The Worst Deal We’ve Ever Done

Nov 22, 2023


Share this podcast:

The Worst Deal We’ve Ever Done

About this podcast

🏠 Dive deep into the world of real estate investing with the Viking Real Estate Podcast! In this candid episode, our hosts, Nathan and Ravi, share invaluable insights and lessons learned from their most challenging venture to date.

🔍 Learn about Viking’s unique approach to deal deconstruction and how they turn past mistakes into future success. Ravi recounts a recent deal, discussing the issues faced, the lessons learned, and the crucial role of standard operating procedures in avoiding similar pitfalls.

💡 Gain firsthand knowledge on topics such as physical due diligence, debt structuring, and the importance of a well-planned exit strategy. Ravi’s transparency about a deal gone south provides a roadmap for high-net-worth investors entering similar ventures.

🤝 Discover the impact on investor relations when deals don’t go as planned and how open communication and transparency play a pivotal role in maintaining trust. Ravi shares the challenges faced, how they communicated setbacks, and the positive outcomes that resulted from honesty.

Connect with Nathan Loy:

Connect with Ravi Gupta: LinkedIn –

Email – [email protected]

Key takeaways

  1. Initial Assumptions and Planning Mistakes:
    • Explore the assumptions made at the outset of the deal that ultimately proved to be incorrect.
    • Offer insights into planning mistakes that could potentially lead to a bad deal.
  2. Financial Impact and Business Consequences:
    • Break down the tangible financial repercussions of the failed deal.
    • Discuss how the financial impact affected the overall business at that particular time.
  3. Legal Ramifications and Contractual Disputes:
    • Delve into any legal challenges that arose from the deal.
    • Discuss whether the deal led to contractual disputes or litigation.
  4. Hindsight and Due Diligence:
    • Reflect on the due diligence steps that, in hindsight, should have been taken before entering the deal.
    • Provide practical advice for listeners to avoid similar pitfalls in their own ventures.
  5. Impact on Stakeholder Relationships:
    • Examine how the deal affected relationships with investors, partners, and clients.
    • Highlight the ripple effects and the importance of managing stakeholder relationships.
  6. Leadership Challenges and Team Morale:
    • Discuss the impact of the deal on the team’s morale.
    • Share insights into how leadership challenges were navigated during the aftermath.
  7. Identifying Red Flags:
    • Take the audience back to the pivotal moment when it became clear the deal was going south.
    • Explore the red flags that were recognized during the course of the deal.
  8. Incorporating Lessons into Investment Strategy:
    • Share how the lessons from the bad deal have been integrated into the overall investment strategy.
    • Emphasize the importance of learning and growth even in the face of failure.
  9. Advice for High Net-Worth Listeners:
    • Offer specific advice for high net-worth listeners entering similar deals to avoid making the same mistakes.
    • Provide actionable insights that the audience can implement in their own investment endeavors.