For years, the startup promise was simple:
Join early. Take less salary. Share in the upside.
It sounded like a fair trade — until the fine print appeared.
The real challenge? When paper equity meets real-world tax and timing rules.
With Andrew Endicott of Gilgamesh Ventures, we explored the hidden complexities of startup compensation — and how perception and structure don’t always align.
Founders often share the dream of “owning part of the company.”
But in most cases, employees receive an option to buy shares later — typically with a 90-day exercise window, limited financial visibility, and little immediate liquidity.
It’s not about blame — it’s about design.
And it’s a system that can work better for everyone.
▪️ Optimism ≠ Understanding
Most founders aren’t experts in capitalization tables.
Most employees aren’t trained to interpret preferred-stock structures.
And between those two optimistic groups, value can quietly fade — not in exits, but in expiration dates.
▪️ Liquidity as a Challenge
A strike price isn’t cash. Options can’t easily be financed.
When departing a startup requires paying to keep your shares, the structure itself may need updating.
▪️ A Smarter Equity Model
Andrew’s perspective isn’t about disruption — it’s about refinement.
✅ Extend exercise periods beyond 90 days.
✅ Consider granting stock directly, with companies covering related taxes where feasible.
✅ Redefine ownership as genuine participation, not just potential upside.
Because true equity should reward contribution — transparently and fairly.
Startups aspire to reshape industries.
Perhaps the next evolution is reshaping how they share success with the people who help create it.
Topics covered in the podcast:
(00:00) Episode intro – Rohit introduces TheOnePoint Podcast and guest Andrew Endicott
(01:01) Inside Gilgamesh Ventures – investing in the future of global fintech
(02:48) U.S. and international portfolio – why Latin America is a growth hub
(04:16) Fintech’s comeback and today’s topic: the evolution of employee ownership
(05:02) Understanding startup equity – how tax rules shape employee stock options
(08:23) Why employee stock options don’t always deliver expected value
(11:34) The communication gap – why equity education matters for teams
(16:10) How founders can create clarity and transparency in equity discussions
(18:54) Exercising stock options – timing, financing, and employee planning
(23:05) Rethinking company policy – extending exercise periods and real ownership
(24:51) Exploring common stock models and how tax support can help employees
(31:21) Lessons from leading companies – approaches to long-term employee rewards
(36:39) Key takeaways – building fair and transparent equity structures
Reach out to us:
Andrew Endicott: https://www.linkedin.com/in/andrewendicott/
Gilgamesh Ventures: https://www.gilgameshvc.com/
Rohit Yadav: https://www.linkedin.com/in/rohityadav23/
