ITF 53 | eCommerce Financial Independence


Today, we’re taking a slightly different route to FI, and lighting the way is serial entrepreneur Connor Gross. Instead of flipping houses, he flips online businesses! He co-founded the Cardly wallet when he was a college freshman. Now, he works full-time on what used to be just side hustles, and he is the co-host of The Next Generation Podcast.

In this episode, Connor weighs in on the two paths of e-commerce: reselling products and creating new products. He goes through the process of starting an online store, sharing some of his strategies for pricing, social responsibility, branding, and platforms like Shopify and Amazon.

So if you’re looking to start a side hustle, this is the episode for you!

Listen to the podcast here


E-commerce Your Way To FI With Connor Gross

Z, how are you doing?

I’m doing good. I was registering all my stuff for the BP Con. Both of us will be there speaking and paneling. I wanted to give a little shout-out to that.

If you guys are not already going to the BiggerPockets Conference, I highly recommend it. I think it is one of the most fun and educational events of 2021. It will be in New Orleans. I know I’m going down a few days early, getting some friends together, and we are going bow fishing. Have you ever heard of that?

No, but is that a type of fish? Are you shooting it with a bow?

Yeah. I have never heard of this, literally. I feel like it is super Southern Louisiana. I’m going to come back with a Southern accent and all that stuff. My friends put it all together, and they have 30 people going. We were going to go and take bows and arrows on a boat and go fishing. I had never done it before, but it is going to be fun. If you guys are thinking about coming down to New Orleans, definitely come down. We would love to see everybody.

I am bunking with Sarah Weaver, who used to be on our show a while back. That will be fun.

It is going to be super fun. All my friends are going to be there and I’m excited about that. Speaking of friends, we got this guy named Connor Gross on our episode. He is a friend of one of my good friends and a fellow Northeastern graduate. He crushed it in the eCommerce business while in college with 5 to 10 hours a week. What did you think about that?

He is crazy. You can tell in certain people’s minds it is the way that they work. I was trying to put myself in his shoes, and like, “There are so many places where I would have been stopped.” I would’ve hit some wall and been like, “Never mind.” I applaud him for going all the way. They were hugely successful and still are, so that is awesome.

He has got a cool story. I find myself doing it. It sounds cool that he is talking about it, but I can’t even imagine trying to deal with vendors, marketing, cost per click, and all that stuff. That is not where my strong suits are, but if you are a marketing person and do like that stuff, it is a very cost-effective way to make a good amount of money.

Let’s bring him on.

Connor Gross, welcome to the show. How are you doing?

What’s up, Craig? I’m doing well. Thanks for having me on the show.

Thanks so much for coming on. We were chatting about your show. When I heard your story, I was like, “We got to get this dude on our show,” because you have got a cool story. It is not real estate, which is a little bit of a curveball but a different twist on financial independence.

I think part of the conversation we had that I have somewhat contrarian takes that people might find a little bit interesting, especially coming from a real estate background for your audience. It definitely would be fun to chat about.

Why don’t we take it back to the moment you first heard about financial independence? Tell us about that moment. How did you hear about it? What happened?

In terms of when I first heard about it, I don’t know if I could necessarily say that it was financially independent was the term I heard right off the bat. I do have a pretty specific moment in my head. I think it was probably in my freshman year of high school growing up. We would always hang out at one of our buddies’ places, have bonfires, hang out, and stuff like that there.

The big thing I noticed is that his parents never seemed to work. I was confused by that. Once you are in high school, you want to start figuring out like, “John’s parents are in manufacturing. So-and-so’s dad is in sales.” These guys were always around, hanging out with the kids and doing their thing. I was like, “How is this possible? How is it that your parents are always around? They are not working. Are they unemployed or something?”

He was like, “They bought a lot of Apple stock back in the ’80s, and now they don’t have to work anymore. They take dividends from that and do their thing.” Once I heard that, I was like, “Okay.” I don’t know stock. I was fourteen years old at that time and I was like, “Let me look into this a little bit more.” You start going down the rabbit hole of how somebody can go and own an asset? How can that asset go and provide returns for them?

ITF 53 | eCommerce Financial Independence
eCommerce Financial Independence: The biggest issue with eCommerce is that, similar to real estate, people just don’t know where to start.


You get to the point where now you are like, “You have some people who go, and all they do is they work 40 hours a week. They do this for 40 years, retire and get Social Security or whatever. They look for these other people who are 35 or 40 years old, who are not working at all because they made their money work for them much earlier on. I started exploring the different options on how to go and follow that path, whether it was stocks or something that was able to go and make me a little bit more money without necessarily correlating to my time. That led me to the whole journey I went on.

A lot of people will be like, “I will buy some Netflix or some Tesla stock because that sounds cool.” How did you go from general speculation to having a game plan?

Is it in terms of investing in stocks?

I don’t know. Did you not go that route? Maybe I should let you unravel your story a little bit further.

The main thing I did right off the bat was in sales and eCommerce. My whole story is a lot of different Amazon, Shopify stores, and things like that where I have been most of my money now. That is the main way I have been earning so far.

How did you go from let’s buy a lot of Apple or Google stock to eCommerce, dropshipping, or whatever it is? Buying stocks is a very antiquated way to invest, whereas the eCommerce thing is a new age. How did you get there?

I guess probably the biggest gap is that when I started exploring all of these different ways that you can go and make money, whether it is real estate, stocks, owning a business, or whatever it is. They all had one thing in mind, which is like, “Their time is not correlated to the money.” I think Warren Buffett has a quote, something along the lines of like, “You will work every day until you die. It let’s you find a way to make money in your sleep.”

Without getting too corny and cliche about it, I wanted to figure out what was that like? It seemed from all the research, whether it was watching YouTube videos or being on Twitter on a daily basis, eCommerce is the gateway drug for entrepreneurship in a weird way. You can start it without much capital. The learning curve is pretty quick. I’m not going to knock on real estate or anything. I will be honest. It is a steep learning curve, I feel like.

Once you are in there, you understand a lot of the terminology, at least for me personally, whereas eCommerce seems a little bit more simple and straightforward. I went out, and freshman year of college started to go and start a couple of different eCommerce brands, and then one of them blew up. It was built around this entire goal of creating assets that I could still take a week or month off, whatever it was. It was still going to be going and producing income for me.

