Stormy Simon - Entrepreneur & Equity Advocate | Breaking The Glass Ceiling

Stormy Simon is a glass-ceiling shattering e-commerce pioneer, corporate renegade, cannabis activist, and public speaker who went from being hired as a temporary employee and worked her way up to President of a $2B company (Overstock.com) with worldwide recognition.A sought-after speaker and panelist, Stormy delivered the keynote address at the Aspen YPO Conference in 2019 and debuted an inspirational TedTalk in 2018. An unconventional leader who went straight into the workforce, bypassing college and business school, she has been featured throughout the media landscape in outlets including Inc., The Washington Post, Forbes, SF Chronicle, MSN, Cheddar, Yahoo!, Entrepreneur, PopSugar, CNBC, and Fox Business.

➡️ Talking Points

00:00 — Intro

03:27 — Stormy Simon’s origin story

06:16 — Effect of early-life responsibilities on Stormy’s personality

08:30 — Stormy’s entry point into her career

13:17 — Realizing you can bet on yourself

15:08 — Stormy’s drive behind working at her new job

17:15 — How to stay grounded after getting success

26:56 — What made Stormy want to leave her job?

35:48 — The one lever Stormy pulled at Overstock that she’s really proud of

39:30 — The impact of the employees’ behavior on the growth of an organization

44:19 — Stormy’s experience during and after leaving Overstock

1:01:12 — What is Stormy doing now in her career?

1:05:15 — Are we moving towards a more ethical, socially conscious version of capitalism?

1:07:31 — Are there any competitors creating similar alternatives for small businesses like Amazon?

1:11:30 — What is Stormy building from scratch?

1:13:47 — Starting from zero

1:19:29 — Stormy’s work routine

1:21:28 — Advice for amateur entrepreneurs

1:29:20 — Where can people connect with Stormy Simon?

1:29:46 — What keeps Stormy up at night?

1:31:06 — The biggest challenge Stormy Simon ever faced in her life

1:33:16 — The most impactful person in Stormy Simon’s life

1:35:23 — Stormy Simon’s book or podcast recommendation

1:37:34 — What would Stormy Simon tell her 20-year-old self?

1:38:49 — What does success mean to Stormy Simon?