The Execution Gap Podcast
Episode #8:
Drew Cocco, VP of Client Experience at Clarity
In this episode of The Execution Gap, I sit down with Drew Cocco, VP of Client Experience at Clarity - a platform helping K-12 private schools simplify the complexities of modern school management. Drew brings a wealth of knowledge in strategic planning, leadership, and client experience, and we dig into what it really takes to scale with purpose.
In this episode we unpack:
🔹 Why having a customer support team of true subject-matter experts builds lasting trust with schools and families.
🔹 How communication and recurring Customer Success & Product syncs keep stakeholders aligned and backlogs healthy.
🔹 The challenge, and reward of breaking down department silos while scaling from 100 to 1,300+ schools.
🔹 How to connect the dots between employee goals, team goals, department goals, and mission.
🙏 A huge thank you to Drew for his time and for the great conversation. Thanks so much for coming on the show Drew!
📺 Watch the full episode: https://bit.ly/drew-cocco-podcast
Episode #9:
Zack Dugow - Founder & CEO the COOL company
This week’s guest, Zack Dugow - Founder & CEO the COOL company is living proof of what happens when you stay patient, stay resilient, and stay committed to incremental improvement over time.
When I asked Zack: “What’s one gap you’ve seen leaders struggle with most, and how do the top 10% close it?” His response - the top leaders:
🔹 Continuously push their leadership teams to level up
🔹 Welcome being challenged in return
🔹 Embrace discomfort as a driver of growth
🔹 Experiment with new processes (even knowing they won’t all work)
🔹 Understand that success is non-linear, it's full of cycles, dips, and breakthroughs
🔹 Look to downturns as opportunities to strengthen the business
If you’re a founder, CEO, or COO navigating global scale or acquisition - you will absolutely want to tune in.
🙏 Thank you so much to Zack for coming on the show - I really enjoyed our conversation and the valuable insight
📺 Watch the full episode: https://bit.ly/zack-dugow-podcast
Episode #10:
James Hatfield - Chief Revenue Officer at LiveSwitch
What do AI, a clogged drain line, and one mind-blown technician with a southern accent have in common? ...spoiler alert - Can I buy stock in your company? Trust me - you’ll never look at video + AI the same way again.
When I asked James about The Execution Gap he didn’t hold back - what’s one gap that you’ve seen time-and-time again, and how have you learned to close that gap, what advice would you give to other leaders who may be facing a similar gap?
🔹 Close the education gap - never stop learning, reading, or asking for help.
🔹 Build a board of advisors / mastermind - get around people who’ve already solved the problem.
🔹 Document what works so teams can scale without you.
🔹 Empower people closest to the data to make the decisions.
🔹 Beware of false prophets - find advisors who’ve actually done it.
This is one of my favorite episodes, and I'm extremely grateful to James for his time and for the great conversation. I would also like to thank Makenzie Schlegel for all her help. 🙏
Learn More About LiveSwitch:
▪️ Book a demo: https://bit.ly/liveswitch-book-a-demo
▪️ Website: https://www.liveswitch.com/
▪️ Start your free trial: https://www.liveswitch.com/contact-signup
▪️ Coupon: Use code "Apodaca10" for 10% off at checkout!
📺 Watch the full episode: https://bit.ly/james-hatfield-podcast
Episode #11:
Joseph Rutakangwa, Co-Founder & CEO of Rwazi
In this week’s episode, I sat down with Joseph Rutakangwa, Co-Founder & CEO of Rwazi - fresh off their $12M Series A in July - a major milestone for a company reshaping how enterprises collect ground-level market intelligence across emerging markets.
Joseph’s journey is impressive - he’s spent nearly a decade helping organizations move from data overload to decision clarity, designing systems that turn raw market inputs into insights - powered by SenaAI. He’s also the author of Never Stay Broke, where he breaks down the mindset and mechanics behind building financial resilience and long-term opportunity.
