1d ago

Building Relationships That Drive Business: Dr. Jeremy Weisz on Podcasting and Networking

In this episode of Retained Trust, host Karl Hughes speaks with Dr. Jeremy Weisz about using podcasting to build relationships, strengthen trust, and create business opportunities. Jeremy shares how his path from chiropractic to podcasting led to lasting professional relationships and eventually to building Rise25. They discuss why guest relationships can matter more than download numbers, how podcasts can shorten sales cycles, and ways businesses can use interviews to strengthen referral and strategic partnerships. Jeremy also explains his systems for staying in touch with contacts, choosing podcast guests, and using every episode as an intentional follow-up tool. Key Points From This Episode: [00:00:00] Karl welcomes Dr. Jeremy [00:01:12] Jeremy’s path from biochemistry and chiropractic to podcasting and relationship building [00:09:06] Doubling down on podcasting by increasing the number of conversations each week [00:10:38] Why relationship-focused businesses understood the value of podcasting early [00:14:38] Focusing on controllable relationships instead of podcast download numbers [00:15:56] Reaching out to lesser-known founders and executives for memorable conversations [00:17:36] Stories about connecting with Steve Wozniak, Savannah James, and other notable people [00:20:27] How Jeremy helped connect Tony Horton with Steve Nash through shared interests [00:24:35] Why entrepreneurs should be willing to ask and accept the possibility of rejection [00:25:51] How podcasts can build trust and shorten long sales cycles [00:28:37] Using a podcast to strengthen relationships with partners, clients, and referral sources [00:32:14] Why podcasting works especially well for high-trust agency sales [00:33:38] Building authority by sharing expertise and ideas through podcast content [00:35:05] Jeremy’s criteria for selecting guests and focusing on strategic relationships [00:37:58] Organizing a broader podcast into focused series for different audiences [00:38:57] Why a podcast name can stay broad while outreach and messaging remain specific [00:40:46] Jeremy’s daily habit for reconnecting with people in his network [00:42:23] Using CRM pipelines, accountability, and scheduled follow-ups to maintain relationships [00:43:52] Treating each podcast episode as a structured follow-up system [00:46:55] Building networking habits into the podcasting process [00:47:30] Using a simple framework to consistently mention and support important relationships Links: Dr. Jeremy Weisz on LinkedIn: https://www.linkedin.com/in/drweisz/Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughesRise25: https://rise25.com/Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

Sep 8

Building a Podcast Portfolio: Karl Hughes and Manuel Weiss on Acquisitions, Integration, and Growth

