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SIDE HUSTLE Blog


The real cost of trying to be everything at once
By Alan W One thing I keep noticing, in my own work and in the businesses I spend time with: the moment you try to communicate everything, you communicate nothing. It happens easily. You start solving one problem. Then you notice three more problems next door. You can genuinely help with those too. So you expand — the offer, the message, the positioning. And before long, nobody quite knows what you do, including, sometimes, you. This is not a strategy failure. It's a clarity
Apr 212 min read


Small course corrections.
By Alan W You don’t always need a new strategy. Sometimes you just need a small course correction. Although I’m using a platform business model in this example, the principle applies to almost any business. Things change while you’re building. Customer behaviour changes. Demand changes. Supply changes. Priorities change. If you don’t notice it early enough, you can end up solving the wrong problem. I think of it like a pilot flying from Johannesburg to Cape Town. If the wind
Apr 142 min read


Joel’s story on… a mobility revolution
Cars sat idle in driveways across Kenya while Joel spent nearly two weeks trying to rent one for his mother's visit. The disconnect would have been funny if it weren't so frustrating. But for Joel, that frustration sparked something bigger - a vision for Moti , the mobility platform that's now connecting thousands of vehicle owners with renters across Kenya and preparing to expand globally. His entrepreneurial journey began long before this moment, but this was when everythin
Dec 23, 20254 min read


Kamogelo’s story on… a mission to revive indigenous superfoods from Botswana’s garden to the world’s table
Growing up as one of six children in Botswana, Kamogelo discovered her calling early - in the dirt of her backyard garden, where she'd spend hours experimenting and nurturing whatever she could grow. Agriculture was mandatory at school, a subject most students endured rather than enjoyed. But for Kamogelo, it was sacred ground where she could do what she loved most. She tended to her spinach, beans, and onions with care that made hers stand out among all the others. This was
Nov 26, 20254 min read


Nicki’s story on… shaking up stale categories with the future of fun, flavour & innovation
Nicki discovered her passion for food in her grandmother's kitchen in Zimbabwe. Cooking, baking, and experimenting with food were the threads running through her childhood. Yet everyone saw her as the opera singer. She knew differently. Food was her future, not the stage and to many people's surprise, she took the unexpected path: food science, nutrition and dietetics followed by a postgraduate in education. It was, however, her part-time work as a student where she got her r
Nov 3, 20254 min read


AI as a Teammate → Why Specs & Context Matter
By Alan W AI is changing how we build, code, and design. But here’s the catch: it’s not just about speed or automation. From my own...
Oct 3, 20251 min read


Solving Hidden Challenges Builds Trust
By Alan W One of the biggest lessons I’ve learned as a platform founder and advisor is this: Your sellers will quietly reveal the...
Sep 23, 20251 min read


Refilwe’s story on… combating energy poverty with purpose and passion
Refilwe’s early childhood experiences deeply influenced the mission she would eventually pursue. Witnessing domestic abuse, she saw her...
Sep 17, 20254 min read


Here are a few ways I’m seeing AI shift things for Platforms/Marketplaces.
By Alan W Emerging Innovations in Marketplaces: AI as Foundational Infrastructure. AI isn’t just an add-on anymore. It’s becoming...
Sep 9, 20251 min read


Isaac’s story on… building a career development ecosystem for Africa
Isaac describes his journey as the shedding of various identities, each of which has shaped him into the founder and leader he is today. A journey of transformation that has empowered him to find his true passion, cultivate resilience, and make a meaningful impact on others through his mission-driven work. “If only we believed in ourselves earlier on in the journey. I realize now that nothing else truly changed; it was simply a matter of having self-belief. Once that confiden
Sep 8, 20254 min read
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