10 Life, Money, and Business Lessons from James Altucher

Business Cat

Over the last few months, I've been burning through a lot of material by James Altucher, including two of his books, his Altucher Report newsletter, many of his special reports, and numerous episodes of his excellent podcast. The guy puts out an insane amount of content on a daily basis.

James is by and large a pretty likeable guy. He's really big on vulnerability; in fact, I first heard of him through a Ramit Sethi course where he used James as an example of being authentic. That can endear you to him quickly, as he talks openly and frequently about his failures.

The Two James Altuchers

What's weird to me is that there are two James Altuchers, not literally of course, but in his persona. Altucher has been around in the investment world for many years, both as a hedge fund manager and a writer. In fact, here's a screenshot from an email I had from Jim Cramer's old venture TheStreet.com dated 12/1/2007 featuring one of James' articles:

James screenshot

I actually didn't recognize his name when Ramit had first mentioned him in the course. When I later found out he had written for TheStreet.com (and, more importantly, was the creator of a stock picking web site The Street owned half of), I had to search through my email archives. Sure enough, there he was. (Don't ask me why I have stock picking emails from a decade ago.)

James still does investment stuff, but he's recently started a new company called Choose Yourself Financial, which sells his stock-picking and trading strategy newsletters. Honestly, heaven help you if you get on these email sales lists. I am all for James getting paid, but his marketing for these newsletters drives me nuts: bogus limited time offers, staged webinars, hard sell gimmicks, and incessant email marketing talking about once in a lifetime opportunities. I subscribed to The Altucher Report a few months ago, prior to when he switched it to be under CYF. It's a great newsletter, because it's 1) very cheap ($10/month) and 2) not fundamentally a stock-picking newsletter (though it does occasionally include these). It's more about investing in trends and starting businesses and more than pays for itself. It was when he shifted it to CYF that the marketing got annoying. For all I know, the rest of his newsletters (that range upwards of $3000 per year) are also full of good content, but his marketing for them is so spammy that I just can't handle it. Even as a paid subscriber to The Altucher Report, I get at least weekly emails trying to up-sell me. I'm not against sales, and I certainly am happy for James to profit off of his knowledge and experience, but the hard sell - especially to people who are already fans - really bugs me.

I really debated about including this last paragraph. I hate being negative at all, but especially about people I've never actually met in person who have done me way, way more good than anything else. Ultimately, though, I don't think James would have it any other way. He is, after all, the guy who says to always be honest in your writing. I just find Investment Newsletter Sales James to be so incredibly different than Author and Podcast Host James that I felt like I couldn't leave it out.

So, I stay away from Investment Newsletter Sales James. He seems desperate. Author and Podcast Host James - the James who talks about "choosing yourself" and investing in trends and self-publishing and his recent experiences trying stand-up comedy - seems to be the opposite. He's smart, funny, honest, and full of excellent ideas on how to be in control of your financial future. And now that I've got that rant off my chest, here are some of my biggest takeaways from that James, both from his "Big Ideas" and lessons I've learned from the way he runs his empire.

James' Big Ideas

Like most authors, though James has written a ton of articles, books, and special reports, they revolve around a handful of core big ideas. Here are the ones that most resonated with me.

  1. Don't depend on other people for your success or well-being: choose yourself. This is the crux of everything James does, and is the subject of his most well-known book, Choose Yourself. The book is an argument that we are living at the end of the time of employees and corporations, and the beginning of what he calls (of course) The Choose Yourself Era. My article "I've Stopped Caring About Finding My Purpose" was largely inspired by reading this book. Between automation, drones, and the ability for anyone to self-publish a book or a YouTube channel, corporations will have less and less incentive to hire traditional employees with traditional benefits. Where James differs from many folks in this space, though, is his encouragement to become an "entre-employee," rather than to quit your job immediately and start a business. Being an "entre-employee" means having the mindset of an entrepreneur at your day-job. In short, it's taking ownership instead of asking for permission. Company won't pay to train you? Train yourself. Boss won't give you more responsibility? Take more responsibility anyway. Do your job the absolute best you can. Make the most of the opportunities around you. If that leads to starting your own thing, great, but it doesn't have to. If your side gig becomes full time, great, but it doesn't have to. The bottom line of choosing yourself is not to rely on a boss, a partner, a spouse, a friend, or anyone else to determine your future - you get to choose.

