I’ve found that breaking an idea down into bite-sized and prioritized chunks really helps me to get things done — and fast. Even just checking off one or two tasks a day helps me to build, and sustain, momentum.”
Alex is the founder and CEO of Upgraded Points, a website that offers insider strategies for travelers to maximize their credit card points, miles, and rewards in order to enhance their travel experiences. He has been traveling for more than 25 years, thanks to his parents, who started taking him along on trips when he was young.
Alex studied business, management, and Spanish at university. After graduating, he traveled with five friends to 10 countries in a month on a barebones budget. The travel bug metamorphosed into an obsession when Alex moved from England to the United States to be with his now-wife, Erin. Since then, he has earned millions of travel miles and points through maximizing the bonuses he earns through credit card sign-ups and the points he earns on each dollar he spends.
These strategies have allowed Alex to fly on some of the most celebrated first-class airlines in the world. Alex finds the most rewarding part of running Upgraded Points to be hearing stories from readers about their own successful travel exploits.
Where did the idea for your company come from?
In December 2011, I moved from England, where I was born, to the United States. I checked in for my flight from the London Heathrow Airport at the British Airways counter, only to be told that my flight was overbooked. Luckily, because I was a member of the airline’s loyalty program, I was upgraded to business class for my flight. I was over the moon with excitement. I enjoyed a 10-hour flight to St. Louis sipping Champagne, eating delicious food, and watching movies. It was the perfect way to begin my new adventure.
I couldn’t stop thinking about how I could make that happen again — without paying a dime. That’s when I became obsessed with points and miles. A few years later, when I saw a big gap in the market, I jumped at the chance to make a change. I wanted to create a space where people could have access to extensive guides and up-to-date information that would make using points feel accessible and understandable.
What does your typical day look like, and how do you make it productive?
I start my day around 7 a.m., and I make a point to not reach for my phone or laptop right away. First, I take some time to make myself a cup of coffee and quietly reflect on my day. Those first 10 to 15 minutes are crucial in order to set myself up for success for the rest of the day. I know that if I start out my day looking at a screen, I always feel frazzled later on.
I’ll work from home for a few hours before I hit the gym mid-morning. My morning commute is a 10-minute walk into downtown Austin, and I’ll stay at my office until 6 or 7 p.m. before strolling home. My time walking to and from the office is an essential and cherished part of my day that gives me time to decompress. Those minutes allow me to be a more present partner when I walk through the door to my incredible wife and adorable puppy.
I maximize my productivity during the day with my treadmill desk that houses two monitors — allowing me to do double the work. My office space is quite open, which helps me to stay focused on generating ideas and solutions.
I’m a health and fitness fanatic, and I prefer to fast until lunch. Typically, I try to follow a low-carb diet because it helps me to stay energized and alert throughout the day. In the afternoon, I usually need an energy boost, in which case I make sure to take a break, sip some hot tea, or nibble on some dark chocolate. In the evening, I enjoy eating dinner at home, and maybe even watching a TV show, but I do end up opening my laptop again to wrap up some more work. I finish my day reading some fiction before bed and making lists of my big wins for the day and what I hope to accomplish for tomorrow. This way, I know that I am set up for success for the next morning.
How do you bring ideas to life?
I am unbelievably impatient, which just motivates me to put my ideas into action. I have to be incredibly excited about an idea to justify spending time on it, which actually serves as my internal filter in helping me to select what I do pursue.
I’ve found that breaking an idea down into bite-sized and prioritized chunks really helps me to get things done — and fast. Even just checking off one or two tasks a day helps me to build, and sustain, momentum.
While it’s very important to remind myself of my end goal, it can be dangerous to just focus on that. For me, breaking down that goal into smaller chunks keeps me moving forward and building up lots of wins.
What’s one trend that really excites you?
I’m fascinated to see how travel will change over the next 10 years. Because of the expansion of technology, I am curious to see what apps and gadgets travelers will be using. What will airports look like? How stressful will the traveling experience feel? What new amenities will be offered?
There is already a movement in place for airports to become similar to shopping and entertainment centers. This social focus might mean that a boarding pass won’t be necessary to enter an airport. I’m also excited to see what perks airlines continue to offer and develop for luxury travel.
