Agency Bytes

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

Featuring: Ali Mirza, Rose Garden Consulting 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 on his personal website, his consulting website, or on his Instagram.

THIS EPISODE IS SPONSORED BY IGNITION. START YOUR FREE 14 DAY TRIAL ignitionapp.info/agencybytes-trial Use Code OUTSIGHT25 to save 50% off! Featuring: Sharon Toerek, Legal and Creative 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. Key Bytes • Most agencies don’t realize their biggest legal risks until a problem hits • Poor contracts quietly drain profit long before lawsuits happen • Scope creep is as much a legal issue as it is a pricing issue • IP ownership mistakes can create long-term client and valuation problems • Proactive legal structure is a growth advantage, not a cost center Chapters 00:00 Why legal blind spots are so common in agencies 04:15 The contracts agencies rely on (and why they fall short) 10:20 Scope creep as a legal and financial issue 18:05 IP ownership mistakes that come back years later 26:40 Client disputes: where agencies expose themselves 34:10 Risk vs. fear: what actually matters legally 42:00 Simple fixes agency owners can make now 50:10 How legal hygiene protects valuation and exit 56:30 Final thoughts & wrap-up 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: • agency-client relationships, including agency service contracts • agency-freelancer and agency strategic alliance relationship management • trademark and copyright protection, enforcement, and licensing • influencer marketing negotiations and content marketing legal compliance• advertising regulatory compliance • AI policy and risk management for agencies 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 • Created the Legal + Creative Agency Protection System, a comprehensive legal education and legal toolkit for marketing, ad and creative services agencies • Created and hosted over 300 episodes of the agency-focused podcast The Innovative Agency, a podcast about innovation and trends in the marketing agency world • Presents sessions on agency-critical legal topics to independent agency networks, to private agency audiences, and at industry conferences, including INBOUND, Content Marketing World, MAICON, the Build a Better Agency Summit, Own It Summit, Mirren New York, and PRSA Counselors Academy. Contact Sharon on LinkedIn or on their website.

THIS EPISODE IS SPONSORED BY IGNITION. START YOUR FREE 14 DAY TRIAL ignitionapp.info/agencybytes-trial Use Code OUTSIGHT25 to save 50% off!   Featuring: Amy Maxwell, Maxwell Design 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. Contact Amy on LinkedIn or on their website.

THIS EPISODE IS SPONSORED BY IGNITION. START YOUR FREE 14 DAY TRIAL ignitionapp.info/agencybytes-trial Use Code OUTSIGHT25 to save 50% off! Featuring: Meredith Fennessy Witts + Melissa Lohrer, Agency Darlings 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 broken 05:12 The origins of hustle culture in agencies 11:04 Masculine-driven leadership norms and their impact 17:32 Emotional intelligence as a growth lever 23:58 Building healthier agency cultures 30:41 Operator-led leadership vs. ego-led leadership 37:10 Sustainable growth without burnout 43:26 Redefining success as an agency owner 49:12 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.com https://bit.ly/MWDarlings https://waverlyave.com https://instagram.com/waverlyave.co https://www.lecheile.co/contact https://www.instagram.com/lecheile.co/

THIS EPISODE IS SPONSORED BY IGNITION. START YOUR FREE 14 DAY TRIAL ignitionapp.info/agencybytes-trial Use Code OUTSIGHT25 to save 50% off!   Featuring: Michael Janda, More Creative Academy 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. Connect with Michael through his Community, Instagram, YouTube, LinkedIn, Website, or explore his Courses.

