How Jon C. Phillips Builds Profitable Email Newsletters That Last

Jon C. Phillips is a longtime internet builder who has experience with blogging, SaaS, adtech, and, most notably, email newsletters. Jon got his start in online business two decades ago by launching and selling blogs. After discovering a love for photography, Jon founded Contrastly, which grew into a six-figure business powered largely by an engaged email list of more than 100,000 subscribers.

That experience shaped Jon’s conviction that email is one of the most durable and valuable assets an entrepreneur can build. Today, he runs daily newsletters like DailyPhotoTips and TheDailyPreset, and he also recently wrote and launched Email Growth Guide.

In this conversation, Jon breaks down why newsletters remain such a powerful opportunity for entrepreneurs, what most people misunderstand about email marketing, and why owning an audience matters more than ever. He shares practical lessons from years of consistency, honest takes on growth and monetization, and clear advice for founders starting from zero who want to build something that compounds over time.

Please tell us about your background and how you got started with online business.

I got started back in 2005 when I installed WordPress on a server for the first time and started blogging. I was very active in the design and dev community back then, still am, and launched and sold multiple blogs in the design/dev and business/freelancing niches over the years.

Then I discovered photography, which changed everything. I launched Contrastly in 2012 as a photography education platform.

Over 10 years, I grew it to more than 100,000 email subscribers and built a business that was generating over $250,000 per year at its peak. The email list was the foundation of everything. It drove product sales, affiliate revenue, and sponsorships. When I eventually sold Contrastly, the list was a huge part of the valuation.

That experience taught me that an engaged email audience is one of the most valuable assets you can build.

After selling Contrastly, my co-founder and I launched DailyPhotoTips in 2019 and TheDailyPreset in 2023. Both are daily newsletters serving the photography community. I still work on Contrastly here and there, even after selling it, because I genuinely love that audience.

Outside of newsletters, I spent 15 years working in adtech, building advertising systems, analytics tools, and monetization platforms.

I’ve also built SaaS tools, digital products, open source projects, and various other things over the years. I’ve been making things on the internet for close to 20 years now, and I still get a little too excited when a new subscriber rolls in.

What is your current focus?

I’m building a small ecosystem of tools and content to help founders ship and grow.

On the product side, I’m working on AutoChangelog, which automates changelog generation from GitHub pull requests, and Preflight, a CLI tool that scans for deployment issues across 70+ services. Both target developers who ship regularly. Preflight is written entirely in Go, which is something I’ve been meaning to get deeper into for a long time.

On the content and distribution side, I run DailyPhotoTips with 27,000 subscribers and TheDailyPreset with over 9,000 subscribers.

I just launched the Email Growth Guide, which is everything I wish I knew about email and audience building when I started. I also recently launched Distribution Kit to help fellow founders find places to submit their projects and get early traction and users.

The common thread across all of this is building things that run without me needing to be there 24/7. That’s why I’m so bullish on newsletters. I can schedule a month’s worth of emails and move on to other things. The system keeps working while I focus elsewhere.

Why do you believe newsletters are such a strong opportunity for entrepreneurs today?

Email has been declared dead more times than I can count, and yet here we are.

Every social platform that was supposed to replace it has either disappeared, changed its rules dramatically, or become pay-to-play. Email just keeps working.

What makes email powerful is its directness. You write something, you hit send, and it shows up in someone’s inbox. There’s no feed ranking your content against a million other posts. There’s no algorithm deciding you need to pay to reach people who already signed up to hear from you.

The person on the other end either opens it or they don’t, but the choice is theirs.

I’ve been running newsletters for over a decade now, and the economics still make sense. You don’t need a massive audience to build a real business. A few thousand engaged subscribers who trust you and actually read what you send can generate meaningful revenue through sponsorships, affiliates, or your own products.

And unlike followers on a social platform, those subscribers are yours. You can export them, move them to a different provider, and reach them regardless of what happens to any single company.

The barrier to entry is also incredibly low. You can start a newsletter today for free and be sending emails by tonight. No approval process, no waiting for the algorithm to bless you, no gatekeepers. Just you and whoever wants to read what you write.

Why is owning an audience more important than ever?

