Zach Resnick discovered the power of points and miles while looking for ways to travel on a budget in college, and eventually opened 300 credit cards, hitting the high-value sign on bonuses through some creative “manufactured spending.” He was able to travel all over the globe for next to nothing, and after becoming an expert on the ins-and-outs of booking travel, started the company Ascend (formerly FlyFlat) to help travelers save thousands on business and first class flights. Lucky for us, he shared some tips on how those of us (without 300 credit cards) can play the system, too.
Tell us a bit about you and your background and how you got to where you are today.
When I started college, coming off of a year of working abroad, I wanted to do more traveling but I didn’t have any money, and I had a lot to work on with getting both a music and politics degree. So I looked into: what are the best and most effective ways for me to be able to travel for free or for close to free? And then I learned about this whole crazy world of using credit card points and airline miles to be able to do that.
Since credit cards have become a major thing in the United States, there’s been these big sign-up bonuses that credit cards offer, as well as great ongoing awards. One day I stumbled upon a subreddit that’s now really ballooned, called r/churning. It’s the idea that you can literally churn through credit cards, and in this community, it became very clear that while you can earn money from spending on a credit card, the real bonus comes from when you get a new credit card signing bonus.
When I first learned about this, I had to build my credit up for about a year before I could really take advantage of it. And then after that, I applied for as many credit cards as I felt I could reasonably get approved for. From the community, I learned about something called an “app-o-rama,” where you try to apply for as many credit cards at once as possible. So you open different browsers and apply for a bunch at the same time so that they can’t see that you’re applying for them close by, because for them there’s a credit risk if you’re applying for lots of credit cards at once. You want to get them all at the exact same time so you don’t get declined.
It sounds great to have a lot of credit cards and get bonuses, but to actually get the bonus, you have to spend money, and I didn’t have any money. So what did I do? There’s another concept called “manufactured spending,” where you’re effectively spending money that isn’t really yours on the credit card, and then you somehow figure out a way to take the money you spend and get it back to pay off the bill.
Ideally, you do that while making money, but at the very least you don’t want to lose money. So what I did—and what was available to me when I was in college (and I did this for almost 300 credit cards)—is I would go to CVS and buy the maximum daily limit of Visa gift cards, which was $1,000, and you could buy those 500 at a time. And it was, I believe, a $5.95 fee to buy that card, and then it was 35 cents to buy a money order to pay it off.
So I would take the Visa gift cards, which would code as debit cards, and then I’d use a debit card at the post office, and then take a picture of my money order on my banking app and pay off the credit card. So for basically every $1,000 it costs me about $10 or 1%, but a lot of the points that I’m earning (independent of the bonus) have a value of more than one cent. Let’s say I want to spend $10,000 to get three or four sign-up bonuses that will cost me $100, but I’ll get maybe $150 or $200 in points that I can use for my travels. And then, most importantly, I’m getting thousands of dollars worth of bonuses. So I just kept repeating this.
This is all still available to anyone, but what I’ve learned is that not everyone’s brain is like mine, and what seems really fun and easy for me can seem very overwhelming and stressful, and it is very serious, because if you make mistakes, you can go into debt, and you could mess up your credit score. But the rules are pretty straightforward, and while the opportunities are different now, for someone with a lot of time that’s comfortable with this type of thing, there’s still no shortage of great ways that you can get bonuses and do manufactured spending.
There’s a number of people I know where that’s basically how they make money. They figure out a way to not spend $100 to get $100 worth of points—they spend $100 to get $200 or $300 or $400 worth of points. If you think about it, a lot of e-commerce businesses are actually like these types of points businesses, because if you run a really low-margin business that spends a lot on credit cards, very often what you receive in credit card points will be worth a lot more than whatever profits that you make in your business. And because of the very clear IRS tax treatment on points, these are all completely tax free. So you can run an e-commerce business, do 10 million in sales, have 10 million of expenses, and spend however many millions on credit cards. But if you put those on the right card, to earn the maximum amount of points, now you’re earning half million dollars worth of Amex points that you can either directly cash out, sell, or use for travel.
While I’m not as familiar with the ins and outs of how to take advantage of this like I was a decade ago, I think that if you take the right mindset into it, there is no shortage of ways to still find ways to manufacture spend profitably.
And is that how you became interested in flying business?
After earning a certain amount of points, I thought, “OK great, now I get free trips,” and then it was like, “Oh, I have so many points that now the free trips are in business class, and now the trips are business class and at luxury hotels.” And again, it’s not literally free, there’s some taxes and fees. But most of my breaks in college, I would take a trip and pay very little for it. So that started my interests both personally and professionally in travel.
How did that interest develop into Ascend?
While I was in college, I ended up having a consulting business where I helped people use their own points. I wasn’t just working with leisure travelers, I started working more with business owners.
