Meet Alex Robaina | Founder + CEO of LISTA Planning Co.

We had the good fortune of connecting with Alex Robaina and we’ve shared our conversation below.

Hi Alex, can you walk us through the thought-process of starting your business?
I started university in 2013 without the faintest idea of what I wanted to be when I grew up. I met with a guidance counselor who recommended that I pursue a career in medicine, based on my excellent grades in anatomy and chemistry, whether that be pre-med or nursing. When I weighed both options, I prioritized finishing school quicker. I thought, “I want to start my life already”, so I chose the shorter track: nursing. I got into one of the most competitive nursing schools in the country, and once I started taking the classes, I realized how much I actually lit up at the idea of helping people in a vulnerable state. I graduated and obtained my license, extremely proud of my title as Registered Nurse. Then, throughout my 6 years of working as a nurse in local hospitals, clinics, and even remotely, I realized things weren’t what I had hoped for. I still loved the work I was doing, helping others feel safe and heard, giving them concrete support in their healthcare journey, and guiding them through some of the toughest moments in their lives. But I kept running into a similar problem – I couldn’t always help them the way I wanted to help them. In some positions, it was that I couldn’t be fully present with a particular patient because I was assigned too many patients and had to split my limited time with all of them. Sometimes it was that I had to miss multiple opportunities to spend time with family around the holidays, or leave loved ones with fear in the middle of a natural disaster. In other instances, my priorities for a more satisifed and holistic customer experience didn’t align with the priorities of the company for a higher volume or revenue. None of these things are inherently bad, but they are all situations I found myself in that didn’t align with my values or the vision I had for my life. I looked inwardly to find the answers for how I could serve others in a way that didn’t make me have to sacrifice time with loved ones or my personal beliefs. I found that I’m highly motivated by personal achievement, and I thrive when others feel good as a direct correlation of something I did. Entrepreneurship seemed like the only right answer. I thought about what the people in my life usually come to me for and realized I’ve never been able to pass up an opportunity to plan an hour-by-hour itinerary for a friends’ trip, or volunteer to host any upcoming holiday party or celebratory dinner. Spending hours making checklists and spreadsheets, DIYing decorations, and researching the best bars in X destination not only excites me, but also comes seamlessly to me while the mere thought of it gives others a massive headache. When the opportunity came for me to leave my career as an RN and pursue something of my own, I jumped, knowing that for every type-B friend I have that benefits from my perfectionistic tendencies, there must be a million more that don’t have an incredibly type-A person in their lives to take care of the details for them. That’s where LISTA Planning Co. comes in.

What should our readers know about your business?
LISTA is a full-service, concierge travel and event-planning company (both in-person and remotely). We seek to help busy and organizationally-challenged individuals prioritize what matters most to them, while encouraging more celebration and exploration without the stress or hassle of planning for it. What sets us apart is our empathy and our experience working in both travel and event-planning. In today’s world, it’s becoming increasingly more common to celebrate milestones and events with loved ones away from home, with a weekend-long birthday trip amongst friends or a week-long family reunion over the festive season. The two used to be separate more often than not: you’d either have a birthday party or you’d go away for your birthday with your partner, for example. Now, we’re seeing the likes of what it takes to plan a destination wedding, but for birthdays, anniversaries, and bachelor/bachelorette parties. I think since COVID, people will take any reason to get-together and celebrate or explore a new destination with as many people as possible, because the time spent apart made us realize how much of life we still have yet to live. I get most excited when I see my client’s initial reaction to their dream trip itinerary or party checklist completed. They’re usually shocked with the amount of work that’s already done for them, and the relief on their faces when they see they can actually sit back and relax is palpable and so worth it.

It hasn’t been easy building this business at all, and there are still a lot of kinks that need to be worked out. I joke that I’m the worst boss I’ve ever had, because I know I’m working harder than I ever have, working through lunch, sometimes not taking any rest days during the week – but I’m also the happiest I’ve ever been working for myself and for the clients that choose to trust me with their special moments.

So far, I’ve learned that mostly everyone in your life will think you’re crazy for not sticking with the status quo, until it works, then you’re not so crazy anymore. I’ve also learned that with an unhealthy, scarce, or fearful mindset, the work will be three times as hard and your results will be directly impacted.

I want the world to know that I care, and that I will always be in their corner. If I had one client that walked away from our services feeling understood, cared for, and like they just worked with a friend, I’d be happy.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
If I were showing someone around for the first time, I’d start with a day exploring classic Miami. We’d have pastelitos and cafecito at Versailles for breakfast, followed by a walk in Little Havana to see Domino Park and get a taste for Miami’s culture and my Cuban roots. Then we’d hit Wynwood for lunch and a drink at 1-800 Lucky or Coyo Taco followed by a walk around the Wynwood Walls, and dessert at Salty Donut. In South Beach, I’d take them to see South Pointe Park around sunset, where we could watch the cruise ships leave port, but if they wanted a beach day, we’re going north towards Fort Lauderdale where it’s a little more chill. Happy hour is at Rosa Sky one night, overlooking the beautiful Brickell skyline. For dinner we’re coming back to my hood in Kendall for Tacos & Tattoos or further west for Finka, followed by more cafecito and croquetas at Islas Canarias. For a party, I’m taking them to E11even. This is just scratching the surface, honestly. I love my city!

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
Two come to mind immediately. The first is God, without whom I could accomplish nothing. All the glory goes to Him, and I fully believe His timing is perfect and His plans for me are better than I could ever dream up for myself. Second is my incredibly supportive husband, who would sacrifice his own wants for my happiness (even though I fight him on it). Without his unwavering support and willingness to be the sole provider for our family at the beginning stages of our business, there’s absolutely no way I would have been able to go after my passions. His belief in me has held me together on so many days when I couldn’t believe in myself. He is my rock!

Website: https://listaplanning.co

Instagram: @listaplanningco

Facebook: https://www.facebook.com/profile.php?id=61557628433181

Image Credits
Ninette Iglesias