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My first thought was that it meant usury, but apparently Buddhagosa defines it as,
'Herein, what is pursuing gain with gain? Seeking, seeking for, seeking out, going in search of, searching for, searching out material goods by means of material goods, such as carrying there goods that have been got from here, or carrying here goods that have been got from there, by one bent on gain, honour and renown, by one of evil wishes, a prey to wishesβthis is called pursuing gain with gain' (Vbh. 352- 53).
... which I think implies being a merchant (buying here and selling there), or more generally capitalism.
Note that that sutta is addressed to monks.
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Interesting answers, especially the Buddhaghosa answer. I also heard an interesting suggestion that gain may have meant 'profit', thus gain-with-gain meant compounded interest. But then I thought Buddha did say that honest wealth was acquired by the sweat of ones brow and the strength of one's arms, so I inclined to Buddhaghosa's interpretation. Also consider that the merchants were the ones that used 'writing' in Buddha's time, which was a reason that writing was considered to be a lowly practice. Merchants were pretty much considered to be lowlifes in Buddha's day.