In this episode of Retained Trust, host Karl Hughes welcomes back his business partner, Manuel Weiss, for a personal and business update. Manuel shares his move from Vienna back to the U.S., while he and Karl explain why they are shifting their attention toward the podcasting industry. They discuss stepping back from Draft.dev, acquiring Sundial Media and Rise25, and their approach to integrating teams while preserving brands that serve distinct parts of the market. Karl and Manuel also examine how their roles are changing as they focus more on acquisitions, culture, delegation, and building repeatable integration systems. They close with their plans to grow through additional acquisitions, maintain healthy margins, expand services, and continue improving how their portfolio of podcast businesses operates. Key Points From This Episode: [00:00:00] Karl welcomes Manuel back to Retained Trust after the summer break [00:00:36] Manuel shares his move from Vienna back to the U.S. after receiving his green card [00:02:04] How living in the U.S. could create a more regulated workday for Manuel [00:02:38] Karl and Manuel step back from Draft.dev after bringing on a CEO [00:03:18] Why the partners decided to focus more heavily on the podcasting industry [00:05:55] Comparing the stability of the podcast business with the fluctuations of tech content marketing [00:07:40] Why owner-led podcast production companies are creating acquisition opportunities [00:08:29] Karl's approach to building relationships with potential buyers and sellers before an exit [00:10:12] Why integration and culture matter after an acquisition closes [00:10:52] Deciding when to preserve an acquired company's brand instead of merging it [00:12:56] How timing helped bring Sundial Media and Adam Hendricks into the business [00:13:28] Manuel reflects on the trust behind the Sundial acquisition and Adam's fit with the team [00:14:37] Why adding experienced operational leadership became increasingly important [00:16:53] Adam's new role as director of operations and the acquisition of Rise25 [00:17:48] Manuel explains the Rise25 due diligence process and signing the deal just after moving to the U.S. [00:19:33] How Karl's relationship with Rise25's founders developed into an acquisition opportunity [00:21:17] Why Jeremy Weiss's podcasting experience and relationship-based sales approach stood out [00:22:23] Differences between the Rise25 and Podcast Consultant team structures [00:24:56] Why different approaches to running a profitable business can all work [00:27:06] Building an operating layer above individual brands and developing repeatable integration systems [00:28:55] Lessons from Pilot's acquisition strategy about culture, consistency, and customer outcomes [00:32:33] Why Karl and Manuel plan to preserve separate brands when it makes sense [00:34:33] Using multiple brands to serve different segments of the business podcast market [00:35:58] How Rise25 and The Podcast Consultant serve different types of podcast customers [00:38:16] Creating reliable service and continuity for clients across a larger organization [00:39:15] How Karl and Manuel's responsibilities have changed as they step away from day-to-day operations [00:39:37] Manuel shifts from implementing process improvements himself to enabling team members [00:41:26] Karl spends less time on sales and more time supporting teams and sourcing acquisitions [00:43:19] Creating opportunities for others by stepping away from roles the owners do not want to perform [00:44:45] Building momentum while staying disciplined about which acquisition opportunities to pursue [00:46:29] Plans to acquire $1 million to $3 million in podcast production revenue per year [00:47:59] Manuel's goals around acquisition experience, delegation, and making more use of his U.S. location [00:49:27] Karl previews more Retained Trust episodes focused on podcasting and lessons for agency owners Links: Manuel Weiss on LinkedIn: https://www.linkedin.com/in/manuelweiss1986/ Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughesRise25: https://rise25.com/ Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

Episode 61 Trailer

The Real Story of Entrepreneurship | Trailer

Building a company is rarely the clean success story you hear after the fact. On Retained Trust, Karl Hughes sits down with founders and entrepreneurs to unpack what actually happens behind the scenes — the breakthroughs, the mistakes, the uncertainty, the painful lows, and the lessons that only come from building something yourself. These are candid conversations about entrepreneurship without the highlight-reel filter. Guests share the decisions that shaped their companies, the moments that tested them, and what they learned along the way. If you’re building a business, thinking about starting one, or simply want to understand what entrepreneurship really looks like, subscribe and join us for new conversations on Retained Trust. Links: Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughesProduction and editing by The Podcast Consultant: https://thepodcastconsultant.com

Apr 7

Hiring Leaders Without a Playbook: Kimley Cox on Talent Strategy

In this episode of Retained Trust, host Karl Hughes speaks with Kimley Cox, founder of Drive Talent, a retained search firm specializing in precision manufacturing. Kimley shares her journey from decades in recruiting to launching her own firm and refining a niche focus. The conversation examines how specialization builds trust, why many founders struggle to hire senior leaders, and how to evaluate candidates beyond resumes. Kimley also outlines practical hiring strategies, from proactive recruiting to structured assessments, while emphasizing culture fit, adaptability, and self-awareness as critical traits for long-term success. Key Points From This Episode: [00:00:00] Introduction to the podcast and focus on building and scaling agencies. [00:01:34] Kimley Cox’s background and founding of Drive Talent in precision manufacturing. [00:02:29] Transition from psychology to recruiting and early career journey. [00:04:44] Experience co-founding a recruiting firm and lessons from rapid growth. [00:06:39] Early challenges at Drive Talent, including pandemic-related business loss. [00:07:49] Importance of niching down and being known for a specific expertise. [00:08:55] How understanding industry language builds trust and improves sales. [00:10:31] Talent shortages in manufacturing and the impact of workforce retirement. [00:11:57] Proactive recruiting and building relationships before hiring needs arise. [00:13:00] Pitfalls of overly detailed job descriptions and the “perfect candidate” trap. [00:15:02] Evaluating leadership candidates based on culture, values, and adaptability. [00:16:07] Using a consultative approach to define the right role before hiring. [00:18:00] Overcoming founder insecurity when hiring more experienced leaders. [00:19:35] Using case studies and practical exercises to assess candidates objectively. [00:22:07] Leveraging assessments like StrengthsFinder to evaluate team fit. [00:23:30] “Journey” interview method to uncover candidate decision-making and character. [00:25:15] Importance of adaptability and accountability in leadership roles. [00:27:30] Attracting top talent to small businesses through vision and impact. [00:30:24] Red flags in candidates, including inconsistency and lack of self-awareness. [00:33:48] Balancing intuition with structured hiring processes. [00:36:58] Effective hiring strategies, including proactive outreach and referrals. [00:38:30] Keeping interview processes efficient to secure top candidates. [00:40:25] Using exploratory conversations to refine job requirements and attract talent. [00:44:55] Book recommendations and personal development influences. [00:46:59] Where to connect with Kimley Cox and learn more about Drive Talent. Links: Kimley Cox on LinkedIn: https://www.linkedin.com/in/kimley-cox-05baa61/Drive Talent: https://drivetalent.co/Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughesProduction and editing by The Podcast Consultant: https://thepodcastconsultant.com

