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 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

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.

Key Bytes

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

• The hidden mindset traps that keep agency owners underpricing

• How confidence (not pressure) actually drives better close rates

• The difference between selling expertise vs. selling outcomes

• Why inconsistent sales processes hurt valuation and scalability

Chapters

00:00 Why agency sales feels harder than it should

04:32 The biggest sales myths agency owners believe

09:15 Why confidence matters more than scripts

14:40 Selling outcomes vs. selling services

20:05 How founders accidentally sabotage deals

26:18 Pricing fear and the psychology behind it

32:10 Building a repeatable sales process

38:45 What great agency sales leadership really looks like

44:20 Final advice for agency owners who hate selling

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:

alimirza.com

rosegardenconsulting.com

IG: @alimirza.rgc

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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.

Key Bytes

• Scaling doesn’t have to mean sacrificing creative quality

• Your process is what protects the craft as you grow

• “Better clients” often solves what “more clients” can’t

• You can stay hands-on without being the bottleneck

• The right constraints create consistency, not limitation

• Hiring should reduce friction, not add management drag

• Clear scope and boundaries prevent quiet burnout

Chapters

00:00 Intro: scaling without losing the craft

02:10 Amy’s origin story and building Maxwell Design

06:20 The “stay small” choice and what it protects

11:05 When growth starts to strain quality (warning signs)

16:10 Processes that keep creative standards high

22:30 Team structure: support roles vs creative roles

28:40 Client fit, boundaries, and saying “no” earlier

34:15 Staying fulfilled while the business grows

40:20 Rapid-fire questions and wrap-up

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.

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

http://maxwelldesignco.com/

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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.

Key Bytes

• Why the traditional agency “bro playbook” is failing modern agencies• The hidden cost of hustle culture on owners and teams• How emotional intelligence impacts agency growth and retention• What healthier leadership looks like inside agencies• Redefining success beyond revenue and headcount

Chapters

00:00 Why the traditional agency playbook feels broken05:12 The origins of hustle culture in agencies11:04 Masculine-driven leadership norms and their impact17:32 Emotional intelligence as a growth lever23:58 Building healthier agency cultures30:41 Operator-led leadership vs. ego-led leadership37:10 Sustainable growth without burnout43:26 Redefining success as an agency owner49:12 Advice for owners ready to do things differently

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.comhttps://bit.ly/MWDarlingshttps://waverlyave.comhttps://instagram.com/waverlyave.cohttps://www.lecheile.co/contacthttps://www.instagram.com/lecheile.co/

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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.

Key Bytes

• Why creatives struggle with pricing — and how to fix it

• The mindset shift from freelancer to business owner

• How Michael positioned his agency to win massive clients

• The surprising relationship between process, profit, and peace

• What creatives get wrong about value

• Why “portfolio thinking” holds owners back

• How to build a business that supports your life, not the other way around

Chapters

00:01 Welcome + Michael’s background and agency journey

04:12 From creative chaos to building processes that scale

09:45 Why pricing is emotional—and how to make it objective

14:30 Portfolio vs. business owner mindset

19:58 Finding ideal clients and positioning that works

25:21 How Michael sold his agency and what he learned

31:44 The psychology of creative profitability

38:10 Achieving peace of mind as an owner

44:22 Michael’s advice for creatives who feel “stuck”

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.

Community: https://morecreativeacademy.com

Instagram: https://instagram.com/morejanda

YouTube: https://youtube.com/morejanda

LinkedIn: https://linkedin.com/in/morejanda

Website: https://michaeljanda.com

Courses: https://morejanda.teachable.com

In episode 132, I talk with Leah Leaves, founder of Alderaan Operations Solutions, where she helps remote digital agencies grow without the grind. Known for her no-fluff, systems-first approach, Leah and her team embed expert operations managers directly into agencies to break bottlenecks, reduce burnout, and build businesses that can scale without the founder in every decision.

We dig into what causes owners to become the bottleneck, the difference between goals, systems, and team accountability, and how every agency—no matter the size—can start building a foundation that prevents burnout and supports growth. Leah also shares how to identify when it’s time to bring in an operator, how to delegate effectively, and why even the best creative agencies need structure to thrive. We wrap by exploring how AI fits into internal operations and why every agency needs an AI Ops roadmap, even if it’s just six months ahead.

Key Bytes

• Burnout often begins with unclear goals and missing systems; clarity is the antidote.

• Leah outlines four agency owner archetypes—the Trusting Optimist, Firefighting Founder, Reluctant Gatekeeper, and Visionary Leader—and how operators help each evolve.

• Delegation isn’t dumping tasks; it’s empowering your team with context and ownership.

• Documenting the “why” behind your systems drives consistency and accountability.

• Operators create the scaffolding for scale—allowing founders to focus on vision, not firefighting.

