Daily Drop started with a mission: help people travel more while spending less.

Created by Nate Buchanan (of the YouTube channel Kara and Nate), and run by Content Director Benji Stawski, the newsletter was born out of years of full-time travel.

The team kept hearing the same question over and over again: “How do you afford to travel so much?”

The answer? Points and miles — but simplified.

So, they built Daily Drop, a short, punchy newsletter that demystifies travel hacking and makes it accessible. Each email takes under five minutes to read but is packed with deals, strategies, and how-tos for traveling smarter.

Fast forward to today, and Daily Drop has:

• Over 1.5 million subscribers

• A seven-figure business

• A lean team operating a media powerhouse

• And the infrastructure to keep scaling, thanks to beehiiv

Table of Contents

• Day One: 50,000 Subscribers With Zero Deliverability Issues

• Early Growth: From Organic Lift to Paid Boosters

• Switching to beehiiv: The Quest for a Scalable Platform

• Favorite Features: Automations and Segmentation at Scale

• Lean Team, Big Results: Operating a Media Company

• Earning Done Right: Value-Driven Sponsors and Affiliate Wins

• Built by Newsletter People: Fast Features and Stellar Support

• Advice for Aspiring Newsletter Creators

• Final Thoughts: Start Where You Are. Grow With beehiiv.

Day One: 50,000 Subscribers With Zero Deliverability Issues

Most creators fight for their first 100 subscribers. Daily Drop launched with over 50,000.

How?

They had an unfair advantage: an existing user base from FareDrop (now Daily Drop Pro), their flight deals platform, and a huge audience from Kara and Nate’s YouTube and Instagram presence.

“We had a bit of an unfair advantage and sent our first newsletter to over 50,000 people without deliverability issues,” Benji says.

This gave them a massive head start — but instead of coasting on it, the team doubled down on content quality and consistency to turn that initial boost into long-term growth.

Early Growth: From Organic Lift to Paid Boosters

In the beginning, growth was largely organic. Daily Drop’s initial subscribers came from cross-promotion: mentions in Kara and Nate’s YouTube videos, links in FareDrop communications, and shout-outs on social media. This organic strategy gave Daily Drop a solid foundation of loyal readers who were already interested in travel hacking.

Once that audience was tapped out, Daily Drop turned to paid ads, and it changed everything.

“Most of our new subscriber growth now comes from paid ads,” says Benji.

They used messaging like:

“Learn to travel for nearly free – our daily email shows you how.”

Targeted campaigns on Facebook and Instagram drove tens of thousands of new sign-ups. And thanks to solid content and onboarding, these new subscribers stuck around.

The team also focused on high-quality content from day one – delivering real value (like timely points deals and beginner-friendly guides) to earn trust and word-of-mouth referrals. As a result, open rates were strong early on, and the subscriber count kept climbing as readers told their friends about the newsletter.

The key? Great targeting + great content + great infrastructure = scalable growth.

Switching to beehiiv: The Quest for a Scalable Platform

One of the pivotal decisions in Daily Drop’s journey was choosing the right platform to host and send the newsletter. In the very early days, the team used an Ecommerce oriented email tool (a holdover from the FareDrop product) to send Daily Drop. It handled basic email sends, but it wasn’t built with newsletters in mind. 

After only a few months, the team knew they needed a more robust, growth-focused platform. That’s when beehiiv came onto their radar. Built by former newsletter operators, beehiiv promised an all-in-one solution tailored for exactly what Daily Drop was trying to do. The team was drawn by several key factors:

• Simplicity and Speed: beehiiv’s interface was clean and intuitive, which meant the Daily Drop crew could move fast. With Beehiiv, creating and scheduling emails has become easier and faster than their old setup. The platform’s performance was also evident immediately – no more laggy send times or clunky workarounds.

• Deliverability and Scale: As a newsletter-native platform, beehiiv came with enterprise-grade infrastructure and high deliverability out of the box. The Daily Drop team saw this as crucial for hitting millions of inboxes reliably.

• Advanced Analytics: Moving to beehiiv also unlocked a treasure trove of analytics and audience insights. Suddenly, the team could easily track open rates, click-through rates, and engagement trends across various segments of their audience. These accurate, real-time metrics let Daily Drop gauge what content resonated most and which subject lines were crushing it – informing their editorial strategy with data.

• Flexible Earning Tools: Given Daily Drop’s plans to earn via sponsors and affiliates, beehiiv’s support for ad integrations and sponsorship placement was a plus. It wasn’t just an email tool; it was a platform to grow a newsletter business. 

Convinced by these benefits, Daily Drop made the switch to beehiiv. The migration was smooth – the team moved their entire subscriber list over and set up their custom domain without a hitch. Almost immediately, they noticed improvements. 

The deliverability uptick was clear from day one, with more emails hitting primary inboxes and fewer getting caught in filters. And with beehiiv’s analytics dashboard, Benji could see their open rates jump and consistently stay higher than on the old platform.

