I watched our user count climb. To this day I remember the moment 656 Peruvian signed up because we were featured on the front of one of their top blogs.

I watched our social engagement climb. As it should, we had done a good job gamifying user interaction.

I told myself the story every first-time founder tells himself: growth is growth, and growth wins.

What I wasn’t watching was how much of my own capital it cost to get there.

By the time I looked closely, I’d been quietly funding two of the most expensive vanity metrics in startup land — and I didn’t have the numbers to prove our go-to-market strategies were working for anything other than user growth. I just had a bad feeling and a thinning bank account.

That feeling has a name now. It’s called not knowing your growth levers.

There are three you should be tracking, at a minimum: Customer Acquisition Cost (CAC), Lifetime Value (LTV), and Payback Period. Founders talk about them like they’re optional context. They’re not. They’re the difference between a fundable business and a busy one.

CAC is what it costs you to win a customer. LTV is what that customer is worth to you over time. Payback Period is how long it takes to earn back what you spent acquiring them — CAC divided by monthly revenue per customer.

Here’s the part most founders skip, that I didn’t just skip, I completely ignored: these three numbers don’t operate independently. They’re one system. Move one, and the other two move with it.

LTV/CAC tells you whether your growth engine works. It matters most while you’re still proving the model can scale. A 3:1 ratio is the line investors that I work with actually believe — and companies that clear it grow roughly 20% faster than the ones that don’t.

Payback Period tells you whether your growth engine survives. It matters most when your runway gets short and your market gets crowded — which, eventually, it will. Startups with a payback period under 12 months are roughly 2.5x more likely to make it to Series B (Source). The best operators I’ve seen do it in <6 months.

The relationship is simple. A high CAC drags out your payback period. A strong LTV/CAC ratio shortens it. When your GTM is actually dialed in, you’ll feel both move at once — the gap between LTV and CAC widens, and the time it takes to earn your money back shrinks.

Investors notice that combination immediately. Growth for growth’s sake stopped impressing investors years ago. What gets a term sheet now is proof that your growth engine is efficient and sustainable, not just busy.

So how do you actually track this?

Your LTV lives in your billing system. Your CAC lives in your ad platforms and your accounting software. The hard part isn’t pulling either number — it’s attribution: connecting a closed deal back to the GTM motion that actually won it.

You can do this manually on a spreadsheet, and if cash is tight, you probably should. Once it’s worth automating, tools like ChartMogul, Baremetrics, ProfitWell, Cometly, and Pecan AI can help stitch the picture together. I haven’t used all of them personally, so do your own diligence — but the category exists for a reason.

Here’s my advice, the kind I wish someone had handed me before my first raise: pick a day this month, pull your real CAC, your real LTV, and your real payback period, and write them down. Not the version that sounds good in a pitch deck. The real one.

If you don’t like what you see, you’re not alone. Most founders don’t, the first time they look.

But you can’t fix a leak you haven’t found. And you can’t raise a round on vibes forever.

What would your next pitch meeting look like if you walked in already knowing these three numbers cold?

Every year I take a multi-month sabbatical. I actually do this twice a year, in the winter and in the summer. The summer break typically coincides near my birthday, starting on May 15th and ending on July 15th. Although, sometimes I extend it into August if that feels right.

It’s not a complete reprieve from any and all responsibility. For example, I do work during this period. Although I take a lot of PTO during that period-I earn upwards of five weeks off per year.  In fact, during June I’ll only work four out twenty-two work days.

Beyond work, I power down from all the other normal hustle and grind of my daily life. That includes virtually no side projects, unless they are something that is a) extremely interesting to me; b) ridiculously lucrative. For the past three years no project has met those conditions enough to entice me away from my side-hustle sabbatical. This time also includes writing less, although when “inspired” I do write some, since writing is one of my favorite things to do to relax.

If you’ve never taken a break like this, I can’t recommend it enough. The benefits aren’t endless, but there are many.

Room for deep work

I spend my sabbatical asking myself deep questions about the future. Like:

• Is the work I’m doing fulfilling?

• I’m I working with people I can learn from?

• Am I focused on the right skills to be acquiring?

