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Rise to Lead Podcast episode 88. Where Winning Gets Human with Richard Blank

Lead & live differently. This podcast is for entrepreneurs and leaders who want real freedom, a life that feels like it's theirs, and a team that thrives — without sacrificing themselves in the process. Get practical strategies on modern leadership, authentic influence, and how to build the life, business, and career that’s actually right for you.
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RISE TO LEAD
Fearless Voices, Bold Leadership, Unconventional Thinking
Welcome to the hub of leadership inspiration with Regina Huber. Tune in for candid conversations and invaluable wisdom from bold leaders across industries and cultures.
RISE TO LEAD is where fearless voices and unconventional minds share how they shape movements, businesses, teams—and themselves. This show celebrates creative leadership in all forms, from the stage to the boardroom, from community spaces to solo ventures. We explore creative, sometimes unexpected expressions of leadership—from business innovators and band leaders to movement makers. Come for bold heart, audacious action, and the kind of leadership that creates greater freedom for you and those you get to impact.

What happens when you stop following the expected path—and trust what pulls you instead? Richard shares how a short trip to Costa Rica turned into a 25-year entrepreneurial path, built from the ground up by leaning into instinct, language, and real human connection. This conversation goes beyond business—it’s about stepping out of comfort, creating something that reflects who you are, and leading in a way that people actually feel.
We explore what makes people stay (even in high-pressure environments), how to turn transactional conversations into meaningful ones, and why the real advantage today has nothing to do with technology. From conversational intelligence to creating spaces where people can breathe, grow, and perform—this episode challenges how you think about leadership, communication, and what truly lasts. AI will never be able to replace this.

Ready to Lead in a Bold New Way AND Enjoy Greater Success and Fulfillment Through It? –
Let’s amplify your leadership, fully aligned with who you are. Master communication, ignite team engagement, and achieve breakthroughs with my exclusive formula for Thriving Leaders ready to break the mold, embrace new paradigms for themselves and their teams, and find true fulfillment


https://youtu.be/LmAoEOOzQz0
Transcript
00:00Or as you did in Argentina and I did in Costa Rica, you just leave everything.
00:03You start from scratch and you see if you could build something.
00:06Oh my God, it's so much sweeter.
00:09It's so much better.
00:11It's so organic.
00:11It was made from magic.
00:14And I think that that's when money doesn't even matter at that stage.
00:21You're looking at someone's courage and what they're willing to do.
00:26As John Wayne says, Regina, die with your boots on.
00:30Hey, kiddo, you were willing to go for it.
00:32In fact, I would have loved to have done an Airbnb or bed and breakfast compared to a call center.
00:37It sounds like so much more fun.
00:40And you did it right.
00:42You did it your way.
00:44And so you said it earlier.
00:45We got a lot of things in common.
00:46Yes, we do.
00:47We were two dreamers that realized that life is a gift and you sometimes need to walk alone.
00:58And it's okay if someone thinks differently.
01:00It's just their own.
01:01As you said, they're not willing to have that breakthrough where they're willing.
01:06You even said, you said one of the deepest things,
01:08Alberta, just willing to find themselves.
01:11And that's not for you and I to do.
01:13We can't get that out of them.
01:15All we can do is show them that we found the way in our own wiggle way.
01:21We wiggled.
01:22We found our way.
01:24I don't know how, but we did it.
01:30There's no book for it.
01:31And you know that, Regina.
01:32We can give a thousand bits of advice.
01:34All I'm asking you to do is to move left and move right if there's something in your way.
01:38That's all I'm asking you to do.
01:40And pace it at your own speed.
01:43And smile while doing it.
01:45It's almost like the tarot fool card.
01:47You're allowed to smile while walking off a cliff.
01:49You should enjoy life like that.
01:50Every day is your last.
01:51And so I kind of looked at it like that as well.
01:54That's my go-go juice to keep me going.
01:57Okay.
01:58Wow.
01:59Yeah.
02:00It's really a beautiful way of saying this.
02:05So talking about smiling, though, I don't know.
02:09Maybe you always smile, Richard, but maybe not.
02:12So when you're not at your best, what's your personal reset to get back into your smiley alignment as a
02:21leader?
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