2024 recap: 6 of my favorite media founders

👋 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 $25-500k+ / month with newsletters.

New reader highlights: Welcome to Anthony, Co-founder @Fitt Insider | Sam, Co-founder @The Daily Aus | Brian, VP, Strategy & Analytics @ Business Insider

2024 is winding down.

I’m writing this on a flight to NYC for Ryan Sager + Jesse Watkins’ Duck and Deliver newsletter operator dinner.

Because I’ll fly anywhere duck is involved.

I love to reflect on flights.

So I thought I’d do a little reflecting with you today on a handful of readers I’ve gotten to know in 2024 who I’m thankful to have in my life.

They also all happen to be 6-8 figure entrepreneurs in our industry, so I hope my silly little journaling will double as useful advice.

There are 3 traits they have in common that have helped them bootstrap amazing companies in / around media + newsletters.

And think anyone would benefit from doubling down on these traits in 2025.

1) Obsession

Obsession is a state of both passion and ruthless elimination.

When you’re willing to cut away anything that doesn't serve your singular goal, you’re obsessed.

I’ve met a lot of folks doing 7, 8, 9, etc figures per year and this is by far the most common personality trait I’ve seen - it is in my opinion, table stakes.

So I want to tell you a quick story before I mention two people from our industry who nail obsession.

The Feed is ~10 months old and a hair below $1M in ARR.

I saw this 90-second video clip on making 2024 your year of obsession in January.

It was so motivating that I started The Feed Media 6 weeks later and it’s defined my entire year.

I believe the best entrepreneurs, execs, athletes, etc. have the capacity to be obsessed.

(That’s you).

So, what if you only chose 1-2 things to achieve next year?

And eliminated anything that was not a direct input to those things?

Every week… for 52 weeks.

Imagine how far you’d get in just 1 year - you’d be unstoppable!

I’ve had periods of obsession.

I’ve seen how powerful it can be.

When I was 13 I weighed about 200 pounds and dropped to 130 in 7 months running up and down my basement stairs for 30 minutes a day.

When I was 15 I built a nerdy business creating custom Minecraft maps for famous YouTubers.

I did so much building and content that some days I’d forget to eat. 

That business hit 6-figures before I could drive a car and set me up for life to take more risk.

My problem is I’ve had very little control over when I obsess.

So a lot of my life has been chasing that feeling. 

This year I found it again. 

Here are some people who helped me get there. 

Rowan Cheung

Rowan is the founder of the largest AI newsletter, The Rundown.

Rowan:

• Is 24

• Has built 700k+ followers across X / LinkedIn / Instagram

• Bootstrapped his newsletter to 7-figures almost entirely organically

• Will end this year with well over 1 billion impressions on his AI content

One thing I love about Rowan is that he didn't start learning about AI until 2022.

He had no material advantage over you or me.

But, when he does something, he puts all his chips on the table.

A very quick, very Rowan story: on OpenAI's dev day, he was seated with other top AI folks a few minutes before the keynote began.

The regular thing to do in that scenario: chat a bit, hang out.

Rowan was putting the final touches on 10 separate threads pre-written late the night before on what he thought were the most likely announcements.

Hours were spent meticulously preparing each one.

When the announcements came, he made minor edits, hit publish on the winner, and deleted the other nine.

Obsession!

We spent some time out in SF together with our buddy Wouter in October.

When Rowan wasn’t meeting Zuckerberg or getting invites to AI demos, we’d all jam on ideas (usually over Korean BBQ - Daeho Kalbijim, 10/10).

Here were a few of my favorite takeaways:

• Your yes’s are extremely valuable - choose them wisely; ideally, pick 1 thing to go all-in on and say no to everything else

• Content unlocks tremendous doors - the returns come after sticking with it for a year whereas 90% of other entrepreneurs will quit

• The best founders take action immediately - there is almost 0 time between learning a new piece of information and deciding to act on it or throw it away

Wouter Teunissen

A lot of people know Wouter for single-handedly selling 7-figures of sponsorships for The Milk Road (while in college @ 20 years old).

I think it’s underappreciated just how hard that is.

Juggling classes + exams full time.

How, because he was in the Netherlands, many sales calls had to be taken from 5-10pm.

How exceptionally difficult it is to say ‘no’ in an environment where every social event and distraction is a 5-minute walk away.

But Wouter, like Rowan, does everything all in.

A few months ago he wrote a 30-page biography on one of his heroes and sent it via cold email to meet them.

And it worked!

I really admire Wouter - there’s a wildly positive, irreplicable energy when you’re talking with him.

And a willingness to brute force solutions where other people would give up.

