How to Think Like a Strategist: Lessons from Soldier, CEO & Call of Duty Advisor John Hillen

Dr. John Hillen

Dr. John Hillen has seen it all – from jumping out of planes in military ops, to leading billion-dollar businesses, advising presidents, and even becoming a character in Call of Duty: WWII. But ask him what most businesses get wrong? Strategy.

In this episode of From Startup to Wunderbrand, we unpack real strategy vs. what most founders are actually doing (spoiler: it’s just budgeting). Dr. Hillen brings clarity, humour, and some serious intellectual firepower to the messy world of business strategy – and shows how even scrappy startups can outmanoeuvre global giants.

🧠 Strategy Isn’t a Plan – It’s a Way of Thinking

Hillen opens with a truth bomb: “Most companies think they’re doing strategy… but they’re just doing their annual budget.” Strategy, he says, is about facing the future – not just repeating last year’s numbers with a tweak.

“Real strategy is something new in the mix. Modest improvement from last year’s business plan? Not a strategy.”

Startups, scaleups, and even Fortune 500s often confuse goal-setting and planning with strategic thinking. The difference? Strategy links ideas, actions, and outcomes across time. It’s not “because it’s due Friday” — it’s “if we do this now, we can do this next quarter, and hit this goal by year-end.”

A book by John Hillen called The Strategy Dialogues, blue cover with two illustrated people in a conversation — The Strategy Dialogues by John Hillen

💬 Why He Wrote a Strategy Book as a Dialogue

Dr. Hillen’s book, The Strategy Dialogues, is built around fictionalised conversations – not a dry textbook. Why?

Because that’s how humans learn.

Socrates knew it. The Bhagavad Gita used it. So did Confucius. Strategy lives in the back-and-forth, where people challenge assumptions and connect dots.

Each chapter explores a different scenario: going international, repositioning after disruption, scaling a new business model. The companies are fictional, but the challenges are very real – and come from Hillen’s own experience as a CEO and strategy consultant.

🚀 Strategy for Startups: When to Start (and How Much Is Enough?)

Hillen is clear: strategy isn’t a big-company luxury. You don’t wait until Series C or IPO to start thinking.

You update your strategy:

When the market shifts (AI, regulation, consumer behaviour)
When you change direction (new products, new markets)
When you're ready to play offense, not just survive

He offers a killer line:

“You already have a strategy – whether you’ve articulated it or not.”

For early-stage founders, he suggests thinking “outside-in” (understand your market) and “inside-out” (know your strengths). The sweet spot? Where your dominant gene (e.g., product, service, speed) meets a shifting market opportunity.

📉 What to Do When Your Industry Is Dying

Nicholas presses Hillen on a key founder fear: “What if the thing I used to make money on… stops making money?”

Dr. Hillen has a two-part answer:

It’s normal. Every great company faces this at some point.
Redefine your problem as a set of strategic opportunities.

Case in point: Netflix. They went from mailing DVDs, to streaming, to producing original content. Their value proposition stayed the same, but their business model evolved. Strategy helped them reposition before the industry collapsed around them.

🧬 What Makes a Founder Strategic?

It’s not IQ. It’s not an MBA. It’s not being the loudest in the room.

It’s the ability to:

Zoom out from the day-to-day
Spot patterns across time and context
Connect capabilities to long-term opportunities
Make deliberate trade-offs

He also notes the tie between strategy and capital: no investor buys into a budget. They buy a compelling strategic narrative.

“Your job as a founder is not just to manage the business you are – it’s to create the business you’re not.”

📚 What’s On His Bedside Table?

In true strategist form, Hillen reads broadly and uncomfortably. Fiction, biography, trend analysis, and a few health books outside his zone – all to keep his thinking flexible.

“Chekhov,” he says, “already wrote about every people problem you’ll face in a company.”

🔗 Where to Find the Book

Grab The Strategy Dialogues on Amazon or head to johnhillen.com to learn more. Whether you're building the next unicorn or leading a team of two, this book’s a masterclass in practical strategy – minus the fluff.