GTM Made Simple

I stopped a CEO roundtable to share this data point: Gartner lost 70% of its value in two years, roughly $30 billion gone. It's tempting to laugh at that. Don't. The same force that gutted Gartner is coming for anyone whose value comes from packaging yesterday's insight, and that's a much bigger group than you think.

The uncomfortable question underneath the headline: if AI can do what you do in seconds, often for free, what's your actual moat? Product, features, and pedigree aren't it anymore. What survives is brand, community, and doing something genuinely different for a specific niche. This is about betting on the future you create, not the past you're defending.

⏱ TIMESTAMPS
(00:00) The stat that should make you question your business
(00:13) $30 billion in value wiped out
(00:23) Why this means knowledge work is over
(00:38) What I spent to get into the magic quadrant
(01:07) Is the game you've played for 20 years over?
(01:22) AI does what Gartner did, in seconds, for free
(01:49) If you package yesterday's insight, you're toast
(02:06) Your product is no longer your moat
(02:43) The three moats that still work: brand, community, niche
(03:01) You can't bet on the past. Bet on the future.

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Someone in a recent CEO roundtable asked me what made me the entrepreneur I am today, after building multiple hundred million dollar businesses. The honest answer isn't a strategy. It's a conversation I had with my wife.

I was 35, we'd just had our second kid, my wife wasn't working, and I wanted to leave a stable path to become a co-founder at a company that could pay me close to nothing. In this video I share what she said that changed everything: she gave me one year to prove it had legs, or I'd go get a real job. That was the gift, the gift of time, and the gift of a forcing function. There's no perfect time to bet on yourself. But if there's a problem you can't sleep until you solve, find a partner and a forcing function, and get moving.

⏱ TIMESTAMPS
(00:00) The question I got in a CEO roundtable
(00:53) From a $10M company to a $10B company
(01:16) Meeting the Terminus co-founders in 2015
(01:39) Pitching account-based advertising on a whiteboard
(02:19) "Why don't you become a co-founder?"
(02:43) Going home to tell my wife
(03:37) "Do you want to be an entrepreneur at 35 with two kids?"
(04:46) Why I couldn't say no to this problem
(05:23) The three things she did that became the inflection point
(06:00) The gift of time and the gift of a forcing function
(06:59) That day, I became an entrepreneur
(07:13) There's never a good time. The best time is now.
Give yourself the time you need. But create a forcing function that isn't forever.

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Every B2B founder is one product update away from becoming a feature of ChatGPT or Claude. The biggest threat to your retention isn't your competitor anymore. It's a $20 a month tool that does 80% of what your product does, with none of the friction. In this video I break down what a CEO said in one of my roundtables that stopped the whole room: customers are quietly canceling, not because they found something better, but because they found something good enough.

We've all built retention playbooks against competitors, battle cards, onboarding flows, customer success teams. But AI doesn't play by those rules. So the real question for every CEO right now is simple: is your product 10x better than the AI version of your product? If the honest answer is "we're working on it," that's the number one thing to fix before you touch anything else in your go-to-market.

⏱ TIMESTAMPS
(00:00) One feature away from becoming a feature of ChatGPT
(00:33) What a CEO said that silenced the whole room
(00:44) Quietly canceling: "good enough" beats "better"
(01:05) Your real competition is a $20 tool
(01:19) Why your old retention playbooks don't work on AI
(01:52) The renewal conversation you're not seeing
(02:09) The question: is your product 10x better than AI?
(02:43) The one thing to fix before your GTM strategy
(02:43) Why GTM OS is the answer, not another feature

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Most CEOs can't answer one question that decides everything: which products create the highest customer value? Not revenue, not cash flow, not hiring. This one. In this video I break down exactly how to answer it, using what I learned going from a $10 million company to a $10 billion one.

