5 tips we used to save over $2600 on our trip to Hawai`i

budget, financial independence, frugal, how we win, travel

Much like our vacation to Iceland in the spring of 2017, our recent two week trip to Hawai`i was predicated on our desire to hike and experience the most exotic, beautiful, and lush destinations. As such, we didn’t travel hack it to an 85% savings rate like Asheville, Savannah, and St. Augustine, but we did save a good amount (like a couple thousand dollars) and wanted to share these actionable tips with you.

Our preference is to travel to our “bucket-list” destinations versus only traveling to locations based on the best deals/points to save money. It certainly didn’t hurt that we got to experience live flowing lava within about 20 feet of us that looked a little something like this:

Lava Flow 6 (2)

Dinner and a show, nice date night!

Before we delve in to how we saved money in Hawai`i, you might want to check out our previous travel hacking articles:

We’ll wait…

So, now that you are all caught up on our adventures, what did our Hawai​`​ian adventure entail? Flights from Florida to Kona, Kona to Honolulu, and Honolulu to Florida, 14 nights, two islands (Big Island and Oahu), and countless adventures. Our priorities are hiking and experiencing the beautiful landscapes this amazing world has to offer. While certain hikes in Hawai`i come with a parking / entrance fee, the vast majority are free and entail miles of beauty at no cost. Nature provides some of the best free entertainment (and exercise) out there!

If your ideal vacation involves parking yourself on a beach, Hawai`i certainly provides every opportunity for you to do that, and you can travel hack a beach destination itinerary relatively easy. Many other blogs will help you with that. We chose to explore and adventure as you’ll see in some of the pictures and descriptions below.

But first, here’s what we spent and what we saved.

Category Spent Saved Notes
Flights $33 $1,744 Unavoidable Fees, redeemed American Airlines miles to save on the 3 flights
Bag Fees $25 $50 AAdvantage comes with a free checked bag, we had to pay the baggage fee on the Interisland flight
Big Island Lodging $581 Averaged $83 per night (7 nights)
Oahu Lodging $289 $496 Averaged $96 per night (3 nights) for AirBNB’s. Savings came from Marriott Points (one night North Shore) and two nights of being housed by friends.
Rental Cars $520 $200 Booking through Autoslash saved $200 over booking directly.
Groceries $175 $140 We packed significant meals in our checked bag!
Dining $140
Gas $108
Misc. Fees $97
TOTAL $1,969 $2,630 Hey we saved 57%!



Sunrise hike into Pololū Valley


Patience and flexibility is key when booking American Airline award flights. We checked consistently for months, waiting for our exact criteria to be matched. We did this by defining our specific criteria, but being flexible with dates, and being ready to book as soon as the seats come available. Good things don’t last forever!

Where we weren’t flexible:

  1. We wanted to fly into one Island (either Oahu or the Big Island) and fly out of the other
  2. We wanted to have only one connection on the outgoing and return trip, and
  3. We wanted to pay with the most economical Economy MileSAAver points. Given the stresses of travel, limiting the number of connections was important as well as not having any wasted time flying back and forth between the islands. We also knew that we wanted somewhere around two weeks, which was the amount of time we felt would be worth it for the ~12 hours of travel each way, visiting two of the islands, and not leaving our offices in a bind.

Where we were flexible: 

  1. Primarily the dates as well as which island to visit first. So with the parameters set, we consistently checked for one-way flights to each island and waited for our exact criteria to be met. Finally, we were able to book our criteria: Tampa to Kona (through Dallas) and Honolulu to Tampa (through Dallas).

How we did it:

  1. We each used 45K American Airlines points to get to and from Hawaii. We also each used 7.5K American Airlines points to get from Kona to Honolulu. With under 52.5K American Airlines points each, the flights were paid for (except the minimal unavoidable fees).
  2. We both had signed up for the Citi Aadvantage credit card when offered at 60K bonus miles, fully paying for these flights with points to spare (total estimated savings of over $1,700).

Bag Fees Bonus:

American Airlines would have charged $50 round-trip for our one checked bag. Our previous Citi Aadvantage cards had both been cancelled, so no free bag perk there. This had me look at the Aadvantage Aviator Red card. For a $95 annual fee you get a free checked bag, priority boarding, and 60K sign-up miles (minimum spend of only one single purchase!)… therefore for a $45 fee on top of what I was going to be paying anyway for the checked bag, we might as well take advantage of obtaining another 60K American Airline points!  This is enough miles to get a round-trip flight to Europe or of course back to Hawaii with miles to spare! The $25 bag fee we did pay was related to the inter-island flight on Hawai`ian Airlines between Kona and Honolulu.

Note: Why did we need a checked bag? Usually we’re the type to maximize savings and not check bags at all by just being minimalist and going with carry-ons.  But you can’t bring hiking polls on a plane, so we check. Since we have to check, we cram as much as we can into the checked bag.


We stayed one night on a lava field… it wasn’t too cool. Hah! Get it?!


Big Island : We elected to stay with six different Airbnb properties for our seven nights on the island. That helped give us a variety of local experiences, meeting different hosts, and getting a feel for the variety of subcultures that permeate the island. As the Big Island is the largest of the Hawai`ian Islands (shocking, I know), we had our version of slow traveling the island, starting in Kona, heading North and eventually circumnavigating the island.  We strategically found Airbnb’s that helped (generally) keep each day’s driving to a couple hours or less from. The average price paid per night, including fees, was a very reasonable $83/night (definitely check the reviews!). We could have stayed on some of the big island resorts, but many have notoriously high fees (i.e. resort fees of $30/night and parking fees of $20/night). It made no sense for us to pay upwards of $50/night on fees AND burn through our points when we stayed in locations that were even better for our planned hikes and excursions.

