Choose Courage Inc.

Vivianne Castillo
  • 5.0 (33)
  • BUSINESS

We're reimagining business and workplace experiences with we-aint-afraid-to-go-there conversations. Choose Courage Inc. is an experience designed for leaders, entrepreneurs, and visionaries who are ready to break free from outdated norms and build workplaces, experiences, and businesses where people, creativity and courage come first.

  1. Ep 50 | Reclaiming Imagination in a World That Stifles It (ft Lauren Celenza)

    5D AGO

    Ep 50 | Reclaiming Imagination in a World That Stifles It (ft Lauren Celenza)

    Welcome to Choose Courage Inc. — where we skip the boring intros and jump straight into reimagining business and workplace experiences with we-ain’t-afraid-to-go-there conversations. And for this episode we’re going to skip the sugarcoating and get real about the messy, uncertain, and liberating journey of rethinking work and creativity. Vivianne Castillo sits down with Lauren Celenza, software designer, writer, and interview journalist, to dive deep into the power of community, creativity, and reimagining the future of work and life. From festivals to entrepreneurship, from reclaiming imagination to questioning the way we use our time, this conversation is an invitation to step out of the mundane and into something more alive. Expect an unfiltered conversation about: • The courage to reclaim agency in a world that discourages imagination • Why festivals, not conferences, might be the future of innovation • How the passing of time is the only certainty and why that should push you toward change • How small steps, not perfect plans, build the foundation for bold moves • Why creativity isn't a luxury but a necessity for meaningful connection If you’ve ever felt the pull toward something bigger but found yourself hesitating, consider this your sign to start. The future isn’t waiting for perfection, it’s built by those willing to take the first step. Hit play and let’s get into it. _____ • If this episode resonated, share it with an entrepreneur who’s tired of grinding and ready to build something that actually feels good. • Follow Vivianne on LinkedIn (https://www.linkedin.com/in/vccastillo/) for more reflections on courage, creativity, and regenerative entrepreneurship.

    38 min
  2. Ep 49 | Money, Power and the Lies You’ve Been Told About Success (ft. Ash Hynie)

    MAR 1

    Ep 49 | Money, Power and the Lies You’ve Been Told About Success (ft. Ash Hynie)

    Welcome to Choose Courage Inc. where we skip the boring intros and jump straight into reimagining business and workplace experiences with we-ain’t-afraid-to-go-there conversations. In this episode, Vivianne Castillo, Founder and CEO of HmntyCntrd and moonpaws, and Ash Coleman Hynie, Founder and CEO of CountrPT, talk about the uncomfortable, the unspoken, and the unapologetic realities of money, power, and persistence. No fluff. No clichés. Just straight talk and real strategies. They cover topics like: • Why fundraising feels personal and how to stop making it that way • The silent treatment: when friends ghost your investment ask • The biggest lies we’ve been told about money, power, and success • Why not all money is good money and when to say no • The unspoken power moves that separate struggling entrepreneurs from thriving ones • How shifting your mindset can open doors (and bank accounts) Whether you’re a founder navigating your first raise, an entrepreneur shifting your money mindset, or just someone tired of the same old "hustle harder" advice, this is for you. _________ • If this episode resonated, share it with an entrepreneur who’s tired of grinding and ready to build something that actually feels good. • Follow Vivianne on LinkedIn (https://www.linkedin.com/in/vccastillo/) for more reflections on courage, creativity, and regenerative entrepreneurship.

    46 min
  3. Ep 48 | Real Talk: What do you tell folks who feel stuck? (ft. Vincent Brathwaite)

    FEB 22

    Ep 48 | Real Talk: What do you tell folks who feel stuck? (ft. Vincent Brathwaite)

