Started her newsletter 6 months ago, now 3K+ newsletters recommend her!

How We Grow by Ana Calin

Mar 09, 2025

Newsletter Circle is your go-to source for building a successful newsletter business through a paid subscription.

👋 MEET THE CREATOR

Ana Calin is a marketing specialist with over 15 years of experience in roles such as brand strategist and client services.

After years of working for others, she decided to build a portfolio career—amassing over 1 billion views and generating $1M in brand deals in just 1.5 years.

Six months ago, she launched How We Grow, a newsletter dedicated to helping others build a profitable portfolio career. In just five months, it skyrocketed from 0 to 42,000 subscribers—11,000 of whom joined in the last month alone! Plus, more than 3,000 other publications on Substack recommend her newsletter.

She also adopts an unconventional pricing strategy by charging $97/month and $177/year for paid content to encourage long-term commitment.

Her story is both inspiring and packed with valuable insights. Are you as excited as I am to dive into Ana’s journey?

In this interview, you'll learn:

Why she added a newsletter to her $1M personal business
How she grew over 42,000 subscribers in just 6 months
Her strategy to become a Substack bestseller with around 500 paid subs
The thinking behind her paid subscription pricing strategy ($97/month and $177/year)

🏷 NEWSLETTER IDENTITY CARD

⚒️ TOOL STACK

ESP: Substack
Writing: Substackulous (Ana's Own App)
Task Management: Notion
Curation & Note taking: Notion
Research: Perplexity.ai
Productivity: AnswerthePublic, ChatGPT
Visual Design: Canva, Substackulous
Growth: Passionfroot* (brand deals)
Webinars: WebinarJam, Gamma
Digital Products: Notion, Designrr
Testimonials: Testimonial.to
Payments: Stripe, PayPal

🥁 START

You mentioned on your About page that you built a portfolio career with over 1 billion views, generating $1M in brand deals within 1.5 years.

How and why did you start a newsletter in the first place? What is the role of “How We Grow” in your professional life?

I started How We Grow because, after years of building a portfolio career—working with global brands, securing over $1M in brand deals, and generating more than 1 billion views—I realized something crucial: the secret to growth isn’t talent or luck, it’s systems. But no one was talking about the real behind-the-scenes of building a career with multiple income streams.

Everything I found was either too vague or too focused on hustle culture.

I wanted to change that.

How We Grow started as my open playbook—what actually works, what doesn’t, and how to build a portfolio career that’s not just profitable but fulfilling. In just 5 months, it grew from 0 to 42,000 subscribers (11,000 last month alone).

Why? Because people are tired of generic advice. They want honesty, practical steps, and someone who’s been in the trenches. That’s what I give them.

For me, How We Grow isn’t just a newsletter. It’s my proof that you don’t need to follow outdated career paths to succeed. It’s where I share everything I’ve learned—mistakes, wins, and all—and in return, it fuels my own growth. From paid subscribers to brand deals, it’s become a core part of my business.

But more importantly, it’s my way of showing that you can build something extraordinary without sacrificing your sanity. And trust me, that’s way more valuable than any 9-to-5 grind.

How would you describe your content in five key points?

I write about what actually helps people build a portfolio career and make a living online—without losing their minds.

That means:

Audience growth (because no audience, no business)
Monetization strategies (brand deals, paid content, multiple income streams)
Personal branding (being unforgettable online)
Content that sells (because likes don’t pay bills—subscribers do)
Behind-the-scenes of building my own career (the wins, the flops, and everything in between)

Basically, if it helps you grow, make money, or stand out online, I’m writing about it. And if it’s trendy but useless? I’m probably roasting it.

What does your audience look like?

They’re smart, no-BS, and allergic to cookie-cutter advice.

They’re creators, founders, freelancers, and solopreneurs who want to build multiple income streams, grow their audience, and actually get paid for their work.

They’re tired of the “hustle harder” advice and want systems that work. And they’re not afraid of bold ideas, honest feedback, or a little controversy.

Global actors, equal split between women and men.

🚀 GROWTH

You grew your subscriber list from 0 to 42,000 in less than 6 months. This is impressive! How did you gain your first 1,000 subscribers?

I got my first 1,000 subscribers by being everywhere. I didn’t wait for people to “discover” me—I dragged them in. LinkedIn, Twitter, emails, DMs... if you knew me, you knew about my newsletter.

But here’s the part no one tells you: people subscribe because they trust you, not because you asked nicely. I’d spent years sharing no-BS advice, so when I launched How We Grow, my audience thought, “If her free stuff is this good, the newsletter must be fire.”

No hacks, no magic—just consistent value, shameless promotion, and actually giving a damn about my readers.

Which strategies did you use to grow over 35,000 subscribers?

