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24 Oct

Ep. 122 – Olenka Cullinan – Founder of Rising Tycoons and #iStartFirst, Author

“When they’re in kindergarten, they’re being prepared for first grade. When they’re first grade, they’re getting prepared for high school. When they’re in high school, they’re being prepared for college. When they’re in college, we’re getting them prepared for their first job, and then it’s first car, and first house. So we’re always being prepared for something. And in the middle of all that, we lose the journey.”

Olenka Cullinan – Founder of Rising Tycoons and #iStartFirst, Author; Teaching kids about failure and risk; Practicing worthiness 

Segment 1: (Length :04:00) – General Updates; Introduction to Olenka Cullinan and her journey as an entrepreneur; Starting Rising Tycoons; Teaching kids about the journey. #iStartFirst movement

Olenka’s finer points:

“I borrowed $450 from my uncle, jumped on the plane, and moved to this country, building my own American dream.”

“My mom cried. But I also grew up with a mother who was a CEO of a company for 37 years, so my goal is … At the beginning, I was like … I thought every teen lived like that: all of them got to go and see their mother work 80 hours a week; all of them got to meet CEOs and negotiate million-dollar deals when they were 14, 15 years old.”

I would travel with her all over Europe, walk into rooms full of men in suits, and negotiate million-dollar deals. So I thought everybody lived like that.

“So when I moved here on my own and kind of started from scratch, I realized … I ended up teaching, because I wanted to get away from entrepreneurship as far as possible, which is really funny.”

“My brother did the same thing, but my goal was to see … I guess I needed to see that, because when I went into education, I somehow forgot that we teach them academia. You know, teach them math and science skills, but we don’t teach them real-life skills.”

“And I was privileged enough to teach all across the board. I taught university level, community-college level, and high school, and saw that all these kids were always … youth, I guess, were struggling with the same issue: they didn’t know what they were passionate about.”

They didn't know how do you think about success, what success is. Most of them think it's a magical unicorn and you have to be born into a family of Rockafellers. Steve Jobs started his company in a garage, and he was a billionaire the next day.

“So I saw all these gaps in their education, and I wanted to create Rising Tycoons, a company that would bring real-life experience, would bring entrepreneurs just like you and Case on board, to show them that success is hustle. But it’s also flow.”

“It’s also the ability to understand how all these skills come together. And hence my favorite quote: Skills are learnable; success is learnable, too. All success is just a combination of skills they have to learn.”

“to me, everybody has circumstances. Everybody’s born into something; everybody has some kind of family; everybody has their own struggles. And the reality of things is: if we don’t look at this as opportunities, then we will forever will be running from our life. And when you run from yourself, you know you can’t run very far.”

“So that’s the whole reason I embrace that methodology and we teach that all you have is your circumstances, and all you do is turn them into opportunities. You essentially have two things, right? Excuses or opportunities.”

So the second they see all these struggles as opportunities, they have ability to build on that, develop their strengths, and find out how they can do better and be better. Because so many people are caught up in this future vision.

“We are all great at talking and dreaming big, and, you know, 30,000-foot view, and I’m a big fan of that too. But it’s your unsexy routines that happen day by day that will change your life forever. And I will say that till the day I die.”

“I’m super-impatient. I’m learning, and definitely learned with entrepreneurship and by hanging out with you, Matt, definitely learning to stay in the lane, stay the course, remember why you’re doing all these things. But yes, with teens, obviously, we live in a “everything-was-supposed-to-happen-yesterday” society.”

It's instant gratification. These kids are microwave-born-and-raised. They want everything in 30 seconds, and it better be incredible.

“So one of the things that’s so important with youth, and the whole “I Start” movement, to be honest, started by me working with a lot of adults and clients and universities, because this whole mentality of “unless you’re number one, you better not play”: well, you can never be number one if you’re not on the court. So that’s just the truth of that.”

“When they’re in kindergarten, they’re being prepared for first grade. When they’re first grade, they’re getting prepared for high school. When they’re in high school, they’re being prepared for college. When they’re in college, we’re getting them prepared for their first job, and then it’s first car, and first house. So we’re always being prepared for something. And in the middle of all that, we lose the journey.”

“We’re literally so training them to just go for destination that they never enjoy the journey and the process. They never learn what it’s like to just start and go for those motions of understanding who they are.”

Segment 2: (Length :08:00) – Talking with Olenka Cullinan; Teaching kids about failure and risk; Removing parents from the equation.

