You Make It Look Easy Podcast

Elston Sam
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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. JUN 5

    Unexpected promotion to lead Asia’s largest tech media company (ft. COO of Tech in Asia)

    From an unexpected career path to getting acquired, Maria Li reveals what she's learnt about successful startups. In this episode, we talked about her journey from Apple's Silicon Valley HQ to leading Asia's top tech media platform. What You'll Learn: - Insider's perspective on the SPH acquisition - Understanding the pillars of a successful media company - Transitioning from a corporate job to startup founder - What it takes to start your own company - AI and tech trends in emerging markets in Southeast Asia Timestamps: 0:00:00 - Trailer 0:09:02 - The world's fastest promotion 0:16:02 - Detailed breakdown of SPH's acquisition 0:26:22 - How did SPH convince you? 0:39:19 - What are the traits of a successful business owner? 0:47:20 - AI Agents for local solutions 0:58:12 - Work-life balance??

    1h 1m
  2. Startup Secrets After Raising Over $20,000,000 (Former Hoolah CEO)

    MAY 15

    Startup Secrets After Raising Over $20,000,000 (Former Hoolah CEO)

    I'm joined by the CEO & Cofounder of Hoolah (Stuart Thornton), a Singapore based payments company, last valued at over $100M after being acquired by ShopBack. In this episode, Stuart breaks down the brutal realities of startup life, how they got the idea for the business, and the process of raising more than $20,000,000. Learn how he transformed his corporate experience into a successful fintech business and the critical lessons about validation and entrepreneurial commitment. Beyond the glamorous startup headlines, this conversation offers practical insights for aspiring entrepreneurs. Stuart candidly discusses the tough sacrifices, explains why not everyone is suited to startup life, and shares how to validate business ideas with minimal resources. Discover the importance of finding the right co-founders and why solving a "burning house problem" matters more than technology itself. Chapters: 0:00:00 - Trailer 0:02:00 - Why Stuart is the right person to talk about startups? 0:11:20 - How did Hoolah even start! 0:19:58 - No one understood what we were pitching 0:28:02 - How did you raise more than $20,000,000 0:39:08 - Deciding between passion vs fund raising hype 0:41:02 - Getting acquired by ShopBack (behind the scenes) 0:49:34 - How do I start a business with $0 0:53:23 - Difficult sacrifices no one talks about 0:59:23 - If you had $10k today, what business would you start

    1h 10m
  3. How this founder went from selling sneakers to growing a $100B protocol at Coinbase (Ft. David Tso)

    MAR 21

    How this founder went from selling sneakers to growing a $100B protocol at Coinbase (Ft. David Tso)

    From founder to investor, and now a key player at Coinbase, David Tso is on a mission to help bring the global economy onchain. In this episode, we dive into his journey: from losing his sneaker business to finding conviction in crypto, and now supporting creators & founders build viral products in support of Base's 2025 goal of $100B AUM. We cover everything from $TRUMP, the memecoin craze, to the political tailwinds shaping crypto — including how Trump's pro-crypto stance is influencing sentiment and adoption. Tune in for a raw, insightful conversation with someone building at the frontlines of crypto adoption. Highlights: 0:04:01 - First explanation of blockchain, discussing decentralization and removing intermediaries 0:08:40 - Trump's memecoin and its impact 0:18:37 - David's personal story about being deplatformed from his Instagram sneaker blog 0:23:10 - Connection between sneaker culture and early NFT adoption 0:28:38 - Factors for builders to consider when choosing a blockchain protocol 0:33:03 - Base's bold mission of 25 million users and 100 billion AUM by 2025 0:37:26 - How to go viral in crypto

    39 min
  4. Leading the AI race in Singapore: CEO of Hypotenuse AI, Joshua Wong

    FEB 13

    Leading the AI race in Singapore: CEO of Hypotenuse AI, Joshua Wong

    In episode 10, I am joined by Joshua Wong, the founder & CEO of Hypotenuse AI. Theposter child of AI in Singapore, and a close friend whom I've known for over 10 years, it's my privilege to be able to share his story. If you're an aspiring entrepreneur, founder, or planning to be one, this episode would give you theraw perspectives of that journey. We covered: - how he learned coding from hackers - troubled teenage years with gangs & failed exams - choosing startups over corporates - getting snubbed by early investors - perks of being in Y Combinator - predictions on the AI landscape Highlights: 00:00:00 - Trailer 00:07:19 - Striking the startup lottery with ShopBack 00:09:01 - Why did you choose startups over corporate 00:16:08 - Learned coding to seek revenge on a RuneScape hacker 00:21:03 - Gangs & failed exams 00:28:41 - Y Combinator, Sam Altman, snubbed by investors 00:34:32 - When AI exploded 00:43:59 - "Maybe slightly embarrassing..." 00:54:26 - Foundational layer vs Application layer of AI 01:04:00 - Prediction on the future of work Hope you enjoy this, and be inspired to take that leap of faith in building the startup ecosystem in Southeast Asia. Thank you :)

    1h 13m
  5. 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
  6. 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
  7. Reinventing the $31B Anime Industry: The Untold Story of Azuki’s Founder

    12/13/2024

    Reinventing the $31B Anime Industry: The Untold Story of Azuki’s Founder

    How did a teenage obsession with Pokemon and Runescape spark a global movement to transform the $31B anime industry? In episode 7, I sit down with Alex Xu (aka Zagabond), founder of Azuki, the groundbreaking NFT project with over $2B in trading volume. We explore his journey from childhood hobbies to a career at Google and Amazon, and how he built one of the most innovative ventures in the anime and NFT space. Alex shares the highs and lows of his entrepreneurial path, including controversies that shaped him as a leader. We also dive into Azuki’s future plans, including the acquisition of Anime.com and his vision to democratize the anime industry. Whether you’re a fan of NFTs, anime, or entrepreneurship, this episode is packed with insights and inspiration. Don’t miss it! Highlights: 00:00:00 - Trailer 00:10:47 - Correlation of childhood trauma & founder success 00:15:18 - How RuneScape & Pokemon cards made a difference 00:25:55 - Sparking a $1.9B dollars global movement 00:29:56 - "Now they want to see this character fail" 00:41:27 - Reinventing Anime.com 00:49:59 - What would you say to 20 year old Alex Xu? Full access: https://beacons.ai/ymile_podcast Tiktok: https://www.tiktok.com/@youmakeitlookeasy

    53 min
  8. From Acquisition to COO: Scaling Traveloka to 40 Million Users

    12/06/2024

    From Acquisition to COO: Scaling Traveloka to 40 Million Users

    A startup idea born at a bus stop? In episode 6, I sat with the ex-COO of Traveloka, Alfan Hendro, to explore how identifying simple customer problems can spark game-changing businesses. Alfan shares his entrepreneurial journey, starting as a lecturer in Brunei, where he founded SG House, a real estate property portal later acquired by iProperty Group. From there, his journey took him to Indonesia, where he built Voucher Hotel, a hotel booking platform, before joining Traveloka, Southeast Asia’s leading travel tech unicorn, to scale its hotel booking business and tackle unprecedented challenges during the COVID-19 pandemic. Now leading his latest venture, RevScaler, Alfan focuses on acquiring and supercharging enterprise SaaS businesses. In this conversation, he highlights the role of curiosity, adaptability, and mentorship in overcoming obstacles and building successful ventures. Whether you’re an aspiring entrepreneur or a seasoned founder, this episode is packed with insights to inspire and guide your journey.

    1h 1m
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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.

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