stating he wants to add zero features to protect simplicity. He goes on to educate on how Wunderlist resisted user pressure for 4.5 years before introducing folders. | |
| Designing Habit-Forming Products and Retention Strategies | 2 | 3 | 1 | 0 | Harry asks a structured question regarding product habit formation and user retention. Chad explains how product simplicity and obsessive focus on conversion funnels allowed Wunderlist to grow without paid marketing. | |
| Engagement Measurement and Human-Centered User Testing | 3 | 3 | 1 | 1 | Harry asks about user testing methods and relays a listener question about the Microsoft acquisition. Harry gently presses Chad on whether Wunderlist truly managed to retain its startup culture inside a major corporate environment. | |
| Strategic Advice for Founders Evaluating Acquisition Offers | 2 | 4 | 3 | 0 | When asked for advice for founders contemplating M&A, Chad dismisses prescriptive business books and acknowledges the role of luck. The segment concludes with a rapid-fire Q&A round conducted in good spirit. |
Statements from this episode (12)
Berlin is significantly cheaper to operate in than comparable US cities
“And compared to most of 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. That's not a Europe wide advantage, but that is something very special about B…”
Wunderlist easily recruited US West Coast talent to Berlin
“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 certainly even the west coast of the United States, because it's a nice destination for people and a place where …”
Enterprise software bloat is driven by buyers negotiating on missing features
“And it's all about the historical war between customers and suppliers of enterprise business software, where it's like 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. …”
Wunderkinder killed Wunderkit due to excessive complexity before refocusing on Wunderlist
“With Wunderlist, for example, you know, we, the team before I joined had created something called Wunderkit, and the DNA of the company was very much exactly what I'm talking about, this simple consumer-first approach, but Wunderkit was their experience of Goi…”
Wunderlist CTO Chad Fowler wants to never add another feature
“No, no, 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.”
Wunderlist delayed adding folders for four and a half years
“Ultimately, we decided that folders really were an essential part of the experience for power users. 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.”
Avoiding complexity is the key to building habit-forming products
“And that's the core of how you can make something habit forming. You know, 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.”
Wunderlist never paid for advertising to acquire users
“So with Wunderlist, we literally never paid for advertisement.”
Human user testing yields greater insights than purely data-driven metrics
“We have recently made quite an investment of time and energy into user testing of features 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 see what makes sense to them. And that's …”
Wunderlist maintained complete operational autonomy in Berlin after Microsoft acquisition
“Really nothing has changed. We're operating in Berlin. We're a solid team making decisions the same way we did before. Like I said, we, you know, we have freedom to do things exactly as we did in the past, but we have more help when we need it.”
Founders should evaluate potential acquirers like interviewing a prospective employer
“I guess 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 …”
Wunderlist will become Microsoft's core task layer and spread its startup culture
“Ah, 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 organizations ever, but als…”