May Contain Jab
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Episode 3

Strategy Over Tactics in an AI-Driven World

September 14, 2026 ·45 min

Strategy is the address in the sat nav. Tactics are the turns. May and Jab explain why owners need a clear direction before AI and automation can pay off.

Show Notes

New AI tools launch every week, and every one promises an edge. In this episode of May Contain Jab: The Owner's Edge, Jab and May argue that most owners are asking the wrong question. The question isn't which tool to use. It's where the business is going.

Jab explains strategy as "the address you put in the sat nav", with tactics as every turn along the way. May shows why automation only works once the strategy and the process are in place. Along the way they cover busywork, shiny object syndrome, and why AI education has to come before AI implementation.

  • Why strategy means choosing one direction and ruling out the others
  • The difference between a strategy and a to-do list
  • May's lesson from an outreach push with no clear ICP
  • Jab's SOSTAC walkthrough, told through a dating app analogy
  • The real automation unlock: strategy, then process, then automation
  • Using AI as a "ruthless mentor" to stress-test your plan
  • Amazon, eBay and low-cost 24-hour gyms: strategy beating bigger budgets
  • What breaks first in a business with all tactics and no strategy
  • When to stop doing everything yourself
  • A quick-fire round: strategy or tactic?
  • Jab's hot take on AI health and safety for teams

00:00 Cold open: Jab's dating app strategy

01:15 Welcome: strategy over tactics

02:21 Strategy is the address in the sat nav

04:22 Strategy vs a plan or to-do list

05:30 When busy isn't strategic

07:03 SOSTAC, explained through dating

09:48 The simplest strategic decision a founder can make

10:24 What owners must do now AI is a partner

12:01 The real automation unlock

12:46 Scenario: "AI can help me sell a million of these"

15:35 Does an MBA or consulting background help?

16:55 Can AI replace strategic thinking?

19:38 Strategy beating better-resourced competition

22:46 The most common strategic mistake

26:20 All tactics, no strategy: what breaks first

26:58 When to stop doing everything yourself

29:19 Looking after yourself to make better decisions

30:56 Strategy vs tactics: the field and the chessboard

33:31 Questions to ask: SWOT and Ikigai

35:08 Quick-fire round: strategy or tactic?

36:43 AI implementation or strategy first?

37:31 Hot take: the AI health and safety inspector

40:53 "I don't have time for strategy"

42:46 Two questions every owner should ask

44:05 Where to find May and Jab

01:15 is estimated from where May first speaks. All other times are taken directly from the latest cut.

 Strategy Over Tactics in an AI-Driven World

A new AI model drops every other week, and each one promises an edge. So most owners ask the same thing: which tool should I be using?

In Episode 4 of May Contain Jab: The Owner's Edge, Jab and May say that's the wrong question. The better one is simpler: where are you actually going?

Strategy is the address. Tactics are the turns.

Jab's way of explaining it is that strategy is the address you put in the sat nav, and tactics are every left and right turn it takes to get there. Choosing Portugal also means you are not driving to Wales, Scotland or Northampton on the same trip.

May thinks of it as a map. Without one, you get pulled one way and then another, and you end up right where you started.

Busy is not the same as strategic

Both hosts admit they've fallen for this. May ran an outreach push without a clear ICP, and it took her weeks to realise she was "generating noise to generate noise." Jab remembers a campaign where extra content, made for one specific persona, was repackaged for a launch it was never built for. It didn't land. It was a square peg in a round hole.

Strategy, then process, then automation

This is May's core point, and it's where most owners get the order wrong:

  1. Know your direction.
  2. Work out what's already working and turn it into a repeatable process.
  3. Only then add automation.

With that order in place, a process can run overnight, 24/7. Without it, you just automate chaos.

AI still has a job before that point. May uses it for brainstorming and ideation. Jab uses it as a sparring partner, prompting it to act like a ruthless mentor and point out the flaws in his plan. Either way, a human stays in the loop.

Lessons from bigger players

Jab was at eBay when Amazon doubled down on vetted sellers and a reliable customer experience. He also points to the low-cost 24-hour gyms that reshaped fitness by knowing exactly who they were building for. The lesson from both is to pick a direction and stick with it long enough to see results.

The mistake that costs the most

May calls it shiny object syndrome: saying yes to work next to your core offer until you're stretched thin and have no direction left.

Jab's version is copying a tactic blindly, often from someone with far deeper pockets and a bigger team. His advice is to look inward first. If you don't have the resource to keep something going over time, it isn't your strategy.

The hot take: education before implementation

In the quick-fire round, May says education has to come before AI implementation. Jab goes further. He's seeing emails and documents that nobody should have signed off, and brands losing trust as a result. "I am the AI health and safety inspector here," he says. You wouldn't hand someone a knife without showing them how to use it, so train your people first.

Two questions to ask every week

May closes with two questions:

  1. Am I still steering the ship in the right direction?

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