You saw the passive income from it. You saw that the barriers to entry were so low, not a lot of startup capital and learning capital that you need, so why is not everyone going to this eCommerce thing if the barriers of entry are so low, or are they?

First of all, the majority of people in terms of why is everyone not doing this? The majority of people don’t care. I would say it is probably the number one reason. Take away 95% of the population, if not more, and then now you are stuck with the 5% of the population who want to go and get rich. They have the bandwidth, the education that they know how to go and do things. I would honestly say the biggest issue is that, similar to real estate, people don’t know where to start. They say, “I have an idea for a mug or for a hat or sure, whatever it is that I want to go and sell, I have no idea how to go and make these things.”

Maybe I can go and market it to TikTok or something like that. They don’t know how to build a website. I think most people get stuck on that stage zero phase where they are like, “I have this idea. I want to go and make headphones. What do I do next?” I think the big thing is finding how to go and make the product and manufacturer it, whether that is overseas or finding a supplier in the US. I have found that some of the best people that can go and make it in the eCommerce world are the people who are good at sales and figuring things out because they can find the best manufacturers and suppliers to work with.

eCommerce is the gateway drug for entrepreneurship in a weird way. Click To Tweet

It does feel like a big process. You got to find a website and suppliers. You got to price, market, sell and distribute it. It does feel like a lot. Where do you start? I can see why people may get slip up. Let’s say I’m at square zero. I have no idea. I want to get into eCommerce marketing, but I have not done as much of anything on it. What would be my first actionable step to take?

I think it depends on what you want. There are probably two paths that you can go and take. There is the path of, “I want to make money, and I’m willing to sell anything to go and make money.” There is the path of, “No, I have this cool and legendary visionary product in my mind that I need to go and create.” Once I create it, people are going to buy it because it is that good of a product. I think if you are in the first camp, you are like, “I want to sell widgets and sell things online.” It is very simple. You can either go and create a dropshipping store. You can do that on Shopify, connect it up to a platform called AliExpress.

It is as simple as saying, “Fidget spinners are hot right now. I’m going to sell fidget spinners, and they will be the shade of blue.” I think fidget spinners, frankly, is probably a pretty bad example. Your best bet is to try to reverse engineer what keywords are popular right now. You can do that through some different keyword tools. It is about figuring out, “Where’s there a ton of demand and not a lot of supply and figuring out that.” If you don’t have to go down to the dropshipping route, the better option to do would be some print-on-demand store.

I love that you are like, “It is super easy in real estate. That stuff is hard.” It sounds like Chinese. I’m like, “What is this?” I’m curious about what your product ended up being in the end. I have a couple of friends who do eCommerce, and they have always been in the camps of not making anything but reselling stuff. I had some friends who would buy a palette from Target and resell everything on Amazon. I would have friends that would go to places like a Nike outlet, know which Nike is popular right now, and resell them online. That stuff seems simple and researchable, but I’m curious if you create a product or do something in the retail space.

It sounds like what your friends are doing is flipping or arbitrage where they are essentially saying, “The $30 shoes are selling for $60 on eBay, or whatever it is. Let’s do that.” We went over to China and fair point about the learning curve for each. I fully understand and I think maybe I was more willing to get into something new when I first started. Our product was a cell phone accessory. You might have seen these before, where they are usually a promotional item that companies or organizations use. If you put it on the back of your phone case and it can hold credit cards, student IDs, cash, they stick on there like cardholders. When I think about what product we can go and start, that product was ridiculously high margin while we were not necessarily selling it for a lot.

We sell two packs for $10. Each of the products cost us $0.20 to make. Right off the bat, it is almost all margin. On top of that, what we were doing in this space was finding something that already had high demand. We have noticed that a lot of people like this product. It was in high demand, and people were interested in it, but all of the solutions out there were cheap promotional tacky-looking products.

They would have a Lyft logo on it or whatever if Lyft wanted to advertise to our college campus. That was the example I always used because that was the one I remember the most. What we decided to do is say, “Let’s go and take a popular product and make it slightly better.” We noticed girls are out here spending $40 or $50 on phone cases because they liked the design or aesthetic, but then they go and cover it up with an ugly-looking phone wallet. When we went and created the product, it was essentially a cool Windows populous product. Instead of making it a promotional item that companies are using, let’s go and put a dollar on it, a marble design or something like that in order to go and have them start selling a little bit better.

You said you had sold that thing for $10. Is there a price range that you want to stay in between or you don’t want to go too high because then, if the product sucks, people will return it? If you buy something that is $10, no one is going to return a $10 item. It is not even worth going to the store for. Was that part of your strategy at all?

Honestly, I regret selling a $10 product to some degree. When I say regret, I don’t regret it that much. We sold hundreds of thousands of these products. It worked and was successful. If I could go back and do it over again, I think I would much rather prefer selling $20 to $30 products. The reason for that being is I have looked at a lot of pricing studies and analyses. A lot of them all said that once you get over that $30-mark is when people care. If you sell at $24 or $26 product, or whatever it is, people tend not to think too much of it. I do think that there is a range for that as well.

ITF 53 | eCommerce Financial Independence
eCommerce Financial Independence: There are two things you can do. You can either tap into existing demand or you can try to go and create demand for it.


If you were going to go and start off and your goal is I want to sell a lot of one thing, probably pricing that $20 to $30 range and see how much value you can get for that. The other side of that scale then becomes, “Should I be selling this $50 or $60 on a product?” You are at a point where, “I’m not making a ton of money from this,” but people still care enough to go and make a fuss about getting their money back. If anything goes wrong, they are going to be pissed off. The other side of this then tries to find something if you are going to sell it for a little bit on the higher side, over $100 as well. I think that the $30 to $100 range can be a graveyard if you don’t price it right.

I feel like I’m sure there are loads and loads of studies on pricing. Z, is there anything you want to add?

