In episode 148, I sit down with Cameron Herold, founder of COO Alliance and one of the most recognized voices in operational leadership, to talk about the mindset shift agency owners desperately need right now: stepping into the role of CEO and building a true COO mindset inside their business.

Cameron has helped scale companies like 1-800-GOT-JUNK and advised hundreds of growth-stage businesses, and in this conversation, we unpack what it really means to work on the business instead of being trapped inside it. We talk about the operator’s lens, how founders accidentally become bottlenecks, and why operational maturity is often the difference between a lifestyle business and a scalable asset.

If you’re an agency owner who feels stretched thin, stuck in delivery, or unsure how to elevate your leadership team, this one is a masterclass in stepping up and leveling up.

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• The CEO’s job is vision. The COO’s job is execution. Most agency owners are trying to do both — and burning out.

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00:00 Welcome & Cameron’s Scaling Background

Cameron Herold is the mastermind behind the exponential growth of hundreds of companies globally. Founder of the COO Alliance and Invest In Your Leaders training. Cameron is known as the "CEO Whisperer" and is also the former COO of 1-800-GOT-JUNK?, where he engineered the company's spectacular growth from $2 million to $106 million in revenue in just six years.

The publisher of Forbes magazine, Rich Karlgaard, stated, "Cameron Herold is the best speaker I've ever heard...he hits grand slams”. Cameron is the host of the Second In Command podcast, author of 6 bestselling books, including The Second In Command, Vivid Vision, Meetings Suck, Free PR, Double Double, and The Miracle Morning for Entrepreneurs.

Cameron is a top-rated international speaker and has been paid to speak in 26 countries and on all 7 continents, including Antarctica in early 2022.

Contact Cameron:

In episode 147, I sit down with Amy Hood, designer and co-founder of Hoodzpah Design, the Southern California brand identity studio behind work for Disney, Nike, Netflix, Target, and the Lakers. Amy and her twin sister Jen built Hoodzpah out of necessity after realizing they were “unhireable on paper,” and turned it into a nimble, right-sized studio that’s intentionally stayed small to protect speed, momentum, and creative quality.

We talk about why “make the work you want to get” is still the most reliable path to better clients, how relationships compound when you lead with curiosity (not strategy), and why creatives have to treat marketing as part of the job if they want opportunities to find them.

Amy also shares the story behind Hoodspa’s Adobe MAX banner plane stunt (“No more broke creatives”), what they learned from taking a big marketing swing, and how they’re shifting from service work into products like their updated book Freelance, and Business, and Stuff and the Fort font subscription app.

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• Making the work you want to get is still the fastest way to change the caliber of clients you attract.

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00:00 Welcome + who Amy Hood is

Amy Hood is a designer and co-founder of Hoodzpah, Inc, a brand identity studio in Southern California that has worked with companies like Disney, 20th Century, Nike, The Lakers, Target, and Netflix. Amy's logo and identity work centers around custom lettering solutions. She is the font designer behind Palm Canyon Drive, Beale, and Beverly Drive. When she's not stress-watching Laker games, Amy can be found at the beach, plein-air doodling, and practicing her Smashball backhand. She co-authored the book “Freelance, and Business, and Stuff: A Guide for Creatives” (and its related online course) with her sister Jennifer, based on the Professional Practices class they taught at Laguna College of Art & Design.

Contact Amy, grab their book, or fonts all on the Hoodzpah website, Instagram, or YouTube channels.

In episode 146, I’m joined by Doreen Morin-van Dam, a content strategist with more than 15 years of experience helping brands grow through smart, sustainable marketing. Doreen works with teams on how to use AI responsibly and effectively, hosts the Strategy Talks video podcast, and is known for blending emerging tech with deeply human content strategies.

We dig into what really happened when companies rushed to replace humans with AI in 2025—and why many of them quietly reversed course by Q4. Doreen shares what she’s seeing brands regret most, how “AI slop” became a real problem, and why human-led content is becoming a competitive advantage again. We also explore how agencies can use AI as a strategic partner (not a shortcut), why long-form content matters more than ever, and how organic and paid media must work together. This is a grounded, practical conversation for agency owners trying to navigate AI without losing trust, quality, or their voice.

