Ep 272 Startup Founder Pay, AI’s Impact, and Bootstrapping Trends with Pilot CEO Waseem Daher

Guest: Waseem Daher – Founder & Executive Chairman of Pilot LinkedIn: Waseem Daher Pilot: pilot.com | Founder Salary Report 2025

Bio

Waseem Daher is the Founder and Executive Chairman of Pilot, a modern finance team offering bookkeeping, tax, and CFO services for startups, e-commerce businesses, and professional services firms. Backed by Sequoia Capital and Bezos Expeditions, Pilot has become the go-to back office solution for growing companies.

An engineer by training and a serial entrepreneur, Waseem previously co-founded Ksplice (acquired by Oracle) and Zulip (acquired by Dropbox). He now combines his experience as a three-time founder with insights into startup finance, scaling, and leadership. Beyond Pilot, Waseem writes regularly about building startups on LinkedIn and in his newsletter, Startup Real Talk.

What You’ll Learn in This Episode

• Why founder salaries dropped 43% in 2025 and what this means for early-stage companies
• How founders should think about compensation when talking to investors
• Risks startups face when founders underpay themselves
• How company stage, funding, and geography influence salary decisions
• The role of boards and investors in shaping compensation
• What lessons Waseem carried from Ksplice and Zulip into Pilot
• Insights into bootstrapping vs. venture-backed founder pay
• How founders can use Pilot’s salary data to benchmark and negotiate effectively
• Why the number of AI startups surged by 287%, yet founder salaries declined
• What the rise in bootstrapped startups (up 77%) says about today’s funding environment

Disclaimer: The views expressed in this podcast are my own and are for informational purposes only. They do not constitute financial or legal advice, nor do they necessarily reflect the views of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC.