I agree - I think you were approaching the problem from the WS POV 
From a VBA approach, maybe something like this.
Option Explicit
'If the Description contains 1 of 4 things (******776, ******732, Vanguard, or Robinhood) AND the Type is a Withdrawal,
'I want the value under Amount to go from a negative value to a positive value and
'I want the Type to go from Withdrawal to Deposit. The number will only ever need to go from negative to positive.
'The reason these need to be If/AND type statements is because even though the row contains the key word Robinhood,
'there are both withdrawals and deposits that contain the same word.
'So I wouldn't want to make those positive numbers negative by mistake.
Const colAmt As Long = 1
Const colType As Long = 2
Const colDesc As Long = 3
Sub ManipulateData()
Dim rData As Range, rRow As Range
Set rData = ActiveSheet.Cells(1, 1).CurrentRegion
Application.ScreenUpdating = False
For Each rRow In rData.Rows
With rRow
Select Case .Cells(colDesc).Value
Case "******776", "******732", "Vanguard", "Robinhood"
If .Cells(colType).Value = "Withdrawal" Then
.Cells(colAmt).Value = -1# * .Cells(colAmt).Value
.Cells(colType).Value = "Deposit" '!!!! missed this
End If
End Select
End With
Next
Application.ScreenUpdating = True
End Sub