• Every agency, regardless of size, benefits from an AI Ops roadmap to guide internal efficiency.

• Start with what you already have—processes, checklists, or recurring workflows—and build from there.

• Systems don’t kill creativity; they protect it by removing chaos and decision fatigue.

Chapters

00:00 Intro and welcome with guest Leah Leaves, founder of Alderaan Operations Solutions

02:00 The Star Wars origin of “Alderaan” and Leah’s path from journalism to operations

05:30 From creative to systems thinker: finding flow in operations

08:00 How unclear goals and missing systems cause bottlenecks

10:00 Guardrails vs. micromanagement: empowering the team without overengineering

13:00 The burnout cycle and why delegation is a creative act

15:00 The four types of agency owners and their operational challenges

20:00 Shifting from bottleneck to visionary: the operator’s role in scaling

23:30 Why every agency needs an AI ops roadmap

26:30 Putting “robots” in the org chart and making automation work

29:00 Low-hanging AI wins: onboarding, recruiting, and workflow automation

32:00 Rapid-fire Q&A: distilling systems, theme songs, and unexpected client wins

34:45 Closing thoughts and where to find Leah

Leah Leaves is the Founder of Alderaan Operations Solutions, where she helps remote digital marketing agencies grow without the grind. Known for her no-fluff, systems-first approach, she and her team embed expert Operations Managers directly into agencies to break bottlenecks, reduce burnout, and build businesses that can scale without the founder in every decision.

https://www.linkedin.com/in/1eah1eaves/

https://alderaanenterprise.com/

http://agencyownerquiz.com/

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In episode 130, I sit down with Peter Lang—co-founder of Digital Agency Business and AVA, and longtime agency acquirer—to unpack how agency owners can use M&A as a growth superpower. Peter shares the seven-day deal that doubled his agency’s revenue, the due-diligence signals that actually matter (talent, client stickiness, and contracts), why most M&A fails on culture not math, and how AI is reshaping hiring and service models. We also get into founder identity after the sale, what “professional maturity” looks like, and why many owners are really capital allocators in the making.

Key Bytes

• M&A can compress years of organic growth into months—if you underwrite people, clients, and terms before the numbers.

• Culture fit and integration planning beat fancy spreadsheets; most failed deals are value misalignment, not valuation.

• AI is wiping out entry-level tasks first; the winners redeploy A-players and teach clients how to use AI, not hide from it.

• Founder-led sales can’t be the only engine; build repeatable sales capacity that survives distractions.

• You already “work for” whoever pays you—selling changes the customer, not your agency DNA.

• Treat time like capital: budget it, forecast it, and review it like an effective executive.

Chapters

00:00 Cold open, quick re-intro

01:08 The seven-day deal that doubled revenue

03:32 Doing three deals in 90 days during COVID

06:36 Common seller misconceptions and Peter’s deal lens

09:19 Endurance mindset, calendars, and operating like an athlete

13:46 What buyers actually look for beyond the numbers

17:43 AI’s impact on talent, delivery, and survival to 2027

22:10 Life after the sale and “professional maturity”

24:51 Rapid fire: celebrating wins, the race that changed him, dream acquisition

27:45 Where to learn more (digitalagencybusiness.com)

Resources mentioned

• Effective Executive by Peter Drucker (time tracking and retrospective)

• GrowthHackers community (context on Peter’s portfolio)

• digitalagencybusiness.com (Peter’s M&A training and upcoming book)

Peter Lang is an entrepreneur, investor, and philanthropist with over 15 years of experience building, buying, and selling companies across online publishing, media, advertising, e-commerce, and consulting. He’s the co-founder and Chief M&A Officer at AVA, a fast-growing digital agency holding company acquiring businesses in the $1–10 million range.

Peter also runs Digital Agency Business (DAB), an e-learning company that trains entrepreneurs to launch and scale their own agencies. A former CEO of Uhuru Network and advisor to multiple companies, Peter’s passion lies in using mergers and acquisitions to accelerate growth. An endurance athlete and family man, he lives by the belief that anything is achievable with hard work.

Contact Peter:

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

https://digitalagencybusiness.com/

In episode 129, I talk with Natasha Golinski, founder of On Purpose Projects, a custom web and e-commerce dev agency. Natasha is a three-time Canada Women of Influence nominee, a mom of three, and a breast cancer survivor—and she’s built her business around the belief that mindset is everything.

We dig into how she went from “accidental agency owner” to leading a zero-meeting, all-contractor team for over a decade, and why journaling, EFT (tapping), and surrounding yourself with the right people are critical to surviving the entrepreneurial rollercoaster. Natasha also shares how a cancer diagnosis forced her to hire ops support—and ultimately led to one of her agency’s biggest months ever.

This episode is a masterclass in grit, leadership, and the mental game of entrepreneurship.