I ran marketing at Pardot when we got acquired by ExactTarget, then by Salesforce for over $2.7 billion. I watched Salesforce take the exact product we sold for a thousand dollars a month and sell it for fifty to a hundred thousand a year, because they understood customer value in a way most companies never figure out. Then I took that same lesson to Terminus, launched the ABM category, and grew from one million to five to fifteen. Here's how the highest-customer-value question drives all of it.

⏱ TIMESTAMPS
(00:00) The question most CEOs can't answer
(00:32) From a $10M company to a $10B one
(01:00) How Salesforce manages 100+ products
(01:33) The "clouds" system and highest-margin products
(02:09) Why Pardot landed in the Sales Cloud
(02:35) The $1K product sold for $100K
(02:58) Taking the lesson to Terminus
(03:34) Launching the ABM category in 2015
(04:25) How to find your own highest customer value
(04:47) What this question tells you to do, and not do

Find all 8 GTM OS questions here: https://www.youtube.com/playlist?list=PLAFIwLvOQGkQ

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Most go-to-market plans fail, and it's not a marketing or sales problem. It's that CEOs treat go-to-market as an annual event instead of an ongoing process. In this video I walk through the exact process we take 3,000 companies through to run on GTM OS, live, step by step.

I break down the five valleys of death, how to find which stage you're actually in (problem, product, or platform market fit), the 15 go-to-market problems every company pulls from, the alignment assessment that surfaces where your team disagrees, and how to map your whole go-to-market onto one slide so you know what to focus on for the next 90 days.

⏱ TIMESTAMPS
(00:00) How to run on GTM OS: what you'll learn
(00:37) Why 70% of GTM leaders lack clarity, not certainty
(01:02) Why most go-to-market plans fail
(02:56) The mistake: treating GTM as an annual event
(03:36) Go-to-market is an ongoing process, not a plan
(04:43) The full system: 5 valleys, 3 P's, 15 problems
(05:29) Step 1: the five valleys of death
(07:58) Step 2: problem vs product vs platform market fit
(08:11) The $20M vs $5M valuation story
(10:36) Step 3: the 15 go-to-market problems
(12:25) Step 4: the team alignment assessment
(13:33) Step 5: the 8 questions of GTM OS on one slide
(14:03) Turning it into 90-day projects
(14:48) Why the best companies do this quarterly

📌 Get the full framework and walk through it with your team at runongtmos.com

Figma, Circle, eToro, and a wave of other 2026 IPOs are all down double digits from their peaks, averaging around 44%. They had the growth. They had the hype. What they didn't have was profitable revenue, and the market punished them for it. In this video I break down the most important go to market lesson of 2026 and the mistake most companies are about to make.

I walk through the difference between IPO growth and compounding growth, why net revenue retention and CAC payback decide whether your business survives, and the three numbers every leader on your team should know cold. This comes from what we've seen across 3,000 companies and from going through this exact cycle myself, from a $10 million company to a $10 billion one at Salesforce.

⏱ TIMESTAMPS
(00:00) Every 2026 IPO is down double digits
(00:53) The CEO roundtable conversation behind this
(01:20) Growth without profit gets punished
(01:52) Why the layoffs blamed on AI are really bad unit economics
(02:38) The eight-question GTM operating system
(04:06) EOS runs the company, GTM OS runs the revenue engine
(04:33) Two types of growth: IPO growth vs compounding growth
(05:53) Why NRR below 100% means you're in trouble
(06:24) The three questions every leader should answer
(06:55) Why net revenue retention is your best predictor
(08:19) Fix your CAC payback time
(09:02) Why expansion revenue beats new acquisition
(10:14) The blunt advice: stop celebrating revenue growth
(11:00) Profit is the way out of the valley of death

📌 Go through the assessment 3,000+ CEOs have used at runongtmos.com/move to see if your growth engine actually compounds.

My son's tennis old coach stopped everyone mid-drill and asked one question that applies to every founder, CEO, and leader I know, "Are you here to win?" 

