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EP13: Josh Aronoff: The Unknown Unknowns - What Grief Taught Me About Estate Planning
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Josh Aronoff lost his father and found himself staring down a mountain of financial unknowns - outdated estate documents, scattered accounts, and the crushing pressure to make sense of it all while grieving.
Justin Weidenfeld sits down with Josh to talk about how stepping into fix-it mode became both a coping mechanism and a catalyst for change. As the oldest child and a naturally practical thinker, Josh took the lead in handling his father’s affairs, only to discover how little guidance exists when you’re dealing with loss, logistics, and legal complexities all at once.
Despite his background in law and finance, Josh quickly realized that navigating death brings a particular kind of stress and anxiety, not from financial decision-making, but from the overwhelming number of unknowns and lack of clarity in the process. This lived experience became the foundation for Herbie, a platform Josh co-founded to simplify estate planning and remove the emotional and practical burden from grieving families. Named after his dad, Herbie helps people avoid the chaos Josh faced by making organization, communication, and planning as straightforward as possible.
Josh and Justin’s conversation explores what it means to support others in their grief, how legacy lives in both memories and paperwork, and why having a plan in place is an act of love.
Episode Breakdown:
00:00 Why Death and Money Are Hard to Talk About
03:22 Josh’s Grief Story: Losing His Father and Facing the Unknown
09:38 Becoming the Emotional and Logistical Rock for the Family
23:20 When Finances Collide with Grief: The Wake-Up Moment
26:19 The Hidden Complexity of Organizing an Estate
30:01 Probate, Unknown Unknowns, and What No One Teaches You
47:26 Naming Beneficiaries vs. Relying on Legal Documents
57:20 Creating Herbie: A Platform Built From Personal Loss
1:07:23 Why Sharing Your Estate Plan Matters
1:14:02 Grief Mantra: One Bite at a Time
Links
Connect with Josh Aronoff:
Website: herbieplan.com
LinkedIn: https://www.linkedin.com/in/josh-aronoff-3035a727/
Connect with Justin Weidenfeld:
LinkedIn: https://www.linkedin.com/in/justin-weidenfeld/
LinkedIn: https://www.linkedin.com/company/the-currency-of-grief-podcast/
Instagram: https://www.instagram.com/thecurrencyofgrief_podcast
TikTok: https://www.tiktok.com/@thecurrencyofgrief
YouTube: https://www.youtube.com/@TheCurrencyofGrief
Website: https://www.ironbridgewc.com/team/justin-weidenfeld
16 episodes
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