Dear Legacy... cover art

Dear Legacy...

Dear Legacy...

Written by: Kevin B. the Brand
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About this listen

Dear Legacy is where real stories meet real life. Hosted by Kevin B the Brand, this show is life after 40 what led before and what’s to come an open conversation about the journey of becoming as fathers, partners, entrepreneurs, leaders, creators, and living with purpose. Each episode is rooted in honesty and perspective, covering business, mental health, military, marriage, divorce, parenthood, blended families, identity, and the grind of building something meaningful.


Some episodes feel like open letters, others like the conversation you didn’t know you needed.


This show isn’t about perfection it’s about being present, growing through what shaped you, and choosing to build something that lasts. Whether Kevin is solo or with guests, the message stays the same: your story matters, your lessons matter, and your legacy is already in motion.


If you're navigating real life and defining your next chapter, welcome home.
Define it. Build it. Live it.
Subscribe and walk this journey with us.

© 2026 Dear Legacy...
Episodes
  • Dear Legacy: I Thought I Knew What Legacy Was… I Was Wrong.
    Jan 14 2026

    This is Dear Legacy… Episode 1, and this episode exists because I got checked.

    I didn’t come into this thinking I had legacy figured out. I thought I understood it until I did an AI self-reflection assignment created by Breana Hampton (@iambreham) that forced me to slow down and really look at myself.

    What came back wasn’t disrespectful.
    It wasn’t negative.
    But it was honest and I needed that.

    This episode isn’t about answers.
    It’s about realizing your thinking might be off… and being willing to admit it.

    I talk about:

    • How I thought I understood legacy and why I was wrong
    • Fear, procrastination, and why starting felt heavier than it should’ve
    • How AI became a mirror instead of a shortcut
    • Why waiting to feel ready is a trap
    • Why action matters more than confidence, clarity, or perfection

    This show isn’t coming from a place of “I’ve arrived.”
    It’s coming from a place of I’m starting and I’m doing it out loud.

    Dear Legacy… begins here not at the finish line, but at the moment I decided to stop overthinking and move.

    It’s time to Define It. Build It. Live It. Let’s Take this Journey Together.

    Why You Should Listen

    If you’ve ever told yourself “I’ll start once I have it figured out” this episode is for you.

    This isn’t motivation.
    It’s confrontation.

    Not the loud kind the quiet kind that makes you sit with yourself a little longer than you planned to.

    This episode captures the moment where I realized legacy isn’t something you explain later it’s something you start building the moment you’re honest about where you are.

    If you’re in the middle of your journey, questioning your next move, or realizing you’ve been playing it safe longer than you should’ve you’ll see yourself in this conversation.

    This isn’t advice from someone ahead of you.
    It’s perspective from someone walking it in real time.

    Chapters

    00:00 Introduction to Legacy Building

    06:09 The Journey of Starting a Podcast

    11:57 The Role of AI in Self-Discovery

    18:13 The Importance of Focus and Delegation

    23:48 Leading with Legacy vs. Playing it Safe

    29:47 The Need for Accountability and Support

    41:55 The Power of Accountability and Feedback

    49:39 Defining Legacy Beyond Material Success

    56:23 Taking Action and Embracing Imperfection

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    1 hr and 2 mins
  • Dear Legacy… | Life After 40 & Building Legacy in Real Time
    Jan 13 2026

    This is Dear Legacy… Episode 0.

    This conversation is about life after 40, purpose, and what it really looks like to build something meaningful when you don’t have all the answers.

    Legacy isn’t just about what you leave behind someday.
    It’s about how you live right now how you show up, how you move through challenges, and how you handle seasons you didn’t plan for.

    In this episode, I talk about:

    • What legacy means to me at this stage of life
    • Why it’s okay to still be figuring things out after 40
    • Entrepreneurship, co-parenting, and blending families
    • Why real conversations matter more than perfect stories

    This show isn’t about pretending to have it all together.
    It’s about being honest about the journey highs, lows, mistakes, and growth.

    Dear Legacy… is an open invitation to build something meaningful in real time, together.

    Why You Should Listen (Episode 0)

    If you’re in a season of life where things look different than you expected but you’re still committed to building something that matters this episode is for you.

    This isn’t a success story told from the finish line.
    It’s a real conversation from the middle of the journey.

    Dear Legacy… is about navigating life, family, business, and purpose without the pressure to have it all figured out. It’s about learning as you go, owning your story, and understanding that legacy isn’t reserved for a select few it’s built by real people, in real time.

    Chapters

    00:00 Defining Legacy and Purpose

    10:10 Navigating Life After 40

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    12 mins
  • Dear Legacy… | Define It. Build It. Live It.
    Jan 13 2026

    Welcome to Dear Legacy…

    This isn’t a highlight reel and it’s not a motivational speech.
    It’s a real conversation about what legacy actually means and who gets to define it.

    I believe legacy isn’t something you leave behind.
    It’s something you’re living right now.

    In this teaser episode, I break down why legacy isn’t a script written by your past, your circumstances, or other people’s expectations. It’s built in real time through the choices you make, how you respond to pressure, and how you carry your name when no one’s watching.

    We talk about:

    • Why you have to define legacy for yourself
    • Why the journey includes the good, the bad, and the uncomfortable
    • How pain can give purpose if you let it
    • Why you are the CEO of your own brand, whether you accept that responsibility or not

    This show is about ownership. About growth. About understanding that character is built in moments that never make the highlight reel but still matter.

    Dear Legacy… is a space to reflect, take accountability, and move with intention.

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    3 mins
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