W-9 filled out inSharpie,photographedsideways, witha tasteful coffeestain.Huntedthroughemail inboxfor vendorinfoHad 16spreadsheettabs open atonceClient:"Just uselast year'sinfo"“We paid themas acontractor... butthey’re actuallyan employee.”"Oh wait, thatwas areimbursement..."(...or was it?)WatchedKeeper's 1099webinar withNancyMcClelland andJennifer Dymond!Client: “Whydidn’t youremind mesooner?” (Youreminded them6 times.)Subscribed to1099problems.io1099 prepdoneBEFOREJanuary 20thusing KeeperTasks auto-assigned inKeeper for1099 seasonprep :)Vendorpaid bycheck ANDPayPal"The ownersaid they’rea sole propAND anLLC."“They onlyreceived$599, wedon’t need a1099 right?”UsedKeeper'sPrepare1099 ReportChased aW-9 for 3weeks (ormore)Tracked1099vendors in aspreadsheet(again)Finally gotmissing info!... onJanuary 30Requested aW-9 *again*this year only tosee that thevendor is a C-CorpVendorwon't returnmy W-9requestRealizedhalfwaythrough prepthat client usedpersonal fundsEnteredTINs byhand forevery vendorClientinsists wedon't needa W-9Filed MISCinstead ofNEC(oops!)Said "Ihate 1099season" atleast onceBooked a post-1099 seasonmassagebefore 1099season evenstartedFounduntrackedpaymentsin VenmoDrank 3coffees inone day inthe month ofJanuary"But why doyou need mysocialsecuritynumber"W-9 is justa blurrycellphonepictureVendor's legalname doesn’tmatch theirpayment platformusername —again."What'sa 1099again?"Wished we theW-9 requestprocess earlierin the year...."Can wejust file anextension?"W-9 filled out inSharpie,photographedsideways, witha tasteful coffeestain.Huntedthroughemail inboxfor vendorinfoHad 16spreadsheettabs open atonceClient:"Just uselast year'sinfo"“We paid themas acontractor... butthey’re actuallyan employee.”"Oh wait, thatwas areimbursement..."(...or was it?)WatchedKeeper's 1099webinar withNancyMcClelland andJennifer Dymond!Client: “Whydidn’t youremind mesooner?” (Youreminded them6 times.)Subscribed to1099problems.io1099 prepdoneBEFOREJanuary 20thusing KeeperTasks auto-assigned inKeeper for1099 seasonprep :)Vendorpaid bycheck ANDPayPal"The ownersaid they’rea sole propAND anLLC."“They onlyreceived$599, wedon’t need a1099 right?”UsedKeeper'sPrepare1099 ReportChased aW-9 for 3weeks (ormore)Tracked1099vendors in aspreadsheet(again)Finally gotmissing info!... onJanuary 30Requested aW-9 *again*this year only tosee that thevendor is a C-CorpVendorwon't returnmy W-9requestRealizedhalfwaythrough prepthat client usedpersonal fundsEnteredTINs byhand forevery vendorClientinsists wedon't needa W-9Filed MISCinstead ofNEC(oops!)Said "Ihate 1099season" atleast onceBooked a post-1099 seasonmassagebefore 1099season evenstartedFounduntrackedpaymentsin VenmoDrank 3coffees inone day inthe month ofJanuary"But why doyou need mysocialsecuritynumber"W-9 is justa blurrycellphonepictureVendor's legalname doesn’tmatch theirpayment platformusername —again."What'sa 1099again?"Wished we theW-9 requestprocess earlierin the year...."Can wejust file anextension?"

1099 Season Cow-a-Bingo - Call List

(Print) Use this randomly generated list as your call list when playing the game. There is no need to say the BINGO column name. Place some kind of mark (like an X, a checkmark, a dot, tally mark, etc) on each cell as you announce it, to keep track. You can also cut out each item, place them in a bag and pull words from the bag.


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  1. W-9 filled out in Sharpie, photographed sideways, with a tasteful coffee stain.
  2. Hunted through email inbox for vendor info
  3. Had 16 spreadsheet tabs open at once
  4. Client: "Just use last year's info"
  5. “We paid them as a contractor... but they’re actually an employee.”
  6. "Oh wait, that was a reimbursement..." (...or was it?)
  7. Watched Keeper's 1099 webinar with Nancy McClelland and Jennifer Dymond!
  8. Client: “Why didn’t you remind me sooner?” (You reminded them 6 times.)
  9. Subscribed to 1099problems.io
  10. 1099 prep done BEFORE January 20th using Keeper
  11. Tasks auto-assigned in Keeper for 1099 season prep :)
  12. Vendor paid by check AND PayPal
  13. "The owner said they’re a sole prop AND an LLC."
  14. “They only received $599, we don’t need a 1099 right?”
  15. Used Keeper's Prepare 1099 Report
  16. Chased a W-9 for 3 weeks (or more)
  17. Tracked 1099 vendors in a spreadsheet (again)
  18. Finally got missing info! ... on January 30
  19. Requested a W-9 *again* this year only to see that the vendor is a C-Corp
  20. Vendor won't return my W-9 request
  21. Realized halfway through prep that client used personal funds
  22. Entered TINs by hand for every vendor
  23. Client insists we don't need a W-9
  24. Filed MISC instead of NEC (oops!)
  25. Said "I hate 1099 season" at least once
  26. Booked a post-1099 season massage before 1099 season even started
  27. Found untracked payments in Venmo
  28. Drank 3 coffees in one day in the month of January
  29. "But why do you need my social security number"
  30. W-9 is just a blurry cellphone picture
  31. Vendor's legal name doesn’t match their payment platform username — again.
  32. "What's a 1099 again?"
  33. Wished we the W-9 request process earlier in the year....
  34. "Can we just file an extension?"