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Figuring Out Entrepreneurship | Habib Olawale on Building a Million-Athleisure Brand from ₦16K
"We didn’t set out to build ‘Nigeria’s top athleisure brand’—we just wanted socks that didn’t cost a fortune but felt premium. Back then, it was just about solving a simple problem: why should quality basics be a luxury?"
Wasulu Habib is the founder of Smileys Africa, a homegrown success story that turned smiley-face socks into a movement. What began as a side hustle importing affordable hosiery is now redefining how Nigerians experience everyday fashion—one intentionally designed product at a time.
In this episode, Habib pulls back the curtain on:
The unsexy truth about bootstrapping in Nigeria’s volatile market
How to spot gaps everyone ignores (and turn them into empires)
Why copycats became his unexpected validation
The emotional ROI no business book teaches (hint: it’s not revenue)
If you’ve ever doubted whether your “small idea” could scale, or wondered how to build customer love beyond transactions, this conversation is your blueprint.
Enjoy :)
Chapters: 00:00 Intro02:13 How Smileys Started08:27 Becoming the Top Athleisure Brand in Africa13:56 Impact of a Founder’s Passion on a Brand14:40 Dealing with CopyCats17:54 Going from Bootstrapping to Scaling19:02 How Smileys Started Making Sneakers23:01 Understanding Product Market Fit27:30 The Basics of Starting a Business28:03 Habib Beyond Smileys32:23 Life in the UK37:09 Why SMEs are Important to the Economy38:43 Raising Capital & Funding41:35 Managing 9-5 & Running a Business45:10 Understanding the Power of Leverage in Business49:10 Quick Fire Questions55:57 Habib's Favourite Smileys Product57:51 Future Plans for Smileys1:00:53 Habib's Advice If You Want to Start a Business1:02:49 Is Dim Smileys' New Brand Ambassador?
📑 JOIN THE 6-WEEK BUSINESS SERIES W/ HABIB & I
https://diimejii.myflodesk.com
🔗 CONNECT WITH HABIB
📸 Instagram💼 LinkedIn🌐 Smileys
🔗 CONNECT WITH DIM
📸 Instagram🐦 Twitter📺 YouTube💼 LinkedIn🌐 Website
🎙 ABOUT THE PODCAST
Figuring Life Out explores life's endless possibilities, digging into mindset, creativity, career pivots, and building better habits. Through real and reflective conversations with founders, creatives, and thought leaders, Dim brings you insights to help you grow and navigate the unknown.
🎧 LISTEN FOR FREE
🎙 Apple Podcasts🎧 Spotify📡 RSS
🙏🏽 LEAVE A REVIEW
If this episode resonated with you, leave a 5-star review on Apple or Spotify. It helps more people discover the show and keeps it going 🙌🏽
👋🏼 LET’S CONNECT
Tweet your thoughts @diimejii. I’d love to hear what stood out to you and thank you personally for tuning in.
PS: Some of the links above are affiliate links, so I get a little kickback if you click and buy — appreciate the support 😜
View all episodes
By Oladimeji Ajegbile"We didn’t set out to build ‘Nigeria’s top athleisure brand’—we just wanted socks that didn’t cost a fortune but felt premium. Back then, it was just about solving a simple problem: why should quality basics be a luxury?"
Wasulu Habib is the founder of Smileys Africa, a homegrown success story that turned smiley-face socks into a movement. What began as a side hustle importing affordable hosiery is now redefining how Nigerians experience everyday fashion—one intentionally designed product at a time.
In this episode, Habib pulls back the curtain on:
The unsexy truth about bootstrapping in Nigeria’s volatile market
How to spot gaps everyone ignores (and turn them into empires)
Why copycats became his unexpected validation
The emotional ROI no business book teaches (hint: it’s not revenue)
If you’ve ever doubted whether your “small idea” could scale, or wondered how to build customer love beyond transactions, this conversation is your blueprint.
Enjoy :)
Chapters: 00:00 Intro02:13 How Smileys Started08:27 Becoming the Top Athleisure Brand in Africa13:56 Impact of a Founder’s Passion on a Brand14:40 Dealing with CopyCats17:54 Going from Bootstrapping to Scaling19:02 How Smileys Started Making Sneakers23:01 Understanding Product Market Fit27:30 The Basics of Starting a Business28:03 Habib Beyond Smileys32:23 Life in the UK37:09 Why SMEs are Important to the Economy38:43 Raising Capital & Funding41:35 Managing 9-5 & Running a Business45:10 Understanding the Power of Leverage in Business49:10 Quick Fire Questions55:57 Habib's Favourite Smileys Product57:51 Future Plans for Smileys1:00:53 Habib's Advice If You Want to Start a Business1:02:49 Is Dim Smileys' New Brand Ambassador?
📑 JOIN THE 6-WEEK BUSINESS SERIES W/ HABIB & I
https://diimejii.myflodesk.com
🔗 CONNECT WITH HABIB
📸 Instagram💼 LinkedIn🌐 Smileys
🔗 CONNECT WITH DIM
📸 Instagram🐦 Twitter📺 YouTube💼 LinkedIn🌐 Website
🎙 ABOUT THE PODCAST
Figuring Life Out explores life's endless possibilities, digging into mindset, creativity, career pivots, and building better habits. Through real and reflective conversations with founders, creatives, and thought leaders, Dim brings you insights to help you grow and navigate the unknown.
🎧 LISTEN FOR FREE
🎙 Apple Podcasts🎧 Spotify📡 RSS
🙏🏽 LEAVE A REVIEW
If this episode resonated with you, leave a 5-star review on Apple or Spotify. It helps more people discover the show and keeps it going 🙌🏽
👋🏼 LET’S CONNECT
Tweet your thoughts @diimejii. I’d love to hear what stood out to you and thank you personally for tuning in.
PS: Some of the links above are affiliate links, so I get a little kickback if you click and buy — appreciate the support 😜