What happens when a real estate leader starts thinking 10 years ahead instead of just one deal at a time? In this episode of Closing the Coast, Dillon Staples sits down with Jim Walberg, founder of The Bay Area Team, to talk about what it really looks like to build a legacy—and how he’s planning a graceful exit from the business he’s spent years creating.

Jim shares his thoughts on succession planning, brand trust, and why creating a transition framework isn’t just a “someday” task, it’s a now task. This episode is packed with insight for any agent, team lead, or entrepreneur thinking about how to make their business outlive their own involvement.

Key points discussed:

• How Jim and The Bay Area Team are planning for long-term success and succession
• Why transferring client trust is the most valuable part of an exit strategy
• The structure behind their transition plan, and why it’s unlike anything in real estate
• What legacy-building really means in a people-first business
• Why intentionality drives everything from client service to future planning
• Jim’s offer to share their transition framework with other team leaders

Connect with Dillon:

• LinkedIn: https://www.linkedin.com/in/dillon-staples
• Compass: https://www.compass.com/agents/dillon-staples/
• Instagram: https://www.instagram.com/dillon_staples/

Connect with Jim Walberg: https://www.thebayareateam.com/

*Content from this podcast is provided for information and education purposes only, and is not intended as a substitute for actual financial or entrepreneurial advice.

Closing The Coast is produced by Stillwater Studio.

What happens when you hit rock bottom and decide to bet on yourself? In this episode of Closing the Coast, Dillon Staples sits down with Michael Melicia, Founder & CEO of Coastal Paving & Excavating, to talk about how he went from a $500 junkyard truck (and a screwdriver ignition!) to running a $20 million company in just seven years.

Michael gets real about overcoming addiction, why daily habits changed everything, and how he’s mentoring entrepreneurs today to help them scale, without the fluff. If you’re tired of the overnight success BS, this episode delivers the raw truth about building something that lasts.

Key points discussed:

• The wild story of how Michael started Coastal Paving with $500 and a junkyard truck
• How beating addiction taught him discipline and why daily habits are non-negotiable
• What it really takes to scale a business (hint: it’s not a get-rich-quick course)
• Why Michael chose mentorship over coaching and how he’s helping others grow faster
• The power of showing up daily even when nobody’s watching
• How authentic social media presence has helped his brand (and why he doesn’t care if it’s not polished)
• Michael’s big vision for the next 5 years (including the private jet goal!)

Connect with Dillon:

• LinkedIn: https://www.linkedin.com/in/dillon-staples
• Compass: https://www.compass.com/agents/dillon-staples/
• Instagram: https://www.instagram.com/dillon_staples/

Connect with Michael Melicia: https://linktr.ee/michael_a_melicia

*Content from this podcast is provided for information and education purposes only, and is not intended as a substitute for actual financial or entrepreneurial advice.

Closing The Coast is produced by Stillwater Studio.

What happens when you get banned from Target returns but end up creating something incredible? Today we're sitting with Erin and Matt Conway of Kismet House, who flipped their lives upside down when they bought "the house nobody wanted." Their story proves that sometimes the craziest decisions lead to the best outcomes - from Matt leaving firefighting to them becoming major players in design and content creation.

Key points discussed:

• The wild story of how they landed their first house - and why the listing agent laughed at their offer
• That time Erin got banned from Target returns (yes, really) while trying to create content
• How Matt went from fighting fires to becoming a full-time renovation expert
• Why taking the "wrong" route home led to finding their dream Victorian
• The real truth about content creation (it's not all pretty photos and perfect moments)
• Their unexpected path from UpTick Interiors to Kismet House
• Why removing fear of failure changed everything for them
• How authenticity beat algorithm-chasing in building their community

Connect with Dillon:

• LinkedIn: https://www.linkedin.com/in/dillon-staples
• Compass: https://www.compass.com/agents/dillon-staples/
• Instagram: https://www.instagram.com/dillon_staples/

Connect with Erin and Matt Conway:https://linktr.ee/kismet_house

*Content from this podcast is provided for information and education purposes only, and is not intended as a substitute for actual financial or entrepreneurial advice.

Closing The Coast is produced by Stillwater Studio.

What drives success in luxury real estate during challenging market conditions?

In this enlightening episode of Closing the Coast, host Dillon Staples sits down with Charlotte Gannaway, his business partner and veteran real estate agent, to discuss the evolution of luxury real estate in the Carmel-Monterey Peninsula market. They explore how their team achieved substantial growth despite market uncertainties, and share insights into their unique approach to marketing heritage properties.