What is one habit of yours that makes you more productive as an entrepreneur?
I know that no amount of motivation matters if I don’t make time for exercise. It is essential for me to exercise regularly. Most mornings, I’m at they gym doing a high-intensity workout that pushes me to my limit. It is my equivalent of hitting a mental reset button, and leaves me feeling totally refreshed and buzzing with ideas afterward. Without this, I know that my productivity would easily be cut in half.
What advice would you give your younger self?
Don’t worry so much! So many of my worries and concerns never even became an issue. It wasn’t worth all the heartache and stress. It’s important to be aware of potential issues and problems, but it’s also important to spend time enjoying each day and being around people who make you happy.
Tell us something that’s true that almost no one agrees with you on.
I add cream into my coffee mug first before adding the coffee. I think that it results in a liquid that is lighter in color — and just more enjoyable to drink. My wife thinks that I’m crazy!
As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?
Before I go to bed, I write down everything that I have achieved for the day — regardless of how big or small the accomplishment. As an entrepreneur, I am obsessed with developing and reaching my next big idea or goal. It’s important to remind myself of how much I have accomplished in a day in order to stay focused on my bigger-picture goals. These daily wins keep me motivated and keep me heading in the right direction — one step closer to my goals.
What is one strategy that has helped you grow your business?
It’s important for me to provide value first, before I think of selling anything to anyone. In a world full of advertisements and noise, it’s possible to stand out by helping people solve a problem before selling a product or service. This makes it a lot easier to create a positive relationship from the start and makes selling a product or service a lot easier down the road.
What is one failure you had as an entrepreneur, and how did you overcome it?
I once made the mistake of cutting costs at a critical moment. I signed an agreement with a company to engage with them that checked all the boxes. The meetings went well, and they were responsive and eager to provide their service. But we opted to read through the agreement ourselves instead of hiring an attorney in an effort to save money and time. That ultimately cost us far more money than an attorney — and a massive amount of stress. We had to hire an attorney after the fact, which did help to stop further financial and emotional losses. Ever since then, we have run every agreement by an attorney. It’s just not worth it to save a few days and a small amount of money for the corresponding risks.
What is the best $100 you recently spent? What and why?
A wide-angle lens for my iPhone. It was super easy to attach, and it allows me to take much better photos for my social media — especially in-flight.
What software and web services do you use? What do you love about them?
• Mention.com tracks all mentions of your brand online and makes it effortless to manage and track your reputation.
• Ahrefs.com and SEMrush.com are an SEO’s dream for reverse-engineering your competitors and finding their gaps.
• Yesware Gmail extension finds out when people read your emails, can delay sending emails, and helps dig into loads of nerdy data.
What is the one book that you recommend our community should read and why?
“Tribe of Mentors” by Tim Ferriss. It offers advice and wisdom from the top achievers in the world. Tim does an incredible job of asking the right questions in the right order to get the best possible answers. It is impossible to read this book and not learn anything.
What is your favorite quote?
“If you want happiness for an hour — take a nap. If you want happiness for a day — go fishing. If you want happiness for a year — inherit a fortune. If you want happiness for a lifetime — help others.” – Chinese proverb
• Take some time at the end of each day to reflect on your successes and to set priorities for the next day. This can help you feel that much closer to accomplishing your goal and is a steady way to measure your success.
• Try walking, or biking, to work — even if it’s just a couple of days a week. Walking to and from my office gives me time to prepare for my day and decompress after work. It also ensures that I am present for my wife and adorable puppy when I walk in the door.
• Break your tasks down into bite-sized chunks. It’s impossible for me to accomplish anything if I am focused only on my big picture or end-of-year goals. Chunk up each goal into manageable tasks, and work on hitting two or three of those tasks each day. It will leave you feeling more productive and accomplished.
• Read “Tribe of Mentors” by Tim Ferriss. It offers wisdom from the top thinkers in the world.
• Take some time to exercise. It is essential for me to hit the gym regularly in order to be at my peak brain function. Exercise helps me mentally reset and be my best self at the office and at home.
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