Readers have asked me to do detailed accounts of how I manage to create my moneymaker scenarios. This is a moneymaker deal I did on 7/3/2010 at CVS

I received an email from for a coupon for $4.00 off a $20.00 purchase (if you have a CVS near you, it is well worth the few minutes it takes to sign up as these type of coupons come on a fairly regular basis):

cvs coupon

As soon as I saw that, I immediately went to work to see if I could get $16.00 worth of things for free (or nearly free) so that I could use the last $4.00 to purchase anything I wanted. Here are the basic steps I took:

1. I looked through the CVS weekly advertising circular to see if there were any potential free food items (I want to use food if possible where I am now because there is no tax on it so I can use more of the $4.00 overage toward things I want instead of toward paying tax). On the front page, an ad for buy one get one free Twix and M&M Pretzels caught my eye:

cvs mm ad

2. I went to the Coupon Database an input M&M's Pretzel. I clicked on the link which told me that a coupon for a buy one get one free M&M's pretzel coupon was in the 6/27 RedPlum Sunday coupon insert (I also input Twix which told me that all coupons for Twix had already expired).

3. I went to my shelf where I keep all my coupon inserts:

coupon inserts

4. I pulled the RedPlum 6/27 coupon insert:

redplum 6-27

5. I flipped through the pages and found the coupon on page four:

mm get one free

6. I cut out the coupons from all of the inserts that I had which happened to be 16 (not all shown)

mm coupons

7. I input other deals I saw to see if available coupons would make them free / nearly free. I found a buy one get one free Stayfree tampons ad:

cvs stayfree ad

8. Using the Coupon database again search for “stayfree” told me that there was a buy one get one free Stayfree coupon good up to $4.49 in the same RedPlum 6/27 Sunday coupon insert.

9. Flipping further through the RedPlum coupon insert I found the Stayfree coupon:

stayfree get one free

10. I cut out the coupons from all of the inserts that I had which happened to be 16 (not all shown):

stayfree coupons

11. I did the same steps with “Betty Crocker Warm Delights” (on sale for $0.88) which told me that the 6/27 Smartsource Sunday coupon insert had a $0.75 off 1 coupon, but when I looked in my, I couldn't find the coupon (meaning it must be regional which is always very disappointing). Instead. I printed off two $0.50 off 1 coupons from

betty croker war delights coupon

Note: While this is how you find deals on your own, luckily there is no need for you to do any of this work for CVS since we already list the weekly CVS best deals here on the blog. You can see this week's CVS deal here (7/4 – 7/10).

12. Once I know I can make the deal work, it's simply a matter of figuring out the best deal. Since I want to avoid sales tax, my best scenario is to use at least 9 buy one get one free M&M's Pretzel coupons which will get me 18 candy packages at $0.89 each which equals $16.02 with no tax due. Then I can use $3.98 on anything else to reach the $20 mark so I can use the $4.00 off $20.00 purchase coupon making the $3.98 in whatever I want free.

13. I head to the store with my best case scenario in hand.

14. Upon arriving the first thing I do is scan my CVS card into the self-help machine to see if I get any good coupons. Luck is on my side. I get a $0.50 Extra Bucks coupon meaning I have $0.50 more to spend for free:

cvs extra bucks bonus

15. I look for the M&M's Pretzels. Unfortunately, luck quickly runs out when I find that they are sold out:

pretzel mm sold-out

16. I go to the service counter and ask for a raincheck (this is important because even though I can't use the Pretzel M&M's to help me reach $16.00 this week, the raincheck will allow me to do it in the future if I can find another $4.00 off $20.00 coupon – the manager said there was a limit of 10 for the raincheck and that is why I didn't get 16 for all the coupons I had):

cvs raincheck

17. With no M&M's to get me to $16.00, I check out the prices of Stayfree products (it seems that the shopping gods have determined that I will have to buy tampons to get free food). There are buy one get one free Stayfree maxi pads for $3.99 each. I grab 4 and put them into my basket for a total of $15.96.

