Introduction
I'm Joseph Dillamore, originally from the UK and now based in Greenville, South Carolina. My journey began with studying Economics and Management at Oxford University – what I'd call an undergraduate version of an MBA, blending theory and practice, with finance and economics all rolled into one.
At my core, I'm someone who loves building businesses and thinking about how they work. I'm testament to what can happen when you take advantage of opportunities that present themselves. One of the crucial lessons I've learned in entrepreneurship is that you not only have to capitalize on opportunities but also become an expert in the industry you're looking to build in – and I mean expert from multiple angles. It's about learning the ins and outs of how different pieces work together, mastering the terminology, and crucially, building relationships and gaining reputation.
My journey into real estate finance began when I joined Think Property Finance in the UK as employee number one. Starting as a fundraiser, I grew to become head of operations and eventually a partner, learning every aspect of the business from recruitment to underwriting, fundraising to deal structuring. After moving to the US, I completed my MBA at Clemson with a specialization in entrepreneurship, which gave me the foundation to launch multiple ventures in the real estate finance space. Today, I'm co-founding a new startup in mortgage loan servicing, building on my expertise in non-traditional real estate finance.
Finance Fellow
career options
The real estate finance industry offers diverse pathways that blend traditional finance with entrepreneurial opportunities. Here are the key career tracks:
Finance Fellow
skills
What are the main hard skills you use on a daily basis in your current job?
Combines quantitative financial analysis with pattern recognition in evaluating deals. This involves mastering both the numbers and developing an intuition for identifying potential issues in loan applications. I learned this through analyzing hundreds of deals at Think Property Finance, where we have maintained a near perfect record across 300+ loans.
Essential for projecting business outcomes, evaluating lending risks, and modelling cash flow for investors. This skill encompasses everything from basic Excel modelling to complex scenario analysis for both lending decisions and business planning.
Understanding how to create and negotiate complex financial arrangements that work for all parties. This involves balancing risk, return, and regulatory requirements while ensuring deals remain commercially viable.
What are the main soft skills you use on a daily basis in your current job?
Crucial in real estate finance, which is fundamentally a relationship-driven industry. I've found that all three businesses I've built or helped build came through relationship introductions. In our digital age, the ability to make personal connections and build trust face-to-face is invaluable.
Not just about having "lightbulb moments" but about rolling up your sleeves and finding practical solutions when no clean option exists. This might mean finding creative ways to handle regulatory compliance on a startup budget or developing alternative approaches to industry challenges.
Essential across all aspects of the business, from dealing with borrowers and brokers to building internal team relationships. It's not just about hard nose dealing but about establishing value and credibility over time.
Joseph
’s personal path
Tell us about your personal journey in
Finance Fellow
:
My path into real estate finance wasn't traditional – it started with an opportunity that I initially wasn't sure about. As I said, I began as employee number one, and through dedication and a willingness to learn every aspect of the business, I grew into the COO role within two years.
The real estate finance industry, particularly in the non-bank lending sector, offers unique opportunities for rapid growth. Without the traditional barriers found in other industries, there's real potential to grow with a business if you're willing to show initiative and think like a partner rather than just an employee.
Moving to the US, I pursued my MBA at Clemson, which opened doors to founding multiple ventures. Each step built on the previous one – from helping build Think Property Finance in the UK to launching a real estate finance marketplace, and now co-founding a mortgage loan servicing company.
What would you tell your younger you regarding building your current career?
Trust the doors that open in front of you. When I first entered real estate finance, I wasn't sure if it was the "right" opportunity. I couldn't have imagined eight years ago that I'd have helped build three companies and be living in South Carolina, starting a new business in loan servicing. Embrace the path rather than question it.
Don't be afraid to ask "stupid" questions. Often, when something doesn't make sense to you, it's not because you're missing something obvious – it's because there's a problem that needs solving. I learned this early in underwriting deals – when something felt off and I asked questions, it often revealed crucial issues that needed addressing.
Back yourself to try new things sooner. Especially in legacy industries like finance, there's a lot of status quo thinking. Don't wait to challenge it. You learn by doing in entrepreneurship, not by endless planning and theorizing.
Final thoughts & tips
The real estate finance industry offers unique opportunities for those willing to both learn and challenge conventions. Success comes from a combination of technical expertise and relationship building – you need both to truly thrive.
My journey demonstrates that opportunities often come in unexpected forms. The key is to recognize them, be willing to learn deeply, and have the courage to try new approaches. The industry rewards those who can balance innovation with practical execution.
Don't be afraid to start small and grow. Whether you're joining an existing firm or starting your own venture, focus on building genuine relationships and delivering real value. In this industry, reputation and relationships are currency that can open doors you might not even know exist.
Resources to dig in more
Paul Graham’s Essays on Entrepreneurship
Learn much of what is taught at entrepreneurship schools and accelerators for free, direct from the source.
BiggerPockets
Learn about real estate investing from the borrower’s side with the biggest online community for real estate investing.
Blog on Private Real Estate Lending
Learn all about the private lending industry with one of the most respected and well-thought blogs.
