Entrepreneur, investor and writer; author of Choose Yourself and host of The James Altucher Show.
Sam claims his friend James Altucher sold his crypto newsletter for $60 million, illustrating how lucrative paid crypto newsletters became.
“He's a friend of mine, dude. He sold his news— his crypto newsletter for $60 million.”
Sam uses James Altucher as the cost-of-the-game example: he was ridiculed for pushing a Bitcoin newsletter, made $60 million doing it, yet got mocked constantly. The lesson: most people would rather skip the money than risk being made fun of.
“So guys like James Altucher, who we've had this podcast, he was ridiculed for doing this with Bitcoin. Everyone made fun of him. He made $60 million doing it, but he still got mocked constantly. And shockingly, most people would actually prefer not to make the money and not get made fun of than they would to make the money and get made fun of.”
James Altucher describes how, after years writing about finance, he started publishing raw personal stories about failure and depression. People thought he was suicidal or had cancer, but his audience grew 100x and unlocked far more opportunities.
“My audience became 100 times bigger, and then I started getting more investment opportunities. I started getting a podcast, which became successful. I just started getting many more opportunities because of, because essentially I paid with my vulnerability for freedom, and that created a whole kind of career for me.”
Steal thisWrite the thing you're scared to publish; vulnerability is the moat competitors won't copy.
American Express paid Arthur Andersen millions for a website, who subcontracted to a software firm, who hired Altucher because nobody knew how to build websites in 1995. He and his brother-in-law collected $250K to build americanexpress.com while his HBO salary was $40K/year.
“And then suddenly they'd pay me and my brother-in-law, uh, $250,000 to make americanexpress.com. So That was one of our first websites. And I, my salary at HBO at the time was $40,000 a year.”
Altucher built websites for HBO, American Express, The Matrix and record labels, then sold the agency near the dot-com peak in 1999 and took the proceeds entirely in cash rather than paper that later went to zero.
“Uh, about, uh, $15 million. And then cash. Holy fuck. Yeah. So cash, not, not like, so a lot of people then, you know, went public or sold and they got paper and then they died in the dot-com bust because the paper went to zero, the stocks went to zero. So I had enough sense at like the peak in 1999, I cashed out and I had the cash in my checking account.”
After cashing out of web design at the peak, Altucher poured all the cash back into internet investments because people kept asking the 'curly-haired glasses tech guy' for advice and he started believing he was brilliant at everything.
“And then I became everybody, you You suddenly, when you make money at one thing, suddenly you think you're a genius at everything, or at least this happened to me. And everybody would come to me and say, "Hey, what should we invest in?"”
Steal thisAfter one big win, deliberately stay inside your circle of competence instead of assuming the skill transfers.
After pouring his $15M back into internet investments with no understanding of risk, Altucher was losing about $1M a week by summer 2000 and hit zero by mid-2001. He had his apartment near the World Trade Center up for sale and a buyer pending on September 11th, when it became a crime scene.
“Um, I was losing about $1 million a week in the summer of 2000, and And I just didn't know what I was doing. And it wasn't even that I didn't know how to invest. I didn't know there's so many other skills to investing than knowing what companies are good and what companies are bad. Like, I didn't understand risk. I didn't understand money management.”
Altucher was an early investor in Buddy Media alongside Peter Thiel, with Mark Pincus also in the seed round at a $4M valuation. Salesforce later acquired it for roughly $700-800M.
“we all were the seed investors at a $4 million valuation that sold to Salesforce for about $700 or $800 million.”
Altucher's most successful investing rule is to only put money into deals where someone far smarter (like Peter Thiel in Buddy Media) is investing on the same terms, outsourcing all due diligence to them. The corollary: if a founder ever calls him for advice, he marks the investment as zero.
“than me says, hey, I'm investing in this company, I don't even have to do any more work. I just send the check. 'Cause I assume, and I'm always correct when I assume this, he's done or she's done all the due diligence. All the hard work.”
Steal thisCo-invest only when a far-smarter lead is in on the same terms; treat an advice request from the founder as a sell signal.
Altucher argues starting, building, and selling are three different skills. A sale is a courtship that gives way to a painful due-diligence waiting period, and you must master deal structure and negotiation since 9 of 10 people wrongly think they're above-average negotiators.
“And you have to be, you have to have some skills at negotiation, which negotiating is one of those things that 9 out of 10 people think that they're above average, which is impossible. Like you have to be 4 out of 10 only could be above the median and only 1 out of 10 is really good enough to sell a company properly.”
Altucher lays out the three valuation methods: an industry earnings multiple cut in half because no one pays full price, a forward model based on monetizing your traffic/audience (also halved), and comparable acquisitions in the space.