18. I add a Betty Crocker Warm Delights (0.88) to make sure I am well above the $16.00 goal.

19. I am down to my last slice of bread and last egg, so I decide to spend the $4.00 to get whole wheat bread and eggs. Unfortunately, eggs turn out not to be an option:

cvs no dairy

20. I add a package of Penne Rigate pasta to replace the eggs I was planning to get.

21. I head to the cash register.

22. I hand the items to the cashier and tell her specifically not to hit total after scanning everything (this is important in this scenario because if the cashier doesn't hit total, then the total individual full prices of all the items I purchased are all added up on the computer ($22.04) which is above $20 allowing me to use my $4.00 off $20.00 coupon. If the cashier hits total on the machine before taking my coupons, the CVS buy one get one free deals and other specials will register bringing the total below $20.00 ($12.06) and the $4.00 off $20.00 coupon won't work)

23. The cashier scans all the items and my CVS card, but does not hit total on the computer. The total reads $22.04. I hand her the $4.00 off $20.00 purchase which scans in without a problem.

24. I give 2 buy one get one free Stayfree coupons which each take another $3.99 off the total.

25. I hand over the $0.50 off 1 Betty Crocker Warm Delights coupon.

26. The cashier hits total and all the CVS deals from the CVS card get input and the total comes to a negative $0.12, but since there is $0.50 in sales tax (the Stayfree pads aren't food), I owe $0.38:

cvs receipt

27. Since I did not have to use the $0.50 Extra Bucks I received in step 14 (and I am calculating a zero sum game with Extra Bucks for this challenge), I actually come out ahead $0.12 (although I need to spend another $0.50 of my total amount I can spend in the challenge in the future at CVS).

28. For getting paid $0.12, I get 4 packages of Stayfree pads (will be donated to charity), 1 loaf of whole wheat bread, 1 package of pasta and 1 brownie bowl:

day 64 cvs

29. Plus I have a raincheck to get 20 M&M's Pretzels free (with coupons) that I can use to create another money maker scenario.

If there is anything that you didn't follow in this scenario, just leave a comment and I will do my best to explain it in even further detail.

This is the current list of food I still have
This is the current list of what I have purchased:

Goal: 100 days eating on $1 a day
Current Money Spent: $39.89
Money Left to Spend: $60.11 ($5.54 must be spent at CVS)
Retail Value of Everything Purchased: $1194.18


The Beginning ::: Day 64: Cooking Is By far The Biggest Challenge


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  1. I don’t know if this is a regional thing but may be something to look into. The local (southern illinois) Dollar Generals have put up big signs announcing that they now accept manufacturer’s and internet coupons and more recently have started print catalinas. I just got a $5 off $20 there. Keep up the good works, bro.

  2. Hi Jeffrey,

    I was just wondering, do you count the donated Stayfree pads in the Penny challenge? I have quite a few things that I will be donating to the womens shelter in the near future. Will I be able to count this in the penny challenge? While it is not a foodbank/pantry, it is still for people in need.

  3. It seems like you would use a lot of ink and paper printing all those coupons. Do you have to throw away / recycle a lot of extra paper or do you have a method for that?

  4. @Tammy

    I do not count the cost of non food items for the Penny Experiment challenge – only food even though I give a lot of non food items to my local food bank which does take these things.

    That being said, I am planning to list a separate number on Penny Experiment of the retail value of all non food items donated to food banks and other charities as well since I (and hopefully all of you) will be donating a lot of this stuff as well.

  5. @Katy

    I don’t use a lot of ink (a t least realtive to what many couponers use)because I only print the coupons that I know I will use. I also print all my coupons in black and white (monochrome setting — I did the one above in color only so you could see the product better) which saves a ton since it is usually the color ink that is most expensive.

  6. WOW. And here I thought that I was rocking the deals getting 2 deodorants, 6 laundry soap, and two brownie bowls for $0.21 net out of pocket…I’ve still got a lot to learn over here! 🙂

  7. I guess I just don’t understand how you can take two buy-one-get-one-free offers, combine them, and then get all of them for free. You’re not actually “buying” any of them.

