What happens when you walk away from security and take the leap into the unknown? In this episode, Jason Di Vece, Co-Founder of Bytes.co, shares how selling everything to move abroad reshaped his mindset and set him on the path to building a 25-person agency serving hundreds of clients. 

Key Takeaways

• The risky move that built lasting confidence and shaped Jason’s entrepreneurial journey
• Why hiring mistakes can cost years
• Hard decisions every agency leader must face (and why the hardest ones are usually right)
• How rethinking failure can open the door to innovation and growth

Company: Scratch Media + Marketing

Guests: Ryan Ellis

Year Started: 2009

Employees: 26-50

What happens when an agency depends too much on its founder? In this episode, Lora Kratchounova, Founder of Scratch Marketing and Media, shares how she built a 40-person B2B tech agency by shifting from founder-dependence to team empowerment. From mastering positioning to embracing deep tech and climate tech, Lora’s story highlights an ever present learning mindset and team focused leadership.

Key Takeaways

• The “school bus test” what is it and why it matters
• The role of positioning as the most critical agency “hack”
• How empowering your team leads to better leadership and client results
• Why primary data and customer insight outperform assumptions
• A lesson in climate tech and passion

Company: Red Egg Marketing

Guests: Ryan Ellis

Year Started: 2011

Employees: 11-25

Growing an agency doesn’t always come from chasing the newest trends, it often comes from mastering the basics. In this episode, Ryan Ellis, Founder of Red Egg Marketing, shares how focusing on client relationships, intentional growth, and sticking to fundamentals helped him build a business that lasts. 

 Key Takeaways

• How low expenses gave Ryan the freedom to experiment and gain experience
• Why retention and consistency matter more than chasing quick wins
• The overlooked value of knowing when to let go of the wrong client

Company: AOR

Guests: Alyssa Ash

Year Started: 2011

Employees: 25-50

What if your journey to owning an agency started without you even knowing it? In this episode, Alyssa Ash, Partner at AOR, shares how she went from junior designer to co-owner of a leading creative and digital agency. You’ll hear the behind-the-scenes story of a years-long leadership transition, the lessons learned along the way, and how she’s navigating an unpredictable business landscape.

Key Takeaways

• How to spot and develop future leaders from within your team
• Why a long runway is essential for a smooth ownership transition
• The role of curiosity and initiative in creating career-defining opportunities
• How to lead confidently while still embracing discomfort
• An insider’s perspective on what it takes to transition from team member to owner

Company: Cro Metrics

Guests: Gwen Hammes

Year Started: 2011

Employees: 50-100

Gwen Hammes, Co-CEO of Cro Metrics, shares her journey of taking over leadership, not by replicating the past, but by evolving it. In this episode, Gwen shares what happens when you step into a founder’s shoes and choose to grow the team before the business.

Key Takeaways

• The biggest risk in leadership transitions
• Why growing your people first leads to better client outcomes
• The “micro-step” mindset that unlocks clarity in career growth
• A creative approach to training the team
• How to build a leadership structure that complements, not competes

Company: 118 Group

Guests: Dylan Steven

Year Started: 2017

Employees: 1-10

The Secret to a Smarter, Stronger Team? Build a Learning Culture
What if the best agency investment isn’t more tech or tighter processes, but more learning? In this episode, Dylan Steven of 118Group shares how embedding education and autonomy into his team’s DNA has elevated their work and strengthened their connection. He unpacks how letting go of control actually led to better outcomes and why systems should support people, not restrict them.

Inside this episode:

• How a team book club turned into a powerful cultural cornerstone
• The subtle difference between structure and rigidity and why it matters
• The one shift that helped Dylan take a real vacation without disruption
• The journey of building autonomy without losing consistency
• Dylan and Russel make the case for shorter books. 

Company: Bubbly Creative

Guests: Cara Chatellier

Year Started: 2020

Employees: 1-10

When your brand is an extension of who you are, the work becomes deeply personal and powerful. In this episode, Cara Chatellier, founder of Bubbly Creative, shares how she built a values-driven agency that puts relationships first and strives to deliver marketing that actually connects. If you're tired of generic content and ready to build something more authentic, this one's for you.

Episode Highlights

• Why saying yes to everything early on creates long-term problems
• The hidden cost of generic marketing, especially in the age of AI
• A simple but effective approach to building trust through brand authenticity
• How knowing your own values makes it easier to attract the right clients

Company: Perspektiiv Design Co

Guests: Alison Gardner

Year Started: 2014

Employees: 1-10

What if building your agency meant more boundaries, not more burnout? In this episode, Alison Gardner, Founder of Perspektiiv Design Co, shares how she transformed her solo design practice into a collaborative agency without sacrificing her creativity, identity, or personal life. You'll hear how she built a system that supports her, even through major life changes like motherhood.

Key Takeaways

• Why documenting and delegating specific roles is key to stepping out of day-to-day work
• How to use slow seasons to strengthen systems, processes, and relationships
• What it really takes to trust your team and build autonomy
• A repeatable method to evaluate what to remove, automate, delegate, or own in your business
• The power of running a business with joy as your focus. 

Company: Mad Mind Studios

Guests: Omid Mousaei

Year Started: 2008

Employees: 11-25

What does it take to build a creative agency from nothing…without connections, experience, or a safety net? In this episode, Omid Mousaei of Mad Mind Studios shares how his journey from immigrant to agency founder shaped the values, mindset, and grit behind his business. If you've ever faced setbacks or felt alone in the chaos of agency life, this episode will remind you you're not the only one and that grit can become your greatest asset.

Inside this episode:

• Why betting on yourself with a have to is often the most strategic move you can make
• The overlooked mindset shift that changes how clients perceive value
• What AI can and can’t replace in creative strategy
• Why comfort is the enemy of creativity

Company: Upswept Creative

Guests: Sarah Giffrow

Year Started: 2011

Employees: 1-10

What if staying un-niched was your more niche than you think? In this episode, Sarah Giffrow of Upswept Creative shares why she chose variety over specialization, and how it’s helped her build a values-driven agency that aligns with who she is. From helping mission-focused clients to overcoming the challenge of marketing her own business, Sarah offers honest insights agency owners can relate to.

Key Takeaways

• How there are many forms to niching, including just being your authentic self
• How to align your marketing voice with your values (without turning off ideal clients)
• A practical way to carve out time for your agency’s own brand work