Amid Downturn, Ecommerce Investor Perseveres

The post-Covid ecommerce hangover has hit Roman Kahn. He launched his first direct-to-consumer brand in 2013, acquired others, and in 2021 founded Peak 21, an aggregator with equity investors. The outlook was good.

Fast forward to 2024, and many ecommerce companies are struggling. Mergers and acquisitions have cratered. Yet Kahn perseveres. His team reviews dozens of purchase candidates every month, albeit cautiously.

In our recent conversation, Kahn shared his investment criteria, current market conditions, and predictions for a recovery. The entire audio is embedded below. The transcript is edited for clarity and length.

Eric Bandholz: Give us a rundown of what you do.

Roman Khan: I’m the founder and president of an ecommerce holding company called Peak 21. We buy, grow, and sell direct-to-consumer brands. My DTC experience began in 2013 when my wife, Jennifer, and I started Linjer. We sold leather bags but now it’s mostly jewelry. We launched it on Indiegogo.

By 2016, we were doing a couple of million in annual revenue — big enough for Jennifer and me to quit our jobs to work on it full-time. In 2017, Linjer produced $1 million in EBITDA — earnings before interest, taxes, depreciation, and amortization. By then we had raised quite a bit of money on Kickstarter and Indiegogo and built up street cred. Folks were reaching out, asking us how we did it. We decided to diversify. We needed more brands, and Meta ads were working well.

I took that $1 million of cash, our street cred, and combined sweat equity with cash to invest in three other DTC companies. Each was doing less than $1 million in revenue annually. By 2019, we were doing $50 million in sales as a group.

When Covid hit in 2020, revenue ballooned to $100 million annually. In 2021, investors were knocking on our door, particularly Jeffrey Yan, whose family owned Forbes Media up until this year. He came to my office and said I needed to take on external capital to buy more prominent companies.

We set up a special purpose acquisition company — a blank check company — called Peak 21. Jeffrey Yan and others invested eight figures in equity. We’re now using that SPAC to buy companies. We seek brands doing $5 to $50 million in annual sales.

Bandholz: What’s an ideal acquisition candidate?

Khan: The pool is shrinking. I’ve spoken with many owners. My acquisitions team talks to 100-plus businesses every month. Only about 10% have a product-market fit that can grow with low budgets. Our main criterion now is size. We look at the fundamentals. What’s the customer acquisition cost? And the repeat buyer rate? The best scenario is 70% of first-time buyers repeat in the first quarter. We know the investment will likely work out at the rate.

Two, we look at customers’ buying habits. For instance, we own a company called Nutrition Kitchen. It’s a daily meal delivery service. Daily rather than weekly or monthly habits play a significant role.

Beyond consumables, we look at contribution margins on three levels.

First, we calculate revenue (net of taxes and coupon-driven sales) and shipping fees collected at checkout. That leaves us with “profit contribution one” — PC1.

Then, we deduct roughly 10 variable costs, such as warehouse storage, pick-and-pack, shipping fees, returns, and exchanges. That results in profit contribution two — PC2.

Lastly, we deduct marketing to determine PC3.

From PC3 we subtract operating expenses to arrive at EBITDA.

A key acquisition metric is a 50% or higher PC2 while maintaining a competitive suggested retail price.

Bandholz: A hundred candidates a month is a lot to review.

Roman: Many ecommerce companies are struggling now. Revenue and EBITDA are down. Out of our six main brands, two are struggling massively. Overall we’re okay. We’re growing with a diversified portfolio. But those two are a nightmare. We have lent over $1 million to each one in the last 24 months. So it’s been hard. Many founders are holding out until 2025 or 2026 to sell.

We buy companies in four ways. One is cash. Two is seller financing. Three is using debt, where we borrow the money against the acquired company’s value. That avenue, I should add, is very challenging now. The fourth method is an equity swap wherein we acquire a company with Peak 21 stock. Cash is scarce right now. Our willingness to pay a lot of cash upfront is low to non-existent. We’re often the only real buyers when talking to a company.