Because the platforms keep reminding us that we don’t actually own anything we build on them.

I’ve watched this cycle play out repeatedly over the past two decades. A platform gets popular, creators and businesses pour time and money into building audiences there, and then the rules change. Sometimes gradually, sometimes overnight. Organic reach gets throttled, monetization policies shift, features get deprecated, and accounts get suspended for reasons nobody can explain.

The creators who survive these shifts are the ones who were always driving people back to something they controlled. An email list, a website, a direct relationship that doesn’t depend on a third party’s business decisions.

When I sold Contrastly, the buyer wasn’t paying for our social media presence. They were paying for the email list. 100,000+ people who had raised their hand and said, “Yes, I want to hear from you.”

That’s a tangible asset with real value. You can’t say the same about Instagram followers or YouTube subscribers, because those audiences belong to the platform, not to you.

The smart move is to use social platforms for what they’re good at, which is discovery and reach, while always funneling people toward something you own.

Treat social as the top of the funnel, not the foundation.

What misconceptions do entrepreneurs have about email marketing?

The biggest one is thinking you need to have everything figured out before you start. People wait until they have the perfect lead magnet, the perfect landing page, the perfect welcome sequence. Meanwhile, they’re not sending anything to anyone.

I’ve seen people spend months setting up elaborate automation flows for a list that doesn’t exist yet. All that infrastructure means nothing if you haven’t proven that people actually want what you’re offering. You can build the fancy stuff later. Start by sending emails and seeing if anyone cares.

Another misconception is that more subscribers is always better. A big list full of people who don’t open your emails is worse than a small list of people who actually engage.

Deliverability suffers, your metrics look terrible, and you’re paying to host a bunch of dead weight.

I’d rather have 5,000 subscribers with a 50% open rate than 50,000 with a 10% open rate.

People also underestimate how long it takes to see results. Building an audience through email is a slow burn.

You’re not going to send three emails and suddenly have a thriving business. It takes months, often years, of consistent showing up before the compounding really kicks in.

The people who succeed are the ones who keep going when the numbers are small and discouraging.

How narrow should a newsletter topic be?

Narrow enough that when someone lands on your signup page, they immediately know whether it’s for them or not.

If you’re trying to appeal to everyone, you end up appealing to no one. People subscribe to newsletters that solve a specific problem they have or speak to a specific interest they care about.

The more clearly you can articulate who this is for and what they’ll get, the easier it is for the right people to say yes.

TheDailyPreset is a good example. It’s daily Lightroom presets for photographers. That’s it. You know exactly what you’re signing up for. There’s no ambiguity. Either you want daily presets, or you don’t.

Now, you can go too narrow. If your topic is so specific that only 47 people in the world care about it, you’ll have a hard time building something sustainable.

But most people have the opposite problem. They’re too broad because they’re afraid of excluding potential subscribers. The reality is that specificity attracts. When you speak directly to a particular group of people, they feel like you get them.

That connection is worth way more than casting a wide net and hoping someone bites.

What growth tactics have been the most reliable for you?

Showing up every single day for years. That’s the boring answer, but it’s the true one.

People want growth hacks and viral tactics, but the thing that actually moves the needle over time is consistency.

When you send daily emails for years, you build a relationship with your readers that’s hard to replicate any other way. They trust you because you’ve proven you’re going to be there. That trust converts to opens, clicks, purchases, and word of mouth.

Beyond consistency, cross-promotion has been valuable. Finding other newsletter operators in adjacent spaces and doing swaps or shoutouts can introduce you to audiences who are already primed for what you’re offering.

These are people who read newsletters, who have given out their email address before, and who are interested in topics related to yours. They’re much easier to convert than cold traffic.

I’ve also found that making it dead simple to subscribe helps more than people realize. A clear value proposition, minimal friction, and no elaborate multi-step signup process. Just tell people what they’ll get and ask for their email. Every additional field you add, every extra click you require, costs you signups.

Are lead magnets still worth using?

They can be, but they’re not mandatory.

A good lead magnet can definitely boost your signup rate. If someone’s on the fence, offering them something valuable in exchange for their email can push them over.

