It's a Sprint, Not a Marathon! Strategy in the age of AI

AI has changed how Startup CEOs must think about strategy, and it's all about speed. Here's a practical guide...

My Least-Favorite Race? The 5K!

I love the half-marathon!

In the half, I can settle in and run in the “orange zone” (~80%) for a couple of hours. I can enjoy the scenery and, if I’m smart with my pace management, push for the last five miles to reel in competitors who went out too hard.

“See Ya!” - I passed that guy at mile 12!

But a 5K? I hate 5Ks!

Yeah, it’s only 3.1 miles, but it’s all in the red zone (~90% effort), and that extra 10% is all mental game and strategy.

For me, a 5K takes:

1. Max speed. I have to go out hard and risk blowing up. The “start steady, then reel people in” strategy has no place in 5Ks.

2. Max concentration. If I allow my mind to wander for 30 seconds, my pace drops, and that mile is screwed.

3. Constant attack! I must take any opportunity to catch the competition off guard, and I must be prepared to attack several times before it sticks. Running all out on a downhill is my favorite tactic because that’s when most people catch a breather.

I argue that, in the age of AI, strategy is a 5K!

Or rather, a succession of 5Ks where only the podium placers (top three) from the current race move on to the next 5K.

This is a far cry from just a year or two ago…

2022 Taught Startup CEOs To Run At A Marathon Pace

2021-2023 was the post-ZIRP “funding winter,” where SaaS companies couldn’t raise new rounds and were forced into survival mode.

Strategy shifted out of necessity because:

• VC investments plummeted 50% as investors shifted from FOMO to skepticism.

• Valuations fared even worse, with 50-80% declines on 2021’s high-water marks.

• Runway became the most important metric; you needed 36 months to have a chance of surviving the funding winter.

• This triggered mass layoffs and the era of efficiency.

• The metrics that matter became Burn Multiple, CAC:LTV, NRR, and a metric many startup CEOs had to look up, cash-flow breakeven!

• The Board’s first question became,“Are we default alive or default dead?”

Startup CEOs learned to run at a marathon pace, carefully managing resources to make it to the finish. It was more about outlasting the competition and acting responsibly.

Now, AI has forced startup CEOs to tear up the post-ZIRP playbook. The rules of strategy have changed, whether you are a pre-seed AI-native disruptor or a growth-stage startup trying to defend your turf.

How Does AI Change The Startup Strategy Game?

What’s different about this era of LLM-fueled innovation? Market and company building dynamics have changed:

1. Insanely fast development and deployment cycles. You can stand up a product in hours and ship updates daily.

2. Highly motivated prospects. Every customer CEO is asking their CTO, “What is our AI strategy?” Those CIOs who ignored your calls two years ago are now calling you.

3. Huge influx of capital. FOMO is back as investors back barely-formed ideas and ML luminaries with unsustainable valuations.

4. Ubiquitous disruption. No product category or business model is safe as AI agents reduce marginal operating costs to near-zero.

5. Incumbent disintermediation. Big tech incumbents are no longer secure. I now use ChatGPT to decide what to buy instead of Google.

6. Level playing field. Technical skills are less critical in the age of Cursor. Size and resources are less of an advantage and can work against you.

7. Insane pay packages! While some labor costs are tending towards zero (think BDRs and CSRs), others are topping $100M (think ML Engineers or AI Researchers).

This means that the rules of strategy and competition have changed radically.

Time To Rewrite Those Strategy Textbooks!

The strategy frameworks we’ve been taught are being rewritten! Here’s my take on how AI changes some of the top frameworks:

The Implication: “Speed Is The Only Moat”

Chances are, you’re in a land grab, or defending against one.

That’s why I think Jamin Ball is right: Speed is now the only sustainable moat! Yes, proprietary data and user context are important, but both are ultimately copiable.

“Speed isn’t just important, it is the moat. The ability to build, ship, learn, and adapt faster than everyone else is the only sustainable edge right now. In a world where everything is open source, everything is demo-able, and everything is one blog post away from being copied, speed is the only thing that compounds.

Execution speed. Hiring speed. Firing speed. Distribution speed. Even decision-making speed. You don’t win because you’re defensible, you win because you’re faster. Killing bad ideas is just as important as the speed of executing against good ones. The opportunity cost of time has never been greater. So if you’re trying to build a moat today, maybe don’t think of it as a castle wall. Think of it as a race. Whoever stacks the most advantages the fastest: products, distribution, talent, infra, wins.”

Jamin Ball, Clouded Judgment Substack, May 30th 2025

To survive in the age of AI, startups must become 5K specialists, not marathoners. That means running way faster while being more aggressive and strategic.

So, what is a startup CEO to do?

A Startup CEO’s Guide: Strategy In The Age Of AI

[Note: This advice holds whether you are building an AI-native product, or you are defending your SaaS product against an AI incursion.]

