I had a call last week with a founder of an AI-native go-to-market SaaS company. I asked her what the state of marketing is across the B2B landscape, and she said this:

“There’s no sense of calm in the room right now. Even at the companies that are performing well.”

Her customers are the largest, most-funded and most innovative companies in the world, yet they feel that incapable of aligning their GTM strategy with the complex, ever-changing buying behavior.

The question for companies like Journey, our customers who are small founder-led B2B services companies, and non-technical B2B companies with very limited marketing resources is this:

How do we build a profitable business that grows predictably with a go-to-market environment that puts marketing and sales leaders in a panic?

the panic is real

She walked me through the symptoms of a panicked company in real time. More rebrands than she’s ever seen. Companies launching products at a cadence that doesn’t make sense. Big companies cloud-chasing little ones, something they used to ignore. CEOs in the weeds on decisions they used to delegate. AI SDRs everywhere, because nobody can afford to miss a single lead.

“I used to spend 20 hours building one deck. Now with Claude I can produce 100 decks. So I produce 100 decks. Which is the wrong way to think about it.”

That’s the panic loop in one sentence. Everybody got faster, so the bar moved to “more.” Now everybody’s drowning in their own output and nobody knows what’s actually working.

The instinct in panic is to reach for the lowest-hanging fruit. Move spend from one channel to another. Swap a tool. Run another rebrand. Ship more decks. None of those are wrong, exactly. They’re just stitches. The bleeding has a deeper cause.

what actually changed

The deeper cause is that buyers changed and we kept marketing like they didn’t.

A few numbers I’m sure we’ve all read somewhere on a LinkedIn post:

• 67% of B2B buyers prefer a rep-free buying experience. That’s from a Gartner survey in March 2026. Up from 61% the year before.

• 80% of B2B buyers complete ~70% of the buying journey before they ever talk to a sales person. From the Demand Gen Report. And it’s the buyer who initiates the first call, not us.

• AI now covers 65-75% of that independent research. Pedowitz Group. The shortlist is being built in 10 minutes inside ChatGPT, with no human involved.

• HubSpot’s customers saw a 27% drop in organic traffic year over year, while AI-driven traffic converts higher. That’s HubSpot’s own data, April 2026.

• 58.5% of Google searches end with zero clicks because AI Overviews answer the question before the user thinks about scrolling.

The shortlist is built before you know there’s a deal, which means those early decisions are being made with whatever buyers can find on their own.

As a result, the first conversation isn’t that discovery call (or Assessment Call, which is what how I learned it). Instead, that first synchronous conversation is confirmation. By the time someone fills out your demo form or even trials your tool, they’ve already talked to ChatGPT, three peers in a Slack group, all the available content, and probably a Reddit thread.

This is the thing that is making me panic (along with every other more successful, more resourceful, and more intelligent operator): the funnel I built all my businesses on doesn’t exist anymore.

the value of information

Here’s why this applies to me, Journey.io, and our customers who use Journey.io to transmit information to clients, prospects, and others.

The vast majority of sales collateral was built for a world where a rep walked the buyer through the material. Decks, one-pagers, case studies, PDFs. The rep was the operating system. The collateral was the apps.

However, if 80% of the journey happens without a rep, the collateral is the operating system now. It has to work on its own. It has to be skimmable, interactive, trackable, and re-shareable inside a buying group without losing the plot.

A static PDF can’t do that. A 47-slide deck attached to an email can’t do that. A folder of links can’t do that.

• Gartner projects 30% of B2B sales cycles will run through digital sales rooms by 2026.

• 86% of enablement leaders say their reps use less than 60% of available content because it’s stale, hard to find, or doesn’t fit the moment.

• Buyers want short-form (67%) and webinars (65%). Appetite for “interactive content” actually dropped from 49% to 38%.

The translation: stop sending stuff. Start building experiences that travel through a buying group on their own.

how a small services company gets its name out in 2026

Most of my customers at Journey.io aren’t running enterprise marketing orgs with a Rolls-Royce GTM tech stack. They’re founders. Agency owners. Services teams running on Notion.

If 67% of buyers don’t want to talk to you, and 80% of the journey happens before they do, how does a five-person services company even get on the shortlist?

