Episodes 2, 6, and 13 Vibe: The eccentric cowboy billionaire. Known for his colorful shirts and early investments in Twitter, Uber, and Instagram, Sacca brought a pure tech-and-data approach. He was aggressive, fast-talking, and often clashed with Kevin O’Leary. He famously made multiple offers on the spot. If you had a SaaS or app idea, you wanted Chris.