In this special fireside chat edition of Startup Anthology, host Jeremy Willis sits down with Colonel (Ret.) Jim Orbock—a West Point grad, combat-tested US Army leader, and now, startup founder of Spartan Financial (https://spartanfinancial.pro/) in Austin, TX.

What You’ll Learn in This Episode:

• The leadership mindset that took Jim from leading troops in Afghanistan to launching his own business.
• How to transition from the military to entrepreneurship with purpose and confidence.
• Why “servant leadership” isn’t just a buzzword—it’s a culture-defining principle.
• The toughest part of startup leadership: letting go without losing control.
• Tactical advice for early-stage founders on team-building, narrowing vision, and staying aligned with your purpose.

Whether you’re a veteran exploring the startup path, a founder trying to build a resilient team, or someone fascinated by leadership under pressure, this episode is packed with wisdom, war stories, and real talk.

“If you aim at nothing, you’ll hit it every time.” —Jim Orbock

Recorded live at the Military-Connected Mentorship Meetup with support from Command Post Cohort, Texas Veteran Chambers Coalition, and sponsors including IVMF Bunker Labs, Combined Arms, Texas Veteran Commission, Capital Factory, and JPMorganChase.

Don’t forget to like, comment, and subscribe for more deep dives into startup leadership and culture.

Chapters

00:00 Introduction to Startup Anthology

01:01 Meet the Guest: Retired Colonel Jim Orbock

03:24 Jim's Journey to West Point

05:26 Transitioning from Military to Entrepreneurship

08:21 Lessons Learned and Advice for Entrepreneurs

11:19 Narrowing Your Vision in Business

13:12 Exploring Team Building and Mentorship

13:48 The Power of Vision and Goal Setting

15:13 Maintaining Focus and Intent in Business

15:51 Investing in People and Building Trust

18:07 Challenges of Leadership in Different Contexts

20:45 Servant Leadership and Organizational Spirit

21:45 Balancing Leadership and Delegation

26:05 Encouraging Psychological Safety and Freedom to Fail

28:08 Conclusion and Final Thoughts

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This highlight reel captures the candid insights and creative wisdom of Kent Richeson as he delves into the world of startups, innovation, and embracing imperfection. From quirky ideas like language-translating gum to finding inspiration from Spider-Man, this reel showcases the human side of entrepreneurship and the power of bold, imperfect thinking. 🌟 What You’ll Learn: • [00:00:00] The spark behind absurd ideas—like chewing gum that translates languages—and how imagination fuels innovation. 🧠 • [00:00:18] The 24/7 nature of startup life—beyond the 9-to-5 mindset. 💼 • [00:00:25] How even Spider-Man can inspire entrepreneurial thinking. 🕸️ • [00:00:38] The importance of vulnerability and human connection in business. 🤝 • [00:01:00] Building businesses that uplift communities and sustain others. 🌍 • [00:01:09] Why imperfection and experimentation are essential for growth. 🎯 • [00:01:36] Creating a culture where “bad ideas” are stepping stones to breakthroughs. 💬 • [00:01:50] Taking control of your narrative while balancing priorities like family and well-being. ❤️ Whether you’re an aspiring founder, a seasoned entrepreneur, or simply curious about the startup journey, this reel is packed with actionable takeaways and thought-provoking moments. 🎬✨ 🔔 Don’t forget to like, comment, and subscribe for more highlights and inspiration from ShitPitch! #Startups #Entrepreneurship #ShitPitch #KentRicheson #Innovation #ImperfectIdeas #StartupCulture

Get ready to laugh, learn, and be inspired! In this highlight reel, Kent Richeson, founder of ShitPitch, shares how he’s turning the traditional startup pitch on its head. From “pigeon messaging” to “silent karaoke,” ShitPitch challenges founders to think on their feet, show their personalities, and embrace creativity in ways no pitch deck ever could. 💡 What’s Inside: • Why investors are tired of the same old pitch decks 📊 • The magic of experimenting and letting vulnerability shine ✨ • Memorable moments like “pigeon messaging” and heartfelt takes on “silent karaoke” 🎭 • How ShitPitch encourages founders to embrace failure and be their authentic selves 🌟 • Stories of engaging pitch events from New York to beyond 🗽 If you’re a founder, investor, or just love hearing innovative ideas (and hilarious pitches), this is for YOU! 👉 Watch the full episode for even more insights and stories: https://youtu.be/vHUxZsDSm60 💬 What’s your favorite highlight? Let us know in the comments! #ShitPitch #StartupLife #FounderJourney #CreativePitches #Entrepreneurship #Innovation #StartupStories

🎙️ Welcome to another episode of the Startup Anthology Podcast! Join me and Kent Richeson, the entrepreneur behind ShitPitch, as we explore his innovative approach to startup pitches. Discover how he's reimagining the traditional pitch deck, emphasizing founder personality and vision. Kent also shares insights from his unique startup journey.

💡 What You’ll Learn in This Episode:

The story behind ShitPitch and its mission to highlight the person behind the pitch.

Why most traditional startup pitch events fall flat and how Kent’s approach changes the game.

The challenges of building Shit Pitch from scratch—experimenting with formats, engaging investors, and scaling globally.

How founders can improve their communication and self-awareness to build better teams and secure investments.

Why experimenting, being curious, and embracing vulnerability are keys to entrepreneurial success.

🎥 Plus, Kent talks about Shit Pitch’s plans for the future, including hosting events in over 20 locations next year, collaborating with Expert Dojo and Google HQ in India, and exploring possibilities for a TV show to bring the unique ShitPitch experience to a global audience.

📌 Key Highlights:

[00:01:35] The inspiration for Shit Pitch—showcasing founders’ authenticity.

[00:06:10] The evolution of pitch formats—how impromptu “bad ideas” reveal a founder’s true strengths.

[00:12:22] Silent karaoke, pigeon messaging, and the surprising depth behind humorous pitches.

[00:18:00] Expanding globally: From Utah to New Delhi and beyond.

[00:28:00] Sponsorship strategy and building lasting relationships with partners.

[00:37:16] Balancing startup life and family—Kent’s take on involving his kids in his entrepreneurial journey.

[00:45:53] Lessons learned: Being open to new ideas, taking risks, and learning through experimentation.

🔥 Whether you’re a founder, an aspiring entrepreneur, or just curious about the future of startups, this episode is packed with insights, humor, and inspiration. Don’t miss it!

👉 Connect with Kent Richeson and learn more about Shit Pitch:

Website: https://shitpitch.com/ LinkedIn [Kent Richeson]: https://www.linkedin.com/in/kentricheson/ LinkedIn [ShitPitch]: https://www.linkedin.com/company/shit-pitch/ Instagram [Kent Richeson]: @KentRicheson Instagram [ShitPitch]: @ShitPitch

👍 If you enjoyed this episode, don’t forget to like, comment, and subscribe for more startup stories and founder insights.

00:00 Welcome to Startup Anthology

00:52 Introducing Kent Richeson

01:35 The Concept of Shitpitch

05:26 Challenges and Early Stages

08:10 Experimenting with Pitch Formats

19:28 Expanding to New Territories

27:06 Sponsorship and Transparency

35:16 Balancing Family and Career

38:01 Mentorship and Lessons Learned

39:35 The Importance of Curiosity and Vulnerability

45:53 Taking Risks and Experimentation

48:59 Employee Mindset and Entrepreneurial Thinking

53:02 Advice to My Younger Self

55:43 Future Vision for ShitPitch

58:27 Connecting and Networking in Startups

01:03:00 Final Thoughts and How to Connect

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