Here’s are two things:

1: the corporate voice is dying. Trust now flows from human practitioners, not companies and logos.

• Eric Eden posted ~1,100 pieces of content on Reddit, racked up 21M reads, built 25K subscribers, and generated more inbound advisory work than most agencies do in a year.

• Clay.com hit $100M ARR pumping out 3,000 pieces of content per quarter, most of it from partners and customers, not their in-house team.

The cheapest channel left is your face, your voice, and the unsolved problem you can’t shut up about.

2. be useful where the panic is. This was the most useful thing the founder said on our call. When she sees somebody post on LinkedIn or Reddit — “I’m trying these five things to get more traffic, none of them are working” — her team doesn’t pitch. They reply with information. A perspective. A diagnostic. Sometimes a free piece of analysis with no strings.

The pitch comes later. If it comes at all.

Build credibility by being the person who showed up before the deal existed.

what this means for what i’m building

Journey.io needs to find a space around this panic.

A Journey link replaces the file dump. One link, all the assets a buyer needs, structured like a story instead of a folder of files. It travels through the buying group without losing the plot. And on my side, I can see who opened it, what they read, how long they stayed, when they came back. The visibility I lost when buyers stopped talking to me is soemthing I get it back through the content itself.

The information isn’t the support material for the sales process. The information is the sales process.

That’s it for this one. Let’s keep it going.

Cheers, Danny

Took a few extra days between issues this week because we were down in Austin for my nephew's first birthday.

Last issue I pulled a quote from Alex Turnbull at Groove. He called his company an “NRR zombie” — $4.5M ARR, solid retention, healthy NPS, and MRR down every single month for 14 months.

His line that stuck with me: the market is slowly moving while you keep the lights on.

I’ve been sitting with that frame for a couple weeks now, and I feel like his description of Groove is a very strong description of Journey.

Our best customers love us. They add users every month. They use the product for the reasons that generate the most value, but I’m getting fewer and fewer of these customers. More and more of the customers that aren’t our best… they churn faster.

The market is moving (I think faster than I would like) while I’m trying to keep the lights on.

There is something to be done with this. I’m not exactly sure what, but I’m thinking through it.

in an AI world, SaaS without PMF makes less sense than ever before

In the last 30 days on Journey, I’ve had:

• A handful of upgrades from customers I haven’t talked to in months

• New paying signups from industries I wasn’t targeting

• One churn from an account I was half-sure would become a reference story

I’ve tried to draw a line through these. I can’t. Just motion, in both directions, cancelling itself out most weeks.

the 50/50 answer i can’t give

Last week I was on a call with a prospective buyer kicking the tires on Journey. He asked a question I’ve been dodging in my own head for a year: why do some customers care about how their content is packaged, and some don’t?

I told him the truth. It’s about 50/50. Half my customers hear the pitch and say “I really, really, really care about how my stuff looks when I send it out.” The other half shrug and say “I don’t care, email works fine.”

I’ve never cracked the signal that tells me which half a person is in before I get on the call.

Firmographics don’t predict it. ICP filters don’t predict it. I’ve built signals models in Clay trying to. None of them hold up. People buy software for reasons they can’t fully explain to themselves — let alone to me.

what alex got right

Here’s where the zombie frame lands for me.

The surface looks stable. The net numbers say fine. But underneath, something is moving. The market is moving. The buyer’s emotional model for how they pick software is moving. And while all of that is moving, I’m keeping the lights on and calling it retention.

Staying the same is not staying the same. It’s a slow drift you don’t see on the dashboard until it’s too late to react.

The scary part isn’t the drift itself. It’s that the drift isn’t a logic problem I can out-think.

the lever i actually have

If I can’t reliably grow demand I can’t explain, the only variable fully in my control is how long I can stay in the game.

That’s burn rate.

I’m mid-audit, but the list I’m working through right now:

• Growth experiments. Paused or killed the ones without a clear signal. No more “let’s see” budget.

• Attio. Reconsidering whether we need the full CRM stack or if a lighter setup gets us 90% of the way there.

• Customer.io. Same question — are we using enough of it to justify it, or can we consolidate into something simpler?

• Polytomic. Data sync is real, but so is building the pipe we actually need in n8n for a fraction of the cost.

• Raaft. Nice-to-have retention flow. Not load-bearing.