    Is it just the presence of one of these items on your register gives you a $ amount off? Do all places allow you to combine BOGO offers like this?

  8. @Ryan

    It’s important to remember that you are not costing the store any money in the instance (this is what seems to trip up most people). The only difference is that the manufacturer (through the coupon) is paying the store $3.99 instead of you paying out of your pocket. The store still gets paid the exact same amount whether you pay with cash or with a coupon.

    I have heard of people having problems using these from time to time (I never have), but that is usually an issue of the cashier not understanding (thinking the store is getting ripped off) and can usually be taken care of by talking with a manager.

  9. Is the basic process you use for couponing to collect all of the manufacturer’s coupons and then when the stores offer their own coupons or sales each week you look back for unexpired manufacturer’s coupons to combine with?

    How much of a backlog of manufacturer’s coupons do you need for this to be effective?

  10. @suf

    Yes, that is the basic concept. You do need a backlog of Sunday coupon inserts to be able to take advantage of these deals. A 3 month backlog will get you the vast majority of the deals available. I think this is why many people find couponing frustrating. They start and see the deals, but don’t have the coupons so they get frustrated and quit. The more of a backlog you have of the inserts, the more deals you will be able to take advantage of.

    Many deals are now Internet printables, so you can still get some deals even when you don’t have an insert backlog. I would say it takes 3 to 6 months of practice to start getting good and comfortable with couponing and at that stage you can really cut your shopping bills. In this scenario I used both insert coupons and Internet coupons.

  11. I guess I’m still confused as to how combining the b1g1 free offers together makes all four free. I thought b1g1 free coupons stipulate that you have to literally buy one before you get another free (or at least would make just one product at half off).

    At the very least it seems you should have paid half price for two, and then get two additional free.

    What are the stipulations of the b1g1 free coupon vs the b1g1 free sale? What did the coupons pay for? Im just trying to figure out (like the other Ryan asked above), how the b1g1 free coupons could pay for the two trigger products if you didn’t purchase two additional trigger products for the coupons (or are is the b1g1 free coupon counting the free sale products – sort of like one sale pays for the other?). Is this how combing b1g1 free coupons and sales work?

  12. Jeffrey, I LOVE your blog! Thank you so much for taking the time and effort to walk us through one of these. In an earlier post, you asked for suggestions on what to put in a “coupon manual”. I have a couple of questions/suggestions:
    1) Stacking coupons: It appears that you cut out (or print) a manufacturer coupon for $1 off Product A – and then cut another one from a second insert, and then another… then do you go to the store and purchase ONE of Product A and use all three coupons???
    2) Catalina coupons: I often see that you “use” these, but you can only use them AFTER you’ve checked out, right? So the first time you have a transaction, you wouldn’t have a coupon? How then, can you get items for “free” if you have to purchase the first item in order to get the catalina? Also, it seems to work this way with Extra Bucks/Register Rewards too, right? You get the item “free”, but only because you have money to spend on the next visit. If you really walked into the store without a penny, could you walk away from the register relying on that deal’s “extra bucks” alone – are the savings instant?
    3) Lastly, when it comes to the BOGO items, (and there are a few comments about that here) I think the people should just try it to understand how it works. That could be a tip in your manual – tell them to just trust you. 🙂 The M&Ms deal is a great one to start with, because if you are afraid of making a mistake, you’re only out .88 cents! (And you really can’t make a mistake with this one – unless you don’t have a rewards card.)
    By the way, the BOGO work because the manufacturer (let’s say it’s Mars for the M&Ms) says “Hey! I’ll buy you a bag of M&Ms if you buy one.” Then CVS says “Hey! I’ll buy you a bag of M&Ms if you buy one.” So, you take your coupon from the Mars company and show it to CVS – it’s as GOOD AS CASH to the store. They treat this as though you’ve bought a package of M&Ms with cash. Then they make good on their offer of a free bag. Hence, you get to use the “money”/coupon from Mars to match with the offer from CVS, and walk away with two bags of free candy. By the way, I did this earlier this week (the cashier didn’t bat an eyelash) and I’ve got to say, those candies are delicious!
    Hope this helps everyone, especially for your new manual Jeffrey – keep up the great work!

