You Will Never Feel Ready: Amy Baryshnik on Betting on Yourself
Amy Baryshnik spent nearly two decades working for other people's businesses — investment banking in LA, private equity in New York, investment management in Toronto, Chief of Staff at Knixwear — learning everything she could about how companies are built, broken, and grown. She knew the whole time she wanted to build something. She just kept waiting until she felt ready. Then one month of being woken up at 3am by the same idea finally made her honest with herself: she was never going to feel ready, and that was exactly the point.
In This Episode, host Sarah Jeanneault and Amy unpack:
- The career arc that took Amy from Ivey Business School to investment banking in LA, to Apollo in New York, to 12 years working directly for three founder CEOs — and why she describes all of it as deliberate preparation for the day she would finally bet on herself
- What happened at Knixwear that no one else in the organization was equipped to handle: Amy led the sale of an 80% stake in the business to Essity, a global CPG out of Sweden, and spent a year leading the integration — because she was the only person in the room with an M&A background
- Why she left Knixwear at 40, set out to buy an existing business, and instead kept getting woken up at night by a decade-old idea — and what finally made her commit
- The Estate Kit origin story: her father's brain tumor diagnosis, being named decision-maker in a hospital hallway moments before surgery, and the realization that most families face that moment completely unprepared
- Why Amy believes the biggest unlock for Estate Kit isn't product — it's breaking down the taboos that keep people from engaging with the topic at all: mortality, money, family dynamics, and end-of-life wishes, all in one conversation
- Her chapter title for right now: "Let's talk about death and all the other topics that make you the life of the party".
Episode Highlights:
00:00 - Choosing Before You’re Ready
00:30 - Podcast Intro
00:42 - Meet Amy and Her Story
01:21 - From Banking to Operating
03:51 - Owning Decisions and Friction
06:35 - Leveraging M&A Background
09:15 - Culture Energy and Growth
12:30 - Hiring for Growth Mindset
14:11 - Estate Kit; Building Trust Around Death
16:19 - The Personal Origin Story
19:23 - Betting on Herself and Overcoming Fear
21:51 - You Will Never Feel Ready
23:30 - Leading as CEO
26:02 - Breaking Death Taboos
28:38 - Gut Check After the Interview
34:55 - Ideas Focus and Fulfillment
44:21 - Wrap Up and Call to Action
Resources Mentioned
- Estate Kit — Amy's company; free 12-question estate planning assessment available at estatekit.com
- Knixwear — Canadian D2C brand where Amy served as Chief of Staff; she led the sale of an 80% stake to Essity
- Essity — global CPG company based in Sweden; acquired an 80% stake in Knixwear during Amy's tenure
Amy Baryshnik is the founder and president of Estate Kit, a platform that helps families organize and securely share the documents, contacts, and instructions their loved ones will need when it matters most. She brings nearly two decades of leadership experience across investment management and retail, including roles as Chief of Staff at Knixwear and Partner and COO at Alignvest Management Corporation. A board member at NEXT Canada and trustee at the Jewish Foundation of Greater Toronto, Amy holds an MBA with distinction from Harvard Business School and an HBA with distinction from the Ivey Business School at Western University.
Connect with Amy Baryshnik: https://www.linkedin.com/in/amybaryshnik/
Connect with Us!
whytotheway@gmail.com
This show is produced by Twisted Spur Media Ltd.
Disclaimer: The views, information, or opinions expressed by guests during Why To The Way Podcast are solely those of the individuals involved and do not necessarily represent those of Sarah Jeanneault, Twisted Spur Media Ltd. and/or her affiliates. Sarah Jeanneault, Why To The Way Podcast, and Twisted Spur Media Ltd. are not responsible for and do not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.