“So that also is a really great question because there's, there's 3 ways to value a company, right? The one is a, a standard industry multiple on your earnings and cut it in half, by the way, because no one's gonna pay the maximum. You cut it in half so they, everybody wants to get a deal. So like if, if you have a profitable company and it's in an industry that trades on the stock market for 20 times earnings, then your company is probably your last year's profits times 10, the 20 divided by 2.”
Steal thisWhen pricing your company, take the public-market earnings multiple and cut it in half as your realistic ask.
Altucher's recovery practice after each crash was to write down 10 ideas every single day, on waiter's pads or email, treating it as exercise for a muscle rather than a hunt for good ideas. He says it rewired his brain within months and generated a constant flow of opportunities.
“And creatively, I, I just started writing down every single day, 10 ideas a day. Like, uh, and it could, it could be business ideas, it could be writing ideas, it could be dumb ideas, it could be ideas for TV shows, it could be ideas for how Google could be a better search engine, and then I would arrogantly send them to Google. But the whole idea was not to have good ideas, but to just practice this creativity muscle or else it would atrophy.”
Steal thisWrite 10 ideas a day, intentionally bad ones, to train the idea muscle rather than to find winners.
Altucher's framework for staying high-functioning is to attend daily to four pillars: physical (eat, move, sleep), emotional (cut toxic people), creative (10 ideas a day), and spiritual (stop trying to control what you can't). He says it sustains wellbeing through both money gains and losses.
“And that really just those 4 things, physical, emotional, creative, spiritual, just those 4 things. If I attend to them every day, I, I keep at a very high state.”
Steal thisAudit yourself daily against four pillars: physical, emotional, creative, and spiritual health.
Altucher's core risk rule is that he never invests more than 1-2% of net worth in any single company, but lets winners run far past that. He invokes the Buffett line about not trading Michael Jordan just because he improved, preferring private companies that keep compounding 50-200% a year.
“So I never invest more than 1 to 2% of my net worth is the maximum I will ever invest in any company. Right now, I'll let the, I'll let the investment grow to much more than that. It's sort of like what Warren Buffett says. If you've got Michael Jordan on your team, you don't trade him just because he got better.”
Steal thisCap any single angel bet at 1-2% of net worth, then let the winners run uncapped.
Altucher is actively building a way for ordinary creators to monetize content. Today only the top 0.1% (like Logan Paul) can monetize YouTube, and someone with 300 followers can't monetize a tweet 20M people see, even though the platforms have the ecosystem to enable it.
“So you have to be like, you know, Logan Paul to monetize your YouTube channel and the other 20 billion people on YouTube, even if they have one video that goes viral, they can't monetize it. So, or, or like even if you have a, if you have a tweet that 20 million people see, but you have only 300 followers, you can't monetize it. So I've been figuring out a way to use these ecosystems to allow people to monetize content.”
Steal thisBuild the rails that let a creator monetize a single viral post even without a large following.
Altucher's idea-generation method combines concepts from two unrelated industries ('idea sex'). His current target is monetizing the bottom third of a sector the way Square let mom-and-pop stores accept credit cards, turning it into a roughly $12B company.
“Square is a great example. Square took the mom-and-pop store that couldn't accept credit cards because no bank would trust them, and Square enabled them to accept credit cards. So Square's the only company in the world that does that, and they became, I don't know, a $12 billion company because they were able to monetize the bottom third of, you know, mom-and-pop retail stores.”
Steal thisTo build a billion-dollar company, find the underserved bottom third of an industry and let them collect money.
Altucher's playbook for building an audience from zero: answer every question on Quora, LinkedIn and Facebook groups to establish expertise, then graduate to higher-barrier outlets like Forbes and TechCrunch for authority, then launch a free newsletter, and only later a paid subscription.
“I would go on Quora and just answer every question I could. I would participate on LinkedIn groups, again, answering every question I could. I would go on groups like the Trends Group or other Facebook groups, and you know, a lot of people ask questions.”
Steal thisStart by answering every question in public forums to build expertise, then climb to authority outlets before monetizing.
Altucher cites a shy, introverted friend who built an online course teaching people how to become a media expert, priced at $700, opened for just three days a year, selling around 1,000 seats for roughly $700K annually while living in a cheap country.
“she started a course on how to be noticed by the media, how to become a media expert. And she priced it at $700. She sells, she opens it up for like 3 days every year, sells another 1,000 and makes $700,000 a year.”
Steal thisOpen a high-ticket course for only a few days a year to create urgency and a clean annual revenue number.
Matt Berry was a miserable Hollywood screenwriter who quit, went broke, and started blogging about fantasy sports for $100 a post. His writing skill built a huge audience, he launched a paid subscription site, ESPN bought it, and he ended up far happier and richer.
“That guy was a Hollywood screenwriter. He was writing movies and TV shows and he hated his life and he quit that. He's making a ton of money. He quit that. Started writing blog. He just loves sports and fantasy sports. He started blogging about that for $100 a blog post.”