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The Founder Breakup Playbook: Lessons From the Companies That Didn't Survive
Building a startup together tests everything you believe about trust.
In this episode, serial entrepreneur Lloyed Lobo and Melissa Kwan, CEO at eWebinar, unpack the cofounder confessions founders whisper but rarely admit: love turned liability, handshake deals gone wrong, and the quiet resentment that kills partnerships faster than failure itself.
From equity fights to emotional burnouts, they dissect why cofounder breakups feel worse than divorces, and the principles that keep the right ones from imploding.
00:41 Love, lies, and why 65% of startups fail from conflict
02:06 Handshake deals and the myth of “trust over paperwork”
05:46 The fairness trap: splitting equity before earning it
14:20 Why vesting clauses save friendships and companies
17:03 When one founder works harder and starts to resent it
32:36 How to rebuild communication when it turns personal
38:39 The truth about burnout, buyouts, and walking away
Follow Lloyed:
- LinkedIn: https://www.linkedin.com/in/lloyedlobo/
- Instagram: https://www.instagram.com/lloyedlobo/
Published on 1 month ago