The Founders Playbook: How to Build, Fund and Pitch Your Startup episode artwork

EPISODE · Sep 1, 2025 · 58 MIN

The Founders Playbook: How to Build, Fund and Pitch Your Startup

from Reclaiming Bossy · host Maahika Singh

If you’re a founder, or dreaming of becoming one, this episode is your essential starter pack. I’m joined by Hattie Willis, founder of GuessWorks and If We Raise, to break down everything you need to know about building, funding, and sustaining a company…We begin by stripping away the jargon and exploring the different types of entrepreneurs and what it really means to be a founder. From there, we dive into the world of investors: the types you’ll encounter, whether raising is right for you, and the red flags and green flags every founder should watch for.Pitching is another area we go deep on, how to pitch to clients, your team, and, of course, investors, with practical advice you can put into action immediately. We also unpack the funding gap, what it means for women and underrepresented founders, and how to address it. Finally, we close with a conversation on founder wellbeing because building a business shouldn’t come at the cost of your health and happinessThis conversation is as close as you’ll get to a founder’s playbook. Whether you’re just starting out or looking to refine your approach, this episode is your go-to resource for building smarter, pitching better, and thriving as a founder.The biggest myths and jargon in entrepreneurship (and what they actually mean)How to identify what type of founder you areThe key differences between raising and bootstrapping and how to know which path is right for youRed flags and green flags when working with investorsHow to pitch effectively to clients, teams, and investorsWhy the funding gap exists and how founders can navigate itPractical strategies for protecting and prioritizing founder wellbeingGuessWorks: https://www.guessworks.conot my first guess instagram https://www.instagram.com/notmyfirstguess/?hl=enIf We Raise: https://www.ifweraise.com/aboutLinkedIn: https://www.linkedin.com/in/hattie-willis-2b47b376/?originalSubdomain=ukInstagram: Maahika.stiktok: Maahika.sinstagram: empowersoundstiktok: empowersoundspodcastfor collaborations and enquires please contact : [email protected] you enjoyed this conversation, don’t forget to subscribe, share, and leave a review so more founders can find these insights.

If you’re a founder, or dreaming of becoming one, this episode is your essential starter pack. I’m joined by Hattie Willis, founder of GuessWorks and If We Raise, to break down everything you need to know about building, funding, and sustaining a company…We begin by stripping away the jargon and exploring the different types of entrepreneurs and what it really means to be a founder. From there, we dive into the world of investors: the types you’ll encounter, whether raising is right for you, and the red flags and green flags every founder should watch for.Pitching is another area we go deep on, how to pitch to clients, your team, and, of course, investors, with practical advice you can put into action immediately. We also unpack the funding gap, what it means for women and underrepresented founders, and how to address it. Finally, we close with a conversation on founder wellbeing because building a business shouldn’t come at the cost of your health and happinessThis conversation is as close as you’ll get to a founder’s playbook. Whether you’re just starting out or looking to refine your approach, this episode is your go-to resource for building smarter, pitching better, and thriving as a founder.The biggest myths and jargon in entrepreneurship (and what they actually mean)How to identify what type of founder you areThe key differences between raising and bootstrapping and how to know which path is right for youRed flags and green flags when working with investorsHow to pitch effectively to clients, teams, and investorsWhy the funding gap exists and how founders can navigate itPractical strategies for protecting and prioritizing founder wellbeingGuessWorks: https://www.guessworks.conot my first guess instagram https://www.instagram.com/notmyfirstguess/?hl=enIf We Raise: https://www.ifweraise.com/aboutLinkedIn: https://www.linkedin.com/in/hattie-willis-2b47b376/?originalSubdomain=ukInstagram: Maahika.stiktok: Maahika.sinstagram: empowersoundstiktok: empowersoundspodcastfor collaborations and enquires please contact : [email protected] you enjoyed this conversation, don’t forget to subscribe, share, and leave a review so more founders can find these insights.

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The Founders Playbook: How to Build, Fund and Pitch Your Startup

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This episode is 58 minutes long.

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This episode was published on September 1, 2025.

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If you’re a founder, or dreaming of becoming one, this episode is your essential starter pack. I’m joined by Hattie Willis, founder of GuessWorks and If We Raise, to break down everything you need to know about building, funding, and sustaining a...

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