Welcome to our new interview blog series, where we sit down with successful newsletter creators to chat about the inspirations as well as the secrets behind their newsletters.
Today, I’m excited to introduce you to Ana Calin, the creator of the How We Grow™ newsletter.
After stepping away from a high-stakes executive role due to burnout, Ana transformed her experience into a journey of creative exploration, which ultimately led to the launch of her newsletter. Now, with a thriving community of over 25,000 subscribers (!), Ana openly shares the ups and downs of her journey.
In her own words, she's not here to sell you an “overnight success” story but to share real, practical strategies that helped her scale.
Ana’s insights are packed with inspiration for anyone aiming to build a meaningful community and a profitable newsletter. She tells us what sparked How We Grow™, the smart (and not-so-smart) moves she made, how she approaches monetization, plus her best tips for begginners.
Enjoy and take notes!
What inspired you to start How We Grow™?
Ironically, it was burnout and the unrelenting pace of corporate life. After 15 years at the top, traveling constantly and feeling like I was ticking off boxes for someone else's goals, I hit a point where I had to ask, What's next?
I needed a shift from that lifestyle, and I wanted a career that didn’t feel like a race I never signed up for. After leaving that executive role, I tried art, started small businesses, and navigated this fascinating world of media and branding. And in that process, I realized how many other high-achievers, like myself, were secretly craving something different. They wanted careers that weren’t just about titles and bonuses but about creativity, autonomy, and growth. So, I launched How We Grow for people ready to break away from traditional paths and build something on their own terms.
My executive background played a huge role. It taught me about scaling, managing complexity, and, most importantly, what *not* to do if you want to avoid burnout. But instead of using those skills to serve a company, I’ve flipped them to serve a community.
Ana's newsletter sign-up page
Who is your target audience, and what can new readers expect when they sign up for the newsletter?
My target audience is solopreneurs, creators, high-performers, and anyone who’s itching to break free from the traditional, one-track career mindset. These people want options, autonomy, and, yes, financial success, but they also crave a lifestyle that lets them pursue diverse passions and multiple income streams without sacrificing who they are.
When new readers sign up for How We Grow, they’re stepping into a no-BS, straight-talk space where I share hard-won insights, practical steps, and even some contrarian views on building a career that serves them, not the other way around. Each edition is packed with stories, examples, and lessons from my own journey and from others who’ve dared to redefine success on their own terms.
So, expect a mix of inspiration, real-life tactics, and a little provocation.
A sneak peek at an issue from the How We Grow newsletter
Why did you choose Substack as your platform? Is there a specific feature that stands out to you?
I’d been on LinkedIn for a while, building my personal brand, but when I moved to Substack, I found my real vibe. On LinkedIn, it’s easy to get lost in the noise, but on Substack, people actually read what you have to say, engage, and—most importantly—stick around because they value the connection. The community aspect here is incredible. When you genuinely give back, whether it’s sharing an insight or answering a question, that energy comes right back to you.
I initially brought over little under 5,000 subscribers from my email list and social media, and that number grew to over 26,000 in just under three months. That’s a testament to Substack’s simplicity and the value of a system where you focus on what matters: post consistently, share notes that add value, and engage with your community. The real connection here is what makes it work.
Anything specific that worked out best?
This wasn’t a “purely organic journey.” like some would want to showcase. I went for a full-court press, using every lever I could pull, especially with my Forbes articles, where I also write as columnist.. Then, I exchanged guest posts and tapped into media outlets, pushing those articles right back to Substack.
It’s a two-way street: every feature or mention added social proof and a dose of curiosity. “Who is this person, and what’s this newsletter all about?”
Then, I crisscrossed my content on LinkedIn. Every post had a subtle (or not-so-subtle) nudge towards Substack. People underestimate LinkedIn’s reach for audiences craving real insights. Recommendations played a massive role too. When you make real connections on Substack, you’re not just building a readership; you’re creating a community.
Building here feels like a conversation, and that’s what keeps people invested. So, it wasn’t about hacking growth; it was about tapping into all these channels, making noise, and backing it with real value.
Could you share details about your current revenue from the newsletter?
My main revenue stream is coming from brands that I trust and who trust working with me. Mainly referrals and inbound and this brings in between $3,000 and $6,000 per month, depending on how often I accept publishing a brand ad. I am quite selective with them as I want my audience to not feel overwhelmed with sponsorships and I value their trust and respect, so I am only recommending brands that I trust as well.