Mar 24

The Best Advice on Agency Sales & Growth (From 25+ Founders)

In this special episode of Retained Trust, host Karl Hughes distills lessons from dozens of conversations with agency founders, consultants, and acquirers into a focused breakdown of what drives agency growth. The discussion covers the importance of maintaining a consistent sales pipeline, the impact of niching down, and why founders must take ownership of sales early on. Karl also examines the realities of inbound and outbound marketing, the risks of relying too heavily on referrals, and how pricing decisions affect profitability. The episode highlights practical approaches to building momentum, standing out in a crowded market, and creating a business that can scale beyond the founder. Key Points From This Episode: [00:00:00] Introduction [00:01:14] Pipeline as the foundation of agency growth and the risks of neglecting business development [00:01:30] How founders get stuck in delivery work and allow their pipeline to dry up [00:02:18] The importance of consistent sales effort and maintaining momentum [00:02:55] Relationship between close rates and required pipeline volume [00:03:05] Why niching down leads to clearer positioning, easier sales, and faster growth [00:03:56] Building authority by becoming highly specialized in a defined niche [00:04:40] The trap of offering broad services and staying stuck in client delivery [00:05:53] Clear positioning and messaging as a driver of referrals and recognition [00:07:01] Founders transitioning into sales roles regardless of original skillset [00:07:26] Why founders must learn sales before hiring dedicated salespeople [00:08:42] Common mistake of pitching too early instead of listening to prospects [00:09:48] The reality of inbound marketing requiring long-term consistency [00:10:39] Content creation as both a marketing channel and a way to refine thinking [00:10:56] The “momentum trap” of inconsistent content and marketing efforts [00:11:16] Marketing timelines and the challenge of committing long enough to see results [00:12:30] Outbound sales as a faster but often underutilized growth lever [00:12:33] Starting small with outbound and building consistency over time [00:12:57] Importance of understanding target customers and speaking their language [00:13:52] Multi-threading outreach within organizations to improve conversion [00:14:09] Managing long sales cycles by continuing conversations without pressure [00:14:30] Benefits and risks of relying heavily on referrals for growth [00:15:44] Why referral-only growth limits scalability and reduces business value [00:16:36] Pricing as a lever for growth and the impact of raising rates [00:17:59] Risks of over-customizing services and eroding margins [00:18:21] Negative economies of scale in agencies and increasing complexity with growth [00:18:43] Investing more in marketing to support long-term growth [00:18:57] Standing out in a crowded agency market through insight and differentiation [00:20:41] Leveraging authenticity and personality as a competitive advantage [00:21:31] Core takeaway: never stop selling, focus your niche, and build a scalable business Links: Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughesProduction and editing by The Podcast Consultant: https://thepodcastconsultant.com