Oahu : Oahu was a little bit more mixed, the island is much busier and more expensive for lodging. We also booked closer to our travel dates (and were traveling around spring break) which may have dwindled the available supply. Thankfully, we have two amazing friends who live on Hickam AFB and let us crash for two nights. We also took advantage of the Courtyard Marriott near North Shore for a night with available Marriott Points. While Waikiki has a majority of the resorts, similar to the Big Island, these often come with significant resort and parking fees (not as much of an issue if you don’t rent a car). Contrarily, the Courtyard Marriott near North Shore comes with no resort fees and a more reasonable $12.50/night parking fee ($10 when we visited). This property was charging over $300/night, so nice point redemption on that stay. The remaining three nights on Oahu were again spent in Airbnb’s close to our planned hikes at an average cost of $96/night.


Cue the Jurassic Park music… or the LOST ticking clock

Rental Cars:

Autoslash continues to be a fantastic website for finding and booking well priced auto rentals. We highly recommend you consider using them as a resource anytime you are looking for a car rental. They saved us well in the Southwest U.S., Asheville, and now Hawai`i with both bookings. We saved over $200 using Autoslash over booking directly through Hertz (which we had a fine experience and no issues with). Oahu does have a comprehensive bus system, but we opted for the car for convenience.


Eating out and enjoying local foods should be part of any trip you make. It’s a fantastic opportunity to sample new flavors, expand your pallet, and eat like a local, even if it’s just for a meal. With that said, Winning Williams likes to control our nutritional input, eating right and cost effectively. From a cost perspective, groceries in Hawaii are EXPENSIVE, especially compared to shopping at Aldi in Florida!

We try to control all variables that are in our power. Knowing how expensive groceries in Hawaii are, we started shopping in Florida, utilizing our checked bag to transport said food. We then supplemented with fresh goods upon arrival in Hawai`i (bread, tortillas, bananas, cheese, etc.) So what did we pack in our checked bag and could you do something similar to safe significant money while traveling: almonds, trail mix, beef jerky, peanut butter & jelly (supplemented with bread was a major lunch source), popcorn, tuna packets (major dinner source), instant potato packets (judge free zone right?), instant rice packets, and whatever else I’m forgetting at the moment!

There’s no question that we saved significantly by 1) grocery shopping and not dining out every meal and by 2) utilizing Aldi in Florida for non-perishables. We estimated $140 of savings from lower grocery costs alone.


On dining we spent a reasonable $140 over the two weeks which included delicious date night of Vietnamese food and ice cream, Malasadas (Portuguese donut), moco loco (rice topped with sausage, ham, and spam, fried egg, brown gravy), café’s, Hawaiian BBQ, to the basic we’re hungry and need cheap food now classics like Taco Bell and McDonald’s!


Many of the parks and hikes are free. A couple came with minimal ($5) or even as little as $1/per person fees. Completely inexpensive and worth it. The Volcano National Park was the most expensive with a 7-day park pass going for $25. It’s worth every penny to experience this national park!

If you would like more specific hiking/itinerary information, please feel free to reach out to us!


For reference, here’s a list of most of the hikes we did across both islands: Jagger Museum, Aiea Loop, Pali Puka, Diamond Head, Koko Head, Lanikai Pillbox, Makapuu Point, Ulakaa Trail, Keana Point, Laie Falls, Manoa Falls, Wiliwilinui Ridge, Pearl Harbor, Crater Rim Drive, Kalopa State Park, Kilauea Iki and Thurston Lava tube, Akaka Falls, Carl Smith Beach, Laupahoehow Point, Onomea Drive, Rainbow Falls, Peepee Falls, Lava Hike!, Lave Tree State Park, Mackenzie Recreation Area, Manua Kea, Pololu Valley, Wipio Valley, Honomalino Bay, Punaluu Black Sand Beach, Pu’ukohola Heiau Park.


We saw, we savored, and we saved! What are your next trip plans?


A BIG Thank You:

Part of our trip involved an amazing morning of surfing with the legendary Nords over at The Military Guide. He was very patient with us and we learned a lot! The surfing lesson was fun and exhilarating, but the conversation afterwards was equally rewarding. Being about to connect with and discuss our favorite topics with someone who has such a vast wealth of knowledge was great. We met Doug back in January at CampFI Southeast. We have made some great friends at events like these and what could have just been another day of hiking by ourselves turned into an amazing morning that was one of the highlights of our vacation. Actionable tip here is: be open to interacting with others. You might make new friends or connections that can have a positive lasting impact!


And the Videos:

Big Island:




The only budget you’ll ever need

budget, early retirement, financial independence, FIRE, how we win, personal finance

Winning Williams budget has certainly evolved over the last few years. Evolution like humans morphing from caveman with limited cognitive ability to the humans of today with complex thinking and rather strange behavioral patterns. But before we go down THAT rabbit hole, we wanted to present a simplified version of our budget for you the reader to download, copy, and make your own.

We’ve referenced why we think a budget is important here. Most importantly, nobody will care for your money like YOU. Maintaining a budget is taking ownership of your financial life. Analyzing the numbers makes it blatantly clear your strengths and weaknesses as well as opportunities for improvement and optimization. We all want transparency from our employers, loved ones, and government leaders (good one, right?), a budget will give you clarity into your financial world of operations.

Here is a link to the budget: Download Excel Version of Best Budget Ever!

A few notes:

  • This is a simplified version and we will update with more advanced tabs at a later date
  • Included is sample data, they don’t represent Winning Williams actual financials (sorry Internet Retirement Police)

Please post any comments that you have below, we will get back to each one as soon as we can. We’d love to hear from you!

How we spent less than $300 and saved 85% on a week long vacation covering 4 states

budget, cut expenses, frugal, how we win, travel

The Winning Williams explored the beautiful mountains and Blue Ridge Parkway surrounding Asheville, North Carolina at the end of October. Following three beautiful days hiking through the mountains, immersed by fall foliage and its golden and rosy colors, we headed to the striking streets of Savannah. This was this the first of two days exploring and experiencing the charming and historic southern cities, with a day and evening sightseeing St. Augustine capping off the vacation. We then drove the 2017 Kia Optima rental car back to Tampa, ending the journey.