THIS EPISODE IS SPONSORED BY IGNITION. START YOUR FREE 14 DAY TRIAL ignitionapp.info/agencybytes-trial Use Code OUTSIGHT25 to save 50% off! Featuring: Melanie Chandruang, We Consult 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. Key Bytes • Clean financials and clear reporting are the true foundation of scalable ops • Workflow ownership matters — if it’s nobody’s job, it’s nobody’s job • Founders stay bottlenecks when leadership has no autonomy or scorecards • Agencies with documented systems adopt AI faster (and with fewer messes) • Strong leadership = trust, clarity, and shared problem-solving • Self-care and boundaries are essential for sustainable agency ownership Chapters 00:01 Intro and how Melanie rebuilt WeConsult after kids and a cross-country move 02:48 Stepping away from client work, losing momentum, and clawing back into a changed industry 05:36 Why Melanie now stays high-level and pushes implementation to internal teams and automation 07:42 Founders as bottlenecks and what a truly strong leadership team looks like 11:15 Ego, scale, and the operational shifts required for owners to get out of the way 15:36 Where Melanie starts operationally: financials, workflows, and clear ownership 18:07 The agency financial metrics that actually matter (profitability, cash, utilization, and more) 22:03 Why documented systems are the key to successful AI adoption (and how messy it gets without them) 26:00 Leading through uncertainty, rebuilding a business, and protecting your own wellbeing 28:38 AI note-takers, imposter syndrome, and Melanie’s “value” practice 31:36 Melanie’s 90s karaoke pick and where to learn more about WeConsult 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.

THIS EPISODE IS SPONSORED BY IGNITION. START YOUR FREE 14 DAY TRIAL ignitionapp.info/agencybytes-trial Use Code OUTSIGHT25 to save 50% off! Featuring: Jordan Snider, Token Creative In episode 138, I sit down with Jordan Snider, co-founder and CTO of Token Creative Services, to break down the real impact of integrating Ignition App into their agency operations. Jordan shares how Token went from scattered proposals, manual invoices, and nearly $40k in aging AR to a streamlined, single-system workflow that clients actually appreciated. We dig into the operational before/after: centralized proposals and agreements, automated billing, faster close rates, clearer scope definition, easier upsells and renewals, and the elimination of unbilled “mystery hours.” Jordan also talks about forecasting clarity — and why dashboards that tie proposals, renewals, and revenue projections together are a game changer for decision-making. This episode is a grounded look at what happens when an agency stops tolerating a duct-taped sales and billing process and finally upgrades the operational spine of the business. Key Bytes • Token’s breaking point was nearly $40k in aging AR — a clear sign the proposal and billing process was broken. • Clients were confused by multiple proposal versions, scattered contracts, and manual payments; consolidating everything through Ignition simplified the entire client experience. • The biggest financial lift came from capturing previously unbilled variable hours and out-of-scope work. • Automated reminders and stored payment methods dramatically reduced AR and manual follow-up. • Forecasting became easier with visible open proposals, renewal pipelines, and year-over-year revenue projections. • Simplifying the tech stack cut both software cost and constant integration maintenance. • Ignition enabled Token to shift from hourly pricing to value-driven retainers because operations finally supported it. • Jordan’s advice: delaying this overhaul guarantees regret — proactively fixing it avoids the forced crisis moment. Chapters 00:00 Intro and why Token’s Ignition story matters 02:05 Token’s early days and “brute force” agency ops 03:10 The $40k AR wake-up call 05:10 What was broken in their proposal + onboarding workflow 06:55 Client reactions after switching to Ignition 07:50 Close rates, renewals, and handling scope creep 09:40 Capturing unbilled work and shrinking AR 11:55 Forecasting and metrics that changed decision-making 14:00 Simplifying the tech stack and ditching integrations 16:40 How clarity improved both scope and service delivery 23:40 Productizing services and shifting to retainers 25:05 Jordan’s advice for agencies resisting the overhaul 26:50 Rapid fire and wrap-up Jordan Snider is the Co-Founder and CTOof Token Creative Services, a full-service digital marketing and creative agency based in Kitchener-Waterloo. With a background in full-stack software engineering, Jordan bridges the gap between technical development and creative marketing. He has contributed personal reflections to platforms supporting victims of family violence, discussing the unique stressors faced by newcomers and the importance of community support systems. His work reflects a blend of technical precision and a commitment to social impact, aligning with Token Creative’s mission to support businesses making positive environmental or social changes. Connect with Jordan on their website, or learn more about Ignition here.

