Outside Insights

Chris Burkhard
  • 4.6 (10)
  • Entrepreneurship
  • Updated Monthly

Outside Insights with Chris Burkhard is a podcast for people who want more — more clarity, more purpose, more impact. Hosted by entrepreneur and lifelong learner Chris Burkhard, the show explores how bold leaders, builders, and thinkers close the gap between the life they have and the life they want. Through honest conversations and powerful stories, we unpack the lessons that shape real lives and careers. If you're looking for ideas that challenge you, motivate you, and help you grow, you’re in the right place.  🎙️ New episodes drop once a month. 🌐 Listen at myplacers.com/outside-insights 📩 Follow for fresh insights that meet you where you are, and push you further. 

  1. Jul 17

    The $200,000 Bratwurst Mistake (and 30 Years of Entrepreneurial Bliss) - Episode 76

    Send us Fan Mail What happens when you mix punk rock, hip-hop, and a relentless pursuit of culinary-centric brewing? You get Dogfish Head Craft Brewery. In this episode of Outside Insights, host Chris Burkhard sits down with founder Sam Calagione to unpack his 30-year journey of entrepreneurial bliss. From rewriting Delaware state laws at 24 years old just to open his doors, to orchestrating legendary collaborations with the Grateful Dead and Patagonia, Sam reveals how treating a business like a band can create an exponentially powerful culture. Chris and Sam dive deep into the real-world definition of partnership, the humility required to hand off parts of your business, and Miles Davis’s ultimate advice on finding your industry's "white space." Grab a cold one and tune in to learn how educating the head, heart, and hand can help you close your personal and professional gaps. In this episode, we discuss: The transition from a tiny 11-gallon system to a top 20 national craft brand.Why hospitality is the ultimate foundation for future entrepreneurs.The 10-year relationship that led to merging with Boston Beer Company.Sam’s obsessive "60-minute" rule for earning his beer calories.The hilarious "beer-infused bratwurst" mistake that delayed their canning line.Resources Mentioned: "Let My People Go Surfing" (Book by Yvon Chouinard)"Extreme Brewing" (Book by Sam Calagione)"On A Back Porch" (Vinyl collaboration with David Lemieux)Connect with us and listen to more episodes!

  2. Jun 18

    Changing the Community by Changing the Rules - Episode 75

    Send us Fan Mail This week on Outside Insights, I sit down with Logan Herring, the CEO of The WRK Group, to talk about how he has spent the last decade completely transforming community revitalization in Wilmington, Delaware. Logan challenges the traditional nonprofit model, arguing that social impact organizations should be run with the exact same professional infrastructure and financial discipline as top for-profit corporations. From turning around a failing community center to spearheading a massive 800-unit mixed-income housing development, Logan shares his exact blueprint for scaling with purpose. In this conversation, we get into: Why the nonprofit label is an operational disadvantage for social change.How to build a high-performance culture that balances deep passion with absolute professionalism.The strategy behind hiring for tomorrow instead of playing catch-up today.Mental Health Mondays and sustaining executive leadership at a high pace.The upcoming Purpose Built Communities Conference in Wilmington.Connect with Logan: theworkgroup.org  Books Mentioned JUMP: My Secret Journey from the Streets to the Boardroom by Steve Perry and Rocco Staino (Foreword by Logan Herring)P.S. Logan challenges every leader to practice the power of proximity. Urgency does not come from a corporate boardroom; it comes from being close to the people you serve. If this conversation resonates, forward it to a friend or colleague. Insight is meant to be shared.

  3. Jun 15

    Stop Overcomplicating Mental Health at Work - Episode 74

    Send us Fan Mail We’ve made mental health really hard at work. In this episode, Chris Burkhard sits down with Stephanie Lemek, founder of The Wounded Workforce, to simplify the conversation. Stephanie translates complex psychological concepts into actionable leadership tools. We discuss: Why accountability is a mental health tool.The "Three E's" of trauma and how they show up at work.How to use "Choice" to empower your team.Practical resources like 2-1-1 and EAPs.Connect with Stephanie: www.thewoundedworkforce.com  Recommended Books: The Good Life (Dr. Robert Waldinger) and What Happened to You? (Oprah Winfrey & Dr. Bruce Perry).

