Outside Insights

Hosted by Chris Burkhard

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Latest episode

Oct 2026

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About the show

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.

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60 recent

November 6, 20261 hr 5 min

Leadership Lessons from America's Toughest Prep School - Episode 80

Send us Fan Mail What does it take to build a community that can withstand adversity and continue thriving for generations? In this episode of Outside Insights, Chris Burkhard sits down with Anthony DePalma, former New York Times foreign correspondent and author of On This Ground: Hardship and Hope at the Toughest Prep School in America . Anthony shares the extraordinary story of St. Benedict's Prep in Newark, New Jersey, where leadership isn't simply taught in a classroom. Students lead daily meetings, hold one another accountable, and complete demanding experiences that build confidence, responsibility, and resilience. Chris and Anthony explore what makes this approach work, why emotional support is as important as high expectations, and how organizations can build cultures that endure beyond their founders. They also discuss Anthony's decades of reporting and writing, including his practical Seat Rule for overcoming writer's block and making progress on meaningful work. It's a conversation about leadership, community, resilience, and discovering what we're capable of when we're willing to do difficult things. Choose how you want to tune in: 🎧 Listen to the episode: https://www.buzzsprout.com/1499440/episodes/19357795 ▶️ Watch the conversation: https://youtu.be/6BthB-EeOnU Connect with Anthony DePalma Website: https://www.anthonydepalma.com/ LinkedIn: https://www.linkedin.com/in/anthonydepalma/ Featured Book On This Ground: Hardship and Hope at the Toughest Prep School in America by Anthony DePalma Learn More Outside Insights: https://outsideinsights.substack.com/ Placers: https://myplacers.com/

October 9, 202647 min

The Physics of Business Growth - Episode 79

Send us Fan Mail What if business growth has less to do with pushing harder and more to do with alignment? In this episode of Outside Insights , Chris Burkhard sits down with Philippe Bouissou , a physicist turned business leader who worked at Apple under Steve Jobs and went on to study why some companies grow while others stall. Philippe shares his approach to understanding growth through the lens of alignment, particularly the connection between what a company offers and what the market actually wants. Chris and Philippe explore why companies can do many things right and still struggle to grow, what leaders often misunderstand about their market, and how identifying areas of misalignment can create a clearer path forward. They also talk about the importance of authentic relationships and why sustainable growth is about more than simply pushing harder. If you've ever looked at a business and thought, “ We should be growing faster than this ,” this conversation offers a different place to look for the answer. Choose how you want to tune in: 🎧 Listen to the episode ▶️ Watch the conversation Connect with Philippe Bouissou Learn more about Blue Dots Partners Learn more about Outside Insights Learn more about Placers

September 18, 202654 min

What If We Have the Job Search Backward? - Episode 78

Send us Fan Mail What if we have the job search completely backward? We are taught that companies do the hiring. Bobby Moesta sees it differently: “Employees hire companies more than companies hire employees.” In this episode of Outside Insights, Chris Burkhard sits down with Bobby Moesta , co-creator of the Jobs to Be Done framework and co-author of Job Moves: Nine Steps for Making Progress in Your Career . Drawing on research into more than 1,000 career transitions, Bobby shares a different way to think about career progress. He and Chris explore the four career “quests,” how to identify what gives you energy and what drains it, why every career decision involves trade-offs, and how to better understand what you're actually looking for before making your next move. They also dig into a bigger idea: the best person to manage your career is you. Whether you're actively considering a career change or simply wondering what your next chapter could look like, this conversation offers a fresh way to think about what's next. Choose how you want to tune in: 🎧 Listen to the episode ▶️ Watch the conversation Connect with Bobby Moesta Explore Job Moves: Nine Steps for Making Progress in Your Career Learn more about Outside Insights Learn more about Placers

August 14, 202649 min

Your Company Culture is Broken. And Yes, It’s Your Fault - Episode 77

Send us Fan Mail "Culture eats strategy for breakfast." We have all heard the phrase popularized by Mark Fields, but if your team engagement is dragging, turnover is high, or your daily meetings feel like a waste of time, it is time for a harsh reality check. In Episode 77 of Outside Insights , host Chris Burkhard sits down with multi-time entrepreneur, speaker, and best-selling author of Worth Doing Wrong , Arnie Malham . Returning to the show five years after his first appearance on our Culture Reflects Leadership episode, Arnie delivers an unfiltered masterclass on why your company culture is a direct reflection of your leadership, good, bad, or indifferent. Chris and Arnie dive into the exact tactical playbook to stop pushing your team and start leading them, including: The Mirror Test: Why you need to stop blaming clients, employees, or your industry and look directly at your own leadership style. Bottom-Up Culture: How to stop trying to be the single "rah-rah" person and successfully delegate culture projects to champions lower on your org chart. Fixing Broken Huddles: Why generic updates like "doing calls and meetings" kill productivity, and how to bring brutal specificity back to daily huddles. Toxic Superstars: How to handle the high-performing, high-billing employee who refuses to align with your values. Continuous Growth: Why reading must be built into your leadership habit and how books accelerate your pattern recognition. Stop waiting to focus on culture "when you make money." Hit play to learn how fixing your culture is exactly how the money gets made. 📚 Resources Mentioned in This Episode: Featured Guest Book: Worth Doing Wrong: The Quest That Builds a Culture That Rocks by Arnie Malham Culture & Reading Platform: The Better Book Club (founded by Arnie Malham) Leadership Primer: The Leadership Challenge by James Kouzes and Barry Posner Classic on Hiring: Who by Geoff Smart and Randy Street Classic on Meetings: Death by Meeting by Patrick Lencioni New Release Feature: What to Make of a Life by Jim Collins Connect with Arnie: Explore his speaking and consulting work at worthdoingwrong.com If this episode made you a little uncomfortable or gave you practical ideas to take back to your team, please subscribe, leave a review, and share this with a leader who needs to hear it!

July 17, 202656 min

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!

June 18, 202650 min

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.

June 15, 20261 hr 1 min

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).

April 24, 202643 min

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. Frankl Stillness Is the Key — Ryan Holiday Alone Together — Sherry Turkle The Second Mountain — David Brooks Connect with Tracy: Website: tracydavidson.com Personal Development: liftingyourvoice.com

March 27, 202646 min

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 Website LinkedIn Instagram Until 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.

February 27, 202656 min

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 2001 What banks look for (and why) Community banking explained Banker vs. investor Finding the right fit (yes, banks have personalities) Marc Pelletier: https://www.meridianbanker.com/people/marc/