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?Please rate, review and subscribe for weekly episodes.Connect with us on:TikTokInstagramLinkedInAiAi StudiosRoots & RigourThis is an AiAi Studios Production©AiAi Studios 2025 Hosted on Acast. See acast.com/privacy for more information.