Community//

Jared Kaplan of OppLoans: “You’re never not changing”

First, when I was investing, there was a term we used called the value-edge. This is essentially the value you create for a customer beyond their next best alternative. It is that measurement that we look at with all business decisions because if you don’t have it, you don’t have a product that will win. As […]

The Thrive Global Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.

First, when I was investing, there was a term we used called the value-edge. This is essentially the value you create for a customer beyond their next best alternative. It is that measurement that we look at with all business decisions because if you don’t have it, you don’t have a product that will win.


As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Jared Kaplan CEO of OppLoans.

Jared Kaplan is the Chief Executive Officer of OppLoans, a leading financial technology platform that provides accessible products and a top-rated experience to middle income, credit-challenged consumers.


Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I grew up in the Detroit suburbs alongside an identical twin brother in a household in which both parents worked. My mother was a high-powered consultant and my dad is a doctor. It was a nurturing environment, but our parents instilled in us both a strong work ethic. Having a twin brother also meant constant, healthy competition. We were both passionate about sports and I loved being the underdog and rooting for the underdog. It was fun choosing to be part of a team who wasn’t always on top, because it was that much better when we won. That mentality has been a common theme for me in all aspects of life.

I started my career at Goldman Sachs, and that was a valuable experience because it gave me top-notch training and the opportunity to work alongside the coolest companies in existence. These companies were hardly underdogs, though. I got back to those roots when I moved into private equity and started to work with companies that were the opposite of cutting-edge and needed help innovating.

That’s where I realized that the best opportunities for disruption are usually in the oldest and most mundane industries. During that time, we saw how traditional insurance wasn’t working for small business, so we incubated a startup that I joined to help run. We were a small company working for other small businesses and it felt great. It was along those lines that I was approached by the OppLoans founders about becoming CEO. OppLoans sought to help serve the credit-challenged consumer, which in the traditional financial system is the ultimate underdog. The traditional system goes against them in many ways and we are creating products to be that champion — a champion of financial control. It’s been five years but it feels like we’re just getting started.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

When the founders of OppLoans first approached me five years ago, I was unfamiliar with the non-prime consumer landscape and was admittedly put off by the industry’s negative stigma. I didn’t initially realize there is such a large need for viable alternatives for millions of consumers versus resorting to the limited legacy options of payday loans, title loans and bank overdraft fees.

So, I took a page from my previous life as an investor, where I learned the best question to evaluate any business is this: Do you create material value for your customers above and beyond their next best alternative?

What I realized when researching the opportunity is that non-prime consumers are way too familiar with less than ideal customer experiences. By listening to hours of customer service calls during my interview process, I also heard and saw first-hand how the founders built a really strong customer service organization as well as a thoughtful product that created access to credit for so many consumers who need it.

The founders created a very unique, customer-centric culture that really drove the great experience for the customer. Couple that with a simple, transparent lending product — we had a winning model. I was hooked. Since I joined, we have also implemented a number of consumer guardrails built in — such as a referral system to check into near prime options at the front end for the consumer; ability to repay underwriting models; and a requirement that all payments pay back a portion of the principal, not just interest — to name a few. In the non-prime space, self-imposed protections such as these were new concepts.

What we’re doing today is quantifiably proving that you can rebuild the financial picture for this consumer, give them products and services that will help graduate them back into the traditional financial system.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Sometimes, when businesses start off small and grow rapidly, the facts on the ground can change dramatically over short periods of time. When you’re leading one of these businesses, you’re probably not talking to the whole company about these changes as quickly as they’re happening. As a first-time CEO, I realized the importance of communication and feedback loops — and surprise — people couldn’t read my mind!

For example, early in my tenure with OppLoans, things were changing quickly, while I was addressing the full company every few months, we were growing and how we described the business changed with this growth. I heard an employee describing the company in a way that was no longer accurate and I chimed in. They looked at me quizzically and I realized then that not everyone has the same information set as the CEO, and no, people can’t read minds. It was more of an “aha” moment for me. I needed to set up a better communication infrastructure.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

I’d say my biggest mentors have been my parents — no question about it. Their approach was to work hard, treat employees well, and to truly be there as parents. Sometimes, they came home late and I’d complain to them about it. But they did a great job of being truly present when they were home, and that made a strong impression on me. I try to follow that example with my children. Also, given all the competition I had with my twin brother, there were also plenty of teaching moments from my parents about two wrongs don’t make a right. And your reaction to adversity by taking the high road is paramount, personally and professionally.

When it comes to mentorship in the workplace, I’ve thrived primarily in structures where mentorship isn’t direct — it’s been more sink or swim atmospheres. Through that, I think the most impactful experiences in my career have been ironically, negative ones. What I mean by that is it could be either doing tasks I didn’t enjoy or witnessing behavior I didn’t want to emulate. For every intern class we have, I tell the interns the most important thing is to find out what you don’t want to do or what environment you don’t thrive in. It took me 15 to 20 years to figure that out, I want to help save them some time!

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good?

Frankly, I think that in business, disruption is always healthy. Literally the minute you stop disrupting or looking for a better way is when you start to lose the race, and you get one step closer to getting put out of business by a competitor who is continuing to disrupt.

Groupthink happens all the time across businesses, and the belief in obsolete assumptions exists everywhere. When I was in private equity, we were about to make an investment and about ten people stated their opinions — all in extreme spectrums of agreement. The last person who spoke disagreed and explained it in clear and objective terms.

