The Path to Exit | Episode 35: Pitfalls to Avoid on the Path to an Exit (with Goldman Sachs)

Podcast: The Path to Exit
Host: Mike Lyon, Vista Point Advisors
Guest: Sarah Letourneau, Private Wealth Advisor, Goldman Sachs
Air Date: December 16, 2025

Episode Overview

This episode explores the most common pitfalls that technology founders encounter on their way to a company sale or major liquidity event. Host Mike Lyon and guest Sarah Letourneau draw from extensive firsthand experience to share the best practices (and worst mistakes) when it comes to timing exits, assembling deal teams, planning for life post-transaction, and communicating with family. The discussion centers on practical, founder-focused advice that demystifies the M&A process and helps listeners optimize their deals—not just for valuation, but for long-term personal legacy.

Key Discussion Points & Insights

1. Timing the Exit: The Myth of Perfect Conditions

• Perfection is unrealistic ([01:19]-[02:07]):
  • Founders often wait for flawless metrics, new product launches, or ideal markets.
  • In reality, “everything almost never lines up at once.”
  • Sarah: “If things are mostly good and you’re personally ready, it might be wise to start the process rather than waiting for perfection. Don’t let the perfect be the enemy of good.” [01:31]
• Risks of Waiting Too Long ([02:07]-[02:44]):
  • Waiting can mean missing optimal market windows, especially in rapidly shifting sectors like AI.
  • Mike: “Markets don’t really wait for calendars. They do their own thing.” [02:49]

2. The Danger of Anchoring on a Target Price

• Psychology of the Headline Number ([03:06]-[03:35]):
  • Founders often fixate on a headline figure (e.g., “I need $100M”) or a specific multiple.
  • Sarah: “Anchoring…can become a little bit more about ego rather than economics. You risk overlooking potentially great partners or strong offers.” [03:15]
• Practicality Over Ego:
  • Focus on deal fit, structure, and certainty of close, rather than arbitrary numbers.

3. Understanding Wealth and Post-Sale Life

• The Fluidity of Proceeds ([03:59]-[05:07]):
  • Money from a sale is not static; it becomes an investable portfolio supporting your lifestyle.
  • Founders must shift from business distributions to steady, planned withdrawals.
  • Sarah: “We often sit down and translate deal terms into a practical spending plan...seeing that math often gives founders confidence.” [04:13]
• Example of Rollover & Post-Close Commitment ([05:13]):
  • Goldman Sachs modeling shows that keeping a stake plus new salary can de-risk the founder’s outcomes.
  • “Even in a conservative scenario…the family was still okay.” [05:54]

4. Assembling the “Dream Team” for the Deal

• Who Should Be at the Table? ([06:07]-[07:42]):
  • Transaction Side: Specialist investment bank and top-tier M&A attorney.
  • Personal Side: Private wealth advisor, estate attorney, CPA experienced in complex exit.
  • Sarah: “On the personal side, think about your advisory team as the three legs of the stool…where we see founders go wrong is working with advisors who aren’t specialized enough for a complex exit.” [06:45]
• Pitfalls:
  • Relying solely on long-time CPAs or going it alone can cost owners millions.
• Mike: “If you use a lawyer who’s not super experienced in M&A or SaaS, they’re kind of defensive…and what they tend to do is silo information which can lead to some bad outcomes.” [08:06]

5. Real-World Deal Outcomes: With and Without a Strong Team

• Without a Banker ([08:48]):
  • Example: Founder closed at $15M below LOI after a difficult, drawn-out process.
• With a Strong Team:
  • Coordinated advisors resolved tricky tax issues efficiently and closed in 30 days.
  • Sarah: “The founder closed in 30 days. Excellent outcome.” [09:35]
• Strategic Retrades & Preparation ([09:45]-[11:05]):
  • Sophisticated buyers often seek to renegotiate (retrade) in exclusivity—preparation and competitive tension are crucial.
  • “[If] you only have two or three experiences, you’re over-indexing to the two or three things that happened in that deal…With hundreds of experiences, you’re more well balanced.” – Mike [10:24]

6. The Final Stretch: Emotional and Tactical Pitfalls

• Emotional Overload in Closing ([11:05]-[11:52]):
  • Diligence is intense; it’s a bad time to make additional life decisions like home purchases or big commitments.
  • Sarah: “Let the dust settle for about six months post-close. Your life is about to change and you owe yourself the space to experience that before making big commitments.” [11:33]
• Pre-Transaction Planning is Critical ([12:14]):
  • Mission-critical to get tax and estate planning structures in place well before the deal signs (ideally 12 to 18 months in advance).
  • Sarah: “The right structures can ultimately mean potentially multi millions in tax savings for your family…but you absolutely cannot bolt this on the day before the LOI.” [12:24]

7. Family Communication and Changing Realities

• Proactive Narrative Control ([13:12]-[15:00]):
  • Children and close contacts may hear about a deal online—control the narrative in the family.
  • Sarah: “If your children are old enough to search online, they may learn about the deal from someone other than you…You can acknowledge the change that’s going on, invite questions, and set expectations.” [13:42]
• Managing External Requests and Giving:
  • Have frameworks and processes for communicating with friends, extended family, and charities who may ask about the newfound wealth.

Notable Quotes & Memorable Moments

• On Mental Anchors and Outcomes:

  “Anchoring…can become a little bit more about ego rather than economics.” – Sarah [03:15]

• On Readiness and Timing:

  “If things are mostly good and you’re personally ready, it might be wise to start the process rather than waiting for perfection.” – Sarah [01:31]

• On Planning and the Team:

  “You don’t have to do this alone. Build that right team, align them early, and let them link arms with you through this extraordinary moment.” – Sarah [15:56]

• On Stress During the Final Stretch:

  “It’s not the time to think about upgrading your primary home or…closing on a second home. All of this just adds complexity and distraction…Let the dust settle.” – Sarah [11:33]

• On Family Communication:

  “Typically people prefer to control that narrative and control it at home so you don’t have to share dollar figures, but you can acknowledge the change that’s going on, invite questions, and set expectations.” – Sarah [13:46]

Timestamps for Key Segments

• [01:19] – Common mistakes founders make: perfect timing myth
• [03:06] – The dangers of anchoring on target price
• [04:30] – Transition from business distributions to investment income
• [05:13] – Example of rollover and post-close commitment
• [06:24] – Building your “dream team” of advisors
• [08:48] – Real-world examples: outcomes with and without a bank
• [11:05] – Emotional pitfalls in the closing stretch
• [12:14] – Timing of pre-transaction planning (tax & estate)
• [13:31] – Family communication and new realities

Episode Summary & Final Takeaways

• Don’t wait for all the stars to align—be guided by readiness, health of the business, and broad market factors, not mythical perfection.
• Avoid fixating on a headline exit number; prioritize long-term financial and life goals, considering how proceeds can support your new lifestyle.
• Invest in assembling an experienced, specialized advisory team on both the transaction and personal planning sides.
• Give yourself ample lead time for complex tax, estate, and succession planning—ideally starting more than a year before launching a sale process.
• Communicate proactively with family about the changes to come and consider frameworks for handling external requests after liquidity.
• Let the dust settle before making more major life decisions—they can wait until after the transaction is complete.
• “You don’t have to do this alone”—bring in experts and let them support you through this intense, transformative period.

Recommended Next Steps: If you’re even considering an M&A or fundraising event, begin planning and team-building as early as possible for optimal outcomes.

This summary reflects the content and tone of The Path to Exit Episode 35 (“Pitfalls to Avoid on the Path to an Exit”), focusing on actionable insights and practical advice for founders heading toward liquidity events.