The four companies in the inner circle— Facebook, Apple, Amazon, and Microsoft— have a combined market capitalization of

The first time I spoke with Jennings Anderson, I couldn’t believe what he was telling me. I mean that genuinely — I did not believe him. He was a little incredulous about it himself. I felt like he was sharing an important secret with me that the world didn’t yet know.

If digital products give you vertigo, you don’t have to hock ebooks or pitch courses to diversify your income. Hover closer to home and listen to what clients and prospects are asking for — can you retool your services to give them what they need while still making a profit? Can you offer off-shoots, remixes, or sprints? Experiment with products, review your results quarterly and tweak your process and mix until you have margins that feel sustainable. Remember, this is a test and learn approach. Some ideas will fall into the trash heap while others will take you places you never expected.

So you know what I did? I called them, and I told them that this makes me feel bad. And you want to know what they did? They agreed that they would take it off their platform just so I could feel better. That’s why I fuck with Netflix. Because they paid me my money, they do what they say they’re going to do, and they went above and beyond what you could expect from a businessman. They did something just because they thought that I might think that they were wrong.

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that if a random event is repeated enough times, individual results might not matter. So, if you are playing in a casino with a game that has negative expected value (as they all do), it doesn’t matter that you win occasionally. The law of large numbers implies that you will lose money.

So it’s quite the plot twist that Chappelle is engaging in the same sort of behavior he’s railed against for the past few years. Sure, Chappelle’s initial anger over Chappelle’s Show being streamed on HBO Max and Netflix came from the fact that he wasn’t getting paid for it. But that ship has sailed. Chappelle will never see another dime from Chappelle’s Show. No, the reason he reached out to Netflix was, by his own words, over something other than finances:

There was a time I was subsisting on creating copy for freelancers’ portfolios and doing site audits because I was going through a tough time and didn’t have the mental capacity for anything substantial. Clients gained access to my expertise while I weathered a mental health slump (to put it fucking mildly, but I digress).

Offer coaching services or workshops where you help a client’s social media or internal copy team up-level their copy skills. Any internal team can benefit from a refresher or external perspective, no matter how senior its members are. Show a client — once their brand platform has been created — how to practically adapt their standards across channels, i.e., social media, website, newsletter, print collateral, advertising, video story-boarding, etc.

I like working for Netflix because when all those bad things happened to me, that company didn’t even exist. And when I found out they were streaming Chappelle’s Show, I was furious. How could they not know?

Special thanks to Jennings Anderson who looked over an early draft of this post and helped me refine it. Also, as usual, the views expressed herein do not represent those of my parents, my wife, my dentist, or my employer.

For the past few years, since his return to mainstream consciousness, Chappelle has taken it upon himself to wave the flag of comedians’ right to tell any types of jokes they want, no matter whom they offend. To prove this point, Chappelle has peppered his stand-ups with jokes at the expense of the trans community. And as members of that community have voiced their anger and hurt over these jokes (which are among the least funny or creative in his arsenal), Chappelle has only responded with defiance and more disregard. He’s labeled the backlash as censorship or cancel culture instead of thoughtfully addressing the feelings and worries from a community continuously terrorized by prejudice and hate.

If there’s anything I’ve learned in seven years of consulting, it’s this — your income is rarely stable, regardless of talent and tenure. You could be dealing with an illness, a global pandemic, shifts in the economy. etc. What you can do to mitigate what you can’t control is focus on packaging your services at varying levels so you have a stronger mix of potential clients and you can weather downturns and Sahara-level project droughts.

The open secret Jennings filled me in on is that OpenStreetMap (OSM) is now at the center of an unholy alliance of the world’s largest and wealthiest technology companies. The most valuable companies in the world are treating OSM as critical infrastructure for some of the most-used software ever written.

If digital products give you vertigo, you don’t have to hock ebooks or pitch courses to diversify your income. Hover closer to home and listen to what clients and prospects are asking for — can you retool your services to give them what they need while still making a profit? Can you offer off-shoots, remixes, or sprints? Experiment with products, review your results quarterly and tweak your process and mix until you have margins that feel sustainable. Remember, this is a test and learn approach. Some ideas will fall into the trash heap while others will take you places you never expected.

Charge for “tear downs,” where you take a client’s existing collateral and show them tactically ways they can improve. Email marketing superstar, Val Geisler, used tear-downs as a way to market her expertise, but you can certainly charge people for this in the same way web designers/UX pros charge for site or digital media audits. I’ve charged clients for site and social media audits, closing with tactical, prescriptive actions they can take immediately to solve their most glaring problems. The concept here isn’t just to tell people what they did wrong, but it’s about getting them to get it right.

Read that again. Chappelle does words for a living. He didn’t say he called and asked for Netflix to remove the show because of money. He said he called to say “this makes me feel bad.” And Netflix responded by pulling the show “just so I could feel better.”