On this episode of the Think Small Podcast, we sit down with Dennis Kao, serial entrepreneur and CEO of multiple technology and data-focused companies, to explore a career that began in a college garage and evolved into building, scaling, and exiting successful IT and managed service businesses. Dennis shares how he turned a passion for computers and gaming into Proactiv, a business that served healthcare, local government, and professional services clients for over a decade, eventually leading to a strategic exit.

He dives into the lessons learned from navigating economic downturns, focusing on vertical specialization, and staying true to his core competency in data and analytics. Dennis also discusses his next ventures, which harness AI and data governance to help businesses monetize their data while protecting it—positioning them for growth in the new industrial revolution. This conversation is a masterclass in disciplined focus, strategic pivots, and leading technology-driven businesses in complex, evolving industries.

Connect:

Website: https://proactive-info.com/

LinkedIn: https://cz.linkedin.com/in/denniskao1

In this episode of the Think Small podcast, we sit down with Frank McKeon, Chief Marketing Officer at NowCorp, for a wide-ranging conversation that begins on a personal note—discussing college visits and the challenges of navigating higher education decisions—before transitioning into the world of B2B finance. McKeon introduces NowCorp’s “revenue-on-demand” model, which helps professional services firms overcome cash flow gaps caused by delayed client payments. Unlike traditional accounts receivable factoring, NowCorp offers a flexible, no-commitment approach where businesses can selectively sell invoices to access funds quickly without long-term contracts, monthly minimums, or hidden fees. This model is particularly valuable for growing companies working with large clients who often extend payment timelines beyond agreed terms.

The conversation also explores McKeon’s career journey through telecom and fintech, along with his strategic approach to marketing in both challenging and high-growth environments. He emphasizes the importance of staying data-driven, avoiding reactive decision-making, and maintaining focus on core strengths rather than competitors. During periods of rapid growth, McKeon highlights the need for operational readiness, disciplined analysis, and continued investment in momentum rather than complacency. He closes with practical advice for business leaders: build strong teams, stay adaptable, and carefully evaluate financial solutions to ensure they align with long-term flexibility and growth goals.

Connect:

Website: https://nowcorp.com/

LinkedIn: https://www.linkedin.com/in/frankmckeon/

In this episode of the Think Small Podcast, we sit with Brian Waldron, CEO of Dort Financial Credit Union, about leading a purpose-driven financial institution focused on community impact and member success. Brian shares how Dort Financial grew from its automotive industry roots in Michigan into a $2.3 billion organization serving over 100,000 members, and explains what makes credit unions different—from their member-owned structure to their deep investment in local communities. He also discusses the organization’s expansion into Florida and how strategic growth aligns with serving members throughout different stages of life.

Brian reflects on his career journey, from a student-run credit union in college to leading teams through complex challenges, including navigating a major fraud crisis. He emphasizes the importance of putting people first—prioritizing employees to ultimately deliver better service to members—and highlights key leadership principles like authenticity, transparency, and resilience. The episode closes with his advice to leaders: embrace vulnerability, focus on culture, and remember that big dreams require bold moves.

Connect:

Website: https://dortonline.org/

LinkedIn: https://www.linkedin.com/in/brian-waldronmi/

In this episode of the Think Small podcast, we sit down with Beau Sorensen, COO of First Choice Home Health and Hospice, to explore his unconventional journey into healthcare and his 26-year rise within the organization. Starting in high school with an interest in medicine, Beau discovered a passion for home health and hospice care, eventually focusing on operations and leadership. He shares how the company navigates both growth and contraction by prioritizing people—offering compassionate offboarding during downturns and emphasizing cultural fit during expansion, especially through mergers and acquisitions.

Beau highlights how a human-centered philosophy drives everything from patient care to employee engagement, including bereavement support for families and long-term pediatric care. He also discusses the company’s forward-looking approach to technology, using AI and wearables to improve patient outcomes and operational efficiency without reducing staff. Reflecting on a major crisis where the company lost its entire medical records system, Beau underscores the power of transparency, teamwork, and trust—ultimately reinforcing his belief that trust is the most valuable asset any organization can build.

Connect:

Website: https://www.fchhh.com/

LinkedIn: https://www.linkedin.com/in/beausorensen

In this episode of the Think Small podcast, we sit down with Jack Terrill, Executive Director of the Wentworth Economic Development Corporation (WEDCO) in rural New Hampshire. Jack shares how WEDCO supports small and mid-sized businesses by providing gap financing, guidance, and access to capital for entrepreneurs who may not qualify for traditional bank loans. From helping launch niche ventures like goat farms and curated toy stores to supporting auto repair shops and tourism-driven businesses, WEDCO plays a critical role in strengthening the local economy through creative lending and hands-on advising.

The conversation dives into the unique challenges of operating in a seasonal, rural market—from managing cash flow during long winters to capitalizing on peak tourist seasons. Jack also discusses WEDCO’s evolving strategy, including expanding its funding sources, exploring equity partnerships, and ensuring long-term sustainability and impact. With a strong belief in building generational wealth through small business ownership, this episode highlights how community-focused investment and strategic support can create lasting economic growth.

