Dave Grossman Of MilesTalk: 5 Things You Should Do To Become a Thought Leader In Your Industry

An Interview With Abe Alon

Believe it or not, I really look forward to Monday morning — crave it, even. You may ask, how is this possible? Simple: I do what I love, and the opportunity for collaboration with those who harbor the same passion only amplifies my excitement. So, I would say that for other leaders to thrive, they must pursue what they truly enjoy and, ideally, surround themselves with individuals who bring that same energy.

As a part of our series about how to become known as a thought leader in your industry, I had the pleasure of interviewing Dave Grossman.

With a career built over 15 years, Dave Grossman is a leading loyalty program consultant, industry speaker, author and credit card rewards expert. He runs MilesTalk, a blog that explores how to maximize both earning and spending miles and credit card points, and the MilesTalk Facebook group, and is also the mastermind behind the Your Best Credit Cards credit card rewards optimization engine. Dave has written “MilesTalk: Live Your Wildest Travel Dreams Using Miles and Points,” a best-selling guide for building a foundation on how to most effectively earn and spend miles and points.

Thank you so much for doing this with us! Our readers would love to “get to know you” a bit better. Can you share your “backstory” with us?

I officially became an entrepreneur back in the early 2000s after a web development company I had been working for went out of business. After it closed, I couldn’t shake how talented the company’s team had been, and ultimately, I asked them if they would agree to work for me if I could get one of the company’s clients back on board. In the end it all worked out, and for the next 15 years, I ran the web development company with that exceptional team as support.

However, over time, it became clear I did not have a passion for web development, so I took a long, hard look at myself to determine what I really did enjoy… which was travel. From that point on, I entrenched myself in the travel space, really focusing on miles and points which had been a hobby of mine since 2003. It all came to a head in 2016 when I was asked to host a meet-up at SXSW, which was completely oversubscribed, with attendees unwilling to leave when it ended! From there, the MilesTalk blog and Facebook group were born, beginning as a simple hobby and then, in 2019, transforming into my career when I launched the original Your Best Credit Cards website. The Facebook group has experienced significant growth, now with over 30K members. In mid-November 2023, I launched a revamped version of Your Best Credit Cards, a site I had originally created to help take the guesswork out of selecting the best credit card based on the details unique to each person, based on crucial key learnings from the previous version. The revamped site was 17 months in the making and it’s been amazing to see it come to life.

Overall, I have to say that it’s been a fun journey, with success achieved through years of hard work and dedication. It also helps that I love what I do!

Can you briefly share with our readers why you are an authority about the topic of thought leadership?

In a word, obsession. In 2003, due to a mistake made by a hotelthat would have allowed me to book an overwater villa in Bora Bora for almost nothing, I became very active on FlyerTalk, which at that time was really the main source of engagement for those interested in the miles and points world and was simply a bulletin board heavy with threads hundreds of pages along. I was glued to FlyerTalk, but since many experts weren’t willing to spoon feed those who were learning the cat and mouse game of airline and hotel loyalty programs, I started to read absolutely everything I could. At first it was simply to fuel my obsession to know everything there was to know, and then later it was to be that source of support for others. From there, my knowledge of miles and points grew exponentially. It was this approach, this obsession, that made me an authority on credit card rewards and frequent flyer miles — I found the way and practiced it each and every day.

Can you share the most interesting story that happened to you since you started your career?

My pathway to entrepreneurship is quite interesting. To take the ashes of a wonderful, but out of luck, company, reinvent it as a business owner instead of an employee, and turn it it into something that flourished for many years demonstrated to me that becoming an entrepreneur was what I was destined to do. If it weren’t for reviving that client relationship and leveraging an exceptional team as my jumping-off point, I don’t think I would be where I am today. Through the process, I learned a great deal about myself and that I truly thrive when given the opportunity to seek new and better ways of doing things.

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?

In the early days of MilesTalk, I was invited to a Chase card launch event shortly after they introduced what became known as the 5/24 rule, which is now quite well known (essentially, the 5/24 rule states that if a person has been approved for five or more personal credit cards in the past 24 months, they will be ineligible for any Chase credit card product until they get back under the limit.). At the time of the rule coming into play, miles and points enthusiasts were aware of the rule, but it wasn’t something that was discussed. While I was at the event, I began having a great conversation with a Chase executive and asked him about the rule, and with a straight face, the executive said: “What are you talking about?” With that, I began to explain it to him, and eventually, the executive smiled and told me that, of course he knew what it was. I was so embarrassed but grateful that the executive was so gracious!

Ok, thank you for that. Let’s now jump to the main focus of our interview. In a nutshell, how would you define what a ‘Thought Leader’ is? How is a thought leader different from a typical leader? How is a thought leader different from an influencer?

This is an excellent question and essential to really lay out the differentiators. A thought leader knows the industry deep from the inside, can opine about what’s happening, define why things are the way they are and bring insight into the good and the bad, whereas an influencer is really dedicated to selling themselves. Influencers are Subject Matter Experts, as they know how the loyalty programs and miles and points work, but they don’t generally care about the business side — it’s about showcasing how they secured results and inspiring others to emulate them. One isn’t better than the other; they are two different pathways and some people are both!

I do think that I am an interesting case as while I absolutely lean much more towards the thought leadership side, some might argue that I am a bit of an influencer as well, as I do enjoy public speaking on various industry topics (and even the occasional Instagram reel!), which positions me a bit in the spotlight. I’m very driven to understand the ins and outs of what makes loyalty programs both successful and unsuccessful and I always try to analyze every situation from both the side of the customer as well as the side of the product manager and stakeholders.