  13. @ Ryan # 2, you got it at the end of your post. The store is giving you one free (in the b1g1), and the manufacturer is paying for other one (the one that you ‘bought’ in the store’s b1g1 sale). The coupon basically is saying that there must be at least 2 of those products for them to pay the store for one of them, but when you catch a store’s b1g1 sale, they’re both free. The store is still getting their $3.99 (or whatever) plus.08 processing, so they’re actually making more money by being ‘paid’ with the coupon v our cash

  14. @Ryan – I think that Chrys did a better job explaining it than I can. It seems that (and correct me if I am wrong) that you are equating “buy” with “parting with your own cash” whereas the store doesn’t care who actually pays for the other one (you or the manufacturer through a coupon) as long as they get paid.

    @Graced – I can understand how the stacking coupons can be a bit confusing, but i always only use one manufacturer coupon per item (because that is all the grocery store will allow). It is important to know all the other types of coupons that can be stacked: grocery store coupons, eCoupons (cellfire, shortcuts, and grocery store card), catalina coupons, store instant savings promotions, etc) combining several of these when possible is where the real deals are.

    You are absolutely correct about the catalina coupons (and it is the exact same with CVS Extra Bucks). You will have to make an initial outlay in cash, but you will get it back in coupons that you can use in your next purchase. This is why I have to spend some of the money I have for this challenge at CVS (I got money back). Since I already had all these coupons when I started, I have been using a zero dollar game (if I get $2 in Extra Bucks or a catalina back, I can use a $2 one that I already have as it comes out even, but I can’t use $15 in Extra Bucks or catalinas that I have and get none back and say I paid nothing)

  15. Thank you to everyone for your posts. I had the same question as Ryan re: BOGO and now I get it. I’m looking forward to trying this out!

  16. I’m beginning to grasp how the combined BOGOs work, and I’ll take your word for it that it does work, but what I just can’t get my head around is this: both offers–from the manufacturer and the merchant–require you, the consumer, to purchase one item with your own cash; I just can’t believe that neither is a stickler on this point. OK, I understand that the coupon is as good as cash to the merchant, but if they stickled, the merchant could easily get the coupon for $3.99 *and* $3.99 in cash out of your pocket. Who ever heard of a chain store’s policy on an obscure point like this *favoring* the customer?

  17. Nothing about these BOGOs make sense to me still, nor do I understand Extra Bucks. This all makes me feel quite daft to be honest.

  18. For those of you who have difficulty believing that a store would permit a BOGO coupon with a BOGO sale, google Rite Aid’s coupon policy. It specifically states that if a customer uses a BOGO coupon during a BOGO sale, both items are free.
    So if you are concerned about this, and I have heard of cashiers balking at this at CVS, try Rite Aid and bring the policy with you.

  19. Thanks Deborah. That clears it up. Policy trumps attempted logic. 😀 If it says so, then it is so!

    But I actually do get it now. The b1g1 coupon itself (which pays the store) is paying for the store’s b1g1 trigger item which then gives you the second item for free (from the store’s viewpoint). The store’s demand is all that is demanded to be satisfied in the transaction when you approach the register in a b1g1 sale.

    That you happen to happen to ALSO meet the b1g1 coupon’s stipulations (by simply showing up at the register with two items) is merely an extra bonus payout (for you), for all the coupon sees is that you have two items period, regardless which one it’s paying for, regardless if doing so triggers of an unrelated b1g1 incident (the store’s sale). Makes sense now, as clear as a lightbulb (you have to turn it on).

    For the coupon-game-challenged, such as myself (still learning, and now with another baby in tow) I like Deborah’s answer best though: if the policy says it, then it’s so, no matter how the mental gymnastics works! Trust the policy and go get some free items!

  20. To simplify:

    If you have two items, then the b1g1 coupon is like cash in your pocket for one of those items. That’s it.

