What happens after you sell for $975M? Not what you'd expect

Explore how successful entrepreneurs often face an unexpected crisis of meaning after achieving their ultimate goal of a significant exit.

What you'll learn:

• Why even massive financial success can lead to a profound sense of loss and purposelessness

• How the psychological challenges of post-exit life are far more universal than most realize

• A proven framework from Yale School of Management that has helped multiple founders navigate their "what's next" journey

(Reply to this email, and I’ll send you the Yale research paper!)

The Story: When Success Feels Empty

When Vinay Hiremath sold Loom to Atlassian for $975 million in 2023, he found himself doing something unexpected: climbing Himalayan peaks and then working briefly for a Department of Government Efficiency before escaping to Hawaii to study physics. As he wrote in a raw and honest blog post, "Life has been a haze this last year... I have infinite freedom, yet I don't know what to do with it."

Working closely with multiple founders who've had nine-figure exits in 2024, I've witnessed this same pattern play out repeatedly. One client, who sold their company for over $300 million, told me: "I can do anything or nothing. Both options are equally terrifying." Another founder who achieved a similarly massive exit confided that they spend hours each day just sitting in their home office, paralyzed by the endless possibilities before them.

The Insight: The Identity-Purpose Matrix

What I've observed consistently is that these successful exits trigger what the Yale School of Management calls a "triad of loss" - the simultaneous disappearance of structure, meaning, and identity. When founders go from being the driving force behind a growing company to suddenly having unlimited options but no clear direction, they often experience what psychologists term "the paradox of success."

The Yale framework breaks this transition into four crucial phases:

1. Pause - Taking time to process the emotional impact

2. Reflect - Examining values and possibilities

3. Operationalize - Testing new directions through small experiments

4. Think - Continuously evaluating and adjusting the path forward

What's particularly striking is how universal these challenges are. Whether the exit was for $100 million or $1 billion, founders consistently struggle with the same core questions: "Who am I without my company?" and "What do I build next when I don't need to build anything?"

Your Quick Win: Building Your Post-Exit Navigation Plan

If you're approaching or have recently experienced an exit, here's a structured approach to begin finding your new north star:

1. Schedule Dedicated Reflection Time: Block out 2 hours this week for deep thinking about your values and what energized you most before the money became the primary motivator.

2. Create Your Identity Map: Draw two columns - in the first, list all the roles and identities you had while running your company. In the second, you can brainstorm new identities you'd like to explore that aren't tied to business success.

3. Design Three Mini-Experiments: Choose three small ways to test new possible directions (e.g., mentoring other founders, exploring a creative pursuit, or diving into a new field of study) without making significant commitments.

4. Set a 30-Day Check-In: Calendar a meeting with yourself one month from now to assess which activities provide the most sense of purpose and meaning.

Every successful exit is just the end of one chapter and the beginning of another. The key is to recognize that writing this new chapter requires as much intentional effort as building the business—it just requires different tools and metrics for success.

What post-exit challenge are you currently facing? I'd love to hear your story and share additional insights from what I've learned working with founders in similar situations.

Reply to this email, and I’ll send you the Yale research paper!