We Raised $55M – But Would We Do It Again?

In this episode of Rich Lessons, Sheena and Sevetri break down the real, raw, and often untold truths behind raising $55 million in startup funding. From bootstrapping with $250 to navigating venture capital, angel investors, and dilution, this is the conversation every founder needs to hear before they raise.
They open up about control, pressure, trade-offs, and the emotional toll of building VC-backed businesses as Black women founders. If you're deciding between bootstrapping vs. venture capital, this episode will change how you see startup money forever.
💡 Key Topics:
• Bootstrapping vs. raising VC
• Angel investors & friends/family rounds
• How equity and ownership change over time
• The psychological cost of raising money
• Lessons from failed exits and successful pivots