How We Grow is a rather new newsletter, being on Substack only since the beginning of September now. Just last week I launched my paid subscription model I reached the best seller level on Substack, with 169 paid subscribers in a week. My current plans are $17 per month or $120 per year and I offer in this plan access to my marketing resources.
Weekly live workshops, Q&A and a Notes boost support within my community. Planning to extend this offer with coaching calls that I currently offer only to founding members. This brings the monetization level to roughly $20,000 USD per year.
For subscribers, I focus on a balance: a ton of useful, free content for everyone and then an exclusive layer for paid subscribers. The paid tier includes deeper dives and specific insights that go beyond the surface-level advice we all see online.
Upgrade option featured in an issue of the How We Grow newsletter
What has been the most rewarding part of your newsletter journey?
The most rewarding part has honestly been seeing the ripple effect. I started the newsletter thinking it would be a small space to share my thoughts on building a career outside the 9-to-5 grind, but it’s turned into this incredible community where people genuinely support each other’s growth. Watching creators and professionals not only connect with my content but also with each other, sharing their stories and strategies, has been beyond fulfilling.
There’s something powerful about showing people that they don’t have to stick to a single career track—that it’s possible to build a portfolio of passions and income streams that actually align with who they are. Every time I see a subscriber take a leap, try something new, or pivot their career, it reminds me why I started.
Plus, I’ll admit, I love the feedback and the questions that come in. Every time someone tells me how a post or a note made them rethink something, it feels like I’m not just building a newsletter; I’m part of a movement toward more authentic, meaningful work lives. It’s a community in the truest sense, and that keeps me inspired every day.
Do you have any go-to techniques or routines for keeping your content fresh and engaging?
Constantly listening to what’s happening in the community. I’m always in tune with what readers are discussing, struggling with, or curious about, and I turn those insights into content. It’s less about “content creation” and more about staying in a real conversation with people.
One routine I swear by is mixing up formats. Sometimes it’s a quick punchy note, other times it’s a deep dive. I also play with storytelling techniques—sharing personal anecdotes, industry stories, and even a bit of controversy to keep things engaging. Another thing that keeps me on my toes is cross-publishing on LinkedIn, which gives me a wider pulse check on what resonates, what doesn’t, and where people want to go deeper.
And let’s be real: nothing kills creativity faster than burnout. So, I keep it simple. My routine is post, notes, and engage. This way, I’m not getting bogged down in complex strategies. The simplicity keeps me sharp, and it keeps my content fresh because I’m always focused on the value rather than overthinking the process.
Any special advice for those starting a newsletter and hoping to make it profitable?
If I could give one piece of advice to new newsletter creators hoping to turn it into something profitable, it’s this: Start by building genuine trust before anything else. People can feel when you’re just trying to sell them something, and that’s a fast track to losing credibility. Instead, focus on delivering real, actionable value. Share insights, lessons, and even your mistakes—show people that you’re human and that you’re here to offer something they can’t just Google.
Another essential tip? Create a structure that’s sustainable. Start with a simple system—post regularly, engage with your readers, and experiment with shorter, engaging notes to keep the conversation going. Simplicity in the routine is what allows you to stay consistent, and consistency is what builds trust.
Lastly, don’t be afraid to mix in different monetization streams once you have a solid reader base. Think about ads, partnerships, or a premium tier, but only if it feels right for your audience.
Success is a funny thing—it rarely shows up on time, and when it does, it looks “overnight” to everyone else. Hitting 26,000 subscribers in three months sounds flashy, but honestly, it’s the result of years of throwing ideas at the wall, dusting off failures, and figuring out what actually *sticks*. I’ve experimented, pivoted, and yes, face-planted more times than I can count.
So, if you’re just starting out, remember: all those shiny “overnight success” stories are usually built on a mountain of trial and error. Embrace the missteps, laugh off the flops, and just keep going. The more you’re willing to experiment (and occasionally fall flat), the more you’ll figure out what makes your newsletter really resonate. And that’s where the magic happens!
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Thank you for talking to us, Ana!
Liked this? Check out our previous interview with the Hype Yourself Newsletter founder!
And if you have a favorite newsletter creator you'd like to see featured, please leave a comment–it might be our next pick.
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