How a blog about the VC industry generated over $1 million from online courses

John Gannon built an audience with VC job postings and then monetized through a mix of online courses, productized services, and sponsorships.

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Coming out of Columbia Business School in 2008, John Gannon had to choose between two career paths: launching a startup or joining a venture capital firm. While he certainly had the entrepreneurial bug, he also held a deep fascination with the VC industry. “I got interested in venture capital back when I was just a couple years out of college and started to read about VC firms,” he told me. “I remember in particular reading about Benchmark, which is one of the most storied firms in the world, and I don't know what it was exactly, but I kind of got hooked on the idea.” Ultimately, his choice was driven by the fact that he and his wife decided to start having children. “I thought, you know, venture capital is a little bit more stable than doing a startup.”

So in 2008 Gannon joined a $160 million VC fund that specialized in sectors like IT and digital media, and it was while working there that he realized there wasn’t much high quality information on the internet about the VC world. “I had people coming to me asking me how to break in,” he said. “I had a lot of empathy for them, because when I was in business school, I was reaching out to venture capitalists, trying to get them to spend time with me to tell me about the industry and to network and talk about jobs and stuff like that.” While it’s more common today for VCs to write their own blog posts or sit down for long podcast interviews, back then it was much more of a behind-the scenes profession.

That same year, Gannon launched a Wordpress site at johngannonblog.com and began writing about the industry. At first, he mostly curated links to outside resources, but over the next decade the site expanded into job listings, online courses, industry surveys, productized services, and multiple newsletters. In 2022, he left his salaried job to work on it full time, and to date it’s generated over $1 million in just course sales alone.

In a recent interview, Gannon explained to me where he found his initial audience, how he launched his courses business, and why VC firms now pay him to announce their recent hires and investments.

Let’s jump into it…

Pivoting to job listings

For the first few years of the blog’s existence, it attracted very little traffic. But in 2015, Gannon had the lightbulb idea to begin aggregating industry job postings, which at the time were scattered across various job boards and VC websites. At first, he simply created a new Wordpress page for each job listing, with the job title as the page’s headline and all the requirements pasted within the body. At the bottom, he’d link to the actual website where you could apply for the job. Eventually, he installed a specific Wordpress widget that signaled to Google that the page is a job listing and should be indexed as such.

The explosion in traffic came almost immediately. In fact, Gannon recently posted a chart showing how quickly it grew:

Given that Gannon still had a full-time job, he initially struggled to post jobs to his site more than two times per week. “Then I brought on a virtual assistant to do it so that it would be more reliable and at scale, and that's when I really saw the traffic ramp up.” To accomplish this, he formulated a checklist that involved visiting the major job boards, finding the appropriate jobs, and then migrating all the important information back to his website. Eventually, he added a Google form where VC firms could submit jobs directly to his site, and he also started segmenting the job listings by city. Within a few years, users went from stumbling onto his site from Google searches to visiting it directly to check if there were any new listings.

Expanding into newsletters

With so much of his traffic coming from Google, Gannon recognized that he needed to diversify his referral sources and also establish a more direct connection with his audience. He’d never had much interest in social media, but he did like the appeal of writing a newsletter, so he started embedding a signup form at the bottom of his job listings that promised to email subscribers when new jobs were posted.

At first, subscribers received a once-a-week newsletter called VC Careers. In addition to the new job postings, it also included a piece from Gannon giving advice on how to break into the industry. Eventually, that one newsletter expanded to several sent throughout the week, each focused on a different topic. On Mondays, for instance, he sends out a VC deals newsletter that rounds up publicly announced startup investments. On Thursdays, he produces a “moves in VC” newsletter, which mainly rounds up major hirings at VC firms. Rather than creating signup forms for each newsletter, he automatically sends all of them to every subscriber while also giving them the option to unsubscribe to the ones they don’t like. “I've seen no appreciable increase in unsubscribes or complaints or anything,” he said. “So in essence, I was able to 3X my ad inventory overnight by launching these additional newsletters.”

While Gannon writes the main anchor essays for the newsletters, he’s also amassed a team of contractors who help aggregate all the deals, announcements, and job postings included in them, and this helped him scale up his newsletter production and audience growth. He also began buying ads in other newsletters, which allowed him to pay as little as 40 cents per new subscriber, which is well below the industry average. 

