From Paper Rounds to Pitch Decks | Childhood Dreams, Big Hustles & the Investment Dilemma

We dig into the complicated world of entrepreneurship - from childhood side hustles and early money lessons to investment readiness culture, the “cult of startups”, and what it takes to grow a business without losing yourself.

Aiwan shares how her grandma in Nigeria shaped her business mindset growing up on a council estate in London - and how visiting her Auntie Margaret’s market stall in Balham inspired her to pursue a “work for herself” path that would eventually lead to founding her creative media production company, AiAi Studios. Tamanda reflects on earning £400 a day in her early twenties, and why she still walked away from traditional career paths to build something on her own terms.

We wrestle with the big questions: Would you take a million pounds from Steven Bartlett? What if education doesn’t work - especially for Black and working class communities? Why are Black women still the least likely to get funding and investment? Can you scale a business without selling out — or burning out?

This episode is about ambition, agency, and building something real in a world that still doesn’t expect us to succeed.

In this episode:

• Would you take £1M from Steven Bartlett? We talk trade-offs, temptation, and power.
• Aiwan’s business mindset - from her grandma’s grind to Auntie Margaret’s market stall in Balham.
• Tamanda on earning £400 a day in her twenties - and why she still walked away from traditional career paths.
• Side hustles, childhood paper rounds, and the early money lessons that shaped how we work.
• The “Black tax” and the pressure to share your earnings, even when you’re building something fragile.
• Why education felt like a dead end - and what pushed Aiwan to start her own ventures.
• When investment readiness starts to feel like a trap - or a cult.
• What it takes to grow without losing yourself: perfectionism, control, delegation and all the rest.
• Can Black women scale a business without selling out - or burning out?

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