1. CEO Think Time is even more critical. 
Your team are too busy executing, only you have the time and perspective to think about where we’re going. Dedicate at least an hour a week to reading, consulting others, and thinking about strategy.

2. Treat strategy as a hypothesis. 
Strategy is a hypothesis of how your startup will win. But a hypothesis needs constant testing and updating based on the evidence. Expect to change your hypothesis, and your mind, frequently. 

3. Increase your company strategy cadence. 
Annual/quarterly offsites are no longer sufficient. Review and update your strategy hypothesis with your Leadership Team at least monthly.

4. Decide your race distance. 
Take a guess at when the race will be decided in your category, then how much runway you can gamble. What’s the use of thirty six months of runway if the initial race will be decided in six? For example: Cursor grew from $1M-$100M ARR in twelve months! Good luck if you want to be the third best AI coding tool.

5. Start with an uncomfortably narrow ICP and just one use case. 
This allows you to build proprietary data quickly and solve reliability problems. For example: EvenUp started by helping Personal Injury lawyers write Demand Letters. They built trust and credibility before expanding to become a full-service legal platform.

6. Then, expand basd on engagement. 
In a land grab, you can’t wait for PMF to scale. Engagement is your best early signal. Track DAUs/WAUs more than net 30-day retention. Once you see strong signs of engagement, expand your use cases to gobble up more of your ICP’s “jobs to be done.”

7. Focus on Deployment Frequency, not big releases. 
Ship early, ship often. Don’t overwhelm uses with lots of changes; make them feel like they get a little more value each week. For example: For example: ChatGPT and Claude roll out small updates weekly.

8. Switching costs are your friends. 
The best moat in the short term is to make it unattractive to move off your platform. Two elements: proprietary user/company data and personalization/context. For example: Once your personal inujry firm has given EvenUp all your case files and learned your workflow and style, then it’s a significant effort to migrate to a competitor.

9. Monteize later. 
The usage network effects are so strong that you must make initial use frictionless. That’s why you need free or freemium tiers to get lots of initial use an drive the network usage flywheel. Start with a low or free product For instance, ChatGPT started out free before adding a $20 tier, then $200, and now a $10M tier!

10. If you’re serving enterprise customers, consider forward-deployed engineers to help build your product. 
Palantir perfected this model where you send engineers onsite to work with big customers. They act as consultants and engineers to help build the product and tailor it to that customer while your startup retains the IP for the platform.

11. Don’t be afraid to “Flinstone” it. 
Andrew Chen (The Cold Start Problem) defines "Flintstoning" as using humans to simulate automation at first (like the Flintsones powering their car by running.) EvenUp initially used significant human intervention to make up for early AI unreliability. They gambled that the models would catch up.

12. Expect to be ripped off by the competition
Especially if you’re in consume! By all means, send them a cease and desist, but your best strategy is to ignore them, get closer to your ICP and move faster.

The CEO As Pacesetter

In a 5K I have to constantly push myself back up to 90%. My inner monologue cycles between stride cadence, checking my watch metrics, pushing into the hurt-locker, and chasing down the runner in front of me. It takes all my focus to be my own pacesetter.

But at some races I slip behind somone running the perfect speed. Instantly, the same pace feels easier. It’s as if they take on the mental load for me. I can relax and follow (plotting my attack!)

The CEO needs to be their startup’s pacesetter. You must overcome inertia in your startup since, left alone, your leaders will become distracted and your employees will relax a little.

You must decide what’s most important, focus your team on the few things that matter, and push everyone to ship faster.

The CEO must push the velocity of a startup, and never has that been more important!

“No, no, lightspeed is too slow. We’re going to have to go right to…ludicrous speed!”

Dark Helmet, Spaceballs, 1987

Coaching Inquiry

• How much runway do you have? When will the “podium” be decided in your category? What race are you in - 5K? 10K Half marathon?

• How will you increase your startup’s velocity? Where is the inertia?

• How much time do you spend thinking about strategy per week? How effective is this time?

“Speed is the essence of war.”

Sun Tzu, The Art of War, ~5th century BC

Let me know what you think. And let’s talk if you want to clarify your strategy and move faster. Or if you’re up for a run!

Thanks for reading,

Tim

www.timporthouse.com

P.S. Many of my obsessions come from conversations with you, my clients. I don’t call you out to preserve anonymity. Please know you are my inspiration and teacher, and I am so grateful.

Glossary:

CAC = Customer Acquisition Cost

DAU = Daily Active Users

ICP = Ideal Customer Profile

IP = Intellectual Property

LTV = Lifetime Value

ML = Machine Learning

MVP = Minimal Viable Product

PLG = Product-Led Growth

PMF = Product/Market Fit

WAU = Weekly Active Users

ZIRP = Zero Interest Rate Program