How to build a $525M newsletter portfolio

👋 Hi friends -

Welcome to The Newsletter Growth Memo. Twice a month, I share short reflections with my newsletter clients + other operators.

Zero formality, ads, or affiliate links - just a guy sharing learnings from working with media operators doing $25k-$2M+ / month with newsletters.

New reader highlights: Henry, Founder @Tricycle Day | Rich, CRO @ Launch Potato (parent company to FinanceBuzz) | Devon, Managing Editor @ US News & World Report | Mike, Head of Sales @ BiggerPockets

Industry Dive is one of the best bootstrapped media/newsletter case studies of all time.

They’re a portfolio of 35+ niche, B2B newsletters that do well over $100M.

Started in 2012, they sold for $525M within 10 years.

Their ethos, “Who reads, not how many” is why I started inviting the biggest newsletter founders/execs to this little email list of mine!

I think ID is fascinating. So I hired a bright Wharton intern to research their origin story, scouring every public source for information.

What she sent was great (here’s her raw doc), but incomplete - there’s just not a lot out there about the beginning of Industry Dive!

I wanted to know about the decisions they made to go from 0 → $10M:

So this summer, I interviewed their entire founding team - Sean Griffey (CEO), Ryan Willumson (CRO), Eli Dickinson (CTO), plus their heads of sales (Imogen), growth (Robin), and editorial (Davide).

Six interviews. Six perspectives on how to bootstrap a B2B media company from $0 to a $500M+ exit.

I’ll cover:

Sean, Ryan, and Eli didn't start from scratch.

They cut their teeth at FierceMarkets - a successful B2B media company with publications across telecom, healthcare, and tech.

When Fierce was acquired by Questex Media (owned by Audax, a private equity shop) in 2008, Sean was promoted to run the business.

But there was a problem.

All of the cash the company generated was going to pay down the debt of the rest of the Questex portfolio.

The team couldn’t do half the things they wanted to for the business.

Ryan went to Sean to resign in 2012.

And then Sean made what he calls "the number one sale of my life":

“Ryan came to me one day and resigned. But I realized Ryan is the best person I work with day in and day out. So instead of him going somewhere else and being part of a founding team, I said, why don't we do it together?”

They partnered with their third co-founder, Eli Dickinson, and started V1 of Industry Dive with five publications.

By the end of 2012, they had 2 FTEs, a few interns, and shared a small converted rowhouse with the Albanian embassy.

Note: Some numbers estimated, e.g., 2014 revenue is based on the 3-year % growth they disclosed in their 2018 Inc 5000 feature

I almost acquired a general B2B publication, The Neuron, late last year.

I’d love to buy something in the future. So this list really is for me as much as it is for you.

Here’s what I’d keep in mind if I wanted to take a B2B publication to $10M+ in revenue.

Industry Dive launched with $400k in funding.

Sean, Eli, and Ryan didn’t pay themselves for the first 18 months.

They raised another ~$500k extension after nearly running out of runway in 2013 while building an audience large enough to sell into.

Nearly all of the successful newsletters that get talked about - The Hustle, Morning Brew, 1440 - raised small rounds and chose to never raise again or to look at private equity/debt vehicles.

There’s a lot of danger in raising VC money in media - I would be shocked if TheSkimm founders made a substantial amount of money in their sale (they raised $29M).

Industry Dive had a specific formula for selecting niches:

Important to note: Competition didn’t matter - Healthcare was already crowded, even at Fierce.

Most media founders obsess over list size.

Industry Dive launched 5 small, niche newsletters simultaneously - utilities, waste, construction, marketing, food, and education.

This gave them diversity as ad dollars ebbed and flowed across markets.

And specificity within lists (Marketing Dive, Social Media Today, and Retail Dive all overlap in audience) made for better products.

Specificity also became the base for their future launches.

Often, similar industries (Grocery Dive, Restaurant Dive, Retail Dive) acted as seed audiences.

This worked equally well with functions - because ID collects rich 1P data, they could seed HR Dive from all of their existing publications.

Speaking of data, Industry Dive built a CDP that pulled together demographics, behavioral data, and interactions across all of their verticals.

Instead of slicing the audience into tiny segments to sell at a premium from day 1, they used it to deliver on performance guarantees with ruthless efficiency.

