Episode Summary:
Joshua D'Souza's family has run safaris in East Africa for over 50 years.
After climbing Kilimanjaro and having a life-changing conversation under the stars at his cousin's coffee farm, Joshua knew he needed to digitize African travel.
What followed was a wild ride: regulatory threats that could have sent him to jail, moving his entire team to Tanzania, and eventually building CloudSafaris–the infrastructure now processing millions in travel inquiries and powers bookings for major platforms ike Travly.
In this conversation, Joshua gets real about:
Why African travel infrastructure is "only 1% built"
The moment TICO threatened $50K fines + jail time (and their response)
Navigating North American investors who said "we don't touch Africa"
What it's really like living with local operators and learning the business from the ground up
Their journey from 2 customers to millions in monthly inquiries
Why he'd "die for what he's building" (his words, not ours)
This episode is pure gold for anyone building for African markets, considering a diaspora entrepreneurship journey, or just curious about what happens when you take a massive infrastructure problem and tackle it head-on.
Key Topics:
African travel infrastructure challenges
Building in the diaspora vs. on the continent
Fundraising for Africa-focused startups in North America
Strategic partnerships and angel investors
The pivot from B2C to B2B travel tech
Connect with Joshua:
CloudSafaris: https://cloudsafaris.com/
LinkedIn: https://www.linkedin.com/in/joshua-d-souza-758b74132/
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Host: https://www.linkedin.com/in/damilolaoludumila/
Chapters:
0:00 - 5:30 Background: Waterloo, Family Safari Legacy
5:30 - 8:45 The Waterloo Startup Culture & Co-op Program
8:45 - 12:00 First CloudSafaris Attempt (2019) & COVID Pivot
12:00 - 22:00 Building Phros: Fitness Tech During Pandemic
22:00 - 32:00 Moving to Tanzania, Living with Local Operators & Learning the Business
32:00 - 41:00 The TICO Cease & Desist: $50K Fine + Jail Time Threat
41:00 - 45:00 Co-founder Relationships & Living Together
45:00 - 56:00 Finding Strategic Angels: Travly & Benjamin Fernandes
56:00 - 1:00:00 Why African Travel is "1% Built"
1:00:00 - 1:03:00 Competition: Uber Safari Launch & Market Response
1:03:00 - 1:09:00 5-Year Vision & Advice for Learning About African Markets
1:09:00 - 1:12:00 "I Would Die for What I'm Building"
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