Comedian-actor-strategist on finding your voice and using it episode artwork

EPISODE · Jun 25, 2026 · 51 MIN

Comedian-actor-strategist on finding your voice and using it

from The Unemployment Diaries · host Aisha Ommaya

Will is a triple threat: stand-up comedian, actor, and B2B content strategist with a newsletter that gets a 70% open rate. He's also someone who spent years flattening himself to fit inside corporate culture (anyone else resonate?) — and is now methodically peeling every layer back.We talk about what it actually means to build an audience, why human content will always beat AI, and how Will is redefining success not by what he's gaining, but by what he's refusing to become again.In this conversation we discuss:Dropping out 7 classes short to build one of the first web companiesWhat panic-applying after a layoff actually feels like and why he stopped waiting to be pickedWhy comedian + actor + content strategist just makes senseThe content mistake most brands make and the 70% open rate that proves there's a better wayHis architectural approach to content developmentWhat he was tolerating in corporate that he couldn't name until he leftSuccess by subtraction: becoming more you by refusing to be anything elseWhy he almost turned this podcast down and what that says about how we measure ourselvesChapters(00:00) Introducing: Will Thomas(01:07) How comedian-actor-strategist answers "what do you do?"(05:59) The bold decision to drop out of college(11:50) Finding discipline in a crazy commute(15:10) From corporate to creative freedom(21:03) What Will was tolerating (25:54) The importance of support systems(27:16) Architectural approach to content creation(29:41) Emotional intelligence in content creation(32:07) Leveraging humor and unique perspectives(35:47) Building a personal brand(39:14) Defining success on your own terms(45:54) Authenticity over comparisonWhere to find Will Newsletter: https://www.williamathomas.com/sunday-setupLinkedIn: https://www.linkedin.com/in/williamathomas/Website: https://www.5thhouseleo.com/For more from The Unemployment DiariesStay up to date on InstagramGo behind the scenes on SubstackWatch on YouTube

Will is a triple threat: stand-up comedian, actor, and B2B content strategist with a newsletter that gets a 70% open rate. He's also someone who spent years flattening himself to fit inside corporate culture (anyone else resonate?) — and is now methodically peeling every layer back.We talk about what it actually means to build an audience, why human content will always beat AI, and how Will is redefining success not by what he's gaining, but by what he's refusing to become again.In this conversation we discuss:Dropping out 7 classes short to build one of the first web companiesWhat panic-applying after a layoff actually feels like and why he stopped waiting to be pickedWhy comedian + actor + content strategist just makes senseThe content mistake most brands make and the 70% open rate that proves there's a better wayHis architectural approach to content developmentWhat he was tolerating in corporate that he couldn't name until he leftSuccess by subtraction: becoming more you by refusing to be anything elseWhy he almost turned this podcast down and what that says about how we measure ourselvesChapters(00:00) Introducing: Will Thomas(01:07) How comedian-actor-strategist answers "what do you do?"(05:59) The bold decision to drop out of college(11:50) Finding discipline in a crazy commute(15:10) From corporate to creative freedom(21:03) What Will was tolerating (25:54) The importance of support systems(27:16) Architectural approach to content creation(29:41) Emotional intelligence in content creation(32:07) Leveraging humor and unique perspectives(35:47) Building a personal brand(39:14) Defining success on your own terms(45:54) Authenticity over comparisonWhere to find Will Newsletter: https://www.williamathomas.com/sunday-setupLinkedIn: https://www.linkedin.com/in/williamathomas/Website: https://www.5thhouseleo.com/For more from The Unemployment DiariesStay up to date on InstagramGo behind the scenes on SubstackWatch on YouTube

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Comedian-actor-strategist on finding your voice and using it

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This episode was published on June 25, 2026.

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Will is a triple threat: stand-up comedian, actor, and B2B content strategist with a newsletter that gets a 70% open rate. He's also someone who spent years flattening himself to fit inside corporate culture (anyone else resonate?) — and is now...

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