In this episode of What It Takes, I sit down with Ray Winkleman, a guy who’s not just crushing it in tech and real estate but really living the entrepreneurial journey. From a small-town kid in Nova Scotia to building a SaaS empire and managing over 300 apartment units, Ray’s story is a masterclass in resilience, leadership, and just plain getting it done.We dive into his early days, how he broke away from the 9-to-5 grind, and what fueled his drive to succeed—hint: it’s not about fancy cars or flashy watches. Ray’s all about building freedom, making smart moves, and staying tough when the going gets rough. He talks about why personal development matters, why every job is secretly a sales job, and how the journey shapes the person you become.
If you’ve ever wondered what it really takes to succeed—beyond the warm and fuzzy motivational quotes—this is the episode for you. Ray keeps it real, sharing the highs, the lows, and the lessons he’s learned along the way. Let’s get into it!
Connect with Ray on LinkedIn - https://www.linkedin.com/in/raywinkelman/Visit Ray's software consultancy - https://shadowsoftware.comExplore Ray's firearm trading platform - https://americanguntrader.com
Chapters
00:00 Introduction to Ray Winkleman00:57 Entrepreneurial Ventures and Software Development04:03 Real Estate Investments and Strategies07:53 Early Life and Journey into Entrepreneurship12:00 Motivations Behind Entrepreneurship16:00 Transitioning from Employment to Entrepreneurship18:53 Building Successful Projects and Contracts22:08 Personal Development and Overcoming Challenges27:03 The Reality of Entrepreneurship29:53 Passion for Technology and Career Path32:46 The Nature of Love and Reality34:54 Rebellion Against Subjectivity36:59 The Journey into Technology and Passion37:37 The Role of Passion in Entrepreneurship39:52 Political Landscape and Personal Freedom42:11 Future of Work and Universal Basic Income


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