None of these are bad tools. They were the right call when we were spending like the market was still growing up and to the right. They’re not the right call when the signal is “stay in the game.”

The AI-native founders I’ve been paying attention to aren’t special because they found some trick. They refuse to rent leverage they can build themselves with Claude, n8n, and a few Claygents stitched together. They own the automation instead of subscribing to it.

That’s the operating model to manage the ambiguity and the lack of patterns that are more dominant in businesses without PMF in an AI-first world.

what i need to build on

Alex’s post had a line underneath all the hard numbers that stuck: your best customers still love you.

That’s my situation too. Power Knot is still paying. Long Angle is still embedding Journey into their whole community experience. Half my calls end with someone saying they really, really care.

I just can’t predict who the next one will be, so I have to cut the fat. Let the randomness run. Trust that the customers who care.

That’s it for this one. Let’s keep it going.

Cheers, Danny

fun stuff

We were in Austin last weekend celebrating my nephew’s first birthday.

The other thing that made this week: my son’s first school dance as a kindergartner.

I took last week off for Easter, but I’m back.

A few weeks ago, I was on a wrap-up call with Steve Brady — he’d been helping me build and test an outbound system for Journey. Clay tables, Claygents, PQS-based prospecting across three ICPs. The architecture was solid. The signals were dialed. The execution was about as good as it gets.

The results were not.

And at the end of that call, I said something I hadn’t said out loud before: I don’t know if I should keep doing this.

That’s where the numbers pointed, but I think there are more options than just letting something go when it seems there isn’t a solution in sight (at least in this situation).

fun stuff (before we get into things…)

Over the long weekend, we were craving some pizza, so we decided to go check out one of the more famous spots in the Dallas area, Fortunate Son, a spot that Dave Portnoy reviewed.

Anyways, it was delicious. We waited 30 minutes for a table, the kids got hanger, so we actually went next door to eat and ordered the pizza to-go. My wife and I then had the pizza as a late-night snack, but it was still one of the best.

It’s New Haven-style pizza. Not sure what that means, but it was very good.

the flaw that keeps me here

I have never been able to grind on something that doesn’t mean anything to me. Even if the economics make sense. Even if it’s the rational move. Even if it makes a ton of money.

At XO Capital, we acquired 12 SaaS companies in about four and a half years. Mostly, we flipped profitably. A couple — AI bets — wrecked us. Across all of those, the ones where I did my best work were the ones I actually cared about. The ones where I was just operating for the return? I could feel the drag every day.

Journey is the one I held onto, partially because I really had a lot of passion for the idea, the problem, the opportunity, and the bones of the business. Long story short, it hasn’t been what we expected. There are a lot of things outside the business that are making an impact on this road to PMF, but even after executing some of the best GTM experiments I could, the numbers say quit. I have to disagree. That’s either conviction or delusion.

I genuinely don’t know which one yet.

what i learned from a friend

I read a piece this week from the Wildfront guys. two dudes I’ve come to admire and look up to, called “Who you’re building for determines if SaaS is dead or not.”

The sentiment they shared was basically if you’re selling SaaS to indie hackers and technical founders, you’re fighting uphill. They’ll vibe-code your tool over a weekend. But if you’re selling to people too busy running their businesses to build their own tools — agency owners, sales leaders, marketing teams — SaaS is alive and well.

Journey lives in that second world, thankfully. Our customers aren’t trying to replace us with a weekend project. They’re trying to close a deal, so I know we’re in the right market.

The question is whether I can get in front of enough of the right people to prove it.

Alex, the author, mentioned another Alex, the founder of Groove (see screenshot above).

I am experiencing this. We don’t have a churn problem, per say. The number is generally sub 5%, but we don’t grow, so we slowly become zombies.

The best customers definitely still love us, but the market is moving…

1. Where is it moving to?

2. Why is it moving from where it was?

3. How is it moving?

4. When will it stop?

5. What does it mean for small companies like us, based on the direction it’s moving?

I’m not sure.

keep doing the work

I’ve been testing Gojiberry.ai for outbound — an AI-powered lead gen tool that tracks intent signals and surfaces warm leads. People engaging with competitor content, searching keywords in your space.

1,537 leads in my Manufacturing ICP alone. Campaign running since March 8th. 675 leads touched. 45% connection rate. 26% reply rate.