Key Bytes

• Mindset is the job. Natasha starts most days with journaling and EFT to reset anxiety and focus.• Zero meetings, high loyalty. A culture of respect, gratitude, and no drama keeps her contractor team thriving.• Protect your people. Leadership means absorbing the stress and passing the praise.• Say no early. Guardrails in discovery protect the team from toxic clients.• Crisis as catalyst. Cancer forced Natasha to let go of ops—and it unlocked growth.• Community matters. No one is self-made—surround yourself with peers who lift you up.• Focus sharpens delivery. On Purpose Projects does dev only—like a food truck that just serves crepes.

Chapters

00:00 Welcome & Natasha’s background02:12 Accidental agency beginnings04:45 Mindset, marketing, and money: her founder lane07:30 Morning pages & EFT as daily reset tools11:05 Cancer diagnosis, hiring ops, and a breakthrough month15:20 Building loyalty in a zero-meeting contractor culture20:22 Client red flags & protecting your team23:50 Why no one is self-made: the role of community26:30 Rapid-fire fun: karaoke, first impressions, food truck metaphor28:55 Closing thoughts

Natasha Golinsky is the founder of an award-winning web development and ecommerce agency, a three-time nominee for the Canada Women of Influence® Award, and a tireless champion of female agency owners. Natasha’s also a mom of three and a breast cancer survivor who brings grit, heart, and a deep sense of purpose to everything she does. I’m thrilled to dig into her journey, her mission, and the lessons she’s learned along the way. Natasha, welcome to the show.

Award winning web development & ecommerce agency founder | Champion & connector of female agency owners | 3x nominee Canada Women of Influence® Award | Breast Cancer Butt-Kicker | Mom x 3

http://www.onpurposeprojects.com

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

In episode 120, I sit down with Greg Bellinger, co-founder and CEO of White Rabbit, a web and mobile development agency with nearly 100 in-house employees spread across Colombia, India, and the U.S. Greg shares his journey from frontend developer to visionary CEO and breaks down how White Rabbit scaled by staying focused on one niche—supporting other agencies.

We explore why White Rabbit only hires full-time employees, how niching into agency delivery gave them a competitive edge, and the strategic thinking behind launching their own internal project financial software. Greg also talks about his passion for creation, not just in code but in culture, leadership, and future products. This one’s full of takeaways for agency owners looking to scale with purpose.

Key Bytes

• Greg shares why they only hire full-time employees and the cultural benefits that come with it

• He explains how niching into working with agencies helped them scale more efficiently

• Greg reflects on stepping away from product management and letting his leadership team shine

• He talks about the challenges of managing across three countries and how they keep their culture unified

• Greg reveals details about their custom-built project management and financial tool

• He offers insight into people management, tough conversations, and protecting your energy

• He shares his personal philosophy of “create,” from coding to building culture

• Greg discusses what entrepreneurship means to him and how it’s been part of his DNA from the start

Chapters

00:00 Welcome and guest intro

01:00 The origin of White Rabbit and its full-time hiring philosophy

02:30 Transitioning out of coding and project management

06:00 Working exclusively with agencies vs. going direct

07:15 Niching and its impact on growth and clarity

10:00 Scaling globally: why Colombia, India, and the U.S.

12:00 Uniting culture across three countries

14:00 Vision for the future: stepping back, launching products

16:30 Building internal software for project and financial management

19:00 Lessons in people management and entrepreneurship

25:00 Rapid fire: guilty pleasures, two-word advice, and dream hire

Greg Bellinger is the Co-Founder and CEO of White Rabbit Group, a web and mobile development agency with a fully in-house team of nearly 100 employees across three countries. His passion for technology began in childhood, leading him to hand-code his first websites in 2008. In 2016, he co-founded White Rabbit Group, building it into a trusted development partner for world-class agencies and creatives. Under his leadership, the company has earned a reputation for delivering high-quality digital solutions while fostering a close culture of technical experts.

Contact Greg:

https://whiterabbit.group/

https://www.linkedin.com/in/greg-bellinger/

In episode 119, I sit down with Jessica Malnik, a B2B messaging strategist who’s helped over 75 founders and lean marketing teams craft content that actually gets read—and drives results. We talk about the risks of over-commoditized content in the age of AI and why a flood of “cheap” output isn’t a strategy. Jessica walks me through her signature framework, the Marketing MOAT, which focuses on Messaging, Distribution, and Content Efficiency.

She also shares practical, low-lift ways agencies can build content machines, maximize existing assets, and stay consistent without burning out. We even talk about content imposter syndrome, the curse of knowledge, and why you don’t have to be totally unique—you just need to show up as yourself.

If you’ve ever struggled with creating content that converts (and keeps converting), this episode is packed with clarity, systems, and smart takes that’ll help you raise your signal-to-noise ratio.

