"Hey guys. First time caller, long time listener. I’m 36, happily married to a former pageant hottie and 3 kids living in Lincoln, NE. We had a fortunate liquidity event during 2021, where I sold 50% of my shares in a tech start up. Overnight we went from having $400k (mostly lore-tax) in retirement accounts to $2m investable total with 50% of shares still invested. Income is about $120k which is in the financial services industry. We have a start up hobby farm that is starting to show profit but we have lots of capital investment needed to make the farm grow. Ie, tractor, barn, etc. My question is if we could look at a tax strategy where we invest into our active farm business (resulting in a significant loss) and simultaneously convert all or a portion our pre-tax 401k at more advantageous marginal tax rate? Drive a 2015 Chevy Silverado and michelada is the drink of choice!"
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