March 28, 2025Suneet sits down with Maui real estate icon Dano Sayles, the founder and CEO of The Sayles Team. With over 41 years in the business and a luxury portfolio that includes billionaire enclaves in Makena, Dano shares how he built—and rebuilt—a thriving real estate business that aligns with his values of personal freedom, wellness, and global adventure. From representing artisan-crafted estates to mentoring the next generation, Dano reveals how he reignited his passion, scaled into the ultra-luxury segment, and how the Reside community played a pivotal role in his resurgence. If you’re a growth-minded team leader or broker looking for sustainability, lifestyle balance, and next-level results—this is the episode you don’t want to miss.
Chapters:
- 00:00:00 – Welcome to the Island Vibe: Suneet kicks things off
- 00:00:23 – Meet Dano Sayles: Maui’s Luxury Real Estate Leader
- 00:00:54 – How a California Kid Built a Real Estate Empire in Paradise
- 00:02:11 – From Burnout to Breakthrough: Rekindling Passion After 40 Years
- 00:03:26 – Selling Paradise: Inside Maui’s Ultra-Luxury Market
- 00:05:24 – Leading the Sayles Team: Family, Focus, and High Performance
- 00:07:50 – Letting Go to Level Up: Why Delegation Fuels Growth
- 00:08:21 – Unleashing Potential: Dano’s Life-Changing Tony Robbins Experience
- 00:13:56 – Centered and Grateful: Meditation, Mindset, and Morning Rituals
- 00:15:31 – Marketing with Aloha: Leveraging Tech to Elevate Brand Presence
- 00:19:41 – Dano’s Wisdom Drop: Advice for Agents and Vision for What’s Next
- 00:22:16 – Closing Words: Connect with Dano and Keep the Fire Lit
Links and Resources:
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Episode breakdown: rebuilding a luxury team in Maui
Dano Sayles moved to Hawaii in 1984 and is in his 41st year selling real estate there. He leads the Dano Sayles Team on Maui with his son Anthony, and he joined the Reside community at the end of 2024 after a market shift pushed him to step back into the team leader seat. In this conversation with Suneet Agarwal, he explains how he hired, delegated and rolled out new systems while most of his local competitors were cutting back.
Learn the assistant’s job before you hire the assistant
Anthony joined the business full time in 2008, straight out of the University of San Diego, and has been with Dano for about 17 years. On day one he asked where their assistant was. Dano’s answer was that Anthony would do that job himself first, so he’d know every part of it before anyone else was hired.
You are the assistant until you can learn everything that the assistant would do, so you can actually train them.
Dano Sayles
About a couple of years later the team made its first hire, Michael, who has now been with Dano close to 15 years. Because the person doing the training had already done the work, the role came with a trainer who knew it from the inside.
Train your successor before you step away
In 2014 Dano wanted to spend a year traveling and learning from Tony Robbins. Anthony told him he wasn’t ready to run the business yet. It took about three years of preparation before Anthony said he was, and by then he was well prepped and Michael was in place. That groundwork is why Dano can delegate to both of them today.
He’s still adjusting the structure. Through his coaching with Mie Yamashita, the team has been doing lane exercises to get everybody in the right seat. Michael has been the director of marketing and Anthony the director of operations, and those titles may change. Dano’s son Alex handles content creation. With that bench behind him, Dano is now building a new team on Oahu focused on 40-story high-rises, starting from scratch with no listings and no buyers.
Roll out one system at a time
After joining Reside, the team installed its new stack in sequence rather than all at once. Follow Up Boss was running by the end of January and the Sierra site by the end of February, with another marketing tool scheduled for the end of March and a direct-marketing partner after that. Dano made that investment while many agents in his market were cutting their spending across the board. His bet is that better systems will help the team serve clients and attract more buyers, sellers and team members.
He doesn’t call himself the tech person on the team. He does see it as his job to know what’s available, which means reading, learning and asking other team leaders what’s working for them, then handing the rollout to his people. His rule for what to automate is simple.
If you’re gonna do anything more than one time, as many things as you can get automated, the better it is for your systems.
Dano Sayles
Know more than the buyer does
About 15 years ago the team moved from new-home neighborhoods into Maui’s resort and luxury market. Those clients are often buying their second, third or fourth home, and many pay cash. In the year before the interview, inventory grew in every segment and prices dropped significantly, so the team is working to find where the market actually is.
Dano remembers pagers, fax machines and printed MLS books that agents guarded as proprietary. Today, he says, buyers are well informed through technology before they even land on the island. His conclusion is that an agent selling real estate has to know more than the consumer, and technology is how the team stays ahead of very sharp buyers.
Build coverage so the team keeps its balance
Asked what he’d tell his younger self, Dano said he spent too many years working seven to seven, seven days a week, with blinders on. He doesn’t want his team repeating that. Most of his team members have young children, so they cover for each other to keep everyone’s workload balanced.
He gave a recent example. With three team members already out, he sent Anthony on spring break and stayed back himself to work with Michael. The team leader absorbing the gap, instead of asking someone to skip time off, is how that policy holds up in a busy week.
I really feel as the team leader, it’s my responsibility to know what’s out there.
Dano Sayles
Key takeaways for team leaders
- Do a role yourself, or have your successor do it, before you hire for it, so the new hire has a real trainer.
- Give a successor time to get ready. Dano’s handoff took about three years of preparation.
- Revisit titles and lanes as the team grows so each person ends up in the right seat.
- Install new systems one at a time, each with its own deadline.
- Automate anything your team does more than once, and keep up with what other team leaders are using.
- Plan coverage so your people can take time off, and be willing to fill the gap yourself.