I’m curious if you ever consider end-use. I feel like this is maybe stupid to say, but because you are young, I feel like maybe you wouldn’t think of that. You are thinking like, “I’m making products and they are cheap.” What I don’t like about cheap crap is that people throw it away. They are like, “What’s the end-use? How are you going to dispose of it? Will all of this end up in the landfill one day, especially with something like cell phones that change all the time?” I don’t know if that has ever come up for you now. I have probably burst your bubble a little.

No, you are all good. From an environmental impact, I would say that compared to most products, which are big and bulky, the worst-case scenario is they do end up in a landfill. I’m not saying this makes it much better, but if it is the size of a credit card versus even smaller than a phone case, by a long shot. Truthfully, I would say from an environmental standpoint, we didn’t pay much mind to it. We reduced some packaging waste and stuff like that. We made the packaging thinner and sleeker.

People are not taking part in this big box. It is this little plastic sleeve that they can go and toss out versus all this cardboard. I would say we did stuff there, but from an end-user, I would not say that we did focus a lot on the product design and did a ton of iterations there. This might sound like a stupid example, but it was an example of something that we noticed in college.

You guys probably see this all the time, or maybe not now if you are a little bit removed, but college students would very frequently carry on like a Juul or something like that with them. We redesigned one version of the product to go and hold one of those. We went through a whole thing, got into a lawsuit with Juul and stuff like that. It was a very long and complicated story, but we were constantly making different product iterations to try to go and serve the end-user based on what they wanted.

It sounds like you thought of it. I appreciate that you are considering packaging and all that stuff.

That is why all the trees are behind, Z. She is going to go and give them all hugs after. I’m nothing against Z, but we were all pro-environment here. Connor, you started this whole credit card business thing. Let’s say they want to do that first option you gave where they don’t have this grand product in mind. They want to make some extra money on the side. Let’s say they find what product they want and sell it in between that $20 and $30 price range. What is the next step for someone to go ahead and do that?

I think there are two points then there again. You are like, “I now have this product. Everyone is going to buy it. Not just my mom making my first sale or something like that. It is going to be a big hit.” There are two things you can do. You can either tap into existing demand or try to go and create demand for it. If you invented this brand-new product, people have never heard of it before, you have to go and educate them about it, now it is going to be time to go and create a ton of different outbound ads to try to go and teach people what this product is and why they need it. That is going to be a lot of creating a Shopify store.

It is easy to have a fourteen-day free trial, and it is $30 a month. You can buy a ton of different themes, set up your Shopify sites, look nice, put your product on there, etc., and then start running hats there. That is probably a little bit of a harder way, but it is probably one of the better ways to do it long-term because you are able to build up a brand. It is tough to go and do some of this performance-driven marketing where it is like, “I have to go and sell the product cheaper than what it is costing me to go and acquire a user for.” Once you get that down and you are able to start building a brand, there is no better way to do it than on a Shopify store.

The counter-argument to that is the Amazon FBA route, which FBA stands for Fulfillment by Amazon. What you do there is you realize, “There is a ton of tools out there like Jungle Scout, Helium 10, and Sellics.” There is a couple of other Amazon keyword tools out there. You can go and research saying like, “Millions of people are out there searching king mattress and bed linens,” or whatever the product is that you want to sell.

Once you are able to go and figure out that if there is high demand there, the suppliers, the manufacturers, and the products available in this space are not that good, you want to go and focus on all the keywords to listings and create that Amazon listing and trying to go and drive traffic to that page. That is the exciting part. Unlike Facebook, Shopify, or anything like that, you don’t have to go and acquire those customers. They are often already on Amazon looking for a product like yours.

Let’s say I’m going to sell bedsheets. I know I want to sell bedsheets. I have looked at the keywords and created my site. People are going to my site and buying my bedsheets, but I still don’t have the bedsheets to give them. How do you get the bedsheets?

It's definitely a scary thing to go and place a bet on yourself early on. You have to be really confident. Click To Tweet

I think that is called fraud in terms of how you get the bedsheets. I don’t do a ton of dropshipping stuff. There are probably other people out there that are better than me. Essentially, the main site, if you are trying to go and source them overseas, is probably either or You can spend the rest of your life digging through suppliers and trying to find the perfect manufacturer for this, or go on each of these sites and spend one hour. There is a section on both of these sites called an RFQ, which means Request for Quotation.

You essentially put in all of the product specs and everything that you want to go and include in your product and say, “I want 36×72-inch bedsheets for a king bed, this thread count, colors, branding or packaging, or whatever that included on it.” You go and post that out there. It is almost similar to social media or tweeting, where you put things out, and other people can go and respond to it.

All manufacturers who search for those keywords, specialize in that industry, whether by that textile or area, will now go and reply to you with a product catalog, their contact information, etc. Usually, the best process is like, “Let me go and get samples. I will pay you for the samples or whatever.” Test out all the product quality and make iterations based on what you need. You go and start ordering some of the final samples and units.

To catch everybody up where we are right now, this process basically is you find a product that you want to sell ideally into the $20 to $30 price range. You then source the product. You are either making it yourself somehow or sourcing it via Alibaba or whatever other sites you mentioned. You get samples and would probably buy thousands of that product. You store them in an Amazon warehouse or whatever. You do the Fulfillment by Amazon or distribute yourself, whatever way you want to do. Is that sum up that entire process, or is it more complex than that?

There is definitely more nuance here and there. I don’t want to make it seem like, “This is a process.” The hardest part undeniably is probably convincing customers of why they should go and shop with you versus someone else. I think from a marketing standpoint, if you are on Amazon, you want to have fantastic product photos, videos, descriptions and show why you are better than some of the other competitors. If you are not selling on Amazon or a similar concept, you need to have an eye-catching Facebook ad. Go and find influencers and affiliates to go and work with. Maybe you get some press or things like that.

Why would you not sell on Amazon? It seems like it would be the obvious choice.

You don’t own your own customer is essentially what it comes down to. I have a brand on Shopify in the automotive space. It is great because we sell a lot on a daily basis. We have an email list now of 10,000 plus and a text message list of thousands of phone numbers. Here is what happens. The worst-case scenario is maybe we violate some huge issue that Shopify has, which I don’t think ever happens, but let’s say it does.

