David J. Ebner traces his storytelling career back to childhood dinners in a small Ohio town, stretching the truth just to get an emotional reaction out of his mom. Now, as president of Content Workshop, he helps B2B tech brands find the human story buried inside their most technical products. In this conversation, we get into why AI is flooding the market with sameness, why some clients leave for AI tools and come right back, and why the agencies winning right now are the ones willing to zag.

James Kwon built Figmints into a fifteen-year, twenty-person agency by treating it as both a services shop and a product lab, and one of those internal products just sold for almost nine figures. In this episode, he opens up about the acquisition that shaped his approach to M&A, the AI-driven shift from moats to boats, and the day he had three hundred dollars left in the bank account. He also breaks down Slices, his own pay-for-performance model that turned a fifty-thousand-dollar hire into someone earning six figures. It's a conversation about building an agency that can grow, sell, or just work better for the people inside it.

Every founder has a blind spot when it comes to delegation, and it usually shows up as the same bad habit: pulling things back onto their own plate the moment they let go. In this episode, Megan Long of Second First joins me to talk about the role most agencies get wrong from day one, the second-in-command. We dig into why the "sexy resume" hire almost always fails, why the best partnerships look more like a shared Venn diagram than a pair of opposites, and what it actually takes for a founder to leave for a month and come back to a business that grew without them.

Lynn Juang spent two decades climbing from client services to COO before deciding she'd rather help founders run their agencies than run one herself. In episode 161, she breaks down why agency growth doesn't have to come with friction, and what actually separates a business that looks successful from a company built to last.

Every solopreneur hits a ceiling — the question is whether you know it's there. In episode 160, David Shriner-Cahn of Smashing the Plateau joins me to talk about why expertise-based businesses stall out, and how a trusted peer group can show you the blind spot you can't see for yourself. We get into pricing fear, the discipline of ninety-day objectives, and why a weekly cadence might be the most underrated growth lever you're not using.

Courtney Spritzer built SocialFly from a bootstrapped side hustle into an agency worth acquiring, then walked away from it entirely. In this episode, she breaks down what it actually takes to prepare an agency for a sale years before you're ready to sell, and why owner dependency kills more deals than anything else. She also shares how Entreprenista grew from a podcast into a 3,700-member community for women founders. It's a candid look at building a business that can run without you.

Matt Dean set a goal at 19 to own an agency by 30. Five years after launching Dean & Co. with his wife Jackie, he's built one of the most in-demand branding studios in commercial real estate, working across seventeen states, by refusing to be a generalist and refusing to be called a vendor.

Sam Shepler, founder and CEO of StorySnap, joins me to unpack why he's never chased retainers in the B2B video space and how gross margin, not billing structure, actually determines whether an agency can scale. We talk about why feast-or-famine is really a symptom of weak lead flow, not a billing problem, and why his best acquisitions add new capability instead of just new revenue. Sam also breaks down the gross margin mistake he sees in nearly every agency P&L he reviews, and why pulling revenue forward matters more than the comfort of predictable monthly billing.

Zach Rosenberg, founder and CEO of Cortex, joins me to unpack why nearly 90% of video content is mis-categorized and how that skews the data brands rely on. We talk about why buying intent shows up in what people watch long before it hits a search bar, and why AI should support creative instincts rather than replace them.

Jessica Rhodes launched the world's first podcast booking agency in 2013 and has since booked over 50,000 interviews. In this episode, she breaks down why relationship-driven guesting beats AI spam, when to start your own show, and how agency owners can turn a single interview into referrals, repurposed content, and clients who show up ready to buy.

Mike Bodkin spent nearly a decade building Giant Propeller before a partnership unraveled and an unexpected offer pulled him into an exit he never planned. In this episode, he unpacks what made his agency sellable, why integration is never clean, and how a near-shore talent model became the business he runs today.

Scale gets thrown around like a vanity metric, but Juliana reframes it as something quieter and more powerful: the freedom to choose what you do with your day. Her SCALE framework walks owners from seeing what's actually happening in the business all the way to designing an exit — on their own terms, whether they ever sell or not.

Mike Perry, founder and Chief Creative Officer of Tavern, joins Agency Bytes to unpack "modern heritage" — building timeless brands by mining the past instead of chasing trends. Steve and Mike dig into real niching, staying hands-on as a founder, launching your own product brand, and why this is fundamentally a relationship business above all else.

In episode 151, I sit down with Mark Homer of Grandin Holdings to demystify M&A for agency owners. We bust the myth that you need a pile of cash to buy an agency, dig into why your network is your best source of deals, and talk through what actually makes a business sellable — and worth keeping. If you've ever assumed M&A wasn't for you, this one will change your mind.

