Winning Big on the American Dream

This interview is part of the 13th issue of Featuring, a newsletter on the intersection of business and culture. Sign up.


Lindsay Holden believes in the American dream—the idea that every citizen can achieve success and a happy life through hard work. But, as many of us know, hard work alone doesn’t always lead to financial security—or even having enough to cover day-to-day expenses. When Lindsay looked at the financial services available to people, she saw a system that seemed to take advantage of its users, benefitting from overdrawn checking accounts and unpaid credit card bills. State lotteries also take advantage of naive hope, promising big wins and rare follow-throughs.

It’s the latter that gave Lindsay the idea for Long Game, an app that uses prize-linked savings and gamified rewards to encourage users to save money. It takes some of the behaviors and the patterns from the feel-good stuff that comes from spending and encourages users to put that money into savings instead. This is money that could be put towards a new future and, perhaps, a renewed American dream.

We talk to Lindsay about how she got her start and how she is turning savings into hope.

It seems like now more than ever, there is a sense of disillusionment with the concept of the American dream. What’s happening?

I think there’s a lack of personal agency and opportunity that’s directly correlated with the deterioration of the middle class. 70% of Americans have less than a thousand dollars saved and 63% of Americans would not be able to cover an unexpected $500 expense. That’s the country we live in now. No one can seek the American dream because so few people have the financial security to take risks. If you’re too focused on just surviving day-to-day, it’s unlikely you feel like you can really take chances and pursue your dreams.

Despite being incredibly common, not having financial security or financial independence can be demoralizing. Most of us have loved ones, or are ourselves, struggling with money. This limits what we can do and what we can plan for. It’s a very a common problem we hope to help address.

How did you get in entrepreneurship? I started my career in Chemical Engineering and then moved into venture capital. That was when I was exposed, first-hand, to entrepreneurship. I really admired the entrepreneurs. To me, that was the American dream in action; having an idea to improve the world and taking the risk to bring it to fruition. It was powerful and exciting and I wanted to be a part of it.

A few years later, I started a company with two friends. One of my co-founders was an economist, and we were using a unique auction design and behavioral economics to provide a win-win solution to help our customers decide ownership of the new top-level domains, that had recently become available. We did hundreds of millions of dollars in auctions and sold the company in March of 2015. Afterwards, I wanted to start another company that combined my personal passions with the behavioral economics that had worked so well the first time around.

How did Long Game come about?

Financial freedom is something that I really care about. I believe there’s a level of financial security required to take risks, the risks that allow you to follow your dreams, change careers, or start a business. At the same time, saving doesn’t actually feel good. Spending money feels good. Gambling money feels good. With Long Game, we wanted to tie those ideas together with behavioral economics. We want saving to feel good, so along came the idea of idea of prize-linked savings.

Prize-linked savings isn’t new and has been proven popular globally, but it’s new to the U.S. It uses the same tactics as the lottery—inspiring the hope of a big jackpot, but redirecting this behavior to get you to save. The lottery is essentially a 70 billion dollar annual tax on the poor. It’s one of the most egregious regressive systems in the country, purposefully targeting lower income populations. With Long Game, we’re redirecting that money into savings that will benefit our users in the long run.

In Long Game, we give you the chance to win $1M and while you’re trying to win, you’re saving. From those savings, you’re creating your financial security. And hey, you could win a fortune while you’re building your own.

Why don’t more Americans save?

I think the main reason Americans don’t save is because spending is really easy and our society over-values consumerism. Everything is telling you to buy, buy, buy. People are living outside their means and the financial services sector encourages you to do so. Credit card companies allow you to spend more than you make and are happy to charge you high interest on it. Financial services is not about helping customers to achieve their goals any more; it’s about banks and financial institutions filling their pockets.

Additionally, for most people, it’s stressful to think about finances. It’s really not fun and there’s no immediate feel-good to saving money. Long Game is trying to take some of the behaviors and the patterns that give people a rush when spending and encourage them to save that money instead.

So, how does Long Game work?

Basically, you download the Long Game app and then you link it to your checking account. We use that information to create a savings account. When you deposit money into your savings account, you’re rewarded with coins. You can use those coins to play games in the app. Coins accrue over time and the more you save the more coins you get, hence more chances to win money in the games. Aside from coins, your savings earn interest to - 0.1%, you can withdraw at any time, and your savings are FDIC insured.

Right now we have three games, and they’re all similar to lottery games. You might pick six numbers and a power ‘emoji’ and, every Thursday, we do a drawing for a million dollars. Or, there’s a flip game. We’ll be adding new games as we grow.

Where does that money come from? What fuels the prizes?

We get this question a lot. We partner with a bank, so the bank holds the money and pays us for those deposits because we’ve done the work acquiring and managing them. Then we take that money and pay it back to the saver in prizes. Over time, we hope to have more prizes with other partners and find advertising and co-marketing opportunities there.

Who do you see as your customer?

Long Game is built for everyday American millennials, between the ages 20 and 35. And that’s because the interaction is something very familiar — games on your phone. Also, traditionally, that population is not very good at saving and doesn’t think a lot about saving because they value lifestyle, experiences, trips, and those types of expenses and experiences more. The cool thing about Long Game is that you can save for those short-term goals, but still have the chance to potentially win and change your life.

How do you see this impacting the lives of everyday individuals who use it?

I really believe that having just a little bit of money saved allows you to take a little bit more risk in your life. Maybe it gives you that comfort to change careers or start a new business venture. It can be totally freeing. You’ve saved and now you have that independence and can weather life’s financial shocks without going into debt. We want people to feel empowered by that, and grow their savings so they can take care of themselves and their family in the future.

What’s your best piece of advice for someone just beginning to save?

Start small. I think many people are intimidated by saving and therefore just avoid it altogether. If you can even just do a little bit at a time and start saving on a consistent basis, you’ll really be able to grow those savings.

A big part of getting people to save is also getting them to identify as a saver. Talking to your friends, they might think of saving as something that older adults do or something they’ll do at their next job. That next job turned into the job after that and pretty soon you’ve missed out on years of growing your savings. Long Game makes it easier for anyone to be a saver.