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INTERVIEW 🎙️

Tim Huelskamp, Co-Founder & CEO at 1440

Tim Huelskamp is the Co-Founder and CEO of 1440, a daily newsletter delivering fact-focused news to over 4 million readers. Launched in 2017 with just 78 subscribers, 1440 has grown into a leading media company, emphasizing unbiased reporting and concise content.

Prior to founding 1440, Tim spent nearly a decade in private equity and venture capital, providing strategic support to technology companies. He is also a co-founder of Fifth Star Funds, a venture philanthropy fund investing in Black tech founders in Chicago. Under his leadership, 1440 has achieved significant growth, earning a spot on the Inc. 5000 list of fastest-growing companies.

Tell us the problem you’re trying to solve, and why this?

We started this seven years ago. I was in private equity before this, investing in and operating companies to help scale them. My co-founder is a PhD scientist who worked on Capitol Hill. Super smart guy. We both had the same pain point: the media wasn't delivering in two key ways when it came to daily news. First, media by design is very niche or verticalized. You’ve got sports, politics, culture, technology, local—so many fragmented sources.

We wanted something that was an inch deep, mile wide, in a world that’s mostly the opposite.

Second, especially in the U.S., everything felt so polarized. It's left versus right, opinion-driven, everyone yelling at each other on TV. You don’t even learn that much, your blood pressure just goes up. We love learning, and we wanted to find useful, unbiased information. But no one was helping us do that. So, we built it ourselves. We started with a newsletter to 78 friends and family. The technology is pretty simple. Back then, we used Mailchimp. We had this thesis that a product like this should exist. We wanted to see if others agreed. And they did.

Looking back, the very first email we sent—while it looked hideous—is not that far from what our product looks like today. Sure, we’ve iterated like crazy on the design and features, but the core is still the same. It’s a product for curious people who want to learn. People who want to know what’s going on in the Middle East, what CRISPR is and why it matters, or even fun stuff like Michelin-starred restaurants or top places to visit in Australia. But everything gets in the way of learning, and no one was helping solve that. So, we built something to change that.

As a private equity guy, how did you look at it from a business perspective?

Luckily, there were a few newsletter companies that came before us, and we made a point to learn from them. The Hustle had been around for a couple of years and was eventually acquired by HubSpot. Morning Brew was live. The Skimm was live. Axios was just launching. One thing I really admired about the business model was that the unit economics were fantastic, if you could find white space in the market and consistently deliver for the customer.

That’s something a lot of young entrepreneurs don’t always appreciate: you have to deliver value to your audience every single day. They have a million choices, and if you don’t show up for them, they’ll go somewhere else.

But if you do show up—if you retain your readers for multiple quarters or even years—the business starts to look really good. Just to give you an idea, we make about a nickel every time someone opens an email. We acquire a subscriber for roughly $3, depending on the channel. So if you retain them for six months or longer, the math starts to work in your favor.

From a private equity lens, I saw a compelling model: if you can consistently deliver value in a clear white space, the economics work, the business becomes profitable, and you build something sustainable. That’s how we viewed it going in. Then we had to do the actual work, of course, but from afar, it was clear that these are great businesses to build.

What was the hardest part of going from zero to one?

The hardest part was figuring out what the customer truly wanted, and then getting to scale. That was the trickiest part. The nice thing about this business model is that it’s a flywheel. You build a great product, sell ads against the audience, and then reinvest most of the revenue back into growth. But the flywheel doesn’t start spinning until you reach a certain level of scale.

When you’re small, say a couple thousand subscribers, advertisers don’t care, because you're not big enough to make an impact for them. And you’re not making enough money to cover your expenses or invest meaningfully in growth. It’s a tough phase because you haven’t broken through yet, but you’re doing all the work as if you had.

Once you do reach scale—into the hundreds of thousands of subscribers—everything gets easier. The flywheel kicks in, and you can reinvest profits into acquiring more users and improving the product. It becomes a really elegant business model. But getting from that early stage—1,000 to 100,000 subscribers—is the hardest part by far. That’s the grind.