Key Bytes

• Messaging without a unique perspective leads to content that gets ignored

• AI-only content creation can dilute your brand and commoditize your services

• Her “Marketing MOAT” framework focuses on messaging, distribution, and content efficiency

• Distribution must be built into strategy from the beginning, not as an afterthought

• Agencies should reuse and repurpose evergreen content instead of always creating new

• Consistency (3x/week on LinkedIn) matters more than frequency spikes

• Authenticity in content doesn’t mean oversharing—it means resonance

• Set goals based on team size, budget, and business stage, then reverse engineer your strategy

Chapters

00:01 Welcome and intro to Jessica Malnik

01:46 Common agency messaging mistakes

03:26 Why AI-only content is risky for agencies

05:14 Jessica’s Marketing MOAT framework explained

07:21 How to develop “spiky” messaging and content positioning

10:34 Distribution strategy: where your audience actually is

14:04 Own your content—don’t rely only on social algorithms

15:09 Content efficiency and repurposing systems

19:00 Best practices for publishing frequency

21:16 Balancing personal and professional content

22:28 Reverse engineering content strategy based on goals

23:41 Rapid Fire Q&A with Jessica

Jessica Malnik has helped over 75 B2B founders and lean marketing teams fix their positioning and craft messaging people actually read and respond to.

I’ve spoken at half a dozen in-person conferences in the U.S., Australia, and Thailand, as well as dozens of virtual webinars, workshops, and podcast guest appearances.

I’ve also been featured in WSJ, The Next Web, MicroConf, Wynter, SXSW, and MSN UK, among many others.

Contact Jessica:

https://jessicamalnik.com/newsletter/

https://www.theremoteworktribe.com/

Ep 118 – Jamie Brindle – From Freelancer to Entrelancer: Building a Business That Scales

In episode 118, I’m joined by Jamie Brindle—a freelancer, strategist, and creator who’s built a half-million-strong audience around helping creative solopreneurs build sustainable, scalable freelance businesses. In this conversation, Jamie breaks down what it means to be an “Entrelancer”—a hybrid of entrepreneur and freelancer—and why the traditional view of freelancing is overdue for a reboot.

We talk about why having an audience builds instant trust, how freelancers can evolve into business owners without employees, and the myths around websites and portfolios that keep too many creatives stuck in planning mode instead of taking action. Jamie also shares a powerful framework for moving strangers into long-term client relationships—and why every freelancer should be thinking like a strategist, not just a task-taker.

Whether you’re freelancing, running an agency, or somewhere in between, this one’s packed with fresh thinking.

Key Bytes

• Jamie shares the origin of the term “Entrelancer”—and how it reflects a more modern, business-minded freelancer.

• He explains how their TikTok content (originally not for clients) unexpectedly opened doors to Fortune 100 opportunities.

• We dig into the importance of digital products, productized services, and building systems to support time freedom.

• Jamie outlines the four stages of the customer journey: Stranger → Lead → Client → Client for Life.

• He gives a masterclass in how to manufacture delight, over-deliver, and secure repeat work.

• We challenge the sacred cows of freelancer websites and portfolios—and why Jamie believes they’re massive time-wasters.

• Sales anxiety? Jamie offers a grounded, simple mindset shift that removes pressure and focuses on being helpful.

• He explains how positioning yourself as a solution—not a task-taker—is the unlock to charging more and building authority.

Chapters

00:00 Welcome and Intro to Jamie Brindle

01:00 The accidental power of TikTok and building trust

04:30 Redefining success as a freelancer

07:00 “Entrelancer” vs. freelancer: What’s the difference?

11:40 Scaling without employees: Productized and digital offers

13:00 Pivoting from video work to social media consulting

15:25 Lessons from shifting services and getting back in the field

19:30 Jamie’s four stages of the customer journey

24:00 Reframing sales: It’s just solving a problem

28:00 Positioning yourself as a strategic partner

34:00 Why portfolios and websites are the biggest time wasters

37:00 Final thoughts and closing

Jamie Brindle is a freelancer who gives advice to over half a million other creatives on social media about building a scalable and sustainable freelance business.

Contact Jamie:

Www.jamiebrindle.io

@thejamiebrindle on all socials

In episode 117, I sit down with Wanda Allen, international speaker, coach, and author of Follow Up Sales Strategies. With 25 years in the corporate world and a background in business banking, Wanda developed a systemized approach to sales follow-up that now helps business owners and sales professionals increase their close rates.

We dive into the psychology behind why so many people avoid follow-up, the fears that hold them back (hint: it’s not really about time), and how a simple shift in mindset and process can transform your sales pipeline. Wanda shares data-backed insights, actionable tips for improving follow-up cadence, and even debunks myths about being “pushy.” Whether you’re in active outreach or avoiding the phone like the plague, this episode will motivate you to reframe your follow-up game—and pick up the phone with purpose.

