Whether you are on the verge of an IPO, have just experienced a liquidity event through a tender offer, or have been building up cash for a specific goal, you may be wondering, how you can optimize what you doing with your cash, above and beyond using a high-yield savings account. Here are some of the options I’ve been discussing with clients lately and have been using in client accounts to optimize large cash holdings (above $100k) with a focus on tax efficiency.   1)      Certificates of Deposit (CDs). Typically, CDs, like bank accounts, are FDIC insured up ..read more

The IPO window appears to be reopening, having almost completely shut down for the last 18 months. Instacart, the popular grocery delivery platform, made headlines at the end of August with its announcement of a long-anticipated initial public offering (IPO), signaling a significant development in the evolving IPO market. Instacart employees have experienced significant ups and downs over the last few years as the company’s valuation was slashed from $39b to $24b and finally to $13b. For Instacart staff receiving ISOs, NSOs, and RSUs, the fluctuating valuation has generated additional question ..read more

Here are a few of the books that I most enjoyed and had the largest impact on my thinking in 2020. I offer them in hope that you will find one that enriches your life as much as they have enriched mine.  Atomic Habits, James Clear. A perennial New York Times bestseller that explores a research-based system for how to make the most of our lives by building habits and processes to realize our most productive best selves. Impactful Quote: “The ultimate form of intrinsic motivation is when a habit becomes part of your identity. It’s one thing to say I’m the type of person who wants this. It’s ..read more

Maybe your first-year vesting cliff is about to arrive, and you’re wondering what to do with a sizeable bundle of Restricted Stock Units that are about to transfer to your ownership. Or maybe you’ve been at the same company for the last decade and mostly forgotten about the RSU stock that has stacked up in your equity account. When selling company shares in the San Francisco Bay area, I’ve found that many tech workers are left guessing and second-guessing themselves. This leaves people often selling shares at random or simply ignoring their equity. Over the last 18 months, it’s resulted in man ..read more

I’m excited to share the first installment of my guide for Figma staff preparing for the potential Adobe acquisition with a focus on tax planning. As a Figma employee on the brink of a significant liquidity event, I hope to help you approach this season with a clear understanding of how to prepare for the Figma/Adobe acquisition. Here, I’ll highlight specific considerations for navigating the tax complexity and follow with some thoughts on preparing to sell Adobe stock (Part II). What if regulators halt the deal? Before diving into what you can do to prepare for the Adobe merger, let’s take a ..read more

“Formula for success: rise early, work hard, strike oil.” –J. Paul Getty Planning your incentive stock option exercise strategy is both an art and a science. As a financial advisor who thinks about timing stock option exercises regularly, I’d like to share with you how the concept of leverage aids the “science” aspect of your decision. The “art” has more to do with the stage of your career or your start-up’s growth, which is another conversation altogether. The lever is a nifty invention. If you, like me, spent any time on a playground with friends and siblings as a child you may have experime ..read more

  As OpenAI continues to shape the future of our world, I have begun to hear from OpenAI staff who are seeking to effectively navigate realized liquidity and develop a plan for their wealth. I would like to briefly offer eleven general tools and strategies that can help you as an OpenAI employee purposefully manage your wealth and avoid costly pitfalls. 1. Manage your cash strategically. The failures of banks such as First Republic and Silicon Valley Bank have highlighted the importance of effective cash management. Firstly, ensure that you do not hold more than the FDIC deposit insu ..read more

Making money is art, and working is art, and good business is the best art. -Andy Warhol If you work in a start-up in San Francisco and have received Incentive Stock Options (ISOs) you may now be considering your best course of action. Should you exercise now, while the tax consequences are minimal, or wait until the company is successful? Do you prefer the risk of a high tax bill or the risk of exercising and then watching the value of your illiquid stock implode? There’s very little firm guidance on this, because everyone’s personal situation, risk tolerance, and start-up business model are ..read more

Dear Friends, During the year 2020, I observed impactful IPOs, home purchases, marriages, and new children reshape your lives. I saw some of you lose jobs, experience illness, and navigate major career transitions. It has brought me great joy to see how, without exception, you made it through stronger and better on the other side. 2020 emphasized that injustice and inequity are real and that we humans live on a fragile planet. But history shows us that overcoming challenges is what humans do. And I remain an optimist, believing that unprecedented challenges continue to offer us opportunities t ..read more

“People don't care how much you know until they know how much you care." ― Theodore Roosevelt Wouldn’t it be nice if every financial firm laid out its priorities, and every financial blogger and author shared with us their biases? Perhaps one of the reason’s the Department of Labor is in the process of implementing the new fiduciary laws is for this very reason: it’s hard to know where people stand. So, let’s just start here. With this blog now past it’s one-year anniversary, I first want to thank you for coming along on this journey over the last 14 months. I'd like to use the opportunity to ..read more