Successfully Self-Employed
The Weekly Hotseat
Wednesday, 30 September 2026 · Issue #14
This week's Hotseat recap: what came up, what landed, what we're each holding each other accountable for doing next.
Community Update
This week in the room
The talk this week circled three main topics: whether a young business needs a website yet, how to use AI to strategize rather than just bounce ideas around, and the sometimes unique places founders are getting found these days.
Always plenty of honesty, a pinch of dark humour about the state of the world and the surprisingly strong South African rand; but overall, just founders helping founders in all their different stages of growth.
Key learnings and discussion points
What came up this week
Rethinking the need for a website, treating AI as a strategist, and the new ways founders are finding visibility.
A website isn't always the first thing a new business needs.
Having a web presence and having a website are two different things. Early on, a presence is enough, and a business can run on it for a good while.
But if your own website is more appropriate for what you do or supply :
●Domains are rented, not owned outright: You generally pay a yearly fee. A standard .com domain is usually only $10 - $20 a year.
●Attempting the build yourself? WordPress isn't for beginners: It's a modular engine you sit inside, with users, security and plugins to make it as functional as it is. Powerful, but better handed to someone else to build once the money's there.
AI as a strategist, not just a chat tool.
The most useful chunk of the conversation was around moving AI from "tell me this" to "help me plan." Nik has a real discipline around this, and it shifted a few perspectives. Some tips when moving from one stage of AI use to the other:
●Red-team it: Ask it to review its own answers for what could go wrong or what could be wrong with its advice. Nik does this on nearly every reply when sound boarding with his AI to ensure that no assumptions are being made on either side.
●Feed it context and firm rules, then let it strategise: Give it the background and the guardrails it needs, and it stops being a search box and starts being a sounding board.
●Lock a canonical document: Get it to summarise a long chat thread into a document, mark it locked, and use it as the single source of truth for new chats. Just a different way of creating a business context layer when you think about it.
●The paid tier is generally worth it: A $20 a month subscription came up as the one spend most don’t begrudge. Poe AI is also a free way to reach several models at once; and connecting your AI to your other tools such as Canva, Notion and Google Drive gets them talking to each other so you have to explain yourself less.
As Nik put it, the tool of choice is not the answer; it's how you get where you want to be.
Getting found is changing, and it's not where you'd expect.
The places where founders are getting discovered are shifting, and some of them are not the obvious ones.
●Reddit is powerful: A developer I know got banned from LinkedIn, moved to Reddit, and within a month was being recommended to people via ChatGPT. No personal brand, just showing up, bantering on Reddit, being useful.
●A portfolio page can beat a forced corporate identity: Plenty of founders skip the single company brand and run a portfolio page that links out to each project, as long as it's obvious how to work with them and how to book a call.
●Local still works: For a business serving a specific area, a community newspaper can out-target a social media ad for the people who actually live nearby.
●Product branding: Labeling that says what it does, how to clean or care for it, plus a QR code to your socials, could be the “word of mouth” or social media growth you need to further your trade.
This week's resources & community
Needs & Leads
●Free AI strategy call: Nik has kindly offered an AI coaching session to anyone in the group who wants help moving from chatting to AI to using it for strategising. Find him on our WhatsApp group to then drop him a PM.
●National AI survey goes live: A large-scale AI survey I've been working on with DayOne AI Professional Network goes live today, with a R10,000 prize drawn at random from all South African respondents. I'll share the link in the WhatsApp group soon for anyone who wants to take part.
●Notion Event: I'm running my first in person Notion event of the year in Cape Town on 27 October. It’ll center around using AI to sharpen your Notion operations. Both Nicola and Simone will be there. Nics for Ops support and Simone as a Speaker. For more details or to apply to attend for free (if you’re in Cape Town) click here! Space is limited.
Got something to offer or something you're looking for?
Post it in the Needs & Leads channel in the community and it'll get a spot in next week's newsletter.
Accountability
What we're each doing in the next week or two
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