Hey Startup Leapers 👋
It’s been a while (since August, to be exact), but we’ve been hard at work behind the scenes, dropping some of our most compelling founder conversations yet. If you’ve been quietly listening, we see you. If you’ve been waiting for this newsletter to return, same.
Here’s our recap of 2025 episodes, Yvonne and Maria share top founder lessons and favourite moments from last year…
As we gear up for a bigger 2026, we’re sharing our last three founder stories about: grit, clarity, and building the hard things and sharing real lessons you won’t find in the books.
From reimagining logistics in Africa, to flipping the script on building purposeful brands in the UK, to scaling AI-powered pet insurance in Sweden, these are founders who didn’t wait for permission and share the real, wiggly journey of their startup leap so you may chart yours with a bit more confidence.
Let’s get into it👇🏾
🔶 Miishe Addy – Co-Founder & CEO, Jetstream Africa
What happens when a Bain consultant moves back to Ghana and tries to fix intercontinental trade? You get Jetstream: a digital freight forwarder now combining logistics + embedded trade finance, and doing it profitably.
🔑 Key Takeaways:
On raising capital: “There are two ideal times to raise: before you’ve done anything, or once traction is undeniable.” (24:00)
On resilience: Jetstream went from 23% loan default rates to 0% — by embedding finance where it actually works: alongside physical cargo movement. (11:00–12:00)
On founder mindset: “You can't copy Silicon Valley here. You have to think independently — and have the stomach to prove people wrong.” (17:00, 19:00, 21:00)
On fundraising: “Some investors were pulling their hair out when we pivoted into fintech — but we knew what the market needed.” (10:00–15:00)
On expansion: “There are no easy wins in Africa. Pan-African success requires time, deep partnerships, and local credibility.” (33:00–35:00)
🔷 David Olusegun – Founder, Creative Control Ventures
From music management to venture building for purpose led brands from SYPS, to NALA’s Baby. David shares some gems on building truly lasting purpose led brands using real-life examples and lessons, this is a must watch for any founder building in the Consumer Packaged Goods space.
🔑 Key Takeaways:
On ownership: “Artists build billion-dollar companies, but too often, they own none of it. That’s what we’re changing.” (06:30)
On infrastructure: Building shared resources for creators to launch businesses without reinventing the wheel. (13:50)
On the shift: Why he moved from label-side into venture investing, and how he's backing the next wave of creator-led startups. (22:00)
🔹 Hedda Båverud Olsson, Founder & CEO, Lassie
Hedda left McKinsey and turned a side idea into one of Europe’s fastest-growing insurtechs, rethinking pet insurance with AI and preventative care.
🔑 Key Takeaways:
On Fundraising: “Don’t ask for money, ask for advice”
On market fit: “Pet insurance is broken. We made it proactive — not just reactive.” (15:30)
On trust: “Winning in insurance means building long-term trust — not short-term transactions.” (05:00)
On raising: $70M+ in funding later, Hedda breaks down how to pitch when you’re going up against legacy players. (27:00)
📢 Help Shape The Startup Leap in 2026
We’re rethinking how we serve this community, and we want your input as we plan for 2026!
What kinds of founder stories do you want more of? What format would be most helpful to you? playbook episodes, deep-dive interviews, Q&A AMAs, behind-the-scenes lessons? Conversations with operators, and VCs too? Live vibe coding sessions? Or Live Pitch Demos? Dilemma only episodes? Is there a guest you’d love to hear from?
Hit reply and tell us. We read every message.
You can also send us an email on [email protected]. We look forward to hearing from you!
✨ Startup building is hard. We're here to make it just a little bit clearer by sharing real founder stories, and lessons you can learn from. Catch up on all past episodes here:
Here’s to bigger leaps in 2026 🪂
What was your favourite startup lesson of 2025?
– Maria & Yvonne.
📚 Interesting Reads & Resources
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