MB527: Inside the deal - With Robyn and Jackie Thompson
Robin Thompson, a real estate agent from Virginia with Jamaican and Panamanian roots, shares her journey from struggling to raise capital to successfully raising $3 million in a live multifamily syndication deal—despite initially being terrified of asking friends and family for money. What makes her story stand out isn’t just the numbers, but her revelation that the real bottleneck isn’t finding deals—it’s the fear of asking for capital. After 300 conversations and a pivot from deal-finding to capital-raising, she built a systematic, CRM-driven approach using her existing network, social media, and a 'soft commit' strategy that turned her first deal into a trust-building engine. She emphasizes that the most effective capital raising isn’t a hard pitch, but a patient, consultative process—starting with personal goals, easing into real estate as an option, and using scarcity and urgency to close. Her biggest insight? The first 15 conversations are the hardest—but by the 15th, the discomfort fades and confidence grows. Her story proves that raising capital isn’t about being a salesperson; it’s about becoming a trusted guide for people who never knew real estate investing was an option for them.
The first 15 capital-raising conversations are the hardest—but by the 15th, confidence grows dramatically and the process becomes natural.
Use a 'soft commit' strategy: your first live deal is your best proof of concept for future raises.
Ask for the allocation amount early—don’t wait for people to volunteer it.
Say 'It’s okay to tell me no' to filter out disinterested people and build trust.
Scarcity works: 'Only $100K left' increases commitment more than any pitch.
…and 3 more takeaways available in PodZeus
The Power of Capital Raising in Real Estate
Michael introduces Robin Thompson as a first-time dealmaker who raised $400K in her first deal and $3M in her second, highlighting the transformative power of capital raising in real estate syndication.
From Real Estate Agent to Capital Raiser
Robin shares her background as a real estate agent with a family legacy in development, explaining how her network and client relationships naturally positioned her to become a capital raiser.
The 300 Conversations That Led to a Deal
Robin reveals she had over 300 conversations before landing her ideal team, emphasizing that finding a deal is not just about underwriting—it’s about finding the right partners with complementary skills.
Why She Chose Capital Raising Over Deal Finding
Robin explains her pivot from deal finding to capital raising, citing her natural networking ability, comfort in conversations, and the realization that her strength lay in connecting investors to opportunities.
The First Conversation Was Terrifying
Robin describes the emotional weight of her first capital-raising conversation, comparing it to getting her real estate license—full of fear, self-doubt, and the fear of being seen as 'annoying'.
“If you're going to use it, is talking about the exclusivity of it, right? Why is the deal so great? What do you like about it?”
“The first one was very scary. It felt like when I first got my real estate license.”
“you're not going to go start talking about investing with you, right? What you're going to do is you're going to, you're going to say, Hey, what's going on, man.”
Host
Guest
Robin Thompson
person
Michael
person
DMM
organization
matchboxlegacyholdings.com
product
product
thefreedompodcast.com
product
Follow Up Boss
product
Jeremy Miner
person
product
HubSpot
product
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