In this episode, Jack is joined by Guy Zeltser, CFO of Hippo Insurance. One of the more consequential decisions in Hippo’s recent history involved deliberately reducing the size of its homeowners insurance business. Following a difficult period in 2023, the company needed to rebalance its exposure to risk—even if that meant temporarily moving backward on […]
The Reset That Restarted Growth
Facing slowing growth, Aidan Viggiano led a sweeping reset—workforce reductions, compensation redesign, leadership changes, and governance overhaul—shifting the company toward balanced growth and profitability. Anchored by a “do what we said we would do” mindset, she rebuilt financial discipline, restored credibility, and emerged a stronger, more decisive leader. Now Watch Our Complete Episode Featuring CFO […]
The Mentoring Round | Lawrence Herman, CFO, Dwolla
Inside The Mentoring Round, CFO Lawrence Herman reflects on his experience during the “Bitcoin winter” when he advised against the popular opinion to sell off assets. He advocated for buying more Bitcoin as a strategy to preserve and potentially increase the company’s financial health during a market downturn. At Dwolla, Herman’s priorities include optimizing cash […]