In the 2nd part of the Startup Graduate series, Coll + Rich swap war stories from their early startup days — the wins, the weird job titles, and the era of naïve enthusiasm that brings you the from entry to expertise edition. In this episode, the dynamic duo dig deeper into the challenges and triumphs of breaking into the real startup world, offering valuable insights into the hiring process, the chaos, the scrappiness the importance of aligning passions with professional goals, and, why winging it doesn’t cut the mustard in the hyper competitive market of 2025. Whether you're a new grad, career switcher, or just startup-curious, listen to us unpack what it really takes to get in the door, and what to watch out for once you’re inside.Key Discussion Points: Getting into a startup is often the hardest part.How to evaluate a startup’s: funding - how to politely ask if there’s actually money in the bankculture - does their Glassdoor page read like a thriller novel  future plans before joiningThe truth about inflated job titles (and how they can hurt your career)Red flags in the hiring process: when does too many interviews become too many? How using your passion can help you to overcome the challenging times and to succeedIf you’ve ever found yourself wondering whether “fast paced environment” really means “mild panic at all times” this one is for you! Listen in, join the debate and let us know your comments. Get us at @thatshouldbeworkingpod on Instagram, LinkedIn and TikTok.

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