  2. Build a foundation of physical and mental health every day (the Daily Practice) From what I gather, this is what made James famous outside of the investment world. You'll find a version or reference to the Daily Practice in nearly all of his books. Essentially, it boils down to taking care of yourself physically, emotionally, mentally, and spiritually every single day in small ways. That last phrase is the import part: "every single day in small ways." In fact, James has another article about getting 1% better every day at something that elaborates on this. Coincidentally, I had discovered a similar phenomenon just before I discovered James' Daily Practice. I had been journaling, practicing gratitude, fasting, and working out regularly for several months and had noticed huge results coming from these small daily steps. It was right in the middle of my PT work, which taught me the lesson that small, consistent actions are more important than big, sweeping changes. I had noticed that it was the consistency of journaling and working out that maintained my physical and emotional health. It was more work in a way, and the results came on gradually, but those daily habits became much more effective than one-shot efforts to make myself happy.

  3. Become an idea machine: Get good at coming up with ideas every day and give them away freely. This is the "mental" puzzle piece of the Daily Practice, and it was something I had never heard before. Altucher believes ideas are "the currency of life," and are the difference between success and failure on a day-to-day basis. Rather than relying on coming up with a good idea when you're in a crisis or state of panic (e.g. "how do I come up with my rent in two days?"), build that muscle ahead of time. To do this, write down 10 ideas every day for six months. Don't worry about if they are good or realistic ideas. Don't try to save them or hold onto them. Don't worry about executing on them. Just think of ideas. Give them away to people they may help. In fact, one example he gives is to email someone you admire with 10 ways they could make more money or improve their business. Do this expecting nothing in return; let the universe handle that. The goal is to shift your mindset, to train your idea muscle to be nimble and agile. My former housemate (who I now refer to as Rob on this blog) operates on a similar philosophy: he is amazing at coming up with business ideas and gives them away freely. He can do this because he knows two important things: 1) he can always come up with new ideas, and 2) having an idea is the easy part, executing it is the hard part.

  4. Have 7 income streams, not 1. This was actually the single most helpful idea I got from James, and it isn't even original to him (see this article from Rich Habits, for example). The concept of "choosing yourself" and the Daily Practice were both different spins on lessons I had learned through other sources, like Rob, Ramit Sethi, and my diet and exercise experiments. This one helped me get "unstuck" from feeling like I was trying to find one single Great Idea to make me successful. I'm not sure why it took the way James said it to click, but I guess it was just timing. Anyway, the point is to focus on building one new source of income at a time to slowly alleviate your dependence on your job. This holds true whether you're a traditional employee or a business owner or a freelancer, because you're essentially trying to diversify your risk. If some catastrophe happens that causes you to lose that income, whether you get fired or disabled or something else, you're not in a state of total disaster. These sources of income can take many forms, but what you're looking for here are opportunities for something called arbitrage, which is the ability to profit off an excess capacity of knowledge, time, skill, or goods. Know something others need ("knowledge arbitrage")? You could self-publish a book (another area James writes about often) or create a video course. Have some extra time or a skill others lack ("time and/or skill arbitrage")? Start a service-based business. I read one super-fascinating article by James Compton about starting a drone-based industrial inspection service. Can you get your hands on a product for cheaper than others can ("goods arbitrage")? Start a product-based business. Even something like reselling electronics you can get cheaply from Alibaba is a decent idea. Which one you choose is up to you and your interests, and the payoff will be different for each one. You also don't need to get scared off by the term "business" - think of it more like a "side hustle" or something you do in your spare time to make some extra money. If it turns into a full-fledged business, cool. Personally, I love teaching and explaining difficult concepts, so I've been drawn to the idea of front-loading the work into things like books and courses, which then can become a stream of income over time. There are many ways to slice this pie (mmm, pie), but the point is to get started, building one new source at a time.

