What to Do When Most of Your Net Worth Is in a Private Company
In this episode of EWA's FIN-LYT Podcast, Matt Blocki, Jamison Smith, and Weston Conway break down what it really looks like when 80 to 95 percent of your net worth is locked up in a single private company. Weston, a long-time EWA client and COO of Closing Lock, shares his firsthand experience taking an 80 percent pay cut to join a two-person startup that has since grown to 100 employees, raised $50 million in venture funding, and services a significant portion of the U.S. real estate market.
The conversation covers the emotional and financial weight of being "rich on paper" with no way to access that wealth until a future liquidity event. Weston explains how the Jeff Bezos regret minimization framework shaped his biggest career decisions, why he took chips off the table when the opportunity came, and how he resisted lifestyle inflation even after a secondary sale. Matt and Jamison dig into the practical planning side, from exercising stock options and 83B elections to trust and estate strategies for younger founders and operators sitting on fast-growing equity.
For anyone evaluating a startup opportunity, the team walks through how to think like an investor when picking a company to join, including how to assess customer acquisition cost, net dollar retention, and product roadmap. They also explore when it makes sense for a private business owner to bring in outside capital and what to watch out for when venture or private equity investors enter the picture.
Whether you are a founder, early employee, or business owner with most of your wealth tied to a single illiquid asset, this episode offers a real-world roadmap for making smarter financial decisions at every stage. Be sure to like and subscribe for weekly conversations that help you align your wealth with the life you want to live.
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