There’s really two parts to getting a lot from points. There’s figuring out how to earn as many as you can, and then there’s figuring out how to get as much as you can from those points. A lot of people focus on the latter, but at the time, there were not that many people that were like, “Hey, as a business, you’re spending $2 million a year on credit cards. The fact that you’re not getting $200,000 worth of free travel from that is a mistake, and I can help you very clearly just get a few new credit cards, adjust your spending, and use it like this.”
It didn’t take me a ton of effort to have a really big impact on people’s businesses. But what I learned is that fundamentally, I wasn’t actually solving someone’s burning problem. So when I figured out how to take advantage of some of this point stuff, I changed my product from a knowledge and consulting product to, “Hey, you know this ticket that you want, I’m going to get it for you cheaper than you could possibly book it yourself with cash, and we’re going to give you a free white-glove concierge service attached to it.” And that’s the genesis of Ascend, and what I hope to be working on for many years and decades to come.
That is so fascinating. So for someone unfamiliar with your business now, what’s your elevator pitch for Ascend?
Ascend is a membership program for frequent travelers and the companies they power. With Ascend you get access to a 24/7 team of travel experts that you can message on WhatsApp anytime to coordinate your flights, hotels, and ground transport. They manage every detail end-to-end and step in when plans change so you don’t have to.
Our concierge team are humans, and AI-powered on the backend. This allows our 55-person global concierge team to average a 22-second response time no matter when you message them. They’re not being aided by AI in terms of what they say; AI is just helping them with everything besides service—for example, evaluating important travel data to understand what an individual client might want for their specific preferences. That’s paired with an approach to booking flights that results in bigger discounts than any other travel agency or travel booking platform. So for people who are regularly traveling in premium cabins, you save a lot of time and money through using us.
It’s a product that speaks to both the cost savings as well as the time and stress and cognitive load savings, and my bigger vision for where travel is heading. The vast majority of travel products, or even high-end products today, are sold through the consumer looking through lots of different options online or through an app. But if you go really, really high end, whether it’s travel or luxury handbags, for many years the dominant way that has been sold has been through a concierge.
I think that’s just a fundamentally better, more enjoyable experience for the consumer. And now with advances in software and AI, we’re able to make it where that concierge model can go kind of down market at better, more affordable rates than ever before possible.
Do you see Ascend eventually expanding beyond just flights?
We’re already beyond flights. A lot of people come to us for our incredible flight deals, but they stay for our concierge service. So one way to think about us is like a really incredible outsourced travel executive assistant. We definitely don’t have as many proprietary ways to get crazy good deals on, let’s say, hotels or rental cars compared to flights, but we can guarantee the best in class discounts with that service, and for the vast majority of people I meet, that is already much cheaper than whatever they’re able to do on their own with a lot less stress.
Do you work with people’s own award balances, or do they just pay you directly?
For our members, every quarter they get a free 30-minute consultation on how to better leverage their miles and points, and we can help them secure seats and hotel stays live on the call.
We used to be in the business of helping people use points for a specific trip and helping them transfer in real time. But it’s a really hard business to make work. What we prefer to do is help people get the absolute best cash rate, and if they want to use points, sometimes I will get on these 30-minute consults and advise them how to use the best self-serve tools out there so that they can more effectively think about points on their own in the future.
Without giving away your secrets, what’s the gist of how you get these huge airline deals?
I can’t talk in too much detail publically, but what I will share is the orientation and business model that allows for this. So if you look at pretty much every travel agency, whether it’s an online travel agency like Expedia or an old-school travel agent, they predominantly make money through service fees, booking fees, commissions, or hidden markups from the airlines.
The problem with those business models is these companies have no incentive to actually save you money. If they save you more money, it’s not like their company makes more, right?
At Ascend we make the vast majority of our profits from sharing in client savings. So we run our concierge business at a small loss today, but we make money when we say get you an insanely good deal from North America to Europe. So if we’re only saving you 5%, we’re basically breaking even on those flights. But if we’re saving you $3,000, we’re probably going to make at least $1,000 of our own. That mindset and orientation of not just accepting whatever the airlines or the middlemen decide to give you, and working really hard to be creative, to get the best deal, is a big part of how we’ve been able to have success, and generally, how we get great fares.
You fly a lot yourself. Do you have an all-time favorite business or first class product?
Of course there’s a lot of subjectivity in this, but what I’d say is that it’s hard to be better than the Gulf or East Asian carriers. They’re just a cut above basically any European, North American, or South American carrier you’re going to find across service and food quality, and even things like operations, although that’s probably more about their airports than the plane operators.
Personally, as someone who really likes Japan and Japanese culture, I’ve been lucky enough to fly first class on both Japan Airlines and All Nippon Airways, and those have been my two favorite flight experiences. If I had to choose, All Nippon Airways First Class is probably my singular favorite flight. Think omakase on board, unlimited incredible sake and champagne, and you get pajamas and a bed where you can very comfortably lie down.
How often do you travel now?
I live in Lisbon, Portugal, and do two or three bigger US trips where I’ll go to at least three cities. A lot of my team is in Asia, so I’ll do one or two trips to Asia over the course of the year, and then a number of smaller jaunts within Europe, probably at least once a month.
