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“So if you're listening to this and you're starting a company, my best advice and the companies that I see succeed rapidly and have longevity are companies where the founder knows the audience knows the customer or is the customer.”
What if the key to scaling your business wasn’t about spending more, but about caring more? In this episode, we sit down with Natalie Frank, Head of Marketing and Community at Flodesk, who helped grow the bootstrapped email platform to over $30 million in recurring revenue, without relying on traditional advertising.
Natalie shares how she went from wedding photographer to tech executive, and the powerful philosophy that’s guided her journey: founder-market fit and community over competition. You’ll hear how Flodesk built a loyal audience through authenticity, radical transparency, and empowering small business owners to take control of their marketing.
Most software success stories focus on funding rounds, paid acquisition, or rapid growth tactics. Flodesk took a different path. Built without outside funding, the company grew to more than $30 million in recurring revenue by staying closely connected to the small business owners it serves and investing heavily in community.
In this Entreprenista Podcast, Natalie Franke shares her journey from wedding photographer to marketing executive, explains why founder-market fit is one of the most important factors in building a successful company, and offers a behind-the-scenes look at how Flodesk turned customers into advocates and community into a growth engine.
You can listen to the full episode on Spotify and Apple Podcasts.
Here Are a Few Moments From the Podcast
Natalie explains why understanding your customer is often the biggest growth advantage a founder can have:
"So if you're listening to this and you're starting a company, my best advice and the companies that I see succeed rapidly and have longevity are companies where the founder knows the audience, knows the customer, or is the customer, experienced the pain so acutely, so personally that when they're speaking to their audience, they come from a place of true emotional intelligence, understanding and a deep connection with the people that they serve.
If you don't feel like I'm saying founder market fit and you're going, I don't know that I'm there yet. I truly believe it's worth stopping everything you're doing and immersing yourself immediately, immersing yourself in the customer, their pains, really understanding their language and the nuance."
She shares the philosophy behind building Flodesk's marketing team:
"I really believe that people do their best work when they know in their soul it is work worth doing.
When they have a personal connection to the larger mission of the company, especially with what we do, supporting small business owners.
It wasn't just, can you do the job and do you have the skills? It was trying to understand, are they going to wake up in the morning and want to fight for our community?"
When discussing growth, Natalie argues that the most valuable marketing happens after the sale:
"The magic happens after conversion.
If you can take a customer and not just listen to them and then repurpose their content, but also iterate, improve, nurture their relationship, honor when they give you feedback, honor it. Treat them like a human and not a number.
Invest in those relationships, they become evangelists that you cannot buy. You must earn."
Natalie shares how Flodesk approached a major pricing change in a way that strengthened customer trust instead of damaging it:
"We took that playbook and we just chucked it out the window.
Instead we said, okay, look, these are our small business owners. How do we honor the ones that have believed in us from the very beginning?
So what we're doing is we're allowing them to lock in unlimited subscribers for as long as they choose to keep their plan.
We got email after email after email of our members saying, 'Thank you for honoring us.' And we had our highest spike in new trials and growth for the business."
Asked what entrepreneurship means to her, Natalie reflects on a life-changing moment before brain surgery:
"I remember very vividly in that moment thinking to myself, I'm really proud of what I've done on this earth.
It wasn't about what I had done on social media. It wasn't about the amount of money I had made.
The thing that I was most proud of was having the courage to do something for me. It was having the courage to pursue something I knew I was called to do.
And so I say, what does it mean to be an entrepreneur? It means to have the courage to make your mark on this world."
You May Also Like
- Abby Martinez of Well Balanced Business: Scaling Entrepreneurs with Systems, Strategy & Soul
- Why Trust Is the New Currency in Business and How Community Helps Build It
- Tried and Tested Tips for Securing Your Earliest and Most Loyal Customers
Curious about joining the Entreprenista League? Sign up here for a free info session.
Connect with Natalie:
Head to partners.flodesk.com/entreprenista to start your 14-day free trial, exclusively for Entreprenistas.
Thanks for tuning into this week’s episode of The Entreprenista Podcast - the most fun business meeting for women founders and leaders. If you enjoyed this episode, please subscribe to the show and leave a review wherever you get your podcasts.
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Updated on: June 26, 2026
Guests
Natalie Franke
Hosts
Stephanie Cartin
Co-founder of Socialfly and Entreprenista.
Stephanie Cartin is the co-founder and CEO of Entreprenista, an all-in-one platform – which includes a private community & business membership called The Entreprenista League that's made up of over 2,000 women founders at all stages of business, a weekly newsletter received by 60,000 readers, two podcasts, in-person educational & networking events, and an award program – that women founders at all stages can turn to for everything they need to grow.
Stephanie is also the co-founder of Socialfly (acquired by Truform Media Group in 2024), Markid, and Pearl Influential Capital. She has won countless awards, including the SmartCEO Brava award, which recognizes the top women CEOs in New York, and a Stevie Award for Women-Run Workplace of the Year. She has also appeared in Bloomberg, Forbes, Entrepreneur, Refinery29, and more.
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