For the market to improve, two things need to happen. First, investors must get over the losses from aggregators, such as Perch, Thrasio, and others. Second, interest rates have to come down. Once that happens, liquidity will loosen up, and hopefully, the market will return, likely by Q1 2026 in my estimation.

Bandholz: How can listeners contact you?

Khan: Our site Peak21.io. They can message me on X or on LinkedIn.

Don’t Outsource Revenue, Says Hair Growth Founder

Faraz Kahn began losing his hair at age 21. Years later, when searching for startup business ideas, he focused on his own experience. The result is Fully Vital, a direct-to-consumer seller of hair loss serums and supplements that he launched in 2021.

He and I recently spoke. We addressed his launch of Fully Vital and lessons learned afterward. Relying on agencies and consultants for customer acquisition is among his biggest regrets. “Don’t outsource revenue,” he says.

The entire audio of our conversation is embedded below. The transcript is edited for clarity and length.

Eric Bandholz: Give us a rundown of what you do.

Faraz Khan: I founded an ecommerce business in 2021 called Fully Vital. We make and sell hair wellness products mainly targeted at women over 40. I’ve been losing my hair since I was 21. I tried pharmaceuticals such as finasteride for a decade.

For years, I worked as a web developer and marketer in Los Angeles. In 2019 I decided to change careers and consider opportunities in ecommerce. I focused my search on longevity and being youthful. I started a podcast and interviewed leaders in the longevity field, but I wasn’t making money. So I looked at my own hair loss for ideas.

I researched extensively. Many companies sell stuff. I wanted to offer unique products to a broad audience. I went to international conventions. I flew to Thailand for a conference of hair transplant surgeons and stem cell experts. I learned enough there to realize the key to hair growth is doing many things simultaneously.

Working with physicians and scientists, I developed a serum and supplements for hair growth and density. Then, recently, we launched products for delaying gray hairs. I enlisted my friend Dr. Sandra Kaufmann, who’s written two books on longevity. She designed the protocol for delaying and reversing gray hairs. We now have two product lines.

I was new to ecommerce and didn’t know what I was doing. I’ve made a hundred mistakes, but here we are, still improving. I’ve got friends in the longevity space who are gracious enough to have me on their podcasts. Every time I do an episode, my messaging has gotten better. We discuss the science, how we developed our solution, and our target markets.

Part of my challenge is translating that authenticity into direct response marketing and Facebook ads. Our field requires education because many women, particularly, have tried many things for hair loss. We have to be authentic.

Bandholz: You’re offering subscriptions.

Khan: Yes. We’ve worked on the subscription offer to make it enticing, which involves educating the shopper. Our products take about 90 days to see results because of the hair cycle. With education, subscriptions have increased — about 40% in the last six months. Our goal is to convert 20% of all buyers into subscriptions.

We’ve focused much of our efforts on serum versus supplements because the margins are better. We need good margins to make advertising profitable.

Bandholz: What would you do differently if you could start over?

Khan: My biggest mistake was not focusing on Facebook ads, the cash cow for most direct-to-consumer businesses. I didn’t know Facebook and thought I wasn’t good enough. I’m not creative. I relied on agencies and consultants—with no results for those efforts. Our cost per acquisition exceeded $200, meaning negative margins. Then I went to Affiliate Summit West in Las Vegas and met people profitably spending $10,000 per day on Facebook ads.

That led me to change my outlook. I got into Facebook, owned it, and began editing some of our ads. I learned when to change creative, how many hooks we need, and hurdles in the conversion path. I had to get in the weeds.

I’ve learned our strengths and differences from other sellers. Our messaging has improved. Facebook’s algorithm changes required us to double down on our messaging at every consumer touch point.

We tried TikTok Shop, but nothing moves the needle like Facebook. Now I spend most of my time there. Last fall, I retained an incredible creative strategist. She encouraged me to spend more on Facebook. It’s made a big difference for me to be involved in the details.

Don’t outsource revenue. That’s my advice to entrepreneurs.

Bandholz: Where can people buy your products?

Khan: Our website is FullyVital.com. I’m @FarazKhan1000 on X and @antiaginghacks on Instagram.

Commerce Drives Culture, Says Media CEO

Phillip Jackson launched Future Commerce in 2016. The company produces articles, newsletters, and podcasts focusing on coming trends and developments in business.