A few recent passport stamps?
Madrid, Spain
Kochi, India
Abu Dhabi, UAE
Bormio, Italy
New York City, USA
Favorite airport?
One of the best experiences that I’ve had was the San Francisco Airport, which often ranks as the number one airport in the United States. The Polaris lounge there is just fantastic. I’ve been to most of the Polaris lounges in the United States, and I think that’s the best one.
And then another one of the greatest I’ve flown through is Dubai. What I love most about the Dubai Airport that’s just so cool is they don’t have lounges there; they have floors. So in the Emirates terminals, you have the economy floor, and then business has a floor above, and then first class has a floor above that. And it works, because most of their planes are A380s [which have two floors], so you board those planes directly from the business class floor. I’ve only connected there twice, but I remember the first time I did a workout in a room where there was no one else, and then I took a shower in a beautiful marble shower. It was amazing.
Do you have an airport routine?
For me still, even having experienced it so many times, getting early to a nice business class lounge and getting a wonderful free meal is the best. I try to do that every time.
Any in flight wellness tips?
Timeshifter is an incredible app that I highly recommend to everyone. And there’s another one that’s called FlyKitt, though their AI recommendation about when you should sleep is worse than Timeshifter’s. But what they recommend is supplementing with things like tart cherry powder and omega threes at certain times, and I’ve found that to be really helpful. They also have this cool, minimal, electric-like shock that goes on your calves that you just put on your calf and turn on, and it gives you a ton of benefit in terms of blood circulation.
Drinking electrolytes on board is also really important. Both FlyKitt and Timeshifter recommend wearing blue-light blocker glasses during the day while it’s nighttime in your destination, to help reset your circadian rhythm. Those are the biggest ones.
I also think working out at the airport, if you’re lucky enough to have access to a lounge where there’s a shower, can really just make the plane ride feel that much better. Even if it’s not a super intense workout, finding a soft rug, and doing 10 minutes of yoga versus doing nothing can make a very big difference over the course of a long travel day, especially if you’re taking multiple flights.
Favorite hotels?
So because there are really good ways to use points and get great perks, I love Hyatt properties. If I’m staying at a hotel and it’s not a boutique hotel, I’m gonna go out of my way to stay at a Hyatt. Through not very much credit card spend I’m in one of their higher elite statuses, where there’s often a reasonable chance of a suite upgrade. There are all these really nice perks—I get free suite night certificates just through credit card spend, free breakfast, check-out guaranteed until 4pm, and in general, I just find the service at Hyatts is really nice.
But in terms of really special boutique hotels, QC Terme Bagni Vecchi. I love that place. I’m a big hot springs person. I work very hard and often have trouble turning work off. So having an activity where I can just really disconnect is important for me, and I haven’t found anything as good as being in nature + hot springs.
In the United States I love Ojo Caliente, which is about an hour north of Santa Fe, a wonderful natural hot springs resort. And then for more adventurous, hippie-California, no Wi Fi, no cell service spots to really disconnect and recharge, I love the Orr Hot Springs, and Wilbur Hot Springs, both in the Bay Area.
And then for another once-in-a-lifetime boutique hotel experience, the Hoshinoya in Tokyo is incredible. I mean, being able to get natural, quality mineral springs on the 18th floor in Tokyo is amazing. They drill down like, 2000 meters to get that, because there’s not many natural hot springs in Tokyo. I went right after Japan opened its borders post-Covid, so I was able to stay in their normal room for just $300 a night. It was amazing.
What is your favorite hotel rewards program?
Hyatt by far.
For anyone getting into points and miles, is there a credit card you recommend they start out with?
Short answer: for most of your American readers that have good enough credit to get approved for a Chase Sapphire Reserve, that is probably the best all-around premium credit card. But there is a lot of nuance here and I definitely recommend the beginner’s guide and general takes on miles and points from Ben Schlappig at One Mile at a Time for anyone looking to take a deeper dive and find not just the best card, but perhaps the best card portfolio that works for them.
Do you have a favorite airline rewards program?
The program that I think is most consistently rewarding and easy for people to use is the Aeroplan Air Canada mileage program. One underrated program if you’re willing to do the work and talk to airline agents is Singapore Airlines’ KrisFlyer program. They have so much availability at relatively low mileage rates for Singapore flights, but they’re always waitlisted, so you can’t book it directly. But KrisFlyer is where there’s still a lot of value for those who want to put the work in.
Best in-flight conversation or seat mate that you’ve ever had?
About eight years ago I ended up briefly moving to Jordan, and on the flight there from New York, I sat next to a really wonderful guy who became one of my better friends and business mentors during my time living in Jordan. He showed me all around the country and gave me a bunch of advice, and we just talked about the country and Middle Eastern politics, and I learned a lot from him on that initial flight, and then in many subsequent meetings and hangouts after.
Your dream airplane would have?
A sauna.
Leave a Reply
You must be logged in to post a comment.