Bob Jones, guest instructor for MIT's 15.393 Nuts and Bolts of New Ventures (IAP 2025), talks through the emotional side of startup life that most entrepreneurship courses skip. Drawing on stories founders have shared with him directly, he covers the heartbreak, isolation, and psychological strain that can come with building a company, alongside the motivations that draw people into entrepreneurship in the first place. Rather than a how-to on fundraising or product-market fit, this session treats the personal cost of the founder path as a subject worth examining on its own terms, using real accounts of setbacks and disillusionment to ground the discussion. Recorded as part of MIT's January IAP intensive on new ventures, it runs 73 minutes and functions as a candid counterweight to the more technical sessions in the course.