He believes commerce produces a gentler society, one that fosters culture and stability. Commerce is culture, he states.

He and I recently discussed his company’s mission, large versus small brands, the maturity of ecommerce, and more. The entire audio of our conversation is embedded below. The transcript is edited for length and clarity.

Eric Bandholz: Who are you?

Phillip Jackson: I am the co-founder and CEO of Future Commerce, a small, bootstrapped business researching and producing media for ecommerce businesses. We work with large and small brands. We’re trying to predict the future of commerce, which was technology for the last 15 or 20 years, but now that every business is technology-enabled, we have to think about the next phase. We have four podcasts: Future Commerce, Infinite Shelf, Step by Step, and Decoded.

Ten years ago, big brands said, “We need to be online,” and “What does direct-to-consumer look like for us?” Let’s say you’re dealing with Mondelez (the food and beverage holding company) or some other conglomerate where you have individual brands with their own innovations teams, futures teams, and P&Ls within the business. They’re all resourced differently, have separate budgets, and are not talking to each other.

Some brands will find a way to achieve breakout success on the sly. You have little scrum teams or individual operating teams that don’t ask for permission—they ask for forgiveness and demonstrate success somewhere within the business. Some of the best innovations occur when they bring in entrepreneurs who understand how to get stuff done. They’re not just about theory, sitting in boardrooms, and figuring out spreadsheets. They’re good at rolling their sleeves up and getting things done.

Bandholz: You talk about an idea that commerce is culture. Can you explain?

Jackson: We’ve been at it with Future Commerce for about eight years. Over the last three or four years, ecommerce has mostly been solved. You can talk about all the tips, tricks, and tactics, but generally, it’s just buying a new piece of software.

The early exciting internet promise based on technology is gone. What has become exciting is going back to the fine arts. When I talk to folks in corporate roles, such as the head of commerce for YouTube or the head of innovation for Visa, they yearn for something deeper. Commerce is a human truth, and independent cultures have all created and found each other through trade routes. The world came together through this necessity of having something others need. Commerce is not just a value exchange — it’s a cultural connection.

We’ve learned that live-streaming isn’t the future of commerce, yet every analyst said it would be because that was happening in Asia. Maybe commerce is more cultural. Every independent culture has its own way of expressing itself, and maybe commerce is one of those. We’ve pared it down to “commerce is culture.” It is who we are at our core. It’s what we value.

A French philosopher believed that commerce makes people more amenable. When you have things you love, prize, and value, you don’t want to lose them. People who have nice things become better actors in society. As a nation becomes richer and attains wealth, it’s less prone to social upheavals. Commerce has a gentle effect on society and gives us the capitalist economy today.

Eric Bandholz: Where can people support you?

Jackson: Visit FutureCommerce.com. Find me on Twitter and LinkedIn.

From Bankrupt to Thriving Entrepreneur

Study a successful entrepreneur, and you’ll likely uncover resilience. Take Aaron Marino. Twenty years ago his first business, a fitness center, failed, leaving him with half a million dollars of debt. Fast-forward to 2024, and Marino is a YouTube celebrity and thriving serial entrepreneur, mainly with men’s grooming products.

He first appeared on the podcast in 2020. We recently caught up. I asked him about failure, success, helping others, and more.

The entire audio of our conversation is embedded below. The transcript is edited for length and clarity.

Eric Bandholz: Tell us about yourself.

Aaron Marino: I’m an entrepreneur at my core. I started posting YouTube videos in 2008 about men’s styles, grooming, dating, and relationships. I called the channel Alpha M, and it took off. I wasn’t that great at it, but I kept doing it.

Over the years, it’s allowed me to start a few businesses and verticals. I have had 20 companies. Most didn’t work out, some worked out a little, and others have done reasonably well. A few years ago, I started a channel called Alpha Mpire, where I interview other entrepreneurs.