  5. Make money off trends.. Once you've developed all those ideas, you can start paying attention to macro trends in society and making money off of them. Examples of trends include things like self-driving cars, automation, energy storage and batteries, marijuana legalization, the shift away from oil, and cryptocurrencies. There are tons of them, and we're looking for large scale shifts that will happen over decades. You can profit from these trends in numerous ways: you can start a business around them, you can invest in related businesses through ownership, you can invest in stock in companies directly involved in these trends, or you can invest in stock in companies tangentially involved. Take marijuana legalization, for example, which is destined to become a multi-billion-dollar industry over the next decade or two. You could start a farm, sure, but you could also invest in companies that make equipment, or make fertilizer additives, or make parts for consumption devices (like the heating element in vaporizers). You could start a business setting up hydroponic or aeroponic systems. You could invest in companies working in medical research like GW Pharmaceuticals (Nasdaq: GWPH), which is working on a drug called Sativex to help MS patients with muscle spasms. There are lots of ways to do this, and you could apply the same rubric to another trend like batteries of self-driving cars. You're looking to do this with little risk, so no "get rich quick" schemes and no "sure fire" investments. You want ways to profit that you at least fully understand, but ideally are directly involved with. You can use these as trends as arrows in your income quiver, and diversify so that you're not dependent on any one trend at a time. That way, if something goes differently than you predicted, you're not losing everything. These trends are also so macro and so slow, though, that should have plenty of time to course-correct if things change.

We're halfway done, so here's a GIF of a baby goat falling down a slide.

Meta Lessons

Part of the reason I delve so deeply into artists, authors, speakers, and entrepreneurs is to understand how they run their business and what has made them successful (spoilers: the common theme is usually a lot of hard work you don't see). I try to glean what wisdom I can from their Big Ideas, but also their own journey. Here's what I've learned from James Altucher's writing and podcasting career.

  1. Produce and promote content frequently and consistently. James makes a new podcast and a new article every few days, and promotes them through his email list, his Twitter, and his Facebook page. The regularity and sheer volume of this content is awe-inspiring. Granted, he does this full time, but he also has lots of other projects going on, so the fact that he makes time to build an ever-growing empire of free content is both admirable and bewildering. He's pretty practiced at this point, and has his message and voice down, but my lesson here is that consistency is more important than quality. Of course, you should do the best you can with whatever you're writing, but don't sacrifice consistency for the sake of publishing something perfect. In fact, the best way to get better at anything is just to do it more often, and writing and podcasting are not exceptions to that. The more frequently you can publish, the more frequently you can get feedback and incorporate that into your work going forward.

  2. Establish a core set of your ideas and generate content from different angles around them. I've seen this from Ramit, too, and many other authors and speakers. James has a few big ideas, as you've read above, but he has managed to produce a mountain of content around them. You can write books and articles around the "why" or philosophy of these core ideas, such as why it matters to be self-published. You can write content around the "how," like step-by-step guides. You can interview people who share that philosophy or vehemently disagree with you (the latter will probably be more interesting). You can write up breakdowns of how people do or do not adhere to these core ideas (again, the latter is often more interesting). To be honest, I'm still hammering out my core ideas, but that's what this blog is for.

  3. All advice is autobiography. James does a really good job of using "I" all the time and talking about what works for him. In his interview with Kamal Ravikant about Ravikant's transformative trip to Spain, the two of them talk about how nearly all self-help literature is about YOU, it's never about I. It's always a list of things YOU need to do, about how YOU need to be better. The truth is, that never works. No one wants to hear about ways they aren't living up to expectations. Nobody wants to be preached at. They want to hear what works for you, and then decide for themselves whether to try it or leave it alone. I've really taken this to heart lately, and am avoiding writing articles about how you should lose weight or how you should start a business. I'm just here to document my own journey, meandering and flawed and strange as it is. If this stuff helps someone else (and I hope it does), fantastic.

  4. Turn podcast interviews into conversations. I've thought about starting a podcast over and over again, and I think I am finally going to do it, inspired by James' podcast. What makes his podcast so awesome is that he manages to disarm people and get them to open up in ways they don't on other platforms, whether because the host is too overbearing or because the guest is too busy trying to self-promote. James' interviews are more like conversations, often with his actual friends, like the interviews with Derek Sivers and Ramit Sethi. Even with strangers, though, he is able to elicit a level of honesty you don't often get to see. I've noticed he achieves this using a few techniques. First, he is always incredibly well-prepared. At this point, I'm sure he has an intern or employee do the research for him, but regardless, he is well-versed in his guest's personal and professional history. He tries to go for the "deep cuts" of their career, not just the stuff in top Google result for them. This impresses them, which lowers their shields a bit. Second, his tone is spontaneous and conversational. I've read that he doesn't send interview questions ahead of time. Of course, this must be somewhat easier with the folks he has known for years, but as anyone who has ever performed knows, everything seems to change once you're in front of a microphone. He's extremely well-practiced and comfortable, which also puts his guests at ease. Finally, he doesn't start off asking guests about their Latest Thing. He asks them for advice, or for perspective on something he's thinking about right now, or about a funny story from their childhood. This disrupts their expected pattern of saying, "Well my book is called Why I Am Amazing and it comes out next week." Pattern disruption elicits honesty, because we're not regurgitating something practiced. Try it on a date or at a party sometime instead of asking the usual "what do you do" question. All of these things combined make the magic that sounds like we're sitting around a dinner table. I've learned a ton about interviewing from listening to these podcasts and am antsy to give it a shot.

