RewardStock review: Did Mark Cuban throw his money down the drain?

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Award travel is an amazing thing, but it's not easy. Regular readers of this site know that it takes time to learn the ins and outs of various reward programs, and you can never really know all of it.

There are some services out there that claim to be able to help, one called RewardStock that attempts to guide you through the process of earning travel rewards while automating much of the redemption process. In fact, it recently received a lot of publicity after appearing on the reality television show Shark Tank, which resulted in a $320,000 investment from Mark Cuban. But is this all it's cracked up to be? Can you really rely on the site to remove this complexity and allow even the most inexperienced traveler to book fantastic award tickets?

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In short, no and no. Let's dive in to see where the site comes up short.

Related: Best starter rewards credit cards of 2020

How RewardStock works

RewardStock is a website that offers free information on reward deals and provides tips on how to earn and spend points. But it also offers a membership for $29 per year that purports to include the following features:

• Algorithm-powered award flight search results
• Expert-assisted reward bookings (for a $10 fee)
• Strategic rewards earning guidance
• Customizable parameters for your situation

Once you've created an account, you now have several tasks necessary to receive customized results. First, you can fill in your account settings, which are fairly limited. You're simply asked what your home airport is, how much you spend each month and if you are eligible for business credit cards. You're also asked how many credit cards you are comfortable opening in the next 12 months.

You can then create travel plans by selecting your home airport and your preferred destination. The system will try to suggest some award travel options, though you'll also want to enter your balances in various reward programs. Unfortunately, you must enter them one-by-one, and they have to be manually updated. Unlike other services out there, there's no way to link your username and password information.

Finally, you can enter the credit cards you currently hold. Just like with your loyalty programs, there's no way to link your card accounts to RewardStock. It will then suggest how much you should spend on each card, as a percentage of your total monthly spending. It will also offer you recommendations for new cards.

RewardBoost

One option that's included with your RewardStock membership is called RewardBoost. This feature is designed to automate your research into new credit cards and even apply for them for you. Using this option requires you to enter your personal information, your financial qualifications and even your business details and will then attempt to determine the ideal card for you.

However, I found RewardStock recommending credit cards to me before I entered any details at all, and there was no mention of the various issuers' application restrictions. All of this left me to question the quality of its customized recommendations.

My experiences

Because it costs $29 to join RewardStock and there's no free trial period offered, I decided to sign up so I could share my observations. The first thing I noticed was essentially a deal-breaker. Not only is this service limited to residents of the United States; it also only supports 35 points of origin and 30 destinations. Is your home airport Tampa (TPA), Milwaukee (MKE) or San Antonio (SAT)? Would you like to book award travel to places like Rio de Janeiro (GIG), Anchorage (ANC) or Miami (MIA)? If so, then you're out of luck.

RewardStock also doesn't help you with hotel awards, although it says that this feature is coming soon. Thankfully, all of this is made very clear before you've forked over your initial payment.

Once I signed up for the paid account and logged in, I was impressed with the well-designed interface. Based on this initial impression, it's no surprise that it did well on the Shark Tank television show. I also like that RewardStock doesn't ask you to enter all of your loyalty program and bank login information. You simply type in your balances and update them manually. While some would likely prefer a higher level of automation, I'd rather not hand out my login information to a start-up in an era when major corporations are announcing cyber-security breaches on a near-daily basis.

But when I started searching for award flights, I noticed a few additional problems, other than the limited coverage noted above.

First, there was little transparency as to what was being searched, and the results didn't show which of my miles would be used. The results also showed little (if any) taxes or fees, which can't possibly be true. For example, I looked for four business-class tickets from Denver to Barcelona, and it found return flights on British Airways, a carrier notorious for imposing tremendous fuel surcharges. Amazingly enough, I was quoted $22.40 in "Travel Taxes & Fees" for four tickets. This wouldn't even begin to cover the numerous government taxes collected by the Spanish and British governments, not to mention the "carrier-imposed surcharge" that British Airways levies on its award bookings, even when booking through partners.

In another example, I looked into booking a flight from Denver to Punta Cana (PUJ) in the Dominican Republic, and was told it would be 25,000 Membership Rewards points and no taxes or fees outside of RewardStock's $10.00 booking fee. There's no frequent flyer program that doesn't add some taxes and fees, and I know that there are significant departure taxes added on by the Dominican Republic.

If I paid with American Express Membership Rewards points, then I could have those points cover the mandatory taxes, but how likely is it that a flight would cost exactly $250.00. Unmentioned was whether or not Rewardstock considered the 35% points rebate offered to me (available on up to 500,000 points per calendar year) when I book through amextravel.com as a holder of The Business Platinum Card® from American Express.

I found that this simplistic view of award booking omitted many of the common tactics used to maximize points and miles. For example, I couldn't find any mention of the Southwest Companion Pass, which can double the value of your miles. The system doesn't appear to take into account if I held United MileagePlus elite status or was a MileagePlus cardholder, which would entitle me to additional saver award space. Is the system aware that Flying Blue isn't displaying Delta's domestic award space? Does it know that you have to call Virgin Atlantic to access the most Delta award space? None of this is clear.

Perhaps these details would be revealed by scheduling a call with RewardStock's booking agents. But when I attempted to pursue this avenue, the next 15-minute appointment was five days from now (and apparently the site doesn't take appointments on Fridays). Of course, any award space you find today may be unavailable in a day or even an hour, so waiting nearly a week for a consultation likely wouldn't help much.

Moving on, I also found some of RewardStock's advice to be suspect. For example, RewardStock offers its own points and miles valuations, which can differ dramatically from TPG's monthly valuations. In some cases, there were even large discrepancies when valuing currencies with nearly-fixed values.

For example, RewardStock lists Southwest Rapid Rewards points as being worth a mere 1.08 cents each, while even a casual member of that frequent flyer program knows that the value is fixed at much closer to 1.5 cents each. RewardStock also lists British Airways Avios as being worth a mere 0.71 cents each, far less than you are easily able to redeem them for (and less than half of TPG's valuation). While there's obviously some subjectivity in determining how much your points and miles are worth, these are some incredibly large discrepancies that (to be blunt) make me question the site's approach.

Summary

So what does this mean for someone looking to use the site?

Pros:

• Polished interface.
• No banking information required.

Cons:

• Limited to use with 35 points of origin and 30 destinations.
• No information about hotel rewards.
• Suspect points valuations.
• Automated systems that can't account for actual knowledge/phone calls.
• Quick to add recommendations, without enough information.
• Phone calls are scheduled five days out.

Conclusions

Ask a doctor if there will ever be an app that replaces the need to see him or her, and you'll likely hear quite a laugh at the thought of condensing a decade or more of training and experience into a series of algorithms. And while I won't begin to compare the skills of an award travel expert to that of a physician, the principle is the same. To earn the most points and miles, and to maximize them effectively, you'll always need to have a nuanced understanding of how each loyalty program works and how it may or may not fit into your travel goals.

While I have to admire the creators of RewardStock for their ambitious attempt to replicate and automate the skills that I've spent a decade acquiring, it's either an impossible task or there's still much work to be done. The developers are obviously talented, but I would have preferred to see them first focus on a much more narrow problem, such as automating the process of searching for airline award seats across multiple programs, while including a lot more transparency. To continue with the medical analogy, it would be more realistic to first create an app that diagnoses a particular disease, instead of attempting to create one that would try to replace all doctors.

Only time will tell if Mark Cuban's investment will pay off in adjusting the slick interface to actually do what the site purports to do. But one thing is for sure right now: this is not a service I'd recommend.

Want to learn more about points and miles? Check out our beginner's guide.