Episodes

In this solo episode of Retained Trust, host Karl Hughes takes a departure from his usual guest interviews to share a deeply personal and structured discussion on the 12 books that have most influenced his journey as an entrepreneur. Ranging from timeless classics to modern masterpieces, Karl reflects on how each book impacted his mindset, approach, and business strategies. From reshaping his understanding of productivity with The 4-Hour Work Week to conquering fear and embracing action with The...

In this episode of Retained Trust, host Karl Hughes speaks with Bob Tripathi, founder of Digital Sparx Marketing, about his fascinating journey through corporate roles, entrepreneurial pivots, and building a thriving marketing agency. Bob reflects on lessons learned from startups and large companies, discusses the importance of patience and adaptability, and shares how he turned challenges like the pandemic into opportunities with resourcefulness and grit. From digital marketing innovations to l...

In this episode of Retained Trust, host Karl Hughes sits down with Kyle Shevlin, founder of Agathist, a software development agency specializing in React and React Native. Kyle shares his journey from freelancing and full-time development roles to establishing Agathist, focusing on creating "good software by good people." He delves into the challenges of transitioning from solo work to agency leadership, his philosophy of balancing profitability with passion, and the practical strategies he empl...

In this episode of Retained Trust, host Karl Hughes sits down with George Zlatin, co-founder of Digital Third Coast, a Chicago-based SEO and digital marketing agency. George shares his unconventional entry into the digital marketing world, starting from launching an online dog boutique to becoming a respected SEO expert and business leader. They explore the evolution of SEO, including how Digital Third Coast has adapted to changing algorithms and AI-driven content strategies. George also reflect...

In this episode of Retained Trust, host Karl Hughes sits down with David Flanagan, founder of The Rawkode Academy and a veteran in developer advocacy. David shares his entrepreneurial journey, from building a niche YouTube channel to launching a unique business model centered on authentic, developer-focused content. They discuss the risks of leaving a stable job, how to monetize a passion project, and the complexities of balancing creativity with business strategy. David opens up about the strug...

In this episode of Retained Trust, host Karl Hughes sits down with Chris Gwinn, founder of Midwest CFO, a fractional CFO firm helping small businesses thrive by optimizing financial strategies and preparing for growth or exits. Chris shares his entrepreneurial journey, transitioning from Great Lakes Advisory to Midwest CFO, and the lessons learned along the way. The discussion explores common financial mistakes in small businesses, the importance of understanding gross margins, and the role of f...

In this episode of Retained Trust, host Karl Hughes speaks with Kon Kruglyak, founder of Candidate IQ, about the realities of starting a staffing business in challenging economic times. Kon shares his journey from corporate and financial recruiting to launching his own agency. Together, they explore the highs and lows of the recruiting industry, the strategies for building relationships with clients, and the importance of persistence in entrepreneurship. Kon offers insights into navigating tough...

In this episode of Retained Trust, host Karl Hughes sits down with Kurt Schnakenberg, co-founder of Chicago Brass and ADBM, to discuss his entrepreneurial journey and the innovative approaches he’s using to redefine his industries. From building a niche architectural consulting firm to launching ADBM—a pioneering agency offering ethical offshore staffing solutions—Kurt shares insights into scaling businesses, creating value through specialization, and maintaining authenticity in leadership. He e...

In this episode of Retained Trust, host Karl Hughes invites his business partner and close friend, Manuel Weiss, to share their dynamic journey of entrepreneurship, partnership, and building lasting businesses. From Manuel’s early days in Vienna founding a tech startup to Karl’s evolution from software engineer to content marketing entrepreneur, the duo discusses their shared experiences, lessons learned, and the foundational trust they’ve built along the way. They reveal the intricacies of star...

In this episode of Retained Trust, host Karl Hughes is joined by Jared Gibson, co-founder of Outworks, a marketing agency helping founders and executives build influence on LinkedIn. Jared shares his transition from a traditional sales role to entrepreneurship and discusses the journey of launching Outworks, from initial networking strategies to developing scalable, targeted content. They explore Jared’s approach to personal branding, tactics for leveraging LinkedIn’s algorithms, and the importa...

In this episode of Retained Trust, host Karl Hughes sits down with Shannon Beasley, founder of Acorn to Oak Strategies, to discuss her path from a biomedical engineering student to a local SEO agency owner. Shannon shares how her experiences in project management and sales eventually led her to build a business that focuses on empowering small and medium-sized enterprises (SMEs). Together, they delve into the nuances of local SEO, client acquisition, and the importance of personal growth as an e...

In this episode of Retained Trust, host Karl Hughes sits down with Sunny Shah, founder of SunnyCreators, a digital marketing and personal branding agency. At just 28, Sunny has built his name in Chicago’s entrepreneurship and creator space through authentic community-building efforts like his Chicago Dinner Club. The conversation explores Sunny’s path from academia and entrepreneurship education to leading a personal branding agency, highlighting his passion for social media, psychology, and mar...