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Alex Kowtun of Holiday Swap: 5 Things I Wish Someone Told Me Before I Became a C-Suite Executive

Weekends are for work! Yes, you have to work weekends. Not all weekends but most. Sometimes this only includes some emails and calls; sometimes, this includes skipping a concert you bought tickets for 6 months ago.

As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company” I had the pleasure of interviewing Alex Kowtun.

Alex Kowtun is currently an equity partner and Chief Strategy Officer of Holiday Swap LTD. He is a media & branding expert, Co-Founder of Monkey In Paradise Vodka, Writer, Pilot, Social Media Content Creator, Brand Ambassador, and Media Personality. Kowtun’s social media pages have 1 million+ follower with consistent viral content. Alex was born and raised in Buffalo, NY. He received his Masters’s Degree in Business from St. Bonaventure University and passed the Series 7, 63, and 65 Securities exams before age 21. Kowtun has been a partner in many companies in the financial sector and relocated to West Palm Beach, Florida. Since moving to Florida, he created and founded Monkey In Paradise Vodka with two close friends. Throughout these exciting entrepreneurial adventures, Kowtun grew his personal brand on Facebook and Instagram. Alex is a frequent guest on ABC and NBC news affiliates, discussing business, aviation, and upcoming charity events. He has also been featured in Flying Magazine, Daily News, Palm Beacher Magazine, West Palm Beach Magazine, Yahoo Finance, Buzz Feed, Palm Beach Daily News, The Street, and Palms West. For fun, Alex is an avid pilot, races car, and boats, and shows the people around him amazing social experiences. He is always getting people off their mobile devices, pushing for that more entertaining lifestyle, and motivating them to make the most of life.

Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

With a middle-class upbringing, in Buffalo, NY, I always wanted more. I had a passion for airplanes, boats, and fast cars. But never had access to them. I started my first business in high school selling car audio components, a car company in college, financial services companies after, then a successful national vodka brand. I exited the vodka brand and took an equity position in Holiday Swap, LTD, along with a C level position.

Can you share the most interesting story that happened to you since you started your career?

While building my personal brand and ultimately becoming the Chief Strategy Officer at Holiday Swap LTD, I created a successful vodka company. It went from my condo living room to a national brand. After exiting, I took an equity position in Holiday Swap. Holiday Swap is a fast-growing international business. Without developing my personal brand and exiting the vodka company, I would not have had the massive opportunity to be a part of the Holiday Swap, C- level team.

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

The boos usually come from the cheap seats”. Never let those who doubt your business or skill sets get in the way. There will always be people that enjoy being negative rather than positive. Remember, the boos NEVER come from the playing field.

Is there a particular book that made a significant impact on your leadership style? Can you share a story or an example of that?

The book that motivated and inspired me is actually not a business book. The book is A Brief History of Time by Steven Hawkings. This was a hard read due to the complexity of astrophysics subject matter. But the book taught me how massive the universe is. How everything we do is so small. It showed how much more we can achieve. How much bigger we can be. How confused most people are about our minute relevance. We have so much more to learn and achieve.

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

Holiday Swap Founder, James Asquith, is the most frequent traveler in the world. He has in the Guinness book of world records for being the youngest person to travel to all 196 countries. During these adventures, he wanted others to be able to do the same. But he saw the extremely high price of travel. While traveling, he had the brilliant idea of leveraging the place you live and sharing it with others when you are not there. In essence, a way to have travel accommodations become almost free. He launched Holiday Swap in 2018, and now even renters can swap their place with others or earn tokens to host people and then travel using the tokens. No Holiday Swap users list their homes and make them available in over 180 countries. Holiday Swap is quickly becoming the #1 travel app and opening up travel to those that may not have been able to afford it in the past.

The road to success is hard and requires tremendous dedication. This question is obviously a big one, but what advice would you give to a young person who aspires to follow in your footsteps and emulate your success?

Always have massive ambitions. Put the hard work in. Nothing comes easy. Most importantly, always surround yourself with other successful people and learn from them.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

The advice I once received was to hire people with more experience than you for important roles in your business. I did this in one of my businesses for a top leadership position. The hire was so out of touch with marketing, leadership, and management. This one decision nearly ruined the business and stunted its growth for a very long time. It is not the amount of experience that matters.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Loyalty. It takes massive loyalty for success. Somebody that doesn’t do the right thing when nobody is looking is rarely successful. By being loyal to those around me, I was able to partner with 2 of my best friends to start my last business. This happened at a time when I was not in a position to put up the capital for the venture.

