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From Harvard Law to Selling Two Startups and Launching a VC Fund with Khadijah Robinson

AI for Business Owners

Release Date: 01/21/2026

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In this episode of AI for Business Owners, host Jeff Torello sits down with Khadijah Robinson, Co-founder and president of board at The PIT Atlanta and General Partner at Fictive Ventures, and former attorney. Khadijah discusses her remarkable journey from Harvard Law to founding and selling multiple startups, including a platform for black-owned e-commerce brands and a socially interactive marketplace. She also shares her experiences in angel investing and founding her own venture capital fund.

 

Throughout the conversation, Khadijah offers valuable insights into the dynamic world of startups and the role AI can play in improving business operations. They explore how AI tools like Sintra AI and Talknotes have streamlined personal productivity and team workflows. Khadijah also emphasizes the importance of avoiding over-optimization in early-stage startups and how AI can help manage growing business complexities.

 

This episode is packed with wisdom for business owners and entrepreneurs looking to understand how AI can enhance productivity and optimize operations, particularly in the fast-paced world of startups.

 

Key Takeaways:

  • From Lawyer to Entrepreneur: Khadijah’s journey from law school at Harvard to entrepreneurship, and why she ultimately pivoted from law to building startups.

  • AI in Startups: How AI tools can boost productivity and support the operational needs of early-stage companies.

  • Avoiding Over-Optimization: The risks of trying to over-optimize early in a startup and why flexibility is key in the first stages of business.

  • AI Tools for Personal Productivity: An in-depth look at tools like Sintra AI and Talknotes that are helping Khadijah and her team stay efficient.

  • The Role of AI in Scaling Operations: How startups can integrate AI to improve workflow management and increase efficiency.

 

Noteworthy Quotes:

  • "I very strongly believe in quitting. Just because you've invested time into something doesn't mean you should continue doing it if it's not bringing value to your life." – Khadijah Robinson

  • "Good enough is perfection. Don't over-engineer. Solve the problem as best you can, and move forward." – Jeff Torello

  • "AI can be the process guide for startups, helping them create repeatable processes and not get caught in the trap of over-optimizing too early." – Jeff Torello

  • "The first step is to get things done well enough, then iterate. Startups are about pivoting and adapting." – Khadijah Robinson

 

Key Timestamps:

[00:00] - Why most AI tools don’t deliver ROI unless they're deeply integrated

[01:23] - Khadijah’s journey: Harvard Law to tech entrepreneurship and VC

[04:13] - Walking away from law and the value of quitting with intention

[11:03] - Getting stuck in Nigeria during COVID, and how it helped her startup

[17:00] - Tools that work: Sintra AI and TalkNotes in startup operations

[24:27] - What kind of AI actually improves business outcomes

[30:34] - When not to automate: Startup pivots vs. AI rigidity

[37:50] - AI’s future: The tools are getting better, but still need guidance

[42:19] - AI, privacy, and healthy skepticism toward surveillance tech

[44:39] - Final thoughts: Use AI intentionally, not reactively

 

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