Startup Stories - Mixergy

Episode #2274: "1440: $20+mil / year newsletter"

Date: April 29, 2025
Host: Andrew Warner
Guest: Tim Huelskamp, Co-Founder of 1440

Episode Overview

In this episode, Andrew Warner interviews Tim Huelskamp, co-founder of the fast-growing, fact-focused daily newsletter 1440. The discussion centers on how 1440 scaled to over $20M in annual revenue while maintaining profitability, a lean team, and an intellectually curious, non-niche approach in a mature, competitive newsletter landscape. Tim shares insights from his background in private equity, hard-won lessons from a failed startup, and the dynamic strategies behind 1440’s explosive growth—all while emphasizing sustainable, bootstrapped business building.

1. 1440’s Business Snapshot and Revenue Model

• Company Profile & Revenue

  • Over $1M in revenue per employee, with 22 employees—a $20M+ annual top line
    • [01:23, Tim:] "We do over a million in revenue per employee and we have 22 employees... I'll let the readers do the math."
  • Profitable, with several million dollars in profit
    • [01:44, Tim:] "Yep, very profitable."
  • No traditional VC funding—only an early $500K revenue-based loan with a royalty return structure
    • [01:53–03:51]: Tim explains the funding instrument: 5% of revenue paid back until 3x return, plus a small equity kicker.

• Unique Economics of Newsletters

  • Daily engagement means revenue from every engaged subscriber, every day:
    • [30:36, Tim:] "We make about a nickel every time someone opens our email... call it 70 cents a month a user. We're acquiring users for like $2 or $3... so it's like, you know, that five to six month payback period and then after that, it's just all revenue that we can just reinvest back into growth."

2. Key Growth Strategies and Philosophy

Why Go Broad in a “Niche is Riches” World?

• Unconventional Market Positioning

  • Advisors said they should go niche, but Tim & co-founder Drew were driven by their own intellectual curiosity—craving breadth over depth.
  • Thesis: Serve the "inch deep, mile wide" knowledge needs of busy, educated professionals from all fields—like what the NYT’s front page used to do.
    • [06:30, Tim:] "I think it got over niche and then like a white space opened up to be like, someone can come in and fill that... the inch deep, mile wide provider for the intellectually curious people. I'm like, that's who we're filling."
  • Core market: College and grad school-educated professionals frustrated by polarization and overload who want fact-forward news without partisan undertones.
    • [06:30, Tim:] "A third of them have a graduate degree... our audience is roughly a third Democrat, a third Republican, and a third Independent."

• Rapid, Feedback-Driven Iteration

  • 1440 launched by emailing first draft to 78 friends & family (Mailchimp; [18:39, Tim]).
  • Looked for early signs of strong product-market fit: 40%+ open rate & 5% weekly organic growth.
    • [18:47, Tim:] "If we don't have a 40% open rate and a 5% weekly organic growth rate... we shouldn't spend time on this project. ...But we had like a 60% open rate."
  • Iterated quickly based on feedback, especially on format—stripped out images as users wanted text-only for efficient skimming.
    • [21:16, Tim:] "Our newsletter is all words... if you break down what we do really well, we curate 50 links across the Internet... [users said] 'the pictures don't help me put knowledge efficiently in my brain. Get rid of them.'"

3. From Failure to Product-Market Fit: What Tim Learned

Story of “When In Rome” (Failed Startup)

• Tim explains how private equity experience distorted his expectations around startup growth channels and unit economics ([10:13–14:38]).
• Main lesson: You need product-market fit, but also profitable, scalable unit economics. When In Rome had high acquisition costs ($200) and low LTV ($12) and couldn't scale.
  • [13:40, Tim:] "Startups are three things at their core. It's the search for product market fit... The second one... can you get repeatable, profitable, scalable growth... and then scale."

Applying Lessons to 1440

• Saw beautiful unit economics in email newsletters: recurring engagement, low acquisition cost, high revenue per user.
  • [15:53, Tim:] "If you can find white space and delight a user... it's all about retention and having them come back to you, there's a big business in here."
• Inspired by Sam Parr (The Hustle), Morning Brew, The Skimm, but with bigger TAM by going broad.

4. Operations, Team, and Long-Term Focus

Lean Team, Reluctance to Outsource

• For years, co-founder Drew wrote daily newsletters solo, waking up at 4am before his day job due to early resource constraints.
  • [26:04, Tim:] "Drew had a full time job and was waking up at 4 in the morning to finish our newsletter and ship it out before he went to his work... talk about grit."
• Hired first full-time editor only once economics allowed (Sony from Bloomberg) and prioritized products where the founding team ensured quality.
• Reluctant to hire average/cheap writers to protect product experience.

Profitable Bootstrapping, Absolute Focus

• Tim openly favors using profits to grow and says bootstrapping means "you control your own destiny."

  • [41:16, Tim:] "You control your own destiny... we can do whatever the hell we want. It's such a powerful move."

