Episode 106

How Real Connections Make Real Deals with Derek Dombeck

Published on: 3rd September, 2025

Amy sits down with Wisconsin-based real estate investor Derek Dombeck. Derek has been investing in the market since 2003, and his experience ranges from structuring deals to wholesaling, flipping, landlording, and lending. Derek is also the co-author of two books, “Next Level Your Life” and “The Transformational Journey.” He is also the host of the podcast The Generations of Wealth. Derek has been married for more than two decades and is a self-professed adrenaline junkie.

In this episode, you’ll hear:

  1. Maintaining a heart-centered approach to your business and staying open to unique opportunities and conversations.
  2. Derek Dombeck’s origin story in real estate and investing beginning with his time as a construction worker in his 20s.
  3. Alternative methods of funding investments and building an investor network.
  4. Marketing by example and not pre-judging what someone may or may not have.
  5. Protecting your investors with a servant mindset.
  6. Utilizing masterminds and events to network and offer education to investors.
  7. Designing the life you want centered around your personal vision for your life.
  8. The biggest mistake people make during negotiations.
  9. Derek’s advice for finding your own success.

Connect with Amy Calandrino here:

Beyond Commercial - https://beyondcommercial.com/amy-calandrino-ccim/

Amy Calandrino - https://linktr.ee/amycalandrino

Connect with Derek Dombeck:

Website - https://derekdombeck.com/

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About the Podcast

The Performance Mindset Show - Helping you level up in entrepreneurship, commercial real estate, leadership and life
The Performance Mindset Show - Helping you level up in entrepreneurship, commercial real estate, leadership and life
Success isn’t just about the deals you close or the investments you make - it’s about how you think, grow, and lead.

Hosted by Amy Calandrino, founder of Beyond Commercial, The Performance Mindset Show explores the habits, strategies, and mindset shifts that drive peak performance in business, real estate, health, and life.

Based in sunny Orlando, Amy and her guests dive into leadership strategies, decision-making frameworks, mental resilience, and personal growth. From cutting-edge commercial real estate insights to biohacking, neuroscience, entrepreneurship, and spiritual well-being—this podcast is for the endlessly curious who want to level up in all aspects of life.

Each episode features inspiring conversations with top-performing business leaders, investors, mindset experts, and high achievers across various industries. Whether you’re looking to sharpen your leadership skills, optimize your brain and body, or simply gain insights from some of the most driven individuals out there, you’re in the right place.

Ready to expand your mindset and unlock your full potential?

📍 Connect with Amy Calandrino:
🔗 BeyondCommercial.com
🔗 AmyCalandrino.com

Let’s build, grow, and thrive—together. 🚀

About your host

Profile picture for Amy Calandrino

Amy Calandrino

I thrive on meeting clients face-to-face, shaking hands, and helping them achieve their short and long-term goals. For me, it's all about the personal touch combined with a strategic lens. I get great satisfaction from finding the best space and maximizing returns for my clients. But BEYOND the transaction, what truly drives me is developing personalized strategies to help them build wealth.

My clients and colleagues describe me as having both head and heart. I’ve earned CCIM and SIOR designations, and Beyond Commercial is a certified Woman-Owned Business Enterprise (WBE) and Woman-Owned Small Business (WOSB). I’m recognized as a key influencer in the industry.

Developing ongoing relationships and seeing my clients thrive is what truly drives me. Business owners and investors benefit from my extensive knowledge of inventories, trends, and space. While I have a hyper-local focus in Winter Park and Greater Orlando, I have global reach through alliances with other boutique brokerages and the Commercial Real Estate Supplier Diversity Alliance (CRESDA).

While Central Florida is home, I developed an affinity for Winter Park while earning my degree at Rollins College. Its charm reminds me of my New England roots. Today, I feel blessed to serve many of the area’s businesses and property owners. I also contribute to the community as a Park Avenue District Board member, part of the Main Street America program.

Beyond my work at Beyond Commercial, I'm involved in initiatives that align with my professional and personal aspirations. Alongside my husband Phil, I co-founded the Calandrino Foundation to inspire entrepreneurship, starting with our youth. I’m also passionate about sharing insights through my Performance Mindset podcast, where I engage in thought-provoking conversations with fellow business leaders.

My upcoming book, From Perfect to Real: Embracing Authenticity for Peak Performance, will chronicle my personal struggles, professional journey, and the SPORT Success System® I developed for achieving peak performance.

While providing above-and-beyond service is a priority, my greatest loves are my faith and family. Phil and I cherish raising our two lively children. In my downtime, I also enjoy a round of golf or running a 5k.

The team at Beyond Commerical and I are ready to serve you above and BEYOND. Connect with us today!