  5. Self-publishing a book is a great way to market yourself. I debated about whether to include self-publishing in the "big ideas" section, but I feel like this is more meta than that. While James does publish a lot of articles and reports on how to self-publish a book, he also is an example of how to do it well. He mostly uses his books as a way to market himself and spread his ideas, not as a way to make money. This is through a combination of giving his books away in conjunction with his subscriptions, offering them for dirt cheap on Amazon, and doing publicity stunts with them (he was one of the first people to sell a book for Bitcoin, for example). When I signed up for The Altucher Report to check it out, I was given electronic editions of all of his books and reports, the audio edition of The Choose Yourself Guide to Wealth, and a drop-shipped hard copy of the same. James has coined a phrase, "Books are the new business card" and it certainly holds true for him (side note: I can't wait for the business card scene in American Psycho to be redone with books). He's also able to crank books out pretty rapidly, because they are often a repackaging or expansion of topics he's covered in his blog or on the podcast. Some of that can get annoying, like including a transcript of a podcast as 20 pages in a book, but it seems like he does less of that particular trick these days in his actual books (he still does it in "special reports," but those are also largely free). He also does not always edit very carefully, as many of his reports and books are transcriptions of audio and can contain typos. I don't point this out to be a jerk, but to illustrate that perfection isn't always necessary to accomplish goals. "Good enough" often is just that, especially when you're cranking out so much content that the ideas are worth way more than whether you've misspelled a word.

Bonus: My Top 4 Episodes of The James Altucher Show

We've come to the end of the lessons, but I want to leave you with one more thing. James' podcast is at 265 episodes and counting, and, despite my glowing praise, it's not like every episode is made of gold. Some people don't play James' game and just insist on self-promoting and not opening up. And, more to the point, you're not going to consume hundreds of hours of podcasts. So, here are my top 4 favorite episodes for you to get started:

  1. Gary Gulman Breaks Down the Best Joke in the World. I had never even heard of Gary Gulman before this episode, and he is amazing. The joke referred to in the title is this one from his performance on Conan in July 2016. It's 6 minutes and 19 seconds of pure comedy gold, and I won't spoil it for you. The interview is an enthralling breakdown of how Gary carefully crafted literally every second of this joke. It also includes Gary very candidly discussing his own struggles with depression and anxiety in that level of honesty only James can seem to elicit.
  2. Nancy Cartwright – Surprise Yourself and You Will Surprise Everyone Else. Super fascinating, and not about The Simpsons. This is one of Nancy's favorite interviews ever, because James did a ton of research on her life, her career, and her recent limited release film, In Search of Fellini. You can tell she's opening up in a way she never gets to do, as I'd imagine most interview hosts just want her to say the name of their show in the voice of Bart Simpson. (Like Andy on Extras being reduced to "Are you having a laugh?")
  3. Jim Norton – Dropout and Laugh. I basically love all of the episodes about stand-up comedy. This one intrigued me because James has known Jim Norton since the 4th grade, so there are lots of hilarious anecdotes about how this guy has grown up and learned to embrace who he is. It's also an interesting look into the business side of stand-up, from touring to books to movies to TV (Jim has done it all).
  4. Gary Vaynerchuk - Set a Flag on YOUR Thing. Okay, I'm biased on this one. I've been a fan of Gary for a decade, back when he was making WineLibrary TV. He's still awesome, and this is mostly a conversation surrounding the topics Gary covered in his video "How to Start", about producing and promoting content. People see Gary's meteoric success and immediately misjudge him, but let me tell you, he's the real deal. I met him back in 2009 at a conference and was blown away by his humility in person. He recognized me across the room from Twitter and following WineLibrary TV, thanked me, and offered to give me whatever advice he could offer. This conversation with James just reinforces everything I've loved about him for the last decade.

So that's what I've got for you on James Altucher. He's been a big help to me lately, so give him a look and let me know what you think.