1,000 – 10,000 Subscribers

Getting the first 1,000 subscribers is always the hardest part, but I did it by focusing on one thing most people overlook: building trust before asking for attention.

I didn’t start from scratch—I brought over 5,000 followers from my email list and social media, but that didn’t just happen overnight. For years, I’d been sharing valuable content on LinkedIn, growing my audience organically.

When I launched How We Grow, I didn’t just say, “Hey, subscribe to my newsletter.” I said, “Here’s why this newsletter will make your life easier, your brand stronger, and your bank account happier.” And people listened.

But the real secret to my first 1,000?
I treated every subscriber like gold. I replied to comments, asked for feedback, and made them feel part of something. I also shamelessly promoted my newsletter—on LinkedIn, Twitter, on my Forbes column, in DMs, and even in my email signature. I wasn’t subtle, and I wasn’t trying to be.

Also, I never begged for shoutouts or asked for favors. Instead, I recommended 300+ newsletters and brought them thousands of subscribers every month. Guess what? Now 3,000+ newsletters recommend me. Karma works fast when you actually give a damn.

10,000 – 20,000 Subscribers

I made my newsletter an open stage. Guest posts? Come in. Share your work. And it paid off—people stayed for me, but they also discovered others through me.

I also ditched the vague “Let’s grow together” nonsense and launched growth challenges with real, measurable outcomes.

Not “build your brand”—more like “get your first brand deal in 30 days.”

Specific wins = loyal subscribers.

20,000 – 30,000 Subscribers

Here’s a hot take: Monthly plans are cute, but annual plans build real relationships. I sold the long-term vision from day one because I wasn’t here to date my audience—I wanted the marriage. And I commented, engaged, and replied to everyone like my life depended on it.

Growth hack? No. Just being a human online.

30,000+ Subscribers

Want to know my “secret weapon”? My chat community.

It’s where ideas fly, deals happen, and subscribers turn into superfans.

If you don’t have a place where your audience can talk to you (and to each other), you’re leaving growth on the table.

And when 3,000+ newsletters are shouting your name? Growth becomes inevitable.

*Growth Graph of ‘How We Grow‘ between Nov 2024 and Feb 2025*

You are very active on Substack Notes, and some of your posts get hundreds of likes along with tens of restacks and comments.

Could you share 3 strategies that have worked best for gaining traction on Substack Notes and growing your list through publishing Notes?

1. Treat Notes like mini newsletters.

Most people post throwaway thoughts. I don’t. Every Note is a hook, a story, and a takeaway. If your Note doesn’t make someone stop scrolling, you’re just adding to the noise. I write Notes people can’t ignore—spicy opinions, real stories, and actual value. It’s not luck; it’s effort.

2. Give more than you take.

I engage a lot—not to boost my algorithm score, but because relationships matter. I restack, comment, and hype others without expecting anything back. Funny how that works—when you give freely, people remember you. And they subscribe.

3. Sell without selling.

I never write, “Subscribe to my newsletter.” Instead, I write Notes that make people think, “I need more of this.” Then they find my newsletter on their own. Make them subscribe by being too good to ignore. It works every time.

My bonus strategy:

Have a lot of fun with it. If you don’t enjoy it, what’s the point? Don’t feel like posting anything today, just restack one of your older notes. Feel like posting 10 notes, go ahead and do that.

Enjoying what you do is contagious.

💸 MONETIZATION

What made you decide to launch a paid newsletter? Did you launch paid subscription right from the start, or did you wait to see some growth potential first?

I launched paid subscriptions from day one. Why wait? If you believe in your work, charge for it. Simple.

But here’s the kicker—I didn’t just focus on paid subscribers. Even my free subscribers got irresistible offers. Actual value, not fluff. People thought, “If the free stuff is this good, the paid version must be insane.” And they were right.

I didn’t wait for “growth potential.” I made my offers too good to ignore—clear outcomes, real wins, and zero filler. That’s why people subscribed. Not because I begged, but because I made it impossible to say no.

Ana_Calin_How_We_Grow_Newsletter_Paid_Sub_Page

Your Substack is a bestseller with over 480 paid subscribers. What has been your most effective strategy for surpassing the 100-subscriber mark? What is your current strategy to convert free subscribers into paid ones?

Honestly, I’m still amazed at how fast How We Grow has grown. Seeing so many people trust me and stick around blows my mind every day. I didn’t have a “secret strategy”—I just showed up, gave more than expected, and shared real stories, not fluff. People don’t pay because you’re perfect; they pay because they trust you.

Current strategy?
Retention is everything to me. I focus on delivering what I promise—sometimes more—so people feel like staying is the easiest choice.

Growth comes after that. My free content sets the bar high, but my paid subscribers? They get the full playbook. No tricks, no pressure—just showing up, giving value, and appreciating every single person who’s along for the ride.