Key points discussed:

• Charlotte shares her 16-year journey in Carmel real estate and the formation of the Staples Gannaway team, highlighting their transition from Weathers Gannaway to a new era in luxury real estate 
• Deep dive into their boutique approach to luxury properties, emphasizing how their focus on storytelling and heritage properties sets them apart in the market
• Fascinating case study of the Yankee Beach Way property, revealing the 18-month journey from listing to sale and the detailed process behind marketing unique luxury homes
• Discussion of their innovative marketing strategy, particularly their approach to property videos that showcase lifestyle rather than just static home tours
• Analysis of the 2023-2024 market dynamics, including insights on how low inventory and interest rates have impacted the Carmel real estate landscape
• Expert perspective on the 2025 market outlook, with predictions about inventory levels and pricing trends in the Carmel-Monterey Peninsula area
• Valuable advice for buyers and sellers: focus on timing and personal needs rather than trying to strategically time the market

Connect with Dillon:

• LinkedIn: https://www.linkedin.com/in/dillon-staples
• Compass: https://www.compass.com/agents/dillon-staples/
• Instagram: https://www.instagram.com/dillon_staples/

Connect with Charlotte Gannaway:

• LinkedIn: https://www.compass.com/agents/charlotte-gannaway/
• Instagram: https://www.instagram.com/charlotte_gannaway/
• Website: https://staplesgannaway.com/

*Content from this podcast is provided for information and education purposes only, and is not intended as a substitute for actual financial or entrepreneurial advice.

Closing The Coast is produced by Stillwater Studio.

Ever wondered how two sisters turned their family's recipes into a viral social media success with over 400,000 followers? Join us as we sit down with Maddie and Julia from Kitchen by the Sea, who reveal how they transformed their passion for baking into a thriving social media business while maintaining their full-time careers. This episode offers a candid look at the realities of content creation, brand partnerships, and staying authentic in the digital space.

Key points discussed:

• How Kitchen by the Sea grew from zero to 400,000+ followers on both Instagram and TikTok in just 2.5 years
• The surprising revelation that a single 5-second reel can take 30 minutes of footage and 20+ takes
• How their mother's recipes became their most viral content, including their first breakthrough hit with pumpkin chocolate chip bread
• Their journey of slowing down content production to maintain higher quality standards
• The detailed process of creating authentic collaborations and maintaining creative control
• Managing Kitchen by the Sea as their "5 to 9" while maintaining successful full-time careers
• How they learned to divide responsibilities based on their individual strengths
• Their approach to maintaining a positive social media presence and engaging with followers
• Their commitment to testing recipes multiple times before sharing
• Posting daily content for over a year to build their following
• Their openness about failed attempts and learning experiences

Connect with Dillon:

• LinkedIn: https://www.linkedin.com/in/dillon-staples
• Compass: https://www.compass.com/agents/dillon-staples/
• Instagram: https://www.instagram.com/dillon_staples/

Connect with Maddie and Jules:

• Website: https://kitchen-by-the-sea.com/
• Instagram: https://www.instagram.com/kitchen_bythesea/

*Content from this podcast is provided for information and education purposes only, and is not intended as a substitute for actual financial or entrepreneurial advice.

Closing The Coast is produced by Stillwater Studio.

What does it really take for young entrepreneurs to succeed in the luxury market? In this inaugural episode of Closing the Coast, host Dillon Staples sits down with Jonathan and Jessica Hugo, founders of a successful luxury media production company. They share their journey from starting their wedding videography business at age 19 to becoming sought-after luxury brand collaborators, revealing how they overcame age bias and built their distinguished portfolio through strategic value creation and unwavering commitment to quality.

Key points discussed:

• From wedding videography to luxury partnerships: How the Hugos built multiple successful media brands
• The power of solving problems: Why chasing money isn't the path to success
• Overcoming age bias: Converting youth into a competitive advantage
• The value proposition in luxury markets: Why it's about abundance of value, not just high prices
• Real estate as a creative outlet: How media production skills translate to property development
• The importance of quick, quality experience building vs. "putting in your time"
• Creating the Stillwater Studio: Identifying and filling a gap in high-end podcast production
• The mindset shift: Focus on value creation instead of money generation
• Building sustainable success through problem-solving rather than exploitation
• The power of taking the first step: Why action beats perfect planning
• Time vs. Money: How young entrepreneurs can leverage their greatest asset

Connect with Dillon:

• LinkedIn: https://www.linkedin.com/in/dillon-staples
• Compass: https://www.compass.com/agents/dillon-staples/
• Instagram: https://www.instagram.com/dillon_staples/

Connect with Jonathan and Jessica Hugo:

• Hugo Film Co.: https://hugofilm.co
• 17th & Ocean: https://17thandocean.com

*Content from this podcast is provided for information and education purposes only, and is not intended as a substitute for actual financial or entrepreneurial advice.

Closing The Coast is produced by Stillwater Studio.