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A Little About Me

FROM THE
CLASSROOM
TO THE BOARDROOM.

Family · Faith · Entrepreneurship · Serial Entrepreneur ·

Building Businesses.
Living with Purpose.

From a $37K teaching salary to founding The Rise Collective. A vertically integrated group of companies built around real estate, hospitality and wealth creation.
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My Businesses

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As the parent company for a diverse portfolio of brands, The Rise Collective is united by a shared mission: to deliver unmatched quality, service and expertise across the vacation rental, real estate and investing industries.

 

Built entirely without outside funding, Rise operates at the intersection of real estate, design, hospitality and wealth strategy with a rapidly expanding national footprint.

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BECAUSE I COULDN'T
SIT STILL...

All Pro Garage Doors brings the same standard of professionalism and excellence to the home services industry that Elliott has applied across his entire portfolio of businesses.


From residential repairs to full commercial installations, All Pro delivers dependable, high-quality garage door services with a team you can trust.

How a 60,000 person festival came to be...
00:20

How a 60,000 person festival came to be...

🎙️Subscribe to @elliottcaldwellpodcast
Why Your Business Is Worth Less Than You Think: Vince Perri
44:39

Why Your Business Is Worth Less Than You Think: Vince Perri

🔑Ready to learn how to invest in Airbnb, hassle-free? Fill out this form and our BNB Turnkey Team will reach out to you: https://e0jcghoxv59.typeform.com/to/t4BDOZGN Welcome to The Elliott Caldwell Podcast On Successful DNA — the show where driven individuals break down the habits, experiences, and mindset behind building something real. Whether you’re an entrepreneur, investor, or someone chasing your next level, this podcast uncovers what it actually takes to turn momentum into long-term success. Vince Perri is a serial entrepreneur, business broker, and exit planning advisor who has spent more than 17 years building, scaling, and selling businesses across multiple industries. From tennis academies and public adjusting firms to online education and business brokerage, Vince has experienced the challenges of entrepreneurship from nearly every angle. In this episode, Vince breaks down why most business owners overestimate what their companies are worth, how messy financials can destroy a potential sale, and what buyers actually look for before making an acquisition. He explains why recurring revenue, clean books, customer diversity, strong systems, intellectual property, and reduced owner dependency can dramatically increase the value of a business. Vince and Elliott also explore the growing demand for landscaping, HVAC, plumbing, property management, assisted living, and other recession-resistant businesses. They discuss why buying a “boring business” is not as easy as social media makes it seem, how private equity can help or hurt a company, and why entrepreneurs must perform serious due diligence before choosing a partner or acquisition. The conversation also gets personal. Vince shares why he left corporate America during the 2008 recession, how losing friends at a young age shaped his approach to fatherhood, and why family remains his highest priority. He explains how he structures his schedule around his son, why entrepreneurship gave him the freedom he was searching for, and how he plans to teach his child to create income instead of simply asking for it. At the heart of Vince’s philosophy is persistence. Problems do not disappear as your business grows. They simply change. The entrepreneurs who succeed are the ones who continue moving forward, building systems, solving problems, and preparing their companies for opportunities before those opportunities arrive. This is a practical masterclass on buying businesses, preparing for an exit, increasing enterprise value, creating recurring revenue, balancing entrepreneurship with family, and building a company that can survive without you. 📲 Follow Elliott ‼️IG: @elliottcaldwell https://www.instagram.com/elliottcaldwell/ 🏡 Follow The Rise Collective: @the_rise_collective_ https://www.instagram.com/the_rise_collective_/ 🌐 More about The Rise Collective: https://rise-collective.com/ 🔑 Explore BnB Turnkey: https://bnb-turnkey.com/ 📩 Subscribe to the STR Report newsletter: https://thestrreport.com/ 📲 Find Our Guest https://www.youtube.com/@AllBusinessVince https://www.tiktok.com/@thevinceperriofficial https://www.instagram.com/vinceperriofficial/ https://www.facebook.com/VincePerri/
How Two Brothers Built a $250K-a-Month Card Game: Cody & Brandon
01:03:59