• Refused to diversify into side newsletters despite pressure; focus on one product enables world-class editorial, retention, and operational efficiency.

  • [39:49, Tim:] "[Mars exec:] 'Why do you have 40 SKUs?'... With us, it's like, why are we thinking about [spinouts]?... do one thing, do it really well. Keep it simple."

• Commitment to people: "Lost one employee in four years... no layoffs, ever. Million revenue per employee, keep it lean and mean."

5. Subscriber Growth and Retention Mechanics

• User Acquisition: Started with founder-funded Facebook ads, then shifted to agency partners. Early cost per subscriber as low as ~$1, today $2–$3 ([28:32]).
• Retention Cohorts: About 15% of signups never open, but those who do settle at ~50% engagement long-term.
  • [29:00, Tim:] "You can see it in our retention curves... even our cohorts from like 2018, something like 40% of them are still around."
• Economics: 25 emails/month, 65% open rate, average 15 opens/month per engaged user, earning ~$0.70/user/month.
• Current Growth: Adding ~300,000 subscribers/month, retaining ~150,000 ([28:43–31:27]).

6. Comparative Analysis and Industry Lessons

• Comparing with Inside.com (Jason Calacanis)

  • Jason’s "niche within niches" approach—from outside, Tim sees product quality and lack of passion as the flaw, not the business logic.
    • [32:59, Tim:] “I think the strategy was brilliant... I think the problem was product quality... you have to pour your heart and soul into the product.”

• Why Newsletters Are "Beautiful Businesses"

  • High engagement habits, predictable recurring revenue, scalable digital costs, and extendable lifetime value.
    • [36:46, Tim:] “I agree... That's one of the reasons we really liked it... If you can deliver, these things are beautiful businesses.”

7. New Bets: "Topics" (Human-Curated Knowledge Platform)

• What’s Next for 1440?
  • Launching "Topics" (name might change): Think Reddit meets Wikipedia meets Pinterest, focused on high-quality, human-curated resources for learning about any subject.
    • [42:54, Tim:] "We're trying to build... if Reddit, Wikipedia and Pinterest had a baby for knowledge..."
  • Aimed at people frustrated with SEO spam, clickbait, or impersonal AI-generated answers
    • [46:25, Tim:] "We're building this ecosystem... the best place in the world to learn about a topic is our website."
  • Human editors, using AI as a tool, not a replacement:
    • [48:28, Tim:] "Our human editors are using AI tools... but at the end of the day, it's human curated. We think there's a lot of beauty in that..."

8. Memorable Quotes & Moments

• On Funding and Unit Economics:

  • [03:51, Tim:] “It's not like a piece of debt where you have a guaranteed payment. It was based on as a percentage of your revenue, which is really nice too.”

• On Focus:

  • [39:49, Tim:] “Why are we thinking about this? It doesn’t matter. Why don’t we take all that energy and focus on something bigger?”
  • [39:49, Tim:] “Do one thing. Do it really well. Keep it simple. Less is more. The power of saying no. Focus, focus, focus. When you do that, magic happens.”

• On Going Broad vs. Niche:

  • [06:30, Tim:] “I think it got over niche and then like a white space opened up... the inch deep, mile wide provider for the intellectually curious people. That's who we're filling.”

• On Bootstrapping and Autonomy:

  • [41:16, Tim:] “You control your own destiny... We can do whatever the hell we want. It's such a powerful move.”

• On Not Outsourcing/Early Grit:

  • [26:04, Tim:] “Drew was waking up at 4 in the morning to finish our newsletter and ship it out before he went to his work... talk about grit and believing in your mission.”

• On the Name 1440:

  • [49:05, Tim:] "It's the year the printing press was invented, when knowledge was exploded to the masses... also the number of minutes in a day."

9. Timestamps for Key Segments

• Revenue & Team Structure: [01:23–03:51]
• Funding Approach: [01:53–03:51]
• Why Go Broad in Newsletters: [04:39–07:46]
• Lessons from a Failed Startup: [10:13–14:38]
• Newsletter Economics vs. Other Online Models: [14:38–18:15], [36:04–36:46]
• Early User Feedback & Iteration: [18:15–21:48]
• Operations & Team Growth: [23:31–28:17]
• Subscriber Growth & Retention: [28:43–31:27]
• Industry Comparisons & Case Analysis: [31:27–34:51]
• Business Analysis & Strategic Focus: [34:51–39:49]
• Second Product/New Platform: [42:54–48:59]
• Origin of Name '1440': [49:05]

10. Takeaways & Lessons for Entrepreneurs

• Product-market fit and good unit economics are critical before scaling.
• Bootstrapping + focus enables tremendous autonomy and resilience.
• A “mile-wide” newsletter can fill a massive market gap—sometimes, conventional wisdom to “go niche” is wrong.
• Customer experience and product quality are moats. Passion and consistency matter.
• Don’t diversify too soon; operational excellence and customer love require focus.
• New opportunities exist even in “old” or “boring” digital business models, if executed at scale and with clarity.

End of Summary