There were six hotel nights, a flight to Raleigh from Tampa, the aforementioned rental car that covered 1,200 miles on a one-way rental, delicious dining, wine imbibing, and even a distillery tour and tasting.

The cost for everything, including food, was $273. This easily would have cost $1,500 if we didn’t travel hack or plan the way Winning Williams does. This was our fourth travel hacking trip, following Iceland, New York City, and the Southwest U.S. journeys.

We optimize what is important to us and travel to where we are most interested. We know our priorities: hiking in stunning locations and simply enjoying nature (a nice change from our office jobs); also exploring areas that have historic charm / history / culture / something unique. Your priorities will differ, but until you define them, you can’t optimize. Our passion for hiking in new and unique places offers a direct challenge to optimizing and saving money: you need a rental car to get to the different locations and you often have limited hotel choices that can limit travel hacking opportunities. Winning Williams is okay with that trade-off, we’ll spend money where it matters most to us.

With that said, how were we able to save 85% on this trip?



We had two airfare options: fly to Charlotte or Raleigh. While Charlotte was an hour closer to our first destination of Asheville, Raleigh offered the distinct advantage of direct flights via Southwest. We could have used 25,000 of our American Airlines miles (for two passengers one-way) to fly direct to Charlotte; instead we used just 10,000 aggregate Southwest points to fly direct to Raleigh, saving future airline miles. Of course Southwest provided free checked bags adding an additional bonus so we can bring our hiking polls and food with us (see below for groceries) for free. But the flight consideration highlights a key to saving money and travel hacking: flexibility.

  • Cost: $11.20
  • Savings: $178 + a free checked bag

Rental Car:

While we didn’t book our car rental through Autoslash, a quick scan of a promotional e-mail they sent caught my eye. Hertz (and certain other brands) were (are?) trying to move some of their inventory to warm and sunny Florida to support all the snow birds. The promotion was a $5/day rental if you rent a car one-way from along the East Coast and drop it off in Florida. Given how expensive rental cars can be, this promotion was quite the incentive to take a trip and see Asheville, Savannah, and St. Augustine, three cities that were on our to-visit list. Then we could simply drop the car off right by the airport nearby our residence. The promotion was eligible for the most inexpensive economy car up through a few levels to arrive at a Group D rental. We of course moved up as far as we could, the cost was still $5/day, why not get a little more power and size!

  • Cost: $73 total with fees (the unavoidable fees increased the cost to about $12/day)
  • Savings: $180 on roughly $30/day over the estimated rate/fees excluding the promotion


Asheville, North Carolina: Four Points Sheraton: Three Nights – FREE

In Asheville we stayed at the Four Points Sheraton using SPG points. The hotel was within walking distance of downtown AND offered free parking. Several other properties were charging $20/night+ for parking. Total Points used: 21,000 SPG points.

Irmo, South Carolina at Hyatt Place: One Night – FREE

Splitting the drive between Asheville and Savannah, we stayed at a Hyatt Place in Irmo, South Carolina, just outside of Columbia. By staying outside the city, the Hyatt Place was a category 1 property, only requiring 5,000 Hyatt points. We’ve always had fantastic stays at Hyatt Place’s and would recommend them (pro tip: great breakfast buffets)!

Savannah, Georgia at Springhill Suites: One Night – FREE

Savannah was the most challenging location to find lodging. There are several chain hotels in the downtown area, but each required more points than we would like to use AND required expensive parking/resort fees. *Parking itself was a bit challenging there and that was even with mapping parking garages before coming into town!

We selected the Springhill Suites midtown, a Marriott property. This was located several miles out of the central downtown, but provided exactly what we needed, a quiet restful sleep, after another long day of exploring and walking. And free parking. And free breakfast. The Springhill Suites was 15K Marriott points, which is on the lower end for Marriott properties and at least half of what downtown Savannah would have required.

St. Augustine, Florida at the Holiday Inn: One Night – FREE

The Holiday Inn is located at the North end of the primary walking downtown district and again, I’m getting a bit repetitive here, offered free parking. We recently signed up for the IHG credit card (80K initial bonus rewards offering) for the sole purpose of booking this hotel. It required a little more points, 30K, but was the final piece of the puzzle of a week of free lodging.

  • Cost: $0 total with fees
  • Savings: $1,136 on six nights at the locations above, this would have worked out to $189/night.



Breakfast: complimentary breakfast was provided for five of the six mornings in the hotels. We’re not sure if our special SPG status resulted in free breakfast those three mornings in Asheville or if we somehow lucked out and got grouped with a larger traveling group that was staying at the hotel. In any situation, we took advantage of said breakfasts like any Mustachian would, and ate rather well to start each day J The Holiday Inn was the only location that we would have had to pay for breakfast. We had some gourmet Pop-Tarts from Aldi instead.

Snacks/Other: With our free checked bag, we loaded up on snacks from Aldi before the trip. Our first stop upon arrival was also at a Wal-Mart to get the fresh items (and wine) we wouldn’t want to check. These items gave us the needed nourishment to hit the trails, during the long drives, and supplemented our meals (well the wine was separate). We’re talking almonds, trail mix, crackers, apples, cheese, bananas, chips, cookies (night-time desert), etc.

Lunches: Most days we were out and about and possibly without any food options. That’s perfect. That’s exactly what you want (well at least we do) when getting away, and especially for hiking. Our go to lunch: tuna packet in a tortilla with cheese, perhaps with some avocado or simply BBQ sauce for additional flavoring. Add in trail mix, an apple, and other side items and you’re good to keep going. Cost per lunch was very minimal.

