Entrepreneurs are scrappy by nature. But not everyone sees this as a positive trait.
I’ve been criticized for the way I funded my first internet company. When no investor would bet on me, I called up J.Crew and asked, “Can I return all the clothes I bought when I was at New York University?”
The rep said, “Yes. We have a lifetime return policy.”
“Are you sure? I wore clothes throughout college. And I took the subway to school.”
She said, “Gladly. That’s our policy.”
So I mailed back all my old J.Crew clothes and got a few thousand dollars to start my company. The business generated over $30M in sales. I’ve been a loyal customer of J.Crew ever since.
When I published my story a few years back, entrepreneurs praised my hustle. But I also got the kind of criticism and insults that most people try to avoid.
This negative response is why some of my interviewees are hesitant to share their craftiest growth tactics. Still, as an interviewer, it’s my job to uncover those types of lessons. Otherwise, I would be sharing an incomplete picture with my audience. Without knowing the full story behind people’s success, we risk frustration and shame from attempting to be like them and falling short.
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So how could I get guests to open up about topics they were reluctant to discuss in public? My solution was to use icon stories to destigmatize those topics by drawing comparisons to their heroes.
Software entrepreneurs admire Matt Mullenweg, the founder of WordPress, because more than a third of websites are built with his software. But people are often shocked to learn that in the early days, Matt spammed websites to grow his business. As he explained in our interview, Matt went to blogs he liked and pitched his software in the comments.
Now, when I sense that a software founder isn’t sharing the full story of how they grew, I tell them how Matt got his first customers. By sharing Matt’s story, it takes the stigma out of it.
You can see this technique in action in my interview with Emmanuel Straschnov, creator of Bubble, the no-code app builder. When I asked him how he got his first customers, he talked about creating a community. My research showed the community he built was robust. But I wanted to learn a non-obvious way he landed customers, so I told him about Matt spamming. His response? “So I used to do that. I did that in the first two, three years when the product was not good enough.” Then he talked about why it didn’t work for him and gave us a deeper understanding of how he grew his company.
I’m always on the lookout for iconic stories like Matt’s. I write them down to help me remember to use them in my interviews. When I heard that investor Paul Graham said, “Startups often have to do slightly devious things,” I knew I spotted a helpful quote. When describing the investment philosophy for his firm, Y Combinator, Graham said, “We’re not looking for people who did what they were told in life.” I wrote that down too.
I use Paul’s lines in pre-interview conversations. They give me a quick way to show an upcoming guest that it’s OK to reveal the “slightly devious things” it takes to succeed. In fact, it’s preferable.
We’ll cover the pre-interview process in the next part. But first, I want to share another use for these icon stories—they help reassure a guest after they reveal something they might later regret.
You can see this in my interview with Ilya Lichtenstein, founder of the ad data platform MixRank. He told me a great story from the early days of his company. To get customers, he wrote a script that collected images from other successful online ads and gave them to his prospects to use for their ads. He copied thousands of businesses’ ad creatives en masse and used them to grow his company.
“Is that a potential copyright violation?” I asked.
He admitted it was “skirting the line.”
When a CEO of a data company says that, it presents a few dangers to the interview. The most immediate one is that he’ll clam up and stop revealing more. But there’s also a danger that the audience might turn against him. Both of those outcomes are anathema to my goal of sharing how founders really build their companies. So I followed up his answer by repeating Paul’s quote about being devious. Ilya responded, “Yeah, I think that falls into the slightly devious category.” The conversation moved on, and the audience’s reaction was positive.
If you’re trying to create an atmosphere where your interviewees can reveal the hidden parts of themselves, show them how their idols did it. When you come across a quote or story that illustrates it, keep it handy.