092 | Optimize your Time, Money and Travel with Chris Hutchins of All the Hacks

all the hacks
Learn tricks to optimize your time, money, and travel getting in the way of connecting with others.

When you learn tricks to optimize your time, money, and travel it sometimes feels like you are winning at life.  My adventure win of the week is that we are beginning to plan bits and pieces of our gap year.  One of the things we decided to do was to make one big “wish list” experience for each kid to be their Christmas gift.  This week I booked my daughter’s wishlist item.  For fear that she might catch wind of this episode or use her superpower of eavesdropping, I have decided to keep you all in suspense for a bit.  I will say it will be one of the most touristy things we could do, but it is connected to one of her current interests.  The win was that thanks to miles and points, not only did I book the tickets with our magic travel eraser credit card, we also used Chase Ultimate rewards points to cover our hotel.  Over $2,000 of value thus far has been preserved in our gap year budget.  Our wins don’t need to be big.  Sometimes doing nothing for 15 minutes to step outside and not consume anything is a win. Heck, last week while playing the single mom card all week in the throws of my kids fall activities – food on the table each night felt like a win.  While I love a good optimization strategy, I have found that there is nothing to optimize relationships and being human.  My hope is that this episode today helps you optimize the stuff in your life getting in the way of you connecting with other humans (or even with yourself).  

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Our guest today is the ultimate  life hacker helping others optimize their time, money, and travel. I’ve listened to stories of him begging to go to boarding school, being an undercover agent to expose a pyramid scheme, creating a company in 48-hours, and even the back story on how he  convinced his wedding videographer to do his wedding for free (I guess technically it was about a $1,000).  His tenacity in the face of uncertainty is inspiring and he always seems to find unique ways to bring people together from hosting concerts, to Laid Off Camp, to speaking at South by Southwest.  He is a travel rewards guru but also looks at experiences differently.  An example is traveling the world in 8 months when he suggested to his wife to take a one-way flight with him to South Africa, couch surf as much as possible and find interesting ways to travel between cities.  After years of working in start ups and aggressively pursuing Financial Independence, he also seems to have landed as the founder and host of All the Hacks podcast.  Chris Hutchins is a dad of 2 young girls, and Chief Optimizer here to share his insights.  Chris, thank you so much for being here.  Welcome to Ordinary Sherpa  

Key Takeaways

  1. A great starter travel hack: Book your room directly through the hotel.  Then email the hotel directly (the local hotel not HQ) and share more about who you are and why you are staying there.  The number of extras people receive has been in the hundreds.  Hotels are in the hospitality game.  By interacting with them you are letting them do the things they are good at, which is hospitality.  By working with them direct you make it easier for them to build a relationship with you and provide a better overall experience.  
  2. Chris shared an experience where negotiating with the added challenge of culture and language barriers led to this escalating.  Even though he was in the right, it reminded him that sometimes winning isn’t saving a few bucks.  
  3. Living on $30/day did inspire finding the cheapest accommodations each night.  However if $3 meant three hours walking around town, there is a point when you have to recognize you will never get the three hours back. 
  4. Time becomes more important than money when you have kids.  Finding the value of 30 minutes is very different when your total free time is less than 4 hours as compared to 10 hours each day.  
  5. One way they optimized their life with kids was to hire someone from a Craigslist to bulk prep meals.  Sometimes optimizing means figuring out what management trick we can use right now without feeling like we need to create a system that solves all of our problems forever.  
  6. While they once traveled via the cheapest flights, the filter for searching flight options now includes the cheapest + direct flight.  
  7. Being a dad, he’s gotten more optimized on time strategies without sweating a small to moderate financial investment.  He’s much more likely to spend time with his kids than the hours he spent researching the best option earlier in his life.  
  8. Using the Lyft driving example, Chris was able to give his time a floor value.  Putting a dollar value on each hour of his time helped him realize the negative ROI of Do-it-Yourself type implementation.  
  9. Stacking two tasks that don’t need the same part of your brain is also a tip that allows him to maximize his time.  For example he might schedule a call while on a walk or listen to a podcast guest he is doing research on while driving or washing the dishes.  
  10. Do a calendar audit from time to time.  What lights you up and what can go away or be stacked on top of something else.  
  11. Having a THING to talk about when meeting new people to help build relationships.  Laid off camp was the thing people were curious about.  Better yet, listen more and have the others do the talking. 

Connect or Follow:
Podcast: All the Hacks
Website: ChrisHutchins.com
Email: chris@allthehacks.com
Facebook: @chrishutchins

Resources: All the Hacks episodes referenced in this episode

  1. 52 Places: The Art of Traveling Like a Journalist and Making Every Trip Memorable
  2. Hosting Cocktail Parties, Building Relationships, Museum Hacks and Friends Newsletters
  3. Rental Cars: Saving Money, Avoiding Fees and All the Secret Tricks
  4. Pro Travel Hacks for Every Aspect of Your Next Trip
  5. Maximize Your Points: Stacking, Buyers Clubs, Redemption Hacks, and More

Where to Listen

Apple Podcast, Spotify, Stitcher,  Google Podcast, anywhere podcasts are played