Dinners/Eating Out: Our second night in Asheville, we went to Papa’s & Beer. Absolutely delicious Tex-Mex and the usual huge portions. Does anyone actually eat the full meal?! Don’t answer that please.  After loading up on free chips at the restaurant, we ended up getting TWO nights of leftovers from this meal (and we supplemented with some of the other snacks). That’s half of the dinners! Then we feasted at Zunzi’s in Savannah. We somehow scored an extra sandwich with some R&D efforts they were conducting. Zunzi’s helped cover a couple dinners with the bonus food.

  • Cost: $53 (Zunzi’s & Papa’s & Beer) & $36 for groceries = $89 (less than some will pay on a single meal out)

Let’s summarize where we are at and the total cost:

asheville costs

So we talked about flights, car rental, hotels, and food above. Outside of those items, we spent $100 on an Uber to the airport, parking in Savannah, and gas. That totals $273 total trip costs!

How else did we save:

  • Asheville is EXCELLENT for hiking. Simply research beforehand where you want to hike, get your directions, and hit the road. Nearly all hiking in the area is FREE. Check out Romantic Asheville. It was a fantastic website for exploring different hiking options. Also, check road conditions if you are going in the wintertime (late October and onward). We had to utilize some alternative hikes as part of the Blue Ridge Parkway was closed for the first day we were in Asheville.
  • Savannah and St. Augustine are very walkable cities. You can peruse their visitor information centers for maps, etc. But, we researched everything prior to arriving, had maps, self-guided walking tours, etc. Therefore we got most of the same information you would get from a paid tour, with our pre-trip preparation.
  • Take advantage of free activities!
    • Check the tourist information centers / local websites calendar for events that might be happening when you’re there! We were in St. Augustine on the First Friday of the month. That happens to be a day when many art galleries open with special features like free wine and snacks! We also experienced a couple artists painting live and interacting with guests as part of the event. It made for a very special and romantic evening with Mrs. Winning Williams.
    • Augustine also has wine tours (with a free tasting) at San Sebastian Winery and distillery tours (with a free tasting) at St. Augustine Distillery. Check the websites for available times and its of course great to patronage these locations as you deem fit.

12.8 St Aug


And here is the video of our hikes:

How I hacked college and graduated with a $50,000+ POSITIVE Net Worth

books, budget, cut expenses, debt, education, expenses, higher education, how we win, Uncategorized

I completed my undergraduate program in 2006. After four years of university schooling, I graduated with two degrees and no student loans to show for it. Scratch that, over $50,000 Net Worth to show for it. When most people were  graduating with material debt and a certificate they hope will yield untapped earning potential, I was able to do something that seemed unthinkable.

Like most other things, I never felt as if I did anything special. But, my experience does highlight how attacking the problem of paying for college from several angles can lead you to a favorable outcome. The same driving forces for an accelerated timing to reach FI applies here (increasing your top-line income, while controlling your bottom-line expenses).

How I Went To College For Free – scholarships, living intentionally, etc.

  • The scholarship – the state of Florida has a fantastic offer for in-state residents called Bright Futures. It’s largely funded by Florida lottery and provides scholarships to eligible students. Back in 2002 when I was graduating high school, there was basically a 75% or a 100% of tuition coverage award if you stay in-state and met the criteria. I was offered the 75% scholarship and The University of South Florida offered the remaining 25% if I went there. Graduating around the top 10% of my class in high-school was helpful here. USF was the only state school to offer me the 25% remaining scholarship, which took care of remainder of tuition. Boom, tuition covered.
  • In-State University – I went to a state-university in Florida, shout-out to the University of South Florida, go Bulls! I had acceptance at all the major state universities, but a couple of the top ones are in locations without as many internships or part-time job opportunities at large companies. USF has several partnerships and programs with numerous companies located around the Tampa Bay area. This meant building experience with paid-internships through my last two years of university while attending classes. There is no question this was vital in receiving my full-time job offer before graduation.
  • Live At Home – The campus was about 20 miles from my parent’s house. I was fortunate to stay rent-free at home. As money-minded parent’s, the offer was live there for free, or pay for everything yourself if you don’t. Fair offer! Needless to say, I took them up on that
  • Scheduling – Since I was commuting a bit, I grouped classes to minimize extra driving and maximize opportunities for part-time jobs/internships.
  • Extra Credit – I took an AP in class in high-school and earned college credit. I probably should have taken more AP classes and gone into college with more credit. But with the scholarships received, the savings would have been marginal.  

Work It – Jobs and Internships

  • Part-time job 1 – I worked at a tennis club all throughout college. It was pretty ideal: I got to play tennis and get paid for it (does that make me a professional player?), hours were flexible, it was two miles from home, and I was able to study on the job. Well, the pay kinda sucked…
    • I did this job in high-school as well so I had a positive Net Worth heading into college

The following jobs were all done in conjunction with the tennis club position. My time in college can be summed up in one word: “Hustle” NOTE: for those currently looking to go into college or in college and in search of some money,  utilize the career center for opportunities and networking.

  • Part-time job 2 – I sold cutlery. This lasted for all of six-months and was a challenge for me as an introvert, but that also made it a growth opportunity. This stint was with the (in)famous Cutco cutlery and their usage of college students to sell REALLY expensive cutlery. It was a pure commission sales job. I do feel a little bad selling such expensive cutlery now, but my one remaining Cutco knife I own is seriously legit- more than 10 years later! I also won a sword as an award for my sales, so there is that


  • Internship 1 – I utilized the school’s resources to earn a paid internship with a local newspaper marketing research team. Instead of working the standard 4-6 month internship, I negotiated an extension. This turned into six-months of paid work, padding both my resume (1 year at the company) as well as my bank accounts.
  • Internship 2 – Staying with marketing research, I had a stint with a pharmaceutical company, receiving a whopping $10/hour wage (wahoo!) for a roughly six-month internship (best hourly rate at that time).

