I'm building two companies that share nothing on the surface: an affordable school network in Kenya, and RoundOS, an AI fundraising operator.
Companies rarely fail for lack of information. They fail when decisions stay vague and nobody owns them.
I write about that.
If I ran this raise again, I'd build the system before the pipeline.
Not the deck, not the list. The boring plumbing that catches a dropped reply, a promise, a fund mentioned once on a call.
The founders who close aren't the best pitchers. They're the ones who don't leak.
Buried in my own round, I dumped it all, emails, calls, LinkedIn, into an AI to find what I'd dropped. It found a missed investor and a stale deck request in minutes.
That's when I stopped white-knuckling my raise and ran it like I had a chief of staff. That became RoundOS.
I've raised through a market that froze overnight. One year capital was everywhere, the next nobody picked up.
Never confuse a warm market for a strong company. The terms you can get aren't the business you have.
Raise like the window shuts tomorrow. Sometimes it does.
On a call, someone mentioned a fund in passing. We'd discussed a dozen, and I forgot it the moment we hung up.
Weeks later I found it again. Perfect fit, nearly lost to my memory.
Your best lead is often something you already heard and never wrote down.
Building two companies, the cost nobody prices in is context-switching.
Raising while running a school means every investor thread competes with a broken bus and a quit teacher. The investor only sees the slow reply.
Fundraising punishes the founder with the most going on.
An investor asked me to send the deck. The message sat two weeks before I saw it. By then it was cold.
I sent it anyway, with an apology. He's reading it now. One honest follow-up revived a dead thread.
Most 'lost' investors aren't lost. They're buried.
In a raise, most contacts are replaceable. A few aren't: the people who can open a door.
Those threads you can't let go cold, and they're exactly the ones a tired founder drops first.
The relationships that matter most get the least attention. Guard them.
By 2050, almost 40% of the world's children will live in Africa.
That is why I build schools here. Whoever educates that generation doesn't run a charity project. They shape the century.
I don't see a bigger market or a bigger stake.
In China I saw a chemistry class where an AI watches each desk and catches the mistake a teacher used to walk over for. One teacher now runs a room of a hundred.
AI's first job in education is uncapping how many students one good teacher can reach.
At scale, the fastest way to fix economics was to grow the share of revenue from your highest-margin format. We kept the expensive one-to-one product and shifted weight to formats where one teacher served many.
Mix is a lever most founders never touch.
1/ For years I ran a large company through one crisis after another, until crisis stopped being an event and became the climate we lived in. It changed how I think about strategy.
5/ When you're stuck, look sideways. How other industries survive a downturn rhymes more than people expect. The basics of handling a crisis don't care what you sell.
A father toured our school while his wife did the forms. He skipped the teaching and counted the fire exits.
Where families have lost kids to unsafe buildings, safety is the product and pedagogy the bonus. Their first question is rarely the one you prepared for.
To turn one school into a network, I need two things. A repeatable model with predictable payback, so a campus is a template, not a gamble. And graduates measurably better.
Without the first, growth is chaos. Without the second, it's just more buildings.