Episodes

Jacob Zemon, a WSI-Certified business strategy consultant with expertise in AI & modern digital marketing, and the author of "Is Your Healthcare Practice Stuck?" Jacob draws on 20 years as a consultant at Accenture Strategy & in executive marketing roles at Publicis Groupe and Merck to equip his health & wellness clients to grow. In "Is Your Healthcare Practice Stuck?", Jacob explains the common marketing mistakes that hinder growth and introduces a practical strategic framework for success. ...

Jeff Heather founded North Light IT in 2000, as a boutique managed services provider in the Boston area that handles IT and cybersecurity for law and professional services firms with 30 or fewer employees-environments where every hour down is costly. North Light manages IT so clients can handle the work that actually pays. Jeff believes that IT done right should be accessible for smaller firms - support, strategy, and security. And, that IT should “stay out of the way – be vanilla and boring”. ...

Jim and Deanna Varney founded Wavelength Coffee Roasters in 2025 after his careers in engineering and design, and hers in education, and library science. Jim leads sourcing and roasting, while Deanna oversees operations. Partnering with innovative growers, they focus on bringing out the best in every bean. Wavelength uses all-electric, solar-powered air roasting for a clean, smooth flavor and packages coffee in reusable, recyclable steel containers to reduce waste and preserve freshness. Winn...

Sergiu Simmel guides founders, owners, CEOs of small-to-midsized businesses & their Leadership Teams on growing their business faster, easier and with more joy than they ever thought possible. After founding 3 start-ups and a consulting practice, he shifted his focus towards business coaching, becoming the first EOS Implementer in New England. In 2024, he immersed his work into the ever-changing world of Generative AI through partnerships with Humans+AI and WSI. Winning Business Radio is broa...

Mike Dwyer is the founder of Emplana Career, a purpose driven company making a difference in people's lives. It started when a friend asked him to look at a resume, and then more than the usual supportive critique, the conversation morphed into questions like, “Would it make sense for you to look at this or that direction?” That deepened his interest in workplace issues, how people navigate their careers, and a personal challenge to better prepare himself to help with the careers of others. Wi...

Since launching One 8 Solutions in 2001 and becoming a certified QuickBooks ProAdvisor, Jonathan developed a “client first” business attitude. Accounting and bookkeeping are core to the understanding of a business and Jonathan and his team conduct a detailed assessment, discovering what has significant impact to the success of the business. They are then able to provide information back to the client on a timely basis while providing meaningful knowledge of the “other half of the story.” Winni...

Erika Wasserman is a dynamic force in the world of financial transformation. With a finance degree from the Univ of Florida, a grad certificate in Financial Therapy from Kansas State and ten years at IBM, she brings a unique mix of corporate savvy and innovative thinking to financial wellness. Erika is the author of Conversations with Your Financial Therapist: Stories and Scripts to Grow Your Financial Mindset, reflecting her passion for making money talk both accessible and transformative. Wi...

Ray Pasquale is the President and CEO of Unified Office. He has spent the last 25+ years as an award-winning entrepreneurial technology professional within emerging technology companies, including DEC, Cascade Communications, Ascend Communications,...

Craig Brenner - CEO and co-founder of icognio - talks about their legal technology company delivering secure, on-premises AI solutions built exclusively for law firms. With decades of experience across technology, leadership, and enterprise systems, Craig has helped build and scale multiple companies serving high-trust, high-stakes environments. He founded icognio to address the security, governance, and adoption gaps he saw emerging as law firms rushed to adopt cloud-based AI tools. Winning Bu...

Returning guest John Gates, Pay Negotiation Expert, Keynote Speaker, and Best-Selling Author of “Act Your Wage”, and founder of The Crossroads: a proven, faith-aligned path that helps Christian corporate leaders launch their first consulting business in just 6 weeks. As a former head of global recruiting for multiple Fortune 500 companies, he trained hiring teams on how to negotiate - giving him rare, insider insight into what actually works. Winning Business Radio is broadcast live Mondays at ...

Steve DeVries has dedicated his career to transforming companies into high-performing, future-ready businesses. As a Certified Business and Executive Coach for 25+ years, he has worked with technology-based OEMs, manufacturers, & service providers to improve team performance and strategic execution. He specializes in equipping leaders with the tools and strategies to navigate complex challenges: developing people, improving financial management, & often preparing for organizational succession. ...

Reilly DiPlacido - Founder & CEO of Triumph HR - an HR consulting and recruiting firm helping growing businesses build strong teams, stay compliant, and create workplaces where people and performance thrive. She works closely with business owners and leadership to provide HR guidance from employee relations and compliance to talent strategy and leadership support. Reilly is passionate about simplifying HR so leaders can focus on growing their businesses and leading their teams with confidence. ...

