3 MUSTS on landing a high-profile interview


Suit. No tie.

Casual shirt.


The dress of an entrepreneur. Somehow professional, yet disheveled. Yesterday, clad in this garb (sorry I know you want to see my beautiful self but I didn't take pictures) I took a train to NYC and hopped on the Subway to Rector Street, near the South Ferry.

A couple blocks down, near the South Ferry, I entered a tall, austere building and handed my ID to the guard at an elaborate granite desk. Up to the 9th floor I go to a co-working space.

I chit chat with the cute receptionist, who remarks to her friend who loves matcha after we talk about hot beverages. We chat about matcha then I sign in and wait for the ai startup CEO I heard speak back at Propeller Fest in June to come in for our interview.

Here are some things to learn in case you want to get to the same place I found myself around 1 pm:

1 - No matter how successful or famous your interviewee... They. Are. A. Person.

They are not a god

They are not perfect

They have emotions, desires, and lives like all of us

It's very easy to fall into the trap when interviewing successful people and celebrities of thinking they are perfect. With performers especially, their public image is tailored so minutely to support their on-stage act. With some businesspeople who brand themselves differently in professional life than their personal life, their public image is designed to inspire trust, confidence and their product.

Thankfully Dennis Mortensen barely had an ego and was quite transparent and genuine. That said, I knew going in that he was a person and I should treat him with the respect and realist honesty a person deserves.

For celebrities I imagine it's relieving to be seen as a person rather than a god. I have heard interviews where actors become lonely because after achieving fame, people only see them as gods, rather than actual people. Being put on a pedestal is just as distancing as social ostracization, but with the illusion of approval.

2 - Follow up. Follow up. Follow up.

I spoke to Dennis' assistant for 3 months before scheduling this interview. I reached out at first on August 21st. I gave examples of my work a few days later when asked for details.

There were a few moments where I had to follow up. Depending on your standing as a blogger, you have to understand and accept that you're not their priority, and depending on who you're interviewing, you likely have to reach out to them more than they reach out to you. Stay humble, don't demand things and understand that startups (and other high-profile interviews) have a lot on their plate and you easily might fall through the cracks if you don't remind them.

At one point in early September, the publicist even asked that I reach out later on, since they were swamped with work. I swallowed my pride, told them I'd reach out the week before Halloween, and set a reminder on my phone.

I imagine my laid back, understanding, yet true-to-myself demeanor earned me a lot of trust with them. Because I understood their needs and was willing to accommodate. It's easy to fall into the trap of thinking "I'm awesome, they should bow to me because I'm giving them publicity."

But honey, my most lucrative day on this blog so far was September 15th, where I got 50 views. That's absolutely nothing. They are giving me charity by donating 45 minutes of their CEO's time. I am in no fantasy land about what I am asking, and for me to sell it as something else would be gas-lighting. Which brings me to the 3rd tip:

3 - Know your place and be up front and honest

Had I lied about publishing his video on the web,

Had I lied about my blog's readership,

Had I sold myself as already making money with the blog,

I would have lost this. There would have been obvious distrust. He would have been expecting something much different. One thing that's easy to miss, but essential and simple is this belief:

People will almost always consider doing you a favor if you are up front with your intentions and aware of the weight of what you ask.

People will almost always consider doing you a favor if you are up front with your intentions and aware of the weight of what you ask. If it fits their values and they have the resources they might even grant you that favor! But the only thing you can push for is for them to consider it. Anything else and you're crossing the boundary into aggressive sales tactics.

Stay tuned for content from the interview, lessons from a highly successful startup CEO, and cereal.

(No joke. I went in with a joke question about cereal and got an unexpectedly and delightingly detailed response.)