We also talk about her book-writing journey, the importance of believing in the value you bring, and a bucket-list dream that has her heading south of the border.

Key Bytes:

• 98% of sales don’t happen on the first contact—follow-up is essential.

• Fear of being “pushy” and fear of rejection are the top two mindset blocks around follow-up.

• 80% of sales happen between the 5th and 12th contact—most people quit after 2.

• Follow-up is a form of service, not pressure—it shows interest and professionalism.

• The phone is the most efficient tool in sales, yet it’s the most underused.

• You can’t build trust without consistent, committed follow-up.

• Stop assuming silence means disinterest—prospects are often just busy.

• Confidence in your pricing comes from believing in your value.

Chapters

00:01 – Introducing Wanda Allen and the importance of follow-up

01:04 – From corporate banking to follow-up systems expert

03:35 – Writing two books and why her first was retired

06:07 – The real reason people don’t follow up: mindset and fear

07:59 – How to prioritize follow-up and overcome procrastination

11:00 – Why consistent follow-up beats your competition

14:12 – Action over anxiety: staying out of your head during follow-up

16:18 – The forgotten power of the phone in today’s sales world

Wanda Allen is an international speaker, coach and corporate trainer. She's also the author of Follow Up Savvy and Follow Up Sales Strategies. Wanda had a 25 year corporate career where she held the position of Senior Vice President for 15 years. She has a strong skill set for developing systems and applied this skill to the follow up process. She's an expert in helping entrepreneurs, business owners and sales professionals increase pipelines, improve sales performance and strengthen relationships by developing strong follow up skills.

Contact Wanda:

https://www.followupsalesstrategies.com/

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

https://www.facebook.com/FollowUpSalesStrategies

Ep 112 – Jay Owen, Business Builders – Slow Growth, Strong Culture

In episode 112 of Agency Bytes, I sit down with Jay Owen, founder of the multimillion-dollar agency Business Builders and the community Agency Builders. Jay started his web design business at just 17 and has spent the last 26 years growing it—intentionally and steadily—into a values-driven company focused on people over ego and sustainable growth over fast wins.

We dive into the long game of agency leadership, building a business that can thrive without you, and the fulfillment that comes from creating jobs that others love. Jay shares how his faith and values guide the way he leads, the role community has played in his journey, and why slow growth might just be the secret weapon nobody talks about. Whether you’re scaling your team, wrestling with niching, or thinking about legacy, this episode is full of wisdom for the road ahead.

Key Bytes

• Jay Owen started his entrepreneurial journey at a young age.

• Slow growth can lead to more sustainable success.

• Creating job opportunities for others is a key motivation.

• Community is essential for agency leaders.

• Collaboration over competition fosters growth.

• Integrating personal values into business is important.

• Niche down or maintain variety based on personal preference.

• Productization can enhance agency efficiency and profitability.

• Having a support system prevents burnout.

• Building a strong team is crucial for agency longevity.

Chapters

00:00 The Entrepreneurial Spirit Begins

02:37 Navigating the Hills and Valleys of Business

05:35 Building a Team and Creating Opportunities

08:54 The Importance of Community Over Competition

12:50 Creating a Supportive Environment

16:56 Integrating Personal Values into Business

20:56 Niche vs. Variety in Agency Growth

23:32 Productization and Agency Wisdom

Jay Owen started a web design company at 17 years old that has grown to a multi-million dollar agency and still growing 26 years later. He’s the author of Building a Business that Lasts and Host of a Podcast by the same name.  Jay founded Agency Builders, a community to help agency leaders grow and scale in a healthy way.

https://agencybuildersretreat.com/

https://aiwithjay.com/

In episode 103 of Agency Bytes, I sit down with Greg Hickman, founder of Alt Agency and an expert at helping agency owners break free from the time-for-money grind. Greg shares his fascinating journey from the world of big agencies to building his own seven-figure business—while working just 25 hours a week! We dive deep into the pitfalls of the traditional agency model and explore how the Alt Agency approach helps owners productize their services, streamline operations, and reclaim their time.

Greg and I also unpack the difference between productizing and commoditizing agency work (hint: you don’t have to sacrifice creativity for efficiency!). We talk about scaling smart, building systems that don’t drain your soul, and why redefining wealth goes beyond the numbers in your bank account. Plus, Greg shares some personal stories and life lessons about being present for the moments that really matter, in business and at home.

If you’re looking to run a more sustainable and rewarding agency, this is one you won’t want to miss.

Key Bytes

• Greg Hickman transitioned from traditional agency roles to founding AllAgency.

• The Alt Agency model focuses on monetizing expertise rather than just labor.

• Productization of services can lead to greater scalability and efficiency.

• Wealth is defined not just by money, but by time and health.

