Masters of Moments involves conversations with top entrepreneurs and business leaders about hospitality, Real Estate investing, and company building. We explore the ideas, strategies, and approaches that brought them to where they are today. This podcast is for you if you are a seasoned investor, an upstart entrepreneur, or someone looking to break into the real estate and hospitality investing world. Jake Wurzak is the CEO of DoveHill Capital Management and Wurzak Hotel Group, a leading vertically integrated hospitality investment platform. Since 2011, he’s led the investment of $1.5 billion in hotel assets throughout the country. Follow Jake on Twitter: https://twitter.com/JWurzak Take the Hospitality Real Estate Investing Masterclass: https://learn.jakewurzak.com/ Subscribe to the show on YouTube: https://www.youtube.com/channel/UCzvzdJASDiEXhV9VhkaEoWA Learn How to Invest with DoveHill: https://dovehillcos.junipersquare.com/portal/view_lead_capture_form/MzhmOGE4MTUwMjZhNDZkNmU1MGE0NmYwOTdhZjk2MzAxYzE0MjIzMGdBV1ZEUUFBQUFBQUFBQW9UVzhJVFdzTlRrNkpkSlF1 DoveHill: www.dovehillcos.com
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Masters of Moments involves conversations with top entrepreneurs and business leaders about hospitality, Real Estate investing, and company building. We explore the ideas, strategies, and approaches that brought them to where they are today. This podcast is for you if you are a seasoned investor, an upstart entrepreneur, or someone looking to break into the real estate and hospitality investing world. Jake Wurzak is the CEO of DoveHill Capital Management and Wurzak Hotel Group, a leading vertically integrated hospitality investment platform. Since 2011, he’s led the investment of $1.5 billion in hotel assets throughout the country. Follow Jake on Twitter: https://twitter.com/JWurzak Take the Hospitality Real Estate Investing Masterclass: https://learn.jakewurzak.com/ Subscribe to the show on YouTube: https://www.youtube.com/channel/UCzvzdJASDiEXhV9VhkaEoWA Learn How to Invest with DoveHill: https://dovehillcos.junipersquare.com/portal/view_lead_capture_form/MzhmOGE4MTUwMjZhNDZkNmU1MGE0NmYwOTdhZjk2MzAxYzE0MjIzMGdBV1ZEUUFBQUFBQUFBQW9UVzhJVFdzTlRrNkpkSlF1 DoveHill: www.dovehillcos.com
In this special “Coaching Call” Jake Wurzak goes solo to share everything he’s learned from over a decade of raising capital in real estate. Drawing on personal experience—from his first $7 million deal with no clear path to funding, to building DoveHill into a hospitality investment platform—Jake walks through the real, unfiltered playbook for getting deals financed.
This episode is packed with insights on how to approach high-net-worth individuals, build trust with investors, and create compelling deal collateral that actually converts. Jake also breaks down how he structures investor communications, designs pitch decks and memos, leverages tools like Juniper Square, and uses short personalized videos to bring deals to life. It’s the same method he’s using today to raise preferred equity for a current hotel redevelopment project in Savannah, Georgia.
Key lessons include:
- Why raising money for a single deal is easier than launching a fund
- The importance of being honest, conservative, and clear with investors
- How to use storytelling, design, and delivery to drive commitments
- Tips for building investor databases, managing follow-ups, and closing deals
- Real talk on sharing upside, walking away from bad capital, and learning through failure
Whether you’re about to raise your first $1 million or scaling to institutional capital, this behind-the-scenes coaching call gives you a candid, detailed roadmap for how to actually get it done.
Connect & Invest with Jake:
Follow Jake on X: https://x.com/JWurzak
1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching
Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo
Topics:
(00:00:00) - Intro
(00:00:38) - More on DoveHill
(00:05:05) - Jake’s First Deal and Lessons Learned
(00:08:57) - Raising Capital: Strategies and Tips
(00:14:44) - Creating Effective Investment Memos
(00:16:59) - Designing Investment Decks
(00:35:26) - Engaging Investors with Video Pitches
(00:40:21) - Investor Intake Process
(00:44:01) - Negotiation Tips
(00:45:09) - Q&A: Meeting Potential Investors
(00:48:59) - Q&A: Handling Design and Pre-Development Costs
(00:53:06) - Q&A: Capital Structure and Investor Profiles
(00:56:22) - Q&A: Overcoming Appraisal Challenges
(00:59:28) - Q&A: Partnering in New Markets
(01:02:06) - Q&A: Preferred Equity and Fund Structures
(01:17:58) - Q&A: Subscription Process and Investor Relations
(01:22:27) - Unexpected Investor Stories
Masters of Moments
Masters of Moments involves conversations with top entrepreneurs and business leaders about hospitality, Real Estate investing, and company building. We explore the ideas, strategies, and approaches that brought them to where they are today. This podcast is for you if you are a seasoned investor, an upstart entrepreneur, or someone looking to break into the real estate and hospitality investing world. Jake Wurzak is the CEO of DoveHill Capital Management and Wurzak Hotel Group, a leading vertically integrated hospitality investment platform. Since 2011, he’s led the investment of $1.5 billion in hotel assets throughout the country. Follow Jake on Twitter: https://twitter.com/JWurzak Take the Hospitality Real Estate Investing Masterclass: https://learn.jakewurzak.com/ Subscribe to the show on YouTube: https://www.youtube.com/channel/UCzvzdJASDiEXhV9VhkaEoWA Learn How to Invest with DoveHill: https://dovehillcos.junipersquare.com/portal/view_lead_capture_form/MzhmOGE4MTUwMjZhNDZkNmU1MGE0NmYwOTdhZjk2MzAxYzE0MjIzMGdBV1ZEUUFBQUFBQUFBQW9UVzhJVFdzTlRrNkpkSlF1 DoveHill: www.dovehillcos.com
