I sat down with Ann Dela Cruz to talk about something most real estate investors overlook when they’re trying to scale: community. In this conversation, Ann shares how she built a thriving investor network across the Asia Pacific while living overseas, why most investor events fail to create real momentum, and how intentional connection can unlock confidence, deal flow, and long-term growth. If you’ve ever felt isolated as your portfolio grows, struggled to find aligned investors in your time zone, or wondered whether building a community is worth the effort, this episode will completely shift how you think about support and scale.
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Hello everyone. I’m Adrienne Green, and today I have with me Ann Dela Cruz. Thank you for being here with me.
Thank you for having me.
Here, we focus on how real estate entrepreneurs break free of the grind using leverage, support, and smarter strategies. Let’s jump in. For listeners who are just meeting you, can you give us a quick overview of your real estate investing background and where you stand with that today?
Absolutely. I’m a serial entrepreneur specializing in real estate investing. I started my journey in 2004 by buying homes I wanted to live in, getting a roommate, which is now known as house hacking, and then converting those single-family homes into rentals. In 2008, when the market crashed and most people were running away, I saw it as an opportunity to start scaling my portfolio.
I got lucky early on because I didn’t fully understand market research at the time, but I happened to be investing in Colorado Springs, Colorado. That market grew significantly, which allowed me to become an accredited investor and opened the door to opportunities like commercial multifamily investing.
When my family was stationed overseas due to the military, we moved to Korea. I initially thought I had to pause everything and focus solely on family, but I found ways to continue investing. By leveraging technology and community, I was able to participate in commercial real estate through syndications as a limited partner and continue buying, selling, completing 1031 exchanges, and investing in larger deals despite being overseas.
That journey eventually led me back to Guam, where I’m now based. I’m focused on development, which is one of the highest-risk areas of real estate, but it aligns with the affordable housing crisis here. Everything I did after leaving Guam helped me build the skills, relationships, and confidence to return and contribute meaningfully. I’m now working to introduce 3D concrete printing technology to help build affordable homes on the island.
This is such a full-circle moment. You were born and raised in Guam, spent years investing in the continental U.S., Korea, and Japan, and now you’re back applying everything you’ve learned to development where you’re from.
It really is an incredible blessing and opportunity. I’m at a stage in life where I can give back in a meaningful and impactful way.
What I really wanted to focus on today is your experience creating an investor network, especially how you built it while living overseas. There are a lot of lessons here for anyone interested in building networks or hosting community events. Let’s start at the beginning. What originally motivated you to start an investor network in the Asia Pacific region, and what gap were you seeing?
It started with personal pain. I had just started my family and went from being very career-focused to moving overseas due to the military. I told myself I could be a stay-at-home parent, but I quickly realized it wasn’t fulfilling for me. I struggled with the idea because I knew many people would love that situation, but I needed more.
Once I gave myself permission to want more, everything shifted. When we moved to Japan, I was ready to reconnect with people and build relationships, but COVID made that impossible in traditional ways. I started connecting virtually through Facebook communities and realized some of those people were nearby. That led to hosting small in-person meetups, and the energy was incredible.
When I visited Guam, I noticed there were no investor meetups happening, so I hosted one. Seven people showed up, and the conversations were so engaging that we ended up staying for hours. It became clear people were craving connection and a space to share ideas.
Eventually, I partnered with someone who was hosting virtual meetups, and we expanded across Japan, Guam, and Korea. What started as strangers became a community built around shared challenges and shared goals. Living overseas can feel limiting, but through that shared experience, we found ways to overcome it together.
What problems were you able to help solve for investors who joined the network?
The biggest issue was access. There were no live events or resources available in our time zone. To attend events based in the U.S., we had to wake up at two or four in the morning. That wasn’t sustainable. By building a larger group locally and virtually, we were able to attract speakers and create meaningful learning opportunities that actually worked for our schedules.
For listeners unfamiliar with the Asia-Pacific region, what’s the time difference compared to the Eastern U.S.?
It’s significant. When it’s evening on Guam, it’s the middle of the night on the East Coast, and there’s also a day difference because of the international dateline.
I completely relate. When I was in Japan, I was having calls at two or three in the morning. It’s exhausting, and it makes what you built even more impressive.
A lot of investors think about starting a meetup or network but never follow through. What holds people back, and what advice would you give them?
It’s mostly mindset. People think they need to be the expert, but that’s not true. I love being the least knowledgeable person in the room. My role is simply to create space for people to connect. You don’t need an agenda or a speaker. You just need a date, time, and willingness to facilitate conversation.
When you bring diverse people together, the conversations that emerge are powerful. Even after years of building this community, I sometimes question whether I have time for it. But every time I show up, I see partnerships form, deals happen, and confidence grow. That confidence is one of the most powerful outcomes of community.
Information is everywhere now, but that doesn’t replace human connection. Seeing real people succeed helps investors move past fear and take action.
You’ve evolved from hosting events to building real community. How do you see the difference?
Most events are transactional. People focus on logistics and forget the purpose. The goal is to create space for engagement. When you’re intentional about how people interact, whether in small groups or casual conversations, the experience changes.
We design events to encourage connection and ongoing relationships. We want people to leave with support, not just inspiration. That’s what makes a community sustainable.
Tell us about the Asia Pacific Real Estate Investing Summit.
The summit is the evolution of our community. After years of virtual interaction, we wanted to meet in person. It’s a two-day event with keynotes focused on mindset and inspiration, along with master classes tailored to different investing paths. Attendees can choose sessions that fit their goals and meet others with similar interests.
What excites me is how intentional this event is. It’s designed to be customizable, held in Guam, and family-friendly. It aligns with spring break so people can combine learning with meaningful time with their families.
That’s intentional. Many investors say they invest for their families, yet most conferences don’t include them. Guam offers a unique cultural and family experience, and we’re even offering kids programs and excursions so families can truly enjoy the experience together.
I’m excited to attend, speak about remote landlording, and bring my family. Experiences like this matter.
For listeners who want to learn more, where should they go?
You can visit apresummit.com for details and registration. You can also connect with the Asia Pacific Investor Network on social platforms, and I’m always open to connecting on LinkedIn.
Thank you again for joining me. This has been an incredible conversation. If you’re listening from anywhere in the world, I encourage you to explore the summit and consider joining us in Guam on April 1st and 2nd.
Thanks again, Ann.