Failure was one of the best things for me. I had a fitness center. It was an epic failure. That was my dream from age 12 — to own a fitness center. I shut it down and had half a million dollars in debt. I then drove a beer cart at a country club just to put gas in my car. That was the scariest time of my life. I didn’t have a plan B. The failure forced me to try other things less scary. I was like, okay, what’s the worst thing that can happen? I’m driving a beer cart. I’m broke. I’m bankrupt, but I’m still alive.

Bandholz: How do you emotionally get through bankruptcy as an entrepreneur?

Marino: Stress and anxiety about money and inability to pay bills robbed me of joy like nothing else. I was making a hundred dollars every three weeks driving a beer cart. I was as broke as it got. My credit cards were all shut down. Declaring bankruptcy was a huge emotional relief. It was as if I got a new lease on life. I knew I would never make the same mistakes again. It shaped me in terms of how I think about money and debt. I became more responsible. I recovered and bought a $35,000 car within a year at 100% finance.

I believe there’s a time and a place for loans and debt. If you need it, you need it. A business has two ways to raise money: incur debt or sell equity. The choice depends on how much money and help you need.

Bandholz: You have several businesses now.

Marino: The largest is a men’s skincare company called Tiege Hanley. That was a partnership with two other guys. One of the founders put up $170,000. I generated marketing material through my YouTube channel. We had another founder who also brought equity and technical skills.

I started a hair product business called Pete & Pedro. I did that through white labeling. I started that whole business for $3,000. I went to a friend who was a stylist, and he told me to call people I knew, which began the process.

I started a sunglasses company called Enemy that’s no longer around. I funded it myself. I shut it down because the product was too expensive for what I was charging, leaving no margin for marketing.

I like putting up the money whenever possible. I don’t take substantial wild risks. I don’t need $100,000 to start a business. I can validate many of these businesses for much less.

Bandholz: Tell us about Alpha Mpire, the YouTube channel.

Marino: My original channel, Alpha M., focuses on men’s grooming. I launched it back in 2008. But I love talking about business. I started Alpha Mpire in 2021 to share my experiences and those of other entrepreneurs. I found a renewed passion. With this new channel, there were no expectations. I didn’t have to worry about sponsorships. I could talk about anything. It started to grow. It’s not the biggest channel — around 70,000 subscribers.

The internet has changed the game regarding entrepreneurship and business. It’s like taking a test with the book open. If you want to start a business, the information is out there. It’s never been more affordable.

Everybody has the same access and opportunities. Some people will take action. Most won’t. I tell new entrepreneurs to find somebody who’s done it before. Copy what they did, get their advice or somebody else’s, and then do it yourself. It’s not that hard. If I can do it, anybody can.

Bandholz: Where can people follow you?

Marino: Check out my mastermind community, TheWhiteLabelMpire.com, or my Alpha Mpire YouTube channel.

Painful Decisions Greet First-time CEO

Bryant Jaquez picked a heck of a time to become a CEO. A longtime CMO for direct-to-consumer brands, Jaquez accepted the CEO job early this year for BuddyLove, a Dallas-based women’s apparel company coming off a pandemic-fueled boom and a dismal 2023.

“The overhead and debt service caught up with them,” he told me. “Thus far my job has been a lot of restructuring, evaluating expenses, and making deep cuts — some were painful, such as layoffs.”

He and I recently discussed his journey — from chief marketer to chief executive — including decision-making, stress, compensation, equity stakes, and more.

Our entire audio conversation is embedded below. The transcript is edited for length and clarity.

Eric Bandholz: Give our listeners a recap of who you are.

Bryant Jaquez: I’m a serial CMO turned CEO of BuddyLove, a women’s apparel company based in Dallas, Texas. My background is in direct-to-consumer ecommerce. I’ve worked in the industry for 10 years. Until about seven weeks ago, I led marketing teams. I joined BuddyLove, my first CEO role, in early January.

A CEO at a DTC company must also be an entrepreneur. And I’ve always been entrepreneurial. You have to be obsessed with your work and love it. You must also be ready to take on all the stress and responsibility of running an entire company.

BuddyLove was started in 2010 by a husband-wife team, Buddy and Grayson DeFonso. Grayson designs all of our clothes. Buddy was running the operations but grew tired of it. He approached me and asked if I would be interested in joining the team.

