MLM Issue 13: ‘How I See It’ w/ the "Face of Failure" Suneel Gupta, plus...

Morning, Greg here! Welcome to Issue No. 13 of Midlife Male, the lifestyle magazine for midlife men, by midlife men. I wanted to personally welcome all our new readers, and if this newsletter was forwarded to you, subscribe below.

This week we've got a new How I See It, a Viewpoint column on the price of midlife success, recommendations for each of our 6 Fs and more. And if you’re looking to finish the year strong, and start ‘25 off even stronger, I'm opening up a few coaching spots. Click HERE to set up a FREE discovery call.

Once dubbed the “face of failure” by The New York Times, Suneel Gupta turned setbacks into stepping stones for success. He became the founding CEO of RISE, a wellness company named Apple’s App of the Year. 

Now a bestselling author, renowned speaker, Harvard Medical School visiting scholar, and host of a global documentary series, Suneel studies top leaders worldwide to uncover actionable habits that boost performance and enhance well-being. His journey illustrates the power of resilience and the transformative potential of learning from failure.

‘How I See It‘ with Suneel Gupta

This week, we have Suneel Gupta in our How I See It interview. Suneel is the author of Backable, a book I read a couple of years ago that really changed my perspective on how I saw myself, as well as the more recent Everyday Dharma.

Backable pushed me to ask some hard questions: Am I backable as a husband, father, provider, and man?  Would I invest in me? And in the areas where I was coming up short, what do I need to do, change, and transform in order to become backable? Suneel’s insights not only shaped the way I approach my work but also how I approach my entire life and the relationships that matter most to me. - Greg

Greg Scheinman: We met about three or four years ago in Detroit at Three Ring Circus, which is now Impact 11. It was a speaker’s boot camp, right?

Suneel Gupta: Yeah, that’s right. I remember you telling me about your premise and what you were working on, and I thought to myself, "Wow, I need that. I’m a midlife male—let me tune into this podcast immediately." And Greg, I’ve got to say, your stuff is great. It’s helping a lot of people, including me.

Greg Scheinman: Well, thank you for saying that. The feeling is mutual. I remember how many incredible people we had in that room, all at the top of their game in their respective industries and lives. Yet, we were all very new to the speaking industry, which is why we were there—to find our voice and learn how to reach more people. At the time, you were talking about being backable, and I'd love to dive into that concept. For me, a lot of my personal growth came from not feeling "backable" and wondering how to transition into that state. Can you talk about what it means to be a "backable" man?

Suneel Gupta: Sure. I felt the same way—like I wasn’t backable. I realized this after pitching my startup idea to over a dozen investors and getting rejected each time. I began wondering, "Is it the idea or the way I’m explaining it?" What are we really betting on when we bet on someone? This question doesn’t just apply to venture capital; it applies to life—our careers, communities, friendships, and family relationships. We constantly take chances on people, and I wanted to understand the habits of those who seem to succeed naturally. Are they born with it, or is it learned?

About ten years ago, The New York Times did an article on failure, and I was the face of it. I had started two companies that failed, and I was also part of Groupon, which had a meteoric rise and fall. So, I became the poster child for failure. I even used that article, with a mentor’s advice, to reach out to successful people for guidance. I sent the article to filmmakers, celebrity chefs, and sports coaches with a message saying, "I don’t know what I’m doing—can you help?" To my surprise, the response was overwhelmingly positive. People were willing to connect with me, not because I was successful, but because I was vulnerable. That vulnerability paved the way for Backable and later, Everyday Dharma.

Greg Scheinman: That’s fascinating, and it really struck a chord with me. So many of us go through life hitting goals but feeling like something is missing—whether it's in family, fitness, finances, or just everyday fulfillment. It’s that nagging sense of mediocrity, even when things look great from the outside. Can you talk about how that sense of mediocrity ties into the concept of purpose?

