When you consistently derive value from someone’s work, I think you should pay it forward. That’s how I feel about Jason Feifer, Editor-in-Chief of Entrepreneur magazine, author, podcast host, and one of the most straightforward and relatable voices out there when it comes to business and self-improvement. I’ve followed Jason’s work for years—listened to his podcast, consumed his social media content, read his book—and all of it has delivered real value to me, often at little or no cost. So when he launched a paid community, I didn’t hesitate. I happily joined. Not because I thought I’d have the time to make every call or dive into every piece of content, but as a thank you. It was my way of saying, “I’ve taken a lot from your work—let me give something back.”

The thing I appreciate most about Jason’s content is how he takes complex ideas and breaks them down into digestible bites. He doesn’t overcomplicate things, but instead gives you practical insights that you can actually use. In fact, if you’ve followed his work, you already know how he sees it because he’s constantly showing us and telling us through his content. That’s why I knew he’d be ideal for this.

A few months ago, Jason announced that he’d be offering 15-minute one-on-one calls to the first five people in his community who responded. It was framed as an opportunity to ask him for entrepreneurial advice, but I saw it differently. I saw it as a chance to flip the script, take a shot, and ask Jason to share his experiences and how he sees life in areas he doesn’t often get asked about. Instead of asking about business and entrepreneurship, I wanted to dive into the six pillars I focus on with Midlife Male—Family, Fitness, Finance, Food, Fashion, and Fun. 

This was the first time I’d met Jason and the first time we’d spoken.  Sometimes, you gotta get creative and shoot your shot.

I’ve always believed there’s something to be gained by taking the business guy and asking him about health and family, or flipping it and asking the fit guy about money and relationships. It pushes people out of their typical lanes and into a space where their answers feel more raw, more reflective, and more revealing. I wanted to hear Jason’s thoughts on the areas we don’t normally hear about, not just so I could learn from him, but so I could share that perspective with all of you here.

What excites me most about this interview is the chance to step back and really see how Jason’s perspective has evolved over time. He’s built a career combining personal passion with professional expertise, and it’s clear that his views on the 6F’s—how he prioritizes and allocates his time, energy, and resources—have matured as he’s grown. You’re going to enjoy this conversation. 

– Greg

“How I See It” with Jason Feifer

MLM: Jason, first off, thank you for taking the time to do this. I run a lifestyle platform called Midlife Male, and I focus on six key areas of life—Family, Fitness, Finance, Food, Fashion, and Fun. I’d love to hear your thoughts on each of these from your perspective. Let’s start with family. How do you see it? What’s your philosophy on family?

Jason Feifer: My perspective on family is deeply rooted in my own experience. I came from a very loving, supportive family. My parents just celebrated their 48th anniversary, and I’ve always admired the relationship they built. Growing up in that environment, I was easily programmed to want to replicate it. I didn’t challenge or rethink it; I just assumed that because it was good, I would replicate it.

The downside to replicating something that didn’t contain a lot of hardship is that you might take it for granted. You might not think as much about how to build it or make it work. I have friends who came from broken homes and have had to be incredibly intentional about how they build their relationships, while for me, it feels almost natural, given my upbringing.

Now, with a wife and two kids of my own, I find myself repeating what my parents did. I see the great success that my family had, and I’m fortunate to have had those models to follow. I think that’s my philosophy on family—replicating what worked and appreciating what I was given.

MLM: Let’s move on to fitness, which is really about health. How do you see fitness? What’s your approach?

Jason Feifer: Fitness is something I’ve struggled to define for myself. I don’t feel particularly authoritative on the subject, and I certainly don’t have all the answers. But I know that I need to do better. At 44, I realize that I need to devote more time to my health, and I’ve been trying to make small steps to get there.

Recently, I decided to downshift on desserts. My wife and I used to sit down after the kids went to bed and have bowls of ice cream while watching TV. Now, I’m only doing social desserts—if there’s dessert as part of a larger social experience, I’ll have it. But I’m cutting out the mindless snacking.

I also got a rucksack from GORUCK and have been trying to incorporate longer walks into my routine. It’s all about baby steps for me right now, and that’s how I see fitness for myself at this stage of my life.

