In this episode of the Rainmaker Podcast , host Gui Costin interviews Alisa Kolodizner, Co-Owner and Managing Partner at Prairie Hill Holdings, an alternative investment firm focused on triple-net lease commercial real estate. Alisa shares her compelling journey from immigrant roots to high-impact financial professional and entrepreneur. Alisa began her career in financial services at TD Ameritrade, eventually becoming one of the top five financial advisors company-wide within two quarters—despite no formal advisory background. Her early success, especially as a young woman in a male-dominated field, inspired her to mentor peers. She went on to establish TD Ameritrade’s first women’s networking group and moved into training roles, where she coached financial advisors across the country. Her division later became the top-performing in the company. After over a decade at TD Ameritrade, including institutional sales and product development, Alisa transitioned to entrepreneurship. She co-founded Prairie Hill Holdings in 2021 with business partner Matt, whom she met while exploring business acquisition opportunities. Prairie Hill is an open-end fund that invests in triple-net lease properties with high-quality, e-commerce-resistant tenants in sectors such as education, medical, industrial, and grocery. The fund is designed to offer institutional investors a stable, bond-like return profile with equity-level upside, addressing a common gap in traditional portfolios. Alisa emphasizes the importance of playing to your strengths rather than overinvesting in fixing weaknesses—a lesson she learned through the growing pains of entrepreneurship. She also highlights the significance of building a strong, complementary team to scale a business effectively. The discussion also touches on Alisa’s embrace of AI tools and large language models to increase operational efficiency. Prairie Hill uses AI-powered CRM and meeting software to support investor communications, follow-ups, and internal coordination. For young professionals entering financial services or sales, Alisa’s advice is clear: reach out to your network, stay curious, be authentic, and focus on being reliable. Reliability builds trust—and trust is the currency of leadership, teamwork, and successful sales. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.