A few takeaways from Wouter:

• None of your heroes are off limits - you can meet them and even work with them; Wouter’s done this 2x now

• A large part of succeeding in entrepreneurship is energy - the more of it you have, the more people will want to be around you, and the more gas you’ll have to stay in the game

2) Move fast and prioritize

I've searched all the parks in all the cities and found no statues of committees.

Too many people (myself included) find too much comfort in the process of deciding… and never get to the deciding itself.

Any remotely reversible decision should almost always be made quickly.

Here are two of my favorite decisive people.

Jesse Pujji

I’m lucky to call Jesse a friend and mentor.

He’s a factory for successful B2B businesses:

• Ampush, one of the OG Facebook ad agencies, grew well into the 8-figures before its sale to Tinuiti / New Mountain Capital

• GrowthAssistant, which hit $17M ARR in 3 years

• Aux Insights, which will hit $5M in its 2nd year

• Bootstrapped Giants, which is at a $1M+ run rate just 6 months in

Because he’s ruthless about executing on the things that matter.

Here are a few of the 20+ things Jesse has taught me to become a better operator:

• Calendar Sundays: Take 2-3 hours every Sunday to plan your week's 2-3 big wins; ruthlessly eliminate everything else

• Focus on 5 sales meetings a week: it's the biggest predictor of getting to $5M+ in ARR in B2B; work backward to calculate the outreach needed for this, and do not do anything else in your week until you’ve hit your KPI

• LinkedIn mutual intros: LinkedIn is woefully underutilized to drive warm introductions, which have 2-3x your average close rate (if we’re not connected on LinkedIn yet, I’m breaking down this process tomorrow here)

• Friendly Fridays: Reserve Friday afternoons for meeting people working on interesting things + going deeper with folks you already know

Tyler Denk

If you're in media, you've probably heard of beehiiv (+ Tyler) by now.

Their growth ($20M+ in ARR in 3 years) has been incredible.

I did some work with Mailchimp + more broadly in media when I was at BCG and I honestly didn’t believe a new ESP would reach a $200M+ valuation.

I was super wrong (the ad network changed my mind).

I can’t think of a company more closely associated with shipping fast, even if it doesn’t mean shipping perfect.

I like how Tyler phrases it - most people over-index on first impressions that everyone forgets about.

Case in point:

• In Oct, beehiiv launched a huge update to their post builder after ~2 weeks of QA

• They knew there would be bugs. There were.

• Half of them were addressed within 2 weeks.

In 2 months no one remembered any of the bugs. They were too busy using the 2-3 other features beehiiv launched by then and thinking “Wow, I’ve never seen anyone make progress this fast”.

A few takeaways from Tyler:

• Ship fast, fix later – perfection is progress’s worst enemy

• Every problem in your company can be solved by talking to your customers

• Every B2B founder should have a newsletter + create content (Tyler’s investor updates are publically available and are an amazing example for any founder/exec thinking about content)

3) Kindness and Empathy

The newsletter space is relatively small.

That’s one of the things I love about it - we're all in this together, figuring it out.

The most successful people I've met this year understand that rising tides lift all boats.

Andrew Warner

Andrew built an 8-figure business in his early 20s, created Mixergy (the OG entrepreneur interview podcast), and now runs the newsletter Bootstrapped Giants.

I spent a weekend at his place in Austin.

Andrew’s got a superpower in cutting to the chase + getting people to a place in conversations where they really feel something.

We did a dinner at his place with a few Austin-based founders one night.

A few whiskeys in, Andrew turns to a guy doing $15M+ a year to my right.

"So, [name], what's the most f*****ed up thing that's ever happened to you man?"

We all spent the rest of the night trading stories about our childhoods, imposter syndrome, etc.

I loved it.

Nothing removes limiting beliefs more than watching a bunch of hyper-successful founders 15 years ahead of me talk about having the same insecurities I often feel.

A few takeaways from Andrew:

• Create spaces where people can be vulnerable – formality kills trust, informality builds it

• What you appreciate, appreciates - tell your colleagues and your team you appreciate them 2x as you think you should, more on that from Andrew/Jesse here

Tim Huelskamp

Tim and I have gotten to know each other more recently.

Which is exactly why he’s on my list.

The ratio of ‘let me try to help’ to time spent with Tim is off the charts.

He's been an open book about the back-end of 1440’s marketing analytics and the entire 1440 team has been incredibly generous with their time.

We love to trade what we see working and I’d like to think both of our teams are all the better for it.

A few takeaways from Tim:

• Be curious - Tim is constantly asking questions despite running the newsletter business every F500 web-first media company would kill to have

• Don’t take yourself too seriously – Tim is wicked funny & informal while still pulling off being an absolute ace entrepreneur… my favorite kind of people!

That’s the letter.

- Nathan

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