I was ready for a change. There are limitations on how much a CMO can grow professionally. You’re either working towards an exit or trying to increase revenue. I realized that I needed to launch a business myself or run one. So it was good timing.

Bandholz: Is the job what you expected two months in?

Jaquez: BuddyLove hit $14 million in revenue last year — quite a bit smaller than the brands I came from but big enough to have money for fast growth.

BuddyLove is in a similar position to many DTC brands post-pandemic, post-low-interest rates. The company took on a lot of debt. They made some big bets with inventory and cash flow. It worked so long as sales doubled year over year.

Then they had a much slower year in 2023. The overhead and debt service caught up with them. So now we’re cleaning the balance sheet. Our focus is profits and scaling back to a lean company. Thus far my job has involved a lot of restructuring, evaluating expenses, and making deep cuts — some were painful, such as layoffs.

I thought I was good at handling pressure. I jumped on board and started digging into the numbers. I realized we needed to restructure. It took me a couple of weeks to catch my breath.

I’m happy to report that it’s working. We’re rebuilding the brand from the inside out. We’re keeping the soul intact — Grayson’s designs aren’t changing — but we are reimagining how things are run.

Bandholz: How do you earn the team’s trust as the new boss who lays off staff?

Jaquez: The day we did layoffs was one of the hardest of my career. I believe in honesty. I’m a high-care, high-honest communicator. After spending a few days digging into the books, I called the entire team together. I told everybody about the situation. I said, “This is where we’re at. This is the path ahead of us. It’s going to be painful. We have to make cuts. We have to get profitable. We have to spend less than we bring in.”

I tried to lay people off in the manner I would want if the roles were reversed. That included trying to help them find opportunities as quickly as possible. So on that day I posted on X, “These are the positions we let go. Does anybody need these roles?” Within 24 hours, I had opportunities for everyone who wanted them. A few didn’t respond to my attempts to connect them.

We were around 40 employees. Now we’re at about 24.

Bandholz: Many founders want to hire a CEO to grow the company. What does a CEO candidate look for?

Jaquez: For me it’s equity, skin in the game. I took inspiration from Elon Musk’s story of creating out-of-the-money outcomes and structuring an equity agreement to hit them. That’s what we did at BuddyLove. Every time we hit a milestone, it unlocks more equity for me. Right off the bat, I was in a better position than the one I left. So, the simple answer for an entrepreneur is to find out the compensation of the person you’re trying to recruit and make your offer much better.

That’s enough to pique their interest. Then you have to ensure you’re aligned on an exit plan and long-term goals. What kind of a company do you want? What do you sell? Hiring a CEO is one of the riskiest things you can do.

The CEO of a rapidly growing DTC brand likely earns multiple six figures annually plus equity. But here’s what founders need to hear about equity. I had an equity option at my previous employer, apparel brand Caden Lane, that would execute only at the point of a liquidation event. However, the founder was the sole shareholder and controlled when, if ever, that event would occur.

In 2021, she turned down an offer to sell for $100 million. My equity was essentially monopoly money because it didn’t mean anything unless we sold, and I had no control over whether or not we’d sell.

So, founders and CEOs should be aligned on when and how an equity stake can be monetized.

Bandholz: Where can people follow you and buy your clothes?

Jaquez: Shop for women’s apparel at BuddyLove.com. Follow me on X, @BryantJaquez.

Grow or Die, Says Momentum Shake Founder

Mike Tecku first appeared on this podcast in 2019 as an Amazon marketplace seller. Shortly afterward, he sold that business, a maker of floormats. He retired, became bored, and in 2022 launched Momentum, a direct-to-consumer nutritional shake producer. He and I discussed that venture last year in his second appearance.

He’s back. Momentum Shake is flourishing, as is Tecku. He’s evolved from the nuts and bolts of making money to achieving a purpose, building a team, and self-improvement. “If I’m not growing, I’m dying,” he told me.

Our entire audio conversation is embedded below. The transcript is edited for length and clarity.

Eric Bandholz: Your entrepreneurial journey is impressive.

