Lessons from a Multi-Multibillion-Dollar Business Founder, Kevin Ryan

A few weeks ago, I had the opportunity to join a fireside chat (hosted by the Yale Entrepreneurial Society) with Kevin Ryan, who is an investor and one of the biggest early-day internet entrepreneurs.

The Startup Mastermind 🧠 (Source)

He is best known for founding several businesses like Mongo DB, Gilt Groupe, Zola, Nomad Health, and Business Insider. Most recently, as the founder of AlleyCorp, Ryan continues to found and fund new companies every year.

1.Take risks

From 1996 to 2005, Kevin was helping to grow DoubleClick, one of the earliest known application service providers. At that time, NYC wasn’t home to the tech hub or startup ecosystem that it has today.

Yet, Ryan helped grow the ad serving company from 20 to employees, expanding the business into 25 countries — all before breaking even.

But it wasn’t magic. Kevin merely demonstrated the value of thoughtful/careful risk-taking.

The way to know?

The questions he suggests you ask yourself are:

  • Do I have enough signs?
  • What’s the downside if I don’t take the risk?

2. At its core, a successful startup should do two things

  • Solve a problem
  • Do it better than everyone else

Who needs business class!

3. Trust yourself


When you’re running a business as CEO, you’re receiving input from a range of different stakeholders. But at the end of the day, decision-making comes down to you.

And that’s why you have to have the “good ego” to use your own instincts and trust that most of your decisions will end up well. If not, reverse them and move on.

As Kevin put it:

Think of yourself as a professional baseball player. You know you’re going to strikeout 2/3 of the time, and you may still lead the league at hitting. So you cannot be afraid to step up there and make the calls. Even if they’re not all great, you have to assume that you’re making enough good ones.

4. When choosing a job, the pay isn’t the only important thing

One of the worst questions you could ask a young person is “what do you want to be when you’re older?” — and it’s fair. Choosing what you want to do for the rest of your life can be a daunting task.

But when asked about choosing “correctly”, Kevin responded by saying that it’s not only the pay you need to look out for when job-seeking.

In fact, it’s much bigger than that. You don’t need to think about the job you’re pursuing, but the you plan on entering.

When it comes to DoubleClick, one major factor in its success is the fact that internet-based services were still on the low, and they were among the first “pioneers” in that space.

In that same way, Kevin put it like this:

5. When starting a business in an unfamiliar space, naivete can be a strength

But not always.

Some of the most successful startups were founded by people with no industry expertise, like Travis Kalanick with Uber or Brian Chesky with Airbnb. However, that being said, these startups operate in the

When looking to enter an industry that you have no experience in, be cautious that this start-it-from-the-bottom-now-we-here principle does not apply in the same way to technical spaces.

Naivete be your superpower, but you still need to go deep in your research and understand the customer.

Those were my biggest takeaways from the talk, but before I end it off, here are some additional notes 📝 :

  • Choose your board members wisely. Look past their
  • If you’re unsure when to raise more value, think about the theoretical impacts and weigh your options accordingly
  • Even when things are rough, you should believe in what you’re doing. If you don’t, leave!
  • Maintaining relationships with people you meet can get you a long way

  • A good team — communication especially is key
  • A good idea — show case studies of customer satisfaction when possible and prove that there is demand for your idea
  • A good market — is your market size predicted to grow?

And that’s about it! Thanks so much for reading and I hope you gained a thing or two from me, or rather, Kevin Ryan. If you’re new here, hi! My name is Aneka and I’m an aspiring innovator and entrepreneur myself. To learn more about me, feel free to visit my portfolio or subscribe to my newsletter!

(Also, if you have an extra minute — let’s connect on LinkedIn!)

Interested in innovation and always ready to learn more!