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. 👇
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.
For QSHOP, I led the design, and I hired three engineers to build the product with me. We all worked together in a sketchy office connected to an abandoned warehouse. We had stand-up meetings every day. Lots and lots of whiteboard time, drawing user interface ideas and architecture/data flow ideas.
That was a while back, but I believe the languages we used to build it were Java (server) and JavaScript (client).
At BVS, we have five companies under development. The tech stacks vary a bit from product to product, but generally, we use:
Backend: Python, Go, Django, FastAPI
Web: React, Next.js, Vue.js
Mobile: Swift, Java, React Native
Infrastructure / DevOps: AWS, Docker, Github Actions
Data / Analytics: PostegreSQL, Segment, Amplitude
AI dev tools: Cursor, Claude 3.5 Sonnet, Mem0, Replicate
AI research / brainstorming tools: Perplexity, Gpt 4.0 / GPT-o1, Claude, Grok
AI content tools: Dall-e, Midjourney, Ideogram, Runway ML, HeyGen, D-ID, Pika, ElevenLabs
At Kayak, it took us a good year+ before people really liked the product. The first version was terrible — we built the front-end in Macromedia Flash, which was a disaster. The first logo for Kayak was designed by me, and we actually won an "award" on some small UI blog for "worst logo on the web", haha.
But then we brought in Lincoln Jackson as head of design, and he designed gorgeous screens for us, using Photoshop! (We started in 2004.)
We made lots of mistakes at Kayak over the years.
We hosted our own servers, since this was well before cloud computing. At one point we had DC-powered servers, don't ask me where we got that idea, but the company went out of business and we then quickly re-architected for Dell Linux servers.
We also built half our dev team in Bangalore. The idea was not so much saving money, but instead, having one team focused only on travel integrations (Bangalore) and the other team focused on user interface (Boston). But it turned out that the MD we hired in Bangalore was not great at hiring top-notch engineers, so we had to shut that office down.
That's not to say that offshore development is a bad idea — since then, I have found a remote dev team at Arbisoft in Pakistan, and they have been tremendous at working with my US-based teams.
The best way to attract users is to have your early users brag about you to their friends, showing their excitement that they (the early users) "discovered" you.
To this day, it delights me when someone points out, "I was a Kayak user before you guys became big!"
My mentor, Gail Goodman, told me, "You should measure the number of seconds it takes from when someone first sees your product to when they say 'wow'." You need to make this happen as quickly as possible. Certainly less than a minute, and ideally much less than a minute.
Across all my companies, our primary lever for revenue growth was user growth. Simple as that.
But we also found a way to increase revenue per user by adding ancillary products. For example, Kayak started as a flight search engine, but over time we added hotels, rental cars, cruises, vacations, etc.
What I've learned over my decades is that the #1 most important thing in any company — the difference between a $1M outcome and a $1B outcome — is how well you hire.
If you can truly hire an entire team of A+ people, you'll crush it.
Now, some people say hiring all A+ people is impossible, usually for two stated reasons:
That you need some B people to do the shit work
All the A+ people's egos would not all fit in the same room.
However, I strongly disagree with these two common criticisms. The absolute best A+ people will do whatever it takes to get a job done (often automating "shit work"), and I've found them to be people who really enjoy working with other smart people.
For more about hiring, see this hiring blog post I first wrote in 2002 but which still rings true for me today!
My strongest advice is to choose carefully who you spend time with. "You are the average of the five people you spend the most time with."
Seek friends and collaborators who are EXCEPTIONAL.
Spend lots of time with them, including long dinners where you all talk bullshit and brainstorming, as well as how to create new products and companies.
You should, of course, also listen to great podcasts, and read great books and blogs. Ask your most trusted friends for advice on what they are reading and listening to.
For the next ten years, I want to create 1-3 companies a year. Most of the new companies we create will be "AI-first" companies.
As examples, at BVS, we're building a "meeting intelligence company" that uses AI and human feedback to evaluate and improve business meetings. We're also now building a "therapy companion" AI that a therapist can program to help their patients in between human-to-human therapy sessions.
You can read my blog at paulenglish.com and you can read about my company at bvs.net.
Leave a Comment
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?
Guardian Info Consultant - Complete IT Solutions Provider
Hello Professionals 👋
I am representing Guardian Info Consultant, a leading IT solutions and cybersecurity firm.
🛡️ Our Core Services:
✅ Web & Android Application Development
✅ Digital Marketing & Branding
✅ Web Hosting & Cloud Solutions
✅ Network Security & Penetration Testing
✅ Cybersecurity Audits & Compliance
✅ Server Hardening & Maintenance
✅ IT Infrastructure Management
✅ 24/7 Server Monitoring & Support
✅ Full-stack IT & Cybersecurity Solutions for Enterprises
🎯 Whether you are a startup or an established enterprise, we help strengthen your digital infrastructure, secure your data, and ensure seamless operations.
👉 For any inquiries or collaboration:
📞 +91 8920693996
Let’s connect and explore how we can add value to your business. 🤝
#CyberSecurity #PenTest #ITSolutions #ServerHardening #WebDevelopment #AndroidDevelopment #DigitalMarketing #GuardianInfoConsultant
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? 🙏