Scaling a Business Sustainably with Castos Founder Craig Hewitt

Where do you get your news? These days, if you want to know what's going on in the world, you might scroll Twitter, skim LinkedIn, or catch a few headlines on Instagram. But increasingly, more people are turning to podcasts for deeper, more thoughtful takes on news, trends, and everything in between. Podcasting has become a powerful and accessible medium for content, connection, and community. And it’s turning into one of the more sustainable ways of scaling a business.

When Craig Hewitt started Castos, he wasn’t just launching another tech product—he was stepping into a space he deeply understood. As a long-time podcaster himself, Craig had firsthand experience with the frustrations of existing podcast hosting tools. So, when the opportunity came to acquire a WordPress plugin designed for podcasting, it was a no-brainer. That plugin became the foundation for Castos, a podcast hosting and analytics platform now used by thousands of creators around the world.

But like many startup journeys, what followed wasn’t a straight line. 

In the beginning, Castos grew organically. A few early enterprise customers came in through content marketing and word-of-mouth. That kind of traction feels like a dream for any founder, and it gave Craig the confidence to raise capital and build out the business. The logic seemed sound—if a few ideal customers found them on their own, surely they could attract more with the right strategy. But that assumption turned into one of the biggest lessons of his entrepreneurial journey.

The Hard Truth About Lead Generation

Craig and his team quickly discovered that lead generation isn’t something that scales automatically. Those early customers had found Castos naturally, but replicating that success at a larger scale proved difficult. It wasn’t just about getting more eyes on the brand—it was about finding the right leads at the right time, with the right budget, and the internal capacity to implement the solution.

Lead generation, as Craig now knows intimately, is the heartbeat of any successful business. And it’s one of the hardest things to get right. When he mentors other founders now, it’s often the first place he digs in. Businesses that thrive are usually the ones that crack the lead generation puzzle—consistently and sustainably.

A Cautionary Tale in Scaling a Business Too Fast

At the same time, Craig was navigating another common but critical challenge: cash flow and founder compensation. Like many early-stage entrepreneurs, he poured everything into the business, paying employees before himself and burning through personal savings. For a while, that felt like the noble, scrappy thing to do. But in retrospect, he sees how risky and unsustainable that approach was.

Reaching the point where he could pay himself a proper salary was a major milestone—not just financially, but mentally. It signaled that the business was becoming stable and self-sufficient. It also brought with it a realization: taking care of the founder is not a luxury, it's a necessity. After all, if you’re not in good shape—mentally, emotionally, and financially—how can you lead a team or grow a business?

Building a Foundation for Sustainable Growth

Craig’s shift toward sustainability didn’t stop there. When Castos joined SaaS accelerator program, and raised an oversubscribed funding round, it was more than just capital—it was validation. But rather than ramping up in every direction, Craig took a measured approach. Growth would be intentional, not reactive.

One of the biggest transitions he made was from being a do-it-all founder to building a team that could take ownership of specific functions. Bit by bit, he handed off responsibilities: product development, customer support, operations. This freed him up to focus on higher-leverage activities—namely sales and marketing.

But as any founder knows, hiring isn’t just about delegation. Every new team member is an investment, and Craig had to ensure each one was empowered to succeed. That meant more focus on leadership and team-building, and less on wearing every hat in the company.

Reinventing the Playbook

These days, Craig leads Castos’ sales and marketing efforts—and it’s a constantly shifting landscape. Traditional channels like SEO and pay-per-click advertising are less effective than they once were. Rather than chasing diminishing returns, Craig has leaned into a more modern and personal approach: founder-led marketing.

This shift has been game-changing. Building a strong personal brand, showing up on platforms like LinkedIn, launching his own podcast and YouTube channel, and creating authentic, helpful content—these strategies have delivered far better results than ads ever did.

Craig’s marketing playbook now starts with video-first content. He creates one rich, informative piece—whether it's a podcast interview, a tutorial, or a behind-the-scenes look—and repurposes it across multiple formats. Blog posts, LinkedIn threads, short clips, email content—it all flows from that original pillar. This strategy not only saves time but also ensures that Castos shows up in multiple places, speaking to its audience in the way they prefer to consume content.

Why This Strategy Isn’t Just for SaaS

While Craig leads a SaaS company, he believes these strategies are increasingly relevant across industries. Even if you run a traditional business—a manufacturer, a local service provider, or something more niche—there’s massive upside in becoming more visible and building trust through personal branding.

For some founders, especially in more conventional sectors, this might feel unfamiliar. But Craig argues that the benefits are clear. When the face of the company is actively building relationships, sharing expertise, and showing the human side of the business, everything gets easier—sales, hiring, customer loyalty, and even partnerships.

It’s not about becoming an influencer. It’s about being the relatable expert in your space, showing up consistently, and creating value. In today’s noisy market, people buy from people they know, like, and trust—and that starts with showing up.

Staying Ahead As A Leader

One of the most exciting shifts Craig is seeing—both for Castos and the broader business world—is the role of AI in sales and marketing. While he’s quick to admit that AI can feel overwhelming, especially with how fast it’s moving, he’s also a strong advocate for founders to start experimenting now.

From automating content creation to analyzing user behavior and personalizing outreach, AI offers massive leverage. But it’s not just about using tools—it’s about adapting your mindset. The companies that succeed will be the ones that embrace change, experiment often, and aren't afraid to scrap what’s not working.

Craig is particularly bullish on using AI to enhance, not replace, the human side of business. Tools can assist, but it’s still the personal touch—authenticity, thought leadership, connection—that wins over customers and keeps them around.

Intentional Leadership Creates Culture

Craig’s insights are a real masterclass in leadership, clarity, and intention. What stood out most was how grounded Craig is in the fundamentals: building a strong foundation, staying close to customers, and being incredibly deliberate about who he surrounds himself with. He said something that really resonated: culture is what happens when you’ve put your mission and vision in place. It’s not an accident—it’s the outcome of consistent, intentional leadership. 

At Castos, they don’t just talk about values during onboarding or on an internal slide deck—they live them. They hire against them. They use them to make decisions. And because of that, Craig says, it makes his job as a leader so much easier. Why? Because they’ve built a team of genuinely great people who believe in the same vision.

That kind of intentionality is rare, but it’s clearly been a major contributor to Castos’ growth and staying power.

As I reflected on our conversation, three takeaways stood out: confident leaders build personal brands that drive trust, they make tough decisions with the long game in mind, and they invest in the right people to help carry the vision forward.

If you’ve got your own takeaways or thoughts, drop a comment on YouTube or in the comments below. You can also tune in to the podcast episode for a deeper dive into Craig’s insights and experiences as a successful and effective leader.

Full episode here: Scaling a Business Sustainably with Castos Founder Craig Hewitt