A few years into his first newsletter, he came up with another key growth lever: audience surveys. Specifically, he began surveying his readers every year to collect salary data and other metrics, and then he’d publish the results to his website. It didn’t take long before this article began ranking high in Google results whenever people searched for VC salaries, and while the web article contained all the topline results from the survey, you had to enter your email address if you wanted to receive the full report. This served as a huge lead magnet that increased his newsletter signups considerably. 

To date, he’s grown his email list to 25,000 subscribers, most of whom either work in VC or want to work in VC. And as it turns out, this demographic is a financially valuable one to serve.

Launching online courses

Gannon didn’t set out with the intention of launching courses; instead, he kind of fell into it sideways. “I started with live experiences, either one-on-one coaching or trying to get five people to sit in a conference room with me and let me talk to them about venture capital.” This led to him conducting multiple live sessions on how to break into venture capital. “I recorded it one of the times, and then I had someone on my team carve it up and then create a Slidecast [presentation] out of it.” He then took this recording and began selling it on Gumroad as a VC Jumpstart course. He plugged it on his website and newsletter.

To Gannon’s surprise, he generated several thousand dollars within a short period of time. So over the next few years, he built out an entire menu of courses and productized services to offer his audience. They include:

• VC Job Launchpad: This is a spruced up version of that original course, and he sells it for $348.

• Investment Thesis Playbook: This teaches customers how to evaluate a potential investment deal, and he sells it for $199.

• Custom VC Resume + LinkedIn Review: This is a productized service where he’ll review your resume and LinkedIn profile and give you video feedback, and he sells it for $348.

• VC Financial Modeling Bundle: This covers “all of the key VC financial modeling concepts you’ll need to know for interviews and when you're on the job,” and he sells it for $248.

• Ace the VC Interview: This is to prep candidates for an actual job interview, and he sells it for $348.

• VC Job Launchpad + Bonuses: This appears to be a bundling of all of his courses into one, and he sells it for $1,394.

Given that Gannon’s courses targeted VCs at different stages of their careers, he needed a better way to funnel them to the appropriate products, so he attached a questionnaire form to his newsletter signup page that asked subscribers basic questions about their needs. “At that point, there are automated pitches that kick in,” he said. “Depending on what I know about them, they'll get pitched certain products.”

Introducing sponsorships

It probably wouldn’t surprise you very much to learn that there are plenty of brands out there who want to reach Gannon’s affluent audience, and indeed he did launch traditional sponsorships that allowed companies to pitch their products in his newsletter. But he also developed sponsorship offerings that were specifically designed around his content.

For instance, I mentioned before that he sends out a weekly VC deals newsletter that curates investment rounds in startups. It turned out that VC firms would actually pay to have their investment round announcement bumped to the very top of the newsletter. The same was true for his “moves in VC” newsletter; those same firms would pay to have their hiring announcements placed at the beginning of an issue so they were more likely to be seen. Gannon upsells these sponsorships directly through the submissions process. “So they have to fill out a Google form whenever they want to submit a deal or a hire,” he said. “And there's a question on the form that asks whether they want to be featured.” Those who opt into the placement simply pay through Stripe.

So why would a VC firm pay to be featured on these lists? “The people working at these firms, they need deal flow — that’s their life currency,” Gannon explained. Hiring and investment announcements play a crucial part in generating that deal flow.

A spinoff business

While his main blog and its associated products take up the majority of Gannon’s time, he also co-founded a related business in 2018 called GoingVC. “I had all of these passive courses, but there was a clear need for folks to have some way to connect with VCs who might be hiring to learn from them and build kind of a community around their job search,” he said. “So our thinking was, ‘Hey, I wonder if we could do a thing where we invite VCs to come talk to a group of job seekers once a week, and then we’d also have a Slack group too.’” The offering is cohort-based, and the company charges around $6,000 to participate. “We've had over 500 people go through the program and  now it's much more well developed with a ton of curriculum.” His co-founder runs the business on a day to-day basis.

GoingVC also has an angel seed investment arm as well, and Gannon leverages the personal network he built up through his blog to drive deal flow. “There's a lot of opportunity there, particularly with this proprietary network and audience that I've built,” he said. “I think for me it's a question of figuring out what's the best way to apply that network. Like should I be starting my own dedicated venture fund? Or perhaps it involves helping, through my platform, put new funds into business? There are a lot of different ways I can take it, and I'm exploring those options right now.”

But most of his energy at the moment is still focused on building out his information products business, since he still sees a huge opportunity for further growth in that realm. “In two to three years, I’d love to be generating a million dollars a year just from the courses — not counting all the other forms of monetization. That would be a pretty great place to be.”