How I Went From English Major to Serial Software CEO
I’m an accidental entrepreneur.
After studying English as an undergraduate, I used my skills in literary analysis to ... become the founding CEO of my first enterprise software company. Seven years later, we sold the company to EMC for $165 million.
I went from reading Hemingway and writing an epic fantasy novel to shipping a data de-duplicating file system.
Sound far fetched?
Most of my friends thought I would fail but wouldn’t tell me to my face. When I pitched my software idea to anyone that would listen, I could tell people were wondering: “Is this guy for real? Does he really think he can build a software company?”
There were plenty of times I wondered the same thing.
When I got started, I pitched to any investor I could find. I used my network to get audiences with “B tier” VCs in Southern California and Silicon Valley.
I was rejected by the first four VCs I pitched.
It was 2000. The dot com bubble was bursting around me. Everyone was getting out of tech. Instead of folding, I dug deeper. I pushed the VCs to tell me why they passed. And I learned.
What you don’t know … can make you smarter.
By the time I networked my way to pitches with five of the top ten VCs in Silicon Valley, I had finally learned enough. We received term sheets from three.
I took a big sigh of relief. We were on our way.
Coming Up with the Big Idea
I took a consulting gig one summer for a startup in California and … felt at home for the first time in my working life.
I was a fish in water. I had found my mission.
Software and technology is an incredible canvas for applied creativity. But instead of painting the world in colors or words, you paint it in binary—with 0s and 1s.
A few months after learning about the technology and startup world, I came up with the product idea for Avamar.
When I started Avamar, the enterprise tape backup industry was ripe for disruption. TiVo had launched and MP3 players abounded, taking VHS tapes and audio tapes and putting it all on disk.
I came up with the idea to use smart software to move enterprise backup data from tapes to disk—transferring product concepts from the consumer world to the enterprise IT world.
You might be thinking, how did an English major help invent a deeply technical data management product? I talked to the smartest engineers I could find. And I did a lot of Yahoo! searches.
It sounds ridiculous but it’s true.
It was a simple idea at its heart … except for the deduplicating hash-based file system we had to invent, which took four years to develop and harden.
Seven years later, we celebrated when we sold the company to EMC. A few quarters later, EMC’s CEO Joe Tucci told me Avamar was the second best performing investment he ever made (after VMware, of course).
In the years following the acquisition, EMC generated over $3B in sales from our product and transformed the data backup and recovery industry.
We sold it for millions. They made billions. Maybe I should have majored in math.
After getting shortchanged at Avamar, which I founded in Orange County, California, I decided to move up to Silicon Valley for my second software company, Delphix.
Strategically situated in the epicenter of technology, you have the privilege of buying $2M teardowns on busy streets and the opportunity to gaze wonderingly at roving herds of tech talent. Luckily, I had moved specifically to chase tech talent.
Delphix provides data 100x faster for developers to test their software than conventional means (requesting a refresh from DBAs and waiting for Godot).
Everything was easier the second time around. I discovered the problem and the opportunity for Delphix … because we created it with Avamar. Deduplicating backup solutions were built for storage efficiency—not for fast access and immediate use.
But Avamar customers wanted copies of data for everything—development, testing, training, analytics, and governance—and they wanted it all right now!
They kept asking if we could solve their data access problem. So I left EMC to solve it for them. I hired a strong development team in Silicon Valley, and we shipped product in a year.
Staples became our very first customer. In our first seven years, we sold $200 million in software and added 30% of the Fortune 100 as customers.
I’ve often been asked how I had the courage to take the risk, to walk the plank from english major to software CEO. For me, it all began with the moment of product invention, what I call the Lightning Leap.
When you have a moment of product clarity, when you can see how an innovative product can take control of what I call a Value Seam—a major opening in a market—everything changes.
Your life changes.
The product vision takes root in your soul. You can’t let it go. You can’t walk away from it. It demands attention. It demands action. And if it’s a great product idea, it can trigger an avalanche of success.
When you have clarity of product vision, there is no risk. Risk has an inverse relationship with vision—the clearer your vision, the less risk you’ll face.
Do you know how long it took Mark Zuckerberg to code up the first version of Facebook that went viral at Harvard?
In 2004, Zuckerberg explained his creation to the Harvard Crimson in a nonchalant manner: “I do stuff like this all the time. The Facebook literally took me a week to make.”
A week. For one coder. Alone.
That’s all it took for his site to go viral, for him to attract talented, experienced executives and investors such as Sean Parker and Peter Thiel, and for him to drop out from college to pursue his dream.
Did he have to walk a gangplank of risk? Absolutely not. The only risk was not getting started.
Over the last two decades, I’ve met with many founders of companies that have reshaped the world with software, including Bill Gates, Reid Hoffman, Marc Benioff, Marc Andreessen, and more. I’ve asked many of them how they came up with their own initial product ideas.
Surprisingly, the answers are pretty mundane.
My conclusion: Anyone can come up with the idea for what I call an Appzilla—software that can consume $1 billion in revenue and disrupt an industry.
To see just how mundane the original ideas can be for today’s tech giants, let’s go back in time and look at how they got started:
The origins for the biggest and most powerful tech companies that rule the world today are often … underwhelming.
In college, I wrote a paper on Martin Luther, who changed the world by defiantly posting his famous Ninety-Five Theses on the door of the Wittenberg Castle church.
In 1517, Luther challenged the central religious authority of the Catholic Church, arguing that humans could reach salvation directly through their own faith, instead of paying indulgences to priests and the pope.
Luther shattered a spiritual glass ceiling and changed the course of history by sparking the Protestant Reformation, which led to a radical group of Protestant pilgrims settling in America … and the eventual rise of Silicon Valley.
There are no barriers to innovation today. No technology priests or popes to worship — only the illusory conditioning that limits our minds and actions. I call it the Innovation Glass Ceiling.
Great innovators gather the cloth of today’s technologies until they pull forward a glimpse of the future. Once you see a vision of the future clearly, anyone has the power to shatter the Innovation Glass Ceiling.
Anyone can invent an Appzilla, even an English major.
What I love most about America is that even with no experience, if you have a great idea, you can get funded. I might have stumbled around at the start, but I persevered and ended up inventing multi-billion dollar software products.
You can, too. There’s never been a better or easier time to change the world.
About Me
I’ve spent two decades decoding innovation, collecting the hidden frameworks that drive many of the most successful entrepreneurs in technology today. I’ve personally implemented these frameworks, inventing software products at Delphix and Avamar that have driven more than $4 billion in sales. Disrupt or Die (available on Amazon) is my first book.
Parts of this article are excerpted from Disrupt or Die.