Favorite Features: Automations and Segmentation at Scale

One beehiiv feature Daily Drop quickly fell in love with was Automations. 

With a rapidly growing list, manually onboarding and educating new subscribers was impossible – but it’s crucial to get newcomers up to speed on points and miles basics (so they stick around). 

beehiiv’s automation tool allowed the team to set up a welcome email sequence that triggers for every new subscriber. As soon as someone joins, they automatically receive a friendly welcome message and a series of onboarding emails spread over their first week. 

These emails introduce the Daily Drop ethos, highlight popular past tips, and explain key concepts (like “Miles & Points 101”) to bring readers of all experience levels up to speed. This kind of scaled onboarding, which would be daunting to do manually, runs in the background 24/7 thanks to beehiiv – ensuring new subscribers feel at home from day one.

Even more game-changing has been beehiiv’s subscriber segmentation features. Daily Drop’s audience isn’t monolithic; it ranges from total beginners to seasoned travel hackers, and from credit card enthusiasts to deal-focused flyers. 

beehiiv makes it easy to slice and dice the audience based on behavior and interests. The team can tag and group subscribers by metrics like engagement level (e.g., highly active readers vs. occasional openers) or by their interests indicated through link clicks (e.g., who clicks on credit card offers versus who clicks on flight deal alerts).

They’ve used this data to tailor content more effectively. For example, if a segment of readers consistently clicks on beginner guides, the team can send them a targeted email with “best of” beginner tips, or promote the free Miles & Points 101 course to that group. Meanwhile, power users might get more advanced content or exclusive offers. 

This smart use of segmentation means each reader gets more of what they’re interested in, which in turn boosts engagement. Open rates have climbed on these tailored sends, and affiliate conversion rates have improved because the right offers are reaching the most receptive subset of readers. 

As Benji puts it, “Being able to segment our subscriber base and see who’s interested in what – so we can gear content towards them – has been huge.”

Lean Team, Big Results: Operating a Media Company

One of the most striking things about Daily Drop is how such a small team can service such a massive audience. We often imagine a newsletter with over 1.5 million readers would need an army of writers, marketers, and IT staff. Yet Daily Drop runs incredibly lean. 

Apart from Benji overseeing content, the team includes a handful of writers and editors, a deals expert, a marketing lead, and a developer – a fraction of the headcount a traditional media outlet might have for an audience this size. How do they pull it off?

“Our team can focus on writing great content instead of worrying about tech overhead,” Benji explains.

With so many functions rolled into one platform, beehiiv saves the Daily Drop team from wasting time juggling a dozen tools or patching together tech. Email creation, sending, web hosting for newsletter content, subscriber management, analytics, and even earning options are all built into beehiiv. This means fewer logistical headaches and subscriptions to manage, and more time to focus on what matters – creating great content and forging partnerships.

Since moving to beehiiv, Daily Drop has seen improved email deliverability and consistently strong open rates (often well above industry benchmarks for media newsletters). With more readers actually seeing and opening the emails, the newsletter’s impact grew overnight. 

Higher open rates combined with better targeting have led to surging affiliate revenue – when Daily Drop recommends a travel credit card or an airfare deal, readers are more likely to click and convert, because they trust the content and it’s reaching the right people. This boost in affiliate conversions has meaningfully improved the newsletter’s revenue without sacrificing the reader experience or authenticity.

Daily Drop can show potential advertisers granular data – like how engaged the audience is, or how a campaign performed with a specific segment – giving sponsors confidence that their message is reaching a prime audience. This has helped Daily Drop secure high-quality sponsorship deals, increasing earnings from the newsletter in a way that aligns with their readers’ interests.

Earning Done Right: Value-Driven Sponsors and Affiliate Wins

From the outset, the Daily Drop team knew they wanted to earn in a reader-friendly way. Rather than plastering the newsletter with random ads, they pursued value-aligned sponsorships and affiliate partnerships that would genuinely benefit their subscribers. 

“Our rule is simple,” Benji says. “If it’s not something we’d personally use or recommend to our travel-loving friends, it doesn’t go in the newsletter.” With this philosophy, Daily Drop earns through trust and relevance.

Affiliate links (particularly for travel credit cards and booking platforms) are a natural fit. When the newsletter mentions a top credit card that comes with a huge points bonus, it uses referral links that earn a commission if readers apply and are approved.

Because Daily Drop’s content is already focused on helping readers get those exact kind of deals, the affiliate promotions feel organic – essentially extensions of the editorial mission. And thanks to beehiiv’s targeting capabilities, the team can send the most relevant offers to the subscribers who are likely to benefit. 

For instance, if a subset of readers frequently clicks on hotel deals, an affiliate offer for a hotel credit card or a booking site can be directed their way. This smart targeting has led to higher conversion rates, meaning more readers actually take action on the deals, and Daily Drop earns more affiliate revenue without increasing send volume. 

It’s a win-win: readers score travel deals or rewards, and the newsletter generates income to keep content free for everyone.

On the sponsorship side, Daily Drop has carefully chosen sponsors that fit the travel theme and bring value.