Tony Pompeo is a business professional, entrepreneur, and 6-yr US Marine who has owned multiple businesses. He bought, managed and grew his longest-owned business, a distribution company, successfully steering it through the Great Recession and the Global Pandemic, ultimately selling the company to private equity. Tony received his MBA from Babson College. Because of his own experience running, growing and selling businesses, Tony enjoys guiding small business owners to reach their goals. Winni...

Lucky Papageorg, Exec. Dir. of the MA Auto Body Assoc. (MABA), advocates for independent collision repair professionals. He works closely with shop owners, policymakers and insurers on issues like labor rates, technician recruitment and training, repair quality & safety. Matthew Ciaschini, co-owner of Full Tilt Auto Body & Collision, serves as Pres. of MABA's Board of Directors. He brings hands-on experience and an owner perspective with a focus on strengthening independent auto body shops. Wi...

John Gates, Pay Negotiation Expert, Keynote Speaker and Best-Selling Author of “Act Your Wage”, joins Kevin to share his story. As a Fortune 500 Head of Recruiting, John has overseen more than 75,000 job offers during his 30-year career. As the creator of the Salary Coach Method John helps executives and job seekers confidently navigate offer conversations without risking the deal. His sessions blend sharp strategy with a calming, practical tone that clients love - and apply immediately. Winn...

Jennifer Killilea, Financial Advisor with Johnson Brunetti, discusses her focus on the unique needs of women. Jen has 20+ years specializing in retirement planning. She is dedicated to delivering personalized and comprehensive advice to clients. She takes pride in understanding each individual’s unique needs and creating customized retirement plans to achieve their goals. Jen presents at the firm’s Women-only Workshops where she creates a space specifically for women’s financial education. Winn...

Martin Lachance is the founder and CEO of Citara Systems, a Massachusetts IT services firm keeping businesses fast, secure, and frustration-free since 2001. With 20+ years in the industry, he’s driven a 97% client retention rate by cutting IT issues and delivering rapid support. Born in Canada and raised in the US, Martin earned accounting and finance degrees from Northeastern, worked at Delphi Internet in the early online era, and later led engineering at Toast before launching Citara. Winning...

Cruz Gamboa, MBA is a former GE Corporate Executive and a seasoned Scaling Up business coach with a passion for helping ambitious founders, CEOs and mid-market companies, who are ready to think beyond incremental progress, increase profits, boost valuation, and drive meaningful impact to 10x their value and reach. Cruz has lived in multiple countries and speaks 3 languages: Spanish, English, and Portuguese. He is the author of Drive From Within. Winning Business Radio is broadcast live Monday...

Returning guest Warren Rutherford brings decades of insight into executive leadership and strategic talent alignment. He specializes in executive search for private and family-owned businesses across the U.S. and internationally. His work goes far beyond recruitment, helping organizations reimagine their leadership teams in ways that drive long-term growth, cultural fit, and strategic execution, ensuring that leadership transitions align vision with the right talent to elevate performance. Wi...

Leslie Hassler founded Your Biz Rules, transforming small businesses into freedom-generating machines. She guides businesses toward predictable profits and sustainable growth via comprehensive business audits, her Profitable Growth Incubator program, private consulting, and Fractional CFO services. She equips them to conquer challenges, unlock unprecedented growth, and build a life of abundance and balance. Winning Business Radio is broadcast live Mondays at 4PM ET and Music on W4CY Radio (www....

In 1979, Mark Silverman was a student at Northeastern University. Needing tuition money and seeing that students needed help moving, he decided to become a mover - he purchased a small van with a credit card. Over time, the business became Mark’s sole focus. One Man and a Van became Mark’s Moving & Storage. Nearly 46 years later Mark is still looking for opportunities to help people. He created Mark’s Northeastern Furniture Foundation, TheStorageCompany.com and Massachusetts Portable Storage. ...

Matt Arnold, founder of architectural firm ArnoldAnd, has two decades working as an architect in greater Boston, most notably in a senior leader role. Matt has earned a reputation for masterfully blending modern design and sustainability features within historic homes and buildings. Modern Luxury Interiors Magazine recently named Matt one of its “Ones to Watch” class of 2025. He is a member of the BSA’s Residential Design Committee, the Boston Preservation Alliance and LevelUp Mastermind. Win...

Gregory Vetter, innovator & disruptor in the Clean Food Movement and author of "Undressed", founded Tessemae’s after being inspired by his mother’s homemade dressing recipe. Greg and his family, primarily brothers Matt & Brian, grew the...

Timothy Swords-executive coach, certified mindfulness teacher, principal of Mindful Leadership Executive Coaching. With decades as a financial services executive, CFO & management consultant with rigorous mindfulness training - incl. 2,000+ hours...