In this episode of Tank Talks, host Matt Cohen sits down with Chris Canavan, founder and general manager of Canavan Private Wealth, to unpack one of the most confusing and emotionally charged chapters in a founder’s journey: life after the liquidity event.
Chris brings thirty years of global institutional and private office experience to the table, but his superpower is not managing money. It is designing and running the system around a founder’s wealth. After watching countless entrepreneurs exit their companies only to be overwhelmed by advisors, decisions, documents, and emotional pressure, Chris built a model that restores clarity, control, and purpose.
He explains how founders lose sight of their instincts amid a fire hose of new advisors promising the world, why trust erodes so quickly after a deal closes, and how fragmented systems lead to panic, confusion, and poor decisions. Chris breaks down the architecture of a modern private office, why most founders rely on sticky notes and spreadsheets, and how his closed-loop operational model gives founders their time back.
From early warning signs of wealth fragmentation, to the psychological crash founders face when purpose suddenly disappears, to his triage process for investment opportunities, Chris delivers a brutally honest guide to navigating life after the big exit.
Whether you are preparing for a liquidity event or already living through the post-sale fog, this episode shows you what founders get wrong, what they must put in place, and how to build a system that supports your next chapter rather than suffocates it.
Spotting the Gaps: Managing the System, Not the Money (03:38)
* How advisory silos fail ultra-high net worth individuals
* Why communication, not talent, is the biggest weakness in wealth management
* The role of the generalist who understands every silo deeply enough to connect them
* Why founders need someone three to seven feet deep across all disciplines
Finding the Right Clients and Building Trust-Based Relationships (07:06)
* Why fit, values, and authenticity matter more than money
* How Chris screens clients who actually want to be helped
* Why some founders treat advisors like commodities and how that destroys outcomes
* Building long-lasting relationships built on accountability and transparency
Managing Founder Emotions and Behaviors Post-Exit (09:00)
* Founders are used to speed, scale, and instant execution
* Why slowing down is the hardest adjustment
* How Chris handles frustration, urgency, and emotional volatility
* The importance of respect and boundaries when multiple advisors and egos collide
Early Warning Signs of Wealth Fragmentation (16:21)
* When day-to-day tasks start consuming founder’s mental bandwidth
* The “black flies in cottage country” analogy
* Why founders lose the ability to focus on what matters
* The fire hose of advisors and opportunities after an exit
How Chris Evaluates Investment Opportunities for Clients (25:09)
* Pain reliever vs. gain creator: the framework for evaluating pitches
* Why relationships and trust matter more than projected returns
* How Chris filters noise before presenting anything to a founder
* The story-first, numbers-second diligence process
The Psychological Crash After a Big Exit (28:17)
* Why life will never be the same after selling a company
* How society begins to define founders by the name of their exit
* The loneliness and loss of identity that shock new millionaires
* Why every human needs a sense of purpose to avoid emotional collapse
Becoming a Project Manager of Your Own Life (31:45)
* Why successful entrepreneurs struggle when their team disappears
* Trust-building, listening, and meeting founders where they areHow Chris transitions from advisor to integratorWhy trust cannot be demanded, only earned over time
Advice for Founders Preparing for an Exit (36:48)
* Why founders must build structure before signing final documents
* The danger of early engagement with performance-focused advisors
* Why founders need an unconflicted advisory boardHow to breathe, slow down, and avoid urgency-driven decisions
The Future of Private Wealth for Canadian Founders (40:10)
* Why founders will disrupt the private office industry
* The coming shift from advice to execution
* How operational efficiency will redefine wealth managemen
* The democratization of systems once reserved for legacy families
About Chris Canavan
Chris Canavan is the founder and General Manager of Canavan Private Wealth, a private office that provides institutional discipline and operational clarity to ultra-high-net-worth individuals. With a background at global institutions and Big Four firms, Chris specializes in helping founders navigate the complex transition after a liquidity event by managing the systems around their wealth, coordinating advisors, and helping them find renewed purpose.
Connect with Chris Canavan on LinkedIn: https://www.linkedin.com/in/chrislcanavan/
Connect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1
Visit the Ripple Ventures website: https://www.rippleventures.com/
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