Biggest lessons for CEO’s from 17 Years of VC Experience | Matthew Leibowitz of Plaza Ventures

Matthew Leibowitz is the Co-Founder and Managing General Partner at Plaza Ventures, a growth-stage bespoke venture capital firm that focuses on structuring deals tailored to individual circumstances and strong relationships with companies. He has been a VC his entire professional career spanning 17 years and has seen the ecosystem evolve and completely change over the past 2 decades. Join Host Alex Shartsis in this episode as Matthew shares with us his observations of what core values set apart the best CEO’s and founders from the mediocre, what are best practices for aligning the board with management teams and other lessons from his long experience as a VC. Show Notes: 2:54 Unconventional Venture Capital Entry & Pattern Recognition 8:13 Bespoke Fund Structure & Strong Company Relationships 9:34 Providing Liquidity & Lifecyle Investment 16:38 Speed in Deal Execution & Recent 10-Day Transaction 17:53 CEO Best Practices: Overcommunication & Transparency 24:15 Integrity, Honesty, and Growth Mindset 26:17 Customer-Centric Approaches for Business Success 43:52 Prioritizing Customer Empathy for Business Success 47:06 Aligning Investor-Management Interests through Milestone Communication Guest: Matthew Leibowitz (linkedin.com/in/matthewleibowitz) Host: Alex Shartsis (linkedin.com/in/shartsis) Audio Engineer & Video Editor - James Fixx (fixxmusic.com) The Seed to Sequoia podcast is created by Silverwood Advisors to help founders with practical advice on building successful startups. If you would like to get expert advice for your startup reach out to us on: Website: silverwood.ai Linkedin: linkedin.com/company/silverwood-advisorsCompanies Plaza Ventures has invested in: Kitchen Hub Portless Vivecrop Super Symend Avidbots Hydrostor Kerv Placeholder Site 20/20 Clear Key Iguazio Landr Dejero Hubba CareGuide Drop PostBeyond SweetIQ Q4 Miovision MMBNetworks FindSpace