We have 10,000 emails, a brand, and phone numbers. We are able to go and still sell to these customers as we launch new products in the future. One of the scariest parts about running an Amazon business is selling thousands of products a day. It got to the point where if Amazon says we violate their terms of service, or God forbid, launches an Amazon basic version of our product tomorrow, there is nothing we can do. They can kick us off the platform and de-rank us.

We didn’t own a single email address. Nobody knew our brand. When shopping on Amazon, you are looking for commodities and items. Nobody is typing in the brand name on Amazon. They are typing in running shoes, not Nike. I think that was a big concern. That is why you don’t want to sell on Amazon right away.

I’m guessing they probably fork you with fees too.

They can be bad. It is essentially a 15% seller fee and then a 15% purchase price. If you sell a $100 product, it’s $15 plus the 15% of whatever else, but they are not as bad as you would think. They were especially selling a small product as they had by far the best rate in carrying fees that we could have found. We had 3PL, which stands for Third-Party Logistics providers that basically pick and pack all of the products giving us quotes. They are like, “This is 50% off the retail price,” and Amazon was still coming in at half of their quotes. They were definitely the best by far for that.

What makes something a hit for you? Is there a certain amount of volume you need or something that has happened before, where you are like, “I think we need to reiterate this or change it around and drop this product?”

Do you mean by a product standpoint or from a company standpoint?

It is the product because you are probably coming up with new products and changing the products based on if it is selling or not.

When we sold the business in 2020, we had probably about 60 to 70 different SKUs, a fancy word for items. One of the big things that you will realize, whether it is a retailer or, honestly, most things in life, is this Pareto principle, which is 20% of the things impact 80% of the results. That is very much so true in retail as well. I think it would be very hard to find any company out there that has very even sales throughout all of their products.

ITF 53 | eCommerce Financial Independence
eCommerce Financial Independence: The goal right now is to buy and start as many eCommerce and media brands as possible over the next couple of years.


For us, out of the 60 to 70 different products we had, I would say probably 6 to 8 of them made up 80% of our sales. Anytime we would go and launch a new product, it was nice for us because we had a pretty cheap cost of these orders. It was pretty inexpensive to go and start one of these. We could take these kinds of risks, but eventually, every now and then, we would come up with a design or a new product that would be a total hit, and customers would love it and fall into that 80% of the sales category.

I’m wondering about coming up with 60 to 70 products. How many people did you gather? Is it you and one other dude in a basement? I’m curious about this.

I have a partner, Geo, who I have been working with for years now at this point. We met in college. We would go back and forth and brainstorm for hours a day and all kinds of stuff. Honestly, from a design standpoint, that is where a lot of the iterations on our products came from. The audience was 83% female. Frankly, I do not have the eye to know what a girl wants when it comes to a design standpoint.

Frequently, we would go and have our VA find the top-selling phone cases and laptop cases by design, throw them into a spreadsheet, and send that spreadsheet to all of our friends or girlfriends at that time and say, “Can you say which of these that you guys would buy, out of your pocket, if it were on our products?” We would take all of those, prioritize and send them over to manufacturers to get our design made up.

You are doing focus groups, but probably for free.

It is pretty much, yeah.

How much did this take to startup? If I’m at ground zero, how much money and time investment would you say is needed to sell my first product?

I would say if you are going out into the dropshipping route, it is super inexpensive. A couple of hundred dollars, get the software and site set up. It is all out there. If you are private labeling, which is a fancy way of saying creating your own product and holding inventory, it can get more expensive. You are paying for that inventory before you are getting any sales from it. From our standpoint, because we were selling these $0.20 products essentially, we can go and order 1,000 of them for $200 and test the grounds for it. I think we ended up each putting in $400 or $500 between getting the products, the product’s photography, software, all that stuff.

How much of this stuff did you get left with? Do you have boxes and boxes of random stuff hanging around?

We don’t have any. We sold the business last January 2020. Honestly, it was great timing with the pandemic and everything. I definitely feel lucky for that standpoint, but we sold all the inventory with it as well. We sell it for essentially what we paid for it.

You mentioned dropshipping first and white labeling. Can you give us a clear explanation or definition of each of those? What is the difference?

When you are running an eCommerce business, it can suck from a cashflow standpoint. If we bought 1,000 products, we paid for those 1,000 products. The bank account is negative, theoretically, if you are starting with that or it is at zero. What we have to go and do is we have to go and skim 1,000 customers to go and buy those products from us, but they buy them one by one, despite the fact that we paid for the 1,000 upfront. It puts you in this very cash restraint position because by about halfway through selling all of those 1,000, you are like, “We made our money back. These next 500 are going to be profit.”

You also realize, “If I want to keep selling after these next 500, I have to go now and order 1,500. My demand is picking up.” All the money you are making, again, is going back out the door to go and buy another 1,500 products. You are selling more, making a lot of money, but always cashflow negative in a weird way. Dropshipping reverses that model. Dropshipping says, “Here is what we are going to do before we go and buy 1,000 of these products. We are going to go and see if anyone even wants one.”

If I have a candle that I want to go and sell, I’m going to go and list this candle online. If someone is going to come on and send me $20 or $30 and buy my candle, what I’m going to do is never hold the inventory. I’m going to go and tell my manufacturer who is good at manufacturing candles, “John over in Illinois wants to go and buy a candle and ship it directly to him. I don’t want to touch and see it. I will pay you $10 to go and do all that.” I get to go and keep what is the difference.

There are a lot of barriers to entry in eCommerce. You just don't really think about it once you've been in there so long. Click To Tweet

Dropshipping basically goes and keeps it that way. You are never holding the inventory and cashflow positive from day one. The downside of this is that you don’t necessarily get to have as much quality control. You have to do a little bit more upfront work to vet that manufacturer and make sure that they are sending good products because the shipping and returns can be a little bit of a logistical headache.

Private labeling is essentially when you go and do what I originally described where it is like, “I want to sell this microphone, call it Blue Yeti, and market it as such.” That is where you are able to go and build a little bit more of a brand in the space by creating your own brand, putting in all the products, marking it up, and all that stuff.

If I were in your shoes, starting out with zero money, it feels like dropshipping is the way to go. A little bit more of a pain in the event there is a return, but it seems like less money in, and holding inventory seems like a huge pain.

Especially if you are cash-tight, I would say that that is probably the better way to go.

