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:

• Greg Heilers on LinkedIn: https://www.linkedin.com/in/kimley-cox-05baa61/
• Drive Talent: https://drivetalent.co/
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

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/karllhughes
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

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:

1. Greg Heilers on LinkedIn: https://www.linkedin.com/in/gregheilers/
2. Jolly SEO: https://jollyseo.com/
3. Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes
4. Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

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

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:

1. Peter Kang on LinkedIn: https://www.linkedin.com/in/peterkang34/
2. Barrel: https://www.barrelny.com/
3. Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes
4. Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

In this episode of Retained Trust, host Karl Hughes chats with Will Smith, host of Acquiring Minds and partner at Minds Capital. Will shares how his frustration with startup ideas led him to entrepreneurship through acquisition (ETA), and how a niche podcast turned into a full-time business and investment platform. The conversation explores the realities of buying and running small businesses, including the balance of humility and hubris, the hidden risks of acquisition, and the power of simply “getting in the game.” Will offers grounded advice for agency owners considering their next move—whether that's growth, sale, or acquisition.

Key Points From This Episode:

[00:00:00] Introduction to guest Will Smith and overview of Acquiring Minds

[00:02:08] Will reflects on turning podcasting into a full-time career

[00:04:17] His origin story: discovering ETA while seeking an entrepreneurial path

[00:07:41] What is ETA? Exposure, education, and the appeal of buying businesses

[00:10:16] Similarities between Acquiring Minds and Indie Hackers podcasts

[00:14:35] How the podcast opened doors and led to launching Minds Capital

[00:19:01] Why ideas, timing, and product-market fit are harder than they seem

[00:22:11] Hubris vs. humility: the mental balance needed when acquiring businesses

[00:27:10] Rethinking risk in ETA—especially with personal guarantees and SBA loans

[00:32:37] Why failures in ETA often hurt more than in zero-to-one entrepreneurship

[00:35:56] Top failure reason: seller fraud, and how to protect against it

[00:39:44] How ETA skips the gradual leveling-up process and hits harder, faster

[00:42:11] Should you buy small or go big? Pros, cons, and real-world implications

[00:46:16] The value of getting in the game—even with a small business

[00:49:57] Real-world examples: how being an owner opens doors to new deals

[00:52:56] Book recs: Buy Back Your Time by Dan Martell and American Nations

[00:55:47] Closing thoughts and what’s next for Will

Links:

• Will Smith on LinkedIn: https://www.linkedin.com/in/willsmithsf/
• Acquiring Minds: https://acquiringminds.co/
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

In this episode of Retained Trust, host Karl Hughes talks with Mushfiq Sarker, an experienced entrepreneur and founder of webacquisition.com. Mushfiq shares how he transitioned from flipping content websites to acquiring agencies and other online businesses. He reflects on lessons learned from managing over 200 acquisitions, the operational differences between flipping and holding, and how he identifies distressed agency assets with untapped potential. The conversation covers his approach to deal structuring, outsourcing, team management, and why high revenue but low margin businesses catch his attention. Mushfiq also dives into his preference for niche agencies, the importance of diversified revenue, and how to build resilient operations without over-hiring.

Key Points From This Episode:

[00:00:00] Mushfiq’s background in digital acquisitions since 2008

[00:03:06] Why he pursued a PhD despite already earning online

[00:05:24] Problems with too much VC funding and startup waste

[00:08:39] Importance of repetitions in small business acquisitions

[00:10:50] Managing multiple businesses with 80% efficiency and operators

[00:13:32] Building a portfolio around his strength: lead generation

[00:15:01] How Mushfiq handles personnel risk and team redundancy

[00:19:17] Slack-based escalation rules for client service issues

[00:20:58] Why he avoids structured operating systems like EOS

[00:22:01] Buying agencies: “core” vs. distressed “tack-on” models

[00:23:53] Structuring rev share and fixed-payment deals for dead agencies

[00:28:37] Buying high-revenue, low-margin agencies for profit optimization

[00:31:39] How Mushfiq restructures teams and P&Ls quickly

[00:34:21] What makes an agency attractive to a buyer like Mushfiq

[00:38:49] Only acquiring retainer-based, not one-off, service agencies

[00:40:14] Learning through early failures and SEO experience

[00:43:02] Why first-time buyers should start small or build something first

[00:45:32] Mushfiq’s media diet: podcasts, YouTube, and Twitter

Links:

• WebAcquisition: https://webacquisition.com
• Mushfiq Sarker on LinkedIn: https://www.linkedin.com/in/mushfiqsarker/
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

In this episode of Retained Trust, host Karl Hughes talks with Mark Bealin, founder of SearchLab, a Chicago-based digital marketing agency specializing in local SEO and PPC. Mark recounts his journey from side-hustle entrepreneur to leading a 50-person agency and dives into the pivotal decisions that shaped his company’s growth. He shares lessons learned from early failures, the power of niche specialization, the value of hiring for fit, and how becoming a father sparked a deeper entrepreneurial drive. The conversation wraps with Mark’s personal transformation, tackling health challenges through endurance training and building resilience.

Key Points From This Episode:

[00:00:00] Mark introduces SearchLab and its tight focus on local SEO and PPC.

[00:02:00] From side hustle to full-time: the agency's unofficial start in 2017.

[00:04:45] Leveraging legacy print media sales reps to scale early growth.

[00:07:40] Breaking through business plateaus and embracing high-stakes risks.

[00:13:24] How becoming a father reshaped Mark's drive and business focus.

[00:19:15] Lessons from a failed business partnership and realignment.

[00:23:02] From generalist to specialist: how focus led to faster growth.

[00:28:15] Improving profitability by cutting loss-leader services.

[00:32:48] Hiring industry-recognized leaders and building a strong leadership team.

[00:35:56] Navigating team culture shifts and turnover during the “Great Resignation.”

[00:38:24] Using assessments like Culture Index to scale hiring intentionally.

[00:41:40] Why customer-centered innovation drives SearchLab’s strategy.

[00:45:30] Understanding the “jobs to be done” theory in agency services.

[00:49:18] Facing market changes like AI and GEO with curiosity and customer insight.

[00:52:12] Mark's health wake-up call and transformation through endurance training.

Links:

• SearchLab: https://searchlabdigital.com/
• Mark Bealin on LinkedIn: https://www.linkedin.com/in/markbealin/
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com