Mar 10

Greg Heilers on Productizing SEO Services and Surviving the AI Shift

In this episode of Retained Trust, host Karl Hughes speaks with Greg Heilers, co-founder of Jolly SEO, an agency focused on earned link building and media placements. Greg shares his unconventional entrepreneurial journey, from volunteering around the world to launching multiple agencies and eventually building Jolly SEO into a productized service. The conversation examines lessons learned from early business failures, the value of partnerships, and the challenges of running service businesses through rapid technological change. Karl and Greg also analyze how generative AI is reshaping SEO, content marketing, and outreach—affecting workflows, team structures, and the broader digital marketing ecosystem. Key Points From This Episode: [00:00:00] Introduction to the Retained Trust podcast and guest Greg Heilers of Jolly SEO. [00:00:49] Greg explains Jolly SEO’s focus on earned link building and shares why he lives in China. [00:01:38] Greg’s entrepreneurial origin story, including volunteering abroad and starting his first agency. [00:03:43] Lessons from failed ventures, including attempts at software and early agency struggles. [00:05:56] Why productizing services helped Jolly SEO manage client expectations and avoid revision-heavy work. [00:07:45] How Jolly SEO connects clients with journalists and media outlets through earned media placements. [00:09:50] Overview of link building, ghostwriting debates, and the role of media mentions in SEO. [00:11:59] The volatility of marketing agencies and how external trends shape their growth cycles. [00:13:02] Greg shares tactical and emotional strategies for managing the ups and downs of entrepreneurship. [00:17:13] The benefits and challenges of running a company with a long-term business partner. [00:20:18] Greg’s side projects, including a HARO course and exploring acquisitions of traditional businesses. [00:24:52] How generative AI has changed workflows, delivery timelines, and pricing in agency services. [00:25:38] Internal experimentation with AI at Jolly SEO and the cost savings achieved through automation. [00:29:16] The leadership challenges of introducing AI to teams and helping employees adapt to new tools. [00:32:28] The emotional difficulty of workforce reductions and the human side of running a business. [00:36:17] How AI-generated content and mass outreach are making high-quality media placements harder. [00:38:26] The ongoing arms race between spam filters and automated outreach tools. [00:39:25] Discussion on AI detection tools, false positives, and challenges faced by non-native English writers. [00:41:45] Whether AI writing has reached a plateau or will soon match high-quality human content. [00:43:11] The future of long-form content and the rise of AI-generated summaries. [00:45:45] Reflections on technology’s impact on attention spans and digital media consumption. [00:47:09] Book recommendations including Think and Grow Rich, Who Not How, and Atomic Habits. [00:49:06] Karl shares a recommendation: The Top Five Regrets of the Dying and its impact on perspective. [00:51:43] Where to connect with Greg Heilers and learn more about Jolly SEO. Links: Greg Heilers on LinkedIn: https://www.linkedin.com/in/gregheilers/ Jolly SEO: https://jollyseo.com/ Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

Feb 24

From Agency Owner to Fund Investor: Grant Hensel on Buying Enduring Businesses

In this episode of Retained Trust, host Karl Hughes speaks with Grant Hensel, founder of Nonprofit Megaphone and managing partner at Entrepreneur Capital. Grant shares how he built a highly specialized agency serving nonprofits through the Google Ad Grant program, why niche focus and EOS transformed the business, and how he transitioned into acquiring and investing in small, enduring companies. They examine entrepreneurship through acquisition, common mistakes buyers make, and what agency owners often overlook when scaling or preparing for a sale. Key Points From This Episode: [00:00:00] Grant’s entrepreneurial journey and building Nonprofit Megaphone into a 60+ person niche agency. [00:03:00] Why specialization and claiming “best in the world” positioning changed everything. [00:03:34] Implementing EOS and shifting from working in the business to improving the machine. [00:04:28] Hiring sales leadership early due to constraints and building process from the start. [00:06:13] The simple survey that validated the Google Ad Grant market opportunity. [00:09:51] Market size realities, customer lifetime value, and expanding services strategically. [00:13:13] Founder strengths, hiring great people, and not getting in their way. [00:17:43] Transitioning from agency operator to buyer and investor in small businesses. [00:20:43] Traditional vs. self-funded search funds explained. [00:23:40] Launching Entrepreneur Capital and forming a fund to invest in acquisitions. [00:26:30] Why investing in operators beat acquiring everything personally. [00:30:04] Types of businesses they invest in, from tombstone engraving to industrial distribution. [00:33:31] Working capital mistakes and why cash at close is critical. [00:34:34] Risk factors in acquisitions: family involvement, customer concentration, and capital expenditures. [00:37:25] The realities of adjusted EBITDA and questionable add-backs. [00:42:28] Entrepreneurship, work habits, and setting boundaries with a weekly Sabbath. [00:44:45] Book recommendations: The Goal and other works on Theory of Constraints. Links: Grant Hensel on LinkedIn: https://www.linkedin.com/in/granthensel Nonprofit Megaphone: https://nonprofitmegaphone.com/ Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

