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