Slipstream Strategy: The Power of Who You Ride With
- PG Geldenhuys
- 6 days ago
- 3 min read
This week’s newsletter is about the people you surround yourself with... and the conversations you choose to stay in.
I’ve been cycling for a long time. Long enough to know when I’m properly prepared, and when I’m bluffing a little. Going into this weekend’s 99er cycle race (my annual warm-up for the Cape Town Cycle Tour in March), I felt undercooked. Heavier than usual. January training goal technically ticked, but nutrition less so. A fair bit of travel. Business. Pleasure. Life.
To make things more interesting, last year went well. My times improved, my seeding jumped, and that meant lining up this year with a noticeably stronger bunch. That’s the double-edged sword of progress: better positioning puts you in faster company, and if you’re not ready, you get found out quickly.
Last year, I rode at the front far too often. Pulled more than I should have. Played hero when my legs hadn’t earned it yet. I got dropped late in the race, around the 90% mark…but still scraped home with a better time, which improved my seeding again. That decision last year created this year’s opportunity.
This year, I rode differently.
I stayed at the back. I resisted the urge to prove anything. I let stronger riders do the work they were clearly better suited to do. I’d rested properly in the days before the race. And, most importantly, the group worked beautifully together. Smooth rotations. Clear signals. No ego-fuelled nonsense. The 100 folks that started together stayed together the whole way, no breakaways. It was magic.
My lack of training finally caught up to me, but way later than I had expected. Around the 80 km mark of a 95 km race, I fell away on the hill… but that was 30km more than what I had expected at the start. The last 15 km were… character-building. Limp-home territory.
And yet, when the results came in, something interesting had happened. Despite feeling less prepared, I hit personal bests across multiple metrics. Better overall time. Stronger average pace. Progress - without bravado.
That’s the quiet power of the right group.
There is almost never a bad idea in surrounding yourself with people who are smarter, stronger, or more experienced than you are. They lift your game by default. Their pace stretches you. Their standards reset what “normal” looks like.
There is, however, a caveat.
If you haven’t done any of the work - if you haven’t trained, read, thought, practised - there comes a moment when you’re no longer part of the conversation. At that point, the wise move isn’t to bluff harder; it’s to bow out gracefully, go back to preparation, and earn your seat again.
Up to that point, though, the group will take you far further than you could ever go alone.
The old saying is often quoted: "If you want to go fast, go alone. If you want to go far, go together.” Cycling teaches a useful amendment: with the right group, you can go fast and far… as long as you know your role.
This dynamic shows up clearly in business, too.
Take Steve Ballmer at Microsoft. Fourteen years often labelled as mediocrity, especially when compared to the mythic arc of Bill Gates before him and the renaissance that followed under Satya Nadella. The easy narrative is that Ballmer failed and Nadella saved the day.
Reality is more interesting.
Much of what made Nadella’s tenure successful: Azure, cloud infrastructure, enterprise plumbing… the foundations were constructed under Ballmer’s watch. The domestiques did the hard kilometres. The foundations were laid. Nadella rode the final stages with intelligence and timing. Different roles. Same race.
Cycling teams understand this instinctively. The champion doesn’t win alone. Someone hits the wind. Someone controls the pace. Someone sacrifices their own result so the collective can go faster. And who’s laughing now? Ballmer’s personal fortune has skyrocketed with Nadella’s stewardship of the company.
PG’s Pro Tip:
Ask yourself this question, for bonus marks, write it down:
Who are the five people you spend the most time thinking with, working with, or being influenced by - and in what specific ways are they making you better, stronger, or faster?
And just as importantly: where might you need to do more work before you earn the right to stay in those conversations?
Progress rarely comes from solo heroics. More often, it arrives quietly, tucked into the slipstream of the right group, at the right pace, for long enough to change what you believe you’re capable of.
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