Fundraising luck: Rakuten Series A arrives pre-COVID

In this week’s episode, we’re joined by Ahmet Bahadir Ozdemir, the self-described “accidental telecom guy” and co-founder of Airalo, the eSIM marketplace that’s quietly rewiring how travelers get online around the world.

Bahadir shares the wild, very human journey that led from hustling ship supplies out of his parents’ home in Turkey — pretending to be “60 different people” across ports worldwide — to building SIM4Crew for the 1.7M+ seafarers out there, killing his own profitable business the day Apple announced eSIMs, and then riding out a total revenue collapse during COVID with nothing but a fresh Series A and a “war on waste” mentality.

What emerges is not just a startup story, but a philosophy: on luck and timing, on building with kindness in a hyper-capitalist system, and on why individual stories matter more than any KPI.

In this episode, we explore:

* The accidental telecom founder — how a ship-supply side hustle turned into SIM4Crew, a global SIM card for sailors, after every captain started asking for “potatoes, tomatoes… and SIM cards.”

* Seeing the pain in maritime connectivity — why 1.7M seafarers living 9 months at sea were the perfect “edge case” to reveal just how broken roaming really is.

* Paying $1,000 for a crash course in roaming — the scrappy way Ahmet taught himself telecom from scratch and launched his first global SIM business using a warehouse network he’d already built.

* Killing your own golden goose — the moment Apple announced eSIM iPhones on September 28, 2018, and why Ahmet immediately decided to disrupt SIM4Crew by building the “Amazon of eSIMs” instead.

* Breaking into telco as an outsider — from being told his tiny booth looked “cute” at a Netherlands industry event to convincing one visionary operator to give Airalo pay-as-you-go access with no deposit… a relationship that later turned into hundreds of millions in revenue.

* Doing the things that don’t scale — wearing Airalo t-shirts everywhere, staged elevator phone calls pitching “this eSIM thing,” and anonymous social media accounts replying to every roaming complaint with, “Sorry to hear this — have you tried Airalo?”

* When performance marketing fails — how burning cash on Facebook and Google exposed a deeper problem: nobody knew what an eSIM was — and why influencer-led education finally unlocked explosive word-of-mouth growth.

* Dancing on the edge of default alive — the candid story of burning ~$200k/month, getting a tough P&L review from Sequoia, pulling Series A forward to late 2019, and landing $5.4M from Rakuten and other investors literally weeks before COVID froze global travel.

* Surviving zero revenue and constant panic attacks — what it felt like when revenue on Stripe dropped to zero, why Ahmet started “visiting the emergency room just to feel safe,” and how a ruthless “war on waste” kept the company alive through two lost years.

* A people-first philosophy in a KPI-first world — Ahmet’s critique of “greater good” capitalism, why statistics mean nothing to an individual trying to pay rent or bury a loved one, and how Airalo is built around psychological safety, rare firings, and the mantra: “a bunch of common people putting out uncommon results.”

* Travel, empathy, and connection — why he believes every connection starts with a conversation, what talking to taxi drivers teaches you about the world, and how Airalo’s real product is peace of mind when you land in a new country.

* The long-term vision for Airalo — turning the company from a visible app into an invisible global layer where every gigabyte — whether bought through an airline, a fintech, or a mom-and-pop travel shop — quietly runs on Airalo’s infrastructure.

Plus much more — from panic days in fundraising, to the emotional cost of leadership during crisis, to what it really means to build a humane company in a brutal, winner-take-all market.

If you care about timing, resilience, and building for humans — not just for charts and decks — you’ll get a lot from this one. Enjoy the episode!

Also available on Apple Podcasts // Spotify

Chapters

(0:00) Intro(3:40) Building A Global Telecoms Company (11:28) The Timing Was Just Perfect (14:10) Partnering With Network Providers Globally (19:23) Having Great Partners Early (21:47) Finding Those First Super Users (27:00) The Signs Of Building A Unicorn (28:58) The COVID Panic Day (34:30) How We Got Through COVID (39:18) Being A Caring Person (53:29) The Big Impact & Road Ahead

Thanks for listening and see you in the next episode 👋

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