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 🎙