Suneel Gupta: Absolutely. There’s a concept called "the arrival fallacy," coined by Dr. Tal Ben-Shahar. It’s the belief that once we achieve success—whether it’s wealth, status, or a specific goal—we’ll finally be fulfilled. But what happens is the goalpost keeps moving. We think it’ll be the next deal, the next car, the next house, but once we get it, the happiness is fleeting, and we’re left wondering, "What’s next?" 

For me, after I finally started a successful company and sold it, I thought, "This is it!" But that feeling didn’t last. And that’s where the concept of Dharma comes in—it’s about connecting who you are with what you do. Dharma isn’t about quitting your job and chasing some grand vision. It’s about finding the small sparks in your daily life that bring you joy, doubling down on those, and fanning them into something bigger.

Greg Scheinman: Does that mean you always have to align your purpose with your profession? What if you can’t quit your job or radically change your life?

Suneel Gupta: No, you don’t have to quit your job to find purpose. That’s a misconception. Purpose isn’t about flipping off your boss and moving to a mountaintop. It’s about finding those small embers of joy in your current life and nurturing them. You might not be able to change everything overnight, but you can lean into the moments that give you energy. For example, there’s a nurse I know who found joy in filling out patient paperwork because she personalized it, writing not just clinical details but human details about the patients. That simple act sparked joy for her, and it impacted everyone who read her notes. She didn’t quit her job—she just found purpose in the details.

Hard Truths About the Cost of Success (What Are You Willing to Give Up?)

Years ago I had a client tell me that he hadn’t been out of the office for more than a week in nine years. I had to ask him—was he proud of this, or regretful? He’s a multimillionaire. He’s also divorced, had an affair with a woman at the office, and is now alone in his 50s.

I think about him sometimes, especially when I hear men talk about what success looks like. On paper, he has it all. But when you strip away the accolades and the balance sheets, what remains? His life became a singular pursuit, a marathon of work without a pause, and in the end, it cost him the things that couldn’t be measured in dollars. It makes you wonder, what’s the real currency of success?

Another friend—who’s married to a major celebrity,  just posted publicly that last week was the first time he’d been away with his wife for more than a weekend alone since their honeymoon. Think about that for a second. That’s almost three decades of a life so busy, so filled with obligations, demands, and the pursuit of success, that they never took the time to truly be together. And for what? Fame? Adulation? Influence? What’s it all worth when the person next to you, the person you’ve chosen to spend your life with, barely knows who you are anymore? The dichotomy was that this was supposed to be an announcement that the doors are now finally open to more of this. 

Just yesterday, I read a post from a friend whose son I coached in Little League. He wrote about his retirement after 33 years with Pennzoil and Shell Lubricants. It was a nostalgic post—full of pride in the roles he’d held, from a young process engineer to plant manager at one of the largest production facilities in the world. He thanked the countless people he worked with over the years, acknowledged the impact they had on him. But when I read it, all I could think about was 33 years of waking up every day to go to work for the same company, making lubricants. Three decades of routine, of showing up, of doing the job.

On the surface, it’s another success story. A career well-lived. A job well-done. But beneath it, there’s that lingering question—what did it cost? What did he give up to spend three decades in the same industry, waking up every day to the same job? I wonder what his mornings feel like now, without the rhythm of work to guide him. Does he feel liberated, or lost?

Millions of stories are posted online every day and 99.9% are noise. We sifted through the nonsense to share standouts with actionable takeaways you can use to maximize your life in each of our 6Fs: Fitness. Family. Finance. Food. Fashion. Fun. Let’s go.

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FAMILY - Forget Delivery - This $600 Pizza Oven Brings the Whole Family Together

FITNESS - Tired of Treadmills & Pelotons? We Love the Concept2 SkiErg for a Cardio Change of Pace

FINANCE - The 8 Biggest Financial Mistakes Men Make

FASHION - Overcome the Dad Hat Dilemma with High Quality Headwear

FOOD - You’re a Man: Stop Using Dull Knives

FUN - The Case for Dropping $1,200+ on World Series Tickets

Listen to the audio book of Midlife Male, read by author/founder Greg Scheinman, on Audible today!

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