Feb 10

Building Barrel Holdings: Peter Kang on Scaling and Exiting Agencies

In this episode of Retained Trust, host Karl Hughes speaks with Peter Kang, co-founder of Barrel and Barrel Holdings. Peter shares his 18-year journey in building a digital agency from the ground up, navigating the shift from generalist to e-commerce specialist, and eventually stepping away from daily operations. The conversation explores strategies behind launching new agencies, acquiring others, and managing leadership transitions. Peter offers grounded insights on financial structure, long-term sales planning, and why he believes in both holding and exiting businesses. Tune in for a tactical and honest discussion on what it takes to scale service businesses in a fast-evolving landscape. Key Points From This Episode: [00:00:00] Karl introduces Peter Kang [00:00:45] Peter shares how Barrel began and evolved into a portfolio of agencies. [00:03:54] How a niche "chose" them and why they pivoted toward e-commerce and Shopify. [00:07:20] The importance of choosing scalable niches and avoiding red oceans. [00:08:50] Lessons learned from W2-heavy hiring models and adopting a flexible team structure. [00:13:40] How different acquisition strategies influence cultural and staffing decisions. [00:15:27] Mistakes from the early Barrel years and how those lessons shaped BX Studio. [00:18:04] Why agency founders underinvest in sales and marketing—and how to fix it. [00:21:52] Peter’s transition out of Barrel and grooming internal leadership to succeed him. [00:26:11] Why downturns can be healthy tests for new leadership. [00:27:23] Experiences with hiring CEOs from outside the organization. [00:31:07] How Peter and his co-founder formed Barrel Holdings and adapted their strategy. [00:38:11] Platform risk, shifting tech trends, and how that shapes agency acquisition timelines. [00:39:37] What makes a small agency attractive to a buyer like Barrel Holdings. [00:43:33] Approaching seller expectations and early-stage valuation talks. [00:47:04] Peter’s structured system for staying in touch and networking consistently. [00:51:40] The book that helped Peter reshape his time horizon: 10x Is Easier Than 2x. [00:53:05] Final thoughts on intentionality, long-term planning, and Peter’s latest content. Links: Peter Kang on LinkedIn: https://www.linkedin.com/in/peterkang34/Barrel: https://www.barrelny.com/Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughesProduction and editing by The Podcast Consultant: https://thepodcastconsultant.com

Retained Trust

Building Relationships That Drive Business: Dr. Jeremy Weisz on Podcasting and Networking

Building a Podcast Portfolio: Karl Hughes and Manuel Weiss on Acquisitions, Integration, and Growth

The Real Story of Entrepreneurship | Trailer

Hiring Leaders Without a Playbook: Kimley Cox on Talent Strategy

The Best Advice on Agency Sales & Growth (From 25+ Founders)

Greg Heilers on Productizing SEO Services and Surviving the AI Shift

From Agency Owner to Fund Investor: Grant Hensel on Buying Enduring Businesses

Building Barrel Holdings: Peter Kang on Scaling and Exiting Agencies

Trailer

The Real Story of Entrepreneurship | Trailer

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Retained Trust

Episodes

Building Relationships That Drive Business: Dr. Jeremy Weisz on Podcasting and Networking

Building a Podcast Portfolio: Karl Hughes and Manuel Weiss on Acquisitions, Integration, and Growth

The Real Story of Entrepreneurship | Trailer

Hiring Leaders Without a Playbook: Kimley Cox on Talent Strategy

The Best Advice on Agency Sales & Growth (From 25+ Founders)

Greg Heilers on Productizing SEO Services and Surviving the AI Shift

From Agency Owner to Fund Investor: Grant Hensel on Buying Enduring Businesses

Building Barrel Holdings: Peter Kang on Scaling and Exiting Agencies

Trailer

About

Information