You Make It Look Easy Podcast

Elston Sam

We uncover the untold stories and strategies that propelled today’s top CEOs and leaders to success. I’m Elston Sam, and after years in big tech and raising over $10M for my own startup, I’ve had the privilege of meeting real-life role models who inspire me with their resilience and insights. Now, I’m sharing these powerful conversations with you, giving you direct access to the mindsets and lessons that fueled their journeys from the ground up.

  1. Serial Tech Founder: Raising Millions, Growth Hacks, and the Hard Truth About Startups

    JAN 28

    Serial Tech Founder: Raising Millions, Growth Hacks, and the Hard Truth About Startups

    Alex Shin is a serial entrepreneur with a resume that’s hard to match. He was a cofounder of Blind, the anonymous workplace chat app used by employees at Uber, Microsoft, and Google, which raised over $50M. He also co-founded Hashed, one of Asia’s leading crypto venture capital firms, managing over $500M in assets. In this episode, Alex reflects on his early days at DocuSign and Google, where he honed his skills in sales, team building, and venture capital—experiences that paved the way for his success as a multi-time founder. In his own words: “I’ve never been at a company that didn’t do well. It’s not me, it’s the market.” We dive into the harsh truths of startup life, the hidden advantages of adversity, and Alex’s secret growth hacks for scaling companies and acquiring users. Whether you’re an aspiring founder or a seasoned entrepreneur, this episode is packed with lessons and insights to help you thrive. Alex credits his journey to luck, but we explore how you can create opportunities to position yourself for success—and maybe even make your own luck. Highlights: 00:00 - Trailer 03:56 - "Never spoke about this publicly, I grew up in a really rough background" 07:54 - Learning how to crush at sales 19:14 - Acquiring users through dating apps & buying shots 28:18 - Being told that Microsoft CEO uses your app! 30:46 - The initial Blind usage - salaries, cute girls and dating 44:03 - "Crypto was originally about common wealth" More: TikTok, Instagram, Full access

    52 min
  2. Bringing Asia to Hollywood: The life story of 88RISING's Cofounder (Jaeson Ma)

    JAN 15

    Bringing Asia to Hollywood: The life story of 88RISING's Cofounder (Jaeson Ma)

    Explore the transformative journey of Jaeson Ma, co-founder of the acclaimed media company 88Rising. Discover how he overcame significant challenges, from growing up in a single-parent household to navigating the dangers of gang violence and petty crime. His turning point came with an unexpected awakening that reshaped his life’s direction. This episode delves into Jaeson’s unconventional rise, from aspiring rapper to working with the legendary MC Hammer. Through captivating stories, he reveals how he mastered the music industry, and ventured into the most valuable tech startups today. Along the way, he forged unique collaborations, including working with a young Bruno Mars before his global stardom. Jaeson’s resilience, vision, and unshakable purpose shine through as he shares his role in championing Asian representation in Hollywood, building entrepreneurial ventures, and making strategic investments in companies like Grab and TikTok. His story is a powerful testament to the impact of faith, adaptability, and the courage to pursue bold dreams, even in the face of overwhelming odds. Highlights: 00:00:00 - Trailer 00:08:31 - The chip on my shoulder 00:16:09 - I got caught 00:29:16 - 3 dimensions of life 00:44:13 - Investing in YouTube when they were 5 people 00:50:58 - Signing Bruno Mars for $1,500 01:05:26 - How Steph Curry, Kobe or MJ achieves success Full access: https://beacons.ai/ymile_podcast

    1h 13m

About

We uncover the untold stories and strategies that propelled today’s top CEOs and leaders to success. I’m Elston Sam, and after years in big tech and raising over $10M for my own startup, I’ve had the privilege of meeting real-life role models who inspire me with their resilience and insights. Now, I’m sharing these powerful conversations with you, giving you direct access to the mindsets and lessons that fueled their journeys from the ground up.