'Til You Make It

Silvia Oviedo
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Some people trained to be Olympians and ended up on the red carpet. Some built tech companies. Some were chiefs of staff who became artists, writers who reinvented themselves mid-career, operators who walked away from everything to start over. 'Til You Make It is a conversation series about careers like these: the ones no one could have planned, that only make sense in retrospect. Each episode, host Silvia Oviedo (founder and CEO of Blomma and former executive at Canva and Pinterest) sits down with someone whose path makes no sense on paper and follows the thread back: the early ambition, the first unexpected turn, the irrational bet, the failure that redirected everything, and the people who saw something in them before they saw it themselves.

Episodes

  1. 4d ago

    Adaption Over Expertise - Scott Coleman

    The advice everyone gives about career growth is backwards: stop obsessing over the next title and start chasing the next thing you need to learn. Scott Coleman—the former Google and Pinterest operator who helped bring Google to Africa, led growth at Pinterest, and now advises founders through Atmosphere Partners—explains why the fastest way to get unstuck in a changing world is to get comfortable being a beginner again.If you’re watching AI rewrite the rules of work, this conversation is a reality check and a roadmap. Silvia Oviedo—a founder, former Pinterest and Canva operator, and Scott’s former manager—pushes into the questions that matter right now: how do you stay grounded when your job may not exist in six months, how do you keep up when the tools change every week, and what actually matters when anyone can build software faster than ever before?You’ll discover: Why the AI era puts everyone on a more even playing fieldHow to learn by doing instead of getting lost in theoryWhy the hardest problem is no longer building, but choosing what to buildWhat makes personalized software useful, and where it will stay thinWhy go-to-market, positioning, and distribution are becoming more important than everChapters 00:00 Introduction to Scott Coleman01:21 Scott's Early Career Journey05:44 Navigating Change in Technology09:35 Finding Balance in Career Growth12:26 The Importance of Practical Learning18:29 The Future of Personalized Products23:11 Traits of Successful People30:10 Scott's Passion for Climate Change32:33 Transitioning to Consulting34:40 Faking It Until You Make It

  2. Oct 12

    Painting Your Path - Pavan Vasdev

    The conversation covers Pavan Vasdev's transition from the music business to painting landscapes and exploring geopolitics through meditative videos. It explores the reality of the creator journey, misconceptions about the music industry, the role of a chief of staff, and the challenges of navigating ambiguity in the startup world. Pavan's focus on building a community and investigating compelling stories is a driving force in his career. Takeaways Career paths are not linearBuilding a community is a driving forceComfort in a sea of ambiguityFaking it till you make itChapters 00:00 From Music to Geopolitics03:02 Painting the Past: A New Creative Outlet04:00 Exploring Geopolitical Contradictions05:29 The Creator Journey08:13 The Music Business and Career Advice10:21 Misconceptions About the Music Industry19:32 The Role of Chief of Staff21:53 Navigating Ambiguity in the Startup World26:03 Building a Community and Investigating Stories

    Painting Your Path - Pavan Vasdev

  3. Oct 5

    Hone Your Craft - Jeremy Jankowski

    In this conversation with Jeremy Jankoski, we talk about career transitions, the rise of creators and the creator economy, the craft of creators, entering the workforce, adapting to change and the impact of AI, continuous learning and mentorship, career advice and self-reflection, authenticity and personal branding, navigating professional relationships and people dynamics, building symbiotic relationships and partnerships, exciting initiatives at The Lighthouse, and transitioning to a creator and personal branding. Follow Jeremy on: Instagram LinkedIn Takeaways Career transitionsAuthenticity in branding Chapters 00:00 Navigating Career Transitions02:26 The Rise of Creators and the Creator Economy04:33 The Craft of Creators and Working with Creators06:12 Entering the Workforce and Career Development08:29 Adapting to Change and the Impact of AI11:16 Continuous Learning and Mentorship13:26 Career Advice and Self-Reflection14:15 Authenticity and Personal Branding16:45 Navigating Professional Relationships and People Dynamics19:11 Building Symbiotic Relationships and Partnerships22:20 Exciting Initiatives at The Lighthouse and Future Outlook25:34 Transitioning to a Creator and Personal Branding

    Hone Your Craft - Jeremy Jankowski

  4. Sep 28

    Find your Why - Chloe Hall

    Chloe Hall's career journey involves a significant reinvention, transitioning from the corporate world to mission-driven work. Her path includes experiences in consulting, finance, and advertising, highlighting the importance of skills and transitions. The power of community and corporate engagement are central themes, leading to her impactful role at Ronald McDonald House. Chloe's ability to manage tough situations and her advice to her younger self provide valuable insights for listeners. Takeaways Career reinventionCommunity engagement Chapters 00:00 Career Reinvention02:05 From University to Consulting03:48 Skills and Transitions06:22 The Power of Community14:15 Corporate Engagement and Collaboration15:22 Engaging with Nonprofits22:15 Transition to Ronald McDonald House27:36 Managing Tough Situations30:19 Advice to Younger Self