Before I got into real estate, I was looking at side hustles and all this stuff, and the eCommerce thing was something that fell on my plate. I was this close to buying $5,000 worth of water filters, those life straws. I went on to Alibaba and found a bunch of manufacturers that did all the stuff. They asked me for $5,000, and I was scared to give them $5,000, especially at that point in my life. I never ended up doing it, but I almost did it.

It is a pretty scary thing to go and take a bet on yourself early on. You have to be confident. I think the craziest part about when we started this business was that we didn’t think we were going to sell these online. I don’t know what we were thinking as freshmen in college. We were like, “We are going to work 1,000 or 2,000 of these things and sell them around campus.” We flip a couple here and there. We got through 60 of them through our friends at Northeastern and were like, “What do we do with the other 1,900 of these things?” We started going down all the rabbit holes, like, “Should we sell this on Etsy or Amazon? What do we do?” I finally realized we did $30,000 in sales the first year on Amazon or whatever. I’m like, “There might be something here with this Amazon thing.”

I’m wondering if you are willing to talk about the trajectory money-wise of the business? How much do you start with? I know you guys talked about that a little bit. How much you were making and then when you sold and what’s next?

I can give the whole background there because that is probably pretty helpful. I can’t say the sale price of the business, but based on some of the numbers, you can guesstimate based on multiples and stuff like that. That first year we put up is about $1,000. The freshmen in college didn’t have a ton of money, so this is a cheap and easy product to start selling. I think at the end of that first day, we made about $30,000 in sales. It was off one product line on Amazon, starting to figure it out. The next year we’re going into it with a little bit more confidence, like $30,000. That’s a ton of money at the time. We can probably take this to the next level. We started wrapping things up, coming out with two extra products. I think we did about $150,000 that second year.

Is this sales or profit?

This is sales. I think we operated around at a 30% profit margin. The issue is the bank account never reflected it because you’re constantly putting that money back into new inventory and testing out new things. We’re making money but never keeping it until the very end. By the end of that second year, Greg, obviously, at Northeastern, we had the co-op system. I’m talking to my buddy, Geo, my partner at the time. I was like, “Should we try to do this as a co-op? We’re making a decent amount of money. It’s probably better than the $15,000 you’d be making over at state street.”

He’s like, “Yeah, sure. Let’s give it a shot.” We pushed the co-op office to let us go on co-op for this. Finally, they budged. We went on a co-op and right away got to work. This is something that we were doing 5 to 10 hours a week on the side prior to this. You’ve got two guys spending 50 hours each going on it the entire week. From that year, we went from about $150,000 to $850,000 by the end of the year.

I want you to explain to me and the others that don’t know what co-op is. What is happening there?

Co-op is a fancy word for an internship. All it is Northeastern is either a 4- or 5-year school. They are big selling profits that they work with a ton of different companies to go and get you an internship, not during the summer and not after college, but six months paid during college. My first one, I worked six months at a tech company, and you can bounce around and not have to be in classes during that time, which is pretty nice.

They teach you how to be corporate slaves during co-op, and then you guys seem to have broken the system by figuring out an entrepreneurship co-op.

This is maybe a side story. I don’t want to get too distracted, but originally, they were like, “No, you can’t do a co-op for yourself.” I was like, “We are making some money. We are not going to goof off. I promise you.” They are giving us all these hoops to jump through. Finally, this might sound a little weird, but I emailed some reporters at Boston, which is a Boston entrepreneurship journal or a magazine. The subject line was like, “Two kids selling $100,000 a year from their dorm rooms.” I was like, “Wouldn’t that make a great headline for an article? Interview me. We can chat about it more on the phone.”

They put out this whole piece on us. I’m describing how it is working and she was like, “It is so cool that Northeastern supports this. What’s next for you?” I was like, “Northeastern already approved us to go on co-op full-time for the business,” but without them agreeing. She was like, “That’s fantastic,” and wrote that as the last line of the article. Our co-op advisor gave us all this crap to go and have to fill out this paperwork. I sent her the article and said, “All of Boston thinks that we are doing this. It would look dumb if we didn’t go and co-op.” The next email was the Dean CC and like, “You guys are approved. Good luck.” We were like, “Nice.”

That is a testament to the entrepreneurialism in you begging for forgiveness, not permission. Go ahead and do it. What was the worst that can happen? Are you going to get kicked out of school for doing something pretty bad-ass? It was a little different, but every entrepreneur venture is different. I love going against authority, too, especially as a nineteen-year-old kid.

ITF 53 | eCommerce Financial Independence
eCommerce Financial Independence: If they don’t have an email list, start building an email list because then you can start selling sponsorships for that email list.


From our standpoint, we were not duping off. We got an office over on Newbury. We were settling down. In the next couple of months, we are going all-in on this thing and see what we can make of it. It worked. I think we 6X the business or whatever the math comes out to you. We went from $150,000 and finished that year at $850,000. We overhauled our entire supply chain and launched 30 new products. We fixed all of our marketing material.

We got our shit together fast, and it worked. We did it that year. The next year we were like, “What is the goal here? What are we trying to do?” I think the goal for us was like, “We are probably going to do this thing full-time after college, or maybe we will. We are not sure. Let’s go and do a different co-op again.” He worked for an investment bank. I worked at another startup in Boston during that time. Going back to 5 to 10 hours a week of work schedule, the business still grew 50%. I think that in 2020, we went from $850,000 to about $1.2 million in sales.

I’m surprised that you did not drop out of school when you hit that $850,000 mark, and you were making hundreds of thousand dollars right there in six months.

You are going to be on our show, and I realize that this is a bigger trend. Our show is all about interviewing interesting people in their twenties and half, if not more, of all of our guests, have dropped out of school. I had thought about it at one point, truthfully. I still had fun at Northeastern. We were in the frat and went to parties. I like enjoying that part. Even though we were making that money, we were not spending 40 hours a week on a thing. It was not that time-intensive. From our standpoint, we were like, “We can do this on the side, still party during school, and do that whole thing.”

There is something to be said for the college experience too. That was fun. It was four years. Once you graduate, going back to that is tough. You can’t go back to college parties when you graduate college, so that is good for you.