Connect:

Website:

LinkedIn:

In this episode of the Think Small Podcast, we sit down with Kevin Lowrie, owner of Class 101, to discuss his unique journey from IT consulting and life coaching into the world of college and career readiness. Kevin shares how his passion for coaching and helping others navigate major life decisions ultimately led him to Class 101, a nationwide college planning organization focused on guiding students and families through the increasingly complex path to higher education. He reflects on the company’s origins, its structured yet personalized approach, and how having access to a nationwide network of advisors enhances the support he can provide to each student.

Kevin dives into the core of what Class 101 offers—far beyond test prep and applications—highlighting a comprehensive, multi-year strategy that includes academic planning, extracurricular development, essay coaching, and scholarship optimization. He emphasizes the importance of early exploration, building meaningful experiences, and aligning students’ goals with the right educational or career path, whether that includes a four-year college, trade school, or a gap year with purpose. Kevin also shares insights on empowering both students and parents throughout the process, the financial realities of higher education, and how intentional planning can lead to significant scholarship outcomes and long-term success.

Connect:

Website: https://www.class101.com/sandiaheightsnm/

LinkedIn: https://www.linkedin.com/in/kevinlowrie

On this episode of the Think Small Podcast, we sit down with Simon Kaye, President and CEO of Jaguar Freight Services, to explore his journey from a family legacy in transportation to building a global supply chain management company. Simon shares how Jaguar evolved from early track-and-trace tools into a full-service logistics provider, serving international clients across key trade lanes while focusing on niche verticals like health and beauty, medical devices, and consumer goods.

He also dives into navigating disruption—from COVID-19 to ongoing global supply chain challenges—by embracing a fully remote workforce and prioritizing company culture. Simon explains how transparency, employee well-being, and a disciplined focus on core competencies have driven long-term growth, and outlines his ambitious vision to scale the business 10x while maintaining strong employee and client relationships.

Connect:

Website: https://jaguarfreight.com/

LinkedIn: https://www.linkedin.com/in/simonmkaye/

In this episode of the Think Small Podcast, we’re joined by Joe Fannin, owner of Austin Elephant, a Texas-based residential services company built on grit, growth, and real-world lessons. Joe shares how he got his start in the industry—from simply needing a job to building a thriving business rooted in hands-on work, strong client relationships, and continuous learning. He opens up about early challenges like failed marketing efforts, financial risks, and the trial-and-error process of finding what actually works, while emphasizing the importance of customer fit and why “firing” the wrong clients can lead to better efficiency and profitability.

Joe also dives into the evolution of his business—from a one-man operation to a streamlined team focused on high-value, recurring clients—and the strategic rebrand from Fannin Professional Services to Austin Elephant. He explains the thinking behind the new identity, how it reflects the company’s values, and how he managed the transition without losing customer trust. Looking ahead, Joe shares his vision for sustainable growth, including expanding recurring services and strengthening relationships within his market.

Connect:

Website: www.AustinElefant.com

LinkedIn: https://www.linkedin.com/in/joseph-fannin-a134a673/

On this episode of the Think Small Podcast, we sit down with Heather Lee, Vice President and COO of the Effective Leadership Academy in Cleveland, Ohio, to explore how her organization is transforming leadership development for students and professionals alike. Heather shares how the Academy helps individuals develop their most valuable asset—themselves—through soft skills, communication, collaboration, and workforce readiness programs that span from middle school to corporate teams.

She dives into the unique challenges of the digital age and post-COVID world, emphasizing the importance of human connection and face-to-face interaction in an AI-driven environment. Heather also discusses how ELA has scaled its impact beyond Cleveland, leveraging hybrid learning, teacher collaboration, and tailored programs for organizations like the Cleveland Clinic, while maintaining a mission-driven approach to nonprofit growth.

This conversation is a masterclass in fostering essential leadership skills, bridging generational and technological gaps, and preparing the next generation of professionals to succeed in a rapidly evolving world.

Connect:

Website: https://www.effectivela.org/

LinkedIn: https://www.linkedin.com/in/heather-lee-55300550/

On this episode of the Think Small Podcast, we sit down with Cameron Boland, Chief Operating Officer of Keymark, to explore how a technology company rooted in document processing evolved into a leading AI-driven solutions provider. With a history dating back to 1996, Keymark has transformed from offering OCR software into deploying Intelligent Document Processing tools that help businesses streamline operations, improve efficiency, and realize measurable ROI.

Cameron shares how Keymark navigated periods of economic uncertainty—like the 2008 financial crisis—by leveraging long-standing customer relationships, and how the current AI boom is driving rapid growth and new opportunities, including strategic acquisitions and international expansion. From competing with DIY AI initiatives to ensuring human-centered technical support, Cameron highlights the importance of adaptability, building trust, and applying technology strategically to solve the right business problems. This conversation is a masterclass in leading a growth-focused, people-first tech company in the midst of a generational industrial revolution.

Connect:

Website: https://www.keymarkinc.com/

LinkedIn: https://www.linkedin.com/in/cameron-boland-a1b7791/