Filed MISCinstead ofNEC(oops!)"The ownersaid they’rea sole propAND anLLC."Realizedhalfwaythrough prepthat client usedpersonal fundsChased aW-9 for 3weeks (ormore)Subscribed to1099problems.io"Oh wait, thatwas areimbursement..."(...or was it?)"But why doyou need mysocialsecuritynumber""What'sa 1099again?"“We paid themas acontractor... butthey’re actuallyan employee.”Said "Ihate 1099season" atleast onceHuntedthroughemail inboxfor vendorinfoTasks auto-assigned inKeeper for1099 seasonprep :)Finally gotmissing info!... onJanuary 30Had 16spreadsheettabs open atonce1099 prepdoneBEFOREJanuary 20thusing KeeperW-9 filled out inSharpie,photographedsideways, witha tasteful coffeestain.Tracked1099vendors in aspreadsheet(again)EnteredTINs byhand forevery vendorFounduntrackedpaymentsin VenmoWished we theW-9 requestprocess earlierin the year....UsedKeeper'sPrepare1099 ReportWatchedKeeper's 1099webinar withNancyMcClelland andJennifer Dymond!Clientinsists wedon't needa W-9“They onlyreceived$599, wedon’t need a1099 right?”Vendorpaid bycheck ANDPayPalW-9 is justa blurrycellphonepictureClient: “Whydidn’t youremind mesooner?” (Youreminded them6 times.)Vendorwon't returnmy W-9requestDrank 3coffees inone day inthe month ofJanuaryVendor's legalname doesn’tmatch theirpayment platformusername —again.Client:"Just uselast year'sinfo"Booked a post-1099 seasonmassagebefore 1099season evenstartedRequested aW-9 *again*this year only tosee that thevendor is a C-Corp"Can wejust file anextension?"Filed MISCinstead ofNEC(oops!)"The ownersaid they’rea sole propAND anLLC."Realizedhalfwaythrough prepthat client usedpersonal fundsChased aW-9 for 3weeks (ormore)Subscribed to1099problems.io"Oh wait, thatwas areimbursement..."(...or was it?)"But why doyou need mysocialsecuritynumber""What'sa 1099again?"“We paid themas acontractor... butthey’re actuallyan employee.”Said "Ihate 1099season" atleast onceHuntedthroughemail inboxfor vendorinfoTasks auto-assigned inKeeper for1099 seasonprep :)Finally gotmissing info!... onJanuary 30Had 16spreadsheettabs open atonce1099 prepdoneBEFOREJanuary 20thusing KeeperW-9 filled out inSharpie,photographedsideways, witha tasteful coffeestain.Tracked1099vendors in aspreadsheet(again)EnteredTINs byhand forevery vendorFounduntrackedpaymentsin VenmoWished we theW-9 requestprocess earlierin the year....UsedKeeper'sPrepare1099 ReportWatchedKeeper's 1099webinar withNancyMcClelland andJennifer Dymond!Clientinsists wedon't needa W-9“They onlyreceived$599, wedon’t need a1099 right?”Vendorpaid bycheck ANDPayPalW-9 is justa blurrycellphonepictureClient: “Whydidn’t youremind mesooner?” (Youreminded them6 times.)Vendorwon't returnmy W-9requestDrank 3coffees inone day inthe month ofJanuaryVendor's legalname doesn’tmatch theirpayment platformusername —again.Client:"Just uselast year'sinfo"Booked a post-1099 seasonmassagebefore 1099season evenstartedRequested aW-9 *again*this year only tosee that thevendor is a C-Corp"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. Filed MISC instead of NEC (oops!)
  2. "The owner said they’re a sole prop AND an LLC."
  3. Realized halfway through prep that client used personal funds
  4. Chased a W-9 for 3 weeks (or more)
  5. Subscribed to 1099problems.io
  6. "Oh wait, that was a reimbursement..." (...or was it?)
  7. "But why do you need my social security number"
  8. "What's a 1099 again?"
  9. “We paid them as a contractor... but they’re actually an employee.”
  10. Said "I hate 1099 season" at least once
  11. Hunted through email inbox for vendor info
  12. Tasks auto-assigned in Keeper for 1099 season prep :)
  13. Finally got missing info! ... on January 30
  14. Had 16 spreadsheet tabs open at once
  15. 1099 prep done BEFORE January 20th using Keeper
  16. W-9 filled out in Sharpie, photographed sideways, with a tasteful coffee stain.
  17. Tracked 1099 vendors in a spreadsheet (again)
  18. Entered TINs by hand for every vendor
  19. Found untracked payments in Venmo
  20. Wished we the W-9 request process earlier in the year....
  21. Used Keeper's Prepare 1099 Report
  22. Watched Keeper's 1099 webinar with Nancy McClelland and Jennifer Dymond!
  23. Client insists we don't need a W-9
  24. “They only received $599, we don’t need a 1099 right?”
  25. Vendor paid by check AND PayPal
  26. W-9 is just a blurry cellphone picture
  27. Client: “Why didn’t you remind me sooner?” (You reminded them 6 times.)
  28. Vendor won't return my W-9 request
  29. Drank 3 coffees in one day in the month of January
  30. Vendor's legal name doesn’t match their payment platform username — again.
  31. Client: "Just use last year's info"
  32. Booked a post-1099 season massage before 1099 season even started
  33. Requested a W-9 *again* this year only to see that the vendor is a C-Corp
  34. "Can we just file an extension?"