Paul English on going from indie game designer to $2B exit with kayak.com
Paul English built kayak.com — maybe you've heard of it. That company alone sold for $2B, and he's had other exits to boot. Fair to say he's had the kind of success that most founders only dream of.
Now, he's building Boston Venture Studio.
Here's Paul on how he does it. 👇
Building household brands
I'm a software engineer and product designer by background. I'm best known as co-founder/CTO of Kayak.com, but I've had five other exits as well — in gaming, e-commerce, security, customer service, and podcasting.
My first business was a video game I developed as a teen. I ended up selling it for $25k. In many ways, this was a much more meaningful win than when I sold Kayak for $2B, because the game's success told me there was a future in software.
My first grown-up business was an e-commerce store creator called QSHOP, which I ended up selling to Intuit. I created that company during dot-com 1.0 as a response to Amazon's threat to small businesses. I wanted any small business to have beautiful, functional e-commerce storefronts.
I'm currently running Boston Venture Studio. We have eight products in that portfolio Deets, Lola, PartyClick, Supercal, SpamStrike, Xiangqi, Reki, Middle, and Funcontact. Three are paused, but five of them are still under development.
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This is super timely. I’m also building something in the compliance/legal tooling space — and it’s wild how confusing GDPR/CCPA requirements still are for small teams. Curious: how are you keeping up with changing regulations across regions? Manual research or legal API sources?
Btw what type of podcasts do you guys prefer?
It has been a long journey, but he finally made it. Needs the grit. I love the insights, and it is too rich content for a first-time founder like me.
This history is crazy
Love that your first $25k win meant more than the $2B one — that really says it all. Inspiring journey.
Inspiring story.
I feel this! I'm solo-building too and the mental rollercoaster is real. Keep going – you're not alone 💪
Very inspiring and motivating
I still use kayak to this day anytime I need to book flights. Love it.
What a name!))
Que trajetória incrível! Paul English é um exemplo inspirador de como perseverança, aprendizado contínuo e foco no time certo podem transformar ideias simples em grandes sucessos. Gostei muito da honestidade sobre os desafios iniciais do Kayak e a importância de ouvir o usuário para criar aquele efeito “wow”. Também concordo que contratar pessoas A+ faz toda a diferença — ter um time de alta performance é essencial para escalar de forma sustentável. Fiquei curioso para acompanhar os novos projetos “AI-first” do Boston Venture Studio, especialmente a ideia do “therapy companion”. Obrigado por compartilhar essa visão tão detalhada e prática!
By combining creativity and business strategy, Paul English transitioned from indie game designer to tech entrepreneur. As a result of his vision and innovation, he was able to acquire the company for $2B.
By combining creativity and business strategy, Paul English transitioned from indie game designer to tech entrepreneur. As a result of his vision and innovation, he was able to acquire the company for $2B.
hello all!
I like how you validated this before building. What’s been your biggest challenge so far?
yes are you are very right
Interesting journey!
How did you get your first users? I'm currently busy building a product that users love, but how do you get it under their attention?
To build a household brand, prioritize intuitive design and a product that users can’t stop talking about. Early wins, however modest, can be psychological rocket fuel.
Incredible journey Paul! From indie game design to $2B exit - that transformation energy is exactly what drives me.
I'm building AlbumForge (world's first solidarity software) and your story resonates deeply. As an adopted child from Vietnam who grew up with no photos, I understand how personal wounds can become entrepreneurial superpowers.
Like Kayak solved travel pain points, we're solving family memory loss - but with a twist. Every license sold automatically gives one free to a child in need. We're proving business can have a conscience.
Your persistence through setbacks inspires me. Currently coding after meditation each morning, turning my childhood absence into everyone's presence.
Question: Did your personal values influence Kayak's culture? How did you maintain authenticity while scaling to billions? 🙏
Building in public at albumforge.com - would love your thoughts on "tech with soul" approach!
RIGHT
Great insights from Paul. He was on the MFM podcast a while back too.
One part of this that I didn't get is the need to outline the tech stack for BVS companies. Is this mandated?
I don't think it matters what tools you use as long as the product is built/functional.
That was a good one!
no way
Very interesting one
Paul English's journey with Kayak is seriously inspiring — taking an idea and scaling it to a $2B exit is no small feat. It's the kind of story that keeps founders like me motivated as I work on building my own product, the HDO Box streaming app. Always learning from the best
My takeaway: minimize the time from user's first use to say WoW
An inspiring journey from gaming to a billion-dollar exit! What was the biggest mindset shift you had to make when moving from a creative field like game design to a data-driven business like Kayak?
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Wow, that's cool, an inspiring story for me because I really need it.
Well said. I believe this is the most important (and challenging) part of building a great product. If you can build something that "wows" users, it's more likely that they'll adopt the product and share it with others. This is great advice, thanks for sharing.
A very convenient website.
This was a great read, Paul. The reminder that “your users need to brag” really hit home — we’re seeing early signs of that with some of our AI experiments.
Also loved the idea of hiring A+ folks who enjoy working with other smart people. Resonates deeply.
Thanks for sharing such candid lessons — following your blog for more.
Incredible journey Paul! From game design to $2B exit - that's the kind of transformation that inspires me.
I'm building AlbumForge (photo software with soul) and your story resonates. As an adopted child from Vietnam, I understand how persistence through challenges shapes you.
Our approach is different - we give away 1 license for every 1 sold - but like Kayak, we're solving a real pain point (families losing 90% of their digital memories).
Question: How did you maintain your original vision while scaling? Did spiritual/personal values play a role in your business decisions? 🙏