MLM: I love that. Baby steps are key, and the rucksack is a great tool. How do you approach food and nutrition?

Jason Feifer: My relationship with food is unique. I literally don’t have a sense of smell or taste, which has been the case since childhood, so I’m not that motivated by food. I can turn on a dime when it comes to food—I have no cravings. For me, food is primarily about being social or convenient.

My diet is pretty standard. For breakfast, I have a toaster waffle with peanut butter and sliced banana. Lunch is usually Greek yogurt with a tiny amount of jam and a slice of bread with peanut butter. Dinner is where my wife takes over—she loves cooking, and I appreciate the balanced, healthy meals she prepares. Last night, we had salmon.

I don’t snack during the day, and as I mentioned earlier, I only do social desserts. That’s my approach to food—it’s simple, social, and convenient.

MLM: It’s amazing how you’ve tailored your approach to food given your unique circumstances. Let’s move on to finance. For a lot of men in midlife, finance is a touchy subject. How do you see it?

Jason Feifer: Finance is indeed a touchy topic, especially for men in middle age. I did the opposite of what many people do—I didn’t spend the early part of my career chasing titles or money. Instead, I chased mission. I was very oriented towards being a journalist, which doesn’t pay well at all, but I found it to be a valuable contribution to society. So, I spent the first couple of decades trading financial value for personal satisfaction.

Lately, I’ve discovered that the thing I liked about journalism has evolved. It’s not so much about journalism itself anymore, but about using the skills I’ve developed to absorb information and translate it into useful, relatable ways for others. This has opened up opportunities for me to build in ways that do make more money.

I’m not motivated by money in the sense of needing to have it all. I have a specific number in my head of what I want to bring in so that my family is comfortable and we don’t have to worry about money. To me, money is about freedom. I remember talking to a billionaire who said there’s no difference between having one billion and five billion dollars—long ago, you already had everything you need. That resonates with me. You don’t need a billion dollars to reach that point. The number is much lower.

So, I’m focused on autonomy and freedom, and I understand the financial needs that help me get there. That’s how finance fits into my life.

MLM: I’ve noticed you have a distinct personal style—how do you approach fashion?

Jason Feifer: Fashion has never been a significant concern for me. I recognize that what you wear says something about you, but I don’t give it much thought. The most important thing about fashion is that you’re intentional about it—just that you’re making a decision. I’ve always been a casual guy, and I prefer to be comfortable.

The best advice I ever received about fashion came when I was at Fast Company. I was learning to be on video and asked the director, Scott, what I should wear. He said, “Wear whatever makes you comfortable because the most important thing when you’re on camera is that you’re comfortable. Comfort is what people will see, more than the clothing.” That advice stuck with me.

I’m most comfortable in a t-shirt and jeans or shorts, and I want to show up as the best version of myself wherever I go. That’s why I wear what allows me to inhabit my skin the best. Whether I’m doing a corporate keynote or appearing on TV, I show up in a t-shirt. If someone needs me to dress up, I’ll do it, but my focus is on comfort, truth, and intentionality.

MLM: Lastly, let’s talk about fun. It can sound juvenile, but it’s important. How do you see fun?

Jason Feifer: Fun has evolved for me over time. There was a period when I thought I was having fun, but I wasn’t. I associated fun with drinking, entertaining clients, and trying to play golf. But those things were exhausting and unfulfilling. Over time, I’ve found different kinds of fun that are truly enjoyable and positive.

For me, fun is all about other people. The great tension in my life right now is that I’ve created so much busyness that I don’t have as much time for other people. I’m often in front of the computer every day or traveling for work, which doesn’t leave time for what I enjoy most—spending time with people, kicking around ideas, and building relationships.

I’m an extrovert, and I draw energy from others. That’s what fun is for me. I also enjoy travel, going to basketball games, and concerts, though it’s harder to do those things with little kids. I recently saw Green Day, and it was a powerful reminder of how much joy those experiences bring.

My goal is to reach a point where I feel comfortable walking away from the computer at 4:30 PM every day to meet someone or do something fun. I’m not there yet, but I’m working on it.