    If you’ve been telling yourself you’re “too deep in” to change, this episode is for you. Vivianne and Vincent unpack the fear hidden inside responsibility, the psychology of sunk costs, and why staying put is often just practiced survival, not alignment. This is a conversation about identity, agency, and what becomes possible when you stop confusing familiarity with safety. In This Episode, We Explore: • Why “too deep in” is usually attachment, not reality. • The sunk cost fallacy and how it distorts your future. • How identity gets fused with your job and why that makes leaving feel like self-erasure. • Why exhaustion shrinks your imagination. • The difference between certainty in place and uncertainty in motion. • How corporate systems quietly train learned helplessness. • Why movement creates clarity that standing still never can. They also explore a simple but confronting shift: Instead of asking what you’ve already invested… ask what you want the next 10–15 years to feel like. If you’ve been waiting to feel ready, calling misalignment “practical” or have been telling yourself you should just endure, this episode is just a friendly reminder that you’re not behind. ____________ •If this episode resonated, share it with an entrepreneur who’s tired of grinding and ready to build something that actually feels good. •Follow Vivianne on LinkedIn ( https://www.linkedin.com/in/vccastillo/ ) for more reflections on courage, creativity, and regenerative entrepreneurship. _______ Resources Mentioned: Vivianne shares two practical tools to help you move from reflection to action: •Life Audit Workbook from Episode 19, designed to help you spot misalignment before burnout and reclaim your agency. (https://choosecourageinc.kit.com/da998c495d) •Prototype Your Purpose (30-Day Framework) from Episode 23, a step-by-step guide to stop “finding” purpose and start experimenting your way toward clarity. (https://choosecourageinc.kit.com/362352e7c4)

    18 min
  4. Ep 47 | Real Talk: What's Keeping You Stuck (ft. Vincent Brathwaite)

    FEB 18

    Ep 47 | Real Talk: What's Keeping You Stuck (ft. Vincent Brathwaite)

    If you’ve been feeling stuck in a career that looks stable on paper but quietly feels misaligned, this episode is for you. Vivianne and her guest Vincent unpack the subtle narratives that keep designers frozen, stories that sound responsible, wise, even grateful… but are often just fear in disguise. In this honest conversation, Vivianne and Vincent explore the hidden beliefs that keep so many designers in place, including: The arrival fallacy: believing you’ll feel ready once you learn one more thing. •How “I just need more information” can mask fear of movement. •Why stability is often labeled responsible, even when it’s draining you. •How gratitude can quietly become a leash. •The fear of “starting over” and having to prove yourself again. •Staying past alignment because leaving feels like failure. •The difference between protecting your comfort and expanding your life. They also challenge a hard question: When you’re afraid of failing… failing in the eyes of whom? Because many designers aren’t lacking courage … they’ve simply been taught that staying still is the responsible choice. If you’ve been carrying quiet dissatisfaction but calling it practicality… If you’ve been waiting to feel “ready”… If you’ve been telling yourself you should just be grateful… This conversation will resonate. You don’t have to endure what no longer fits. And choosing yourself isn’t recklessness, it’s precision. __________ If this episode resonated, share it with an entrepreneur who’s tired of grinding and ready to build something that actually feels good. Follow Vivianne on LinkedIn (https://www.linkedin.com/in/vccastillo/) for more reflections on courage, creativity, and regenerative entrepreneurship.

    23 min
  5. Ep 46 | The Unspoken Cost Of Staying at Your Job

    FEB 15

    Ep 46 | The Unspoken Cost Of Staying at Your Job

    If you’ve ever felt the slow erosion of staying in a job that looks “good on paper” but feels heavy in your body, this episode is for you. Vivianne shares the real cost of remaining in environments that require self-neglect as a condition of employment and challenges the one-sided way we’ve been taught to think about risk. This isn’t just about leaving a company. It’s about choosing yourself before something essential in you disappears. In this deeply personal episode, Vivianne revisits ⁠the resignation letter⁠ she wrote when she left Salesforce (view here: https://bit.ly/4c0n1yF) and reflects on how the same cultural patterns continue to surface years later. But this episode isn’t a corporate takedown ... it's a broader conversation about: •What it costs to stay in environments that don’t protect you. •How toxic systems require your self-abandonment to function. •The difference between confidence and conviction. •Why the “safe” choice is often just the familiar one. •What it actually means to bet on yourself. If you’ve been carrying a quiet resignation letter in your head, this conversation will resonate and help you choose you. And if you’re in a season of questioning what’s next and want a space to talk it through, Vivianne invites you to book a 30-minute conversation at: https://calendly.com/choosecourageinc/lets-connect-and-vibe Because sometimes choosing yourself starts with simply saying out loud: “There has to be more than this.” __________ If this episode resonated, share it with someone who needs permission to choose themselves and don’t forget to leave a review to help others discover Choose Courage Inc💙