Olenka’s finer points:

“If you truly admire somebody, first of all, those are not the people who are going to put their mansion on the Instagram 10 days after they started the company. That’s just not how it works. And If you truly go to people who are incredible and ask them questions on how they started, they’ll walk you through that process. So I’m a huge, huge supporter, believer, preacher for mentorship.”

“And then my other thing: I always tell people, “I need you to only, only, your whole life, compete against one person: the person that’s in the mirror.” If you start measuring your own results, and depending how you were yesterday versus how you are today versus how you are a month from now, that’s what’s going to propel you.”

“I actually have an accountability partner I do a call with every single week on my personal goals. No matter what: rain, shine, ugly, whether she’s in another country, or I am somewhere else, we get on the call for 45 minutes every single week and go over our personal goals and what we got done, or not. It’s personal. It’s all about you.”

we don't start them on the risks right away, so we build their mindset first. We're big fans, and I am a big fan, of mindset, obviously. So yes, first we're teaching them about understanding that anything in your brain, you're in control of, because a lot of times they come in, and their mindset is sort of in the toilet, which is pretty typical of teens.

“They don’t live in the best, most positive environment, let’s be honest. Our high schools are not all rainbows and unicorns. In case you haven’t been in one, I highly recommend that: puts your self-esteem in check within like 3.5 seconds.”

“And then, in terms of risk, what we do, we … It’s all … gamifying it a little bit, of course, but also my big … I’m a big fan, like I said, of real-life experiences, so we expose them to a lot of entrepreneurs who’ve gone through risk, who’ve failed some.”

“We actually do Failure Awards. We don’t celebrate it, but we respect it. We teach them that failure, you’ve got to respect it. It’s just a step to success; it’s not something you should avoid. Our society in general teaches people to avoid failure at all costs. But it’s reality … The psychology behind it, you know it has nothing to do with failure. It has everything to do with fear. You are scared of people judging you. You’re not afraid of them; you’re just straight-up scared, but nobody will admit that.”

“I’m also a huge fan of “Lean Startup.” We actually teach that methodology to our teens as well. What we teach them is: one, don’t fall in love with “awesome.” As entrepreneurs, we tend to love every idea we birth, because it’s our babies. So we teach them early on: “That’s just an idea. And you are brilliant and magical, and you have ideas galore.”

“And if you’re going to fail, do it today, when you’re still in high school, versus doing it when you’re 30 and invested way more money. And now, you can mooch off your parents and run your company out of your parents’ garage, and use their cell phones.”

“So yeah, we definitely teach them how to learn and adapt to the situations they’re in. We absolutely, 100% teach them that they’re young, and they should use that going to businesses and potential sponsors. And they’re actually learning, so we make them very humble in that approach.”

You pivot because you learn that you can fail quickly, but you also pivot because you learn from so many other smart adults around you, and you should just enjoy the journey.

“Parents are much worse. I’m just going to be honest. I’ve done tons of trainings. I mean, lucky for us, we’ve been doing tons of trainings with adult influences in general.”

“first of all, we ask our parents to sign an agreement to not ask their kids any questions about the program. So we come out straight out of the gate saying, “This is how it’s going to be. We need them to unlearn everything, and adopt a completely different mindset. We also need them to give up your passions and interests, and find their own.”

“At this point, we’re getting a lot more support, and parents have always been our biggest fans. But yes, have we had some issues with parents, especially at the beginning? 100%. Because normally they walk into the room, and it’s their child. And I’m very respectful of that fact, but I’m also very mindful of the idea that unless you let go, unless you let them sort of get out from underneath your wing, they will always be living your life part-time.”

“And my goal is to teach them how to live their own life, and be connoisseurs of their own lives.”

So Rising Tycoons is my baby. I started with that first. Never really planned it, which is actually interesting, because I was just planning to be a youth speaker and get youth excited about the possibility of building their life in whatever they wanted it to be. But everybody kept asking for more, you know, they get fired up, and then what

“And so we built the program called “Rising Tycoons Academy,” which we just now launched digitally. The goal is to beta-test 1,000 students, because we want to see … We’ve been running this program on the ground for about three-and-a-half years, tested it with kids from 22 countries, so we’re 100% sure that our content is key.”

“And it works, regardless of their socioeconomic status; it works regardless of their culture or background or country they live in.”

And then also another part is my adult work, which is through olenkacullinnan.com, where I coach clients on the same approach: up-leveling your mindset, your business, and starting first.

