At last month’s CEO Fireside Chat in Joburg we chatted to Alex Thomson, CEO and Co-Founder of Naked Insurance, regarding reinventing insurance, raising R700m, and scaling Naked Insurance.

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Here were the key takeaways:

▼ Growth thresholds are real - Many businesses hit their first operational strain around the 20–25 person mark.

▼ Choose the right investors - Look for partners with deep pockets, open funds, and the willingness to grow with you. Invest in those relationships; they matter more than you think.

▼ Lean into difficult conversations - Whether it’s an investor feeling undervalued or an awkward internal issue, addressing it early makes all the difference.

▼ Confidence counts - Even great founders can struggle with imposter syndrome, but stepping into unfamiliar areas (marketing, tech, etc.) is often part of the journey.

▼ Hire slowly, hire right - The temptation to fill a role quickly is high, but hiring the wrong person is far more expensive than waiting for the right one.

▼ South Africa is tough, but full of opportunity - Despite operational and socio-economic challenges, the upside for those who push through remains massive.

▼ Founder and team relationships need active management - Confidence, clarity, and alignment are essential to keeping teams and investors committed.