What are the main levers for finding ‘healthy, wealthy, and wise’ readers?

We're adding about 300,000 new subscribers a month right now, but it definitely wasn’t like that when we started. As the business has compounded over time, our growth engine has evolved. Roughly 25–30% of our growth today is organic, driven by word of mouth, referrals, and people simply telling others. That’s the best kind of growth: it’s free, and it also tends to be the highest quality.

The challenge is that it doesn’t scale as well as Meta or Google, so we balance all three.

We’re also constantly testing new channels—Pinterest, Quora, others—to see what performs. But our big three are organic, Meta, and Google. That’s the engine behind how we find and grow our audience of healthy, wealthy, and wise readers.

What’s driven such high revenue per employee at 1440?

We’ve consistently posted over $1 million in revenue per employee for the past few years, and there are a few reasons behind that. First and foremost, we obsess over the product. If you’re not pouring your heart into it and delivering something truly valuable every single day, you’ll never get anywhere close to those numbers. We have a 65% daily open rate, world-class click rates, and incredibly strong retention—because the entire team is focused on creating something worth people’s time. That’s our foundation.

The second big driver is focus. We say no to a lot. I’ve been surprised by how many media companies chase unprofitable revenue—they have one successful product, then spin out 20 more and dilute their focus. That adds complexity, pulls attention from what’s working, and often leads to thin margins and wasted effort.

Instead, we look at every opportunity and ask: does this really move the needle? Will this generate meaningful profit? If the answer is no, we don’t do it. Even if something might add $200K in EBITDA in year three, it’s not worth chasing if it distracts us from a product that’s already working and has massive upside.

A lot of media companies go from 30 to 300 employees and barely grow revenue. We’ve tried to do the opposite: stay lean, stay disciplined, and double down on what works. That’s what drives the high revenue per employee.

Do you have any other newsletters?

Yes we do, and it’s part of a bigger strategy we’re pursuing. Our core audience of 4.5 million readers is super curious and loves learning across a wide range of topics. Over the years, they’ve told us the same thing again and again: they’ll see something in the news—like CRISPR, the gut microbiome, or Burning Man—and want to learn more, but it’s hard to find reliable, high-quality information. They try Google, and it’s a mess of SEO clickbait. Or they go to social media and get a mix of great content and total nonsense. It’s frustrating, especially for busy professionals like doctors and lawyers who don’t have time to sift through all that.

At the same time, our editorial team was already doing this work, digging up the best resources while researching daily news topics. We'd constantly find incredible videos or explainers from places like MIT that were just buried online. So we decided to build a solution: a new platform called 1440 Topics.

We haven’t nailed the perfect description yet, but the way we think about it is; what if Reddit and Wikipedia had a baby, but everything was human-curated and fact-checked?

In support of Topics, we’ve launched a few focused newsletters—like our business and finance edition, where we explain concepts like IPOs, venture capital, Ethereum, and more. We’re not covering the daily news in those. We’re giving people foundational knowledge. Stuff most people hear about all the time but rarely understand deeply. That’s the goal. Long-term, we want 1440 to be the go-to place anytime someone wants to truly learn about something.

What is 1440 Topics, and why did you create it?

1440 Topics came directly from what our readers were telling us. These are curious, busy people—doctors, lawyers, parents—who want to learn about things they see in the news, like CRISPR or inflation or Burning Man. But when they try to dig deeper, it’s a frustrating experience.

Search engines are cluttered with SEO junk. Social media is hit-or-miss—you might find something useful, but it’s buried in a sea of noise, misinformation, or clickbait. People don’t have time to sift through all that. What they want is context, clarity, and trust. We also saw it happening on our own team. Our editorial staff spends all day researching and often finds amazing resources—like a brilliant MIT video on CRISPR—but they’re buried so deep online no one else can find them.