Mike Tecku: Growth gives me meaning and a sense of being alive. If I’m not growing, I’m dying. The American dream of not having to do anything runs counter to human nature. When I retired, I got good at golf. I read many books but could not shake the urge to solve problems. I’d be in a store and think, “This is an interesting product. I wonder if I could make this.”

I got depressed when I wasn’t working on anything. I could feel myself shrinking. About a year into that, I decided I needed to re-embrace being an entrepreneur. That’s just who I am. Those are my gifts. I wanted to use my gifts and strengths, and now I had the privilege of using them in a way that I wanted, not just to survive or make money.

The world is constantly changing. To make something perfect is impossible, but you can pursue it by continually adjusting. The farther you get along, the more precise the destination is, and the more attuned you are to your goal. You gain knowledge and make better decisions. When you’re really into something, you’re continually growing and perfecting your art.

Bandholz: How does a company strive for perfection?

Tecku: You must develop trust with your customers so they know you have their best interest at heart. If we change the flavoring of our shakes, customers worry we’re making it cheaper when the reality is the opposite. You must be transparent with customers and communicate that you want to add more value without increasing their costs. It’s essential to zoom out beyond supply and demand. What advantage can you bring to the market besides making more money?

I want to produce a product 10 times better than everybody for the same price. Most businesses are just media and marketing platforms. They don’t touch the product. If they’re doing anything at all, they’re selling commodities. I want to make something that is a masterpiece and stacks much value into it.

That wasn’t happening with our outsourced manufacturer. I love those people, but they can’t innovate at the speed I want. I can cut costs by 30% when I take over manufacturing. I can shrink cash flow, increase quantity, reduce costs, and improve quality. The only way to do that is through owning the manufacturing process.

Bandholz: What are the pitfalls of in-house manufacturing?

Tecku: The first step is believing it’s doable. I spent 10 years thinking manufacturing was complicated and beyond my expertise. But I had to start questioning myself. Why can’t I assemble a team of intelligent, hardworking individuals? Why can’t I solve those problems?

The goal is to make manufacturing easy. If I can build something simple and scalable, it will be more secure and reliable. I like to forecast five to seven years down the road. What are my goals? I want to scale to a hundred million dollars. What does that look like in the number of units I need to make a day and the machines capable of that?

I’m buying machines to simplify and reduce the chance of error. We can’t eliminate mistakes, but we can streamline processes, steps, and inputs. The machines I’m buying should be able to make a thousand bags an hour with one employee. That’s a scalable system.

Bandholz: You have a single SKU earning thousands of dollars monthly. You’re not touching it. There’s beauty in that.

Tecku: It is beautiful because it frees me for growth and improvement. Recall the old phrase, “Work on your business, not in it.” That can’t change. You have to be on top looking at the pieces. My job is decision-making. I want two hours of hyper-focused thinking every day.

Constantly executing is not the best use of my skills. Some people are way better at it. I consider all components of the business to be assets. The manufacturing facility I’ve been building for the last six months is an asset. I want it to run perfectly without me. That involves the machines, the space, the team — every decision.

Bandholz: I struggle with shifting from the execution role into strategy and decision-making.

Tecku: I try to check with my team to see if they need something from me. I have to remind myself this is what they’re good at and that they appreciate my trust in them. If you want to create independent people who think for themselves, you have to let them fail. My job is to determine the next step. There’s no right path. It requires a lot of walking around, reading books, talking to folks, and paying attention.

Bandholz: Where can folks follow you?

Tecku: Our site is MomentumShake.com. I’m on LinkedIn.

How Merchants Rack-up Airline Points

Allen Walton is the founder of SpyGuy, a seller of surveillance cameras from his base in Texas. He’s also a world traveler and a seasoned acquirer of airline travel points. Ecommerce merchants who pay with a rewards credit card for advertising, shipping, and other expenses can “rack-up crazy points,” he told me.

In our recent interview, his third for this podcast, he elaborated on his methods for obtaining cheap airline tickets and hotel accommodations.

The entire audio of our conversation is embedded below. The transcript is edited for clarity and length.

Eric Bandholz: You are the points guy.

