Sponsored by HighLevel
This episode is sponsored by HighLevel — the all-in-one platform for funnels, CRM, marketing automation, and lead management.
With my link, you get 30 days free.

👉 Start your 30-day free trial here: https://www.gohighlevel.com/simonsays

If you want access to my custom HighLevel dashboard for keeping track of your outbound and managing client relationships click here 👇

HighLevel dashboard

—

Episode 9 — Small audience, big leap

This week on Simon Says, five very different dreams share the same heartbeat: start before you feel ready.

• Daniel Sheehan — Travel creator
  He doesn’t have a million followers. He has a map and a point to prove. We swap “waiting to be discovered” for a simple promise: bring places to life so well that brands want to be part of the story.

  YT: I Wish I Did That When I Was Younger

  IG: iwishididthattravel

  
  

• Sav — Smile Shield
  A dad with an idea to help families actually brush, not just mean to. We turn good intentions into a movement you can feel — the kind that makes a kid proud to show their grin.

  IG: sav160

  TT: Smileshielduk

  Web: smileshield.co.uk

  
  

• William Matthews — Oyster Holiday Cottages
  A small team on a windy coast trying to build something that feels like home. We talk about hospitality as love: welcome notes, off-season memories, and leaving a place better than you found it.

  IG: Oyster Holiday Cottages

  
  

• Declan Natras — From the Army to founder
  Standing on the edge of civilian life with a head full of ideas. We talk about courage in quieter forms: buying back your time, making your first £1k, and choosing the long road on purpose.

  
  

• Lily (14) — Future sports broadcaster
  A teenager with a voice that belongs at the match. We sketch the first steps of a dream most adults are too shy to say out loud — and promise to check back soon.

  TT: lily.gallagher74

  
  

Follow Simon Says on Spotify and subscribe on YouTube.
Your support helps us fix the education system, teach people business, and give knowledge away for free.

Sponsored by HighLevel
This episode is sponsored by HighLevel — the all-in-one platform for funnels, CRM, marketing automation, and lead management.
With my link, you get 30 days free.

👉 Start your 30-day free trial here: https://www.gohighlevel.com/simonsays

—

In this episode of Simon Says, Simon Squibb helps four callers turn raw intent into real plans — from wildlife photography to wellness retreats.

• Hiran , @hiranmano— NYC technologist with a wildlife-photography dream. We scrap the “non-profit” label, set a $4,000/month client target in 6 months, and map revenue paths: paid shoots (zoos/NGOs/brands), print sales, a photo book, and gear sponsorships.

• Philip Gidding — Electrician launching a pie-and-mash shop with a pay-it-forward model. We design a zero-budget launch: niche first (serve trades), film taste-test reactions at wholesalers, partner for in-store sampling, and use content to drive preorders.

• Allegra Melloul, @a1legra — Paris-based creative torn between film, teaching, and service. We focus the mission: make the Divine Comedy film trilogy in Italy, fund impact work (orphans) via profit, and keep a small content-services roster for runway.

• Janine Hanlon, @janinehanlonlivingwell — Building affordable women’s wellness retreats. We kill limiting beliefs, expand beyond IG to TikTok/YouTube, and execute a revenue-share weekend pilot with an existing venue, then use profits to underwrite free places.

Follow Simon Says on Spotify and subscribe on YouTube.
Your support helps us fix the education system, teach people business, and give knowledge away for free

Sponsored by HighLevel
This episode is sponsored by HighLevel — the all-in-one platform for funnels, CRM, marketing automation, and lead management.
With my link, you get 30 days free.

👉 Start your 30-day free trial here: https://www.gohighlevel.com/simonsays

In this episode, Simon Squibb speaks with four young dreamers who are already challenging the system:

• George Pemberton (16) — wants to launch a hybrid athlete coaching business with his brother. We design a hook (“Get fit for free”) and debate whether he should pursue A-Levels or take a gap year to go all-in. (@nobs.club • @exalt_ekene)

• Francesca O’Sullivan — shares her raw story of losing her son and feeling lost after redundancy. In a 2-minute challenge, we explore how pain can become purpose, and how her writing could grow into a community. (@frankiesaturn)

• Harrison Nott (15) — already turned over £100K with his invention CoolTowel™. We unpack how to balance scaling a product business with building a personal brand that inspires millions. (@harrisonnott)

• Pijus Pranckus (18) — building a “Siri for business” to transform how companies train staff. We drill into clarity, focus, and how to pitch without losing people in the detail. (@jpcustomsie)

• Julia Hammond (18) — launching Haya, a modest fashion brand redefining style and accessibility. We map out low-cost launch strategies, from TikTok to “modest marketing” campaigns. (@hayacollectionca)

Follow Simon Says on Spotify and Subscribe on YouTube.
Your support helps us fix the education system, teach people business, and give knowledge away for free.