From Homeless to Millionaire – Lessons Learned Along the Way with Mark Silverman

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Show Notes:

Meet Mark J. Silverman. Mark is an executive coach who helps CEOs and Senior Leadership teams focus on making sure the right work gets done in their organization. He’s also a speaker, podcaster, and book author.

Is your to-do list helpful or stressful? Our guest will tell you how to make it work for you.

Mark’s bestselling book called ‘Only 10s 2.0 – Confront Your To-Do List, Transform Your Life’ was sold in over 70,000 copies to this date. In his coaching, he helps leaders address the underlying behaviors and mindsets that sabotage all time management and productivity tools. Mark is all about practicing what he preaches. When he was 27, he was homeless, 135lbs, and living in his truck.

By the time he was 33, he was a millionaire. Now, he’s on a mission to share the lessons learned along the way and help others define and achieve their own successes.

In this episode of the Think Business with Tyler podcast, we talk about the importance of finding your motivation, why leaders need to focus more on coaching than on doing, how to get your to-do list in order, and finally, the importance of finding time to just sit with yourself.

If you want to make the most out of your to-do lists and other productivity tools, this episode is perfect for you!



💡 Name: Mark J. Silverman

💡 What he does: He’s an Executive Coach, Speaker, Podcaster, and Author.

💡 Noteworthy: He is the author of the Bestselling “Only 10s 2.0 – Confront Your To-Do List, Transform Your Life” which has sold over 70,000 copies to date.

💡 Key Quote: “The more you climb up the ladder, the bigger your company gets, the less your job is to do, the more your job is to coach. And most leaders balk at that.”

💡 Where to find Mark: LinkedIn

Key Insights

Find your motivation. Your motivation is that inner force that drives you to achieve your goals and keep going even when things get tough. But if you don’t know what your motivation is, it’s very hard to build the life you want. The sooner you find your motivation, the better. Mark explains,

“What happens is that, for me, the drives and motivations in your twenties and thirties that get you to that success in your forties and fifties start to crack. So you start to see, ‘Oh, I’m only a lawyer because my parents wanted me to be a lawyer.’ That whole thing, I climbed the ladder, and the ladder is on the wrong building. So then if you don’t listen to it, so that’s the whole midlife crisis thing for me is if you don’t listen to the whisper of ‘You know this is unsustainable’ or ‘You know this really isn’t what you want to be doing’ or ‘You know that you need to do things differently and make a shift.’”

The bigger your company gets, the less your job is to do and the more it is to coach. When you become a leader, your job is not to do anymore; it is to coach. Your job is to lead others and help them become the best versions of themselves. According to Mark, some CEOs have a harder time accepting this new reality, but it is extremely important to put the coaching hat on as soon as possible. He says,

“The more you climb up the ladder, the bigger your company gets, the less your job is to do, the more your job is to coach. And most leaders balk at that. ‘Why do I have to spend so much time coddling people?’ Because that’s your job now. Because you have humans who are dealing with COVID. You’re dealing with humans who watch Fox news and MSNBC and hate each other. You have people who have families who are dealing with stuff. You have people who have their own stuff. You just have to do that. Once you accept that your job is to coach people into the most successful versions of themselves, now you’re creating new leaders in your organization.”

Get your priorities in order. If your to-do list is a mess, it means you don’t have your priorities in order. A to-do list should have the most important tasks at the top and the least important tasks at the bottom. But easier said than done. Mark shares an interesting rule called ‘Only 10s’ to help you get your to-do list in order. He explains,

“10s mean kind of like Derek Sivers wrote a book and his concept was ‘hell yes or hell no.’ There’s no hell maybes. It’s either a 10, or you don’t do it. So 1 through 9s have to get thrown off the book. So I have people put everything on their to-do list 1  through 10, and then the 1s and 2s absolutely throw them out. The 4, 5, 6s, sometimes throw them out.”

Always have time to sit with yourself. We live in the world of distractions, so it’s no wonder we can’t stay focused anymore. That’s why it’s important to have an intentional taking back of our attention. Mark suggests coming up with a contemplation practice. He explains,

“You must have a contemplation practice. So, I work with New York finance guys whose legs are bouncing a million miles an hour, and they’ll never sit and meditate or anything like that, but you have to have a time where you sit, and you be with yourself. You sit and breathe. So even if you can’t meditate, if you can’t journal, go sit and have a cup of coffee, put your phone aside and just look out the window for five minutes, but you have to learn how to have that homing device.”

Top Quotes


“It was a really interesting juxtaposition from who I saw myself to be and always trying to prove that I wasn’t this homeless loser guy. So all that effort went into never being seen as the homeless loser guy again, so we’ll talk about that later, how it’s unsustainable. That drive to success it’s often from something really unhealthy. I’ve never met an Uber wildly, amazingly successful person who didn’t have some kind of pathology drive in that.”

“Remember what I was saying is that motivation turned on me. So my career was destroyed. My marriage was destroyed. My health was destroyed. I was even diagnosed that I was going to die. There’s always drama in my there’s all this drama in my story. Now I have no zero drama in my life whatsoever.”

“I don’t know if you’ve heard of Robert Kegan’s Competing Commitments, the immunity to change. So the Competing Commitments, there’s this thing inside, like ‘You should do this, and you said you were going to do this,’ but inside you’re like, ‘I don’t really want to’ and now you’ve got to find a different motivation and you’ve got to figure out.”

“It’s not really our fault that we can’t pay attention anymore. Everything is coming at us at such a rate, our emails, our texts, the news. You can’t go into a restaurant without having three news stations on the thing and then sports and all that stuff. So it really has to be a deliberate, forceful taking back of your attention.”

“Most of my clients are hyper-responsible. Over responsible. They care about everything. Everything is a 10, and I’m like, ‘You’re going to kill yourself. If you go into the leadership team meetings and everything is a 10, and you have to fight for everything, nobody’s going to take you seriously. You’re going to exhaust yourself.’”


Only 10s 2.0 – Confront Your To-Do List, Transform Your Life by Mark J. Silverman

Stolen Focus by Johann Hari

Mark J. Silverman Website


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