So we created 1440 Topics. It’s a new product that we describe as “if Reddit and Wikipedia had a baby,” but everything is human-curated and fact-checked. Readers trust us to give them a clean, high-signal summary of the topic—and then send them to the best resources on the internet: the best podcast, video, article, or data visualization. It’s all about helping them choose their own learning adventure without wasting time.

We also launched dedicated newsletters to support this, like one on business and finance. For example, instead of just reporting that a company went public, we explain how IPOs actually work—because most people hear these terms constantly but never really get the foundation.

Ultimately, Topics is about turning 1440 into more than just a daily newsletter. We want it to become the place people go anytime they want to truly understand something.

How would you describe your day-to-day?

My day-to-day is constantly evolving, but at its core, it's about learning. I love learning—and so does our entire team. We're a knowledge company, so continuous learning and sharing is at the heart of everything we do.

What makes the role exciting is that every quarter, every month, every week brings a new challenge. In the early days, it was about going from 78 to 500 subscribers. Then it became: how do we build a growth engine? How do we get our first dollar of revenue? Then it shifted to hiring the smartest people and building a great culture. Now, it’s about transitioning from a newsletter business—which will always be our core—to a full media platform. That’s a completely different kind of learning curve.

So for me, it's really about two things: staying in a constant learning mindset and making sure I’m focused on the highest-ROI initiatives for the company. I also want the whole team thinking that way. That means saying no to anything that doesn’t drive long-term value. No unnecessary meetings. No fluff. Even as we've grown from 5 to 22 employees, the complexity has increased exponentially—not linearly. So we work hard to keep communication clear, make sure everyone’s aligned, and avoid slipping into the bureaucracy you see at big companies.

We’ve actually taken a lot of inspiration from leaders like Brian Chesky at Airbnb and Jensen Huang at Nvidia—people who’ve built flat, focused, high-performance teams. That’s the kind of culture we’re working to maintain.

What does your team look like, and who do you directly manage?

We’re a very flat organization—we talk to each other constantly, and there’s very little hierarchy. Right now, we’re a team of 22, and the majority are on the editorial side, which makes sense since we’re a content company. Editorial is split between the core newsletter team and the new Topics team. On the Topics side, for example, we have three writers focused on business and finance, science and tech, and society and culture. That’s the lion’s share of the company.

Beyond that, we have small but mighty teams in growth, product, revenue, and HR. I still serve as our CFO, which might sound unusual, but I think it’s really important for me to stay close to the numbers. It lets me move quickly and make smart decisions without waiting on a finance layer. We also hold a company-wide Monday meeting to keep everyone in sync. The goal is cross-functional awareness—so our product person knows what the marketing team is learning from the ads, and that intel flows back into the product.

Culturally, everyone at 1440 is curious and wants to learn—not just about their own role, but about how the business works. We try to share as much context as possible, from unit economics to growth metrics. That investment in transparency helps everyone grow—and it helps the company run better.

How do you think about leadership?

I’m still figuring it out every day. Leadership’s not easy, and I try to learn from people who’ve done it better than me. One of the biggest influences was my time in private equity. I saw firsthand what bad leadership looked like, CEOs who hired people less capable than them, created a culture of fear, and ultimately slowed everything down. But I also saw what great leadership looked like—someone comes in, empowers the team, and suddenly everything changes, even though most of the staff stays the same. That contrast really stuck with me.

Another big influence is how much I study other founders. It’s both a personal passion and something we do at 1440; learn, synthesize, and share. The more I read and listen to these people across history, the more I realize they’re all saying variations of the same things. We’ve built our own internal principles around that, things that guide how we work and make decisions. A lot of it boils down to long-term thinking, serving the customer well, and focusing on what really matters.

We’ve made hard calls—like turning down early ad revenue that didn’t align with our values—because we knew we were building something trust-based. That kind of decision only happens when you have clarity as a leader. And profitability, for us, isn’t just about the bottom line—it’s about independence and control. So yeah, I’d say good leadership is about empowering your team, staying focused, and holding a long-term view—while still being willing to get into the weeds and do the work.

