Navigating AI in Creative Writing: Opportunities and Cautions

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Ever build a business that “looked” successful—but left you feeling empty? Jeff Hilimire sure did and then he did something about it. In this episode, we unpack how he turned a successful agency career into a mission-driven movement—building purpose-led businesses, launching a global volunteer initiative, and writing books that challenge how we think about impact.

Today’s featured guest always genuinely enjoyed agency life—something he quickly realized was the exception, not the norm. That realization led him to a mission: helping others discover greater meaning in their business journey. Whether it’s through his books, his leadership, or his venture that unites developers to build websites for nonprofits in just 24 hours, he is all about turning intention into action.

We have the pleasure of welcoming back Jeff Hilimire, the podcast's very first guest, nearly eleven years ago. He shares what drives him to help business owners build purpose-driven companies, why he started writing books, and how he carved his own path in the publishing world. You’ll also hear about his latest work with Purpose Group, his thoughts on operationalizing purpose, and how to lead with clarity through times of crisis.

In this episode, we’ll discuss:

• Why he made it his mission to help entrepreneurs build purpose-driven businesses.

• Using the concept of ‘Dream Small’ to build a network of volunteers to help non-profits.

• How he embedded his books with his unique vision. 

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Sponsors and Resources

Wix: Today’s episode of the Smart Agency Masterclass is sponsored by Wix Studio, the all-in-one platform designed to help agencies scale without the headaches. With intuitive tools, robust native business solutions, and low maintenance, Wix Studio lets your team focus on what matters most—delivering exceptional value to your clients. Ready to take your agency to the next level? Visit wix.com/studio and discover how Wix Studio can transform your workflow, boost profits, and strengthen client relationships.

From Joke Websites to Purpose-Driven Business Empire

Jeff's journey in the agency world began with simple curiosity in 1996 when, as a college student, he built joke websites with a friend. Eventually, they figured if they made it a business, they could keep doing what they loved, which led to building several sites for free and a humble start with their first paying client, Jeff’s aunt, who paid them $250 to build her business’ website.

Jeff has done a lot since being on the podcast’s first episode talking about that first agency. He’s been founding, growing, and selling businesses over the last 25 years. He has also been a board member of several initiatives and written six books just since 2019.

His latest venture is the Purpose Group, where he and his team acquire and reinvigorate small businesses by training more inspired and engaged employees through their Purpose Playbook™ methodology — which is very much linked to the knowledge Jeff has been sharing through his books, teaching entrepreneurs to build purpose-driven businesses, and helping them find that same joy he’s always found in his different businesses.

Start with One: How Dreaming Small Can Change Everything

In Jeff’s experience, many people never go after their dream projects because it feels too big and daunting to start. Instead, he believes it’s best to start small and give that first step. If your goal is to help people, then help at least one person.

This is the premise behind Jeff’s book Dream Small, which helped him grow his venture 48in48, an initiative born out of the idea of getting his team to help non-profits build websites. It would give them the satisfaction of helping someone while giving two selected non-profits a functional website in 48 hours. The plan gradually grew to include thousands of volunteers who offered time and expertise to help these non-profits for one weekend. Since developing this idea, Jeff has held 35 events with 7,500 volunteers around the world pitching in to help build 1,300 websites for non-profits. And while these numbers are great, he knows that had he started with that in mind, the project would’ve probably never taken off. People needed to see it was possible at a small scale before committing to do more.

Tired of Boring Business Books? So Was Jeff

Back when Jeff wrote his first book, he wanted to bridge the gap between traditional business thinking and entrepreneurial mindset. Having repeatedly encountered CMOs who resisted innovation with claims that they "couldn't take that chance," Jeff wanted to share his conviction that business was all about taking risks.

Initially, he intended to deliver a straightforward business manual and approached the writing process as such. However, he has personally never enjoyed those books, which became apparent as he navigated through the content and found that the rigidity of a traditional format stifled his creativity. Hence, he tried a different approach and embraced storytelling—creating characters and scenarios that embodied the entrepreneurial spirit. This is when Jeff found joy in the writing process and he’s continued developing stories within the same fictional universe.

Furthermore, after facing multiple rejections from traditional publishers, Jeff applied his risk-taking philosophy to launch his own small publishing house. Today, this venture works with approximately 25 authors and actively seeks innovative approaches to business storytelling.

Becoming a Better Leader by Setting a Purpose Beyond Profit

In his case, Jeff started out as the programmer in his partnership and oversaw that aspect of his agency’s operations for some time. The moment he hired someone else to help him with that task, he immediately recognized there were much better-qualified developers and that his own time would be better spent growing the agency.

In fact, he believes agency owners who have limited capacities and require help from the start can actually scale faster since they won’t get caught up working in the agency and can focus on growth. When founders recognize their limitations and delegate from the beginning, they avoid becoming trapped in day-to-day operations to focus exclusively on strategic growth opportunities.

Despite this operational insight, Jeff initially lacked a sophisticated vision beyond the vague goal of "eventually selling." It took time and experience for him to develop a more nuanced understanding of valuations and how different exit timings would affect the agency's ultimate value. His strategic thinking evolved only after navigating through multiple mergers and sales.

The most profound transformation in Jeff's approach came years into his business journey when he began thinking about purpose beyond profit. While he had always wanted to create a workplace where people enjoyed their work and developed professionally, he eventually expanded this intuition into a deliberate focus on organizational culture and consciously building values into the business foundation.

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