  4. Apr 24

    From Newsroom Chaos to Quiet Confidence: Finding Your Agency with Tracy Davidson - Episode 73

    Send us Fan Mail "I’m an overnight success 30 years in the making." For 40 years, Tracy Davidson was the face of Philadelphia news. But behind the anchor desk, she was quietly developing a toolkit for resilience and intentional living. Today, she’s stepping away from the screen to help you navigate your own ups and downs. In this episode, we dive into: The "Rubber Band" Theory: Why we feel stretched to the max and how to bring the tension back in.The Time Audit: A practical way to stop lying to yourself about how you spend your day.Radical Agency: Why Viktor Frankl’s principles are the ultimate antidote to feeling "stuck."Temporary Incompetence: Why being a beginner again is the secret to stoking your curiosity.Practical Stillness: Simple, "at the red light" practices to keep your faith and intentions front-and-center.Whether you're a leader battling burnout or just looking for a more purposeful way to show up for your family and yourself, Tracy’s wisdom on realistic optimism and quiet confidence will change how you view your day. Books mentioned: Man’s Search for Meaning — Viktor E. FranklStillness Is the Key — Ryan HolidayAlone Together — Sherry TurkleThe Second Mountain — David BrooksConnect with Tracy: Website: tracydavidson.comPersonal Development: liftingyourvoice.com

  5. Mar 27

    The Ocean Is Calling (and It Needs Your Talent) - Episode 72

    Send us Fan Mail Grant Otto on what 1,000 feet underwater can teach us about career purpose and the power of "waiting." “The biggest ‘career moves’ don’t start with a resume; they start with curiosity.” I recently sat down with Grant Otto, a marine scientist and researcher specializing in marine robotics. If that sounds like a job from a movie, that’s because it almost is, complete with stories of underwater ROVs getting tangled 1,000 feet down and “wet storage” missions to recover equipment worth more than a house. But Grant didn’t come on Outside Insights just to talk about how cool the tech is (though it is very cool). He came because he’s on a mission: he’s trying to get more talented people to care about the ocean. Three Lessons from the Deep 1. We need more than just “Turtle Lovers.” Most people get hooked on marine science by watching National Geographic. But to solve the massive challenges facing our oceans, warming waters, and rising acidity, Grant argues we need more than just biology fans. To build a “Blue Economy,” we need: Engineers and Builders to design resilient tech.Artists and Communicators to tell the story of our changing coastlines.Problem Solvers who aren’t afraid to get their hands dirty (or wet).2. The Power of the Cold Email Grant’s career didn’t start with a recruiter; it started with a cold email. While studying mechanical engineering, he realized he loved robotics and surfing. He asked a simple question: “What about marine robotics?” That curiosity turned into a Master’s degree and a career with deep purpose. 3. Surfing as Leadership Meditation We dove into the difference between work that “funds your life” and work that “defines you.” Grant shared a powerful perspective on surfing, describing as 80–90% waiting. For leaders who feel like they are constantly “pushing through,” Grant’s advice is a necessary pivot: Sometimes leadership isn’t about pushing harder; it’s about knowing when to get quiet enough to hear the right wave. Try This This Week Take five minutes of “waiting” time today, no phone, no music, no noise. Just observe. Like Grant waiting for a wave, use that quiet space to remember your “why.” 🎧 Listen Now Watch on YouTube | Listen on Buzzsprout Connect with Grant: Sea Saturated WebsiteLinkedInInstagramUntil next time, Chris P.S. You may notice a few small audio/video glitches in this episode. We had some technical issues during the recording. We debated re-recording it, but the conversation was too good (and too valuable) to lose. Thanks for sticking with it. If this conversation resonates, forward it to a friend or colleague. Insight is meant to be shared. Quick reviews on your listening app go a long way, too.

  6. Feb 27

    Banking, Trust, and the Entrepreneur’s First “Yes” - Episode 71

    Send us Fan Mail A conversation with community banker Marc Pelletier on trust, credit, and how entrepreneurs can walk into the bank with confidence Most entrepreneurs would rather go to the doctor than go meet a banker. So I brought on my first banker, and an old friend, Marc Pelletier to talk about what entrepreneurs actually need to know about banks, credit, and building trust. In this episode: How banking has changed since 2001What banks look for (and why)Community banking explainedBanker vs. investorFinding the right fit (yes, banks have personalities)Marc Pelletier: https://www.meridianbanker.com/people/marc/

  7. Jan 30

    Uncharted Moments: What Lewis & Clark Still Teach Us About Leadership, Listening, and Love - Episode 70