    Find your Why - Chloe Hall

  5. Sep 21

    Renaissance Man - Bill Connolly

    The conversation with Bill Connolly explores the intersection of creativity, career, and personal growth. It delves into the impact of improv and comedy on professional life, the evolving landscape of creativity in the digital age, and the importance of embracing a Renaissance mindset. The discussion also touches on the role of AI in creativity and the resilience of human beings in navigating career challenges. Takeaways Renaissance MindsetCreativity in the Digital Age Chapters 00:00 The Intersection of Creativity and Career07:10 The Impact of Improv and Comedy on Professional Life15:26 The Role of AI in Creativity23:58 Embracing a Renaissance Mindset Links: Go to blomma.com for more, and use code TYMI for an additional month off coaching! Follow Bill's newsletter:

    Renaissance Man - Bill Connolly

  6. Sep 4

    Take The Risk - Siddhartha Dabral

    The conversation covers Sid's journey as a curious engineer, his approach to building solutions, empowering others with technology, creating conditions for exploration, the concept of 'faking it till you make it,' the importance of solving known problems, and the value of being comfortable with being uncomfortable. Siddhartha Dabral a serial entrepreneur. He currently is the co-founder of Blomma and has also co-founded Button and Floor. Takeaways Curiosity drives the journey of a curious engineer.Solving known problems is more valuable than solving anticipated problems. Chapters 00:00 The Curious Engineer03:16 Building Solutions and Finding Value06:02 Empowering Others with Technology09:45 Creating Conditions for Exploration14:46 Faking It Till You Make It23:12 Solving Known Problems31:01 Comfort with Being Uncomfortable Go to blomma.com for more, and use code TYMI for an additional month off coaching!

  7. Aug 26

    From Tech to the Red Carpet - Lex Niko

    Leaving Big Tech to Bet on Yourself—with Lex NikoWhat happens when the career you worked hard to build no longer feels like the career you want? Lex Niko had worked at some of the biggest names in tech—including Google, Amazon, and Pinterest—when she decided to take a chance on something far less predictable: herself. Today, Lex is a host, media personality, brand consultant, and the founder of Conversation Starters, a media company dedicated to keeping people in the cultural conversation. She has built an audience of more than 400,000 people and partnered with brands including Prime Video, the NFL, F1, F1 Academy, Meta, and E! News/NBCUniversal. In this conversation, Lex and Blomma founder Silvia Oviedo talk about the messy middle between knowing you want something different and actually doing something about it. They explore how curiosity can become a career compass, why confidence often comes after the leap—not before it—and what it really takes to build a public-facing career online. Lex also shares what she has learned about ambition, imposter syndrome, rest, and staying kind in industries that reward constant visibility. https://www.instagram.com/lexniko/ https://www.instagram.com/conversationstarters/ In this conversationHow Lex knew it was time to leave techWhy curiosity can be more useful than a perfect career planThe difference between taking a risk and giving yourself a chanceHow to trust yourself when the next step is ambiguousWhat people don’t see behind a successful online presenceWhy rest and self-care are part of the workWhat sports can teach us about kindness, respect, and characterManifesting a red carpet interview with the Heated Rivalry boys or Dua LipaChapters00:00 — When the career you built no longer fits02:23 — Leaving tech for a career in media03:59 — Following curiosity before you feel confident04:21 — The moment Lex decided to bet on herself05:38 — Why trying something is never wasted07:27 — The strengths that make big career moves possible09:02 — Learning to trust yourself in the unknown10:02 — Rest is not a reward10:56 — Imposter syndrome and learning in public14:31 — The invisible work behind an online career33:22 — What athletics taught Lex about kindness and respect Go to blomma.com for more, and use code TYMI for an additional month off coaching!

    From Tech to the Red Carpet - Lex Niko
  • 7 Episodes

About

Some people trained to be Olympians and ended up on the red carpet. Some built tech companies. Some were chiefs of staff who became artists, writers who reinvented themselves mid-career, operators who walked away from everything to start over. 'Til You Make It is a conversation series about careers like these: the ones no one could have planned, that only make sense in retrospect. Each episode, host Silvia Oviedo (founder and CEO of Blomma and former executive at Canva and Pinterest) sits down with someone whose path makes no sense on paper and follows the thread back: the early ambition, the first unexpected turn, the irrational bet, the failure that redirected everything, and the people who saw something in them before they saw it themselves.

Information

  • Creator
    Silvia Oviedo
  • Years Active
    2026
  • Episodes
    7
  • Rating
    Clean
  • Copyright
    © 2026 Silvia Oviedo