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Is Ryan Holiday the Real Deal?

Multiple New York Times bestselling author, Ryan Holiday, is hard to miss. He brought Stoicism front and center with his books, Daily Stoic and Daily Dad emails. But is Ryan Holiday the real deal? Does he walk the talk? Does he live what he preaches? Does he practice the principles he teaches when interacting with the public? In private? And for some strange reason, people want to know Ryan Holiday’s net worth.

Over a 4-month period this summer I visited Holiday’s bookstore in Bastrop, Texas twice. The first visit was partially unannounced and all I got was a sighting. Then in November I attended a social gathering put on by Holiday. (I bought a lot of his books for the invite.) This post is on that gathering.

My approach to seeking an audience with a celebrity is a bit different than most. Some want to get close so they can look important. Some people want something from the celebrity (business deal). Me? My concern is with the “real” person behind the mask. I want to learn from someone that has done incredible things and apply it to my life.

Over the past several decades I have met numerous “celebrities” and politicians. Most are authors because authors are thinkers and impress me most. JL Collins1 and Mike Resnick2 , for example, are two authors I admire and have met. JL Collins I consider a friend since I have visited him at his home more than once (he invited me).

If you want to meet public figures, attending conferences is a good way to find yourself in a one-on-one conversation with an author or other celebrity you admire. If you keep your eyes open there will be opportunities for a “real” conversation with someone you admire.

Many public figures I met ended up as consulting clients so confidentiality prevents the ego-stroke of name-dropping.

Ryan Holiday undercover.

Behind the Mask

Approaching a public figure requires finesse. These people frequently need to build walls to keep people out for their own protection and sanity.

Often, you will see celebrities in the limelight surrounded by reporters and other people wanting to “take a moment of their time”. Being part of that crowd is a bad way to know another human being and leaves no impression or a bad one.

A client (a public relations consultant) once explained to me the way to approach public figures. He said the best way to know a public figure is to stand back when everyone else is pushing in on the victim target individual.

Somewhere in the back of that crowd, he continued, is his support team: public relations officer, editor, publisher, friends, family, security. These people work close with the public figure on a regular basis and stand ready if someone gets out of line.

By standing back, he said, you stand a good chance to have a conversation with one of these support team members, which, incidentally, have nobody pushing to speak with them. A conversation with “the team” is the best way to get to know the “real” celebrity. They know more about the public figure than the public figure will ever tell you.

If the support team likes you they sometimes invite you to a private meeting or dinner with the public figure. Now you can have a meaningful conversation without a crowd screaming for the celebrity’s attention.

This is the approach I used when attending the gathering at the Painted Porch Bookshop with Ryan Holiday.

When Holiday arrived he made the rounds of our small group. There were maybe a dozen people at the gathering outside Holiday, his wife and team members (at least 5). That was my first personal introduction to Ryan. We shook hands and exchanged pleasantries.

Then I did what I do best. I stood next to, and struck up a conversation with, Ryan’s team members. It was a pleasant evening of conversations and it didn’t take long for the discussion to turn to finance. Everyone wants enough for financial independence so they can cut their own path. I have at least two email addresses to stay in touch with “the team”.

And I learned more than you can imagine.

Painted Porch Bookshop: The world’s best small bookstore.

Ryan Holiday in the Wild

The one thing you will discover is that most celebrities are very normal people when the spotlights turn off. Even people with a reputation for wild public behavior are very intelligent and decent in “real” life.

Ryan Holiday fits this description. He was engaged with the people at the gathering with some people sitting next to and across from him at the dinner table. (I sat near the end of the table with people that worked with Ryan.)

As is normal, Ryan has plenty of walls to keep an efficient work environment. Every public figure needs separation from distractions to get important work done. Writers need more quiet space than most.

Try to contact Ryan Holiday and you will find it hard to get through. If you want to meet people like Ryan, and those like him, you either have to attend a conference he is at or pay the price for a more intimate gathering as I did in this instance.

Now let’s discuss some personal details about Ryan.

I did get a chance for two longer conversations with him. The first thing I noticed is his commitment to family. He inquired into my work and family life and he shared some details on his family.

He was also low-key. He drank water (he refrains from alcohol). He focused on the person he was speaking with. Always professional in his manner and interactions.

As expected when conversing with an author, he is very intelligent, yet never once did I see Rytan talk down to anyone. He lives life with purpose, and from what I saw, is non-judgemental.