Featuring: Jennifer Spire, Preston Spire In episode 137, I sit down with Jennifer Spire, Partner and CEO of Preston Spire — a 75-year-old agency that’s somehow still pushing boundaries while many newer shops flame out. Jennifer shares how she modernized a legacy company without losing the cultural DNA that kept it alive for three-quarters of a century. We get into leadership transitions, building a values-driven agency, navigating generational shifts in talent, and how she’s shaping the next era of a Midwest powerhouse. Key Bytes • The hidden advantages legacy agencies have but often ignore • Why values act as a competitive moat — but only if they’re enforced • How Jennifer leads change without blowing up culture • The reality of modernizing 75-year-old processes • Where agencies underestimate the work of staying relevant Chapters 00:00 Intro 01:20 What it means to run a 75-year-old agency today 05:05 How Jennifer modernized Preston Spier without breaking it 09:40 The cultural DNA that actually drives retention 13:55 Why “values” only matter when leaders enforce them 17:48 Leadership evolution: from partner to CEO 21:30 What younger talent expects from an established shop 25:18 Staying relevant in a fast-changing industry 29:55 How Preston Spire balances legacy and innovation 33:42 Advice Jennifer wishes she had earlier 38:10 Closing thoughts Jennifer Spire is partner and CEO at Preston Spire, an Ad Age Best Place to Work and Midwest Small Agency of the Year. She is an accomplished agency leader with over 25 years of experience in both consumer and B2B marketing for just about every industry out there. At Preston Spire, Jennifer has played the leading role in reshaping the framework that defines the agency, focused on a strong vision, values and purpose. She has been a speaker at dozens of local and national conferences, has authored articles and thought pieces on various marketing subjects, and has been a board member of several nonprofit organizations. Jennifer was an east coast native before calling Minneapolis home. She was an NCGA gymnast and a gymnastics coach, who also had advertising in her blood, thanks to her grandfather being one of the founding fathers of Madison Avenue. Contact Jennifer on LinkedIn or the Preston Spire website.

Featuring: JP Holecka, Power Shifter Digital In episode 136, I sit down with JP Holecka, founder and CEO of Power Shifter Digital, a Vancouver-based agency leading the shift toward AI-driven digital products and content creation. With over 30 years of experience in design, film, and technology, JP has guided multiple teams through successful AI rollouts—transforming workflows, scaling creativity, and redefining how digital agencies deliver value. We talk about what it really takes to evolve your agency for the AI era, how to navigate the culture shift that comes with automation, and why embracing AI is less about replacing people and more about amplifying what they’re capable of. KEY BYTES • AI isn’t replacing creativity—it’s amplifying it • True transformation starts with changing workflows, not job titles • The most successful AI rollouts start with internal adoption before client delivery • Leadership has to model curiosity and experimentation • Agencies that treat AI as a tool, not a threat, are finding their competitive edge SHOW REFERENCES Access JP's AI Miro Board referenced in the episode here. PW: cleardigital CHAPTERS 00:00 Introduction 02:01 JP’s background and the evolution of Power Shifter 06:32 The first AI experiments that changed everything 10:45 Getting team buy-in and overcoming initial skepticism 14:58 Building processes around AI rather than forcing it in |20:10 Human creativity in the age of automation 25:36 How AI has changed client expectations 31:12 Leadership lessons from scaling an AI-driven agency 36:45 The next frontier of digital work 40:30 JP’s advice for agency founders starting their AI journey 43:00 Rapid Fire Questions JP Holecka is the founder and CEO of Power Shifter Digital, a Vancouver-based agency leading the shift toward AI-driven digital products and content creation. With over 30 years of experience in design, film, and technology, JP has guided multiple agencies through successful AI rollouts—transforming workflows, scaling creativity, and redefining how teams collaborate with generative tools. Contact JP on the PowerShifter website or on LinkedIn.