Chris Shipley on the Art of Elevating Entrepreneurs
Chris Shipley on Building Resilient Entrepreneurs and the Importance of Collaboration
The longtime Pipeline collaborator talks about why founders matter most, how diversity fuels innovation, and the magic of mentorship.
By Abram Shaffer
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INTRODUCTION
Chris Shipley has spent more than 30 years helping entrepreneurs take their ideas from napkin sketches to market success. Known for her tenure leading the DEMO Conference, where she helped launch some of the most recognizable tech companies of our time, Shipley has made a career out of spotting potential and nurturing innovation. But for Shipley, it’s not just about the companies—it’s about the people behind them.
As a longtime collaborator with Pipeline Entrepreneurs, a program that prioritizes putting founders first, Shipley has seen firsthand the transformative impact of focusing on the individual, not just the business. Over the past 15 years, she’s helped countless entrepreneurs navigate the complex world of startups, all while emphasizing the importance of resilience, collaboration, and storytelling.
In this conversation, Chris opens up about what makes a successful entrepreneur, the evolving role of mentorship, and why the Midwest might just be the next big thing in the world of startups. She also touches on why diversity isn’t just a box to check, but a necessary ingredient for innovation, and how Pipeline is working to create a more inclusive ecosystem for the next generation of entrepreneurs.
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Abram Shaffer: So, Chris, let’s kick this off by having you introduce yourself. Who are you, and what do you do?
Chris Shipley: Sure. I’m Chris Shipley, and I’ve been in the tech industry for, well, a long time, helping entrepreneurs shape their businesses and bring their products to market. I’ve been with Pipeline for over 15 years, helping founders develop their messaging and marketing strategies. It’s been an amazing journey.
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Abram Shaffer: Pipeline has this big focus on putting the founder first. With everything you’ve seen in the startup world, why do you think that’s so important, especially right now?
Chris Shipley: You know, at the earliest stages, it’s really all about the entrepreneur. It’s their vision, their hustle, their values that form the company’s foundation. Companies will come and go, but the entrepreneur? They keep growing, building, and creating. So when you focus on them, on the person, rather than just the business, you’re investing in something that lasts beyond a single venture. Especially now, with how fast things change—new tech, new ideas—having strong, adaptable founders is more important than ever.
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Abram Shaffer: That makes total sense. Now, when it comes to collaborations in Pipeline—specifically between a fellow and a mentor—what do you think makes that work so well?
Chris Shipley: It’s all about mutual learning. I think there’s this idea that the mentor is this all-knowing figure, and the entrepreneur just soaks up all that wisdom. And sure, mentors impart a lot, but honestly, they learn just as much from the entrepreneurs they’re guiding. It’s a two-way street, and when that happens, the relationship becomes something deeper and more enduring. I’ve seen Pipeline do a really great job of creating those matches, and over time, you kind of forget who’s mentoring whom because both sides are growing.
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Abram Shaffer: You've been with Pipeline for over 15 years now. In that time, have you noticed any patterns or key traits in the most successful entrepreneurs coming through the program?
Chris Shipley: I’m lucky enough to see the fellows at the end of their year, after they’ve had time to grow. And what stands out is resilience. It’s this ability to get knocked down and get back up, time and again. These founders realize that what they came into the program thinking they’d do might not be what they end up doing, but they adapt. And that’s key—because entrepreneurship is hard. If you can face those challenges, learn from them, and keep going, you’re going to succeed in the long run. Pipeline creates this space that embraces that rollercoaster and supports entrepreneurs through it.
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Abram Shaffer: Earlier today, you touched on the idea of crafting stories that don’t just appeal to one audience. How do you coach entrepreneurs on telling well-rounded stories, especially when it comes to talking to investors versus customers?
Chris Shipley: Yeah, so, your business is a story, right? And you want people to connect with it. Sometimes that story draws people in, and sometimes it helps you figure out who shouldn’t be along for the ride. When you’re talking to different audiences—whether it’s investors, potential hires, or customers—the core of your story stays the same. It’s the heart of your business. But you adapt the way you tell it to resonate with each group. You don’t change the essence, just the delivery.
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Abram Shaffer: I love that. Speaking of stories, we often hear about how little funding goes to women and founders of color. How do you think Pipeline is helping to shift that narrative? And where does the wider entrepreneurial space need to step up?
Chris Shipley: Oh man, where do I start? I’ve been working on this for almost 30 years, and the stats haven’t really changed—only about 4-5% of venture funding goes to women, and even less to women of color. It’s not always intentional exclusion, but investors tend to pattern-match. They fund what they know, and for decades that’s been white male engineers. When someone who doesn’t fit that mold comes along, they’re often overlooked, and it’s to everyone’s detriment. Pipeline recognizes this and is actively working to change it by widening the lens on what an entrepreneur looks like. This isn’t just a feel-good diversity push—it’s about tapping into underrepresented markets and unlocking new opportunities.
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Abram Shaffer: So true. I also want to ask—why do you think the Midwest gets counted out so often? And why is it important for entrepreneurs to build businesses here, instead of just heading to the coasts?
Chris Shipley: The Midwest is critical, not just for the region but for the whole U.S. economy. You can’t just move everything to San Francisco or New York and call it a day. There are real problems in the Midwest that need solving, and when entrepreneurs focus on those challenges, they create solutions that benefit everyone. Plus, there’s a national security aspect to it—when you build strong, vibrant communities in the heart of the country, you’re strengthening the nation as a whole. We need more entrepreneurship here to keep the whole ecosystem thriving.
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Abram Shaffer: Definitely. Last question: what advice would you give to someone who’s thinking about joining a program like Pipeline but might be on the fence?
Chris Shipley: Starting a business is one of the hardest things you’ll ever do. Don’t do it alone. Programs like Pipeline give you a community—a support system that accelerates your growth in ways you can’t achieve on your own. Why reinvent the wheel when there’s an entire network of people who’ve been where you are, willing to help you grow? If you have the chance to join something like Pipeline, jump in with both feet. You won’t regret it.