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Serial Entrepreneur Building a Luxury Business: Trevor Traina, CEO of IfOnly (Part 1)

Trevor has built several businesses and is now working in a segment that he naturally aligns with—luxury experiences.

Sramana Mitra: Let’s start at the very beginning of your personal story. Where are you from? Where were you born and raised?

Trevor Traina: I was born and raised in San Francisco. On my father’s side, I’m a fourth-generation San Franciscan.

Sramana Mitra: Wow! That’s a rarity around here.

Trevor Traina: Yes it is. I was here through high school. Then, I went to Princeton for my undergraduate studies. Then I went immediately to Oxford to St. Catherine’s College where I got a graduate degree in Social Studies. Then I worked in New York for three years.
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Unicorn in The Making: Ross Mason, Founder of MuleSoft (Part 6)

Sramana Mitra: Do you have drivers that a lot of people need that you’re making significant business out of? Have you seen that?

Ross Mason: We certainly see clusters around certain SaaS applications. Obviously, Salesforce is leading the charge on enterprise. They really opened up that market. As such, we have a very strong relationship with Salesforce on many levels. We partner with them and they’ve also invested in us as a company. We work very closely with their field teams and even their product teams on helping drive more value to the product they’re bringing to the market by unlocking the data inside the organization.

To give you an example, when Salesforce announced Wave, we were one of the strategic partners there to drive data into their new Wave data analytics platform. >>>

Unicorn in The Making: Ross Mason, Founder of MuleSoft (Part 5)

Sramana Mitra: During this period when you had a lot of users and you didn’t have the model figured out, what experiments did you run to get to the heart of that issue—because the whole business is predicated upon that?

Ross Mason: No one has ever asked me that question and it’s a great question. I like it because we did have to experiment. We might be doing somewhere in the region of $4 million in revenue. It shows promise but we weren’t showing growth. Then the financial market crash got everyone spooked. Some of the analysts were saying, “The model was potentially going to harm our business because people were buying us but doing big architectures like SOA.” We really had to play around with it. What we did was started looking, very early on, at application ecosystems and what was changing there.

Even in 2007, we tried to do Mule On Demand. Salesforce is becoming very interesting, not just as a CRM, but as a way of delivering applications. We started toying around with the idea and that started to shape other things such as the way we would deliver connectors for applications within the cloud. Between the years 2009 to 2010 was when we realized that what we should be doing was to harness the changes that the cloud was bringing to market. >>>

Unicorn in The Making: Ross Mason, Founder of MuleSoft (Part 4)

Sramana Mitra: Ann actually told me that the person who first mentioned MuleSoft to her was an industry analyst from the banking sector who had heard that several banks were using MuleSoft. He told her about you and that’s when she started investigating and liked what she saw.

Ross Mason: I’m actually trying to remember his name. I had a very funny interaction with him. He mentioned that to Ann without ever speaking to me directly. I think Ann brokered a meeting with him. I think he was interested because he was hearing this name pop up and didn’t know anything about me. I stepped in and he was sitting at the restaurant. I went down to sit next to him. He looked quite confused at first. I said, “Hi, I’m Ross.” He just looked at me a bit. I looked so young and he was expecting someone so much older. He was completely confused that I was the guy that was creating this software.

Sramana Mitra: In 2006, how much did you raise?

Ross Mason: We did $4 million.
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Unicorn in The Making: Ross Mason, Founder of MuleSoft (Part 3)

Sramana Mitra: You decided to come back to London?

Ross Mason: Yes. On the way back, we went through the Pacific Islands. My wife said, “Let’s stop in San Francisco because we haven’t seen it. You talk about it a lot.” When I landed in San Francisco, there was this conference JavaOne, which was very big back then. So, I went there and I remember turning up at the Thirsty Bear bar. I was absolutely mowed down by lots of people who were using Mule and they didn’t know who I was. I stayed anonymous and kept a pretty low profile. My whole week after that went into meeting people in San Francisco who had known and were using Mule. It made me realize that there was an opportunity behind the open source project.

Sramana Mitra: Interesting. Are we talking 2006?
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Unicorn in The Making: Ross Mason, Founder of MuleSoft (Part 2)

Sramana Mitra: Were you working with other clients? Of course, you had deep insight into the problem with your experience but did you also work with other clients at that time?

Ross Mason: The way it came about was in 2003, I decided to leave the company I was working at and go traveling through South America to Australia. Before I went, one of the partners called me and said, “I heard you just left. I know you want to go traveling, but do you want to earn some money before you go? We have a project we’d like you to do.” I had a couple of months, so I figured why not.

They essentially were building a campaign management system for charity donations. >>>

Unicorn in The Making: Ross Mason, Founder of MuleSoft (Part 1)

Ross bootstrapped Mulesoft with a paycheck and also with services. Now, the company has raised over $130 million—the last round at an $800 million valuation. Very interesting story!

Sramana Mitra: Let’s start at the very beginning of your personal journey. Where are you from? Where were your born and raised?

Ross Mason: I was born in London and raised, up until about 9, in London. Then, we moved to Wales in the UK. I was in Wales with my parents who had a hotel and eventually, hotel chains. I grew up in a business. My dad himself is entrepreneurial. I got used to dealing with customers and thinking about what people need at a very young age. From there, I went to college in Bristol where I studied Computer Science. Fairly soon after that, I got into working with banks and insurance companies. My focus was always around solving difficult problems.

Sramana Mitra: Can you put a chronological framework around this? What year were you graduating from college? What year were you starting to get into the industry?
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Aiming to Dominate Real Estate Brokerage: Robert Reffkin, CEO of Urban Compass (Part 6)

Sramana Mitra: I think that’s only partially true because the level at which valuations are going out of control right now is way beyond the kind of rational justification that you presented.

Robert Reffkin: Uber has raised $40 billion. You can say that’s a huge valuation. If a majority of cars in the country are Uber, then it’s not. All you have to believe is one thing—that using Uber for a year for all of your transportation needs would be half the cost of owning your own car. If you believe that can happen, which is a very easy argument, then Uber will dominate transportation across the world. If they dominate transportation, there’s a lot of interrelated services that they can put on top of that.

Sramana Mitra: Let me give you a counter example. We just saw a complete implosion of Fab, which raised a lot of money and had similar kinds of grandiose rationale. Obviously, it did not play out. Investors were piling money on it until they imploded.
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