And out of all that: 4-5 genuine yeses.

4-5 out of 675.

It’s not a flood. It’s a handful of real humans who said “yeah, I need that.” And right now, that’s enough to keep going.

passion is the only thing that survives this part

The Wildfront piece makes the point that the bar has gone up in SaaS. You can’t build a good product and coast. I agree.

But I’d add: you can’t survive the pre-PMF grind on discipline alone. Discipline gets you through a quarter. Caring about the thing, really caring, is what gets you through a year of flat growth and out the other side.

Eric, my first boss at RevBoss, told me something twelve years ago: always run towards something, never away from something. Journey has been the biggest thorn in my side, but it’s a great battleground for my passion. Some months, I fail it. Some months, I’m just running toward something I can’t fully see yet.

But I’m still running.

That’s it for this one. Let’s keep it going

Cheers, Danny

Sorry for the delay on this one. I wanted to get permission from the folks I referenced before shipping this one…

Last week, I got the results back from the most expensive experiment I’ve run at Journey. I hired one of the best GTM operators I could find, someone who builds outbound systems for a living, and gave him a simple brief: build the Porsche of go-to-market engines for Journey, and let’s see what happens.

The goal was to get to a repeatable, predictable playbook as quickly as possible for one of the several niche segments we honed in on during our customer deep dive prior to the experiments.

As a founder of a start-up that doesn’t have PMF, I’ve learned something that is hard to say:

For a pre-PMF company like Journey, ANY concrete outcome, either good or bad, from a go-to-market investment is extremely valuable. It’s a hard pill to swallow, but failure from a go-to-market investment is an important data point that helps you know where to STOP investing, where to STOP digging, and where to STOP being hopeful.

fun stuff (before we get into things…)

went to a family wedding in Fredericksburg this past weekend. it was 99 degrees, and we were in Texas hill country celebrating my wife’s cousin.

the boys had a great time… i was just surviving the heat.

a reminder on what we built

For commercial real estate investment funds, we wrote a Claude Code scraping tool that crawled every SEC Form D filing from the past two years. It pulled how much each fund raised, how many funds they managed, whether they were actively raising, whether they had a portal on their website, the number of downloadable PDFs on their site. Eight qualification criteria, all extracted automatically, all feeding hyper-personalized outreach that referenced each fund’s specific situation.

For industrial manufacturing, similar depth. Scanning for 3D renderings on company websites. Counting downloadable CAD files. Finding YouTube channels with webinars and referencing exact view counts in the messaging.

It was the best segmentation and personalization I’ve seen. Every message was crafted with a level of specificity that should’ve made the recipient stop and think, “wait — this person actually understands my business.”

It got nothing. Crickets. Hundreds of contacts, multiple segments.

is it just me and Journey?

I got some additional context from other companies to understand their GTM experience.

A recruiter reaching out to YC founders in Europe with pre-qualified candidates for their open roles — a proven cold offer. A VC partner reaching out to healthcare founders offering free advice from a three-time CRO in their space. A D2C e-commerce play targeting founders of brands with 7+ years in business, under $30M raised, positive growth signals.

Every single one. Brilliant targeting, thoughtful messaging, legitimate value. Crickets.
The recruiter got one guy who said “I’d be keen to look at your candidates” — and then the thread went dead the second it pivoted toward a sales conversation. The D2C campaign? 7% LinkedIn acceptance rate, essentially zero replies.

This isn’t one company with a bad product. It’s a pattern.

post-effort

I was catching up with a founder friend who said something on a call that describes the change we’ve seen in GTM: “We’re in a post-effort world.”

He means that hard work, smart execution, and relentless iteration used to be enough to scale a GTM engine. You could write better emails, test more subject lines, refine your ICP, improve your sequences, and results would compound. That flywheel doesn’t spin the same way anymore.

Three years ago, the personalized landing page Steve built — one that basically says “I went through your entire business and here’s a mini-proposal” — would have blown people away. Today? Nothing. Not because it’s bad. Because the threshold for what earns someone’s attention has shifted so far that even exceptional execution doesn’t clear it.

it’s not just outbound

I recently read PricingSaaS’s 2025-2026 analysis of PLG vs. SLG across 498 SaaS companies. The data tells a remarkably similar story from the product side.
The line between product-led and sales-led growth has collapsed. Companies aren’t picking one model — they’re mashing them together. Of the 40 companies that changed their freemium model in 2025, roughly half tightened or eliminated free access and the other half expanded it. The market isn’t moving in one direction. It’s splitting.

