In episode 143, I dig into one of the most underestimated risks in agency ownership: the legal blind spots that quietly cost agencies millions over time.

From contracts and scope creep to client disputes, IP ownership, and liability exposure, we unpack where agencies unknowingly put themselves at risk — and why most don’t realize it until it’s too late.

This conversation is a must-listen for agency owners who want to protect what they’ve built, reduce unnecessary exposure, and stop treating legal as an afterthought instead of a growth safeguard.

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Sharon Toerek is Founder of Toerek Law (doing business in the agency world as Legal + Creative), where she focuses her national law practice on helping advertising, marketing, communications, and creative agencies protect their assets and turn their ideas into revenue.

Sharon provides proactive, strategic counsel to communications, marketing, advertising, digital, and creative agencies on legal and business issues they face continually in their work, including:

Sharon is an approved participant on the 4A's Legal Consultants Panel and a member of the 4A’s Expert Network. She has also served as President of the American Ad Federation (AAF) Cleveland and has been elected to AAF Cleveland’s Hall of Fame.

In addition to her Firm’s work representing U.S. independent agencies, Sharon

Contact Sharon on LinkedIn or on their website.

In episode 142, I sit down with Amy Maxwell, founder and creative director of Maxwell Design, to talk about the real tension small creative shops face: how do you grow without sacrificing the craft that made you successful in the first place?

We dig into what it looks like to evolve from “hands-on designer” to “agency leader,” how to protect quality as you add capacity, and how to make smart choices about clients, process, and scope so growth doesn’t turn into chaos. If you want to scale with intention (and still love the work), this one’s for you.

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Amy—Creative Director + Founder of Maxwell Design—has spent the last two decades helping businesses look their best. She’s an award-winning designer with a knack for reading minds and creating delightful visual experiences. Her solution-focused approach makes her someone you’ll want in any room. And her small (but mighty) team comes with some major design chops.

Contact Amy on LinkedIn or on their website.

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In episode 141, I sit down with Melissa and Meredith, the hosts of the Agency Darlings podcast and longtime agency operators, to unpack why so many agency owners feel burned out, stuck, or disillusioned by the traditional agency growth advice that’s been circulating for decades.

We talk candidly about the “bro playbook” — hustle culture, ego-driven leadership, top-down decision making, and growth at all costs — and why it often leads to unhealthy teams, poor margins, and miserable owners. Melissa and Meredith share what they’ve learned from years inside agencies about what actually drives sustainable growth: emotional intelligence, clear communication, strong operations, and leadership that prioritizes people alongside profit.

This episode is a refreshing, grounded look at agency leadership through a more human lens — one that challenges outdated norms and offers agency owners permission to build businesses that align with who they actually are.

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• Why the traditional agency “bro playbook” is failing modern agencies

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00:00 Why the traditional agency playbook feels broken

Each with over 15 years of experience in the agency space and deep-rooted connections within the industry, Melissa and Meredith bring actionable insights, expert advice, and candid conversations that challenge the conventional, masculine-driven approaches to agency growth.

Contact Meredith & Melissa:

www.agencydarlings.com

https://bit.ly/MWDarlings

https://waverlyave.com

https://instagram.com/waverlyave.co

https://www.lecheile.co/contact

https://www.instagram.com/lecheile.co/

In episode 140, I sit down with Michael Janda—agency founder, bestselling author, and one of the most respected voices helping creatives master the business side of creativity. Michael built and sold Riser, worked with giants like Disney and Google, and later led creative teams at Fox before dedicating his career to teaching creatives how to price, position, and run their businesses without burning out.

We dig into the mental and operational “growing up” that every creative eventually faces: getting past portfolio thinking, charging confidently, understanding value, eliminating chaos, and building a more peaceful (and profitable) creative life. Michael’s straight-talk wisdom hits every agency owner exactly where they need it—no fluff, no ego, just clarity.

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Michael Janda is an award-winning creative director, agency founder, and bestselling author.

He built the creative agency Riser with clients like Disney, Google, Warner Bros., and ABC, then sold the business after 13 successful years. Before that, he served as a creative director at Fox. Michael

is the author of Burn Your Portfolio and The Psychology of Graphic Design Pricing. Today, he shares practical, no-fluff strategies to help creative professionals master business, pricing, and growth.

Connect with Michael through his Community, Instagram, YouTube, LinkedIn, Website, or explore his Courses.