• Which projects were the most exciting to work on? What are the common themes of those projects?

More times than not, it’s been the deep work I do during a sabbatical that led to a professional change in course.

For example, it was a winter sabbatical ten plus years ago that led me to the decision to leave the bank where I was Chief Lending Officer and, according to the CEO and a few Board members, the likely next CEO. It was this past winter sabbatical where I realized that I was ready to move on from leading my company’s largest product build in its 50+ year history. One that I helped incubate.

Asking hard questions, doing the deep work, during these sabbaticals has fundamentally changed my life for the better.

Room for re-invention

I use my sabbaticals to re-invent my life. During this down time, away from many of the normal things that take up my energy, I audit what is working and what isn’t. If something is an energy drain, and not fundamentally necessary to our livelihood, I cut it out of my life. That may include business activities, events I was attending, or even people I was spending my time with. Creating distance from those things over an extended period gives me the space I need to evaluate if they are serving me or if I was serving them.

Room for family

Ten years ago I made the decision to leave a role where I was being told that I was the next CEO. I was ready for a new challenge and the decision to transition out of that role was partially because I wanted to work from home, where I could be around my wife and daughter more. That decision has been one of the best decisions I’ve made, because I’ve been afforded all kinds of “stolen moments” over the past decade.

I would estimate that my family time goes up by 25%-40% when I’m on sabbatical. This summer will be different than past summers, since our daughter is driving now. Still, this time gives me more chances to bond with my family and make relationship deposits for upcoming times when I may not have as much bandwidth.

Room for my hobbies

I’m fortunate to have time to explore my main hobbies through a normal week. They include video games, which I’ve played for 47 years now, reading, and writing. During my two sabbaticals, I ramp up my time on those things.

The biggest change is that I shift my writing, or most of it, from a professional focus (GTM/Fundraising/etc.) to life design and working on other projects I have been wanting to get to. Right now, the biggest change is that I’ve refocused some of my writing energy into my second fantasy novel. It’s one I’ve been mentally working through for a few years and I think I finally have enough content carved out to keep the ball rolling.

Tips for taking your own sabbatical

If you are considering a similar approach, here’s some tips for you to consider.

• Some people take full-on sabbaticals, from virtually everything. They often take long trips as part of their time away. If that’s not something you can afford, in time and money, there’s no reason you can’t take an at home sabbatical. Many, in fact, most of mine was been at home.

• Sabbaticals don’t have to be for months to be successful. Mine have ranged from one week to one month. The key is giving yourself enough space to do the deep work.

• They don’t have to be an all-or-nothing break from life. In fact, I would tell you that it’s unreasonable to expect that. Social media has contributed to the romanticization of sabbaticals as a modern day pilgrimage to find one’s self. While that is the goal, you don’t need to disappear or put your entire life on hold to accomplish it.

What you can’t expect is to take one sabbatical and it be completely transformational. That’s because it takes time to get used to the break in activity. I’m typically a week or more into my breaks before I am mentally free from all of the other distractions I’ve put aside. In fact, there have been times when I had started a break and then broke it because the inactivity was too hard mentally. That’s why, if you decide to give it a go, don’t be disappointed if your first few attempts feel more like a typical vacation than a true sabbatical.

I’m one month into this summer sabbatical, and I can already tell it’s going to be one of my more impactful/productive breaks. From the start I felt free of a lot of things and I wasn’t feeling the pull towards activity that was there in when I started taking these breaks. I can’t wait to report back on the deep work I did and the decisions I make.

See you in July/August!

His logistics and transportation consulting business had been scaling rapidly ($75M in assets managed) and the thought was that I’d eventually join the company (I never did. More on that another time).

We had just walked the VP through a thorough ROI model. Clean slides. Tight numbers. The kind of deck that wins deals.

She nodded. She said she was impressed. And then she said the four words that kill more B2B deals than any competitor ever will:

“Let me think about it.”

I’ve been in enough rooms to know what “thinking about it” means. It doesn’t mean the prospect needs more time. It means you haven’t made the cost of waiting feel real.

We had shown her what she’d gain. We never showed her what she was losing every single day she didn’t act.

That’s the gap. And it’s one most B2B sales teams never close.

