Our Favorite Tools For Personal Payments and Cash Flow

May 28, 2019 - John Osbon (3 mins to read)

When it comes to paying for goods and services you have many choices these days. The least attractive (besides the quickly disappearing handwritten check) is physical cash, even for small purchases. Over time it has simply become easier to make purchases without paper or coins. In the post-cash era, new payment providers and startups are fighting to gain users and credibility. That means lots of promotions, free trials and millennial-oriented advertising. Beyond the marketing, here is what we’ve found works best.

Marketshare leaders

Despite all the talk about replacing traditional payment technologies, the major payment systems have only grown in size. Our first favorite is the Visa credit card for two reasons. First, payment with Visa is easy and accepted everywhere (unlike Amex) and second, you earn points that can be used to pay for other things like air travel and hotels. Chase Sapphire Reserve is our go-to.

Visa is a public company and has been around a long time. The broadest alternatives to Visa are Mastercard and Discover. Those three cards annually account for trillions of dollar movement, billions of transactions and tens of millions of cardholders. Despite claims that they are old fashioned or doomed to extinction, the opposite has happened. All three are growing in every way. Amex used to be a clear market winner, but if you travel, especially to Europe, you’ll find it’s not accepted universally. Additionally, Amex customer service is not what it used to be.

Electronic leader

PayPal is our next favorite. PayPal is also a public company, one that came out of nowhere in 1998, grew through its relationship with eBay and now has a major share of the payments market. All you need is a cellphone. Security is assured and the money can move from your bank account or a credit card. PayPal is easy and safe and especially useful for transferring money among family members, friends or anyone who is doing small jobs for you around the house.

Virtual favorite

Our third favorite is LevelUp. Again, you need a phone. LevelUp has many features like “Order Ahead,” “Rewards” and “Find Stores.” LevelUp is not as ubiquitous as Visa or as simple as PayPal. With built-in loyalty features, it’s more convenient for places you visit regularly, especially restaurants. It’s easy and safe and convenient if you don’t want to use a card.


Security is always a concern when you are not using cash. By now the links between these payment systems, your bank and your auto-payment of credit card balances have been tested billions of times. Fidelity is the bank account we use but you can link payment apps to any bank account. Since all these payment systems are interconnected it makes them safe. It also makes them virtually impossible to dislodge if you are a new payment system contender. Barron’s had a good article last week on why this is so.

Security is also the main reason bitcoin has not made any practical use progress since its invention a decade ago. Rife with security shortfalls, bitcoin simply does not work all that well and virtually nobody uses it, except to trade bitcoin.

Make it easy

The point of payment systems is to reduce the amount of time you spend thinking about the movement of your money. It is comforting to know that all funds are in the right place at the right time when it comes to expenses and bills. The many auto-pay features embedded in these systems ensure you never incur interest charges.

Let us know if you have any other favorites or would like clarification on how we have optimized our own payment systems.



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