If a client bought a webinar package with a guaranteed 50 leads, the question wasn’t “Who can we sell this to?” — it was “What’s the smartest way to fill this quota?”

1P data also informed content strategy and client insights: editorial could see which stories attracted top executives, even if that content didn’t draw the most page views.

Industry Dive won early by spotting distribution shifts before competitors:

Robin built her growth team to be channel-agnostic so team members could take advantage of new opportunities like these.

Partnerships were also a big part of growth:

In the first few years, ~40% of Industry Dive’s growth came from trade associations, events, and niche communities.

The offer: “We’ll run your ad for free if you put our signup in front of your audience.”

It was a pure barter that brought in high-quality subs and often turned partners into paying advertisers once they saw results.

At Fierce Markets, custom content was editorial-controlled, creating conflict when marketers tried to influence stories.

From day one, Industry Dive allowed client-controlled content (white papers, webinars) with quality guardrails, but no editorial input.

This eliminated internal "battle taxes" and let sales move faster on fulfilling deals.

ID refused to build products (e.g., a construction product directory) or pricing models unless they could work for all verticals.

Ryan believes gravity pulls you towards complication - you need to fight that.

Their early products:

Primary newsletter sponsorships: Flagship primaries, you know the deal

White paper lead programs: They’d run a sponsor’s white paper behind a form with a lead guarantee - an easy bridge from brand to performance budget.

Webinars (often pseudo-live): If a client was happy with white paper leads, they’d pitch a webinar next - pre-recorded with live Q&A to reduce execution risk

These work for all industries. If you have no custom content, consider starting here.

In year one, Industry Dive had no choice but to rely on freelancers.

One editorial director was managing 5 verticals, with five freelancers churning out content.

It was the only way to get volume with almost no budget.

As the business grew, they flipped the model, realizing that in-house reporters could:

Davide was deliberate about who he hired.

He scouted undervalued freelancers, brought them in full-time, and invested in their growth. Several went on to run teams and win national B2B journalism awards.

Davide believed Buzzfeed’s snappy editorial formats, like listicles, could be brought to B2B and married with the depth that executives wanted.

So he took over Utility Dive ("the hardest vertical") and developed their playbook for turning recent grads into industry experts with original reporting. He:

An early example from discussions with teachers/education leaders: A 2013 viral "13 ways iPads will be used in schools" listicle that tripled pageviews for K-12 Dive overnight.

Imogen's sales philosophy: reps own the full stack from prospect to close to renewal.

They learned by doing - shadowing calls, reviewing sales call recordings like elite athletes watch game footage, and iterating fast.

If you sat in the ID office, you’d see new sales reps calling prospects by week 1.

The team also had full autonomy to pitch new products (as long as they could be sold portfolio-wide):

A rep sold a webinar sponsorship before ID had a webinar capability.

Their Trendline product came out of a sales team suggestion.

Early sales were simple: HTML email blasts, newsletter sponsorships, LinkedIn group sends.

Over time, the approach shifted to diagnosing client needs and packaging multi-touch campaigns.

Upsells weren’t framed as “Here’s something else we sell” but as “Here’s how this will hit your KPIs faster.”

That might mean a sponsorship to warm up an audience, followed by a white paper push, and ending in a webinar for engaged leads.

This was significantly easier because reps came armed with industry knowledge and insights on what executives were reading in their editorial.

They could advise on what topics decision-makers cared about and show when a client’s buyer was active across multiple newsletters, making “wider net” buys an easier sell.

Sean's insight: "If you want to look bigger than you are, invest in design."

From day one, Industry Dive looked polished and professional despite being a scrappy startup.

This design investment helped them compete with established players for both audience and advertisers.

The co-founders set the tone early - taking out the trash, jumping in to write stories, etc.

Ryan led sales, but if you shadowed him at a trade show, you’d see him running around collecting email sign-ups for audience development.

There was hustle, and ideas/people were judged on merit, not tenure.

That culture led to actively recruiting undervalued new grads and training them into elite operators, creating a bench of “builders”.

And you see it today - how many companies get to $100M+ with the same leaders they had at $1-5M?

It’s exceptionally rare to find 1 leader who can mold to each stage of a business like that, let alone 6.

That’s the letter.

- Nathan May

P.S. Taylor McKnight, their 1st designer (and eventually head of design) wrote a beautiful recap of his 12 years at ID. It’s where I got all of these photos. I highly recommend!