Any conversation with Ryan will involve Stoic principles. It’s not forced. However, as the philosophy would apply, he mentions it. He walks the talk, gentle readers.

Ryan also shared some dreams. He is building out a podcast studio next to the Painted Porch Bookshop. You could see the passion in his eyes as he looked forward to growing that part of his business.

I think it is fair to say that when you see Ryan on YouTube and Facebook videos, in this Daily Stoic and other “Daily” emails, in his books and in real life, he is exactly what you see in his personal life.

He is very driven and focused. If you saw Ryan without context you would not expect the business dynamo he is. He speaks from the heart. I got the feeling every step is choreographed.

The last thing I want to cover before spilling interesting personal tidbits I learned about Ryan is his net worth.

For some reason people want to know the net worth of a public figure. The numbers batted around online are almost always a world away from reality. I probably am only marginally closer.

Autographed copies of Ryan Holiday’s latest book: Discipline is Destiny.

Ryan Holiday’s Net Worth

Since no one, except Ryan himself, can know for certain what his net worth is, this will become an accounting exercise. Don’t worry. It will be short and fun.

Ryan never discussed any financial matters with me. My entire estimate will be based upon information Ryan has published himself.

We know Ryan owns a farm. I took zero time to “find” his farm or what it is worth.

We know he owns property in Bastrop, Texas. You can check the tax rolls for an estimated value on your own.

What determines net worth is your savings rate and time. If you earn $100,000 per year and invest half of it every year, I know you invested $500,000 over 10 years. Tucked into a broad-based index fund will have grown your nest egg to just north of $925,000, assuming a 10% rate of return. (Future Value Calculators make this math easy.)

Ryan has shared some of his sales numbers from early in his career in videos. Book sales for recent books are available online (as estimates, I assume). (You can look the details up on your own because this is a discussion on how to estimate someone’s net worth. Since it is not an exact science I will not provide an actual number.)

Writers get paid in a variety of ways. They usually get an advance. The advance covers a wide range. Novelists may get nothing or a few thousand dollars as an advance. Non-fiction almost always has a larger advance.

However, the advance is kind of meaningless in calculating net worth because when the book is published, royalties are charged against the advance before additional payments are made to the writer. The number of books that don’t earn out their advance is significant, meaning, the author may never see another penny of income from that book.

Ryan Holiday is a master at promoting his work so I will assume he earns out his advance and move to a second way income is estimated for an author.

It has been a long time since I discussed contracts with an author so things might be a bit different from what I am familiar with. From my experience, an author is paid 10% to 15% of the cover price of each book sold. There are often exceptions if books are sold as remainders or heavily discounted. Often times there is also a scale. Example: Up to 10,000 books: 10%; 10,000 – 25,000 books: 12½%; over 25,000, royalty at 15%. (Do not consider my example as typical because I have no idea if it is.)

At 15% for a book with a $25 cover price equals $3.75. Foreign sales, ebooks, and audiobooks all have a formula for royalty payments as well. The contract can be quite extensive. Terms vary.

Next we have the bookstore. Books generally wholesale to the retailer at a 55% discount, if things haven’t changed (it might be 55% discount to the wholesaler and 40% to the retailer). This also might be different, depending on the publisher or wholesaler. Ingram was a leading name when I worked with authors in my tax practice. They are still a good resource.

At a 55% discount, the store pays $11.75; at 40% discount the bookstore pays $15 for the book. The author still gets the royalty if he sells the book through his bookstore.

Now subtract estimated overhead and operating costs and you have net income. Estimate Ryan’s savings rate and where he invests and you have an “estimate” of his net worth. The key word is “estimate”!

Speaking with Ryan’s team allowed me knowledge of how many books Ryan sold from his bookstore out of the gate for Discipline is Destiny. Quick accountant that I am (backwoods accountant and all, excepted), and I can figure out a range for Ryan’s gross profit (that week).

That is where this conversation on net worth ends. Any sales numbers shared with me I consider confidential. (However, if you threaten to pull off my fingernails I might break when I see the pliers coming. In my defense, I will hold out as long as I can. I “estimate” you will be on the third fingernail before I break.)

Ryan Holiday loves animals.

Ryan Holiday’s Personal Life

Ryan is fond of animals. Some time ago a picture was posted on social media of Ryan sitting in the passenger seat of a vehicle with a llama staring him straight in the eye. Ryan was grinning ear-to-ear.

People that love animals are almost always good people, especially when they practice good animal husbandry. Ryan has a variety of of animals on his farm and treats his animals with care. That qualifies Ryan as a “good guy” in my book right out of the gate.