Credit-based pricing adoption grew 126% year-over-year. Figma went through the entire AI monetization lifecycle in four quarters — standalone add-on to embedded credits to free-tier credits — searching for the right model in real time. Notion killed its $10/month AI add-on entirely and just baked AI into every plan, metered by usage.
These are companies experimenting at speed because the old assumptions were showing signs of slowing their business down.

The report’s core finding — PLG and SLG have collapsed into one thing — mirrors exactly what I’m seeing on the GTM side. The distinction between inbound and outbound is dissolving. And what’s replacing it feels less clear, at least for us.

the gap

The GTM operator I hired made this point better than I could: everything he builds now, he tells his clients, is not a meeting generation system.

It’s an awareness system. The goal isn’t to get someone to say yes to a call. The goal is to figure out if they’re even willing to assess whether they have the problem you’re trying to articulate.

The sales process used to be: top of funnel → discovery → demo → evaluation → close.

Now there’s this vast, unmapped territory before the funnel even starts. A space where you’re trying to create enough trust and deliver enough value that someone will eventually, on their terms, when they acknowledge they have the problem you solve, consider you.

That’s a fundamentally different business than most of us planned for.

the uncomfortable part

I started this experiment thinking there were two outcomes: either we’d find a glimmer of traction I could pour fuel on, or we’d get a definitive signal that these initial set of hypotheses were not going to work.

I got the second one. From the best operator I could find. Using the most sophisticated tools available. With messaging that was objectively excellent.

And that means something. Not just for Journey, but for how I think about what’s possible in B2B right now.

Either you have the perfect product for the perfect problem at the perfect time — lightning in a bottle, the kind of PMF where go-to-market almost doesn’t matter because the pull is that strong — or you commit to the slow, trust-based, audience-first approach that takes months or years to compound.

The world where you could have “somewhat” PMF and scale it through GTM effort? I think that world is gone.

The opportunity though is that there are a new set of hypotheses to go test (for example, are these people more available to reply via email?).

More on this to come…

Let’s keep it going.

Cheers, Danny

I went on LinkedIn the last couple of weeks and downloaded every "free resource" I could find. Lead magnets, playbooks, templates — you name it. I just clicked the button, gave my email, and collected whatever landed in my inbox.

Out of maybe 50 downloads, I’d say four or five were actually useful. The rest felt like they were written by a prompt, not a person. Solid enough formatting. Nice enough design, but definitely felt like lacking.

It’s so easy to make “good enough” now that it’s everywhere…

fun stuff (before we get into things…)

had some great weather this past week (and not so great weather as well), but regardless, the boys were vibing and enjoying the nice March weather.

didn’t take any pictures this week.

content creation

There was a time when creating a solid case study, a polished one-pager, or a sharp product video required real resources. A designer. A writer. Budget. Prioritization. Most companies had client stories, usage data, industry reports, but getting it packaged into something usable was a bottleneck.

That bottleneck is gone.

Tools like Gamma and Canva can generate a deck in minutes. LLMs can write a first draft of nearly anything. The creation barrier basically evaporated.

I’ve been testing building custom Journeys for B2B services companies, and I took a company’s animation process and built it into a Google Slides and then used Google Slides video converter to have a walk-thru of our animation process (and added it to a Journey)

CMI’s latest report surveyed over 1,000 B2B marketers and the data tells the story clearly: 91% of B2B marketers increased their content output in 2025. But 39% say maintaining voice and quality is now their top challenge. 68% of B2B buyers say all brands look and sound the same.

So we’re producing more than ever. And it’s all starting to blur together.

the question i have

Content and resources are supposed to be one of the main mechanisms for building trust with prospects and customers. That’s the whole point — provide value, build the relationship, earn the conversation.

But if everyone has access to the same creation tools, and the volume of content keeps climbing, how do you actually stand out?

my dad

I’ve talked about this before, but it keeps proving itself true.