• Agencies can benefit from creating multiple service tiers to cater to different client needs.

• The lines between agencies, SaaS, and coaching are increasingly blurred.

• Building a scalable business requires a shift in mindset and operations.

• Automation and systems are key to reducing workload and increasing profits.

• Greg's journey highlights the importance of adapting to market needs.

• The impact of helping 800 agencies showcases the ripple effect of effective coaching. 

• Productized services focus on specific outcomes.

• Systematization helps agencies improve efficiency and profitability.

• Lead generation is crucial for agency success.

• Productization simplifies marketing and client management.

• Agencies often lose money due to inefficient pricing models.

• Creativity can thrive within a productized framework.

• Differentiation is key to avoiding commoditization.

• Personal growth involves learning from past experiences.

• Being present in personal life enhances overall happiness.

• Enjoying the journey is as important as the destination.

Chapters

00:00 Introduction to Agency Bites and Guest Background

01:30 Greg's Journey in the Agency World

04:21 Transitioning to the Alt Agency Model

07:37 The Evolution of Services and Client Focus

10:40 Impact and Scale of the Alt Agency Model

12:59 Defining Wealth Beyond Money

13:31 Understanding the Alt Agency Model

19:54 Building a Scalable Offer Suite

21:31 Transforming Agency Services into Productized Offerings

24:33 The Importance of Systematization in Agencies

27:52 Lead Generation and Client Retention Challenges

30:19 Differentiating Productization from Commoditization

33:21 Personal Insights and Life Lessons

Greg Hickman helps agency owners and consultants escape the trap of trading time for money. After nearly two decades working with brands like Pepsi, AT&T, and the NY Jets, Greg built his own marketing automation agency and built funnels and systems for entrepreneurs like Dan Martell, Chris Ducker, John Lee Dumas, Jasmin Star, Nerd Fitness, and more. Now through AltAgency, he's helped over 800+ service providers build profitable, sustainable businesses by productizing their services and monetizing their expertise. Greg runs his 7-figure business working 3-4 days per week (most weeks), taking Fridays off for mountain biking, and wants to help others learn how to do the same. His unique approach helps owners ‘scale’ profits without scaling the complexity or sacrificing their lives.

Contact Greg: 

altagency.com

gregsvideos.com

In episode 102 of Agency Bites, I’m joined by Rena DeLevie—a leader and teacher who gets real about what it actually takes to show up fully and compassionately in today’s world. Yes, she’s got the corporate leadership chops and has been on a mission to end fear-based management, but what resonated most with me in this conversation was how personal and human her journey is.

Rena shares how, as someone with deep empathy and anxiety in her DNA, she learned to soothe her nervous system so she could show up with clarity and compassion—not just at work, but everywhere. We talk about the practices she leans on every day—meditation, breathwork, walking in the woods, connecting with nature, and even humor—as ways to ground herself and navigate stress, overwhelm, and tough decisions.

She’s lived through corporate toxicity, hard layoffs, and the pressure to “toughen up” as a leader. But instead of staying stuck in survival mode, she learned how to reconnect with herself, how to be present, and how to lead with kindness without losing her edge. 

This isn’t just a conversation about business—it’s about how we take care of ourselves so we can take care of others. It’s about slowing down enough to be intentional in how we speak, lead, and live. It’s about taking care of ourselves all ways, always. 

If you’ve been feeling stretched thin, reactive, or stuck in fight-or-flight mode, this episode will give you some simple but powerful ways to reset and recenter. Let’s get into it.

Key Bytes

• Compassion can radically transform agency culture and leadership.

• Fear-based management often leads to anxiety and burnout.

• Authenticity in leadership energizes both the leader and the team.

• Compassion and accountability must coexist in effective leadership.

• Daily meditation can help manage anxiety and foster self-awareness.

• Choosing yourself means prioritizing self-compassion and understanding.

• Humor can shift the energy of a toxic work environment.

• Compassionate leadership requires setting boundaries and not being a doormat.

• Navigating toxic environments often requires personal resilience and strategy.

• Modeling compassionate behavior can influence workplace culture positively.

Chapters

00:00 Introduction to Compassionate Leadership

01:15 The Shift from Fear-Based to Compassionate Leadership

04:06 The Energizing Power of Authenticity

10:00 Navigating Toxic Work Environments

12:56 Compassion and Accountability in Leadership

19:46 Daily Practices for Compassionate Living

25:52 Choosing Yourself: The Path to Self-Compassion

31:50 The Importance of Humor and Perspective in Leadership

Rena combines over 25 years with Fortune 500 companies and 20 years as a practitioner of mindfulness/meditation to show us the path to eliminating the fear-based culture so prevalent in

corporate America. Her book, Compassionate Management, How Ambitious Creatives Become Kick-Ass Leaders, and her TEDxTalk, Compassionate Management -- using compassion as a business tool has been used in businesses around the globe as a model to radically change leadership culture and how we treat one another.

