Hello everyone. This is the next installment in my “Extra Income” series. If you’d like to be featured, please send me an email. Other installments in this series include: I Run a Resume Business, I Help Businesses Create Online Campaigns, and I’m a Creative Web Entrepreneur.
I specialize in redeeming frequent flyer miles for clients, helping them book award flights to destinations such as Paris and Thailand.
Most clients either don’t have the time to research award availability and routing options or aren’t familiar with what’s possible using their miles. That’s where my service, iflywithmiles.com, can help.
How did you get started with this side hustle?
My journey began when I registered a domain name during a promotion from a frequent flyer program that awarded miles for certain activities, one of which was registering a domain through an ISP. I didn’t initially plan to start a mile-redemption service — I simply chose the first logical domain name that came to mind related to frequent flyer miles.
Months later, a colleague mentioned he wanted to learn HTML and CSS. I realized I could put his new skills to use and asked if he would help build a website for a service I had in mind. He agreed to build the site at no charge, despite my offer to pay, and that’s how the service took shape.
What sparked your interest in this work?
I’ve long been passionate and knowledgeable about miles and points. Combined with an analytical, engineering-like approach to solving problems, building award itineraries is something I enjoy rather than find tedious. I saw an opportunity to help people who are short on time or unsure how to navigate the complex world of award travel, and I’ve continued learning helpful tricks and nuances as I work with clients.
Tell me more about your services
Clients typically provide their award account balances, desired travel dates, and destination. With that information I assess whether their trip is feasible and outline possible routings, cabin classes, and the miles required.
After reviewing options with the client, I assemble a proposed itinerary and share it for approval. Once the client agrees, I proceed to book the flights. I request payment after the bookings are completed.
What sets you apart from the competition?
My passion for travel and hands-on experience visiting many of the destinations clients choose help me offer realistic, practical advice. Having firsthand knowledge of airports, typical connection times, and regional nuances lets me design itineraries that work smoothly for travelers.
What has surprised you most about running this business?
I’ve been pleasantly surprised by how quickly word spreads through client referrals and by how willing past customers are to provide testimonials. Positive experiences translate into more clients through personal recommendations.
What’s the biggest lesson you’ve learned as a small business owner?
The key lesson is to own your service and consistently deliver excellent results tailored to each client’s needs. Doing great work pays dividends through referrals. I’ve also learned not to rely solely on SEO—search algorithms change frequently, and what ranks well one day can shift the next.
What were the start-up costs?
Start-up costs were minimal. The domain registration cost roughly $10–$20, I already had hosting through my travel blog, and a colleague provided the website design free of charge.
What is the most rewarding part of your side job?
The most rewarding aspect is helping people realize trips they might not have thought possible, creating memories that last a lifetime. I also enjoy reading the kind words past clients share when prospective clients ask for references.
What are your business goals for the coming year?
My goals are to maintain strong, positive relationships with existing clients while growing the business through referrals. On a personal note, I also have big travel plans, including an ambitious road trip from London to Mongolia in 2014.