25. Inside the Investor’s Mind: Lessons & Insights on Navigating the Startup World | Jag Singh

Hey there Risers and Thrivers,  In this episode of On The Up & Up, we’re joined by Jag Singh, a charismatic serial entrepreneur, investor, and former political strategist turned angel investor. Jag takes us on a journey through his unconventional path—from building tools for political campaigns to becoming one of Europe’s most active early-stage investors. We dive into the realities of startup life, exploring the highs and lows of entrepreneurship, what investors really look for in founders, and how resilience and customer-centricity are critical for success. Jag also offers candid insights into the challenges of founding a company in Germany, how to navigate bureaucratic hurdles, and why understanding the "rules of the system" is key to thriving in any startup ecosystem. Whether you’re a founder looking for guidance, an aspiring entrepreneur ready to take the leap, or simply curious about what it takes to succeed in the world of startups, this episode is packed with actionable advice and inspiration. – Follow us on your favorite podcast streaming channels and social media platforms:  (https://linktr.ee/ontheupandup_podcast⁠) – Acknowledgments Intro/Outro & Interlude Music: Music by ⁠⁠oussama arichi⁠⁠ from ⁠⁠Pixabay⁠ -- Timestamps 01:56 Jag Singh's Political Beginnings 03:31 From Politics to Entrepreneurship 08:29 Lessons from Early Startups 14:20 Challenges in the German Startup Ecosystem 21:48 The Bureaucratic Hurdles 25:02 Challenges for Non-EU Founders 28:02 The Reality of Startup Failure 30:28 Navigating the German Business Ecosystem 43:41 Connecting with Investors and Final Thoughts