Hi Tim,

When I left full-time startup exec work in early 2022 to start moonwater, I was pumped but at the same time deflated.

I had recently taken a new Chief Growth Officer role with a startup flush with cash. A few weeks in though, I knew it wouldn’t last. The culture was toxic, and I couldn’t do my best work.

I knew starting moonwater was my way out. While I was hell-bent on working with high growth startups, I had no plans to compromise on culture.

So I sold for a few weeks, booked a full book of biz, and bought myself 6 months of runway to keep figuring it out.

I also got incredibly lucky.

My second client happened to be one of the most impressive startups in the country. They were high growth, one-of-a-kind, and 100% people-first.

The company was 1440 - an email newsletter for unbiased news. They have 3M+ readers, 8-figure rev, and over $1M in rev per employee (no, that’s no typo).

Tim Huelskamp, their co-founder & CEO, is one of my favorite people in startups. I’m shocked more people aren’t talking about their playbook to craft, validate, and scale a wonderful product.

While I no longer work with 1440, Tim and I talk often, and I was so pumped to share his story and top lessons.

Without further due, here’s Tim’s story and my top 10 takeaways from last time we caught up:

#1.

Tim’s always been entrepreneurial. He was doing lemonade stands early, and in high school he was burning CDs for extra cash. Then, post-college, he spent a decade in i-banking, PE, and even angel investing. Being around interesting businesses constantly, he knew he’d take his own shot soon enough.

#2.

Eventually Tim got laid off, but they gave him a great package. Rather than sulk about it, he felt like he fell into an incredible spot. His generous severance meant he could now “get paid” to start a company. So he took the leap.

I love meeting people with perspective like Tim because attitude is almost everything. When life gets hard (and startups always do), perspective is powerful. It can save you from plenty of darkness.

#3.

While 1440 has been a wild success, Tim started a travel startup first. It failed though. His biggest lessons?

Finding product-market fit AND product-channel fit both matter.

It’s one thing “to make something people want” (i.e. product-market fit), but if the unit-economics don’t work AND you don’t have a clear path to finding customers at scale (product-channel fit), you don’t have a viable business.

Everyone in startups talks about the importance of product-market fit, but I hear a lot less talk about product-channel fit. I’m glad Tim brought it up.

#4.

I asked Tim if he thought about going back to a cushy finance gig after his first startup failed. He said he probably would have if it wasn’t for his wife.

It reminded me of the importance of having people in your corner when you’re doing hard things. It’s a heck of a lot easier to suck it up and keep going when you have people who believe in you at your side.

Cool spouses aside, Tim felt like between his years in finance and his failed startup, he now had an unfair advantage to build something new. So he decided to give it another shot.

Tim and his wonderful co-founder Drew launched 1440 in August 2017.

#5.

In 2023, 1440 was in the top 1.6% of Inc 5000’s Fastest Growing Companies. I asked Tim what he thought about the accolade, and I loved his response:

“The external validation is wonderful. We’re very grateful for it, but it’s not what drives us. When I was in PE, I saw a lot of companies with press and plenty of sizzle go belly up. While I wish we started trying to get recognition a bit earlier, I’m proud we’ve focused mostly on crafting a wonderful product and delighting customers.”

So true. I’ve seen a lot of companies get wrapped up in their own hype or that of competitors. Oftentimes though, it’s a distraction. None of it matters unless you build a great product and solve a deep problem for enough people.

#6.

When I asked Tim about raising money for 1440, he said he talked to investors early on, but no one would fund them. Why? Because it didn’t feel “venture scale” to them. This was a huge silver lining, though. Today, 1440 is largely employee-owned, and in total control over their destiny.

Nothing against taking big capital and VC. I’ve worked with plenty of companies who do. But like most things, there’s clear pros and cons, and you need to know what you’re signing up for. In the last 2 years I’ve worked with more bootstrapped businesses, and it’s hard to argue the appeal. I.e., You can play the long game, grow slower, avoid distractions, and do what you want.

#7.

Tim’s one of the most people-first CEOs out there. 1440 hires slow, they hire the best, and they pay above market rate. They also encourage great work-life balance and get the heck out of their employees' way. I asked Tim how 1440 became so people-first, and he told me about the #1 thing he learned in PE:

“People and team are the #1 thing to win in business. When we used to buy companies in PE, I learned A players hire A+ players while B players hire C players. Because they’re afraid to hire people smarter than them. We’re trying to build a 50-year company with 1440. Hiring great people and treating them incredibly is the highest ROI capital by orders of magnitude.”

I loved Tim’s take here. Too many companies think taking incredible care of your team is just a way to stay competitive with FAANG (Meta/formerly Facebook, Apple, Amazon, Netflix, and Alphabet/Google). But the business benefits of truly giving a damn about your people are profound.

#8.

My favorite 1440 metric is they’re doing $1M+ in revenue per employee. Very few companies ever get here. I asked Tim for a few of the key things that helped them operate at such a high level. My favorite 3 he mentioned:

• Obsessively serving and delighting the customer.
• Taking the longest view in the room.
• Making sure the work is rewarding.

Re “taking the longest view” - Tim mentioned this amazing Warren Buffett quote I’ll now never forget:

“When Buffett buys companies, he tells the team to run it like you’re the sole owner, it’s the only asset you hold, and you can’t sell it for 50-years.”

Being profitable means Tim and the team can play the long-game. Turns out this is a massive differentiator integral in helping them get so far ahead.

#9.

According to Tim, most people know 3/4 top responsibilities of a great CEO:

• Hire an A-team.
• Set a great strategy and execute.
• Make more than you spend.

But he said there’s one thing many overlook:

“You have to delight the customer. Product, product, product. We’re an 8-figure company, and customer support is still my Inbox. A lot of companies don’t give customers a great opportunity to provide feedback. Even fewer then consider it and follow through. We ask customers for this 6x/week in our daily sends, and it’s turned into an incredible unfair advantage for us.”

#10.

Tim’s final parting advice was two-fold:

“First, if the customer and product isn’t the heart of everything you do, nothing else matters. I run into a lot of people worrying about growth and monetization too soon. Second, building a successful company takes way longer than most people think. I had advantages compared to many founders given my experience and financial situation, and it was still insanely hard. Grit is so key in the early days, but even as you start booking wins.”

You can get in touch with Tim here. If you want to get a taste of what an incredible product looks like, check out 1440.

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