ROI Isn’t Enough Anymore

Return on Investment is table stakes. Every vendor in your category has an ROI model. Your prospect has seen seventeen of them this quarter. They all show positive returns. They all have optimistic assumptions. And they all get filed in the same folder labeled “maybe someday.”

ROI answers the question: “Is this worth it?”

But that’s not the question that drives urgency—one of the best GTM enablers. The question that drives urgency is: “What happens to me if I wait?”

That’s where the Cost of Doing Nothing — CODN — comes in.

CODN isn’t a new concept. But it’s almost universally underdeveloped in B2B sales motions. Most teams treat it as a throwaway line in the objection-handling section of their sales playbook. It deserves its own framework.

What CODN Actually Measures

The Cost of Doing Nothing quantifies the compounding penalty your prospect pays for every week, month, or quarter they delay a decision.

It’s not about fear-mongering. It’s about making the invisible visible.

There are four buckets where CODN lives:

1. Hard Dollar Losses These are the easiest to calculate and the most persuasive. What is the prospect actively losing in revenue, efficiency, or waste right now because they don’t have your solution? If your platform reduces manual processing time by 12 hours per week per employee, and they have 40 people doing that work, that’s 480 hours a week. At a fully-loaded cost of $50/hour, that’s $24,000 a week walking out the door. Every week they wait is a $24,000 decision.

2. Compounding Competitive Exposure Markets don’t stand still while your prospect deliberates. If their competitors are moving and they’re not, the gap compounds. This is especially sharp in categories where first-mover advantage matters — market share, talent acquisition, customer data accumulation. CODN here isn’t just a cost; it’s a widening gap that becomes harder to close with each passing quarter.

3. The Internal Cost of the Workaround Every prospect who isn’t using your solution is using something — usually a patchwork of spreadsheets, manual processes, or a legacy system that’s slowly eating their team alive. The workaround has a real cost: engineering hours, employee frustration, error rates, and the management overhead of holding it all together. I’ve seen companies spending $$$$ a year maintaining a homegrown system that a $$ solution would have replaced. Nobody had ever added it up before we did it for them.

4. Strategic Drift This is the hardest to quantify but often the most emotionally resonant with senior buyers. Every month they don’t solve this problem, their best people are working around it instead of on something that matters. Talent is expensive. Attention is finite. Strategic drift — the opportunity cost of smart people doing dumb work — is real, even if it doesn’t show up on a P&L.

How to Build a CODN Model

Here’s the framework I use. It’s not complicated, but it has to be built with the prospect’s own data, not yours.

Step 1: Identify the bleeding. Before you build anything, ask your champion one question in discovery: “What does this problem cost you today?” Let them answer. Don’t fill the silence. The number they give you becomes the anchor for everything that follows. If they don’t know, that’s your first insight — and your first opportunity.

Step 2: Attach a weekly run rate. Take whatever you identify in Step 1 and convert it to a weekly cost. Weekly is psychologically more powerful than annual. “$1.2M per year” feels abstract. “$23,000 per week” lands differently. People can feel a week. A year is a rounding error.

Step 3: Map the compounding. Show what happens at 30, 60, and 90 days of inaction. Not 12 months — that’s too far away. Three months is the next budget cycle, the next board meeting, the next performance review. That’s where the urgency lives.

Step 4: Connect it to something the buyer cares about personally. This is the part most salespeople skip. A VP of Operations doesn’t just care about the company’s P&L. She cares about her team’s morale, her own credibility, and whether she’s the person who fixed a problem that’s been dragging for two years. Connect the CODN to her story, not just her company’s spreadsheet.

The Conversation That Changed How I Sell

Back to that VP of Operations.

We went back to her two weeks later. Same solution. Different conversation.

We didn’t open with our product. We opened with a one-page document my father called a “Status Quo Assessment.” It showed her, in her own numbers, what the current state was costing her operation every month. We pulled the data from the discovery call. We did the math she hadn’t done. We showed her that in the eight weeks since our first meeting, her company had absorbed roughly $190,000 in inefficiency that our platform would have eliminated.

She signed on the spot.

