Guy Reams on Chess, B2B Tech Investing & Building Long-Term Wealth Through Strategy | Modern Investing Podcast

Message the HostIn this episode, we explore the intersection of technology, strategy, and entrepreneurship with Guy Reams, investor, tech executive, and member of New Fund Venture Group.Guy shares:His journey from computer science professor to tech executive and founder of a non-profit chess clubLessons from transitioning between academia, corporate roles, and startup investingHis approach to identifying early-stage opportunities in B2B SaaS, with a focus on team dynamics and tractionA behind-the-scenes look at how he manages personal investing, balancing risk while planning generational wealthWhy his love of chess strategy mirrors his disciplined investment mindset“Investing, like chess, is about thinking a few moves ahead—and staying calm no matter what happens on the board.”If you're curious about early-stage investing, startup evaluation, or how personal values inform portfolio construction, this episode is packed with wisdom from a leader who blends logic, heart, and foresight.About Guy Reams:Guy Reams is a technology executive, angel investor, and partner at New Fund Venture Group, where he supports early-stage tech companies with a focus on B2B SaaS and scalable solutions. With a background that spans computer science education, corporate tech, and entrepreneurship, Guy brings a unique blend of analytical rigor and real-world insight to his investing.Outside of his professional pursuits, Guy is the founder of a non-profit chess club, reflecting his lifelong love for strategy, teaching, and community-building. He’s deeply committed to helping startups grow with integrity, and to building a financial future for his family rooted in long-term thinking and values-driven leadership.Click Here to Check Out Our Upcoming Online Investing EventsAbout Sidepocket:If you don't have the time to professionally trade and are tired of being at the whim of the market's ups and downs, consider using Sidepocket to automate investing.Sidepocket monitors the markets 24/7 and automatically rebalances your holdings each month. To maximize returns while protecting against loss. That's why Sidepocket applies sophisticated quantitative methods, including tactical asset allocation to systematically minimize these drawdowns and consistently protect and grow your hard earned savings.To learn more, visit www.sidepocket.com