In episode 150, I flipped the mic. To kick off Season 4, I handed the host chair to my friend Todd Giannattasio of Tresnic Media — a returning guest from episode 10, and the guy who helped me name Agency Outsight in the first place.

This one's more personal than most. Todd walks me through my journey from screw-off art kid to graphic designer to accidental agency owner, the acquisition that should have been the first of many, selling my agency, and the grief that ultimately reshaped how I think about purpose, work, and what a business is really for. We get into the asset mindset, programmatic M&A as a growth lever, why most founders pay themselves last (and shouldn't), and the copycat goals that keep agency owners chasing someone else's dream.

If you've ever wondered what's actually on the other side of an exit — or whether you're building a business or just a really demanding job — this is the conversation.

Key Bytes

• Most agency founders accidentally build a job, not an asset — and the difference shows up the day you try to sell.

• Programmatic M&A unlocks exponential growth that organic effort simply can't match.

• Buying talent is faster, safer, and more predictable than hiring it.

• You don't need a truckload of cash to acquire — SBA loans, earnouts, and seller financing make deals possible at almost any size.

• Paying yourself last isn't noble — it's a habit that quietly devalues the business you built.

• Copycat revenue goals pull founders into chasing numbers that mean nothing to their actual life.

• Grief, burnout, and life events have a way of forcing the clarity most founders avoid.

• Creative empathy — not tactics — is still the most underrated edge agency owners have.

Chapters

00:00 Flipping the mic: why Todd is interviewing me

02:47 From screw-off art kid to graphic designer

05:30 Starting the agency with ego and no business plan

08:25 The acquisition I should have repeated four times

11:00 Selling the agency and what came after

14:30 Grief, COVID, and finding purpose in the garden

17:10 Launching Agency Outsight and pricing it on instinct

21:40 The asset mindset: building enterprise value

26:00 Programmatic M&A as the real growth lever

30:15 Why founders pay themselves last (and shouldn't)

33:00 Copycat goals and chasing someone else's dream

36:00 Rapid-fire questions and closing thoughts

In episode 149, I sit down with David Wain-Heapy, founder of Prodigy, a company that helps agencies and digital businesses build flexible, scalable remote teams through global talent sourcing.

David spent 14 years building and running a Magento-focused e-commerce agency out of central London before selling it to Brave Bison PLC. We talk through what that exit process actually looked like, why the right acquirer matters as much as the right offer, and how building systems independent of the founders made the transition possible.

From there, we get into the real substance of what David does now: helping agencies shift from an outsourcing mindset to an offshore hiring mindset. There's a difference, and it matters. Agency owners will come away with a clearer framework for when and how to integrate global talent, how to think about time zones, which roles translate well offshore, and what AI is actually doing — and not yet doing — to development teams in agencies right now.

Key Bytes

• Outsourcing and offshore hiring are not the same thing — one is a handoff, the other is a hire.

• The fix for a failed first attempt wasn't better talent, it was better integration — sprints, tools, and cadence.

• Building a business that runs independently of you isn't just good leadership, it's what makes you acquirable.

• The right acquirer matters as much as the right offer — alignment on team and culture is what made a six-month handoff possible.

• East Coast agencies fit well with Eastern European talent; West Coast agencies are better served by South and Central America.

• AI handles contained tasks well, but it still can't hold the context of an enterprise-scale project.

• The people who will thrive in an AI-augmented world are the ones who bring real creativity — the architects and problem-solvers, not just the executors.

Chapters

00:00 Why this conversation matters for agency owners right now

01:45 David's 14-year agency journey and building in a competitive London market

05:10 The first attempt at offshore talent and why it failed

08:30 Selling to Brave Bison: what the exit process actually looked like

13:15 Choosing the right acquirer and making a clean handoff

17:00 Outsourcing vs. offshore hiring: why the mindset shift changes everything

21:30 How to think about time zones when sourcing global talent

24:45 What systems agencies need before hiring offshore

28:00 Where AI is actually helping agency dev teams right now

33:20 Which roles work well offshore and which don't

37:50 Rapid fire: surfing in Bristol, letting go of control, and a risky bet that paid off

David Wain-Heapy is an experienced founder currently focused on building remote teams for digital businesses with Prodigi.

Having sold my digital agency to Brave Bison PLC, I am now working to provide a flexible and scalable solution that enables companies to take control of hiring by looking at a global talent pool.