The product didn’t change. The ROI model didn’t change. What changed was that we made the cost of waiting concrete and personal.

The Takeaway

If your deals are stalling at “let me think about it,” you probably have a CODN problem, not a product problem.

Build a Status Quo Assessment for your top three open opportunities this week. Use their numbers. Map the weekly run rate. Show what three more months of inaction costs them — in dollars, in competitive exposure, and in their team’s time.

The question your prospect needs to answer isn’t “Is this worth buying?”

It’s “Can I actually afford to wait?”

I’ve tried to be an early-morning person (waking up before 630am) lots of times in my life.

But, it’s never stuck, permanently.

Every now and then I’ll naturally wake up early, but that’s normally due to poor sleep.

The mornings where I do wake up early, especially if a busy schedule demands it, I knock out my workout for the day. The problem is that I spend most of my workout feeling in a haze of sleepiness. Once I’m through with my workout I usually feel accomplished. But then the 2pm sluggishness kicks in.

I’m just not an early-morning person and I’ve come to embrace that fact.

My Happy Place—Slow Mornings

My natural, unforced wake up time is between 7am-8am (usually closer to 7am).

It still takes me a bit to get going, which is why I always try to give myself some space to wake up.

That’s why I designed my mornings to be slow.

It has become one of my happy places. Here’s what it looks like:

• Bible study

• Journal (not currently, I’m on a break; by the way paper or digital for those of you that journal?)

• Breakfast (almost always Overnight Oats and a Vanilla Cream coffee)

• Soft, lyric-free music (usually the Spa channel on Apple Music; I have my Alexa preset to play it when I say “Alexa let’s relax”)

• Some form of ambient video playing on YouTube (this is typically only in the colder months, but today I decided to play one; see image below)

• Writing (some form of it; either business or personal)

When my schedule allows, that “flow” will take about two hours. After which I knock out a workout (5-6 days per week).

Why Slow Mornings Work (for Me)

Slow mornings feel like gifts to my future self. Giving myself the space to start slowly, rather than being jolted into the day, makes my mind feel more at peace, protects my mood, and makes me feel more productive than waking up running at full tilt.

Here’s what I’ve noticed the benefits are:

It protects my mental health. Starting the day with Bible study and journaling means I’ve already done something for my soul before the world gets a chance to demand anything from me. The day hasn’t hijacked me yet. That matters more than I used to realize.

It reduces decision fatigue early. My morning routine is predictable on purpose. Same music, same breakfast, same rhythm. I’m not making a dozen small decisions before 9am. By the time I sit down to write or work, my brain has some gas left in the tank.

It makes the workout better. Here’s the thing I noticed when I stopped forcing the early workouts — I actually perform better when I exercise after my slow morning instead of before it. No haze. No dragging. I’m awake, fed, mentally settled, and ready to push.

It sets the emotional tone for the whole day. On the days my routine gets interrupted — an early meeting, a disrupted schedule — I can feel the difference. I’m a little more reactive, a little more scattered. The slow morning is doing more work than it looks like it’s doing.

Where’s Your Hustle, Bro!?

I used to think that slow mornings were just an excuse to avoid doing hard work. But, that’s simply not the case.

I see slow mornings as using intentionality as a weapon. Intentional starts are the opposite of laziness. They are a deliberately designed system that allows my body and mind to warm up, not an excuse to avoid the day.

Are there days where my slow mornings have me too relaxed and when I’m unmotivated to get to my workout? Sure. But that’s just a matter of discipline, not how I structure my day.

All the hustle/productivity bros online would have you believe a slow morning is a mistake. It’s not. In fact, its biological for some people.

A Quick Note on Chronotypes

You’ve probably heard of being a “morning person” or a “night owl.” That’s essentially what a chronotype is — it’s your body’s natural, built-in preference for when to sleep, wake, and be most alert. It’s not a personality quirk or a discipline problem. It’s biology.

Your chronotype is largely determined by your circadian rhythm — the internal clock your body runs on. That clock influences not just when you feel sleepy or awake, but also when your body temperature peaks, when your hormones shift, and when your brain is sharpest. And here’s the part most people don’t realize: you don’t fully choose it. Genetics plays a significant role.

