Twenty years ago I was saying things that nobody wanted to hear, to rooms that were not full, about a subject most organisations considered optional.
Not opposed. Just uninterested. Silence, rather than argument.
That, more than any recession or any backlash, is the thing that ends businesses like mine. Not the fight. The indifference.
So instead of a highlight reel, here are twenty-one lessons from twenty years. Some of them flatly contradict each other. That is not a mistake, it is the honest answer. The craft is not knowing the rules. It is knowing which rule today is asking for.
The years nobody sees
1. Be stubborn. Expect rejection. Expect empty rooms and unanswered emails and a market that is not ready. Then say it again. Resilience is not a mood, it is something you build on purpose, before you need it.
2. Survive the backlash. In twenty years the language has changed multiple times. And now, in some rooms, no word at all. The work did not change. Only the willingness to name it. Stay.
3. Values are cheap in the good years. They cost you nothing when the pipeline is full. They are the only navigation you have when it is dark.
4. Rest is a business strategy, not a reward. Holidays, breaks, time out, retreats. Not because you have earned them. Because there is no twenty year business without them.
Move towards the thing that scares the market
5. When everyone runs, walk towards it. The conversation about AI was fear. AI is coming for coaching. AI is coming for all of us. We could have gone quiet. Instead we started a podcast to go and find the people using AI to advance fairness. There were more of them than anyone expected.
6. Never stop being a student. Twenty years in, I went back to the classroom for MIT’s AI Strategy and Leadership programme. Expertise has a shelf life. Curiosity does not.
7. Reinvent without drifting. Change the offer as often as the world demands. Never change the compass.
8. Say it out loud, on the record. Your thinking is not a by-product of the business. It is the engine. Write the blog. Publish the white paper. Record the episode. Put your name on it.
Nobody builds alone
9. Hire for the season you are in. Some people are exactly right for now and not right for later. That is not a failure of judgement. It is a stage of growth, and pretending otherwise costs everyone.
10. Get an advisory board before you think you deserve one. Find people who have already done the thing you are trying to do. Our advisory board moved this business further than any strategy day ever has.
11. Collaborate with people who are going where you are going. Not the loudest. Not the best connected. The aligned.
12. Work with your family, carefully. I have written a book with my daughter: AI For Equity. Everyone will tell you not to. Sometimes they are right. Sometimes you build something neither of you could have built alone.
What you refuse
13. Do not chase the money. Chase the mission. In my experience the money tends to follow the people who were not chasing it.
14. Walk away from work that does not align. The revenue you decline shapes your business more than the revenue you accept. And yes, read this one against lesson 1. Stubbornness in the wrong place is sunk cost. Walking away in the wrong place is turning back when you are nearly at the finish line. Nobody can give you the rule. You earn the judgement by getting it wrong a few times and paying attention.
15. Build for the long term. Quick wins are somebody else’s business model.
16. Relationships compound. Some of the people we work with have known us for fifteen or twenty years. That is not networking that is relational, aligned and meaningful.
What it is all for
17. Give it away. Rocking Ur Teens is thirteen years old and has touched the lives of around three and a half thousand young people. It has never been a revenue line. It has always been the point.
18. Go beyond your shores. India this year. Ghana later this year. Clients in the US. A global view is not a luxury purchase. It is a better lens on your own market, and a reminder that wisdom is not concentrated in one postcode.
19. Build things that do not need you. A business that only works when you are in the room is a job with better branding.
20. Stop and mark it. Earlier this month we celebrated twenty years at the House of Lords. 120 people. Clients from the very first year. Family. Friends. People who said yes when there was no reason to. I had not realised how much I needed it. You cannot see twenty years of impact from inside the week. You have to stop, look up, and let other people tell you what you built.
Bonus
21. Do not trust this list. Every twenty year retrospective is written by someone who made it to 20 years. You are not hearing from the equally talented people who ran out of money in year four. I do not know which of these were wisdom and which were luck, and neither does anyone else who writes one of these. Take what is useful. Leave the rest. Then go and get it wrong in your own way, because that is the only part that actually teaches you anything.
One ask.
Our third book, AI for Equity, is published by Emerald on 27 October and is available to pre-order now. It is co-written with my daughter, and it is about the people already using AI to solve some of the hardest equity problems in the world, mostly at the edges, mostly without permission.