Keep Working It – Side hustles

  • Additional scholarships – My tuition was 100% covered with scholarships as detailed above. However, by talking with the School of Business advisors, I discovered that with a basic GPA requirement and filling out a simple 2 page form, I would be eligible for additional scholarships. I think I received a $2,000 scholarship one year and a $1,500 scholarship the next, simply by filling out this form. I also got to attend a cool banquet, met the President of the university, and got FREE FOOD. These scholarships came in the form of a check to me, straight to the bank, and therefore income. Reader takeaway: research common and niche scholarship opportunities, take the low hanging fruit and unique ones with less competition.
  • Textbooks – I actually made money on some of these! Traditionally textbooks are outrageously priced and the textbook industry is certainly flawed. But, did you know that you could find “international versions” of the textbooks online? Instead of costing $150, it may cost you $15. The international versions were slightly different, they would have a soft-cover and would be black and white. Every now and then, an end-of-chapter question might be out of order. The difference was typically inconsequential, especially for those who rarely opened them The reason this was included in income and not expense saving is because I hustled these books to my classmates. I would write the professor for permission to email the class and let them know I could pre-order the books and have them ready for day one. If the professor obliged, I’d then order 10-15 of these international books, mark them up for a nice profit, but also save my classmates money in the end. Win win.
  • Video Game sales – I don’t actually recall how I got into this, especially since I was never into video games. Nonetheless, I became a dropshipper for selling video games online. I’d use the typical online auction platform to sell the games. The orders were filled by the distributor and I received a commission. Bonus: I sold enough games to earn a free game for myself. Why greedily take a free game when I can research what game was selling for the highest amount and resell that for my own personal profit?! Did it, made more money. Boo-yah!

Self Note: I need to get back on these side-hustles. Come on WW!

Other hacks and notes

  • Two Degrees – I started as a Marketing major and Finance minor. However, the internships help me discover going into finance was much more in-line with my interests (SPREADSHEETS!). I took an additional two classes to stretch the minor into a second major. Bonus for my entry into my 10+ year career now working in finance.
  • Join organizations in your school (i.e. for the School of Business perhaps join the American Marketing Association / Student Finance Association) – These are great for meeting like-minded individuals, surrounding yourself with more dedicated students, finding job/internship opportunities, and building that resume. Develop oneself!
  • MBA bonus degree – I also “hacked” a Master of Business Administration. Not quite as intense as undergrad, but I utilized employer programs which paid for the tuition. Again, this took dedication, working full-time job and going part-time to school in the evening. While the actual material was only slightly different from my undergraduate program, it provided more networking opportunities and with a deeper commitment of students.
  • Build a relationship with a professor or two – Select a couple professors that standout from a development and connection points of view. While some professors have been just that, academically developed in schooling only, many others have valuable work experience and relationships that are much more meaningful than what the textbooks will tell you.
  • Greek life… this is an interesting one as I always had a disdain for those in Greek life and thought it came with undue costs. It can be time-consuming, filled with ridiculous commitments, and did I mention expensive? This is an outsider’s perspective. I know many, including Mrs. Winning Williams had a great experience in Greek life, grew socially, and still have great relationships from that time. So I’ll keep a neutral opinion there.
  • Live At Home – This flows into I didn’t have the traditional college experience living at home, and I probably missed out on establishing what could be life-long friendships, which is truly invaluable. Nonetheless, I was able to leave college with a significant Net Worth and I can still build my community today, especially with fine folks in the FI community!


And with all of that money in my bank account, I bought a house… in 2007. We’ve already covered that journey.

A brief history of Winning Williams

budget, cut expenses, debt, early retirement, financial independence, FIRE, frugal, get out of debt, how we win, personal finance, retirement, savings

Many on the path to financial independence often talk about a big moment where they decided to give up their spendy ways forever and start saving for an early retirement. Our story has no such moment, sorry folks. Saving was never an issue for either of us. But, there was a time before we discovered the FI community when we blindly saved without early retirement or a specific goal in mind

So how did this all happen? When we met (and fell in love, and held hands, and made googly-eyes at each other), we were both already big money nerds. We both had spreadsheets, although Mr. WW’s spreadsheet was pretty sick.

At the end of 2012, I, Mrs. WW (still a Ms. at that time) repaid my student loans and Mr. WW repaid his mortgage. We celebrated with a wild and crazy night on the town – hot dogs and ice cream sundaes for a whopping $12 (after coupons). Wild AND crazy!

We had prioritized debt repayment and with that out of the picture, we had a surplus every month without any direction to funnel it into. We looked over our budget and asked some questions: “should we put all this extra money into trips?” “could we try to retire early?” “nah, we don’t have that much money.”


So, we did what any typical American couple would do… we spent it. But, not in a “jet planes, islands, tigers on a gold leash” kind of way. We did the monthly dinner at a local restaurant with our church group. I bought a few groupons to get my nails done, had my hair done regularly, and started getting a monthly Birchbox. Mr. WW got two fancy SPF shirts. In all, our additional spending didn’t really make a drop in the bucket.

Somewhere during this time, we got engaged (YAYAYAY!) and we had direction for our extra money now. (No!) We knew that we wanted to be true to ourselves when planning the wedding, so while it wasn’t free, it was nowhere near the national average cost. A few months before the wedding, Mr. WW stumbled on a website called “Early Retirement Extreme.” This got us thinking, and sometime in 2013 we took the 21 day challenge.

While we didn’t buy into many of the changes (we wanted more than roman noodles, lentils, and beans), it opened us up to challenging common thinking and eventually led us to many other blogs (including MMM, Frugalwoods, and most recently Our Next Life). This all took place about six months before we got married in 2014. A great time to have these financial conversations, but too late to back out of our dream wedding so we still enjoyed that big expensive party!


In 2013, the master spreadsheet was born and financial tracking began. This has taken a life form of its own. We primarily started tracking all of our spending by category, Net Worth by quarter, and savings rate. We made progress detailing each line item and asking ourselves if that expense aligned with our priorities and values. It has now morphed into a 20+ tab spreadsheet highlighting different financial aspects (tax planning, asset allocation, FI planning, etc.)

