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Orlando Baeza: “Take the leap”

Leverage resources and service to make up for a lack of technical aptitude. Many people jump to conclusions by thinking they’re not tech-savvy enough to launch their own digital business. They feel overwhelmed by the thought of having to build marketing funnels, recording their first online course and more. Platforms like Kajabi solve for these […]

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Leverage resources and service to make up for a lack of technical aptitude. Many people jump to conclusions by thinking they’re not tech-savvy enough to launch their own digital business. They feel overwhelmed by the thought of having to build marketing funnels, recording their first online course and more. Platforms like Kajabi solve for these ever-prevalent techstack frustrations digital entrepreneurs regularly encounter by dismantling the need for 10+ subscription tools and developers and having to figure out how to make all those tools talk to each other. Kajabi comes in by offering an all-in-one solution and a top-notch, award-winning customer success team to completely eliminate the guesswork associated with these concerns.


As a part of our series about how very accomplished leaders were able to succeed despite experiencing Imposter Syndrome, I had the pleasure of interviewing Orlando Baeza, Chief Marketing Officer at Kajabi.

Orlando Baeza is the CMO of Kajabi, a high-growth SaaS company empowering knowledge entrepreneurs who are serious about their business to achieve success online. Kajabi provides them with a robust all-in-one knowledge commerce platform and all the tools they need to package up their expertise into profitable online courses, coaching platforms, digital communities, and more.

Recognized in both Forbes’ “30 Under 30” and “CMO Next” lists as well as Adweek’s Innovators series, Orlando is obsessed with culture — specifically, how to unlock culture to accelerate business objectives. How can brands authentically elevate subcultures and become trendsetters? Ask Orlando. He’s done it for Nike, Adidas, Paramount Pictures, Activision, and Buzzfeed, where he launched a beauty/style brand with a distinctly diverse and inclusive perspective.

Now at Kajabi, Orlando has his sights on developing a dominant brand in the entrepreneurship space. Kajabi is creating a world where technology is no longer a barrier to building a successful business online.


Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’?

Absolutely. Well, I’m first-generation American and was born in the Bronx, NY. Was the first in my family to graduate from College. Played basketball growing up through high school and in college. Had an unfortunate and severe knee injury which ended my playing days after a couple of reconstruction surgeries and thus, gave birth to my marketing career. I’ve faced adversity and the odds not being necessarily in my favor my whole life, and have always leaned into my work ethic and willingness to outwork everyone around me to continue to progress in my life — both basketball and marketing career alike.

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘take aways’ you learned from that?

A lot of fun stories to choose from here. I’ll start with this. Early in my career, I was coming off a big win and feeling good about myself and celebrating with one of my mentors. And in the middle of the conversation, he asked me about my ambition and whether I was thinking big enough. And he posed the question to me:

“Do you want to be one of the best marketers in sports? Or do you want to be one of the best marketers in the world?”

And that changed the entire trajectory of my career going forward. I set a goal (which I’ve since hit) of working in FIVE completely different industries and in the process, challenging myself to: reset the learning curve repeatedly; understand new consumer archetypes; how to leverage innovative marketing tactics; working with different resource levels; how to tap into dynamically different insights; and overall, become a better marketer, faster.

It’s one of the best things I’ve ever done. I’ve always been driven, passionate, thoughtful and a workhorse. This gave me a direction for my career going forward which has unlocked incredible learnings, opportunities and growth along the way.

Biggest learning of them all — YOUR COMFORT ZONE WILL KILL YOU!

I’ve embraced getting comfortable with the uncomfortable at this point and feel as though it’s in that state where you’re able to get the biggest growth and learnings from.

What do you think makes your company stand out? Can you share a story?

Unlike other online business offerings on the market, Kajabi is a true all-in-one solution and is incredibly user-focused by design to help people turn what they know into what they do. We give our users complete autonomy and empower them with our software and customer support mechanisms to drive their businesses forward and highlight their own brand, allowing them to create content that augments their offline business strategy. We offer subscription-based plans that can scale alongside our users as they start and grow their online business. We don’t take a cut of their revenue because we believe they deserve to keep what they earned and just want to continue doing everything in our power to give them more and more resources to become even more successful.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

There’s so many people to call out here I wouldn’t even know where to start. I say this all the time, but I am very much from the Space Jam School of Learning. Meaning over the years, I’ve (graciously) stolen superpowers from all of the incredible people and leaders I’ve had the great fortune to learn from, work with, and develop relationships with along the way. I am forever grateful for every person who has ever taken the time to share insights, learnings, opportunities, lessons and so much more with me over the years. It’s a big part of the reason I’m here today.