The story wraps up from a financial and what’s next standpoint. We were wrapping up that year and like, “What should we do? Do we want to run this business after college?” I think we both came to the conclusion that we wanted to run a business after college, but not necessarily this one. Overall, we have been doing it for four years and are a little bit bored with the space. It was not as interesting to us anymore. I told you before about the Amazon experience of owning your customer. I will be honest with the idea that Amazon kicking us off their platform for some reason was terrifying and not unheard of. That happens a lot of times. We decided like, “We will list this pretty lofty multiple of EBITDA and stuff like that and figure out what people want.”

If anyone is even interested, I think we listed it for 4 or 5 months in. Canada has got a bunch of tire-kickers. Nobody was super interested in buying or anything like that. Eventually, I got to the point where I was a little frustrated and like, “I’m not super interested in selling anymore.” We got a phone call scheduled for the day after Christmas. Essentially, we were like, “Should I even take this?” I was a little hangover at that point.

I was like, “We are going to go and jump on the call anyway. It is probably worth it.” The buyer was like, “I have bought your product three times before. When I came out to go and buy a business, I was looking for exactly what you guys want, the full asking price. Here you go, I will wire the money this afternoon.” My buddy, Geo, finished up his co-op and investment banking. After the call, he was like, “I have never seen anything like that before.” I’m not sure how to react. We did due diligence for 1 or 2 months and then got the check.

You said two things that I think if you are not in the finance space, you may not quite understand, EBITDA and multiple. Can you maybe explain what those two things are?

EBITDA is honestly a fancy word for profit. I know it stands for Earnings Before Interest, Taxes, Depreciation, and Amortization. It is a fancy word for what you are making before you can go and do any of these other things that can maybe offset your taxes that you are going to be paying for that year. Multiple means whenever you are selling a business, depending on the type of business, it typically sells for multiple.

The reason is that it incentivizes people to go and sell their businesses. As an example, you can have a software business that has a reoccurring revenue. That is typically thought to be pretty safe and well structured, but that will go and sell, depending on the business, anywhere from 6X to 10X multiple.

Another way to think of it is if a lot of your audiences are real estate, a cap rate is essentially the inverse of a multiple. If a cap rate is 5%, that is a 20X multiple of what you are making each year in profit. That is because real estate is thought to be one of the most stable assets that you can go and buy. Whereas in eCommerce, it is typically thought of around a 3X to 4X multiple. It is standard.

Let’s say your EBITDA, profit, or take home is $500,000 a year. The multiple that you are doing is 4X. That means that the purchase price of your company is worth $2 million. That is exactly how it comes. It is super simple math. It is just the words are big.

It is funny. I feel like there are some barriers to entry. The more I’m talking to you guys now, and then going back and explaining some of the terms, I’m like, “There are a lot of barriers to entry in eCommerce. You don’t think about it once you have been in there so long.”

Business and all this stuff are super simple. You don’t have to be a rocket scientist to figure this stuff out. It is a simple addition, subtraction, multiplication, division, and maybe some percentages once in a while. That is all you need to know to be successful at Business Math.

I feel like the hardest part is getting started. An analogy that I heard once, I think it was on a blog. I liked reading and the guy, Tim Urban, talks about anytime you are learning a new skill, whether it is real estate, eCommerce, basketball, or whatever it is, you have to walk into a dark room. It is feeling around where the light switches out. The lights are right there. Where’s the bed or whatever like that. You are trying to start figuring out how things work. Once you know the setup, it is easy to navigate. Growing up, if you are walking around your house at night, you walk through, and you don’t bump into anything because you know exactly where everything is, even without being able to see it. Getting that general layout, in the beginning, is often the toughest part.

I think that is great. Connor, I think we are going to have to head into the final part of the show. Are there any other parting words of wisdom that you want to tell the audience?

No. The only other thing I would say, maybe we can say this at the end anyway, but if anyone does have any questions about this, I’m more than happy to answer or consult or anything like that. I’m more than happy to help.

If you make decisions based on how everyone else is, you're going be miserable. Click To Tweet

I want a quick what’s next? I could see how you could get bored of that space and how a lot of money could make you be like, “I could hang out a little bit,” but you seem super go-getter. I’m curious what you feel excited about. It sounds like it’s not real estate.

Real estate is cool. I do like the real estate stuff, but I think that oftentimes I like the marketing side of running a business a little bit more. Not that you don’t have that with real estate. It is different trying to convince people that they want a certain thing via a Facebook ad than convincing a buyer that they should buy or spend like an entire year in one of your properties.

In terms of what’s next, I get very bored super easily. About a month after selling the business, I was talking about my buddy, Geo, and we were like, “Should we start a tiny house or park, construct a bunch of different tiny houses, buildings or whatever, and start building that.” I’m like, “That for a good week. That was our thing. That is what we are going to do.” That same exact week, I don’t know if it is fate or what, we saw a tiny house blog essentially go up for sale. I don’t know if you guys know how content businesses work, but a lot of the time, you can go and monetize some of these blogs and content sites through display ads and email newsletters.

We don’t have to get all that stuff. We bought a tiny house blog. We are monetizing that through selling building plans, sponsoring a newsletter list, affiliate deals like tiny house furniture, appliances, and all that stuff. If you type in top tiny house appliances, we ranked number one for Google and get a bunch of affiliate deals, so we were building up that business. I bought another business in the eCommerce space, in the photography space too. I am starting another eCommerce brand in the automotive space. My goal right now is to buy and start as many eCommerce and media brands as possible over the next couple of years. I find it fun and bring in operators to help me run them.

It sounds like you purchased a couple of businesses in the heat of COVID. Did you get a discount on those? Was that intentional?

I got a huge discount on the photography one. It was a weird deal where I knew the guy. He had only been running it for a couple of months. It took a little turn, and we got a good deal out of it. The tiny house one was somebody’s project from a few years ago. They honestly forgot about it. It was making them easy money every single month. It’s the same thing, I talked to the guy for a while, but that one wasn’t impacted much from COVID.

This is the whole rabbit hole we can go down, but buying blogs and stuff, maybe there is one last question on that. How do you evaluate a blog or a content provider? How do you approach someone and say, “I want to buy this?”

