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- Five Great Books: Homeless to Billionaire, The Dark Side of Discipline, Dying to Do Letterman, and More!
Five Great Books: Homeless to Billionaire, The Dark Side of Discipline, Dying to Do Letterman, and More!
Matt Karamazov
November 29, 2025 ā¢ Estimated Reading Time: 27 minutes
YOUTUBE š CREATOR LAUNCH ACADEMY š PATREON
Hey, Iām back with five more great books to recommend tonight.
If thereās a common theme to my selections tonight, Iād say that this is a newsletter about dreams.
Here weāve got the incredible story of Andres Pira, who went from sleeping on a beach in Thailand, to becoming a billionaire (Homeless to Billionaire).
Weāve got the inspiring story of Steve Mazan, who, after doctors gave him five years to live (when he was in his mid-thirties), started chasing after his dream of performing comedy on David Letterman with renewed vigor and intensity (Dying to Do Letterman).
And weāve got three other great books that will help you chase down your dreams, by helping you buy back your time, defeat procrastination, and conquer self-discipline (Buy Back Your Time, Do the Hard Things First, and The Dark Side of Discipline).
I also want to let you in a little dream that Iām chasing this yearā¦
In just 123 days from now (April 1st, 2026), Iāll be putting a deposit down on this 2017 Lamborghini Huracan that I found on the East Coast.
Iād say my chances of making it happen sit at around 90%, so itās not a far-off dream, but it will definitely be a stretch. Iām not loaded or anything, but Iām already a moderately successful, full-time book influencer with tons of opportunities coming at me every day.
But Iām also not just doing it for me, although of course Iām buying it mostly for me!
The fact is that reading is once again in grave danger.
I donāt want to say that ānobody reads books anymore,ā because thatās obviously not true, but we need to make books cool again, and that means showing people how amazing our lives can become if we become dedicated readers.
Of course, there are plenty of people out there who lead fantastic, non-flashy lives, and who credit books with changing their lives. Not everybody needs or wants a Lambo!
But I know that I can inspire more people to pick up a book instead of their phone, if I can show them that reading books is exciting and awesome. Not some boring thing, or a chore they have to somehow āget through.ā
So thatās what Iām doing. Iāve given myself this 123-day deadline to sign the purchase agreement on this Lamborghini Huracan, and Iām going to give it everything Iāve got.
Here in this newsletter though, Iām sharing my complete notes and summaries of each of the following Five Books:
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When you do sign up, join my book club on the app! Itās called āThe Reading Life.ā
In This Issue of The Reading Life, Weāve Also Got:
š What Iām Currently Reading
š Books Iāve Finished This Month
š The Book Quote of the Day
š„ 10 Great Books to Help You Solve 10 MAJOR Problems
ā My Latest Medium Articles
ā New Book Releases Coming Soon
š Tonightās Five Main Book Recommendations
š Earn Rewards for Referring This Newsletter
Letās not wait for our coffees to get coldā¦letās hit the books!
The Library: A Fragile History, by Andrew Pettegree and Arthur der Weduwen: The titleās pretty self-explanatory here: itās a history of libraries, from the earliest discovery of the written word, right up until today.
One of the most striking things about this one is just how endangered reading and writing have been at various times in human history, and how libraries and the written word have always survived. Books have always made a comeback!
The Rothschilds: A Family Portrait, by Frederic Morton: This is a multi-generational history of the Rothschild banking family, how the original patriarch of the family started off in the Jewish ghetto of Frankfurt and how his descendants basically took over the entire financial world (and are now, literally, shadowy trillionaires).
Itās endlessly fascinating so far, and also quite funny! I wasnāt expecting that! It came out a long time ago though, and Iād definitely be interested in following up my reading with some more contemporary sources.
After achieving my (somewhat meaningless) goal of reading 1,000 books before I turned 30, I set a new (also meaningless but cool) goal of reading 10,000 books. As of today, Iāve read exactly 1,432 books, including 80 books so far this year, and if youāre interested, hereās my full Reading List.
āThe brick walls are there to give us a chance to show how badly we want something.ā
10 Great Books to Help You Solve 10 MAJOR Problems: I used to have all ten of these problems myself. But then, I read and applied these ten great books, and now I donāt have those problems anymore!
I mean, I still have 99 problems, but now, a book aināt one! So if you often have too much month left at the end of your money, you keep getting passed over for promotions, youāre scared of public speaking, or youāre battling a crisis of meaning, these books will help! [Watch Time: 11:56]
If you enjoy the video, please consider subscribing to my channel and sharing it with a friend. Cheers!