Researchers typically break chronotypes into a few broad categories:

• Lions — natural early risers; alert in the morning, wind down early (this is my wife)

• Bears — the most common; follow the sun roughly, peak mid-morning to early afternoon (me; sort of)

• Wolves — the true night owls; slow to start, hit their stride later in the day (100% our daughter)

• Dolphins — light, irregular sleepers who often feel like they don’t fit neatly anywhere

(These labels come from sleep researcher Dr. Michael Breus, author of The Power of When.)

Most people are Bears, which is why the typical 9-to-5 workday was more or less built around them. If you’re a Wolf — or even a late Bear like me — you’ve probably spent years feeling like something was wrong with you because you couldn’t make the early-morning hustle work.

Nothing is wrong with you. Your clock is just set differently.

The pressure to wake up at 5am and conquer the world before sunrise is real, and it’s loud. But productivity isn’t one-size-fits-all. Working with your chronotype instead of against it tends to produce better focus, better mood, and yes — better workouts. Which I need to head towards, now that I’m fully awake. 💪

They’re moving from click-optimization to identity-optimization. The algorithm no longer rewards the post that gets the most clicks — it rewards the account that consistently signals expertise in a specific domain over time.

If LinkedIn is part of your content strategy and you are chasing viral hits, you’re not just underperforming. You’re invisible to the new feed.

Here’s what that actually means for your GTM.

The Old Game vs. The New Game

The old LinkedIn GTM was simple: post something that grabs attention, hope it explodes, ride the wave of inbound. It worked, for a while, because the feed was optimized for engagement spikes.

The new LinkedIn GTM requires something harder: patience and consistency around a specific point of view. LinkedIn’s AI is now mapping who you are based on the full body of your content, not just your last post. It’s building an identity profile for every creator and matching that profile to reader interests at the feed level.

So, if you are still posting off brand things (political views, a great meal you had, etc.) count on becoming known for those views.

Also, side note, can we stop calling something a “hot take” when its common knowledge?

Chasing virality in that environment is like trying to win a marathon by sprinting the first quarter mile. You’ll burn out and the algorithm won’t remember you fondly.

What “Long-Sequence GTM” Actually Means

A Long-Sequence GTM on LinkedIn means treating the platform like a drip campaign, not a broadcast channel.

Instead of posting when you have something “good enough” to share, you build a 60–90 day content arc anchored to a single core thesis — your specific point of view on one problem your ICP faces. Every post either deepens that thesis, challenges an assumption inside it, or proves it with a real example.

The algorithm learns what you stand for. Readers start to associate your name with that specific problem space. And when they need help with that problem — or know someone who does — you’re the first name that surfaces.

That’s not virality. That’s positioning. And positioning compounds.

The Three-Layer Long-Sequence Framework

Layer 1 is your Anchor Post — a long-form piece (1,000–1,200 characters) that states your core thesis clearly and without hedging. This is your flag in the ground. Post it first and refer (i.e. link) back to it.

Layer 2 is your Proof Loop — a series of shorter posts (3–5 per month) that validate the thesis using real examples, data points, or counterintuitive takes. These don’t need to be long. They need to be specific.

Layer 3 is your Conversation Driver — posts explicitly designed to generate comments by ending with a question your ICP actually debates. Comments signal to LinkedIn’s identity model that your content is resonating with a specific professional community.

Run all three layers simultaneously over 60–90 days and you’re no longer just posting on LinkedIn. You’re building a distribution asset.

The One Thing Most GTM Teams Get Wrong

They assign LinkedIn to marketing. Not the founder. Not the product leader. Marketing.

Marketing will make it look good and sound safe. Safe doesn’t build identity. Safe doesn’t build trust.

The highest-performing LinkedIn GTM strategies I’ve seen are driven by a person with a genuine point of view and enough conviction to be wrong publicly.

For example, Wade Arnold of Moov regularly posts his views on the fintech space and they are, sometimes, contrarian.

For startups, that means following a founder-led growth strategy. After all, the founder is the brand in the beginning. For better or worse.

If you’re not willing to say something that half your audience disagrees with, your content will be algorithmically invisible and commercially useless.