How Two Brothers Built a $250K-a-Month Card Game: Cody & Brandon

🔑Ready to learn how to invest in Airbnb, hassle-free? Fill out this form and our BNB Turnkey Team will reach out to you: https://e0jcghoxv59.typeform.com/to/t4BDOZGN Welcome to The Elliott Caldwell Podcast On Successful DNA — the show where driven individuals break down the habits, experiences, and mindset behind building something real. Whether you’re an entrepreneur, investor, or someone chasing your next level, this podcast uncovers what it actually takes to turn momentum into long-term success. Cody and Brandon are two of the founders behind How Deep Will You Go, a connection card game built to help people move beyond surface-level conversations and discover the deeper parts of one another. What began as a series of college street interviews grew into a viral content brand, a community of millions, and a physical product that has reached more than 100,000 customers. In this episode, Cody and Brandon reveal how they turned audience demand into a business generating roughly $250,000 per month and shipping around 7,000 games a month. They break down how a video with millions of views validated the product, why they collected emails before launching, and how preorders allowed them to purchase their first inventory without outside funding. Their first official launch generated approximately $10,000 within minutes and sold out within hours, proving that the market was ready. Their journey was far from perfect. The brothers share how a broken purchase link nearly derailed their first launch, how incorrect shipping information forced them to cancel roughly $10,000 in TikTok Shop orders, and why learning to slow down became one of their most important business lessons. They also explain the decision to stop fulfilling orders from their living room, hire a third-party logistics company, invest more aggressively in advertising, and build the infrastructure required to scale. Behind the numbers is a powerful personal story. Cody and Brandon open up about entering foster care as children, being adopted before the triplets were separated, reconnecting with their biological mother as adults, and choosing entrepreneurship over a free college education. They discuss how hardship, self-belief, brotherhood, and a refusal to accept limiting circumstances shaped their ambition. This is a raw conversation about product-market fit, viral content, ecommerce, cash flow, inventory, resilience, and what happens when you create space for something bigger. 📲 Follow Elliott: ‼️IG: @elliottcaldwell https://www.instagram.com/elliottcaldwell/ 🏡 Follow The Rise Collective: @the_rise_collective_ https://www.instagram.com/the_rise_collective_/ 🌐 More about The Rise Collective: https://rise-collective.com/ 🔑 Explore BnB Turnkey: https://bnb-turnkey.com/ 📩 Subscribe to the STR Report newsletter: https://thestrreport.com/ 📲 Find Our Guests: https://www.instagram.com/indicody/ https://www.instagram.com/xbrandonrode/ https://www.instagram.com/howdeepwillyougo/
Why Leaving Your Comfort Zone Changes Everything: Giacomo Sanvitale
37:12

Why Leaving Your Comfort Zone Changes Everything: Giacomo Sanvitale

🔑Ready to learn how to invest in Airbnb, hassle-free? Fill out this form and our BNB Turnkey Team will reach out to you: https://e0jcghoxv59.typeform.com/to/t4BDOZGN Welcome to The Elliott Caldwell Podcast On Successful DNA — the show where driven individuals break down the habits, experiences, and mindset behind building something real. Whether you’re an entrepreneur, investor, or someone chasing your next level, this podcast uncovers what it actually takes to turn momentum into long-term success. Giacomo Sanvitale left Italy at 20 years old with a dream, a soccer career, and no guarantee that any of it would work out. Raised by a single mother outside of Milan, he grew up watching her work multiple jobs and eventually take the risk of starting her own business. That same willingness to step outside the expected path would eventually lead Giacomo from Italy to Switzerland, Missouri, Oregon, Florida, and ultimately Tampa as he chased soccer, content creation, and a bigger vision for his life. In this episode, Giacomo opens up about what it really means to leave your comfort zone, start over in a new country, navigate loneliness, battle anxiety, recover from career-threatening injuries, and keep moving forward when doors repeatedly close. He shares why he believes American culture gives people permission to take risks, how growing up in Italy shaped his perspective on relationships and community, and why European soccer culture develops talent so differently from the United States. Giacomo also breaks down why he started creating content before it was considered cool, how filming his soccer journey led to a viral YouTube video, and why he has always been drawn to doing the things other people are too uncomfortable to try. From filming alone in Missouri so his mother could see his life to building an audience while being unable to legally make money because of visa restrictions, his journey is a lesson in patience, sacrifice, creativity, and staying committed when nobody sees the full story. At the heart of Giacomo’s journey is an intense refusal to settle for an average life. He talks honestly about growing up without knowing his father, feeling responsible for changing his family’s future, struggling financially while appearing successful online, and learning that humility, honesty, and perseverance are the qualities that truly define successful people. This is a raw conversation about immigration, ambition, identity, loneliness, resilience, content creation, relationships, and what happens when you decide that leaving your comfort zone is the only way to build the life you truly want. 📲 Follow Elliott ‼️IG: @elliottcaldwell https://www.instagram.com/elliottcaldwell/ 🏡 Follow The Rise Collective: @the_rise_collective_ https://www.instagram.com/the_rise_collective_/ 🌐 More about The Rise Collective: https://rise-collective.com/ 🔑 Explore BnB Turnkey: https://bnb-turnkey.com/ 📩 Subscribe to the STR Report newsletter: https://thestrreport.com/ 📲 Find Our Guest: https://www.instagram.com/giacomosanvitale/?hl=en

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