Ep 257 How VCs Think: Insights from Keshia Theobald-van Gent

In this episode, we sit down with Keshia Theobald-van Gent, a seasoned venture capital investor with deep expertise in fund economics, portfolio strategy, and founder alignment. Keshia shares her sharp insights into how today’s most successful VCs operate and what emerging fund managers and founders need to know to succeed in this dynamic ecosystem.

Whether you're a founder seeking to better understand how VCs evaluate your startup, or an emerging fund manager preparing to launch your first fund, this episode is packed with actionable takeaways and deep industry wisdom.

🔍 Topics Covered:

• Keshia’s Career Journey:
  How her professional path has shaped her perspective on modern venture capital.
  
  
• What VCs Look For in Startups:
  The core criteria venture capitalists prioritize when evaluating investments—and how founders can align.
  
  
• Balancing Vision & Returns:
  How VCs manage the tension between financial ROI and founder vision.
  
  
• Key KPIs in Venture Investing:
  The metrics that matter and how startups should track and report them.
  
  
• Red Flags for VCs:
  Common early indicators of trouble in portfolio companies—and how to avoid them.
  
  
• Liquidity & Exits:
  How VCs think about liquidity events, secondary sales, and capital returns.
  
  
• Crafting an Investment Thesis:
  What goes into building a compelling thesis that attracts LP capital.
  
  
• Venture Capital & Family Offices:
  Trends shaping these increasingly collaborative relationships.
  
  
• Fund Economics Explained:
  Core differences between venture capital and private equity economics.
  
  
• Overlooked Fund Expenses:
  Hidden costs that new fund managers often miss.
  
  
• Reporting to LPs:
  How firms communicate performance, and what LPs actually care about.
  
  
• When Investments Go to Zero:
  Fund strategy, tax implications, and wind-down considerations.
  
  
• Lessons for Emerging Managers:
  Common pitfalls and best practices for first-time fund leaders.
  
  
• Founder Success Story:
  A candid look at one portfolio company’s journey and growth challenges.
  
  

💡 Bonus Insights (if time allows):

• How branding influences deal flow and VC visibility.
  
  
• One thing Keshia would change about the VC industry.
  
  
• How AI and automation are changing the game for VCs and founders alike.
  
  

📬 Connect with Keshia:

To follow Keshia’s work or reach out for collaboration, connect with her on LinkedIn.

📌 Disclaimer:

The views expressed in this episode are for educational and informational purposes only and do not constitute financial or investment advice. The views expressed are personal and do not necessarily reflect the views of any affiliated organizations. Such as the views of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC.”