How to Actually Understand Startup Equity
Equity is one of the biggest reasons people join early-stage companies, and one of the least understood parts of any offer. In this episode, the VHTB team digs into why equity feels so opaque, what the different types of stock-based compensation actually mean, and how candidates and founders can talk about it without confusion or hype.
Matt Gjertsen of Better Every Day Studios is joined by Seyka Mejeur of AdAstra Talent Advisors and Justus Kilian of Space Capital for a practical walkthrough of the equity structures that show up in real startup offers: restricted stock, ISOs, NSOs, and RSUs. They break down how each one works, the tax traps people don’t see coming, and why liquidity and valuation paths matter more than the raw number of shares.
We also get into the human side, why candidates often feel embarrassed to ask “basic” questions, how past experiences at places like SpaceX or Amazon shape expectations, and what sophisticated founders do differently when communicating equity. Whether you’re a candidate trying to make sense of an offer or a founder trying to explain one, this episode gives you the tools to translate equity into real-world outcomes instead of guesswork.
Episode Highlights
00:00 Why equity feels confusing for almost everyone
01:47 A simple breakdown of restricted stock, ISOs, NSOs, and RSUs
04:52 Tax considerations most candidates overlook
07:26 Why liquidity plans matter more than people think
09:44 The perspective candidates bring from previous companies
11:50 How to ask “dumb questions” without feeling dumb
14:36 How great founders communicate equity and valuation paths
17:04 Building a simple spreadsheet to model potential outcomes
19:39 Using an investor mindset when evaluating job offers
Episode Takeaways
- Don’t guess, get clarity: Understand how each equity type works, what it costs to exercise, and the tax implications.
- Ask about liquidity early: “When could this be worth something?” is a fair question, not a taboo one.
- Build simple scenarios, zero outcome, base case, upside case, so you know what you’re signing up for.
- Look at the company like an investor: Why this team? Why this mission? Why now?
- Equity is a portfolio: Most careers include a handful of high-risk, high-reward bets; choose them deliberately.
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