The reason we are now striving for FI is to live life completely on our terms and without the day to day necessity of a job. By removing the chains, we can travel freely (and perhaps cheaply via slow travel), spend more time with family, and enjoy what this world has to offer. By living this frugal lifestyle, we know we can handle what life may throw at us (layoffs, downturns, other challenges) and with less stress.


So how does any of this personal information help you? If you are like us and want something more out of life, then check out the vast library of information available in the F.I. community. If you read through the blogs and think “wow, that’s great for them, but my story just isn’t that exciting,” well guess what ours isn’t either. We were big savers and now we are big savers with a purpose. It doesn’t matter how big of a change you made to get you to FI it just matters that you get there on your own terms.

Iceland: Tips, Itinerary, and How we saved $1500!!

budget, expenses, frugal, how we win, travel

Sorry for our long delay in posting, we’ve just returned from the first travel-hacked trip to Mars:

winning williams mars

Land near Lake Myvtan in Northern Iceland looks just as open, empty, and red as Mars!

Just kidding, we went to Iceland and saved a ton of money leveraging all that we learned from Travel Miles 101. Yet again, our travel savings are north of $1,500 dollars. Here is what we did, how we saved, and how you might be able to use some of our tips on your own trip:

Epic Ring Road Iceland Itinerary

-Specific tips to maximize your experience and help you save-

We just returned from an awesome, awe-inspiring trip to Iceland. For those of you thinking of traveling to Iceland we have some tips that might help you make the most of your vacation!

Our trip was taken in May 2017, considered shoulder season in Iceland. We prefer to travel during this time for three reasons:

1) the weather was improving and great for hiking

2) there were fewer tourists than in the high season, making navigation and hot spots less populated

3) pricing hasn’t reached peak levels given the moderate tourist levels.

While the weather was improved, it was still Iceland. Keep in mind that when you travel there the weather can be volatile no matter the season. You can easily experience multiple seasons in a single day, and that we did on multiple occasions. For this reason, you need to be prepared to be somewhat flexible in for plans and prepared for what Iceland is going to throw your way.

Before we get into our itinerary, here are some helpful tips to help you have a smooth stress-free vacation to beautiful Iceland:


  1. Credit Cards / Gas

Using credit cards in Iceland is easy; we used ours for every transaction and did not pay for anything in local currency (Icelandic Krona). This made it very convenient and the exchange rate was pretty straightforward in May 2017 (roughly 100 Krona per $1 USD).

Make sure your credit card does not charge fees for foreign/international transactions. Many don’t, but it is wise to confirm before your trip. You should also let your credit card company know that you will be traveling internationally (and what dates) so they don’t freeze your spending while in Iceland!

One of the most important things you need to do with your credit card is to set a PIN number associated with it. This is one of the functions of the new chip cards. Pretty much all over Iceland, the gas pumps took credit cards, but for international visitors (like us) it required that we enter a PIN number with our chip card. No PIN, No gas! We did not do this beforehand (oops!) but, found a workaround at N1 stations.

One of the most prevalent gas stations in Iceland is the N1. Great gas station, many of which (not all) come with a restaurant / shop of some sort inside along with updated road conditions. Inside you can buy a prepaid gas card in various increments (roughly $10/$30/$50 increments) and use that at the pump outside. Naturally this is much less convenient than being able to fully fill up without having leftover krona on your prepaid gas card. However, we bought several prepaid gas cards along the way at N1 locations (sometimes with maps.me described below), and they always seemed to be in reach.

NOTE: You will also want to fill up your tank as much as possible. Some days we would be driving for hours before seeing a gas station. If you have a half a tank or less and see a gas station, it is time to fill-up.


Oh you know, just the glacier behind our hotel…

  1. Maps.me

The Ring Road is a simple drive on the perimeter of the country that offers breathtaking views at every turn. We made several stops for hikes, lodging, etc. along the road

Instead of getting an Icelandic SIM card, using cellular data, etc. we went old school with a couple hard-copy maps and printed Google directions to each stop. However, this couldn’t help us if we made a wrong turn (a couple times the sign we needed was blocked by another vehicle) or in one case when Google Maps was wrong (which did happen).

Our saving grace was Maps.me. We didn’t need it often, but the couple times we did absolutely saved us from getting lost, potentially to back-track, or just simply ditch whatever stop we had hoped to make.

Maps.me is a free app you download to your phone. You then select it to download Iceland (before you leave for your trip when you are on wi-fi) and then you can zoom in and put pins at each of your desired locations. We literally pinned every hike and lodging we stayed at. While in Iceland, my phone was on airplane mode to make sure I didn’t get hit with any roaming charges, etc. Maps.me allowed us to see where we were the couple times we got misguided and showed us how to get back on track.

I was shocked it could actually tell where we were when in airplane mode. Nonetheless, Maps.me was absolutely crucial the couple times we needed it and was completely free. It also allowed up to zoom in when we were near a town to determine where the closest N1 gas station was for our aforementioned prepaid gas card needs.

  1. Parking into the wind.

Icelandic wind is no joke. Apparently it is third most windy country in the World. When we picked up our rental car, they told us to park into the wind (so that it would be difficult to open your door). The opposite could be detrimental. The wind can be so strong it can literally rip the door of the hinge. Of course, you don’t always have that option to park into the wind. Simply hold on tight and be ready for the wind to gust at any moment. Just something to be cautious over.

  1. Bring Food / Buy Groceries / Eating Out

Iceland food is very expensive (easily $15-$20 per person for lunch or $35-$50+ per person for dinner) depending on your tastes. That shouldn’t come as a surprise given it is an island near the arctic. Food needs to get shipped in, as goes gasoline needed to transport the food around the country.

