6 May 2022

Link to podcast: https://www.thetwentyminutevc.com/podcast/ian-siegel/

Link to transcript: https://docs.google.com/document/d/12EvpDwLXvjyI1AyoXie1q7ij1ktu3c3h

(20VC doesn’t release transcripts; so I got this done via Fiverr; you are welcome!)

Sajith: I found Ian’s thoughts on the power of storytelling, when to stop looking at data, why he tries to stay silent as far as possible, what kind of candidates he tries to hire, extremely illuminating. It is a masterclass in how to run a company, especially from the perspective of a growth founder.

All words below are Ian’s.


Storytelling is crucial to entrepreneurship.

I feel like the discipline of storytelling is something that is actually crucial to being successful as an entrepreneur and also being successful as a leader and also being successful as a peer. It is something that I have tried to actually invest a lot of time in with the employees at ZipRecruiter. So I make everybody tell the story of the work that they are doing in a way that a layperson could understand. If you cannot explain it to me that simple, then you yourself do not understand what it is that you are doing. I truly think writing is an underserved practice in all forms when it comes to entrepreneurship.

A lot of it is about finding empathic points of entry for your audience. In particular, when you are describing say product features. A lot of people will describe the product's feature and I would say no, no, no, do not do that give me a user story. Tell me what the experience is for a user, and then insert the product feature to show how it made their life better and made the experience easier. Whatever it was that aspect of storytelling, where you tell it from the point of view of how to impact the audience or how to impact the user is one of the great gifts that I feel that we give to the people who work at ZipRecruiter because they go on and then they deploy that technique and I have heard it over and over again that everywhere they go, people are like "amazed by the decks they write and the way they talk about their work" and I am like, "I know, I know, you were drinking champagne here. You didn't even know it."

Data-driven cultures are great for optimizing but not for innovating.

…when we built the company, we bootstrapped for the first four and a half years, and we got the company in the north of 50 million in Revenue, with millions of free cash flow before we ever took any outside funding. And the way we did, we were incredibly disciplined operators and we created a culture of disciplined operation where like I said, "you can make any argument you want as long as you support it with data." That was the culture we created.

People became meticulous about capturing data and talking with data and making logical arguments with data and it was awesome and it still is awesome. And now we are like, we do hire hundreds of millions and in next couple years, we will be in the billions probably and so it looks very exciting from a revenue perspective. But what is the dark downside of being in this highly analytical data-driven culture? It is very easy to use data to optimize an existing product. It is very difficult to use data to innovate and build a new product.

And so, the trap you fall into is before you do anything, you always want to prove with data that you are doing the right thing and it was so interesting because when we went to tackle the job seeker side of our marketplace, which was the second product we built, the teams were doing scads of research, spending millions of dollars just trying to figure out what the right thing to do was.

Actually, it is so rare, as a CEO I think we could talk about this if you want to, but I always say like "my job is to do as little as possible to create accountability and autonomy. I want to make less than 10 decisions here." But one of the times, I threw my CEO card on the table and fully stepped in is when we were working on the job seeker product and I said, "everybody stop. We're doing this the wrong way. Here's how I want you to build a job seeker product. Here's the only metric I care about. What is the product you yourself would want to use? What is the product that you would recommend to a friend or family member if they were looking for work? and tell them with confidence that they should use this. That's the product I want you to build. That's it. Go with your gut, build that, have the courage and the vulnerability to put that version 1 out there, and then we will start optimizing, just start with like a thesis around, like, what would be different from the way the market works today that would make you want to use a product. Make some bold claim and then make it true." We had a lot of data-driven decision-making and then we got somewhat stifled by it when we got to the innovation phase, but fortunately, we are now powering through that.