In this episode of The Thoughtful Entrepreneur, host Josh Elledge welcomes Wilson Zehr, Founder and CEO of Zairmail, for a deep exploration into why direct mail is still one of the most effective marketing channels in today’s digital-first world. Wilson draws from decades of experience—plus a surprising connection to competitive swimming—to illustrate how businesses can blend digital convenience with physical mail for unmatched engagement and ROI. This episode offers a practical, insightful guide for any leader looking to leverage direct mail to scale their business.

Wilson opens the conversation by comparing the discipline of competitive swimming to the discipline required to launch successful marketing campaigns. New swimmers must warm up, refine their technique, and focus on continuous improvement—principles that apply seamlessly to businesses exploring direct mail for the first time. He emphasizes the importance of starting with small, targeted campaigns and refining strategy over time.

The discussion then highlights how Zairmail’s platform blends the ease of digital workflows with the impact of physical mail. Businesses can upload documents, preview their mail in real time, and send campaigns with a single click. With next-day processing and a nationwide production network, Zairmail ensures speed, scalability, and reliability across every campaign.

Wilson also breaks down why direct mail continues to outperform expectations in 2024. From owning the “mail moment” to delivering strong ROI and enabling precise demographic targeting, physical mail creates a level of attention and trust that digital ads struggle to achieve. Whether using postcards, letters, snap packs, or self-mailers, choosing the right format can dramatically improve response rates and engagement.

Wilson Zehr is the Founder and CEO of Zairmail and a seasoned marketing expert with 26+ years of experience helping organizations execute high-impact direct mail campaigns. Wilson’s background in both technology and traditional media uniquely positions him to bridge the gap between digital tools and physical marketing performance.

Connect with Wilson on LinkedIn.

Zairmail is a leading direct mail platform that makes sending physical mail as simple as sending an email. With next-day processing, nationwide facilities, real-time previews, and data-driven targeting tools, Zairmail empowers businesses of all sizes to launch fast, reliable, and high-ROI direct mail campaigns.

• Zairmail Website
• Wilson Zehr LinkedIn Profile

• How swimming principles translate into better marketing execution
• Why direct mail continues to deliver high ROI in 2024
• The four main direct mail formats and when to use each
• How Zairmail blends digital workflows with physical mail for unmatched efficiency
• Expert tips on targeting, creative, testing, and integrating digital channels

Wilson Zehr reinforces that direct mail isn’t outdated—it’s a powerful, underutilized differentiator. By integrating digital...

In this episode of The Thoughtful Entrepreneur, host Josh Elledge welcomes Kristen Boss, Founder of Sondera, executive coach, keynote speaker, and host of The Kristen Boss Podcast. Kristen dives deep into the power of nervous system regulation, helping high achievers and leaders understand how to perform sustainably under pressure. Her approach bridges neuroscience, leadership, and emotional intelligence—offering strategies that empower professionals to thrive without burning out.

Kristen opens by revealing how intentional stillness, creativity, and mindful hobbies—like skiing or crafting—help her stay grounded. These moments of calm, she explains, are not indulgences but essential tools for recovery and innovation. High achievers often push through stress, but learning to slow down can enhance clarity and unlock creativity.

She also introduces the concept of stress types—fight, flight, and freeze—explaining how each reflects an automatic safety response that shapes our behavior in business and leadership. Recognizing these patterns allows leaders to manage reactivity, strengthen decision-making, and create more emotionally intelligent teams.

Throughout the conversation, Kristen emphasizes that sustainable high performance isn’t about pushing harder—it’s about learning to regulate your internal state. By calming your nervous system, you unlock greater focus, empathy, and resilience, enabling you to lead with intention rather than impulse.

About Kristen Boss

Kristen Boss is an executive coach, keynote speaker, and Founder of Sondera. A sought-after thought leader on high performance and nervous system intelligence, Kristen has built a global brand helping professionals and entrepreneurs master sustainable success. She is also the host of The Kristen Boss Podcast, where she explores leadership, mindset, and emotional resilience.

Connect with Kristen on LinkedIn.

About Sondera

Sondera is dedicated to helping leaders, teams, and organizations integrate nervous system intelligence into their approach to business and life. Through coaching, programs, and training, Sondera equips high achievers with the tools to perform at their best—without sacrificing wellbeing or fulfillment.

Links Mentioned in This Episode

• Sondera Wensite
• Kristen Boss on LinkedIn

• Why intentional stillness enhances creativity and performance
• How to identify your unique stress type (fight, flight, or freeze)
• Practical regulation tools—breathwork, micro-pauses, and reflection
• The role of empathy and curiosity in effective leadership
• Why nervous system intelligence is the foundation of sustainable growth

Kristen Boss reminds us that in a world obsessed with doing more, the real edge lies in being regulated, present, and self-aware. Nervous system intelligence isn’t just a wellness trend—it’s a leadership essential. By mastering emotional balance and responding rather than reacting, leaders can build trust, inspire teams, and sustain success in the long run.

In this episode, host Josh Elledge sits down with Mark Abbott, Founder and CEO of Ninety, for a deep dive into business operating systems, organizational culture, and the journey of scaling small and mid-sized companies. Mark—drawing on decades of experience in entrepreneurship, software development, coaching, and workplace culture—explains how leaders can build high-performing, resilient organizations by implementing the right frameworks at the right time. This blog breaks down the episode’s key insights and practical guidance to help business owners navigate their company’s growth stages with clarity and confidence.

Mark begins by explaining what a Business Operating System (BOS) truly is: a combination of tools, disciplines, and concepts that help organizations stay aligned, accountable, and scalable. He emphasizes that every company already has an operating system—whether intentional or accidental—and the goal is to consciously design one that matches the business’s stage of development. Popular frameworks like EOS, Scaling Up, and The Great Game of Business offer structured paths, but each company must adopt the tools most appropriate for their maturity level.

He breaks down the five stages of business development—Formation, Early Growth, Expansion, Maturity, and Legacy—and stresses that leaders must avoid skipping steps. For example, documenting every process too early is counterproductive; focusing instead on clarity, roles, and early team alignment yields better results. As businesses grow, they often mistake size for maturity, creating organizations that look impressive on the outside but lack foundational discipline internally.

Mark also highlights the importance of culture, trust, and forgiveness. High-performance organizations assume goodwill, set clear expectations, and use trust as a guiding principle—while also acknowledging that not all behaviors should be tolerated. He references research from Dr. Paul Zak to explain how trust chemically fuels team performance and why leaders must foster environments where transparency and accountability thrive. Platforms like Ninety help reinforce these practices by providing tools for meetings, scorecards, vision alignment, and process documentation, ensuring companies build habits that support long-term excellence.

Mark Abbott is the Founder and CEO of Ninety, a platform designed to help small and mid-sized businesses implement and sustain business operating systems. With decades of experience across entrepreneurship, leadership development, and organizational design, Mark has coached countless teams on building trust-based cultures and operational excellence. Connect with Mark on LinkedIn.

Ninety is a comprehensive software platform built to help organizations adopt, implement, and sustain a Business Operating System such as EOS. With tools for meetings, scorecards, rocks, issues, processes, and organizational clarity, Ninety equips leadership teams with everything they need to run a healthy, aligned, and scalable business. The platform supports both coach-led and self-directed implementations and includes extensive resources for long-term growth and accountability.

• Mark Abbott LinkedIn