Rena has given a TEDx Talk, presented at over 30 conferences, led over 60 workshops, and been on

dozens of podcasts. Rena is a high-energy presenter and interactively engages audience members to show compassionate leadership in action. This experiential approach empowers attendees to redefine their own leadership style and evolve their expectations of leadership culture.

Contact Rena on their website: renadelevie.com

In Episode 101 of Agency Bytes, I sit down with Kyra Cavanaugh, a wellbeing consultant, meditation coach, and Qigong instructor, for a conversation that feels like a deep breath in the middle of a hectic workday. We explore what it really means to prioritize wellbeing—not just for ourselves but for our teams and the people we lead.

Kyra shares practical, down-to-earth strategies for finding balance in a world that pushes us to hustle nonstop. We talk about how small, intentional moments of self-care can ripple into productivity, creativity, and stronger connections—both at work and in life. From recognizing when a teammate (or you) might need a breather, to breaking the cycle of “push through and crash later” culture, this episode is all about giving yourself permission to slow down in order to show up fully.

If you’ve ever struggled with burnout, felt the pressure to always be “on,” or wondered how to create a healthier, more human-centered workplace, this conversation is for you. Take a pause and join us.

Key Bytes

• Wellbeing is essential for productivity and creativity.

• Connection and mental health challenges have been prevalent for years.

• Daily self-care practices can help mitigate stress.

• Leaders must model wellbeing for their teams.

• Emotional intelligence is crucial in leadership.

• Establishing boundaries is key to healthy workplace relationships.

• Investing in oneself is a necessary practice.

• Simple check-ins can foster team connection.

• Recognizing the impact of personal struggles is important.

• Human connection should be prioritized in the workplace.

Chapters

00:00 Introduction to Wellbeing in the Workplace

05:55 Shifting Mindsets: From Work-Life Balance to Daily Wellbeing

11:48 Practical Strategies for Self-Care and Team Support

17:50 Emotional Intelligence in Leadership

23:50 Fostering Human Connection in the Workplace

Kyra Cavanaugh is a well-being consultant, meditation and healing coach, and Qigong instructor. She's worked with hundreds of businesses and thousands of leaders to improve personal, team and organizational well-being. She's an author, podcaster, speaker, coach and serial entrepreneur based in Asheville, NC where she loves to hike and listen to local, live music.

www.15Be.com

www.freeyourself.world

www.youtube.com/@freeyourselfworld

In the 100th episode of Agency Bytes, I couldn’t think of a more fitting guest to mark this milestone than the legendary Debbie Millman. As a designer, writer, educator, and the pioneering host of Design Matters, Debbie has shaped the creative industry in ways that continue to inspire me and so many others. In this conversation, we dive into her remarkable journey—from leading Sterling Brands to an Omnicom acquisition, to her impact on branding and design education, and even the evolution of her own 20-year podcasting career. She shares invaluable insights on leadership, overcoming rejection, embracing an abundance mindset, and finding inspiration in unexpected places. Plus, we discuss her upcoming book Love Letter to a Garden and the deeply personal connection between creativity and growth. It’s an episode filled with wisdom, warmth, and a celebration of resilience in the creative industry.

In this episode, we dig into:

• Debbie’s leadership at Sterling Brands and the journey to an Omnicom acquisition

• The evolution of Design Matters and what 20 years of podcasting has taught her

• How an abundance vs. scarcity mindset changed her creative path

• The impact of Milton Glaser’s mentorship and his powerful five-year vision exercise

• Advocating for women in design and her role in Omnicom’s Omniwomen network

• Dealing with rejection, imposter syndrome, and the realities of a creative career

• Her new book Love Letter to a Garden and the inspiration behind it

So, whether you’ve been here since episode one or you’re tuning in for the first time, thank you for being part of this journey with me. I sincerely hope you enjoy this special 100th episode of Agency Bytes with the one and only Debbie Millman!

Key Bytes

• Debbie became a shareholder at Sterling Brands in 1998.

• Leadership requires balancing financial acumen with creative passion.

• Debbie's management style was demanding yet fair.

• The acquisition by Omnicom was a pivotal moment for Sterling Brands.

• Debbie actively mentors and advocates for women in the industry.

• Her podcast, Design Matters, has evolved significantly over 20 years.

• Debbie's closing statement reflects her commitment to making a difference.

• The podcast has maintained a loyal audience despite industry changes. 

• Debbie's early writing for Armin Vitt's blog sparked her design journey.

• Milton Glaser's teachings on scarcity and abundance were transformative for Debbie.

• Writing a five-year plan helped Debbie visualize her future.

• Debbie emphasizes the importance of teaching and sharing knowledge.

