Adeline Westover Chakraborty , PhD Economics

Adeline came out of a macro research role at a central bank before joining a multi-family office where she now runs the founder-advisory vertical. Her clients are founders and co-founders of venture-backed companies at every stage from seed to unicorn. She does the kind of work that sits between pure tax planning and pure investment strategy: she models dilution across hypothetical future rounds, she quantifies the expected value of different 83(b)-plus-QSBS stacking structures, and she helps founders think about how much primary versus secondary capital to take at each round.

The decision she is pulled into most is the Series B secondary. A founder holds 22% of a $400M post-money company, with a strike of pennies from a 2019 83(b)-elected purchase. The board is supportive of letting her sell $8M of her position into the incoming round. On paper the gain is pure QSBS-eligible long-term capital gain, fully excluded up to the $10M federal cap, resulting in effectively zero federal tax on the secondary. Adeline spends the conversation instead on what the secondary costs: 1.8% of the company permanently transferred to financial investors, a signal to the existing cap table about commitment, and a reset of the founder’s concentration that changes every subsequent planning question.

She reviews content on founder equity, 83(b) mechanics, and QSBS planning for founders.