
Nobody is born knowing how to pitch. (Katie here) I've been known to pitch once, hear nothing, and decide 'Oh well. Never mind.' Then never reach out ever again. 😅 So you can imagine my SHOCK and INCREDULITY (is that a word?) when Kira told me that she will reach out 7 times to a brand before giving up. Whaaaaaat!? Kira Matthews (aka Kira the Bold), is like confidence in a bottle. She's mastered pitching and landing work with names like Squarespace, Ganni, and lots more. If contacting publishers and/or potential clients makes you do a little bit of sick in your mouth, this episode will definitely help! At the very least you'll feel inspired to send more than one follow up email. In this episode, we chat about: What to do when the work… just stops coming in Why pitching can feel so scary The real reason people don’t hear back. (And nooo, it’s not because they hate you) Why one email is basically just saying hello How to follow up without being annoying (or feeling like you are) Timestamps: 00:00 Meet Kira (Queen of Pitching 👑) 01:00 From fashion styling to building a business 02:00 When the work disappeared… and what she did next 03:00 Learning to pitch (while still being terrified) 05:00 Fear doesn’t go away. You just get used to it 06:00 The 3-year journey to landing Squarespace 08:00 Why most people give up after one email 09:00 The stories we tell ourselves about rejection 10:00 Why you need to follow up (a lot more than you think) 11:00 How to make each email actually count 12:00 Applying this to illustration and getting your work seen 13:00 Inside Kira’s talent agency experiment 15:00 Why smaller creatives need to pitch more, not less 17:00 Agents, money, and what’s really going on behind the scenes 19:00 Why agents aren’t a magic solution 20:00 Sales: the bit everyone wants to avoid 23:00 Why follow-up feels rude (but isn’t) 24:00 Rejection challenges and building resilience 26:00 Rejection = start of the conversation 28:00 Momentum, energy, and creating your own opportunities 30:00 The actions that actually lead to results 31:00 Telling people what you do (important!!) 32:00 Katie’s rejection challenge story 34:00 Auditing your time and what’s worth it 35:00 Kira’s final pep talk Links & stuff wot we mentioned Kira’s website: https://www.kiramatthews.com/ Instagram: https://www.instagram.com/kirathebold/ Weekly pitch tips newsletter: https://kirathebold.myflodesk.com/m0elc4qip7 The Good Ship Illustration https://www.thegoodshipillustration.com/freebies Byeeee for now! x The Good Ship Illustration (Helen, Katie & Tania) Come and say hello! ✏️ @thegoodshipillustration 🌏 www.thegoodshipillustration.com p.s. We love answering your illustration questions. Click here to submit your question for The Good Ship Illustration Podcast 🎙
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