Past sponsors have included luggage brands, travel insurance companies, and reward program promos – all things a points-savvy traveler would care about. beehiiv makes it easy to integrate sponsor content or dedicated ad sections within the newsletter template, so the team can feature a sponsor’s message in a visually appealing way without disrupting the overall look and feel.

The newsletter’s revenue from affiliates and sponsors has grown in step with its audience. At the same time, beehiiv’s efficient tooling saves the team significant time (which, as any small operation knows, is money). 

Benji estimates that automation alone saves hours of manual work each week, and the reliable deliverability means they’re not leaving money on the table due to emails going unseen. In short, beehiiv helped Daily Drop turn a massive subscriber base into a sustainable business, all while keeping readers happy with relevant, high-quality content.

Built by Newsletter People: Fast Features and Stellar Support

Perhaps the most pleasant surprise for the Daily Drop team has been beehiiv’s pace of innovation and customer support. 

“Coming from other platforms, we were used to waiting ages for feature updates or never getting a response to our requests,” Benji notes. 

beehiiv turned out to be a completely different experience. The platform is evolving rapidly, with new features and improvements rolling out seemingly every other week. 

Case in point: when Daily Drop wanted more control over their referral program and deeper audience segmentation, beehiiv’s team was already on it – delivering enhancements that addressed those needs almost immediately. This agility showed the Daily Drop crew that beehiiv isn’t a static tool; it’s a growing platform that’s always adding creator-friendly features.

“The platform feels like it was built by people who’ve actually run newsletters,” Benji says, highlighting perhaps beehiiv’s biggest differentiator.

Knowing that beehiiv’s infrastructure and team could keep up with Daily Drop’s ambitions gave Benji confidence to push the envelope – like scaling to daily sends, trying new content formats, and investing in ad campaigns – without worrying that the platform might become a bottleneck. 

In fact, beehiiv’s reliability and innovation have become an invisible backbone of Daily Drop’s operations, allowing the team to focus on strategy and content rather than tech troubleshooting.

Advice for Aspiring Newsletter Creators

Daily Drop’s journey offers a treasure trove of lessons for other newsletter creators. Whether you’re just starting out or looking to scale your existing newsletter, here are some words of wisdom from Benji Stawski and the Daily Drop experience:

• Start Small and Just Start: “Don’t wait for everything to be perfect,” Benji advises. Even if you have a tiny audience, begin delivering value to them. Those first 100 or 1,000 readers are the hardest to get – but they’re also your most passionate fans who will kickstart word-of-mouth. Use whatever advantages you have (an existing social following, friends and family, etc.) to seed your initial list, but the key is to start. You can always refine and expand later; you can’t grow something that doesn’t exist.

• Stay Consistent: One of Daily Drop’s non-negotiables was consistency – they send the newsletter 6 days a week, rain or shine. Consistency builds trust with your audience; readers come to rely on you as part of their routine. It also forces you to keep improving your process. 

  “Sending daily taught us so much about what our readers want, just by sheer repetition,” says Benji. Whether your cadence is daily, weekly, or biweekly, stick to it religiously. Over time, that consistency is what turns a newsletter from an email into a habit for your subscribers.

• Focus on Content First: Fancy growth hacks and earning strategies mean nothing if the content doesn’t deliver. Daily Drop’s growth ultimately stems from valuable content that people want to read and share. 

  Invest in understanding your niche and audience. In Daily Drop’s case, that meant truly simplifying complex info (like credit card fine print) into fun, quick tips. Whatever your topic, aim to be the best or most unique source of insight on it. High-quality content is your strongest growth engine – it keeps readers opening emails and encourages them to refer others.

• Evolve and Experiment: The newsletter landscape changes, and so will your audience’s preferences. Don’t be afraid to tweak your format, try new segments, or adjust your tone as you learn what resonates. 

  Daily Drop, for example, added new features like a Facebook community, a YouTube channel, and a podcast over time – expanding beyond just the email while keeping the core newsletter strong. Within the emails, they’ve experimented with memes, GIFs, subject line styles, etc., to keep things fresh. Some experiments will flop, and that’s okay. The key is to listen to feedback and data (open rates, clicks, replies) and iterate. beehiiv’s built-in A/B testing and analytics make it easier to test these small changes and measure impact.

Final Thoughts: Start Where You Are. Grow With beehiiv.

At the end of the day, Daily Drop’s trajectory shows that any newsletter can achieve remarkable growth with the right mix of great content, smart growth tactics, and the proper tools. As Benji and team demonstrated, you don’t need a huge staff or endless resources – a focus on your readers’ needs and a platform like beehiiv that scales with you can take you a very long way.

Daily Drop’s rise proves one thing:

You don’t need a massive team, VC money, or years of experience to build a media business.

You need:

That’s what beehiiv offers.

Whether you're just starting or ready to scale, beehiiv is the platform powering today’s fastest-growing newsletters — like Daily Drop.

👉 Sign up for beehiiv and start building something incredible today.