In this video I break down what happened next, how the entire group raised their level in 15 minutes, and why it changed how I think about every sales call, campaign, and experiment we run.

The lesson isn't about tennis. It's about the standard you hold yourself to when the stakes feel low, because that's the standard you'll actually have when it's game time.

⏱ TIMESTAMPS
(00:00) A lesson from my son's tennis practice
(00:44) The question the coach asked: are you here to win?
(01:24) "Play to win. It doesn't matter where or who with."
(01:51) How the whole group raised their level in 15 minutes
(02:17) Why entrepreneurship is about raising your standard
(02:25) Am I playing to win, or just going through the motions?
(03:02) Doing everything with more intentionality
(03:32) There's no excuse for playing lame

📌 Take the GTM assessment at runongtmos.com/move to find out which stage you're actually in.

Every AI company right now is stuck in problem market fit, and most CEOs have no idea. They think revenue means product market fit. It doesn't. In this video I break down the difference between the three stages every company moves through: problem market fit, product market fit, and platform market fit, using what we've learned assessing over 2,000 companies since the MOVE book.

I'll walk through the moment I told a friend his $25 million business was worth less than a competitor doing $5 million, why there's zero loyalty in AI right now, and what it actually takes to build the kind of moat that makes you a platform instead of a point solution.

⏱ TIMESTAMPS
(00:00) Every AI company is in problem market fit
(00:16) What we learned assessing 2,000 companies
(00:53) What problem market fit actually means
(01:38) How a $25M company can still be problem market fit
(01:43) The $25M vs $5M valuation story
(03:19) Product market fit: is it replicable?
(03:57) Why there's no loyalty in AI right now
(04:31) Platform market fit: the gold mine
(05:39) Why most CEOs miss where they actually are
(06:11) Early meetings vs revenue vs the moat
(07:41) Why companies get stuck at $3M to $20M

📌 Take the GTM assessment at runongtmos.com/move to find out which stage you're actually in.

There are 8 questions every company needs clarity on to build a real go-to-market operating system, and most businesses never sit down to answer the first one. In this video I walk through how one question took our business from $0 to $1 million in revenue in 9 months, with no marketing team and no sales team.

I break down the exact process: how we turned advisory work into three revenue streams, how three people each built half a million dollar businesses using the same process, and why "where can you grow" is the wrong question compared to "where can you grow the most."

⏱ TIMESTAMPS
(00:00) The result: $0 to $1M in 9 months, no sales team
(00:16) The 8 questions in the GTM operating system
(00:27) Question 1: where can you grow the most
(01:20) Turning advisory work into 3 revenue streams
(01:59) Workshops, pillar work, and projects explained
(02:38) The process that turned 3 people into $500K each
(03:04) Scaling into a fractional marketplace
(03:57) Why "grow the most" beats just "grow"
(04:34) The exercise: write down where you can grow the most
(05:07) Five years later: $10M and still the same question

Find all 8 GTM OS questions here: https://www.youtube.com/playlist?list=PLAFIwLvOQGkQ

📌 Take the GTM assessment at runongtmos.com/move to answer this for your own business.

If you can't say what you do in one sentence, that's why your fractional pipeline is dry. Most fractional CMOs and CEOs describe themselves like an HR job title, and the market doesn't pay for job titles. It pays for outcomes for a specific kind of company.

In this video I break down the three positioning angles that separate fractionals who are fully booked from ones still chasing DMs: industry, stage of business, and who you actually serve. 

⏱ TIMESTAMPS
(00:00) Why nobody's hiring you right now
(01:00) Why I never called my own business "fractional"
(02:00) Positioning angle 1: industry, the Lydia story
(04:00) Positioning angle 2: stage of business, the Matt Anthony story
(05:00) Positioning angle 3: who you serve, the Alan story
(06:00) Why niching down gets clients coming to you first

📌 See how our 100+ certified partners built their fractional businesses at runongtmos.com