In episode 139, I sit down with Melanie Chandruang, founder of WeConsult and a strategic operations partner for creative agencies. Melanie has spent the last seven years helping agencies tighten up their financials, streamline workflows, and build stronger leadership teams—while also navigating two maternity leaves, a cross-country move, and re-entering the industry in one of its toughest seasons.

We dig into how she rebuilt WeConsult after stepping away to have kids, what’s changed in the agency landscape since 2023, and why she’s now staying higher-level as a fractional ops leader instead of getting buried in implementation. Melanie breaks down what healthy leadership actually looks like, why so many founders remain the bottleneck even after hiring “senior” people, and how clear ownership, scorecards, and trust change everything.

We also get tactical: what she looks for first in the financials, the operational metrics that matter most, and why agencies without documented processes are struggling the most with AI adoption. We wrap by talking about leading through uncertainty, avoiding burnout, and the simple practice Melanie uses to remind herself of the value she’s creating—plus her very 90s go-to karaoke song.

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Melanie Chandruang is the Founder of WeConsult and a Strategic Operations Partner for creative agencies. With over 15 years in the industry, she helps agency owners boost profits, streamline operations, and move big initiatives forward so they can focus on growth and what matters most.

Connect with Melanie on their website.

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In episode 138, I sit down with Jordan Snider, co-founder and CTO of Token Creative Services, to break down the real impact of integrating Ignition App into their agency operations. Jordan shares how Token went from scattered proposals, manual invoices, and nearly $40k in aging AR to a streamlined, single-system workflow that clients actually appreciated.

We dig into the operational before/after: centralized proposals and agreements, automated billing, faster close rates, clearer scope definition, easier upsells and renewals, and the elimination of unbilled “mystery hours.” Jordan also talks about forecasting clarity — and why dashboards that tie proposals, renewals, and revenue projections together are a game changer for decision-making.

This episode is a grounded look at what happens when an agency stops tolerating a duct-taped sales and billing process and finally upgrades the operational spine of the business.

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Jordan Snider is the Co-Founder and CTOof Token Creative Services, a full-service digital marketing and creative agency based in Kitchener-Waterloo. With a background in full-stack software engineering, Jordan bridges the gap between technical development and creative marketing. He has contributed personal reflections to platforms supporting victims of family violence, discussing the unique stressors faced by newcomers and the importance of community support systems.

His work reflects a blend of technical precision and a commitment to social impact, aligning with Token Creative’s mission to support businesses making positive environmental or social changes.

Connect with Jordan on their website, or learn more about Ignition here.

In episode 137, I sit down with Jennifer Spire, Partner and CEO of Preston Spire — a 75-year-old agency that’s somehow still pushing boundaries while many newer shops flame out. Jennifer shares how she modernized a legacy company without losing the cultural DNA that kept it alive for three-quarters of a century. We get into leadership transitions, building a values-driven agency, navigating generational shifts in talent, and how she’s shaping the next era of a Midwest powerhouse.

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Jennifer Spire is partner and CEO at Preston Spire, an Ad Age Best Place to Work and Midwest Small Agency of the Year. She is an accomplished agency leader with over 25 years of experience in both consumer and B2B marketing for just about every industry out there. At Preston Spire, Jennifer has played the leading role in reshaping the framework that defines the agency, focused on a strong vision, values and purpose. She has been a speaker at dozens of local and national conferences, has authored articles and thought pieces on various marketing subjects, and has been a board member of several nonprofit organizations. Jennifer was an east coast native before calling Minneapolis home. She was an NCGA gymnast and a gymnastics coach, who also had advertising in her blood, thanks to her grandfather being one of the founding fathers of Madison Avenue.

Contact Jennifer on LinkedIn or the Preston Spire website.

In episode 136, I sit down with JP Holecka, founder and CEO of Power Shifter Digital, a Vancouver-based agency leading the shift toward AI-driven digital products and content creation. With over 30 years of experience in design, film, and technology, JP has guided multiple teams through successful AI rollouts—transforming workflows, scaling creativity, and redefining how digital agencies deliver value.

We talk about what it really takes to evolve your agency for the AI era, how to navigate the culture shift that comes with automation, and why embracing AI is less about replacing people and more about amplifying what they’re capable of.

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SHOW REFERENCES

Access JP's AI Miro Board referenced in the episode here. PW: cleardigital

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JP Holecka is the founder and CEO of Power Shifter Digital, a Vancouver-based agency leading the shift toward AI-driven digital products and content creation. With over 30 years of experience in design, film, and technology, JP has guided multiple agencies through successful AI rollouts—transforming workflows, scaling creativity, and redefining how teams collaborate with generative tools.

