Lay of The Land
Jeffrey Stern
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#233: Chaya Slain (Virtera Partners) — Dare To Be Different, Dare To Be Great
Chaya Slain is the Founder, President, and Chief Investment Officer at Virtera Partners. After studying mathematics at Columbia University, she discovered her deeper interest in investing at Goldman Sachs. After several years in New York, she returned to Cleveland and joined Parkwood, the Mandel family investment office, where she spent more than a decade immersed in institutional investing. At Parkwood, she developed a disciplined, process-driven investment philosophy; built relationships with leading private equity, hedge fund, and real estate managers; and learned directly from Mort Mandel’s cultural and strategic principles. In 2020, Chaya founded Virtera Partners, a boutique investment firm designed to offer ultra-high-net-worth families the sophistication of a top-tier institutional allocator with the personal attention of a single-family office. Virtera has grown into a platform providing clients access to differentiated public and private market opportunities — supported by deep sourcing, rigorous diligence, and a willingness to do things differently when the data points that way. In our conversation, we trace Chaya’s journey from Wall Street to Cleveland; her early entrepreneurial spark running a deli during her time at Columbia University; the leap from investor to founder; and the empathy and insight that transition has given her when evaluating other entrepreneurs and investment managers. We explore behavioral discipline, portfolio construction in uncertain markets, long-term thinking, and what it means to build with integrity, excellence, and a true sense of stewardship. As someone who loves this intersection of investing and entrepreneurship, it was fun to hear Chaya’s reflections on it and learn from her experience. Please enjoy this great conversation with Chaya Slain 00:00 Chaya's Journey: From Goldman Sachs to Investing08:33 Lessons from Parkwood: Building a Network and Process12:06 The Entrepreneurial Spirit: Transitioning to Founding17:51 Investment Decision-Making: Process and Emotion21:34 Navigating Emotional Biases in Decision Making23:26 Investment Philosophy: Flexibility Over Boxes26:05 Contrarian Investments: The Case for Energy28:42 Cleveland vs. New York: The Advantage of Distance30:27 Lessons from Entrepreneurship: Empathy and Long-Term Thinking34:41 Evolving the Business: From Family Office to Fund37:24 Defining Success: Integrity and Performance38:29 Challenges of Being Different in Investing41:47 Current Market Concerns and Portfolio Construction43:46 The Importance of Alternative Investments ----- LINKS:https://www.linkedin.com/in/chaya-slain/https://www.virterapartners.com/ ----- SPONSOR: Roundstone Insurance Roundstone Insurance is proud to sponsor Lay of The Land. Founder and CEO, Michael Schroeder, has committed full-year support for the podcast, recognizing its alignment with the company’s passion for entrepreneurship, innovation, and community leadership. Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. To bring that vision to life, the company pioneered the group medical captive model — a self-funded health insurance solution that provides small and mid-sized businesses with greater control and significant savings. Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs. Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland. ----- Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here. Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/ Follow Lay of The Land on X @podlayoftheland https://www.jeffreys.page/
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