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 andthe 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 Intro
02:13 How Smileys Started
08:27 Becoming the Top Athleisure Brand in Africa
13:56 Impact of a Founder’s Passion on a Brand
14:40 Dealing with CopyCats
17:54 Going from Bootstrapping to Scaling
19:02 How Smileys Started Making Sneakers
23:01 Understanding Product Market Fit
27:30 The Basics of Starting a Business
28:03 Habib Beyond Smileys
32:23 Life in the UK
37:09 Why SMEs are Important to the Economy
38:43 Raising Capital & Funding
41:35 Managing 9-5 & Running a Business
45:10 Understanding the Power of Leverage in Business
49:10 Quick Fire Questions
55:57 Habib's Favourite Smileys Product
57:51 Future Plans for Smileys
1:00:53 Habib's Advice If You Want to Start a Business
1:02:49 Is Dim Smileys' New Brand Ambassador?

📑 JOIN THE 6 WEEK BUSINESS SERIES - https://diimejii.myflodesk.com/

🔗 CONNECT WITH HABIB
https://smileys.africa/
   / @whoishabyb  
  / whoishabyb  
  / whoishabyb  
  / whoishabyb  

🔗 CONNECT WITH DIM
   / @diimejii  
  / diimejii  
  / diimejii  
  / diimejii  
https://www.diimejii.com

MUSIC USED
Song: Building Wonders v1
Artist: Gramoscope Music
Source: https://gramoscopemusic.sourceaudio.c...
License: By MINT_BMG, SourceAudio Holdings (music publishing).

🎙 ABOUT THE PODCAST
Figuring Life Out Podcast explores life's endless possibilities, delving into topics like growing mindsets, building better habits, and navigating the complexities of existence. Through playful yet probing dialogue with founders, CEOs, entrepreneurs, creatives, and thought leaders, Dim brings you insights that inspire, motivate, and ultimately help you on your journey to figuring life out.

Want to start your own business? We use Tide! https://www.tide.co/partners/heptabra...

🎧 LISTEN FOR FREE
⁠Apple Podcasts⁠ https://podcasts.apple.com/ie/podcast...
⁠Spotify⁠ https://open.spotify.com/show/1ZT3OTE...
⁠RSS⁠ https://anchor.fm/s/fb0eb914/podcast/rss

🙏🏽 LEAVE A REVIEW
If this episode resonated with you, leave a 5-star review on Apple Podcasts or Spotify, it helps others find 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 for tuning in.

PS: Some of the links in this description are affiliate links that I get a kickback from 😜