    26 min
  6. Ep 45 | How to Book Your First 10 Discovery Calls

    FEB 7

    Ep 45 | How to Book Your First 10 Discovery Calls

    In this episode of Choose Courage, Inc., Vivianne shares a training from inside her coaching community that helped members feel more confident, less avoidant, and more connected to the possibility of their first sale. Rather than teaching funnels or hype-driven tactics, she offers a grounded framework for booking your first 10 discovery calls through integrity, proximity, and thoughtful outreach. At its core, this episode is about replacing fear-driven avoidance with courageous conversation. Not to close deals but to practice, learn, and build real momentum. From there, she introduces a clear distinction: Inbound is about being found. Outbound is about being willing This episode focuses on outbound, not as chasing or convincing, but as relational courage in action. •The Three-Circle Framework for Aligned Outreach:Rather than starting with strangers, Vivianne encourages entrepreneurs to begin with proximity and trust. •A Different Way to Think About Discovery Calls: This episode challenges the pressure-filled belief that every call must turn into a client. •Outreach Without the Ick: Rather than scripts that manipulate or pressure, Vivianne shares principles behind outreach that feels clean. ______ If this episode resonated and you want support putting it into practice, ⁠download the outreach templates⁠ (https://choosecourageinc.kit.com/69a53b8b31) and choose one message to send this week. You don’t need to do everything. You just need to start.

    25 min
  7. Ep 44 | Can You Build an Anti-Capitalist Business Under Capitalism?

    FEB 1

    Ep 44 | Can You Build an Anti-Capitalist Business Under Capitalism?

    Welcome to Real Talk, a short segment on the Choose Courage Inc. Podcast dedicated to answering honest questions from people who are building businesses (or seriously considering it) while they’re still in the mess of entrepreneurship. This conversation was originally recorded for our Wednesday Real Talk series, but it felt too timely to hold, so we’re sharing it early. In this episode, Vivianne is joined by designer-turned-entrepreneur Vincent Brathwaite for a grounded, honest conversation exploring today’s question: Can you really build an anti-capitalist business under capitalism, or are we just performing opting out? Together, they unpack the difference between capitalism and commerce, the subtle ways extraction shows up even in values-led businesses, and what it looks like to design work rooted in care, courage, and creativity instead of burnout and exploitation. ____________ If this conversation resonated, please consider sharing this episode with an entrepreneur who’s tired of the grind and ready to build something that actually feels good to run. It might be the nudge and encouragement that they need. And if you’re feeling the pull toward the Creative Rebellion but aren’t sure how to redesign your business without burning it all down, explore how we can support you at choosecourageinc.com. Remember: you don’t have to build differently alone.

    16 min
  8. Ep 43 | Real Talk: Are You Too Broke NOT to Start a Business? (ft. Vincent Brathwaite)

    JAN 28

    Ep 43 | Real Talk: Are You Too Broke NOT to Start a Business? (ft. Vincent Brathwaite)

    Welcome to Real Talk, a short segment on the Choose Courage Inc. Podcast dedicated to answering honest questions from people who are building businesses (or seriously considering it) while they’re still in the mess of entrepreneurship. Sometimes the questions come directly from our community. Other times, they’re the exact questions we’re asking ourselves in real time. Either way, the goal isn’t to teach you how to do business “the right way”, it’s about doing it with courage, clarity, and care. In this episode, Vivianne is joined by her friend and designer-turned-entrepreneur Vincent Brathwaite for a grounded, honest conversation about money & risk as they answer today’s question: “Are you too broke to start a business or too broke NOT to?" ---- Join our email list to stay in the loop on new podcast episodes, freebies, and other experiences related to challenging the status quo of entrepreneurship here👉 https://choosecourageinc.kit.com/af70a78cb5

    13 min
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5
out of 5
33 Ratings

About

We're reimagining business and workplace experiences with we-aint-afraid-to-go-there conversations. Choose Courage Inc. is an experience designed for leaders, entrepreneurs, and visionaries who are ready to break free from outdated norms and build workplaces, experiences, and businesses where people, creativity and courage come first.

Information

  • Creator
    Vivianne Castillo
  • Years Active
    2025 - 2026
  • Episodes
    52
  • Copyright
    © Choose Courage Inc. | 2025
  • Show Website
    Choose Courage Inc.

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