Taryn Williams started her first company, Wink Models, at 21 with $30,000 and no roadmap. She didn't stop there. Over the next two decades she built and ran a string of ventures, the talent marketplace The Right Fit (backed by Airtree, scaled to 17,000 talent and 11,000 clients across APAC), The Influencers Agency, the contra-gifting platform #Gifted, the B2B talent business Notable, and Online Model Academy, exiting two of them to international acquirers in 2023. Today she sits across boards, invests as an angel, and advises organisations on AI transformation with Think & Grow.

In this episode Pauline sits down with Taryn for an honest conversation about what it actually costs to build like this: why and how she runs multiple companies at once, why she loves the 0-to-2-year stage and does not want to be the CEO, and the quieter things founders rarely say out loud, the toll on her relationships and health, freezing her eggs at 35 and what she wishes she'd known about fertility, and the mentor question she still works through every day: when is enough, enough? Plus sharp takes on AI, the creator economy, "AI slop", and whether AI will replace human models.

Time Stamps

00:00 - Cold open: "I was 21 when I started Wink"

01:20 - Welcome — meeting Taryn at South Start, and the snapshot of a serial founder

04:08 - Scouted at 15: modelling as an accidental business education

06:21 - Starting Wink Models at 21 — fixing a broken, fragmented industry

09:04 - Building the first tech product (and the trap of gold-plating instead of an MVP)

12:21 - Launching The Right Fit and raising capital from Airtree

17:56 - How big Wink and The Right Fit actually grew

19:34 - Running multiple companies at once — and stepping fully out of Wink

22:13 - #Gifted, Notable and Online Model Academy: "every year, birth a new child"

28:27 - Why it isn't "the Taryn Williams show"

31:37 - The 2023 exits: running a formal process and the transition

38:56 - The real cost: relationships, health and never being fully switched off

43:27 - Fertility, freezing eggs at 35, and what no one tells you early enough

50:15 - From operator to board chair — breaking the habit of being all-in

54:17 - Why every founder should understand governance (the AICD course)

56:28 - In the investor seat: what Taryn backs and the founders she looks for

59:33 - Advising on AI transformation with Think & Grow

64:56 - AI, creators and the "AI slop" problem

69:07 - Will AI models replace human talent in advertising?

73:32 - Dating, connection and AI: why we've lost the resilience for friction

80:45 - Tying self-worth to success — the question she still works through

85:16 - One thing she knows to be true that the world hasn't caught up on yet

87:36 - Close

Links

Wink Models — https://www.winkmodels.com.au

Airtree Ventures — https://www.airtree.vc

Think & Grow — https://www.thinkandgrow.com

Australian Institute of Company Directors (AICD) — https://www.aicd.com.au

Perspective X is produced by Day One — the podcast network for founders, operators and investors — https://www.dayone.fm

Mentioned in this episode:

Deel x PX_Script 2

Deel x PX_Script 1

Day One sting