People of Media: Tim Huelskamp | The Business Model Tinkerer | 1440
Meet Tim Huelskamp
Are you intellectually curious? Then you’re in the right place. I got to interview Tim Huelskamp, CEO of 1440, the “knowledge company for the intellectually curious.” We dove deep into a variety of topics, including the power of mentorship and its role in shaping careers and lives. I got the wonderful opportunity to call out the generous and entrepreneurial spirit inside this amazing man.
Tim’s work with Fifth Star Funds, an initiative providing startup capital to underrepresented founders, is a perfect example of his philosophy of generosity and entrepreneurship. By giving entrepreneurs without access to “friends and family” funding a chance to thrive, he’s creating opportunities where they didn’t previously exist. Tim remembers the times when people gave him a leg up when they didn’t have to, and this motivates him to create opportunities for others.
Breaking the Mold with 1440
When Tim first shopped the idea of 1440—a newsletter for the intellectually curious—to marketing experts, the feedback was clear: “It’ll never work.” Experts told him, “Riches are in the niches,” and argued that intellectually curious people weren’t a narrow enough audience. But Tim saw a white space—an unmet need in a market flooded with fake news, bias, and hidden agendas. He believed people were longing for something trustworthy, digestible, and unbiased.
That belief paid off. Today, 1440 serves over 4 million readers, proving that sometimes you have to look beyond “how things have always been done” to create something that deeply resonates. Tim’s story is a powerful lesson in following your instincts and building where others see no opportunity.
For the local publisher reading this — I think this provides a valuable nugget. People are saying a lot of things about what local media has to do to survive. The experts are often saying contradicting things. “Go here, go there, try this technology.” But at the end of the day, don’t ingnore your intuition. You have the power to tap into the deep needs and frustrations of YOUR PEOPLE. You know your audience better than anyone, or you wouldn’t have gotten where you are. Let that same song of your audience’s felt need carry you to new avenues by which you can meet that need. This is the work — not just sifting through the impossible hodge podge of options. </RANT>
Playing with Legos
Tim’s passion for exploring and refining business models is nothing short of a superpower. He approaches it with the joy and creativity of a child playing with Legos—seeing possibilities, trying combinations, and building something remarkable piece by piece. Whether it’s developing 1440’s learning platform or scaling initiatives like 5th Star Funds, Tim’s ability to see the “white space” where a model can thrive is extraordinary. His enthusiasm for tweaking, testing, and perfecting ideas until they resonate with customers is what sets him apart as both an entrepreneur and an innovator.
Balancing Profit and Purpose
Tim’s approach to business is rooted in balancing profit with purpose. His leadership demonstrates how businesses can complete the golden triangle of (a) serving their customers, (b) delighting employees, and (c) aiming for the greater good. Tim has a deep value and commitment to creating a strong team culture that prioritizes joy, purpose, and work-life balance—a rare and admirable focus in today’s world of bottom-line obsession.
Seeing the Bigger Picture
Tim’s story is a reminder to believe beyond common wisdom, challenge the status quo, and build something truly meaningful where others see “impossible,” all while having fun and creating a shared sense of purpose with a tribe of invested collaborators — not just “employees.”