    To clarify now:
    Now take that “cash” (coupon) to the store register, and to have it (the coupon) pay for one item in an unrelated b1g1 sale, and the store sees you’ve paid for one item (via the coupon) and rewards you with a second item.

    That the coupon pays for the store’s one item in an unrelated b1g1 sale is inconsequential to the coupon’s redemption requirement of you simply carrying two items to the register, one of which it agrees to pay full price for (and thus satisfies the store’s unrelated b1g1 sale). The coupon simply is saying that if you go to the register with two items, it will pick up the tab for one, regardless how you walk out with the other. It’s like the coupon is taking you out to dinner, but you pay dutch. If doesn’t care how you cover the other half, just that it knows you are walking out with another half. And in a typical store transaction, the coupon pays first before you ever do. Thus you get to be the one to walk out with the store’s b1g1 free item, while ALSO having the coupon cover the first. Neat deal huh?

  21. Graced posted a great idea about trying out a CVS BOGO deal on something simple like the M&Ms. That’s what we did a few days ago, complete coupon noobs that we are, not believing it would really work and prepared for embarrassment. But it went just as smoothly as Jeffrey describes – so we went back and loaded up on the Stayfree deal too! I think the M&M BOGO ended last night but there is an identical BOGO deal with Sobe this week, and the coupons are current, so anyone could start with that one. Try it – you’ll be hooked!

    Jeffrey, you’ve asked for suggestions on what to cover in your guide to couponing, and I will tell you that the most difficult aspect so far, which I was NOT prepared for, has been the difference in how we’re treated in some stores. We’ve already written off two local (Orange County, CA) Vons stores as being uncouponable (new word?) due to rude cashiers and managers who refused to honor coupons or follow Vons own policy – while a different Vons a few miles away did the same deals and was nothing but friendly and cooperative. Plus as beginners, we’ve made a few mistakes, and some cashiers have had no patience or civility with us. Apparently, as a serious couponer, you have to prepare yourself to be seen at some stores not as a customer, but as a freeloader. That’s been a harder adjustment for me than I would’ve thought, and somewhat stressful.

    Thanks again for the continuing education, Jeffrey. This new way of shopping and cooking is already enriching our family, which we plan to pay forward – and it all started with your blog.

  22. I though like that at first. As a “freeloader”. But now I think of it as a win/win situation.
    1) You get free products.
    2) Store gets their money back from the manufactor PLUS .08 cents
    3) Manufactor gets you to buy their product. Best advertising ever!!!

    Ok so its a win/win/win situation! (Tell that to those dumb ignorant cashiers next time!)

  23. I have a question. The CVS mailer had a limit of 8 on the M&M’s but you cut out 16 coupons. What did I miss there?

  24. @Rod

    There was nothing in the number – I just happened to have 16 inserts. I cut out 16 of the Stayfree as well even though the limit was 6. I cut out all the coupons because if there is one del like this, there will likely be another one before the coupons expire so now I have them all already cut out and don’t have to go back.

  25. I just tried to use the BOGO deal on Sobe life water at my local CVS and was told that they wouldn’t ring up the coupons because I would get them all for free. I tried to explain but ended up leaving because it was early and he was the only cashier. Was I doing something wrong? It seems identical to your deal with the m&m’s or the Stayfree. CVS offered BOGO free and I had a coupon for the same product for BOGO free. Should’ve worked right?

  26. @Alex

    I tried the Sobe deal today, and everything worked correctly (even though I don’t usually drink Sobe, but I am more than happy with 12 drinks with this unbearably hot weather). I guess you just have to consult your manager. 🙁

    Anyway, Jeffrey, I did this exact scenario (bought free M&M’s and Stayfree pads whilst using my delicious $4 off coupon). It feels nice to know that I am finding deals efficiently. Also, your rantings when you originally bought tampons (Day 15) were HILARIOUS- too bad there’s no analogous, taboo item for women to purchase. Jock straps, maybe?

