Whop's Jack Sharkey on Scaling a Rails Unicorn - Rails World 2025

Hey, I'm Andrew. We're here in Amsterdam at Rails World 2025, and I'm with Jack Sharkey, the CTO and co-founder of WAP. He had a talk yesterday about his journey as a startup founder on Rails. Hey Jack, how's it going?

Hey Andrew, it's great to be here. Thank you for having me.

Awesome. So something I was really interested in your talk yesterday, like any good founder, you have a history of ideas, a history of entrepreneurship, but you also have a history of different tech stacks, and it took you a while to get to Rails. And I think you said in your talk yesterday it changed your life. So I'm interested to hear more. How does Rails compare to the other tech stacks you worked on and What was different about Rails that helped you be successful?

Yeah. So I started programming when I was around 13. And I didn't get to Rails when I was— until I was like 20. So that's about 5, 7 years of not using Rails. And my experience beforehand was I came from a Node.js Express background. And I never actually used a relational database before, which is probably the biggest difference that actually came true to me. So some of the issues that I had in my other tech stacks were in Express, I could never actually easily stand up an app. I would have to parse JSON and do these random things just to get my parameters. And when I found Rails and I could just access params, it was life-changing. And then once I ended up using Postgres for the first time and putting ActiveRecord on, building features and building projects actually started to make sense. Because ActiveRecord allows you to model data in a way that is intuitive to your brain. And it's intuitive on how relationships work. So that was, I think, the 2 biggest things when I got to Rails. It's like, one, it's really easy to make API endpoints. And 2, the data modeling, which is really how projects and features are made, was just 10 times easier than I've seen before.

Awesome. So it sounds like you've gone through a lot of growing pains using Rails, and that now today WAP is in a stable place. So why don't you tell me a little bit about how the team is working today and what you're doing at WAP?

Yeah. So we've been in business for about 4 years, and the app has progressed a bit. But it started as Rails, and it's still Rails. We've had to swap out our data store, like, 3 or 4 times. We've moved infras twice and built countless features over and over again. But at this point, we're still using Rails. We're very happy with it. I'm happy to say that in the last 4 or 5 months, we've been very stable, and uptime is so important for us because people use our platform to make an income online. And if you go down, it means they can't make money, and that's their business, that's their livelihood. So it's so important to us. And where we are right now is our team's about 15 people engineering-wise, about 3 or 4 backend engineers, which is pretty remarkable because we stand up over— processed over $140 million last month just among 3 or 4 backend engineers.

Yeah.

Why that's valuable too is Our team is scrappy and they're— it's a flat org and everyone's a builder and responsible for their own aspects. Even me, I'm programming 70-80% of my time right now. So I think that's kind of the culture we want to build is we just get people in and they want to build and they want to contribute. And a lot of these people are entrepreneurs themselves and they want to help other people further our mission to make money online. So that's where we're at right now. And I can happily say that I can have this interview with you and have a 90% likelihood that we are not going down.

Well, don't jinx it. But that's awesome. So tell me, what's like in the future for Wapp coming up next year?

Yeah, so like I said, our mission is to make people money online, and we want to continue to evolve and allow people to launch any kind of business model on the internet. We see the future of kind of the 9-to-5 on the way out and the entrepreneur life coming back up. Everyone has passions and ideas, and with the internet getting more prevalent and many more people turning to that to earn income, we want to have Wapp be that centerpiece. The biggest, I would say the biggest ethos around that that we're making a bet on is our developer app store. Our developer app store allows developers to create apps on top of WAP that creators can then either install as like a B2B thing, such as make an app to reduce their churn or help them find new customers, or what we call a B2B2C app, whereas you create an app that creators can then sell to their customers. For example, let's say you are in the sports betting niche and you want to make an app that allows creators to connect their FanDuel accounts so they can show verified legitimate bets that they took. So it's basically boost trust for all the end consumers. You can do that. So right now, WAP is really taking a bet on this App Store. We're basically calling all app developers, everyone out there that wants to come on and really help make money on— they can make money online too and really build on top of this platform. And we believe it's kind of the future of entrepreneurship.

Awesome. So cool. Okay, last question. So You were talking about how you want more startup founders to be using Rails and how it's such a great choice for startups, and I agree. Can you give your pitch to startup founders on why they should choose Rails?

Yeah, so, we've been around for 4 years, and we've been able to develop, I can say confidently, faster than almost any of our competitors. And sure, our team is scrappy and we've worked long hours, but that is the one constant that's been through that has been Rails. Rails has allowed us to iterate faster than I've ever iterated before in my life, and I've seen other people able to iterate. And I believe iteration is the key to a successful business. You have no idea what you really want to build. You just have to listen to your customers and keep going, keep going, keep going. And when I found Rails, I was so resentful. I was like, there's no way we're using it. It's old. No one uses it. We have to use the modern tech stacks. And I got convinced to use Rails, and it was one of the best decisions I've ever made because I've never had joy and productivity and fun building like I have with Rails. So I find it, it's sad that most startup founders aren't choosing Rails, and I don't blame them. I think that we can do a better job of marketing Rails and showing the power of it. But once you do come across it, you will realize it is the superpower you need to actually scale your startup and scale your business, and that's what we found so far.

Awesome. Okay, Jack, thank you so much. For those of you at home, Jack's talk will be online in 24 hours, so please check it out to learn more. Thanks.

Thank you, Andrew.