Contact JP on the PowerShifter website or on LinkedIn.

In episode 135, I sit down with Drew McLellan, CEO of Agency Management Institute and host of the Build a Better Agency podcast. Drew’s been in the business for over 30 years and has coached thousands of agencies on how to grow profitably, attract better clients, and actually enjoy the perks of ownership.

In this conversation, we unpack what the real job of an agency owner is — and how easy it is to get lost in the weeds doing everyone else’s. Drew shares how founders can move from day-to-day chaos to the higher-level work of vision, leadership, and building a pipeline that doesn’t depend on them. We also talk about the mental shift from “founder hustle” to “CEO clarity,” and what it really means to build an agency that serves your life, not the other way around.

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Drew McLellan has worked in advertising for 30+ years and started his own agency, McLellan Marketing Group, in 1995 after a five-year stint at Y&R and still actively runs the agency. He spends the lion’s share of his time running Agency Management Institute (AMI), which he also co-owns/runs with his wife Danyel.

AMI serves thousands of small to mid-sized agencies (advertising, digital, marketing, media, and PR) every year, so they can increase their AGI, attract better clients and employees, mitigate the risks of being self-employed in such a volatile business, and best of all — let the agency owner actually enjoy the perks of agency ownership.

AMI is the only agency network that is run by an active agency owner. It offers:

Public workshops for agency owners, leaders and account service staff

Owner peer networks (like a Vistage group or 4A’s forums)

Private coaching/consulting for agency owners

Annual primary research with CMOs and client decision makers about their work with agencies

The highly praised podcast Build A Better Agency

The only conference built for small to mid-sized agencies – the Build A Better Agency Summit

Drew often appears in publications like Entrepreneur Magazine, New York Times, Washington Post, Forbes, AdAge, CNN, BusinessWeek, and many others. The Wall Street Journal calls him “one of 10 bloggers every entrepreneur should read.”

He’s also written several books, the most recent being Sell with Authority (January 2020). The latest book has garnered rave reviews and has been the guidebook for agency growth and business development in today’s world.

Drew also speaks at leading agency and marketing conferences like Inbound, Content Marketing World, and MAICON and is often cited in agency-centric content for his expertise in the industry.

When he’s not hanging out with clients or agency owners and their staff, Drew spends time with his wife, their blended family, and following his beloved Dodgers.

Learn more about Drew and AMI on their website.

In episode 134, I sit down with Jen Moss, Chief Creative Officer and co-founder of JAR, where she helps brands and agencies craft podcasts that move people—not just metrics.

Jen calls herself a podcasting doula, guiding clients through the messy middle of creative storytelling. In this conversation, we dive into how to create audio that actually connects, what makes a podcast worth listening to, and why “Job, Audience, Result” is the framework every agency should adopt before hitting record.

Jen and I explore why most branded podcasts fizzle, how to define success beyond downloads, and the difference between authenticity and algorithm-chasing. If you’ve ever thought about starting a podcast for your agency—or making your current one work harder—this episode’s for you.

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• The JAR method: Job, Audience, Result—a simple framework for podcast strategy.

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00:00 Intro – Meet Jen Moss, podcasting doula and CCO of JAR

In her role as Chief Creative Officer of JAR, Co-Founder Jen Moss loves bringing stories to life. With her clients, Jen acts as a “podcasting Doula,” helping them harness their strengths in service of great storytelling. Deeply steeped in the creative process, Jen is unafraid of its ambiguities, and enjoys guiding others through its twists and turns. Drawing on her strong background in theatre, arts journalism, audio documentary, and new media storytelling, Jen helps clients tell the authentic stories that matter to them, and to their audience. She spent many years working as a producer and award-winning content creator for CBC Radio, and as an interactive story producer for The National Film Board of Canada’s Digital Studio, which taught her to think of stories as living things, full of potential for impact. It also taught her to take an “audience first” approach. Jen is never afraid of surfacing big ideas, but understands that sometimes, it’s the little things – the specific lens that “only you” can bring – that will gain the most traction with an audience. Jen loves to look for “fresh tracks” in the form of stories that haven’t been told before. She encourages her clients and her team at JAR to try out new ideas, learn from what the audience data reveals, and let that inform future creative strategy. Finally, Jen keeps her own professional learning curve alive as she lectures part-time at the University of British Columbia’s School of Creative Writing, interacting with the next generation of writers, podcasters, new media producers, and audiences.

Contact Jen on their website or on LinkedIn.

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