Nonetheless, check the Iceland Customs and Border Patrol website for permitted food. We went to Iceland largely for the hikes, not the food (okay, well their famous hot dogs were on our list) and bought food in the U.S. and stored it in our checked bags. This will save you SIGNIFICANTLY on costs. I think each person is permitted to bring 3.5 pounds of food, avoiding the obvious items, raw meats etc. (again check online). We brought peanut butter, jelly (utensils & Tupperware), multiple bags of trail mix, almonds, a dozen tuna packets for dinners, cheerios, power bars, etc.

Upon arrival in Iceland we went to Bonus (big yellow sign and pink pig on it), which is Icelandic’s discount grocery store. There we picked up the breads and wraps for our sandwich making, additional snacks/treats, and some bananas and apples. This served a majority of our meals (breakfast was largely covered by our lodging).


-Groceries packed in our checked bags: $40.00

-Groceries while in Iceland: $33.92

-Meals out: $78.51

That’s right, it cost us more to eat two meals at the airport, one meal in country, and an ice cream date than it did to buy groceries that fed us for the rest of the week. 

  1. Car Rental

We rented from Cars Iceland and had a good experience. While I can’t compare it to others, they seem to provide newer cars and provide additional insurance as part of their price. Iceland comes with certain challenges you might not be accustomed to (gravel roads, sand/ash, etc) and as such we went with the full insurance package. We picked up our small automatic Toyota Yaris with less than 6,000 kilometers on it. It came with heated seats and enough zip to survive the mountain passes, etc. We did go much slower than recommended on the gravel roads to make sure we avoided rock damage as much as possible. Unless you plan on going inland to the marked F-roads we believe a car of this size is perfectly acceptable over a larger more expensive and less gas efficient SUV. Gas is EXPENSIVE in Iceland! Think $8/$9 a gallon.

  1. Get OFF Ring Road for a short distance to avoid some gravel roads

The majority of the Ring Road is paved and easy to drive (even with high winds). However, at one junction in East Iceland (along the East Fjords) you have a choice to stay on Route 1 and go inland (outside Breiðdalsvík and on the way to Egilsstaðir) or stay on the coast with Route 96, connecting to Route 92, which meets back up with Route 1. We chose to stay on Route 1, the weather was fine and the first part of the journey was enjoyable.

There were some gravel roads, but we were able to manage them slowly. However, at one point the fog and winds significantly picked up and this was while going up and over a mountain with gravel roads. Visibility was just a few feet and the roads were very narrow. This was truly a scary drive and we were extremely fortunate nobody was either behind us or coming ahead. Maybe we had bad luck with the weather at that moment. Nonetheless, I would highly consider the connecting Route 96 to Route 92 even though it will take you a little out of the way.

When we did our research many sites just said “oh, you can stay on 1 or take 96.” For our purposes, if we had known this stretch of Route 1 was gravel we likely would have opted to take 96 instead to spare our little rental the hassle of trying to get over the unpaved roads.


Sitting on the edge, watching the water fall, and loving every minute!


Iceland Tips aside, here is a 7-day Ring Road Itinerary that could be used as a guide with your individual planning. Note: we arrived bright and early (in the rental car shortly after 8 am) from the U.S. and had a FULL day to start exploring the beautiful country:

Day 1:

  • Krysuvik-seltun – geothermal area
  • Reykjadalur Hot Springs
  • Bonus Grocery Store
  • Seljalandsfoss / Gljufuafoss – beautiful waterfalls
  • Skogafoss Waterfall, plus trails (at the top of the waterfall and continuing back)

Day 2:

  • Dyrholaey – top of the cliff
  • Reynisfjara Beach
  • Fjaorargljufur (canyon)
  • Skaftafell National Park (Vatnajokull)
  • Svartifoss (part of Skaftafll) / other hikes

Reynisfjara Beach

Day 3:

  • Jokulsarlon Lagoon
  • Hengifoss (if there is time, this was the instance where Google Maps led us astray and Maps.Me saved us from missing this amazing hike)

Day 4:

  • Dettifoss
  • Asbyrgi Canyon – NOTE: the roads to get here were closed in May 2017. So we would recommend checking to see if the roads are open. If the roads are not open to Asbyrgi Canyon – explore the Myvatn area:

Lake Myvatn:

  • Skutustadagigor
  • Hverarond/Hverastrond Sulphur Springs
  • Krafla
  • Namaskard
  • Grotagjarvegur cave
  • Haverjfall
  • Dimmuborgir

Hverastrond Sulphur Springs

Day 5:

  • Explore Myvatn (list above, unless you explored yesterday)
  • Godafoss
  • Explore Akureyri (second largest city in Iceland)

Day 6:

  • Glymur (longer hike). Part of the hike involved crossing a river that you had to navigate on foot while holding onto a wire cable. The water was “refreshingly” cold.
  • Start Golden Circle – Þingvellir. (we stayed between Þingvellir and Geysir/Strokkur)

Day 7:

  • Continue Golden Circle:
  • Geysir (strokkur)
  • Gullfoss
  • Faxi
  • Explore Reykjavik

Stokkur Geysir

Day 8:

  • Depart ☹


  • Travel during shoulder season
  • Bring your own food and avoid dining out. Many people travel to Iceland for the breathtaking views, not the food.
  • We used the Travel Cash Back rewards from the Barclay’s Arrival Card ( we each have one) and a Capital One Venture card to earn $1,524.97 back on our travel costs associated with the trip (total cost was just about $3,000). The majority of our travel costs came from hotels, our car rental, and airfare. There are few chain hotels making it difficult to save on lodging.
  • We didn’t find a way to use points for our Icelandic Air tickets and with a direct flight option available from Orlando ( a short drive from Tampa) we jumped at the chance to go on our dream trip.
  • All of our hikes and stops were FREE. We could have gone to the Blue Lagoon or taken a Whale Watching Tour, but we found other alternatives that were really fun and free. Our only costs were hotels, groceries, gas, and two excellent hot dogs and farm fresh ice cream 🙂
  • Feel free to message us if you have any questions or comments!