āStatus Anxietyā is the Source of Your Paralyzing Fear of Never Having Enough: And this fantastic book is the antidote (14 key takeaways).
The Business Book That Helped Me Buy My First Porsche: Ignore the scammy title - this book took me from minimum wage to financial freedom in 5 years flat.
The Saddest AND Funniest Book Iāve Ever Read is Also One of the Most Challenging Books of All Time: 39 flashes of brilliance from Infinite Jest thatāll make you think, laugh, cry - and probably all three at once.
Beyond Belief, by Nir Eyal: Iāve read two of Nirās books so far, and so Iām eagerly awaiting this one, which is about science-backed ways to stop limiting yourself and achieve breakthrough results. Naturally, Iāve read plenty of books on the subject already, but I know that Iām going to come away with tons more here that I can use immediately. Expected: March 10th, 2026
Protocols, by Dr. Andrew Huberman: Still a long way to go before this one comes out, but itāll be an essential guide to improving brain function, enhancing mood and energy, optimizing your health in all kinds of ways, and rewiring your nervous system for high performance and a better life. Expected: September 15th, 2026
Whatās Stopping You?, by Timothy Armoo: I was hoping Timo would come out with a book of his own, because not only does he have great book recommendations of his own, but heās on his way to becoming a legendary entrepreneur. His first book offers 11 cheat codes to unlock the life you want. Expected: January 15th, 2026
āOnce you clearly see where youāre spending your time, youāll want to buy it back.ā
Your time is for sale, and you can buy it back at bargain basement prices if you have Dan Martellās playbook. This book contains the exact systems and processes he used to build a $100M holding company, and it helped me read a lot more books, so they can work for a wide variety of people!
One of the most useful calculations in the book concerns your āBuy Back Rate,ā meaning the dollar value you assign to your time.
Briefly, if thereās a task that someone else can do pretty much as well as you can, for less than your hourly rate, you offload it to someone else. Thatās a fairly simple one, and lots of time management books cover it, but thereās a lot more in here too, like the DRIP Matrix, the 1:3:1 Rule, and others.
Bottom line, though, Buy Back Your Time is about finding creative and profitable ways to use a readily-available renewable resource (money) to reclaim the most valuable non-renewable resource in the entire freaking universe: your time.
Business owners and professionals are likely to derive the most value from this book, as thatās where the majority of Danās experience comes from.
I mean heās got three software company exits to his name, an AI incubator heās started, a massive social media following - the dudeās busy, I guess is what Iām trying to say. And this is the system he uses personally and professionally to manage it all without sacrificing the moments that matter most.
āThe more you procrastinate, the more you pay.ā
One of the biggest things that used to hold me back from achieving everything I envisioned was the illusion that I would still have time later; that I could leave something for ātomorrowā and live for today.
While thereās something to be said for living in the moment, I didnāt want to waste my most productive, active, and energetic years looking back from the other side of 40 at everything I could have been. So I read this book.
Do the Hard Things First will help you develop a productive sense of urgency. Itāll give you this level of focus and relentlessness you need to beat procrastination, control Shiny Object Syndrome, prioritize effectively, and build a powerful work ethic based on a solid sense of self-worth and a clear idea of your main vision.
A few takeaways stand out as being particularly motivating. For one thing, Scott Allan asks how youād feel if, at the end of your life, someone offered to give you 1,000 hours back. Hours that most people wasted this very year.
Recently to this writing, Iāve attached the same value to my minutes as the Pink Star diamond fetched at auction: $71.2 million. Literally. When Iām deciding where and how to spend a single minute of my time, I ask myself whether Iād be willing to spend $71.2 million on whatever it is Iām planning to do.
While thereās nothing so extreme in Do the Hard Things First, I truly believe thatās how highly each individual needs to value their time. The strategies and mindsets in this book will help you start thinking along those lines.
Theyāll help you respect yourself enough to place an exceedingly high value on your time. And armed with the tactics presented here, youāll be well-protected against death-bed regrets about how you spent that limited time.
āNone of us wanted to make a sad sack, sappy movie about cancer. I was a comic. I wanted to face everything with humor. Thereād surely be down times, but thatās not what we wanted to focus on. We wanted to make a movie about dreams.ā
I canāt even remember what caused me to click on Steve Mazanās TEDx Talk a few years ago, but what I do remember is his insanely inspiring story and his insistence that āSomedayā is not a day on the calendar.
Thereās a Monday, Tuesday, Wednesday, Thursday, Friday, Saturday, and Sunday, but no Someday. And yetā¦Someday is the busiest day of the week.
