How this Real Estate Developer Raised $1M from ONE Email
What if I told you one of my friends raised $1,000,000 in just 24 hours—for his first solo real estate deal?
No private equity.
No institutional backing. No track record raising capital alone.
Just one email… backed by years of invisible work.
This is the story of Evan Holladay, a mission-driven developer who went from working at LDG Development to launching his own company, Holiday Ventures—and how his brand, his relationships, and his consistency led to a million-dollar raise overnight.
If you’re trying to raise capital for your first commercial real estate deal—especially if you don’t have a ton of cash or experience—Evan’s story will show you exactly what actually moves the needle.
Join our underwriting challenge to get all the tools, resources, and coaching on underwriting your deals: 30 Deals, 30 Days starting on October 22nd, 2025 - https://crecentral.com/30deals30days
Key Takeaways:
Building Trust and Relationships is Essential:
Evan Holiday was able to raise $1M in 24 hours not by chance, but by spending years building trust, credibility, and relationships with his audience.
Start Building Your Brand Early:
Successful fundraising starts long before the ask; by consistently sharing your journey, highlighting others, and demonstrating your values publicly.
Lead with Value, Not Just the Ask:
Evan created value for his network by focusing on others and providing insights, rather than only talking about his own business needs.
Communicate Your Mission Clearly:
People invest in individuals whose values and missions they understand and align with. Evan’s focus on impact and community attracted like-minded investors.
Raise Trust Before Raising Capital:
The most effective fundraising happens when you’ve established trust first, so your network is ready to support you when opportunities arise.
Consistency Matters:
Showing up consistently with integrity builds a reputation that encourages people to work with and invest in you.
Get commercial real estate coaching, courses, and community to jumpstart your investment journey over at CRE Central: www.crecentral.com
About Your Host:
Tyler Cauble, Founder & President of The Cauble Group, is a commercial real estate broker and investor based in East Nashville. He’s the best selling author of Open for Business: The Insider’s Guide to Leasing Commercial Real Estate and has focused his career on serving commercial real estate investors.
Episode Transcript:
Tyler Cauble 0:01
What if I told you that one of my friends raised a million dollars in just 24 hours for his first solo real estate deal, no institutional backing, no prior track record of raising capital independently just a single email. This
Tyler Cauble 0:22
is the story of my friend Evan holiday, a mission driven developer who went from working at a real estate firm to launching his own company, and how his years of brand building and relationship equity paid off in the moment that mattered the most. And if you're trying to raise capital for your first commercial real estate deal so that you don't have to put all of your own money into it, or maybe you don't even have the cash. This story has everything that you need to hear if you're new here. I'm Tyler Cobble, founder and CEO of cre central.com the premier education platform for commercial real estate. We help brokers, investors and developers learn how to break into the industry, source and fund their deals and scale with confidence. So whether you're transitioning from residential you're building a career alternative to college, or looking to grow your portfolio, you're in the right place. Now, Evan didn't grow up dreaming of raising capital or developing hundreds of millions of dollars of real estate. In fact, he originally thought he was going to be a doctor, but in college, he came across a large student housing project, a $55 million development with retail, hundreds of units and a massive footprint. And something just clicked for him. He realized this is what I want to be a part of. I want to build something that actually shapes our neighborhoods. That moment set Evan on a completely new path. So he did what anybody curious about real estate did, and he went, landed a job with a developer, LDG development, one of the top affordable housing developers in the country, where he quickly got real world experience. And I don't mean busy work, I mean negotiating deals, applying for public funding, meeting with city officials and managing full development life cycles. By the age of 23 he was already leading new market expansion for LDG. By the time he left, he'd helped develop over 1300 units across the southeast. But here's the key, even with all of that momentum, he didn't leave. Impulsively, he started laying the foundation for his own business. Long before he ever turned in his resignation, he formed an LLC holiday ventures. 18 months before he left, he and his now wife built a few Airbnb units to help create that extra income they would need during this transition. And most importantly, he launched a podcast called monumental where he interviewed impact focused entrepreneurs and real estate developers like yours truly. So fast forward a couple years, Evan's now ready to do his first independent deal under his new company, holiday ventures. He finds a great site, the numbers pencil, the vision is clear, and now it's time to raise the capital. But here's the thing, even though Evan had helped develop hundreds of millions of dollars in affordable housing at LDG, he had never raised capital on his own. So he had no corporate infrastructure, no institutional safety net, no big name co sponsor on the deal. This was different. This was his first time standing on his own. So what does he do? He writes an email, a single email, to the audience. He had spent years building through his podcast, through social media, through authentic, consistent relationship building. He had never raised a million dollars before, and in his words, he was freaking out, like, this is a total first for me. I was freaking out. I thought nobody was going to respond, but he still hit send. Within 24 hours, he had over a million dollars in commitments, no cold calls, no webinars and presentations, no chasing family offices with one giant check, just one well timed email backed by years of value creation and visibility and trust with his audience, the deal didn't get funded because of a flashy pitch deck. It got funded because Evan had already done the work long before the Ask ever came. And it's a powerful reminder for any investor, the money shows up when the trust is already there. You can't shortcut that, but you can start building it today. Now let's break down why Evan's raise worked, and more importantly, what made it repeatable so you can go and do the exact same thing. He shared his journey through the monumental podcast. Evan gave people a front row seat to his thinking, his mission and his learning process that built credibility, not just visibility. He elevated others. He interviewed guests, shined a spotlight on their stories, and built goodwill with every conversation, no pitching, no taking, just giving. He stayed consistent. No matter how busy things got. He kept showing up. And when you show up consistently with integrity, people start to believe that you're someone they want to work with. And most importantly, in my humble opinion, he built a brand around a mission, not money. People didn't just invest in Evan's deal. They invested in Evan's values, his focus on impact, affordable housing and community driven development. That's the secret. When people already believe in your why raising money for the what becomes 10 times easier? The email wasn't the raise. He said the raise was everything that he had done before pressing sent. So if you're watching this and you're trying to raise money for your first commercial real estate deal, the biggest mistake you can make is waiting until you need investors to start building that trust. So here are four clear lessons that you can take away from Evan's journey and apply in your business right now. Number one, start building your brand today. You don't need a huge audience, but you do need to be visible and have a credible presence. That could be a podcast. It could also be a newsletter or just a LinkedIn post once a week, just start sharing what you're learning, what you're working on, and what you care about. As a real estate investor, number two lead with value, not the ask. Evan didn't spend years talking about his deals. He spent years highlighting other people and providing insight that generosity built goodwill, and that goodwill became his capital source. Number three, let people know what you stand for. Impact driven, long term focused, not just flipping for the next exit. Evans investors knew his mission through and through, and they wanted to be a part of it. That clarity attracted the right capital. Value Aligned Capital. And number four, raise trust before you raise capital. This is the golden rule, because when the deal comes, when the opportunity is actually real, it's right in front of you. You don't want to be Cold Calling Strangers. You want your network already saying perfect. I've been waiting for the moment to invest with you. Most aspiring investors focus on only the deal, but the deal is really just the tip of the iceberg. The real work happens long before in the brand that you build, in the trust that you earn, in the relationships that you nurture. Want to copy Evan's playbook. Check out my full interview with him next you you.