But I’ve also seen lead magnets attract people who only wanted the free thing and have no intention of sticking around. Your open rates tank, your engagement suffers, and you end up with a bloated list full of people who aren’t really your audience.

If you’re going to use a lead magnet, make sure it’s genuinely aligned with what your newsletter is about. You want it to attract the right people, not just any people.

A lead magnet that’s loosely related to your topic will bring in subscribers who unsubscribe the moment they realize your regular emails aren’t what they signed up for.

For a lot of newsletters, a strong value proposition is enough. If you can clearly communicate what subscribers will get and why it matters, plenty of people will sign up without needing a bribe. I’d rather have fewer subscribers who actually want to be there than a bigger list of people who grabbed a freebie and forgot about me.

How do you determine the frequency of your emails?

I ask myself two questions. How often can I realistically show up without burning out? And how often does my audience actually want to hear from me?

For DailyPhotoTips and TheDailyPreset, daily makes sense because the content is quick and actionable. A single tip or preset doesn’t take long to consume, and photographers enjoy having something new to try each day.

Daily also builds a strong habit. Readers come to expect the email at a certain time, and that consistency keeps engagement high.

For other types of content, daily would be exhausting for both me and the reader. Long-form essays, detailed tutorials, and in-depth analysis all take more time to create and more time to consume. Weekly or biweekly makes more sense for that kind of content.

The worst thing you can do is commit to a frequency you can’t maintain. If you say you’re going to send weekly and then disappear for three months, you’ve broken trust. It’s better to start with a sustainable cadence and increase it later than to overpromise and fall off.

What are your favorite ways to monetize a newsletter?

Sponsorships and affiliates have been the bread and butter for DailyPhotoTips and TheDailyPreset. We have a clear audience of photographers, and there are plenty of companies selling products to that audience. Gear manufacturers, software companies, and education platforms all want to reach people who are actively engaged with photography.

A well-placed sponsorship or affiliate recommendation can generate meaningful revenue without feeling salesy, as long as you’re recommending things that genuinely serve your readers.

Selling your own products is another strong path. When you have an audience that trusts you, launching a digital product becomes much easier.

You don’t need to spend money on ads or figure out complicated distribution strategies. You just email your list and tell them about it. For Contrastly, I sold presets, guides, and educational bundles, and the email list was the primary sales channel for all of it.

I’m a fan of monetizing from day one. There’s no rule that says you need to wait until you hit some arbitrary subscriber count before you start making money.

If you have something valuable to offer, whether it’s a product, a sponsorship slot, or an affiliate recommendation, include it. Readers understand that running a newsletter takes effort, and they don’t expect everything to be free forever. Starting early also helps you figure out what your audience actually responds to, which informs how you grow and what you build next.

Why did you decide to write the Email Growth Guide now?

I’ve spent over a decade learning this stuff the hard way, through trial and error, failed experiments, and eventually figuring out what actually works.

I kept having the same conversations with other founders about email, answering the same questions, giving the same advice. At some point it made sense to just write it all down.

I wrote the whole guide over the 2025-2026 holiday break. I sat down and let it pour out, and it reminded me how much I enjoy the process of writing and teaching. Everything in the guide comes from real experience running real newsletters. It’s practical, not theoretical.

I also wanted something to point people to instead of repeating myself. Now, when someone asks me how to grow their newsletter or how to think about monetization, I can send them to emailgrowthguide.com and know they’re getting the full picture.

What would you tell entrepreneurs starting from zero today?

Start before you’re ready.

You’re never going to have the perfect setup, the perfect niche, or the perfect content strategy. The only way to figure out what works is to actually start doing it and learn as you go.

Send your first email to whoever will listen. Your friends, your colleagues, people you’ve met online. It’s going to feel awkward and self-promotional, and that’s fine.

Everyone who’s built an audience started by telling people they already knew.

Then just keep going. The first hundred subscribers will feel painfully slow. The numbers will be discouraging. You’ll wonder if anyone cares. Keep sending anyway. The people who succeed at this are the ones who don’t quit during the slow early phase.

And be patient with yourself.

Building something real takes time. I’ve been doing this for close to 20 years, and I’m still learning. The compounding effects of consistency are real, but they take a while to show up. Trust the process, keep showing up, and give it time to work.