He did disclose that they were considering getting a llama, but that had to bring the animal collection to a stop. I fully understand having too many animals.

Ryan is a dedicated businessman. He has a plan, promotes constantly, keeps a schedule and monitors his sales. He has goals. At least for the bookstore. And I can’t imagine that not spilling into other areas of his professional life.

This is markedly different from another author worth reading: Simon Sinek. Simon is an entertaining and informative speaker, too.

In this video, Sinek discusses how he handles book sales: he never looks. He just wants to spread his message and sales are not what he wants to focus on.

The accountant in me has a cross look when hearing this. From my perspective, I think Ryan Holiday is also very goal oriented and DOES look at his numbers.

I point out the dichotomy between Holiday and Sinek as a way to show both ends of a wide spectrum. It is easy to get caught up in sales figures and page views. Checking “your numbers” also takes away from creative time and marketing. It is more art than science figuring out the right mix for maximum productivity and motivation.

Ryan is a serious guy. He smiles, of course, and enjoys humor. However, you see the wheels are always turning as he listens to you. He is thinking about the steps necessary to make this person’s life better.

Ideas pour out from Ryan. He really is dedicated to living his life at the highest level possible by paying-it-forward.

At the gathering Ryan made a point to visit every guest several times. He thanked each guest for buying his book, inquired into who the guest is personally and shared ideas on living as it applied to the conversation.

Ryan is not a one act show. He is far more than just Stoicism and is clear his interests lie with the Stoics and not stoicism. (Notice the difference in upper and lower case. Capital “S” in Stoic refers to the philosophy and the original practitioners. Lower case “s” refers to the modern idea of being a stoic as having a stiff upper lip and not expressing emotions. There is a difference.)

It seems anyone Ryan Holiday touches becomes successful. Robert Greene, Tim Ferriss, Tony Robbins and Neil Strauss are individual successes he personally worked with. He also worked in marketing at American Apparel at a time when textiles were not produced in the U.S. profitably. American Apparel was a very successful company to the time he left.

The secret to Ryan’s success is work ethic. He does not waste time on non-productive activities. He lives with purpose. That is what drives his success and what attracts people like you and me, gentle reader, to consume his products.

Ryan Holiday’s secret to a better life.

How to Approach a Celebrity

I will conclude this post with advice on how to approach public figures.

If you are reading this because you want celebrity clients, I published on that here.

What I want to address are the horror stories from the celebrity’s viewpoint. Ryan will stand front and center in some of these stories.

First, ALL celebrities build walls/ have gatekeepers. This should come as no surprise. Even a small business owner needs to build a framework where they can perform their duties and keep their sanity.

When I speak of celebrities/public figures I am referring to people with a modest to large following. Because of their fan base there is a constant demand by fans to take “a bit of your time”. Allowed free reign, the celebrity would have no life and creativity would grind to a halt. In other words, neglecting a framework to prevent easy access to them is a recipe for failure.

Respect the gatekeeper. It is their job to turn you away. The celebrity cannot! speak with everyone that desires an audience. Respect the celebrity. Use some of the ideas I discussed above for meeting people you admire. If all works well, you will enjoy some quality time with your role model.

There is something you CAN do for people you admire. Send them a handwritten thank you note. Every celebrity I worked with keeps these tokens from their fans. It means a lot to them.

A small gift is also acceptable. A drawing or small item that incorporates the celebrities work and/or interests is welcome (as long as it isn’t creepy).

What not to do #1.) Ryan, and many other authors, use research assistants. Do not travel from another continent to the celebrity’s home asking for a job as a research assistant, using your skills to hunt down the private address of the celebrity as proof of your talent.

Some variation of this happened to Ryan as far as I could gather. Understand, if you did that to this country accountant, I would need to go to jail from such an encounter; you would go to the hospital. I might be a nice guy, but I can also be an ass and this situation would be one of those times.

Instead, send or drop off a resume with cover letter. Since Ryan has a bookstore, a resume dropped off with a bookstore worker, coupled with a few kind words, is the best you can do without getting creepy. There is no guarantee Ryan will even see the resume. My point is this: Don’t do something that will cause the celebrity to remember you for the wrong reasons. Then you get blacklisted and all hopes of working for the celebrity are lost.

What not to do #2.) It blows my mind I even have to say this one. DON’T trespass on the celebrity’s property.

You see this in the news periodically. Those are the cases you hear about.

