Agency Bytes

Ep 107 – Blair Enns, Win Without Pitching – The Fourth Conversation

Featuring: Blair Enns, Win Without Pitching

In episode 107 of Agency Bytes, I sit down with Blair Enns, founder of Win Without Pitching and author of The Win Without Pitching Manifesto and The Four Conversations. If you’ve heard Blair on other shows—or are one of the many who’ve followed his work for years—you might think you’ve heard it all. Not this time. In this conversation, we go beyond the usual talking points and uncover insights he’s never shared before.

Blair opens up about the real mindset shifts creative professionals need to make if they want to stop selling like vendors and start showing up as experts. We break down the Four Conversations model, what most agency owners still get wrong about pricing, and how to rewrite the dynamics of the sales process to work in your favor.

We also explore why repetition beats inspiration, how to protect your power in client engagements, and what Blair believes is the single biggest opportunity for agencies right now—even in a time of AI disruption and economic uncertainty. If you want to charge more, pitch less, and finally own your value—this episode brings the fire.

Key Bytes

• Blair Enns emphasizes the importance of lifestyle choices in career decisions.
• The Win Without Pitching Manifesto serves as a foundational text for creative professionals.
• Sales should be viewed as a series of conversations rather than a pitch.
• Pricing is a critical area for agencies to improve profitability.
• Repetition in learning is essential for mastery of sales techniques.
• Creative professionals often struggle with the mindset of being a salesperson.
• The Four Conversations provides a framework for navigating sales effectively.
• Surviving economic uncertainty is crucial for agency success.
• Agencies should focus on their unique expertise to stand out in the market.
• Building strong client relationships is key to successful sales.

Chapters

00:00 Introduction to Blair Enns and His Journey
02:59 The Catalyst for Change: Lifestyle Choices
06:00 The Birth of Win Without Pitching
09:06 Understanding the Win Without Pitching Manifesto
12:12 The Four Conversations: A New Model for Selling Expertise
17:54 Lessons Learned from Coaching Agencies
20:50 The Importance of Repetition in Learning
25:56 Navigating Sales Conversations Effectively
31:59 Mindset Shifts for Creative Professionals
35:05 Opportunities and Challenges Ahead for Agencies

Blair Enns is the founder of Win Without Pitching and the author of three books on selling and pricing for expert advisors and practitioners, including the brand new The Four Conversations: A New Model for Selling Expertise.

A former advertising professional and consultant, Blair launched Win Without Pitching in 2002 to help creative professionals learn to win more business at higher prices without giving their services away for free in a pitch. His selling philosophy and pricing strategies resonated beyond the advertising and design professions to the point where today Win Without Pitching serves expert advisors and practitioners around the world in over a dozen professions, including finance, marketing, consulting, engineering and healthcare.

Blair also co-hosts, along with David C. Baker, the popular podcast 2Bobs: Conversations on the Art of Creative Entrepreneurship.

Contact Blair on winwithoutpitching.com.

Ep 106 – Lisa Colantuono, AAR Partners – Building Relationships, Not Pitches

Featuring: Lisa Colantuono, AAR Partners

In episode 106 of Agency Bytes, I chat with Lisa Colantuono, president of AAR Partners and a 25-year veteran in agency-client matchmaking (though she hates that word!). If you’re tired of wasting time on endless pitch decks, spec work, and one-sided RFPs, this episode is a must-listen.

Lisa shares what really matters to brands during the agency search process—and how agencies can proactively position themselves to win more work without chasing every lead. We dive into how to build trust that leads to long-term relationships, how to get your agency noticed through smart PR, and why your creative work still needs to deliver real impact. Lisa also drops actionable advice on reputation-building, client retention, and what it really takes to stand out in a crowded agency landscape.

Whether you’re running a small shop or a growing firm, Lisa’s insights are full of practical steps to help you stay relevant, get on the right shortlists, and keep your agency’s name in the room—even when you’re not.

Key Bytes
• Streamlining the agency review process is essential—both for marketers and agencies trying to avoid wasted time and energy.
• Marketer-led reviews now make up 85% of the search landscape—agencies need to understand how to stand out in this evolving dynamic.
• Trust and relationships are everything. People buy from people they trust, and lasting partnerships are built on emotional connection.
• Agencies must treat themselves like their number one client. Prioritize your own marketing, just like you would for your best-paying account.
• Referrals, recognition, and press coverage are key to visibility—smart PR can put your agency on a brand’s radar before the pitch even starts.
• Great creative still wins. No amount of charm or strategy can replace standout work that delivers results.
• Proactivity beats complacency. The biggest reason agencies lose clients? They stop showing up with ideas.
• Personalized outreach beats “spray and pray.” Insightful, relevant communication gets attention—generic blasts get ignored.
• Your network defines your success. The company you keep, the connections you nurture—they’re all part of the relationship-driven business we’re in.

Chapters
00:00 Introduction to Agency Bites and Lisa Colantuono
01:44 Reinventing the Agency Search Process
04:21 Streamlining the Review Process
08:11 Trends in the Marketing Industry
12:26 Building Trust and Relationships in Agencies
18:10 The Importance of Reputation and Press Coverage
23:28 The Power of Recognition in Agency Work
25:06 The Importance of Account Management
26:39 Complacency: The Silent Account Killer
28:07 Proactivity in Client Relationships
29:33 Building Trust Through Networking
30:56 Emotional Connections with Brands
32:55 The Value of Insightful Communication
35:05 Understanding Client Pain Points
39:19 The Comprehensive Marketing Approach
40:09 Personal Insights and Life Lessons

Lisa Colantuono is the President of AAR Partner. With nearly 25 years of experience, Lisa has helped marketers like Ancestry, Subaru, and Panera Bread connect with the right agencies to drive meaningful results. She’s a pioneer in modernizing the agency search process, the author of @AARLisa: New Biz in 140 Characters (or Less), and the host of the On Purpose podcast. Lisa is passionate about building impactful partnerships and shaping the future of the marketing industry.