Your monthly subscription price ($97) is higher than many Substack newsletters, but your yearly price ($177) is much lower than it should be based on the monthly rate.

What’s the strategy behind this pricing?

I designed my pricing to encourage long-term commitment—because that’s how real growth happens. Monthly is $97, but yearly is $177. Why? Because I want subscribers who are serious about their growth, not just looking for quick wins. And it works—99% of my subscribers choose the yearly plan.

The math is simple: if you’re in for the long game, the annual plan is a steal. If you just want to try it for a month? Sure, but at $97, you’ll quickly realize that committing for a year is the smarter move.

What’s inside each level?

Free: You get access to my best audience growth and monetization insights—no fluff, no paywalling the basics. Plus a monthly no brainer offer - this month you get 30days of content, for example - which in itself is a treasure trove. My free content alone helps people grow, and many have monetized just by applying what I share.

Paid ($97/month or $177/year): This is where it gets real. You get monthly growth challenges with a clear outcome, live and replay workshops that break down exactly what’s working, and personalized feedback so you’re not just consuming content—you’re executing. Plus, access to tools, past workshops, and my subscriber chat, which is where the real magic happens.

Founding Membership ($1700 one-time): For those who want direct coaching and strategy—it includes four private calls with me ($3K value) and everything inside the paid membership. No renewals, no hidden fees—just hands-on help.

I didn’t price my newsletter for impulse buys. I built it for people who are ready to actually grow. That’s why nearly all my subscribers go annual—it’s the no-brainer choice.

What are the biggest lessons you’ve learned from running a successful paid subscription?

Oh, there are plenty. Here are my top three:

1. People don’t pay for information—they pay for transformation.

You can Google almost anything for free. What people want is clarity. They want someone to say, “Here’s what actually works, here’s how to do it, and here’s why you’ve been stuck.” The moment I stopped worrying about “giving too much away” and focused on helping people get results, my paid subs skyrocketed.

2. Consistency beats genius.

I’ve published when I was sick, tired, or just not feeling it. Why? Because showing up matters more than having a “perfect” idea. Some of my best-performing content wasn’t the most brilliant—it was the most consistent. Turns out, reliability is underrated.

3. Community is everything.

Here’s the truth: most people don’t just pay for content—they pay to belong. My subscriber chat? That’s where the magic happens. Wins are celebrated, questions get answered fast, and people feel seen. Without that community, How We Grow wouldn’t be what it is today.

Bonus lesson?

Pricing too low attracts people who never take action. Pricing higher? It attracts people who actually want to grow. And that’s who I’m here for.

📌 IMPACT & LEARNINGS

How did building How We Grow newsletter contribute to your life professionally and personally?

Professionally:

How We Grow changed everything. I went from juggling a million projects to building a business I actually love. It opened doors I didn’t even know existed—brand deals, coaching, and being recommended by over 3,000 newsletters (still wild to me). But more than that, it gave me freedom. I don’t rely on a single client or paycheck anymore. My newsletter isn’t just a side project; it’s the backbone of my entire portfolio career.

Personally:

I’m still amazed at how fast it grew and how many people trust me. It’s humbling. And it’s made me more intentional. I’m not chasing every new opportunity or burning out for “growth.” My focus is retention—delivering on my promises. It also gave me more time for what matters: my husband, my family, painting, gardening, and not feeling like I’m always running on fumes. How We Grow didn’t just build my business—it gave me my life back.

What would you do differently if you had a chance to start over How We Grow?

I’d probably stress less about “getting everything perfect” and just hit publish sooner. Honestly, half the things I overthought didn’t even matter. Readers don’t care if your layout is flawless or your logo is fancy—they care if your content actually helps them.

I’d also build my community earlier. My subscriber chat became the heart of How We Grow, and I wish I’d launched it from day one. Turns out, people don’t just subscribe for your content—they stay for the relationships they build around it.

Oh, and one more thing? I’d ignore every piece of advice that said “Narrow your niche” or “Give everything away for free.” Nope. My growth came from being me—sharing my wins, my failures, and my messy in-between moments.

But would I change the journey? Not really. Every mistake taught me something. And that’s why How We Grow isn’t just a newsletter—it’s proof that you don’t need a perfect start to build something great.

What would it be if you had the right to give one piece of advice to aspiring newsletter creators?

Stop begging people to care.

No one owes you their attention. Not your friends, not your followers, not even your mom. The internet is loud, and everyone’s fighting for a spotlight. So, earn it.

Be interesting. Have an opinion. Say something people disagree with. And please—stop posting “New newsletter just dropped!” like you’re Beyoncé. You're not.

The fastest way to grow? Make people feel something. Annoy them, inspire them, make them laugh—just don’t be forgettable.

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