First of all, a lot of them are already on marketplaces. I will rattle off a bunch of marketplaces that people who are reading can check out., that is a big one.,,, Quiet Light Brokerage, there is probably a half more, but those are quick off the top of my head. They do all the diligence work for you. Empire Flippers is another one where you can go and buy some of this stuff. In terms of how I personally evaluate it if I want to go and buy something, but what you are looking for in a lot of businesses is under-optimized things. The things that I think I can go and do a pretty good job of right off the bat is anything eCommerce related.

With tiny house ones, for example, my goal is to go in, buy that, and then immediately go and start making some tiny house furniture that I can go and sell. I have an email list of 36,000 tiny house owners who all read my content on a weekly basis. On top of that, too, when you are looking for things that are under-optimized or they are only monetizing through Google AdWords or Google AdSense on their website, you can switch that over to a different ad network and basically double the revenue overnight.

If they don’t have an email list, start building an email list because then you can start selling sponsorships for that email list. If they don’t use affiliate links or only use Amazon affiliate links, it means if I say, “Go buy this fridge, and you buy that fridge. I get 2% of that.” A lot of times, if you go through Amazon, it’s 2%. If you go and talk to the fridge company directly, it is 15%. There are a bunch of ways to replace a lot of their affiliate links with more private label ones. Frankly, there is a ton of websites out there right now that get a ton of traffic and aren’t doing a good job at it. We want to go in and roll up a couple of those and flip them.

This is like buying a distressed multifamily property. You buy a distressed property. They are not getting as much rent. Their expenses are too high and their revenue is too low. Reduce the expenses, increase the revenue, increase your net income or your EBITDA, or your net operating income in real estate terms, which will thereby increase the value. You go ahead and flip the site.

That is exactly it, but not only that, you can probably go and get a quick payback in one year, if not quicker than that, especially if you have the right team and operations in place. The most interesting part is even some of the good blogs, the blogs that are not even distressed, the cream of the crop, great real estate, they are selling for 3X multiple. These are typically the blogs that already have a newsletter list and good content. They already have the best ad network, affiliate links and all that stuff set up in place. Even still, you buy this thing, and you are making your money back on a cash-on-cash return basis in three years. It is a different type of asset class that I think more investors will start looking into over the next couple of years. Because it is a website and online, people don’t totally know how to value it now.

Connor, what are you reading right now?

I bought this called Traction. Have you guys ever heard of this?

Yeah. We talked about it with another guest.

ITF 53 | eCommerce Financial Independence

I’m also listening to 50 Cent’s audiobook on Audible because of any of these self-narrated memoirs. The other one that is good is Matthew McConaughey’s GreenLights. I finished that one up, which is awesome.

I have read GreenLights. Traction is obviously good. We use Traction here at The FI Team. I know a lot of entrepreneurs use that entrepreneurial operating system. It is good. Is it his biography? There is one that he wrote with Robert Greene.

That is The 50th Law. It is not that one, which I tweeted this out, and someone said, “If it was that one,” and I said, “No, this one is, Hustle Harder, Hustle Smarter.” Honestly, anytime you can get into the mind of some of these high performance and achiever guys, I love it. Especially when they narrate it, honestly, my probably top three favorite books from a memoir standpoint have been Shoe Dog, Can’t Hurt Me by David Goggins and the Matthew McConaughey GreenLights one. GreenLights, from a book standpoint, I think if I read it, I would probably hate it. The fact that it is Matthew McConaughey’s voice in your ear for eight hours telling you these wild stories. I’m like, “I keep repeating this all day long.”

I literally could not stop listening to that book when I was listening to it too. I will have to check out the Shoe Dog one. Is that Phil Knight narrating it?

I don’t know if that has an Audible, but I would probably put that number one, if not number two book I have ever read.

That has got to be on the list. Second question, what is the best piece of advice you have ever received?

Honestly, I would say it is probably along the lines of how you go and make decisions. I don’t know if I have an exact quote for this. My dad has run his own business for decades. He would point around and be like, “Make whatever decisions you want. I’m not going to tell you how to live your life, but make sure that you are not making decisions based on how other people are making theirs.” I think that is true. It’s an underrated thing that not a lot of people consider. If you make decisions based on how everyone else is, you are going to be somewhat miserable probably.

I don’t know if that is a fact, but if you look around, this is a financial independence show, so much of America is in debt. If it was a health and wellness show, so much of America is not in shape or overweight and eats poorly. If this is a happiness show, there is a huge divorce rate in America. Most people are depressed and addicted to social media on their phones 24/7. I think if you are going to live your life in a certain way, live it however you want. Make sure that you are not living it based on how other people think you should be living it.

If you do things like everyone else, you are going to be like everybody else. If you want to live an extraordinary life, you got to do things a little bit differently.

Connor, number three. What is your why?

Can we clarify this question a little bit more? Is it why I do what I do?

Yeah. What is the driving force behind it?

Honestly, for me, I find it fun, which sounds so nerdy to say. I think from a hobby standpoint, people can say like, “I like fishing or running. I do love traveling and a lot of that stuff,” but I genuinely find it very fun to start and grow businesses. Anytime I do that, it is one of the most fun things for me to do.

That is a good hobby to have. It pays you back.

If you did not get paid to start these businesses, would you still do it?

If they are failing business after business, no, I would get depressed fast. The money definitely helps a lot, but I can tell you right now, especially after this last exit, the money is great. I think anyone who says that it is not lying, but it is fleeting. You are constantly chasing the next high and paycheck. If you do it more because you like figuring out how to go and solve interesting problems, and love working with cool people and creating something that didn’t exist in the world before, then that is 100% the reason why I do it.

That money is a scorecard sometimes. Once you have it, having it is not what makes it fun. It is the measuring of what it does of saying like, “I’m doing good or this is working.” That is the encouragement part.

There is a point. We are saying this, and I’m sure everyone here makes a decent amount of money, but up to a certain range, I think it is $75,000 a year, is what I have read online. I’m not sure if that is the exact number, but something along the lines of after $75,000, most studies show that you are not going to be any happier. You still have people out there who are posting pictures of Lamborghinis and wanting to go and become a billionaire.