Contact Lisa on their website or on LinkedIn.

Ep 105 – Ryan Rhoten, The Distilled Brand – Messaging That Converts

Featuring: Ryan Rhoten, The Distilled Brand

In episode 105 of Agency Bytes, I’m joined by Ryan Rhoten, founder of The Distilled Brand, who helps entrepreneurs and agency owners develop crystal-clear messaging that actually connects. Ryan shares the structured process he’s refined to help business leaders articulate their value—not with jargon or vague promises, but with messaging that speaks to real human emotion and need.

We dig into his “four O’s” framework, why niching is essential (even if you resist it), and how standardizing your offers can streamline operations, boost profitability, and make your marketing 10x easier. If you’ve ever felt like your agency’s message isn’t landing or you’re reinventing the pitch every time you meet someone new, this episode is for you.

Key Bytes
• Ryan helps entrepreneurs align their internal expertise with external perceptions.
• Messaging should address both objectives and the emotional obstacles clients face.
• The Four O's: Objectives, Obstacles, Objections, and Outcomes are crucial for effective messaging.
• A messaging playbook provides a structured approach to communication across all platforms.
• Niching down helps entrepreneurs become known for their expertise.
• Standardizing offers can lead to increased efficiency and profitability.
• Clear messaging is essential for team alignment and customer understanding.
• Customers are primarily concerned with their own needs, not your company's history.
• Effective messaging should focus on benefits rather than features.
• Incremental improvement is key to long-term success in business.

Chapters
00:00 Introduction to Agency Bites and Guest Ryan Roten
02:26 Understanding Brand Messaging and Positioning
05:44 The Emotional Side of Messaging
09:16 The Four O's of Messaging
12:40 Creating a Messaging Playbook
15:01 The Importance of Niching Down
18:42 Standardizing Offers for Efficiency
20:22 Crafting a Clear Elevator Pitch
22:04 Identifying Red Flags in Messaging
25:05 Rapid Fire Questions and Closing Thoughts

Have you ever struggled to communicate your expertise in a way that truly resonates? Ryan Rhoten, owner of The Distilled Brand, understands the challenge and has developed the Brand Messaging System to help. As an expert in brand positioning and messaging, Ryan guides his clients through a proven process to distill complex ideas into clear, compelling messages to communicate your brilliance and connect with your audience.

Contact Ryan on his website or on LinkedIn.

Ep 104 – Adam Nathan, Blaze.ai – AI for Agencies

Featuring: Adam Nathan, Blaze.ai

In episode 104, I sit down with Adam Nathan, the CEO and co-founder of Blaze.ai, the AI-powered marketing tool that’s making big waves—especially for small teams. Adam and I get into his wild journey of scaling Blaze to over $10 million in revenue in just 15 months with a lean team of 25. We talk about how AI is no longer just for the big guys—it’s helping small businesses, solopreneurs, and yes, even agencies, punch way above their weight.

We also explore some of the trickier topics like AI’s ethical impact, the looming question of government oversight, and even the ecological footprint of AI technology. Adam shares some powerful stories from real users—including how one guy was finally able to take a vacation after 13 years because Blaze gave him time back. Whether you’re excited or anxious about AI, this conversation is packed with useful insights—and a refreshing take on where the future of marketing might be heading.

Key Bytes
• Adam Nathan's entrepreneurial background influenced the creation of Blaze.
• Blaze serves as a virtual marketer for small businesses.
• AI helps small businesses produce high-quality content efficiently.
• Many small businesses were previously doing little to no marketing.
• AI allows small businesses to compete with larger companies.
• The impact of AI on marketing is largely positive for small businesses.
• Agencies can scale their client base using AI tools like Blaze.
• Ethical considerations around AI usage are important for agencies.
• Government oversight should focus on outputs rather than inputs.
• The ecological impact of AI may decrease as technology advances.

Chapters
00:00 Introduction to Blaze and Adam Nathan's Journey
03:00 The Need for AI in Marketing
06:02 Blaze's Rapid Growth and Team Structure
08:54 AI's Impact on Small Businesses vs. Large Corporations
11:54 The Role of AI in Marketing and Content Creation
14:48 Ethics and Disclosure in AI Usage
17:57 The Future of Work and AI's Role
20:59 Government Oversight and Ecological Impact of AI
24:05 Final Thoughts and Rapid Fire Questions

Adam Nathan is the CEO and co-founder of Blaze, the #1 marketing AI tool for teams of one.

Get Blaze CEO Adam Nathan's cheat codes to building and growing a $150M company in your inbox every week with Startup Tycoon. Powered by Adam's experience shipping product to millions, raising $46M, and hyperscaling to $7M+ in revenue in 15 months with only 25 people.

Learn about Blaze.ai or subscribe to Startup Tycoon.

Ep 103 – Greg Hickman, AltAgency – Simplify, Productize, Scale

Featuring: Greg Hickman, AltAgency

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 on his website or his YouTube channel.

Ep 102 – Rena DeLevie – Mindful Leadership

Featuring: Rena DeLevie

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.

Ep 101 – Kyra Cavanaugh, Free Yourself – Workplace Wellbeing

Featuring: Kyra Cavanaugh, Free Yourself

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.

Contact Kyra on 15be.com, freeyourself.world, or on their YouTube channel.

Ep 100 – Debbie Millman – Lessons in Leadership, Design, and Abundance

Featuring: Debbie Millman

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 on their website or through the SVA Branding program.