Segment 3: (Length :10:00) – Dealing with failures; The false stories we tell ourselves; Being self-centered means putting yourself at center; Practicing worthiness; Watch the stories you tell yourself.

Olenka’s finer points: 

“I don’t teach anything I don’t do, whether it’s to teens or adults. So if I haven’t done it, if I haven’t worked with this person, if I haven’t experienced something: I won’t teach it.”

“I’m a big fan of full-on transparency. I share my own failures all the time. My teens go pretty much like …Whenever I work with youth or adults, even clients, I want them to realize that I’m human. I think too many of the coaches and gurus present only one side of this story: that “10 years overnight success,” as Matt called it earlier.”

So I'm not a fan of that. I'm a fan of authenticity. To me, authenticity trumps everything, especially if you work with youth. They read through you like nobody's business. These kids can read between the lines faster than anybody I know. So it would never work for me to build the company that I've built if I was not authentic in my approach.

“What has come to me is the fact that yes, I’ve met incredible people. Meeting Darren Hardy and being mentored by him: that gave me a huge sense of credibility. But also the fact that I was invited to TED talk.”

“But in terms of people listening to a lot of noise: I get caught up in the noise sometimes too. And it’s going back to that authenticity. Do these people, do these gurus, do these coaches … are they authentically aligned with your purpose and your vision?”

“I’m telling you right now: I’ve had people approach me to do business together, I’ve also had people approach to mentor me or coach. If we don’t align authentically … just like what Matt was talking earlier, that you guys even make sure your sponsors are aligned with podcast vision … If I don’t align with these people, it doesn’t matter to me how much money they make.”

I need to see that that human potential and that human spirit is there first, and then everything else comes second. And I give that advice to the youth and all my clients: find people who align with you first.

“It’s ego/fear combo, because yes, getting in front of people and admitting some of your mistakes and issues takes a huge amount of courage and balls, for the lack of a better term.”

“Vulnerability is a hard, hard lesson for a lot of people. They shy away from being vulnerable as much and as far as they possibly can. So to me, that’s one of the most masterful qualities one can attain is that vulnerability, and being open and transparent.”

“But I also think most … Not most, a lot of people are so, so hung up on spotlight that they forget about impact. And I always say it should be backwards. It’s not about spotlight; it’s about impact.”

Because here's the reality of things, and that's for any young entrepreneurs, creators, hustlers out there: if you create enough impact, you will get your spotlight. I guarantee you. You will have your thousand true fans and people who will believe and stand behind you, no matter what.

“But if you start doing it the other way around, where you’re just so worried about spotlight, you will have an inauthentic audience that will never support you, that will never propel you to the destination you want to be.”

“Segment 4(Length :03:00) – Hustler Thought of the Day:

Stop preparing. Start doing. – Olenka Cullinan


Olenka Cullinan – Founder of Rising Tycoons and #iStartFirst, Author

Olenka has developed a “Backbone of Success”™ method that helps leaders to up-level their business and mindset. With Rising Tycoons, she helps teens become successful in school, life and the world combining leadership, entrepreneurship and personal development. Turning teens into mindful tycoons.

Having been trained by the top achievers such as John Maxwell, and Darren Hardy, Olenka strongly believes that the pursuit of success with happiness is what creates goals, vision, and destination for the teens.

Her work as a startup venture mentor nationwide, combined with humor and personal experiences led to her two TEDx talks, Phoenix Business Journal 40Under40, global exposure and made her into one of the nation’s premier consultants.

Having moved to the US with $450 in her pocket, Olenka has lived through about every “I-can-never-be-successful-because” excuse a human can make.

She teaches youth and adult influencers to stop preparing for the perfect moment and start doing instead.
Olenka has co-authored a best-selling book, Passionistas: Tips, Tales and Tweetables From Women Pursuing Their Dreams with incredible #girlbosses, including CEO’s, founders, influencers, entertainment giants, and more sharing their authentic stories.
Check out Olenka’s site HERE |  Social for Olenka: Instagram | Twitter

Episode Sponsored by:



Matt Gottesman

Matt Gottesman is a global digital strategist and technology advisor, creator and editor-in-chief of Hustle & Deal Flow™ - an online magazine dedicated to the world's entrepreneurs, creators and makers, a Social Media Influencer and a consultant on New Media and go-to-market strategies for investments in digital marketing, technology, websites, mobile applications, eCommerce, social media and content.