Fundraising: Demystified! True Stories Direct From Founders

Most founders fail for psychological reasons—not tactical ones. In this episode of $100M Exits, Jason Kirby sits down with Aram Attar, founder of The VC Factory, to unpack the hidden psychology shaping fundraising outcomes, VC decisions, and why smart founders keep repeating the same mistakes. With 15+ years advising founders, sitting on boards, and training venture capitalists, Aram shares a clear conclusion: most failures aren’t about intelligence, strategy, or effort—they’re about how decisions are made under uncertainty. They explore the difference between trying to win versus trying not to lose, how VC psychology impacts fundraising more than your pitch, the hidden risks in earnouts and partial exits, and why the strongest teams balance promotion- and prevention-focused thinkers. Subscribe & get our free investor/buyer list at https://thunder.vc Key Takeaways Why founders repeat mistakes—even after seeing others fail Trying to win vs trying not to lose How VC psychology shapes fundraising outcomes Risks in earnouts, partial exits, and misalignment Why balanced thinking drives better decisions What you’ll learn in this episode Why a “5-year plan” often turns into a 20-year journey How VCs avoid the sunk-cost trap in bridge financing The mindset frameworks behind outlier investment betsHow to spot “what can go right?” vs “how do I not lose?” investors The #1 mistake first-time fund managers make with fund size Raising capital? Get a list of vetted VCs for FREE:https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode104&utm_id=%24100M++Exits Get the latest fundraising insights:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode104&utm_id=%24100M++Exits Timestamps: 00:00 Introduction 00:39 A 20-year journey to a $2.2B exit 01:57 How VCs make decisions 03:50 Investing in a Mexican retail company 06:20 What mindset-based investing really means 10:04 Behavioral insights every founder should know 15:34 Research behind successful VC thinking 23:43 Missed deals and costly VC mistakes 24:20 How investment committees really work 24:51 The champion rule in venture capital 26:06 Inside the investment committee process 29:37 Why founder empathy matters 33:04 The power of honest communication 36:28 How to evaluate emerging fund managers 43:01 Advice for new fund managers 46:29 Final thoughts and key resources ABOUT ARAM Aram Attar is a venture capitalist and founder of The VC Factory, focused on improving venture outcomes by shaping how investors and founders think, decide, and align. His work spans advising VC funds, CEOs, governments, and accelerator programs, with an emphasis on psychology, character, and long-term performance. LinkedIn: https://www.linkedin.com/in/aram-attar/ Website: https://thevcfactory.com/ ABOUT JASON KIRBY Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders navigate capital strategy and M&A. A serial entrepreneur with four exits, Jason has coached hundreds of founders and led transactions totaling $200M+ through Thunder. Email: jason@thunder.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT $100M EXITS $100M Exits equips founders with the insight and guidance needed to navigate capital strategy through conversations with founders and investors who’ve already done it. Best suited for founders doing $5M+ in revenue. Be sure to subscribe and let us know who you want us to interview next.