The question I’d push you to answer: what is the one problem in your space where you have a clear, defensible, possibly unpopular point of view — and are you posting about it consistently enough that a stranger could identify your thesis after reading 10 of your posts?

If the answer is no, you’re not doing Long-Sequence GTM. You’re just posting.

P.S. If you aren’t using LinkedIn as a GTM distribution channel and your ICP is spending time there, you should be. For context—my reach on LI is 3x that of my reach on X.

He won the case.

And six months later, a competitor built around it anyway — not by violating the patent, but by solving the same problem a different way. The moat he’d been defending didn’t exist. It was a line on a legal document. The market didn’t care.

That conversation stuck with me. Because I’ve watched a version of it play out over and over — founders and product leaders investing enormous resources into protecting something that feels like an advantage but isn’t actually one in the market.

AI just made that problem ten times worse. And most teams haven’t caught up to what that means.

The Old Playbook Was Written Before the Tools Changed

For the better part of two decades, the startup moat playbook read something like this: build something novel, patent it, protect it, and use that protection as a barrier to entry. Lock in customers through switching costs. Build your fundraising narrative around defensibility.

In fact, the angel investor syndicate I used to perform due diligence for prioritized this type of protection.

That playbook made sense when the cost to build was high, timelines were long, and technical complexity was itself a filter.

None of those conditions apply the way they used to.

Today, with the right AI tooling and a focused team, you can compress meaningful product development into weeks. I’ve seen it. I’ve done it. Competitors can too.

The timeline compression isn’t the scary part. The scary part is that everyone has access to the same compressor.

AI doesn’t just accelerate your development. It accelerates everyone’s. Which means the thing that used to buy you time — complexity — doesn’t buy you nearly as much anymore.

What AI Actually Collapsed

Let me be specific about what’s changed, because vague hand-waving about “AI disruption” doesn’t help anyone. It’s been overplayed.

Three things got dramatically cheaper and faster:

Building the first version. Foundational technical work that used to take a senior engineering team six months can now get to a functional prototype in a fraction of the time. Your competitors know this. AI-enabled product managers can build their own product’s MVP in weeks if not days.

Replicating a surface-level feature set. If your moat is “we have a better UI” or “we built this integration first” or “we have a proprietary algorithm” — assume someone can reverse-engineer the output, if not the method, inside of a product cycle.

Entering adjacent markets. The cost for an established player to spin up a competing offering in your category dropped substantially. This isn’t theoretical. I’ve watched it happen in fintech, in B2B SaaS, in lending infrastructure.

What AI didn’t collapse: the value of what you’ve already learned, what your customers have already told you, and how your team actually moves.

That’s the asymmetry most people are missing.

The New Moat Is What You’ve Accumulated, Not What You’ve Protected

Here’s the frame I keep coming back to: a moat is valuable because it’s hard to replicate quickly. The question isn’t “what can we protect legally?” It’s “what would take a competitor years to catch up to?”

The answer is increasingly: proprietary data and deeply embedded workflows.

Not the data you can buy. Not the publicly available training sets. The data that is a byproduct of how your customers use your product — the behavioral signals, the feedback loops, the edge cases that only show up at scale. The stuff that a competitor starting from zero simply doesn’t have, no matter how much they spend.

And workflows — the internal and external processes that your product is embedded in so deeply that switching isn’t just expensive, it’s disruptive to the actual operating rhythm of the customer’s business.

These are hard to replicate. They take time to build. They compound. And they don’t show up on a patent filing.

What This Looks Like in Practice

When I was working through a product launch into a market with significant regulatory complexity — financial services, where the surface area for compliance is enormous — the product itself was important, but it wasn’t the defensible asset. What was defensible was the decision logic we’d built from thousands of real scenarios, and the workflow integrations that meant our software was embedded in daily decisions across hundreds of institutions.

A competitor could build a competing product. They couldn’t instantly inherit decades of exception handling. They couldn’t recreate the muscle memory of thousands of loan officers who had been working in our system long enough that switching would mean retraining from scratch.

That’s a moat. And no patent attorney helped us build it.