Once you cover your base needs, it becomes more about the process and about having fun doing what you're doing and not just adding an extra million dollars to your net worth. Click To Tweet

A lot of it is a scorecard. A lot of people want to go and impress other people, or they want to go and say they did this great thing. I think that once you cover your base needs, it becomes more about the process and having fun doing what you’re doing, not going and trying to add an extra million dollars to your net worth or something like that.

There are multiple communities out there, but there are two big communities. There is the financial independence space, which are people that are more lean fire. They want to have $1 million or $2 million, live off of the 4% rule, $40,000 to $80,000 a year. They are super happy and cushy and can totally live off that lifestyle. They enjoy spending less money. They are bragging about the crappy car they drive and the clothes they wear. I’m honestly like one of those people. I drive a crappy car and am very proud of it.

There is the other side where they also love building businesses. They don’t want to retire. That sounds like the boat you are in where you may hit $1 million, $2 million, or maybe $10 million, but no matter what, you are going to keep growing businesses. It is not about the money. It is because you genuinely enjoy doing that. If, at any point in time, you say, “I don’t want to do this anymore.” You have the ability to stop. I think that is important.

What I hear from you, Craig, is that there is a lifestyle creep and that type that is dangerous too. It is the overworking lifestyle creep where you can get addicted to the creating and let life completely pass you by and miss out on relationships and a bunch of stuff. It is important to be able to have your checks and balances and make sure that you still have a life that does not just work.

That is a great point. If I could add one thing to that, something I started doing that might help people reading, and this is something I started to realize. The amount of work that can be done on a day-to-day basis is not 9:00 to 5:00. It’s theoretically infinite. If I wanted to, I could spend twelve hours going down this rabbit hole and then another twelve hours trying to build up this new site or whatever.

There are theoretically infinite things that I can do. Something I have tried to be way more intentional about is whenever I sit down at my laptop, have you guys heard of this Pomodoro technique? It’s essentially you write down the task, work on it for 25 minutes, and then you have a five-minute break, and then you do another 25-minute task, 5-minute break.

Honestly, the break and the time part doesn’t matter that much. It is specifically about writing, “Here are the 3 to 5 things that I’m going to do and not necessarily spending hours on the internet if it takes me ten hours to go and do these things, great. If it takes me three hours, it is even better. I have more time to go and do whatever else I want to do. I think being a little bit more intentional about that can help a lot.

One thing that I had struggled with in 2020 is I was focused on growing the business and the money aspect of it in the business. I let everything else go. I joined this mastermind that helps me keep me accountable to be a very holistic part of life. They have these 7 or 8 buckets. I’m going to rattle them off quickly so people can hear it. It is health and nutrition, lifestyle and adventure, business and career, financial and investment, spiritual contribution, personal growth and intellectual, friends and family relationships, and the environment. If you can be like a 7 to a 10 in all of those categories, you are going to live an extremely happy life. That is what I have been striving for.

ITF 53 | eCommerce Financial Independence
eCommerce Financial Independence: A common trait of a lot of the high achievers is they all have accountability groups or people that they talk to, that they can bounce ideas off of. It seems to be one of the most common themes.


Side note, I made a comment earlier that most of the people I have chatted with on my podcast have dropped out. I have also noticed that a common trait of a lot of the high achievers is they all have these accountability groups or people that they talk to that they can bounce ideas off of. It seems to be one of the most common things.

If you get first dibs in a bedroom, top bunker, or bottom bunk?

It is a top bunk every day.

You are not afraid of falling off the bed.

No, especially when there is a rail guard.

Connor, where can people find out more about you if they want to learn about the eCommerce space and all that good stuff?

The best two ways to reach me is one on Twitter, @C_Gro, and if you want to listen to me and riff on other ideas and topics and stuff. I also have a podcast called The Next Generation, where we interview successful entrepreneurs in their twenties. Craig is going to be on there. Feel free to go and check out some of the episodes over there.

Connor, thanks so much for coming to the show. This was a good and different episode. It is intriguing to see how someone can start that side hustle and make a couple extra $10,000, $20,000, $30,000 to $100,000 a year on this eCommerce thing. They can decide to either pursue that business or invest in real estate. Whatever you want to do, but it seems like it is a pretty low barrier to entry. Thank you so much for uncovering a lot of that for us. We appreciate it.

Thanks for having me on. It was a blast.

We will talk to you soon.

That was Connor Gross. Z, what did you think?

It is so inspiring. It is crazy to see what people can come up with. When I’m thinking about college, it was a long time ago, but it can be a lot. Thinking of a full college schedule, internship, and then running an entire business and figuring it all out.

He had definitely a full schedule, but I know a lot of people at Northeastern, especially in the fraternities and stuff. Maybe I’m sitting because I was also in one. It seems they always have full schedules. A wise man named Ben Franklin once said, “If you ever want to get something done, ask someone who is busy.” Someone who is busy doesn’t have that free time that creeps into productive time. They are always going to be productive.

I think that is probably what he had following college, and it is crazy. It sounds like he is only able to disclose the amount of money he sold it for. If I had to bet, it would be in the $1 million to $3 million range. They come out splitting $500,000 to $1.5 million paychecks graduated college was a pretty good jumpstart forgetting some other stuff.

I think it is a little bit more than that, but it is impressive.

Before we get off those, it is the top bunk or bottom bunk.

It is bottom bunk. I don’t know. I don’t like heights, first off. I’m tall. Sitting up sometimes, you hit your head. It is not cute. What if you got to pee in the night?

I hate waking up the person below me. I’m like, “Yeah, bottom bunk. I’m going to get up.” I’m with you.

We are older and wiser. He will figure it out.

Any other parting words of wisdom for everybody before we head off?

Let’s hope that everybody books their tickets for BP Con because it would be great to see you guys there. Craig is doing a special house hacking talk. I think it is the same time as mine, a little competition there, but that is okay. They are totally different subjects.

We are going to be counting who is in the audience so he could go hug some trees with Zeona or learn about short-term rentals or whatever it is. Thanks again, guys, so much for reading. If you guys enjoy the show, please leave us a rating and review, a comment, whatever it is. Shoot us a DM on Instagram. Let us know if you like it. It does help. We will see you all next episode.


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