Everyone seems to be waiting for āSomedayā to start chasing their dreams and going after everything they really want in this life. But Someday never comes. And unfortunately for Steve, a professional comedian who once dreamed of performing on David Letterman, inoperable liver cancer came for him first.
In his early thirties, doctors gave him five years to live (the possibility of living for 15 years was framed as āgood newsā), and it dawned on Steve that heād never really taken his own dreams seriously. And now it might be too late.
But like he says in the book description, after getting the devastating diagnosis, Steve did something strange. He started living. He started taking this āLetterman thingā seriously - or rather, taking it sincerely - and he made the conscious, courageous decision to give this dream everything he had during the time he had left.
It took me two years from the time I first watched Steveās TEDx Talk before I finally bought and finished reading his book. Two years that I loved living, certainly, but two years where I didnāt give everything to my dreams. I know that I didn't, because Dying to Do Letterman kicked me into the highest gear Iāve been able to access so far.
I donāt want to oversell it. Steveās book is funny and motivating and it shatters the illusion that you and I still have time to waste not chasing our dreams. But I realize that itās not going to be everybodyās thing.
That being said, itās well worth the price of the book if it simply inspires you to ask yourself - daily, often, constantly, as often as possible - one of the most powerful questions Iāve ever heard: What are you dying to do?
āAt one of my lowest points, I discovered the power of knowledge through a book. By studying, learning, and putting into action the knowledge Iāve acquired from many books, I turned my āsurvival lifestyleā into one of abundance and possibility.ā
Andres Pira went from sleeping on a beach in Thailand, using his suitcase for a pillow, to building a hospitality and real estate empire that made him a billionaire in his thirties. In this book, he shares the 18 principles of wealth-attraction, opportunity-creation, and self-discovery that helped make it all happen.
A massive part of it is knowing exactly what you want. Having a Definite Chief Aim. A single point of focus, toward which you devote your combined energies, relegating literally everything else to the status of being a lesser goal.
Another important consideration is making sure that your dream is big enough to inspire massive action. Outrageous ambitions energizes a person, helping you to persist and keep pushing past the point where most people, moving slowly towards ārealisticā goals, would give up and turn back.
Thatās not to say that everyone should aspire to become a billionaire. I can see myself being very happy, sitting on the beach reading a book!
There are as many good lives as there are people to live them, but the success principles stay the same, regardless of the size of your goals: You have to know what you want. You have to invest in yourself consistently. You have to bulldoze your fears and build your courage.
You have to gather around you a team of winners, all headed in the same direction. And you have to learn how to spot fantastic opportunities, and apply creativity, invention, and massive action in order to capitalize on them.
But if you do all that, and add in the other success principles laid out in this book, youāre likely going to find yourself inhabiting a compelling future you never could have imagined before you started.
āAnything below a Level 10 effort into your Level 10 problems means you are not as disciplined as you need to be. It doesnāt matter how many cold plunges you do at 5:00 a.m. while reading your book of the week.
If you arenāt putting a Level 10 effort into your Level 10 problems, it means you are procrastinating and avoiding what really matters. That is undisciplined.ā
This book changed the way I think about self-discipline. As in, it literally gave me a new definition of it, and itās one that virtually everyone could profitably adopt for themselves. That definition is simply that being disciplined is about putting Level 10 Effort toward solving your Level 10 problems in life.
The authors, Craig Ballantyne and Daniel Woodrum, take aim at cold-plunges and complicated morning rituals to get at the real truth about self-discipline and how to develop it. I mean, you could do everything else āright.ā
You could work out 7 days a week. You could drink 2 gallons of water a day. You could wake up at 4AM and read 2 books a week. But if youāre using all of that activity as a distraction from your Level 10 problem, then, by definition, you are undisciplined.
I thought that was such a fantastic reframe, and the whole book is full of extremely helpful advice about developing high personal standards, building the identity of a successful, disciplined person, and installing the systems that make it all work.
The Dark Side of Discipline isnāt any shorter or longer than it has to be, and itāll help you do what you should do, when you should do it, no matter how you feel about doing it. Which is the only āsecretā I can think of when it comes to achieving massive success.
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OK, thatās it for nowā¦
Iāve got plenty more excellent book recommendations coming your way soon though!
And if you want to learn how Iāve built an audience of 180,000+ followers across social media, became a full-time creator, and how Iām rapidly growing my audience and my profits in 2025, join us inside Creator Launch Academy and thatās exactly what Iāll teach you ā weād love to have you in the community!
With that said, I hope you enjoyed this edition of The Reading Life, and enjoy the rest of your day!
Until next timeā¦happy reading!
All the best,
Matt Karamazov
P.S. Whenever you're ready, here are two more ways I can help you:
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