Lessons on writing and interviewing from a Modern Hemingway Journalist

“You can call me that, but it is totally untrue haha” -Jon Swartz

[in reaction to me calling him the “Modern Hemingway Journalist”]


It is rare for me to ever be amazed by someone, especially when it comes to writing. But when I was talking to Jon Swartz, one thought bubble popped into my head, “This is a Writer.”


For those of you who don’t know, he is a world renowned journalist based in Silicon Valley, and he has interviewed and befriended billionaires such as Steve Jobs and Bill Gates, as well as celebrities like Kevin Costner and David Letterman. He has worked for various esteemed magazines such as The Chronicle, Forbes, and now he is the chief journalist at USA Today. Besides being a journalist, he has also written a thrilling non-fiction book written in the style of a short story called “Zero Day Threat“, which reveals how unsafe the cyber world is in relation to stocks and other online resource. In other words, he is the real deal.


He is also a prolific writer. It is not unusual for him to be working on 7-10 stories at once, and so having “writer’s block” is not an option for him. But he is also a careful artisan. This man is someone who is full of harmonious inconsistencies, in the way that, although he burdens himself with a lot of pieces at once, he a lots his time so that he can cultivate the value in each of his pieces. Here’s an example of his writing here.


He visited my business class at UC Berkeley today(thanks to the connections of my professor), and he allowed us to ask whatever questions we wished, and he gifted us with his colorful stories and insights. And afterwords, we had a brief but meaningful conversation(more like an interview) about how he writes specifically, and his philosophies on the art of the interview. But before I get into that, allow me to tell you one thing about him that connects everything else that will come.


As soon as you see him, one thing is clear. The man is sincere. He is genuine in all his pursuits, and he honestly wants people to feel comfortable, and he honestly finds interest in other people’s lives. He actively searches for things in common(whether this be a trait gained from his life as a journalist, I don’t know), and he builds rapport. Now that you know that he is a good person, onto the juicy, protein-filled meat.


Jon Swartz’s rules for success as an interviewer and a writer.


  1. Never Go for the Jugular.
    Jon always makes sure that his interviewee is comfortable before he asks his questions.
  2. Do not have an agenda
    Jon doesn’t force the conversation in any direction, he allows the people he interviews to lead the conversation. Value becomes unearthed more easily by the interviewee. They know what they want to say, allow them to say it.
  3. Be Sincere
    Do not force yourself onto the person you’re interviewing, and don’t force a false persona, it will just make things awkward.
  4. Provide Value
    When Jon was interviewing Bill Gates, the way he opened him up was by telling him about something that Bill Gates did not know. That one statement opened up the entire interview, and became the basis of his next piece.
  5. Know the answer to the first question you ask.
    This means finding out beforehand what questions will open your interviewee up. Jon would often ask the interviewee’s handlers before the interview, in order to gain perspective on some of the questions he wanted to start with. And once he found the question that would get the most positive feedback, he would ask it.

Some of his Writing Habits.

  1. Carry something to write down your ideas.
    He constantly jots down phrases, ideas, and keywords on the notepad app on his iphone. He habitually looks back on his app throughout the day to help him connect some of his ideas and phrases together, in order to get a basis for a new feature.
  2. Eating Healthy and Exercise.
    This may not seem like a writing habit, but he explained how he beat “writer’s block”. His solution was simple and beautiful. He became calm. I could tell be the way he talked about running, that it was a very meditative experience for him. And he also contributed part of his calmness to the fact that he eats healthily and rarely drinks, and so he does not have any physical detriments to get in his way.
    The first thing you need to do in order to succeed is to get out of your own way.
  3. Minimize your Interaction with Negative People.
    Jon knows that a writer is not a writer only when he is sitting down and actually writing. To him, a writer is the culmination of the individuals interactions and experiences, and is anything hinders the individual from writing, it is because of the individuals interactions and experiences. And so, he is very meticulous with the people he spends his time with. He wants people that are positive and optimistic, so that his mind doesn’t have to be put under unnecessary stress.


I want to thank Jon for allowing me the interview, and it means a lot that he would help out the small guy(which is me).

I hope you guys liked this post, I sure learned a lot. Follow me for more~




Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s