Life was good. Craig had a blossoming reputation in an established firm. His on-target earnings (OTE) were in the six figures -- and he was tripling his targets. At 26 years old, Craig was making a very good living.
Most young people at this point would start elevating their lifestyle expenditures to match the income. Yet, in the back of Craig’s mind, he knew he’d start a company and would need a nest egg to lean on.
His vision overpowered his ego and he kept his expenses low.
During a club trip, Craig started discussing with one of the more senior guys about starting a business. The senior rep said to Craig: “I couldn’t even fathom starting a business, I’d need $100,000 just to pay my bills.”
Vision and reality touched paths, and he knew he had to stay lean, because his future ambitions required it.
----
JB: So why didn’t you go start a business right after that conversation?
CH: Good question. I remember thinking to myself, “so what am I going to do next?” I mean, this may sound weird, but my job was so easy. All I did was fly around the country, talk about technology, and bang on the keyboard, while making really good money. It was so fun, and up my alley. It suited my strengths. I liked the people I worked with, but always in the back of my mind, I was like “now what?” My boss had been there a decade, his boss had been there a decade and a half, her boss had been there for 30 years, and then there was the CEO. So I’m like, okay, do I run on this hamster wheel for the next 10-20 years, for a chance to get to the next level up, or 30 years where you actually have impact, or what do I do? I didn’t want to coast in my life for the next 20 years. I felt like I had learned the most from the job I was going to learn, after two years. So I started to look at going back to grad school.
JB: You achieved what many would call the dream lifestyle, but yet you weren’t satisfied?
CH: Yeah, it was a really weird feeling. The company had been the same for the past 30 years. Nothing was changing, or going to change. It was less about the dream lifestyle -- it was more about answering the question: What am I doing with my life? I knew what I wasn’t doing: working on any new problems. It was rinse and repeat.
----
At this point, Craig made the decision to be proactive in his search to start a company. He was 27 years old at the time, and it had been in the back of his mind for years. It was time to take action, and the decision was made.
JB: Knowing what you learned from your MMA gym, how did you decide what market to start a company?
CH: Funny you ask. My roommate came home from work one day, complaining that he was trying to buy a gift card for a customer success person that helped him out on an account. He was like, “I can’t find a place online to buy gift cards.” And I was like “if you are looking for gift cards, one of the companies I’m working with has all the gift cards you could need, from a wholesale perspective.” So our idea was born: create an online storefront for gift cards. My roommate at the time, Jordan Rackie, was an Account Executive at Pardot. He said: “my CEO is a big entrepreneur, why don’t we talk to him about that.” And then I said: “Alright, let’s do it.” So Jordan brought me in to meet David Cummings in the Pardot office in 2010. The energy of what they were building at Pardot was incredible.
JB: How was your first “pitch” to then Pardot CEO, David Cummings?
It was more of a conversation. Jordan and I told him about our gift cards idea, and he was like “I like software companies, I don’t really do e-commerce, it’s just not what I know.” And in the conversation, we ended up talking about my experiences and business software I enjoyed. We talked even more about one of an acquisition my company recently had with a SaaS company. Long story short, we left the meeting with no next steps. David didn’t do e-commerce, I went back to my regular job, and Jordan went back to selling Pardot.
I followed up with him a few days later with an article about a company in the space. We ended up going back and forth a fair amount about the market. In one of those emails back and forth, he just asked: “how interested are you in starting a startup?” And I remember replying back “it’s the only option in the long run, I just don’t want to sell my house and move in with my mom while getting it off the ground, so I want to wait until I have customers.” Then David said something like: “from my experience, going all-in is the best option.” And it morphed into: “if you want to start this company, I’ll back it. How much do you need to get started?”