**Update: We finally made a video of our trip:

Why you should never get a 30-year mortgage

budget, debt, personal finance, savings

To own a home is said to be the American dream. And for many, this is true. A dream of fixed monthly payments over 30-years vs. an unknown amount of rent increases, landlord dealings, and potential moves. You acknowledge the short-comings of home-ownership: maintenance issues, property taxes, home insurance, etc. However, these items offset the uncertainties that come with renting AND you get to build equity in the process. Many believe that equity is as good as easy money that they can one day tap into.
The chart below as provided by fool.com, highlights this fact that a significant chunk of America’s Net Worth is tied to their homes.


The scary part is this money is tied up and is not available to spend.

The problem is the 30-year mortgage. Our inability to stay in one place for any length of time doesn’t help the situation either. Generally speaking, home ownership is only beneficial financially to the owner, if one stays at a location for a significant length of time (at least greater than 7 years). Transaction costs are enormous and equity is generally built in the back of the mortgage given the amortization schedule.

Other pitfalls of purchasing a home include the other players involved in the transaction. Who are your counterparts when purchasing a home? Real estate agents (profiting off the more expensive and larger home you buy) and bankers / finance agents, who yet again profit with a more expensive and larger home. While their interests are supposed to align with you, they don’t. They make more money by getting you into the largest home and financing the largest amount you can afford. The 30-year mortgage is the conduit to get you into that home. That leads us into the first issue.

Key Issue 1: a 30-year mortgage helps you purchase more home than you could possibly need.
Your income dictates the amount of money a bank is willing to lend to you. Several factors go into this calculation, but generally speaking a lender is willing to offer around 30% of your income towards a mortgage. We’ll use $1,500 a month as a proxy ($60K annual household income equivalent) and this will include P&I (principal and interest on the mortgage) as well as Property Taxes and Property Insurance.


For simplicity: property taxes, property insurance, and interest rate were held constant. In reality, each of these variables would be less expensive for the 15-year mortgage scenario and would save an even greater amount than what is presented below. The larger home would also cost an additional amount of maintenance (generally estimated at 1% of a home value annually), utilities, etc.

In summary, both scenarios require a payment of $1,500 a month, but the 30-year mortgage gives you the “opportunity” to purchase a home that will set you back an additional $100,000.

If you can’t afford to purchase the home you want with a 15-year mortgage, you should wait to buy.
This would mean that a significant amount of people who think they are ready to purchase a home, would have to continue renting. Or, perhaps rethink the size of the house and associated cost to bring down the cost to an affordable 15-year option. The supersize me lifestyle has certainly affected what we perceive we need in a home. From 1973 to 2013, there was a 91% increase in square foot per person. In 2013, this resulted in over 1,000 square feet per person. The following graph shows that while the average household size (number of occupants) decreases, the average size of a residence (sq. ft.) continues to shoot upwards.


You’ll need to ignore your real estate agent telling you what amazing house you can afford and instead focus on the core fundamentals of what you need in a property and what you can afford on a 15-year basis.

Key Issue 2: You pay significantly more in interest expense during the 30-year term.

You pay a proportionally larger amount of interest expense using a 30-year mortgage. Let’s continue the example from above and show how much money you’ll save by purchasing the home you can afford with the 15-year mortgage.


You pay more than three times the interest in the 30-year mortgage scenario.

On the 30-year mortgage, you pay $217K in interest expense, or nearly 50% of your payments. This is $7.2K of interest expense per year on average, a majority of which is paid during the first half of the mortgage. You pay more per month in interest than in principal until you reach month 186 (more than 15 years into the mortgage).

On the 15-year mortgage, you pay $66K in interest (less than 30% of your payments are for interest). This is $4.4K of interest expense per year on average. You only pay more in interest than in principal for the first 6 months of this 15-year mortgage as compared to 186 months on the 30-year.
This is a difference of $151K, money that could be invested and working for you, instead of going down the drain in interest expense.

Key Issue 3: the lack of equity built during the early stages of a 30-year mortgage is restrictive.
This is also one of the key rationales for renting vs. owning. We don’t know what life is going to throw our way. Job opportunities, or even job loss, marriage/divorce, aging parents to care for, etc. While renting provides the most adaptability and flexibility to change, the 15-year mortgage provides a similar advantage vs. the 30-year mortgage.
Let’s say for whatever reason, you need to move after four-years of purchasing a home.

  • With the 15-year mortgage, you will have paid principal of roughly 20% of your mortgage. Combine that with your 20% standard down payment, even with no growth in your home value, you will have material equity in your home available to you.
  • With the 30-year mortgage, you will have paid principal of roughly 6.5% of your mortgage. This highlights the disadvantage of the 30-year mortgage. This means you only have about 1/3rd of the equity as compared to the 15-year mortgage. Side note: if you can’t afford a 20% down payment, you are not ready for home ownership. There are too many “hidden” (intentionally ignored) costs that come with home ownership. If you can’t save appropriately for a down payment, are you going to save properly to fix the A/C, roof, water heater, etc. that will certainly happen at an “inopportune time”.

Key Issue 4: you are tying up key capital that you could put to work for you.
Your personal residence is NOT an investment. Home values have generally kept up with inflation over the long run. Add in maintenance upkeep, taxes, insurance, etc. and your home certainly is not a long-term wealth generating investment. However, the stock market is. The stock market is also extremely easy and inexpensive to diversify unlike your personal residence which is completely location specific with no diversification. It also doesn’t have huge fees and expenses that are associated with home expenses.

The 15-year mortgage scenario from above included a lower down payment of $20.4K (difference between the 15-year and 30-year down payments). Invest that in the stock market for 15 years at a 7% average CAGR (compound annual growth rate), you will have $56.3K at the end of the 15-years.

Oh, also at the end of those 15-years, you will be MORTGAGE FREE. You won’t have an additional 15-years of mortgage payments where you will just start to materially pay down the mortgage balance!

Do yourself a favor, purchase a home you can actually afford and that means a 15-year mortgage at the maximum.