Wed · Apr 27

Doing the Hardest Thing First

In this episode of Startup School Radio, host and Y Combinator partner Kat Manalac first sat down with Roger Dickey, who is currently the CEO and co-founder of Gigster.

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Gigster launched out of Y Combinator's Summer 2015 class with a platform that connects companies that need development work done to top engineering teams. In the second half of the episode, Roger was joined by his Gigster co-founder and CTO Debo Olaosebikan.

One particularly interesting aspect of the interview was hearing Roger talk about what he learned from his earlier experiences building startups and products while in engineering school, and seeing different levels of failure and success through his career:

Kat Manalac : Did you learn anything specific from that first failure that you took with you later on, and even now to Gigster?

Roger Dickey : I would say one of the big things is not to put the cart before the horse, so to speak. You need to make a list of the hardest things you have to do for your company to succeed, and really honestly go down that list in order of hardest to easiest. So for most businesses, the hardest thing you have to do is prove that you've built something that people want. It's not print [company] t-shirts, it's not change your LinkedIn, it's not go around to conferences telling everybody that you're the CEO of a startup of a one-person company.

It's really just going and talking to customers. When you've never done that before, it's hard to get in front of people, impose on them for their time and say, "Kat, I have this idea for this tutoring app. Would you use it?" It's an awkward thing to do, especially for engineers. Especially for engineering founders, it's hard to go up to somebody and say, "Would you use this product that I built?" So that was actually the hardest thing and we didn't do that first. We really should have.

Kat Manalac : Right. I feel like that's a good lesson and focus in what you really should be doing, which is mostly coding and talking to users.

Roger Dickey : Yup.

Kat Manalac : I see a lot of people spending days or weeks or months on logo design and trying to figure out what URL and at a certain point it's just like, "You just got to build something."

Roger Dickey : Yeah, and I would say it's not even coding. Because coding is the easy thing if you're an engineer. Engineers love to sit there and write code. I've had companies I've worked on before where I've spent three months coding something. Then I start sharing it with people, and nobody actually wants it. I think, particularly if you're an engineering founder, you have to resist the urge to sit there and write a ton of code before you've talked to customers.

Kat Manalac : It's sort of uncomfortable, that process of sharing what you've built until perhaps it's at a certain point. So how long do you now wait to show people anything?

Roger Dickey : I don't build anything until I talk to customers. I've had a few things I've started where I've gone through a pretty lengthy ideation process, and we actually did that recently for Gigster. We tried a lot of different ideas first. We started off with a two-week build if we wanted to kind of prototype something. The first week would be just Facebook messaging 50 people, LinkedIn messaging 50 people, grabbing coffee with 5 or 10 people that we trusted who are in that space, saying, "Hey, is this something you'd use? How would you want this to look?" Then the last week would be coding it. And then we'd ship it on Product Hunt or Hacker News. I think two weeks is the maximum amount of time you want to spend before getting something to market, even if it's just a WordPress landing page.

...You see a lot of people who have some fear, and I wouldn't call it dishonesty, but it's almost like people are like, "Oh, I'm doing this restaurant delivery startup, but I'm not sure if I'll be able to get restaurants on board because that's really hard." So they'll sort of subdue that and say, "I'm not going to do that. I'm just going to make a really beautiful iOS app for delivery." And they'll make this really beautiful app. And you're like, "Well, how many restaurants have you talked to?" And they say, "Oh, we talked to a couple."

They know, and you know, that the hardest part of building a restaurant delivery company is getting restaurants on board. But they didn't go and do that at first.

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