I have many years experience building globally distributed teams of digital professionals and leading them to help great businesses win in the race for attention and accelerate their digital growth.

Contact David:

https://www.linkedin.com/in/david-wain-heapy/

http://www.prodigi.team

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.

Key Bytes

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

• Operational discipline isn’t about bureaucracy — it’s about freeing the founder from the day-to-day.

• If you’re still the glue holding everything together, you don’t have a scalable business — you have a dependency.

• Working on the business requires intentional systems, delegation maturity, and the courage to step back.

• Strong operators build companies that can grow, sell, or run without the founder in the weeds.

Chapters

00:00 Welcome & Cameron’s Scaling Background

04:12 The Difference Between a Founder and a CEO

09:48 Why Most Agencies Don’t Truly Work “On” the Business

16:35 The COO Mindset Explained

23:10 Founders as Bottlenecks

31:42 Building Operational Discipline Without Red Tape

40:18 Hiring & Developing Strong Operators

49:03 Scaling vs. Lifestyle Businesses

57:25 Final Advice for Agency Owners

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.

www.cooalliance.com

www.cameronherold.com

https://www.instagram.com/cameron_herold_cooalliance

https://www.facebook.com/COOAlliance/

https://www.linkedin.com/in/cameronherold

https://www.linkedin.com/company/coo-alliance/

https://twitter.com/cooalliance

https://www.youtube.com/@CameronHerold?sub_confirmation=1

https://cooalliance.com/vivid-vision/

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.

Key Bytes

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

• Staying small on purpose can be a growth strategy — speed and momentum beat bureaucracy.

• If you don’t share your work, people can’t refer you because there’s no proof you exist.

• Spectacle marketing works when it’s aligned, intentional, and captures attention in a sea of noise.

• Diversifying income through products creates longevity — especially when your body can’t grind forever.

Chapters

00:00 Welcome + who Amy Hood is

01:05 Hoodzpah’s origin: “unhireable on paper” to studio owners

02:59 Twin partnership: dividing roles and avoiding scorekeeping

08:41 Staying small on purpose (and why bigger can be slower)

11:18 Landing better clients by making the work you want

18:03 Dream clients + putting your hat in the ring

21:00 Adobe MAX banner plane: “No more broke creatives”

28:40 From service to product: book, fonts, and Fort app

31:48 Font licensing fear and why clients are gun-shy

38:44 Rapid fire: resets, creative myths, and boundaries

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 back hand. She co-authored the book “Freelance, and Business, and Stuff: A Guide for Creatives” (and it's related online course) with her sister Jennifer based on the Professional Practices class they taught at Laguna College of Art & Design.

www.hoodzpahdesign.com

instagram.com/hoodzpahdesign

youtube.com/hoodzpah

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.

Key Bytes

• Why replacing humans with AI backfired for many brands in 2025

• How AI slop diluted trust, performance, and differentiation

• Why humans must remain the source of truth in content strategy

• How to use AI to analyze, enhance, and scale—not replace—expertise

• Why long-form, opinionated content performs better with LLMs

• How organic social still drives testing, trust, and paid performance

• Why being different beats being “better” in crowded markets

• How agencies should rethink in-house marketing investment

Chapters

00:00 Why 2025 became the “AI correction year”

02:30 What brands got wrong when they replaced people with AI

05:45 Why agencies must treat themselves as their best client

08:55 AI avatars, ethical concerns, and consumer trust

11:30 From AI slop to human-led strategy

15:05 Humans as the source of truth in content

19:45 Why long-form content matters for AI discovery

21:20 Organic social isn’t dead—it’s misunderstood

26:25 Organic + paid: why they must work together

28:00 Rapid-fire questions and practical takeaways

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.

https://www.moreinmedia.com/

https://www.linkedin.com/in/moreinmedia/

https://www.youtube.com/@DorienMorinVanDam/podcasts

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.

Key Bytes

• Why answering a creative calling is an ongoing commitment, not a one-time decision

• How staying true to your craft doesn’t require self-sacrifice

• The role boundaries and structure play in long-term creative freedom

• Why defining success for yourself is the real creative advantage

• How creatives can grow without burning out or losing their voice

Chapters

00:00 Following a creative calling

06:40 Staying true to your craft over time

14:10 Defining success on your own terms

22:35 Boundaries, pricing, and protecting creative energy

31:20 Structure as a support, not a constraint

40:05 Evolving creatively without losing yourself

48:30 Advice for creatives building sustainable careers

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.

@jessicahische (threads and instagram)

jessicahische.is/awesome

studioworks.app