    Send us Fan Mail Why slowing down, listening better, and taking the long way still matters I sat down with Jeff Ton expecting a conversation about leadership and history. What I didn’t expect was how much we’d end up talking about attention, where we place it, how rarely we slow down, and what happens when we actually do. Jeff calls himself a “hippie coder turned CIO,” and that range alone tells you he’s lived in very different worlds. Over time, his love of leadership and fascination with Lewis and Clark merged into something more personal, eventually culminating in a book he’s finishing now called Uncharted Moments. It’s not out yet, but after reading an early version and talking with Jeff, I can tell you this isn’t a typical history story. Leadership Without A Clear Map One idea we kept coming back to was uncertainty. Jeff reminded me that Lewis and Clark carried a map that labeled most of the western territory as “conjectural.” Unknown. That didn’t stop them from moving forward, but it did require vision, trust, and adaptability. That challenge feels familiar today. Leading without perfect information isn’t a new problem, but it’s one we often forget has been solved before, by people who understood the value of relationships and shared purpose. Listening Changes The Story One of the most compelling parts of our conversation was about listening. Jeff talks about how his understanding of the expedition shifted when he stopped seeing it as a story of discovery and began to see it as a story of relationships, especially with Indigenous tribes who already knew the land. That shift didn’t just change how he understood history. It changed how he approached leadership, learning, and even his own marriage. Uncharted Moments Jeff uses the phrase “uncharted moments” to describe the experiences you can’t plan for, the ones that don’t announce themselves as important until much later. They’re the moments you only notice if you’re willing to slow down, take the side road, or stay curious a little longer than usual. It’s a simple idea, but one we don’t practice often enough. Where Are You In The River? Jeff shared a metaphor that I think many leaders will recognize. Imagine your team in a river, navigating the current every day. Sometimes you need to be in the water with them. Sometimes you need to be on the bank helping them find a way through. And sometimes you need to step back far enough to see the whole valley. Leadership isn’t about picking one role. It’s about knowing when to shift. Try This Week Take five quiet minutes and ask yourself: Where am I rushing past something worth noticing?Where do I need to listen more rather than pushing ahead?Where am I in the river right now, and where does my team need me to be?Listen To The Episode Jeff’s book Uncharted Moments isn’t out yet, and we’ll share more when it’s released. For now, the conversation and Jeff’s website are a great place to start. 👉 Watch the full episode of Outside Insights with Jeff Ton 👉 Visit Jeff’s website to sign up for his free newsletter and to learn more about his book. Until next time, friends, Chris If this conversation resonates, forward it to a friend or colleague. Insight is meant to be shared. Quick reviews on your listening app go a long way, too.

  8. Jan 2

    When Success Stops Being the Goal - Episode 69

    Send us Fan Mail I had the opportunity to sit down with Sam Maddula, a founder whose career does not fit a clean headline. What stood out immediately wasn’t the size of the business he built, but the decisions he made along the way, and the ones he chose not to make. This conversation isn’t about hacks or hypergrowth. It’s about judgment, timing, and the quiet moments when leaders realize the path forward isn’t obvious. A Business Built in the Margins Sam started his company in a highly specialized corner of healthcare, serving patients and physicians in situations where the stakes were high and the system rarely worked smoothly. Growth came, but not in the way business books describe it. Instead of rapid expansion, Sam talks about constraints. About capacity. About learning when “yes” would eventually cost more than it was worth. Those trade-offs shaped everything that followed. When Success Starts Asking Questions As the business matured, so did the weight of leadership. Responsibilities multiplied. Expectations rose. And life, as it does, introduced moments that forced Sam to reconsider what success actually required of him. We talk about what happens when the role you created begins to demand more than you’re willing to give, and how hard it is to admit that out loud. The Hardest Transition One of the most compelling parts of our conversation centers on transition. Not just the professional mechanics of stepping away, but the emotional and identity shift that follows. Sam shares what surprised him most about that period, what he underestimated, and what ultimately helped him move forward with clarity rather than regret. The Core Question Throughout the episode, one question keeps resurfacing: how do you build something meaningful without losing yourself in the process? Sam doesn’t offer formulas. He offers perspective shaped by experience, and the humility that comes from learning in real time. “You don’t really know what matters until you’re forced to choose.” This episode is a thoughtful look at leadership, transition, and the decisions that define a career long after the titles change. Click HERE to watch to the episode. Until next time, friends, Chris If this conversation resonates, forward it to a founder or leader who might appreciate it. Insight is meant to be shared.

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About

Outside Insights with Chris Burkhard is a podcast for people who want more — more clarity, more purpose, more impact. Hosted by entrepreneur and lifelong learner Chris Burkhard, the show explores how bold leaders, builders, and thinkers close the gap between the life they have and the life they want. Through honest conversations and powerful stories, we unpack the lessons that shape real lives and careers. If you're looking for ideas that challenge you, motivate you, and help you grow, you’re in the right place.  🎙️ New episodes drop once a month. 🌐 Listen at myplacers.com/outside-insights 📩 Follow for fresh insights that meet you where you are, and push you further. 

Information

  • Creator
    Chris Burkhard
  • Years Active
    2021 - 2026
  • Episodes
    87
  • Rating
    Clean
  • Copyright
    © 2026 Outside Insights
  • Show Website
    Outside Insights