The Holloway Equity Compensation Guide Revised for 2021

Joshua Levy (Holloway)
▪︎ 5 minutes read time

Our First Guide, Newly Updated

A few years ago, I started getting questions from friends and connections about how stock options, equity compensation, and taxes work. “I have an offer for 50,000 stock options. Hey, you’ve been in startups. Is that any good? How do I negotiate?”

Understanding ISOs, NSOs, RSUs, taxes, negotiations, and compensation packages has never been what I’d call fun. But it turns out it matters a lot. Knowledge about equitable compensation is what allows people in thousands of companies—employees, managers, founders, advisors, investors—to work together, share in the benefits of building new companies, and avoid costly or unfair pitfalls. It became a topic I reluctantly learned out of necessity, as I took on roles in various startups, as a candidate and when making offers.*

But it was frustrating that for something so complex, confusing, and critical to people’s careers, the existing resources were scattered and often incomplete or misleading.

Then I had a conversation with Joe Wallin, an experienced startup attorney who’s blogged for a long time on these topics.* We agreed this needed to change. What we pulled together as a GitHub document later evolved into the Holloway Guide to Equity Compensation. At least 250,000 people have read parts of the guide, and it is recommended at hundreds of firms, including top startups and venture firms.

Now, we’re pleased to announce a bunch of recent improvements, for “e2.1”, our first 2021 edition, based on reader feedback:

  • Advisor equity and typical advisor equity levels
  • The use of promissory notes
  • A newly polished downloadable version, including PDF and now EPUB
  • Other small edits and corrections

Please check it out and get access now. Note we also allow gift purchase (if you know someone who needs it) and team purchase—select those options at checkout.*

I’d like to thank Joe for his incredible expertise, devotion, and attention to detail on this work, and to the generous review and feedback from dozens of folks who have helped on the GitHub project and are listed in the credits.

Growing the Platform

Let me also mention one more change and how it fits with what we’re building at Holloway.

What motivates us is to imagine a new place online that nurtures the publication of in-depth knowledge. Where instead of daily tweets and hot takes, we find deeper insights we can return to. Expertise that lets us walk in the footsteps of others to navigate tough challenges in our life and work.* In addition to publishing content, we have built a platform for guides and books that is satisfying to use in the browser and that makes books easy to discover and easy to update—in ways that aren’t possible with blogs and most traditional books and ebooks. (See our catalog for over a dozen titles so far, with others coming soon.)

But one thing we’re sure of: it is essential to align incentives between content creators, the platform, and readers’ best interests.

Today, maybe more than ever, we are drowning in information but are still struggling to find trustworthy knowledge. We have come to learn how web and social media content is powered and shaped by ads, clickbait, lead generation, content marketing, and even viral disinformation. Content reflects the incentives of those who build it. These problems arise when publishers and writers are not incentivized to invest in long-term value for readers.

To encourage deeper and more nuanced writing means to funnel resources into authors and editors—and a platform that rewards unusual thoughtfulness and expertise. This isn’t quick or easy. It takes persistent effort. We’ve done the groundwork, including working with a wonderful and insightful initial group of authors, learning new ways to offer editorial and marketing support, and building a document platform and a quality reading experience that both works on the web and supports every format (web, ebook, and print). We now need to prove it can grow, supported by readers.

For that reason, although this first guide began free, full access is now paid, as with our other titles. Everyone still gets limited free preview access. We want to be sure Holloway titles are worth paying for to people looking for deeper knowledge, assembled with care. (We’ve kept the price on this guide low to continue to reach as many folks as possible. Contact us for academic or group discounts.)

If you’ve already purchased it, thank you! Please let me know your thoughts on this guide or any other titles on Holloway, or leave suggestions in the online book itself, which we review.

Read and be well,


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