He Cold Called a Stranger 18 Years Ago and Now They Run a Venture Fund Together | Matt Ober

One cold call can change the direction of an entire career. Eighteen years ago, Matt Ober picked up the phone and called Howard Lindzon, the founder of Stocktwits. That professional introduction eventually became a friendship, an investing relationship, and a long-term partnership. Today, Matt and Howard help lead Social Leverage, an early stage venture capital firm known for investing in fintech, financial technology, vertical software, artificial intelligence, and promising startup founders. Matt joins Bridget Ann Stuart to share how relationships, curiosity, persistence, and a willingness to hear no helped shape his career in financial markets, hedge funds, data strategy, venture capital, and seed stage investing. Their discussion explores confirmation bias and the way our brains naturally search for information that supports what we already believe. Matt explains why founders, entrepreneurs, investors, and business leaders need people around them who will challenge their thinking, question their assumptions, and help them make stronger decisions. For young professionals building careers in finance, investing, startups, technology, or artificial intelligence, Matt's advice is clear. Learn the tools, become faster and more capable, attend events, build genuine relationships, ask for opportunities, and do not allow rejection to stop you. Episode Highlights • The cold call that changed Matt Ober's career • Building Social Leverage with Howard Lindzon • How confirmation bias affects major decisions • Why strong ideas need honest challenges • What seed investors look for in founders • Lessons from investing early in Robinhood • Using AI to improve speed and productivity • Why relationships still create the biggest opportunities About Matt Ober Matt Ober is a Managing Partner at Social Leverage, an early stage venture capital firm investing in financial technology, financial services, vertical software, vertical SaaS, artificial intelligence, and data-driven companies. Before joining Social Leverage, Matt served as Chief Data Scientist at Third Point, where he worked across data science, analytics, technology, risk, equity investing, credit investing, venture capital, and cryptocurrency. Matt previously led data strategy at WorldQuant and was involved in the development of WorldQuant Ventures. He began his career at Bloomberg, where he gained experience with financial markets, investment technology, financial data, and the Bloomberg Terminal. At Social Leverage, Matt works alongside Howard Lindzon, Tom Peterson, and Gary Benitt. The firm has invested in companies including Robinhood, eToro, Kustomer, Manscaped, Stocktwits, and beehiiv. Matt also writes about investing, technology, data, artificial intelligence, financial markets, startups, venture capital, and entrepreneurship through his newsletter at his website. Connect with Matt:  LinkedIn: https://www.linkedin.com/in/obermattj X: https://x.com/obermattj Instagram: https://www.instagram.com/socialleveragellc ABOUT BRIDGET ANN STUART Bridget Ann Stuart is the host of The Inner Estate Podcast, a Realtor since 1998, and the CEO and Head Coach of Strategic Performance Coaching. Her work sits at the intersection of mindset, execution, leadership, business growth, and personal growth. Bridget brings real conversations to the table with entrepreneurs, real estate professionals, leaders, creators, coaches, authors, and high performers who are willing to talk about the inner work behind external results. Her mission is to help people think more deeply, act more intentionally, and build success that is aligned, sustainable, and real. CONNECT WITH BRIDGET Facebook: https://www.facebook.com/TheRealBridgetStuart/ Instagram: https://www.instagram.com/therealbridgetstuart/ YouTube: https://www.youtube.com/@TheRealBridgetStuart\ Interested in Being a Guest on The Inner Estate Schedule a pre-podcast call with Bridget Ann Stuart https://calendly.com/bridgetstuart67/theinnerestatepodcast