Here’s how I think about it now — three questions every product and GTM leader should be asking:

1. Are we systematically capturing the data our product generates?

Not storing it — capturing it. There’s a difference. Because most of what I’m seeing is executives wanting to make data-driven decisions…but they don’t have the data. Storing is passive. Capturing means someone on your team is responsible for understanding what the data tells you about customer behavior, and feeding that back into the product and the GTM motion.

2. Is our product embedded in a workflow, or sitting adjacent to one?

Adjacent tools get cut. Embedded tools create switching costs. If your customer can turn off your product without changing how their team operates, you’re adjacent. If turning you off means rebuilding a process, you’re embedded. That’s the goal.

3. What does our data allow us to do that a new entrant simply can’t?

This is your actual positioning question. Not “what features do we have?” but “what can we learn, predict, or personalize, around our ICP, that is only possible because of the data flywheel we’ve been building?” If you can’t answer that with specificity, you don’t have a data moat — you have a data warehouse.

The Fundraising Implication Nobody Talks About

I’ve been in the room on a lot of capital raises — across $800M in debt and equity. I’ve watched how investor conversations have shifted.

Three years ago, a strong IP story could carry a lot of weight in a deck. “We have 12 patents pending” read as defensibility. Smart investors always knew it was mostly signaling, but it played.

Today, the investors I respect are asking different questions. They want to know what data you have that nobody else has. They want to understand how embedded you are in your customer’s workflow. They want to see evidence that your product gets more valuable as you accumulate more customers — not just bigger, but smarter.

That’s a data flywheel story. That’s a workflow entrenchment story.

If your defensibility narrative is still built around IP, you’re bringing a 2018 pitch to a 2026 room. That’s not a minor update to your deck — it’s a strategic rethink.

The Uncomfortable Honest Take

Here’s the part that’s hard to say, but important: most early-stage companies haven’t built a data moat yet. They have data. That’s different.

Accumulated data without a system for learning from it isn’t a moat. It’s a liability — storage costs, compliance exposure, and a false sense of security.

The companies building real moats right now are the ones who are intentional about it from day one. They’re thinking about what behavioral data gets captured at every touchpoint. They’re building for workflow integration, not just feature differentiation. They’re treating their data infrastructure as a strategic asset, not an engineering afterthought.

That’s a founder mindset decision. It doesn’t require a massive team or a massive budget. It requires choosing to treat data as a product.

Where to Start This Week

If you’re a founder or product leader reading this, here’s what I’d actually do:

Audit your data touchpoints. List every interaction your customer has with your product. Now ask: which of these generate data we’re actively learning from? Which are we just logging and forgetting?

Map your workflow depth. For each customer segment, draw the workflow your product sits inside. Be honest about whether you’re embedded or adjacent. If you’re adjacent, what would it take to get embedded?

Find one data advantage to name. If you can’t articulate a specific thing you know — about your customers, your market, or your product’s performance — that a competitor couldn’t learn in six months, you don’t have a data moat yet. That’s your starting point.

The window to build this isn’t infinite. Your competitors are figuring this out too.

The good news: data and workflow advantages compound over time. The earlier you start being intentional about them, the harder you become to catch.

IP will still matter in some contexts. But it’s no longer the thing that protects you in the market. What protects you is what you’ve learned and how deeply you’re woven into how your customers operate.

Start there.

Look at Zynga. It had experienced hypergrowth fueled by hits like FarmVille and Mafia Wars. That growth came, largely, from leveraging viral distribution on Facebook. Then Facebook changed their algorithms and growth plummeted.

Have you heard of Crumb’s Bake Shop? In 2003, it was one of Inc. magazines fastest-growing companies. Their growth came on the back of one product: the cupcake. But, the cupcake phase was more of a fad and when it died off they had no secondary products to sustain traffic. Their stock fell from $13 to $0.15 in three years. By 2016, they had shuttered every store.

Concentrated distribution channels and singular product lines aren’t the only reasons that a companies go-to-market strategies start to leak. The challenge is uncovering where the problem lies.

I’ve identified 20 points of potential GTM growth failure and I’ve documented them for you.

The GTM Leak Finder Checklist

There are five phases of my GTM Leak Finder Checklist to step through. Each phase covers a different area of GTM strategies.