And I spend a lot of my time, energy, and resources focused on paying that forward and impacting the next generation of leaders in any way I can. Hopefully I can have a fraction of the impact on them that so many incredible people have blessed me with over the years.

Ok thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the experience of Impostor Syndrome. How would you define Impostor Syndrome? What do people with Imposter Syndrome feel?

Imposter syndrome is synonymous with the nagging feelings of fraud, not belonging, or not deserving success and accomplishment. Those experiencing imposter syndrome often have an internalized fear that they’ve only succeeded thanks to luck or good timing, not because of their talents and qualifications.

What are the downsides of Impostor Syndrome? How can it limit people?

Imposter syndrome can be such a heavy subject and barrier to success for many people. And since it’s perceived as taboo by many, people dealing with imposter syndrome simply don’t feel comfortable talking about their struggles with it. The biggest downside is feeling isolated and though you don’t have a community to turn to or resources for how to move past it. It can also pigeon hole people into tendencies of extreme perfectionism, constantly undermining their achievements, anxiety, and low self-esteem. And ultimately, the biggest limitation is that it limits your own potential.

How can the experience of Impostor Syndrome impact how one treats others?

One’s experiences with imposter syndrome can inadvertently have an effect on their relationships with others. For example, many try to overcompensate to appear as fully capable or worthy, but such extreme focus can take away from energy that should be channeled into their relationships with colleagues, friends or loved ones. Letting their insecurities get the best of them, can lead to subconsciously imploding those relationships and wreaking even more unnecessary havoc.

We would love to hear your story about your experience with Impostor Syndrome. Would you be able to share that with us?

I’ll give you a recent one. You heard me talk above about how much time I spend on trying to pay it forward and helping other professionals. Well one of the things I hear all the time from people is ‘how did you unlock this amazing career trajectory and growth so fast?’

A couple of years ago, I decided to build out a program that could essentially walk people through a career strategy transformation. Using my own experience as well as many of those ‘space jam benefits’ I mentioned above (shhhh, haha) I built a 5-week program that could transform how you approach your career. I built the content, worksheets, scripts, draft emails, etc., etc. Then I was curious as I’ve helped so many people get promotions and negotiate compensation increases and so on over the years but never had anything this formal, so I questioned to myself — WILL THIS WORK?!

I decided to test it with a small group of less than 10 people who were willing to be part of my experiment and the results were INCREDIBLE!!! Literally every person in that group went on to secure promotions, new job opportunities, compensation increases in a matter of weeks and months, not years. It was astonishing. And even talking to them after the fact touched my heart hearing how much of a transformation and impact they felt. And now I feel a part of their journey forever. They know who they are and I’m always in their corner supporting them.

Back to my imposter syndrome story…so I had this amazingly rewarding experience, and all this content built, and all I was thinking was how can I use this to impact more and more people out there? But that little inner critic just crept in on me and impeded all progress. All I could think was:

Why me? What makes me the authority on this?

Will people trust me enough to purchase this program?

Will they know that my intention in creating this is impact and transformation for those who take it, not generating revenue?

Of all the amazing leaders in the world, does it need another person claiming to have answers?

And for a very long time I did nothing with all of that work despite having those AMAZING results. So it literally affects so many of us.

Did you ever shake the feeling off? If yes, what have you done to mitigate it or eliminate it?

Thankfully, yes. To some degree. And it was recently, partially due to taking over as CMO at Kajabi actually. I wanted to further understand the product. I wanted to walk in our user’s shoes. So I went back to all those notes, worksheets, the content I created and said I’m going to build this all on Kajabi and learn the platform more intimately in the process.

Then with everything built (website, email, content all re-recorded and uploaded, course structure, etc.) I just let it sit there for months.

Re-introducing…that pesky inner critic.

Then I spoke to a friend of mine and executive coach who told me ‘Orlando, how many people are you hurting or holding back by not giving them the opportunity to learn from you directly. You’ve seen the results. You’re being selfish by NOT offering it to people. The people that know you will never question your intentions. Anyone that does simply are not your people. And that’s ok. But think about the people you can help if they have access to this.’