Dedication. 9 to 5 does not cut it for success. I work 7 days a week, as do all other successful leaders and entrepreneurs that I know. While building my liquor brand, the founder of Holiday Swap witnessed my massive dedication to the company for 4 years. When it came to selling, he offered me an opportunity to take an equity position and join the C Suit team. This is now the opportunity of a lifetime to run a large international company and take it public in the coming years.

Charisma — It takes charisma for success. Charisma will allow you to meet and be friends with the right people that can help in life and business. Most people I have done business with or worked with came from introductions and becoming friends first. This was the case with every business I have ever started or been a part of.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a C-Suite executive does. But in just a few words, can you explain what a C-Level executive does that is different from the responsibilities of other leaders?

Shit flows uphill, not downhill, in a large company. The C-Level team is responsible for every detail of the company. Guess who is responsible if something doesn’t get done at any level? The C-Level team. The big misconception is the glamour of a C-Level role. When things go wrong, it is the C-Level on the hook. They are the ones that have to work 7 days a week and 16 hours a day when there are problems. The C-Level is responsible for all wins and losses for the company.

What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?

I think the biggest myth is massive unjustified salaries. In a public company? Sure. But in a startup or even mid-sized company, C-Level pay per hour is a fraction of what most think. The most successful C Level teams work for massive equity options and performance incentives.

What are the most common leadership mistakes you have seen C-Suite leaders make when they start leading a new team? What can be done to avoid those errors?

The biggest error I have seen is hiring out of desperation. Finding C-Suite leaders should be planned in advance. Far too often, a company decides to quickly get rid of somebody and does not have a replacement lined up. This is when the replacement is out of desperation and not of qualification,

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

The most underestimated aspect of running a company is accepting the industry norm. A great example of this is the user acquisition strategy for Holiday Swap Group. Industry average pricing for acquiring users in the travel industry is between $3 — $6. Our marketing team consists of experts in social media and digital marketing. Instead of accepting industry-average user acquisition costs, we work hard to push out-of-the-box campaigns with results that are a fraction of the industry average. Never accept the industry norm as success.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading From the C-Suite”? Please share a story or an example for each.

  1. The early stage pay usually sucks! As I mentioned earlier, C-Suite positions don’t typically come with 7 figure salaries initially. But they do allow for it with proper alignment of success for the company with performance bonuses.
  2. Weekends are for work! Yes, you have to work weekends. Not all weekends but most. Sometimes this only includes some emails and calls; sometimes, this includes skipping a concert you bought tickets for 6 months ago.
  3. Get ready to rely on people and take accountability for them. The C Suite is responsible for everything and everybody. Get ready for it. It never ends.
  4. The Travel Will be Fun! Who doesn’t love to travel? C Level travel usually includes staying at mediocre hotels, flying coach, and never staying in the same city for over 48 hours. I remember when I traveled 80% of the days for 2.5 years straight. It got so mentally difficult; it was hard to remember which way the elevator was while walking out the hotel door. The travel is tolling and loses the glitz and glam. There truly is no place like home after intense business travel.
  5. Vacations? Probably Not. As a C Suite member, extended periods of time off will not be likely. I remember sitting in a hotel in Daytona Beach on my birthday, which is also Valentine’s Day.

In your opinion, what are a few ways that executives can help to create a fantastic work culture? Can you share a story or an example?

If you are going to commit to taking an executive role and the massive commitment that comes along with it, make sure you like the people you work with. There is nothing worse than spending most of your time awake dealing with people you do not like. I remember making a terrible hire for my C Level team where I overvalued somebody’s experience rather than character. It was my single biggest mistake ever in business. Liking the people, you spend the most time with will naturally create a fantastic work culture.

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

Political correctness and the weakness of modern-day society are the single most dangerous thing I have seen in my lifetime. I work hard to preach being strong, making massive commitments, and achieving unprecedented results. Success is not for the weak or sensitive. I will continue to lead like this by example and share it with the success of companies I align with. Now it’s your turn. Toughen up. Nobody cares about what you are offended by.

How can our readers further follow you online?

Download the Holiday Swap, a travel accommodation app. It will change the way you travel, saving an average of 80% on travel accommodations around the world.

Instagram: Business — @holidayswap

Personal — @successful, @alexthepilot1, @aviationdaily

Tiktok: Business — @holidayswap

Personal — @alexkowtun

Website: Business:


Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!



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Yitzi Weiner

Yitzi Weiner


A “Positive” Influencer, Founder & Editor of Authority Magazine, CEO of Thought Leader Incubator