It seems people cross the barrier now and again in Ryan’s world, too. Yes, he has a bookstore. (A nice one, I might add.) There are parts of the building used as his offices for creative work and marketing. YOU ARE NOT ALLOWED IN THOSE AREAS WITHOUT INVITATION!

If you want someone you admire to not like you, this is a really good way to do it. Don’t cross the line. Literally.

What not to do #3.) Don’t stalk the celebrity. Loitering around their property, even their business building is bad form.

By all means, if it is public property or open to the public, take a look around. We are all curious. Just don’t be that guy, the creepy one that leaves the wrong impression.

What not to do #4.) One last “do not”. This one I get from my doctor clients and is not specific to Ryan, but would not be surprised if he has similar stories.

Doctors (and celebrities) have busy and stressful lives. They take vacations with family. Tracking them down to where they are staying while on vacation to ask a “quick question” or demand service is a sure way to get fired as a client.

Celebrities can’t get away from this in many cases. A few of my consulting clients over the years were well known names. They were unable to get away no matter where they went. People found them. In those cases I brought the celebrity to me and provided an undisclosed location for us to work, discuss life and relax.

All these “do nots” boil down to respect. Respect the celebrity/public figure. They have a massive number of people pulling at their sleeves. There is a better way to treat a celebrity. My first trip to see Ryan ended with only a sighting. It could have been more, but I don’t roll that way. You can read about that here.

You can find Ryan’s videos on YouTube here.

1 JL (Jim) Collins moved from New hampshire to an hour and ten minute drive south of my home. He may have written the best personal finance book on investing ever: The Simple Path to Wealth. His book is considered a classic in the FIRE community. He has a new book coming out, yet unscheduled, from Harriman House. You can also read more from Jim at his blog: JL Collins NH.

2 Mike Resnick may have been the most decorated science fiction authors of all time, yet he only had one best selling novel. His short stories were always must-read material. From Mike I learned the true nature of pay-it-forward. He had such a big heart. He shared with me before his passing in early 2020 that all his award winning and nominated short stories were written in first person and all his novels that sold well, in third person. I don’t know how important that is to you, but it always stuck with me. You can purchase Mike’s books here.


Friday 6th of January 2023

Holiday is clearly a marketing genius. Otherwise, I'm not sure who would buy his books. I've tried multiple times and can't find an original thought. But yes, there is quite a bit of petty sanctimony. YMMV.


Sunday 25th of December 2022

What a great story, I had just discovered Ryan about two weeks ago when I ran across his Youtube video with Jack Carr, the Navy Seal. From there, I entered the rabbit hole that is Ryan Holiday, and consumed a bunch more of his teachings, and it's left an indelible impression on me. Thanks for sharing this!!

Sam @ Financial Samurai

Friday 9th of December 2022

Cool, tell him I said hello next time you see him. We have the same publisher, Portfolio Penguin.

I really enjoy reading this inside from a fan about a celebrity author. It makes me think about how hard on hers need to work to make a big. It also makes me think about whether I want to be famous or not. And the answer is no.

Even with just my Wall Street Journal best selling book, Buy This, Not That, I get so many requests every day for help. I want to help everybody and I always respond, but my freedom gets shrunken away as a result.

I would give writing a book ago yourself. It’s an eye-opening process!


Keith Taxguy, EA

Friday 9th of December 2022


I follow your work as well, Sam, and understand your aversion to fame. Ryan also talks about this, "Most successful people you have never heard of and they prefer it that way." Too bad we need to be noticed in public professions. Still, keep the faith. Focus on your work and the value it provides. It brings sanity to a productive life.

Keep in mind I don't chum with Ryan. I will pass the greeting along if I get to see him again.

Note: I added a link to your book. Hope you don't mind.


Thursday 8th of December 2022

I’ve read and enjoyed most of his books but was kinda turned off during the whole COVID thing. He basically came out and said anyone who doesn’t agree with the accepted narrative (and him) is an idiot. Of course he used nice words but I would’ve expected more of an open mind and trying to understand different viewpoints from someone as intelligent as he appears to be.


Thursday 8th of December 2022

@Jay, i was tempted to post a similar comment. I unsubscribed from his email during COVID. Just felt like he stopped practicing what he preached about Stoicism.


Thursday 8th of December 2022

@Jay, yeah don’t think he ever apologized to trump for doubting his sanity when trump was saying covid came from a lab. Now everyone pretty much accepts that as the most likely scenario.