  27. @Alex

    You did nothing wrong. It sounds like the cashier just didn’t know that it was allowed and since there was nobody else around, didn’t want to get in trouble for doing something wrong. I can completely sympathise with cashiers in this instant and it isn’t their fault – they just weren’t trained correctly. I would go back and talk with the manager and if the manager agrees that it is OK, to ask her/him to train the cashiers.

    These things happen and when they do, I feel (you need to make your own decision) that it is important to help educate the cashiers and managers so that the next person going through the line doesn’t have the same problem. It takes a bit of time and effort on your part, but in return you help make sure a lot of other people don’t have to go through the same experience.

  28. AWESOME step by step, thank you so much. When I went to Walgreen Saturday to get the toothbrush deal they were out, and i was pressed for time so didn’t ask for a raincheck. I’m frequently foiled in my big plans by out-of-stocks. But I have loaded up on Dove products this week at Walgreens to give to the food bank. Thanks!

  29. Wow, I can’t believe your store allows a negative subtotal. Stores in my area won’t allow that. If a coupon brings the subtotal below zero the register beeps and it won’t put it through.

  30. Thank you so much for this post. It’s great to see this all spelled out. I feel like there are little things, like the cashier not pressing Total, that still get me. This kind of info will help me feel more confident to coupon courageously in the future. 🙂

  31. This seems as good a place as any to ask about CVS “bag tags”. I recall you mentioning that you don’t use reusable bags because 1) no one gives you a discount for using them and 2) the food pantries need the plastic.

    Given your challenge, though, it seems every cent matters. CVS sells these $1.00 bag tags that give you $1.00 back for every fourth visit with a reusable bag (so, effectively, $0.25 back per visit). I would think buying a $1.00 tag and reusing a bag for all these CVS trips you make would be totally up your alley for this last month. Of course, your sister would argue that the original dollar to buy the bag tag comes out of your eating budget – and I’d agree. Mostly because the subsequent money back (more than $1, surely, since you shop there with fair regularity) would be added to your grocery budget.

  32. @T

    Yes, I use reusable bags whan I shop at CVS and have a bag tag. I had a tag long before I started this challenge — great way to earn a little extra money to use on anything you want. (I don’t at Safeway for the reasons you stated)

  33. Thanks, Jeffrey. I was curious, since I wasn’t sure if I was seeing anything about the bag tags.

  34. Heh. This isincredibly useful. Although
    I don’t currently have a place to gather Sunday inserts (my area only gets P&G Inserts but I haven’t been able to get more than one a week without buying a paper) but will be heading back to college soon. Going to see if I can hit up some places around campus to see if I can take advantage of all this useful information.

    I had no idea about the b1g1 but will definitely keep that in mind for the future.

  35. I am very surprised that your CVS allows you apply the $4 off of $20 BEFORE totalling the actual cost of your purchases. The CVSes that I shop at here in So. Cal would never agree to do this and I think CVS is right on this. If I buy four $5 items at BOGO, then I am only spending $10, it doesn’t seem right that I should be able to use a $4 off of $20 coupon under the fiction that I spent $20. In other words, I view BOGO as really being 50% off, with a minimum purchase of 2. Thoughts?

  36. @The Heg

    I learned about how the CVS cash registers work by accident. I went up one day with all my coupons assuming that I needed to hit the price after all the CVS discounts came out (like you mentioned) and had the CVS manager of the store explained to me specifically how the system works and that I didn’t need to buy so much to hit the $20 mark to trigger the coupon. She was the one that told me to always make sure the cashier doesn’t hit the total key (otherwise I would have no clue of how the system works). There is no official written policy that I have been able to find on this, but since a manager told me about it, I assume that it is okay to ask.

  37. Hi Jeffrey,

    I can’t thank you enough for this blog. We are having a tough time right now and I feel very blessed to have learned something that not only I can save money on – but be able to give to my food bank at the same time. A quick question though….on the B1G1…….in doing the math, if CVS has a B1G1 and I have a coupon for B1G1 – shouldn’t I be getting three instead of 2? 1 that I “pay” for with my coupon – 1 free from the CVS sale. But the coupon has 1 free as well, right? Or does they just cancel it out? Good luck to you!!!

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