Phase 1 = Strategy & Alignment; this is your foundation

Phase 2 = Lead Gen & Marketing; this is the top of your funnel (ToF)

Phase 3 = Sales & Conversion; this is the middle of your funnel (MoF)

Phase 4 = Retention & Expansion; the bottom of your funnel (BoF)

Phase 5 = Growth Mindset; think of it as leadership focused questions

Sample GTM Leak Finder Questions

To give you a failure of the questions, below are some of my favorites. Don’t worry, you can get the entire checklist below.

1. Single-Target Clarity: Can every member of the sales and marketing team name the same Ideal Customer Profile (ICP) for this quarter? My company is running into this right now. But, challenges like this aren’t just for larger enterprises.

2. Sales Playbook: Is there a documented process for handling objections, or is every rep “freestyling” the pitch? I’ll bet there isn’t. Or, if you have documented these things you probably aren’t updating them enough.

3. Proof of Life: Do you have at least three case studies from the last six months that show ROI for your specific ICP? Yes, ROI. If you are a commercial enterprise you should be able to document the ROI of your products/services for your customers.

How to Use the GTM Leak Finder Checklist

The checklist is designed to provide you with a score, so you know how your GTM strategies stack up.

For every question that you can answer affirmatively to, i.e. you can say yes, we do that, put a ✅ beside the question. Or, you can simply count how many you answer yes to.

Each yes is a point and the number of points determines you score.

0-8 = means your GTM strategy is ready for a complete and utter overhaul, or that you don’t have one in the first place.

9-13 = you have a leaky GTM bucket and it’s time to start bailing water.

14-17 = I’d call you a “Growth Contender,” but does your actual growth measure up to how you answered?

18-20 = you are a “GTM Rockstar.” Billy Idol can get over me calling you that.

One key note, be ruthlessly honest with yourself when you are answering these questions. Otherwise you are just wasting your time.

Gtm Leak Finder Checklist

113KB ∙ PDF file

Download

Download

Ready to take the next step?

This checklist can be super helpful, but there’s a difference between uncovering where your go-to-market strategies are going wrong and fixing them.

I asked him one question: “Who is your ideal customer?”

He said, “Everyone in our community.”

That’s not a strategy. That’s hope.

I’ve now had some version of this conversation with dozens of banks — community banks, regional banks, credit unions, digital-…

Read more

I first met Chris, probably 5-6 years ago now, when I joined his Content Marketing Academy.

To this day, CMA was my all-time favorite community to be a part of. Virtually every other member was from Great Britain, but I felt closer to many of them than people in my home time “across the pond.”

Read more

It sounds like a contradiction, doesn’t it? Aggression and comfort usually sit at opposite ends of the spectrum. But in practice, they are a perfect pair. The pursuit of long-term ease requires a high-effort, intentional approach to the decisions you make today.

It manifests in choosing a mod…

Read more

The concept of a “passive” business is largely a myth.

No business is truly, ent…

Read more

There is a common misconception in the professional world: professional career changes aren’t seen in the same light as a founder who just exited their startup after…

Read more

Read more

The instinct is often to hire the “proven” commodity—the candidate with the perfect pedigree and a resume that checks every box. I’ve rarely hired that way. There is …

Read more

The banking in…

Read more

The Q1 2026 funding numbers are in, and on the surface, they look like a gold rush. Venture capital activity hit a staggering $297B, a figure that suggests the “funding winter” has officially thawed.

But look closer at the math, and a much more sobering reality e…

Read more

While traditional banks are still offering 0.5% to 1.5% on deposits, stablecoin rewards have surged into the 4% to 7% range. This isn’…

Read more

Your customers are stuck between two worlds. While 76% of con…

Read more

Most people will never achieve that level of success.

It’s a harsh reality, but it’s rarely because they lack the raw intelligence or the “right” degree.

The truth is much simpler: they are missing two key elements that separate the ultra-wealthy from the merely comfortable.

After an 15-minu…

Read more

Today? The moat is bone-dry, the crocodiles are handbags, and the walls are made of cardboard.

Technology has a funny way of democratizing things until th…

Read more