Do you have any go-to interview questions when hiring?

It’s less about one magic question and more about the process we use. Back in private equity, we used to do something called a mock board interview, especially for executive hires. We'd share a ton of real company info under NDA and ask candidates to walk us through their 90-day plan, as if they were presenting to a board. It’s interactive and reveals how they think, how deep their experience goes, and how they respond when challenged.

At 1440, we’ve adapted that for different roles. If it's a growth role, we might ask for a 90-day growth plan. If it’s product, we want to see how someone would prioritize and execute. The goal is to get a few layers deeper than surface-level strategy talk and see how someone actually works.

Beyond that, we look for three things: first, a genuine love for the work—not every part of it, but the core of what they’ll be doing. Second, intellectual horsepower. I always tell the team, if someone doesn’t seem brilliant or sharp when you talk to them, just move on. And third, culture fit. You want to work with people you respect, enjoy, and who want similar things out of life and work. When someone checks all three of those boxes, we’ve found it usually works out really well.

💡 Hiring? My startup, Athyna, can help. Our current specialty is in AI and ML engineers. Hard to find, but we can find them!

Do you use any frameworks or cadences when setting goals?

We set quarterly goals, but we keep them pretty loose. We don’t obsess over detailed financial models or hyper-specific forecasts, most of that ends up being wrong anyway. Instead, we focus on directional themes and clear ownership.

For example, our head of growth has a budget and knows her job is to acquire high-quality subscribers at the lowest possible cost. It’s not about hitting an exact number like ‘300,000 subs this month,’ it’s about doing the best possible work within the economics we know work.

Sales is the same. We know our targets, but it’s more about effort and outcomes than hitting a specific number every week. Everyone understands how their work fits into the broader flywheel and where the real levers are. We do track OKRs weekly to make sure things are moving in the right direction, but the culture is less about rigid tracking and more about performance and alignment. We keep the focus on doing excellent work, communicating clearly, and compounding small wins. That’s how we’ve grown. And we’ve found it’s a lot more effective than over-planning.

What is your North Star metric?

Right now, it’s quality subscribers; people who consistently open and engage with our content. That number drives everything else: retention, revenue, and ultimately how much we can reinvest in growth.

Looking ahead, as we expand beyond the newsletter into our Topics platform, we’re starting to think in terms of minutes spent learning. Last year, people spent around 4 billion minutes learning with 1440, and we want to grow that. It’s a great signal, not just for engagement, but for impact. So today it’s engaged subscribers, but long-term, it’s total learning time across our ecosystem.

What’s a quality subscriber to you?

A quality subscriber is someone who consistently opens and engages with our emails—so it’s a combination of open rate, click rate, and overall retention. What’s wild is how much that varies by acquisition channel. For example, someone who comes through a newsletter ad might be 2–5x more valuable than someone who comes through Facebook. Same month, same cohort, completely different engagement levels.

But of course, the better subscribers are also more expensive. So we’re constantly doing the math—balancing cost per acquisition with long-term value—to find the best mix. That’s how we define and optimize for quality.

What’s the biggest lesson you’ve learned building 1440?

That it’s way harder than you think. Starting a company sounds exciting—and it is—but the reality is, it’s like getting punched in the face metaphorically, every day. One moment you feel on top of the world, and ten minutes later something goes wrong and it feels like everything’s falling apart. It takes way longer than you expect, and it’s incredibly emotional. So the biggest lesson is: you have to really love what you're building. If you don’t, it’s just too easy to give up when things get hard, and they will.

I always point to my co-founder, Drew. He had a full-time job working for the U.S. government, a two-year-old daughter at home, and he was waking up at 4 a.m. every day to ship our newsletter when we only had 1,000 subscribers. That’s not something you do unless you love the mission.

So yeah, the lesson is: you need grit, and you need to care deeply. Otherwise, you probably won’t make it through the hard parts.

And that’s it! You can also connect with Tim over on LinkedIn and don’t forget to check out 1440's website.

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