Allen Walton: I’m pretty well-versed. For almost 10 years now, I have been paying attention to points and miles and figuring out how to save money, especially on international travel. Many folks come to me for tips, and I am happy to help because I know how meaningful it is to lay flat on a business seat when you’re on your way to meet suppliers in Asia.

If you desire to travel, whether for business or personal, and you’re willing to learn some rules to redeem those points, you could fly business class from the U.S. to Asia or get just under $400 in cash. There are some tricks. Ideally, you must be flexible about when you fly out or your final destination.

Say you’re trying to get to Barcelona in the summer. There might not be something available that gets you the whole way there, but if you’re happy with ending up in Madrid or Paris, there might be something there that’s just a fraction of the price of trying to get to Barcelona. Flexibility opens up the possibilities.

Bandholz: What’s the process?

Walton: Airlines have loyalty programs. American has the AAdvantage program, United has MileagePlus, and Air France has Flying Blue. You can rack-up airline miles from standard fares and redeem those miles for tickets. You can also get airline miles just by making regular credit card purchases. You don’t have to fly on those airlines to rack up their miles.

“Anytime awards” or “everyday awards” are where you pick the exact flight you want on the same date you want, and the airlines will quote you a price that will typically be expensive in terms of points. On United, it might be 200,000 points from New York to Japan or New York to Hong Kong. But there are what’s called “saver awards.” On many flights, the airlines will designate a small number of seats at a saver rate, which might be much less. So, instead of 200,000 points, it might be 80,000. If you know the game’s rules, you can look for these saver seats, which aren’t on every flight, but you can book these awards at a fraction of the average points.

Bandholz: Do you have to switch credit cards to get the maximum points?

Walton: No. Getting a big signup offer, canceling it, and switch cards to max out the number of points is what somebody with a nine-to-five job might do because they don’t spend the amount of money necessary to facilitate redeeming points for miles. You do not need to do that as an ecommerce entrepreneur. When you factor in ad spend, shipping, SaaS, and paying suppliers, your monthly spend on a credit card is so much that you don’t need to do that game. You could stick with one, two, or maybe even three cards and rack up many points from your regular business expenses.

Bandholz:  What are the best cards for entrepreneurs?

Walton: There are a few for ecommerce entrepreneurs, particularly the American Express Business Gold Card. For the last decade, it was four points for every dollar of online advertising and shipping. That was big for anyone who advertised online or shipped physical products. You could rack up crazy points. AmEx recently tweaked that card. This year, instead of 4-times on shipping, they added 4-times on software and cloud computing. Klaviyo and ClickUp will be on that, for example. The card has a $400 annual fee but pays itself when you get four points for every dollar you spend. You can start redeeming that for business-class international travel or hotel stays.

The Chase Ink Business Preferred is the next option, but getting multiples of this card is much more challenging. Generally, you need a relationship with the small business banker at Chase, such as your local regional banker. This card gives you 3-times points on online ads and 3-times on shipping. It has a $95 annual fee and a 100,000 signup bonus. You could do a round-trip ticket from the U.S. to Europe in business class just from the signup bonus. And so it’s a card worth picking up if you’ve tapped out on AmEx cards.

You might want to consider looking at a hotel card for loyalty reasons. I have platinum status with Marriott Bonvoy because there are a lot of Marriotts. They give you a 4:00 p.m. checkout, an upgrade to suites, and a free breakfast. Sometimes you have to ask. They won’t do it automatically. It makes it a lot easier to get status for when you’re traveling and want a better hotel experience, specifically the late checkout.

Consider getting another card for any spending that doesn’t have a multiplier.

Bandholz: Where do you search plane tickets by point costs?

Walton: There’s a tool now that I love called Seats.aero. It scans the most popular routes every hour or so. It will tell you when the flight takes off, how many seats are available, and booking options. There’s a free version, but the paid version costs $10 a month and is worth it. They have a bot that crawls all the airlines’ websites. It will find what’s available at that saver level, what date it is on, how much the fees are, and how you book. It’ll explain all that right there, but it’s imperfect and doesn’t include every airline. It misses a lot of stuff.

Bandholz: How can folks connect with you?

Walton: My website is SpyGuy.com. My Twitter handle is @allenthird.