• Rejections are a common experience, and feelings are temporary.

• Travel serves as a major source of inspiration for Debbie's work.

• Debbie's upcoming book combines her love for gardening and visual storytelling.

• Debbie encourages embracing both successes and failures in one's career.

• Believing in oneself is crucial for achieving goals. 

Chapters

00:00 Celebrating Milestones: The 100th Episode

12:37 Navigating Challenges in a Changing Market

18:06 Empowering Women in Creative Industries

24:42 The Evolution of Design Conversations

33:35 Navigating Rejections and Setbacks

42:05 Upcoming Projects and Personal Growth

Named “one of the most creative people in business” by Fast Company, “one of the most influential designers working today” by GDUSA, and a “Woman of Influence” by Success magazine, Debbie Millman is also an author, educator, designer, and podcast pioneer. Debbie is the host of the Webby and Signal award-winning podcast Design Matters, one of the first and longest-running podcasts in the world; Chair of the first-ever Masters in Branding Program at the School of Visual Arts, Co-owner and Editorial Director of PrintMag.com, and the author of seven books on design and branding. Debbie is the recipient of a Cooper Hewitt National Design Award and a Lifetime Achievement award from AIGA, the Professional Association for Design. She is currently a Harvard Business School Executive Fellow and was recently invited to the Design Advisory Board of Canva. 

Contact Debbie:

www.debbiemillman.com

branding.sva.edu

In episode 099 of Agency Bytes, I got to have our first-ever repeat guest: Kelly Campbell. Kelly is a trauma-informed leadership coach, author of Heal to Lead, and creator of The New TLC: Trauma, Leadership, and Consciousness on Substack. They aren’t just talking about leadership—they’re redefining what it means to be a leader in today’s world, starting from the inside out.

This conversation goes deep. We’re talking about the unspoken struggles that agency owners face—the hidden emotional baggage, the past experiences that shape how we lead, and why doing the inner work isn’t just self-care, but a leadership imperative.

Kelly shares how their own journey led to a radical shift in understanding leadership—not as a performance, but as an extension of our healing. We unpack why self-awareness is the foundation of trust, how compassion (not control) is the key to stronger teams, and why integrating past trauma is essential for leading with clarity and confidence.

We also get into:

• Why so many leaders struggle with reactivity, trust, and burnout—and how to break the cycle.

• The real difference between empathy and compassion (and why one is more effective in leadership).

• The danger of people-pleasing in leadership—when “being supportive” crosses into self-sacrifice.

• How agency leaders can create cultures of psychological safety, especially in uncertain times.

• Kelly’s bold decision to step away from LinkedIn for a year—and why they’re doubling down on deeper, more meaningful conversations on The New TLC.

• The agency landscape in 2025—why some agencies are thriving while others are struggling, and what owners need to focus on to stay ahead.

If you’ve ever felt like leadership was more exhausting than it should be—if you’ve questioned why certain situations trigger you, or if you want to create a more human, connected, and resilient agency culture—this episode will challenge you in all the right ways.

Kelly’s insights are game-changing, their wisdom is undeniable, and this conversation is one you don’t want to miss.

Key Bytes

• Publishing a book is a unique and challenging journey.

• The feedback from my book has led many to seek therapy.

• Vulnerability in leadership fosters trust and connection.

• Creating supportive environments is crucial for employee well-being.

• Compassionate leadership can reduce attrition and enhance collaboration.

• Personal experiences shape our leadership styles and effectiveness.

• Building community is essential for personal and professional growth.

• Experimenting with social media can lead to clearer boundaries.

• Daily practices can significantly impact overall well-being.

• Self-awareness is key to effective leadership.

Chapters

00:00 The Journey of Healing Leadership

06:30 The Creative Process of Writing a Book

12:00 Personal Growth Through Vulnerability

19:22 Navigating Leadership and Emotional Intelligence

23:44 Creating Supportive Work Environments

29:11 The Future of Leadership in a Changing World

33:12 Building Community and Personal Practices

39:53 Experimenting with Social Media and Boundaries

Kelly L. Campbell (they/them) is a Trauma-Informed Leadership Coach to emerging and established leaders who want to live, lead, and love with confidence and freedom. They are the author of HEAL TO LEAD: Revolutionizing Leadership through Trauma Healing. As a Sacred Trauma Healing practitioner, they work one-on-one with those who have experienced trauma in childhood or adulthood. Kelly has written for Entrepreneur, Fast Company and Forbes, and currently writes on Substack about “The New TLC: Trauma, Leadership, and Consciousness.” Their vision is for more than half of humanity to heal its childhood trauma so that we may reimagine and rebuild the world together.

Contact Kelly:

https://klcampbell.com

https://kellylcampbell.substack.com/

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

https://www.instagram.com/kelly.l.campbell/