Can you talk to our readers a bit about the benefits of becoming a thought leader? Why do you think it is worthwhile to invest resources and energy into this?

To be honest, thought leadership is not about investing resources and energy. An industry professional doesn’t become a thought leader on purpose, it’s fully involuntary — you have to love what you do or are naturally good at it. If becoming a thought leader requires a significant investment, you’re doing the wrong thing.

Let’s talk about business opportunities specifically. Can you share a few examples of how thought leadership can help a business grow or create lucrative opportunities?

Obviously, once you are known as an expert (and I prefer that term over thought leader), there is a very distinct snowball effect when it comes to business opportunities. Participating in public speaking opportunities can accelerate this because once an audience sees you on stage, discussing an industry topic that resonates with them or at least applies to their industry, they automatically see you as an expert.

In your opinion, who is an example of someone who has done a fantastic job as a thought leader? Which specific things have impressed you about that person? What lessons can we learn from this person’s approach?

Gary Leff from View from the Wing is a great example of an unshakeable thought leader as he is super smart, has a passion for what he does, is an excellent content producer and has been in the industry for even longer than I have, so he has rock solid insights that many professionals turn to. I am so impressed by his dedication to engagement to being accessible, not just through the content he creates but also through social media — that can take a significant amount of time, and he doesn’t shy away from putting in the work. Another notable thing about Gary, which I think is the mark of any true thought leader, is that he embraces a good debate. He’s never done expanding his knowledge, enabling him to continue to educate others in the industry while embracing that unique quality of humbleness.

I have seen some discussion that the term “thought leader” is trite, overused, and should be avoided. What is your feeling about this?

There is nothing wrong with the term “thought leader;” no need to avoid it. What needs to be understood is that a professional must actually earn the designation “thought leader” vs. simply claiming it. Stamping it on a resume or featuring it on a blog doesn’t make the term come to life, especially if a person is new to the industry. No one wants to look like they are trying too hard, as it weakens the perception of credibility, which is evident when tenure does not yet exist.

What advice would you give to other leaders to thrive and avoid burnout?

Believe it or not, I really look forward to Monday morning — crave it, even. You may ask, how is this possible? Simple: I do what I love, and the opportunity for collaboration with those who harbor the same passion only amplifies my excitement. So, I would say that for other leaders to thrive, they must pursue what they truly enjoy and, ideally, surround themselves with individuals who bring that same energy.

Additionally, it is essential that leaders take vacations. At the beginning of my career, I didn’t take any vacations as I didn’t think I could find the time. A good friend of mine who kept a very busy schedule told me that at the end of the day, I have to make a real effort to schedule vacations and just let people know I will be out. After all, no one is going to advocate for your own vacation like you will, and you just have to put in the effort to make time for yourself in order to make it happen. That said, I confess that I almost never go a day without doing some work, even on vacation, but if you can fully disconnect, you absolutely should!

You are a person of enormous 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. :-)

That’s a tough question. Honestly, the points and miles space is brimming with professionals and organizations working hard to help others and inspire movement, which I am very proud of. I think that across the board, it’s important to note that while not directly focused on helping others, we work with miles and points to enable individuals to have the invaluable experience of travel as it helps deepen the understanding and appreciation of different cultures and people, which can be eye-opening and make a positive effect on our lives. With MilesTalk, I hope that I am able to provide others with that opportunity, especially those who otherwise would be unable to afford to travel to these unique places. That means a lot to me.

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

The quote that I live by, which drives my entrepreneurship and my work ethic, points back to a previous response: “Do what you love.” Even with that first stint as an entrepreneur when I started my web development company, I never felt any real passion but stuck with it because it was the only thing I knew. But with MilesTalk and Your Best Credit Cards, I’ve felt an enjoyment from work that I never thought possible. In fact, my passion for Your Best Credit Cards has inspired me to launch a new version of the site that incorporates all the learnings I’ve had since the initial launch. I’ve been so committed to creating the ultimate user experience there — for beginners and advanced users alike — that it took 17 months to develop!

We are blessed that very prominent leaders in business and entertainment read this column. Is there a person in the world with whom you would like to have lunch or breakfast? He or she might just see this, especially if we tag them. :-)

I’d like to have lunch or breakfast with two professionals. In the credit card world, I’d love to spend some time with Jamie Dimon of Chase because Chase cards are enormously popular in the travel niche, and they also have a huge array of great co-brand partners. . Additionally, I am interested in personal finance, so I’d love to chat with him about the state of the economy, interest rates, etc. Outside of my space, I’d love to have a meal with Gary Vaynerchuk. I find him to be very inspiring as he also loves building his business and approaches his work tirelessly, operating completely nonstop. Like people say about me when I speak on miles and points, he exudes an unparalleled passion for what he does. Gary says to go where the attention is, and that’s advice that any thought leader and/or entrepreneur should keep in mind.

How can our readers further follow your work online?

For the latest in miles and points, be sure to visit the MilesTalk blog, as well as the MilesTalk Facebook group. Your Best Credit Cards, powered by MilesTalk, is of course, a great resource for identifying the right credit card for you. Also, be sure to follow me on X, Instagram and YouTube.

Thank you so much for your insights. This was very insightful and meaningful.