The Offers You Shouldn't Accept.

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13 months ago, I said “Yes” to a check I knew I should have rejected, but we’ll get to that in a little bit.

Last week, I crossed the 40,000 subscriber mark on Young Money. Not a bad way to kick off Summer 2023.

However, in April 2022, I was in a much different spot. 13 months ago, I had less than 6,000 readers, and some serious life decisions were around the corner. I had to decide if I still wanted to move to NYC for business school, and beyond that, I had to decide if I was going to pursue a “traditional” career if I did plan to attend business school.

I liked the idea of doing my own thing and making a living as a writer, especially after a year of carefree living, but I had one small problem: a blog with 6,000 readers isn’t exactly a sustainable business. Sure, there were signs that I was gaining momentum: my growth rate was accelerating, some big names were enjoying Young Money, and, most importantly, I could tell that my writing was improving.

There was just one issue: I hadn’t actually made a dime from any of this.

And while I definitely romanticized the idea of saying “F*ck the system, I’ll do what I want,” I’m a realist who enjoys spending money on fun stuff, like $16 espresso martinis in the West Village, which meant that at some point, I would probably need to make some money.

In the blogging/newsletter business, there are two ways to monetize your writing: 1) paid subscriptions and 2) advertisements.

Advertisements are nice because they allow you to monetize your content without sacrificing growth. Plus, advertisements look official. In my head, running an ad on my blog would signal that I had “made it.”

So I really, really wanted to land that first sponsorship.

Around this same time last spring, a certain well-known crypto exchange with a seemingly unlimited marketing budget was paying for Super Bowl ads, buying naming rights for NBA stadiums, and throwing cash at newsletter sponsorships.

 That company was FTX.

 FTX’s US division was preparing to launch a stock-trading platform, and they were looking to partner with financial writers and publications for a new marketing campaign. A third-party ad agency that I had previously worked with reached out to see 1) if I could help with some of the copywriting and 2) if I wanted to run an FTX US ad in my blog.

Copywriting was fine, I had no issues drafting some copy to promote their new stock trading/investing platform. But running an FTX ad on my blog? That made me a bit apprehensive.

Yes, I wanted to pop my sponsorship cherry, but did I want to run a sponsorship with a crypto exchange? I was an outspoken crypto skeptic, after all. But I wouldn’t really be advertising crypto. I would be advertising a stock trading platform… that happened to be owned by a crypto company. Plus, in April 2022, FTX was the crown jewel of every VC’s portfolio, and Sam Bankman-Fried was Silicon Valley’s altruistic poster child.

I weighed the options in my head:

On one hand, I knew that the optics of an FTX sponsorship wouldn’t be great. On the other hand, I wasn’t promoting “crypto,” per se.

So I rationalized, as we’re all guilty of doing when we know something is probably a sort-of bad idea but not so bad that we can’t talk ourselves out of it, that the sponsorship would be fine, as long as I only mentioned the stock trading launch.

And on April 14th, 2022, I published my first blog post with a sponsor:

Today’s Young Money is Sponsored by FTX US!

After hitting “send,” I was nervous. Was anyone going to call me a hypocrite? “Why are you working with a crypto exchange if you’re such a critic?”

But I didn’t receive any of those messages. In fact, I just received the typical “Great piece!” and “What did you mean by ______?”

“Cool,” I thought. “I guess I’m good to finish out this campaign.”

Fast forward a few weeks, and I wrote a piece on broken investment theses. In this particular blog, I referenced crypto, SPACs, and NFTs as examples of when investors couldn’t overcome their sunk costs. A few hours after I published this piece, one reader replied and said, “The irony of reading this when you see the sponsor at the top ;)”

While the comment was meant to be more of a joke than a drag, it stuck with me. Whether or not he meant it, that reader was right. You can’t be critical of the very thing that you’re advertising, which brought me to a crossroads: would I be willing to alter my content to better resonate with advertisers?