When I asked Joseph about The Execution Gap, he shared the patterns he sees most often inside fast-scaling teams and how the best leaders close those gaps:
🔹 Misaligned pace creates drag - teams moving at different speeds slow execution long before anyone notices.
🔹 Synchronicity beats raw speed - coordinated teams outperform fast ones.
🔹 Autonomy requires clarity - teams can only move fast when expectations and signals are unambiguous.
🔹 Insight > information - leaders must filter the noise before they act.
🔹 Growth is cyclical - the best organizations recognize cycles and adjust their tempo, not their mission.
This was a sharp, insightful conversation, and a must watch for any founder, operator, or leader scaling a fast-moving organization.
🙏 A huge thank you to Joseph for his time and for the great conversation. Thanks so much for coming on the show Joseph.
Learn More About Rawzi & Joseph:
▪️ Website: https://rwazi.com/
▪️ Never Stay Broke: https://bit.ly/never-stay-broke
📺 Watch the full episode: https://bit.ly/joseph-rutakangwa-podcast
Episode #12:
Camilo Navarro Bustos, Co-Founder
& COO of Wheel the World
In this week’s episode, I sat down with Camilo Navarro Bustos, Co-Founder & COO of Wheel the World - a company on a mission to make travel accessible for everyone - empowering people with disabilities to explore the world freely, safely, and confidently.
The origin of Wheel the World is rooted in friendship. After Camilo’s best friend and Co-Founder & CEO Alvaro Silberstein, became a wheelchair user at 18, they completed a history-making expedition across Patagonia. That journey exposed the barriers for people with disabilities, and uncovered how poorly designed the world is for those with accessibility needs.
Today, Wheel the World employs 75+ people and is reshaping travel for millions of seniors and travelers with disabilities. If you know anyone with accessibility needs, this is a must-listen.
When I asked Camilo about the The Execution Gap - a gap that he's seen time and time again, and what advice would he give to leaders facing a similar gap? He's answers were worth noting:
🔹 Scaling a mission requires ruthless focus
🔹 You must reduce noise so the team can stay anchored to the why
🔹 The work will test your patience more than your strategy
🔹 Discipline beats intensity
🔹 And OKRs only work when they’re cultural - not performative
This episode is deeply human and a powerful example "why". I am so grateful to Camilo for sharing his story and the mission of Wheel the World. 🙏
Learn More About Wheel the World:
▪️ Website: https://wheeltheworld.com/about-us
▪️ YouTube: youtube.com/@WheeltheWorld
📺 Watch the full episode: https://bit.ly/camilo-bustos-podcast
Episode #13:
Lucy Wang, VP of Product Marketing at Oleria
What happens when a seasoned product marketing leader with 20+ years across Disney, Microsoft Azure, AWS, and high-growth startups breaks down the truth about alignment, storytelling, and execution?
This week, I had the privilege of speaking with Lucy Wang, VP of Product Marketing at Oleria, a company delivering next-generation identity security on a modern, reliable platform. Lucy’s background is remarkable - engineering at Disney, GTM leadership across cloud + AI, and now shaping product marketing at one of the most exciting security startups in the space.
This episode is packed with leadership and go-to-market insights for PMMs, PMs, founders, and anyone operating inside a fast-moving GTM environment.
When I asked Lucy about The Execution Gap, here’s what she said:
🔹 Strategy, execution, and communication must stay consistent - or your “apple becomes an orange.”
🔹 Communication is the bridge - assumptions are the breakage.
🔹 Sales + Marketing must share feedback loops - not build competing narratives.
🔹 Leaders must become “practitioners of simplicity.” If your message can’t be repeated by your grandma, it's too complex.
🔹 Teams waste time when their daily work doesn’t tie back to company priorities - clarity cuts noise.
🙏 I'm deeply grateful to Lucy for her time and for the great conversation and insights. Lucy - thank you so much for coming on the show!
Learn More About Oleria:
▪️ Website: http://www.oleria.com
▪️ Lucy's Article: https://lnkd.in/gXHmxEsE
📺 Watch the full episode: https://bit.ly/lucy-wang-podcast