I deeply respected that person for going against the grain, testing the status quo, and having the confidence and conviction to say something unpopular that might have been right. We need more of that; not less.

When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

You’re never not changing — you aren’t pushing yourself to get better. The minute you even remotely stop changing, you become obsolete. That’s where companies like Amazon, to me, are so impressive. They relentlessly evolve and push themselves to be better and meet the times. Square is similar. These companies have an unquenchable desire to build and disrupt because they know there’s a better way. If we don’t continue to disrupt and get better, there will surely be another OppLoans that puts us out of business.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

When it comes to transforming or disrupting in business, I’d say there are three concepts worth always keeping in mind.

First, when I was investing, there was a term we used called the value-edge. This is essentially the value you create for a customer beyond their next best alternative. It is that measurement that we look at with all business decisions because if you don’t have it, you don’t have a product that will win.

Second, be wary of obsolete assumptions and never be captive of these assumptions. Challenge groupthink, and even if it’s unpopular, listen. It might actually be right.

Finally, waiting for perfect can be the enemy of good. Often, first-mover advantage outweighs the downside of not getting it perfect. You can always move faster and then recalibrate later if needed. I remember at our insurance startup, I was early in my learning to operate at an executive level in a high-growth environment. One example I clearly remember is the CEO and I discussed bringing on a new potential partner and had a meeting to discuss. I said I’d make the call after our meeting. He pointed to the phone and said, “No — Let’s call right now.” I was taken aback, but I learned real-time action can pay off big, and it did.

Lead generation is one of the most important aspects of any business. Can you share some of the strategies you use to generate good, qualified leads?

At OppLoans, this is one of our most unique attributes — we build and control customer acquisition models and strategies for our company. Most companies depend on other companies to acquire for them, particularly at this stage.

In our space, cost of acquisition is really important, so we try to keep that cost low by focusing on organic methods of acquisition and staying laser-focused on the quality of our leads, adjusting on a minute-by-minute basis as we see conversion change through different acquisition channels — all with the goal to pass the savings onto the customer.

We also have strong referrals through partnerships, like Credit Karma and Lending Tree and most importantly through our customers’ testimonials. We have more than 12,000 5-star reviews and an average Google rating of 4.9 out of 5 stars. So, our customer testimonials are one of our strongest ways that customers find us.

We also try to be different. For example, one of our first employees we hired was a comedy writer from Second City because he could bring the boring and mundane content to life. That’s what makes people share content and it’s how we build SEO.

We are sure you aren’t done. How are you going to shake things up next?

To continue to get better, we need to continue to be creative on ways to reach the 60 million credit-challenged consumers and help them build back financial control. As a financial platform, we are very focused on building better ways to help this customer graduate out into traditional products. We want to be their advocate and we have a clear mission to build financial inclusion. Right now, we are exploring new products, new markets, and distribution channels to build credit access for the millions who are locked out of the traditional system.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

There are two books that have been very impactful for me. Delivering Happiness is the story of Zappos. What I love about this book is there’s no level you can’t reach. We consider ourselves the Zappos of non-prime lending. The second is The Hard Thing About Hard Things, which is a book for first-time CEOs and it talks about trade-offs in popularity and wartime versus peacetime generals. There are very good principles in that book I follow daily.

I also try to be a student of others who demonstrate excellence in all walks of life. There are musical performances where we see unbelievable excellence on-stage. I have a folder of links I like to keep bookmarked of artists in absolutely dominant control of their profession or craft. It’s really motivating to watch someone in total control of their gift, with confidence and enthusiasm for what they’re doing.

These include Justin Timberlake and Chris Stapleton performing “Tennessee Whiskey/Drink You Away” as a duet at the 2015 CMA Awards, Cynthia Erivo singing “The Color of Purple” at the Tony Awards in 2016, and Brandy Carlile performing “The Joke” at the 2017 Grammys. When I want motivation to be my best self, I watch these videos.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

It’s not the most creative quote, per se, but “two wrongs don’t make a right” is something I constantly heard growing up as my twin brother and I competed and fought, as siblings often do. We were always pushing each other (and still do!), but the overarching theme instilled by my parents of taking the high road, is critical to who I am today — both as a father and as a leader.

I think disrupting is always a good thing, but overstepping is another. Being conscious of doing right and making sure to take the high road is how leaders can do things right.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I would say I want people to live and think like they can have it all if they put their heart and mind to it. I’m the CEO of a high-growth fintech company and that means I’ve signed up for certain realities. But, I believe I can be a great father and husband at the same time. I saw my parents do it and I know it’s possible. You can be successful and not sacrifice what matters most personally and professionally.

I want to build a great work culture that’s enjoyable, and also high-performing. In investing, I mostly saw two workplaces: the cushy culture that wasn’t overly successful, or the barbaric, miserable culture that yielded great business results. I measure what I’ve built by the attitude of our employees on a Sunday night — how they feel about coming into work on Monday morning.

Maybe it’s not the most profound movement to be starting, but I think demonstrating to the most people possible that you can have it all — and hopefully inspiring a few others to be the same way as a result — is where I’m well-suited to make a difference. It is something I talk to our intern class about each summer. I want to show them by example to build that point of view early on.

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Community//

Thinking About Starting Your Own Company? Don’t Let Anyone Tell You You’re Too Young

by Victoria Kennedy
Community//

Jared Rosenthal of StaffGlass: “Kindness”

by Jason Hartman
Community//

Jared Rosenthal of StaffGlass: “Kindness”

by Jason Remillard
We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.