So I launched an MVP of the site at orlandobaeza.co as well as the program using Kajabi. I even made a LinkedIn post about it, haha. I haven’t done any marketing around it or anything (so that inner critic is still having an impact) but there have already been people who jumped in and have already realized the value, felt the impact and started on their transformation. The feedback has just been incredible, and helping people unlock growth in their lives and careers is the most rewarding thing for me personally. So it’s out there and available for those that are serious about putting in the work to transform their career strategy and start taking big steps forward. No magic fairy dust, but anyone who is willing to take the direction and insights and follow the exercises laid out in the program has unlocked incredible results. It’s been amazing to witness.

In your opinion, what are 5 steps that someone who is experiencing Impostor Syndrome can take to move forward despite feeling like an “Impostor”? Please share a story or an example for each.

Give your “inner critic” its own identity. Describe them, name them, and create a separate personality for them. We’ve seen many of our Kajabi Heroes use this approach to separate themselves from their doubts. For example, one user named her “inner critic” Francesca and any time thoughts of self-doubt or sabotage would flood her mind, she’d recognize this as Francesca speaking, not herself. It became easier for her to distinguish between the two and ultimately honor herself while finding the confidence to continue pursuing her goals. This outlook has been so popular among the entrepreneurs we work with at Kajabi that we recently created a new ad campaign born from this concept that highlights how people can get out of their own way. The whole idea is to destigmatize the self-doubt and inadequacy faced by entrepreneurs when launching or growing their own business.

Find your niche. “Why me?” is a question we hear from knowledge entrepreneurs on the daily. They assume that there are more qualified people than themselves to flex their expertise on a given topic and turn it into a profitable business. So why would anyone want to learn from them? To give an example, say someone who’s never played golf before is interested in learning more about the tricks of the trade online. Sure there’s someone like Tiger Woods with all the credibility and success in the world to back his knowledge, but there’s also the local golf instructor who can still help you benefit from their own experiences and insights. Each person has their own unique perspective to offer, and their own way of sharing a certain subject matter with the world. In the end, the power of niche can make all the difference. It becomes a matter of entrepreneurs asking themselves ‘What can I talk about that no one else can talk about in the same way?’

Leverage resources and service to make up for a lack of technical aptitude. Many people jump to conclusions by thinking they’re not tech-savvy enough to launch their own digital business. They feel overwhelmed by the thought of having to build marketing funnels, recording their first online course and more. Platforms like Kajabi solve for these ever-prevalent techstack frustrations digital entrepreneurs regularly encounter by dismantling the need for 10+ subscription tools and developers and having to figure out how to make all those tools talk to each other. Kajabi comes in by offering an all-in-one solution and a top-notch, award-winning customer success team to completely eliminate the guesswork associated with these concerns.

Do your homework and accept trial and error. It’s not uncommon for entrepreneurs to feel like a failure if no one wants to pay a price for their offerings. One way to avoid this mental block is to do a diligent amount of research to determine whether what you have to offer is truly in demand. Once they’ve gotten a lay of the land, they can begin testing to see what resonates. This could include launching with a freebie or mini course to their community as a low-cost experiment to better understand what their audience is most interested in from a content perspective, and evaluating just how much they’d be willing to pay for those resources.

Take the leap. There’s undoubtedly anxiety associated with ‘going live.’ And for many, the fear of stepping out and hitting send for the first time on a marketing email or publishing their website can be all too debilitating. Entrepreneurs simply need to believe in what they have to share and that what they’re offering holds great value. Once that initial launch is out of the way, the anxiety that once prevented them from launching entirely will naturally dissipate.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

Humanity isn’t lost. Think I could convince everyone to be kind to each other and treat them equally and respectfully regardless of gender, race, class and sexual orientation? Or maybe even all agree to acknowledge the fact that unfortunately that isn’t happening today in most cases? Think we could just make a more concerted effort to lift up the people around us instead of sometimes being too focused on ourselves? What if we instead focused on collective good and helping others? Maybe I’m crazy. It’s been a long year.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them 🙂

I’m going to go from a cultural perspective. Jay-Z. Kevin Hart. These guys have taken their talent and transformed themselves and those around them into business empires through strategic decisions, shifting culture, savvy investments, and betting on themselves. To learn from either would be a blessing. To work with either would be one hell of an experience.

Kevin. Hov. Are you reading this? Someone you know reading this? Please connect the dots. But regardless, thank you for the inspiration from afar.

How can our readers follow you on social media?

This was very inspiring. Thank you so much for joining us!

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