How a VC investor grew her newsletter to over 100,000 subscribers

Codie Sanchez finds interesting ways to make money and then reverse engineers them for her audience.

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There’s a somewhat common career path in which a journalist actually transitions to the very industry they cover. MG Siegler, for instance, got his start as an intrepid reporter for TechCrunch and spent five years at the publication covering VC-funded startups before being hired by Google Ventures as a general partner in 2013. Kyle Russel followed a similar journey, writing for outlets like Business Insider and TechCrunch before accepting a role at Andreessen Horowitz in 2015.

Prior to jumping on the phone with Codie Sanchez, I assumed this was the route she had followed as well. Her website bio described her as a “reformed journalist turned institutional investor,” and so one of the first questions I posed for her was whether she broke into her industry as a financial journalist.

I couldn’t have been further off. “I covered war zones,” she told me. “My region was Latin America, so places like Venezuela and Argentina, basically anywhere where there was conflict amongst humans.” The job burned her out relatively quickly. “As a 25-year-old I got pretty jaded to journalism in general and just felt like, gosh, my last name is Sanchez, and their last name is Sanchez, but their life looks just so much different from mine. I tried to figure out what that difference was and determined that it was entirely monetary. And so that's why I got into finance originally was to understand that dynamic and maybe make some sort of a difference.”

Still, the journalism bug hasn’t left Sanchez completely; every week she sits down to write a several thousand word newsletter that now reaches the inboxes of over 100,000 recipients. Not only has it raised her profile within the VC world, but it’s quickly becoming a powerhouse business of its own, driving six figures in revenue. In our phone call, Sanchez walked me through why she launched the newsletter and how she’s approaching monetization.

Launching the newsletter

Sanchez’s experimentation within the newsletter space came in fits and starts, partially because many of her employers didn’t like that she had a side hustle. “They hate when their employees have personal brands,” she said. “They don't want you to have any of your own marketing. Their philosophy is, ‘we pay you really well, so shut up and do the work.’”

Of course, as Sanchez moved up within the industry, she was granted more leeway in how she spent her free time. In the span of about a decade, she went from analyst roles at places like Vanguard and Goldman Sachs all the way up to managing director at Entourage Effect Capital, a VC firm that specializes in investing in cannabis startups. At that level, there aren’t many people who can say no to her extracurricular activities.

So how did she end up launching a newsletter? It came in three iterations spread out over several years. 

The first version was called Selling South and focused on conducting business negotiations across country borders. It mostly consisted of a blog that was monetized through sponsorships and a small conference, and Sanchez was forced to shut it down once her bosses got wind of it.

Her second media venture was a newsletter and podcast called The Struggle Isn’t Real. “I sent out a Friday email that listed things aimed at making someone’s life easier,” Sanchez said. The podcast’s iTunes description asserts that “you were not put here to live an ordinary life, you were meant for something more.” She didn’t do much to promote the newsletter, but it grew organically anyway, with large spikes in signups after she spoke at conferences or made high-profile media appearances. “I think I got that one up to like 10,000 or 12,000 subscribers.”

That went on for about a year before Sanchez discontinued it, mostly because she was too busy with her day job to keep it running. But she kept the subscribers on her mailing list, overpaying for a Mailchimp account that she wasn’t even using. 

That list came in handy when the pandemic shutdown hit and Sanchez’s constant travel came to a halt. She used the sudden influx of free time to launch Contrarian Thinking, a newsletter that covers, as it says in its description, “all the ways to build wealth and impact we should have learned in school.”

What does that actually mean? Each week, the newsletter dives into a different niche business that can generate revenue through unconventional methods and a relatively small upfront investment. In some cases, Sanchez will actually test out the business herself. “For instance, I bought a piece of land for $10,000 and put it on something called Hipcamp” -- a sort of Airbnb marketplace for camping -- “and rented it out to some campers.” In other cases, she interviews someone who runs an interesting business and then walks Contrarian Viewer subscribers through how the entrepreneur built their company. An edition published in early April, for example, detailed how a woman named Lisa Song Sutton launched a “mini storage unit” company that generates $120,000 in annual profit. The article is 1,200 words long, contains several photos, and is broken down into four steps. 

Sanchez readily admits that her newsletter distribution isn’t ideal; she basically sends out three separate versions of the same article to lists managed on Mailchimp, SendFox, and Substack (she said she’s building out a website that will allow her to consolidate all three lists in a single place). Despite this inefficient setup, the newsletter has grown rapidly. She started out with her 12,000-or-so subscribers left over from her last media venture, and by July 2020 it had grown to 30,000 signups. Today, that number is north of 100,000. 

How she monetizes

Contrarian Thinking generates revenue in a variety of ways, both directly and indirectly.

First, it helps her with deal-flow, both in terms of attracting new investors into her fund and also introducing her to founders in search of capital. This is the reason that large VC firms like Andreessen Horowitz have plopped down a lot of money to invest in journalistic content. “I think Andreessen Horowitz is one of the gold standards, and they have been for a long time,” said Sanchez. “In the future, your audience is going to be one of the most important ways that you raise capital.”

Contrarian Thinking also often covers Sanchez’s various side businesses -- the aforementioned camping property being one of them -- and through affiliate links she’s been able to track about $100,000 in sales that have come directly from her newsletter. Despite this success, she’s never sought outside advertisers. “It's mostly just because it's a lot of work,” she said. “Based on the size of my list, I just didn’t think I’d make enough monetarily to make up for having to chase down sponsors.” 

In early 2021, Sanchez began brainstorming ways she could generate direct revenue from Contrarian Thinking. In February, she launched Contrarian Cashflow, a membership program that allows members to dive deeper into the businesses she profiles in the newsletter. She’ll schedule a live call between her, the entrepreneur being featured, and the members. “We go deep into the business, and if you want to execute on it, you're going to get a bunch of resources in order to do that, including a step-by-step playbook.”

Sanchez started out by launching a $500 lifetime membership, and when we spoke in March she had already generated about $70,000. She plans to soon roll out both a monthly and annual membership that will likely cost upward of $250 a year. Though she uses Substack for distributing her free newsletter, she forwent that platform’s payment system completely and attached a Stripe account to a simple landing page and signup form.

Future ambitions

Thus far, Contrarian Thinking has been little more than a side hustle for Sanchez; she estimates she spends about 10 hours out of her 80-hour work week on it. I asked her about her longterm ambitions for the newsletter. “I’m not really interested in becoming a  guru or influencer myself,” she said. “I'd like to bring on other critical thinkers in different verticals.” She gave the example of a Contrarian University aimed at teaching college kids skills they’ll actually need in their careers. “Maybe another one would be Contrarian Health, and I’d find some people that want to write on that subject. Right now, my face is on the logo, but I'd like it to continue to evolve from just a business of Codie, to a business of a bunch of critical thinkers.”

For now, though, she’s focused on the main newsletter and its nascent membership business. As a former mainstream journalist, she’s excited about the world that newsletter platforms like Substack are unlocking. “I believe this may be the future of news,” she wrote recently. “...Creation of small new startups, consolidation into big behemoths, and then breakups as the old models are attacked by more nimble upstarts. We are in a disaggregation phase.”

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Simon Owens is a tech and media journalist living in Washington, DC. Follow him on TwitterFacebook, or LinkedIn. Email him at simonowens@gmail.com. For a full bio, go here.