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MenuTravel Hacking / Planning
Created a year ago in Other
After selling my first company, I set aside a budget to travel the world and planned 10+ trips within the next year. But I quickly realized that the cost of flying first class and staying at the best hotels adds up quickly! So I taught myself travel hacking - the art of using creative research and/or credit card points strategies to book flights and hotels at a fraction of their normal cost (and sometimes even free). These new skills allowed me to do everything my wife/I wanted while also feeling responsible (we are frugal people by nature!). Over the past 5 years, we've taken dozens of cheap or free flights to many bucket-list places around the world. On our most recent trip to Greece, our first class flights would have cost $15,000 had we paid cash. But thanks to a single strategy, we paid $0...just $350 in taxes. Our entire 16-night trip to Greece cost less than $4,000 including premium ocean-view lodging, gourmet food, first class, flights, etc. I've gotten pretty good at finding ways to travel in style for cheap, and I love teaching others how to do the same. I can also help with general travel planning if you want to experience the *real* culture of the place you're visiting (not just the tourism side). Don't be one of those people who comes home after a week in Italy with a dozen boring photos of Michaelangelo's David on your phone but no idea how Italians really live. I know all kinds of tips/tricks to minimize stress, keep expenses low, and make sure you have an incredible experience with stories and photos you'll cherish forever. :)
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Jesse Lear
Columbus, OH
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Hello! I'm a serial entrepreneur currently operating a boutique corporate housing company with ~40 furnished mid term rentals. We specialize in the MTR (mid term rental) model and focus exclusively on guests who book our furnished apartments for 30+ nights. I can help you shorten your learning curve with all things STR / MTR including: choosing properties that have high odds of profitability, designing/furnishing to wow your guests, optimizing your turnover/cleaning processes, mastering direct marketing and advertising, and much more. I've been a full-time entrepreneur since a just after college. My first real win in business was a valet trash & recycling company that I founded with a friend in 2010. After growing into 5 cities and 3 states, we were acquired by the largest company in our industry. I’ve been recognized as… —SBA Young Entrepreneur Of The Year —Empact 100 award at the United Nations —Entrepreneur magazine's Top 30 Startups To Watch …and featured in Fortune, Forbes, Time, Entrepreneur, INC, Fast Company, etc. I enjoy sharing what I’ve learned and helping others succeed, so go ahead and schedule a call with me. :) I look forward to meeting you! 30 minute minimum call length please.
Reviews (4)
Jesse was a wealth of knowledge in helping us get started with our MTR. Great person and great advice to help us be successful! I would not hesitate to recommend him to anyone who is thinking of getting into this space!
Source: Clarity Kristel Smith Jan 24, 2025Lots of valuable information I got from our call. Thank you Jesse.
Source: Clarity Jeizreel Cinena Sep 28, 2021Great mentor and leader! Willing to answer any questions I had.
Source: Clarity Bre fleschner Jan 2, 2021Our call with Jesse was simply fantastic. He set up the expectations at the beginning and centered the conversation on our goals. We walked away encouraged, affirmed and inspired to take our next steps. Thanks Jesse!
Source: Clarity Hannah Ostoj Aug 10, 2020the startups.com platform
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