There’s only one winner in the deal between the podcaster and the music streaming giant. And it’s not Rogan.

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Photo: Vivian Zink/Syfy/NBCUniversal via Getty Images

Oil companies are famous for approaching hapless farmers and buying drilling rights for their properties for next to nothing.

The farmers don’t realize they are sitting on tens of millions of dollars of oil, so they accept a $50,000 one-time payment.

It feels like a huge win…

Until they realize that they just lost out on tens of millions of dollars of oil riches.

That’s Joe Rogan right now.

In September, I wrote a post about how Howard Stern is getting ripped off by Sirius. I made the case that Howard Stern is making $90 million a year when he could be making 2–3x by cutting out the middle-man and doing a subscription podcast. …

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When I met Brian McCullough, I felt like we already knew each other.

We didn’t. But I had spent hundreds of hours listening to his voice during my most intimate moments. Rocking babies to sleep. Sitting in the sauna. Walking my dog. He had been in my head (or at least my ears) for hours each week.

That’s because Brian hosts an incredible daily podcast called The TechMeme Ride Home. I have been a habitual listener for over a year, and Brian — like The Daily’s Michael Barbaro — has become a surprisingly central character in my day-to-day life.

If you are in tech, and haven’t checked out The TechMeme Ride Home, you’re missing out. It’s a simple recipe: every weekday at 5 o’clock, Brian summarizes the day’s tech news, sharing acerbic hot takes along the way. It’s the one podcast I never miss. An ingrained habit that has completely supplanted my other sources of tech news and enabled me to save hours of otherwise productive time in my day. …

Why podcasting may have minted its first billionaire, subscription podcasting is the next great business model, and how to join the revolution

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In 2005, Howard Stern shocked the world by leaving terrestrial radio and accepting a $500 million dollar deal to move his show to Sirius satellite radio. In 2015, he renewed with a 5-year deal for $90 million per year.

People were blown away by the numbers. He was making out like a bandit! Had he been a CEO receiving the same pay, he would have qualified as the third highest paid CEO in America in 2014.

As of today, Howard is getting seriously ripped off.

Here’s why…

Last year I helped a few friends grow their podcasts. They had decided to forgo advertising and instead fund their shows using a membership model. Basically: a small percent of their audience would pay around $5-$10 a month to receive extra content like extended and Ask Me Anything episodes. …

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I was buying a bag of potatoes. A big one. Not because I liked potatoes, but because I wanted to pay my rent.

After years of eating every meal out, blowing money on clothes, and ignoring my bank balance, things had changed. A few weeks prior, I had been dreaming about what kind of sports car I was going to buy. Now I was trying to figuring out how to stay out of my parents basement.

MetaLab had been running for just under two years in November 2008. The stock market was in a free fall and my clients had stopped paying their bills. Some claimed to be unhappy with the work and demanded refunds. …

In the first few years of starting my business, I told myself I’d never let the company get bigger than 10 people. Then 30 people. Then 50 people. I associated more people with more pain. More management headaches. More accounting. More office space. I didn’t want the all the stress.

Hiring hurt. The more people I had, the more stressed out I got, so I told myself that hiring was bad. I built a narrative that I needed to stop hiring, because every incremental hire made my life more difficult.

This was insanely stupid and limited my company’s growth for the first couple years. At my company, MetaLab, we make money by selling our time. The more team members, the more time to sell to clients, the more growth and opportunity. We had amazing clients lining up out the door, but because hiring more people made my life difficult, I only worked with a handful of them. I let growth stall and made a completely illogical business decision because it hurt to hire. …

How I designed my perfect day by fixating on what I hate

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Last year, my business partner Chris and I sat down to think about what we wanted to achieve at Tiny. We thought up all sorts of lofty goals, but when we really got down to it our true goal was actually pretty simple. We wanted to do something many successful business people seem to struggle with: we wanted to actually enjoy our time at work.

Too many of our friends, while wealthier and more successful than us, had objectively shittier lives. Calendars packed. On planes all the time. Marriage in shambles. Not enough time with their kids. …

Charlie Munger on why humans make horrible decisions

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Everybody knows about Warren Buffett, but few people outside of the investing world know about his business partner, Charlie Munger. While Buffett’s life has a singular focus on business and investing, Charlie is a Benjamin Franklin styled polymath with interests ranging from architecture (he refused to donate a dormitory to The University of California unless he could specify its exact design), to theoretical physics (he often hosts dinner parties with the world’s top physicists and holds his own), to psychology (which he’s lectured about at Harvard).

Last year, I came across the aforementioned lecture that he gave at Harvard back in 1995. It’s called ‘The Psychology of Human Misjudgement’ and it’s about the many ways that we fool ourselves into making horrible decisions in business, investing, and life. My business partner Chris and I spent months listening to it over and over again in our cars in order to drill it into our heads, and it has saved us from making a ton of idiotic mistakes ever since. …

Warren Buffett is famous for handshake deals and one-page contracts. He often buys multi-billion-dollar companies after a few phone calls, usually without ever meeting the management team in person or visiting their facilities. Not only that, but he typically pays below market prices and avoids dealing with investment bankers. Despite all this, he has amassed a collection of over 65 wholly owned companies, ranging from See’s Candies, to Dairy Queen, to Fruit of The Loom.

Today, his holding company, Berkshire Hathaway, is worth almost $500 billion.

So, if he pays below market, refuses to negotiate, and won’t even visit them in person, why do wealthy entrepreneurs and families sell to him?

When I first started MetaLab, Dan Cederholm was my hero. Bulletproof Web Design was the first book I read when I was learning the ropes, and I regularly reverse engineered his stylesheets on SimpleBits to learn CSS tricks. Anything he did, I did, and I drove my early frontend developers nuts, getting them to implement every little 1-pixel detail I’d learned from Dan.

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To give you a sense of what Dave was contending with, here’s a photo of me holding the first iPhone.

I remember meeting another favourite designer, Dave Shea, at a conference back in 2008. When he happened to mention he knew Dan, my jaw hit the floor. “Wait. WHAT?! Those CSS drop shadows he does! The Cork’d logo?! THE BEST! What’s he like???” I was gushing. “He’s… just… a really nice, talented guy…” said Dave, giving me a worried look before shuffling off to grab a drink from the bar, shoulder checking every once in a while to make sure I hadn’t followed him. …

Building Products The MetaLab Way

“You gave me a PDF full of incoherent garbage about chatbots and wasted months of our time!” I was visiting a client, the CEO of a successful venture backed company, and he wasn’t happy. He had hired us to help his team think through the next version of their product, and instead of jumping into a design phase, like we usually do, we had spent months building out a strategy deck trying to rethink the future of his business.

He was frustrated. He had come to MetaLab because of our reputation for building amazing products, and there we were, months into the project, handing him a 50-page deck about chatbots, AI, and a bunch of buzzwordy bullshit. …


Andrew Wilkinson

I run Tiny ( @awilkinson

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