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Dorien Morin-van Dam is a Vermont-based content strategist with over 15 years of experience helping brands grow through smart, sustainable strategies. A Certified Social Media Manager and Agile Marketer, she also consults on AI strategy for small businesses, showing teams how to use AI in marketing responsibly and effectively. Dorien turns organic content and emerging tech into measurable results, speaks internationally, and hosts the Strategy Talks video podcast. You’ll recognize her on stage and online by her signature orange glasses, a nod to her Dutch heritage.

Check out Dorien’s website, connect on LinkedIn, or tune into the Strategy Talks podcast.

In episode 145, I sit down with Jessica Hische—a world-renowned lettering artist, New York Times bestselling author, and one of the most thoughtful creative voices of our generation. And full transparency: I’ve been a huge fan of Jessica’s work for a long time. Her ability to pair obsessive craft with clarity, intention, and humanity has influenced how I think about creative work for years.

This conversation goes far beyond tactics or tools. We dig into what it really means to answer a creative calling—and then protect it. Jessica shares how she’s built a career that honors her instincts, values her time, and stays deeply connected to her craft, without burning out or selling out. We talk about the choices she’s made to stay true to her creative voice, even when external pressure—clients, platforms, trends, or scale—could easily pull things off course.

We also explore the less romantic but absolutely essential side of creative freedom: boundaries, systems, pricing, and self-advocacy. Jessica opens up about how she’s learned to put structure around her work not as a constraint, but as a way to preserve joy, sustainability, and long-term creative integrity. Whether it’s choosing the right projects, saying no without guilt, or building tools that support creatives instead of exploiting them, her through-line is clear: creativity thrives when it’s respected.

For agency owners and creative leaders, this episode is a powerful reminder that building a business—or a career—on your own terms isn’t about sacrificing ambition. It’s about defining success for yourself, staying grounded in your craft, and making intentional choices that allow your work, and your life, to evolve together.

This one felt special to record—and I think it’ll resonate deeply with anyone trying to build something meaningful, creatively and personally.

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Jessica Hische is a lettering artist and New York Times Best-selling author based in Oakland, California. She specializes in typographical work for logos, film, books, and other commercial applications. Her clients include Wes Anderson, The United States Postal Service, Target, Hallmark, and Penguin Books and her work has been featured again and again in design and illustration annuals both in the US and internationally. She’s been named a Print Magazine New Visual Artist (20 under 30), one of Forbes 30 under 30 in Art and Design, an ADC Young Gun, a “Person to Watch” by GD USA, and an Adweek “Creative 100”. She's also the co-founder of Studioworks, invoicing software for creatives by creatives.

Contact Jessica on their website, Threads, and Instagram, and learn about Studioworks here.

In episode 144, I’m joined by Ali Mirza, a sales expert who’s personally closed over $450 million in revenue and advised hundreds of high-growth companies, including multiple Inc. 500 winners and successful exits.

Ali and I dig into what’s really broken in agency sales today — from why “more leads” isn’t the answer, to how founders unintentionally sabotage deals, to the mindset shifts required to close larger, more confident engagements. This conversation is especially relevant for agency owners who are great at delivery but feel stuck, uncomfortable, or inconsistent when it comes to selling.

We talk candidly about sales systems vs. sales personalities, the danger of winging it, and how agencies can move from reactive selling to intentional, scalable growth without becoming someone they’re not.

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• Why “just getting more leads” rarely fixes agency sales problems

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00:00 Why agency sales feels harder than it should

Ali Mirza is a sales expert who has personally closed over $450 million in sales with multiple Inc. 500 companies and high-growth startups.

His work has been featured in Inc., Forbes, Huffington Post, Business Insider, and more. He has consulted for hundreds of companies, with 17 earning the Inc. 500 Fastest Growing Companies award and three successfully acquired. He is president of Atlanta-based consulting firm, Rose Garden.

Connect with Ali on his personal website, his consulting website, or on his Instagram.

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.