Ultimately, I decided that going forward, authentic writing should be my North Star, regardless of the financial consequences. When FTX US circled back in August to run another ad campaign, I declined the offer, saying that I didn’t think it would be a good fit.

And, well, we all know what happened a few months later.

I shouldn’t have said yes to that first FTX contract. I knew, from the beginning, that it didn’t make sense for me to align my brand with theirs. But I was seduced by the idea of finally getting paid for my content. Of showing the world, “Hey, look at me. I made it.” These guys were advertising during the Super Bowl, and they wanted to run an ad with me? That’s a tough deal to turn down.

I was so enamored by the benefits of that FTX proposal that I completely overlooked the costs. And don’t kid yourself: every single payment, every single favor, every single everything comes with a cost.

Ryan Holiday has hit on this theme of being particular about the money that you accept several times (here, here, and here, if you were curious), and he’s so right that it hurts.

We tend to only think of offers, contracts, and favors in terms of what we gain:

“She will pay me $20,000 for a sponsor deal?”

“They will set me up in a penthouse apartment if I’m willing to relocate?”

“The bonus is $100,000?”

“He wants to buy me that new suit/watch/car?”

And the upside is always, always, seductive. That’s the point. But every asset has its corresponding liabilities, and every benefit comes with its own costs.

With the FTX deal, I was risking both my reputation and my audience’s trust for, what? ~$500 per ad? What if FTX had collapsed in May 2022? No one would have given a damn that I was “just advertising FTX US’s stock trading platform.” I would have been another promoter associated with a scam. And you can’t just exchange that $1500 for an intact reputation.

I was lucky that 1) this was a short-term campaign, 2) I was adamant that I would only mention their stock platform/refer to FTX US as an “all-in-one” solution, 3) I quickly course-corrected and apologized to concerned readers, and 4) a lot of people much smarter than me were drinking the FTX Kool-Aid at the time.

Still, FTX’s collapse was a wake-up call to me that I was very, very close to catching some serious collateral damage.

Fortunately, an ill-advised sponsorship deal is a short-term mistake that can be corrected. But we all face other tempting, seemingly-lucrative “offers” that can prove much more difficult to escape.

• Promotions bring prestige and hefty bonuses… but you forego your freedom and your time.

• Favors open previously closed doors… but they become permanent IOUs.

• Athletic scholarships offer free school… but you have to dedicate 50+ hours per week to your sport.

• Companies acquire startups… but founders have to sign noncompetes and stay with their new firms for at least two years.

• Publishing houses offer lucrative book advances… but you lose your control and much of your upside.

The list goes on and on. And it’s not that all of these situations are inherently bad, but you can find yourself in a tough place if you ignore the non-monetary costs associated with each benefit. Plenty of seemingly good things are really just well-disguised traps.

Be wary of temporary “wins” that permanently impair your control of your future. Lucrative bonuses and lavish gifts may seem benevolent on the surface, but they are often gateway drugs to a lifestyle that forces you to maintain that high-dollar paycheck. Big checks and sponsorships might improve your financial situation in the short term, but they can erode the audience trust that made your content so valuable in the first place.

So, next time you’re considering a proposal, whether it be a promotion, job offer, favor, or something else entirely, ask yourself one question: What is the cost?

- Jack

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Jack's Picks

• As you guys know, I love to travel, but finding good flight deals is always a pain. Luckily, Going (formerly Scott’s Cheap Flights) monitors 900+ destinations to send you the best deals as soon as prices drop. Kickstart your summer travels by checking out Going, and get 20% off their first year of a premium subscription with code: JACKRAINES.*

• I really enjoyed Nick Maggiulli’s latest piece on the liabilities of success. I’m also about to enjoy dinner with Nick tonight. Sometimes the Twitter folks link up IRL.

• Paul Millerd wrote a good Twitter thread on self-publishing vs. traditional publishing for authors.

*Sponsored content and/or affiliate link. All sponsored content is vetted by me and helps keep these blog posts free 🤝