In this episode of Leading in the Dark, host Nick Akers sits down with Simon Bailey, CEO of T.-Kartor, a leader in geospatial intelligence and civic mapping solutions supporting the Department of Defense and federal agencies. From humble beginnings as a survey grunt in Florida to running a global company supporting national security and transportation initiatives, Simon shares how he never chased leadership—but always rose when called. They discuss the evolution of geospatial tech, servant leadership, building trust in hybrid workplaces, and how empathy and transparency have shaped Simon’s leadership journey. An inspiring listen for anyone navigating leadership in complex, technical industries

In this episode of Leading in the Dark, Nick Akers is joined by Andrew Cohen, President of Moosylvania, a full-service creative agency with deep roots in family business. Andrew shares his unconventional path to leadership, navigating generational differences with his father, the agency's founder, and building a modern creative culture in a hybrid world. From experiential marketing to employee autonomy to launching an in-house brainstorm game, Andrew offers bold insights on running a business built on creativity, trust, and loyalty. If you've ever worked in a family business—or led through ambiguity—this episode will resonate.

Jared Peno, CEO and Managing Partner of Alliance Technologies, joins Leading In The Dark to share his evolution from hands-on engineer to people-first leader. In this candid conversation, Jared opens up about the challenges of overcoming self-doubt, the shift from micromanaging to empowering, and the intentional culture he’s built over 15 years of growth.

He also shares insight into navigating a competitive MSP market, integrating AI into service delivery, and why customer experience—not price—is still the ultimate differentiator.

Whether you're a founder, leader, or aspiring entrepreneur, this episode is packed with practical wisdom and real-world inspiration.

In this episode of Leading in the Dark, Nick Akers sits down with Taylor Perry, Managing Director of Acquisitions at Nova Stone Capital. They discuss Taylor's journey through investment banking, private equity, and entrepreneurship, and unpack Nova Stone's unique approach to supporting mid-career professionals through the search fund model. From scaling acquisitions across North America to providing operator-led ownership transitions, this conversation offers an inside look at the evolving world of entrepreneurship through acquisition (ETA).

In this episode of Leading in the Dark, Nick Akers reconnects with Alan Bulmer of Hawkins Watts in New Zealand. Alan shares his unconventional leadership journey—from food technologist to operations and sales leader—and how adversity and adaptability shaped his career. He dives into the cultural nuances of New Zealand’s workplace, the power of mentoring, and the company’s unique approach to hiring and developing talent. With wisdom rooted in a Māori proverb—"What is the most important thing in the world? It is people, it is people, it is people"—Alan offers a people-first perspective on leadership, growth, and legacy.

In this episode, Nick Akers, President & CEO of Inzo Techolgies, chats with August Felker, CEO and owner of Oberly Risk Strategies. August shares how he built a thriving career in insurance—starting with a traditional search fund acquisition—and how he’s grown Oberly to serve entrepreneurs across the country. They discuss the key points of insurance due diligence, hiring top sales talent, and creating a culture that delivers “fanatical customer service.” Whether you’re in ETA or simply looking for insights on leadership and growth, August’s story offers a valuable blueprint. Tune in for practical tips and candid lessons from a seasoned entrepreneur.

In the premiere episode of Leading in the Dark, host Nick Akers sits down with Brian Wilcox, a seasoned executive, former CFO/COO, and current board member, to discuss leadership, career transitions, and the lessons learned from decades of experience in corporate America. From GE’s intense culture under Jack Welch to scaling Fortitech into a global leader, Brian shares insights on leadership, strategic growth, and the transition from executive to board member. Tune in for a candid conversation about navigating business challenges, fostering a winning culture, and building meaningful professional relationships.

In this episode of Leading in the Dark, Nick Akers sits down with Brian Wolfe, former Kirkland & Ellis partner turned investor, educator, and entrepreneur. Brian shares lessons from his early career at Amazon, his unexpected leap into public education leadership, and his deep experience in private equity and ETA (Entrepreneurship Through Acquisition). They explore the realities of buying and scaling small businesses, the importance of relationship-driven leadership, and hard truths from his widely read paper on what ETA investors do and don't do.

Whether you're exploring search funds or just curious about strategic pivots in high-performance careers, this conversation is packed with practical insight and wisdom.