My dad runs a frame shop. When I bring him something meaningful, a photo, a certificate, whatever, he doesn’t just grab a frame off the shelf. He asks what story it needs to tell, then makes the presentation match the meaning.

If it’s valuable, he suggests museum glass so it preserves. If it’s something with texture and depth, he’ll built it into a 3-D shadowbox. If it’s a collection of items, he’ll add a name plate for context. Everything deserves the right packaging.

I think B2B content has the opposite problem right now. Companies are investing in creation but completely ignoring delivery. They’ll spend weeks building a great case study, then send it as a PDF attachment in a cold email with three other links and a “let me know if you have questions.”

All the intentionality they put into making the content gets destroyed by how they share it.

what I mean by packaging (and why I think it matters)

I built four sample Journeys last week for real prospects. Let me walk through what I did and why.

I took a video production agency, a water treatment company, a few others, and I went to their websites. I pulled their YouTube videos, their services pages, their process animations. Stuff they already had publicly available.

Then I took some of that raw material and used AI to build supplementary content, like turning a services page into a clean visual asset, or restructuring their animation process into something more digestible.

Here’s the key part: I packaged it all into a single Journey. One link. Everything sequenced intentionally: watch this video first, then see this breakdown, then here’s what working together could look like.

Compare that to the alternative: three YouTube links, a PDF, and a PowerPoint dropped into an email thread. Same content. Different experience.

With the Journey, I can see what they watched, what they skipped, how long they spent on each section. With the email dump, I’m just hoping they opened the attachment.

(You can see the four examples here: Snowy Peak · Cloud in the Sky · Sample 3 · AquaCycle)

the data says delivery matters, but the market isn’t acting like it

I had no idea if this is a real problem or just a me thing, so I went out looking for data to prove my point lol…

Gartner’s latest sales survey found that 67% of B2B buyers now prefer a rep-free buying experience. They’re self-educating, self-qualifying, and making decisions before they ever talk to a human. The content they consume during that process is the sales conversation for most of the journey.

6sense’s 2025 Buyer Experience Report found: 95% of the time, the winning vendor was already on the buyer’s shortlist on day one. And the vendor the buyer contacts first wins roughly 80% of deals.

So the content you send before that first conversation isn’t just marketing collateral. It might be the most important sales interaction you have. And most companies are still delivering it as a pile of attachments.

Meanwhile, Gartner is telling enablement leaders to “structure content into modular, agent-ready building blocks that can be dynamically assembled into context-aware resources.” Not sure what that means exactly, but to a simple person like me, it’s translated to: stop sending static PDFs and start thinking about content as an experience you design.

back to PMF

Some of our customers at Journey completely agree with this. They see the packaging, the sequencing, the engagement data, and they get it immediately. The “aha” is instant.

Others don’t care. They’re fine sending the email with five attachments. And their deals still close.

So is this a real problem, or is it a problem I want to exist because it’s the one Journey solves?

I don’t know, but the experiment I ran, building those four prospect Journeys, taught me that the act of curating and sequencing someone else’s content forced me to actually understand their business.

The packaging process was the research process. And the output was something I could send that demonstrated I’d done the work, without ever saying “I did the work.”

That feels like it matters. Whether it matters enough to change buying behavior at scale is the question I’m still trying to answer.

what I think is true (but can’t prove yet)

Content creation is now table stakes. Every company can produce decent stuff quickly.

The next layer is how you collect disparate content into a single experience, how you prescribe what to consume and in what order, how you add context that makes each piece more valuable than it would be alone, and that’s where the gap is opening up.

When you send a bunch of links in an email, all the prescription gets lost. All the intentional sequencing disappears. And the insights about what your prospect actually engaged with? Gone.

I think that gap is going to mat

ter more, not less, as content volume keeps climbing. But I’m saying that as someone who builds a tool that addresses exactly this problem.

That’s it.

Let’s keep it going.

Cheers, Danny

Last week I wrote about pivoting from CRE to manufacturing, breaking the ICP into three Pain-Qualified Segments, and building the Clay pipeline that runs enrichment automatically on 90+ contacts.

If you missed it, the short version is: CRE signals were slow, the TAM was narrow, and the outreach required too much manual research per prospect. Manufacturing is a better fit: physical products that can’t demo on Zoom, long email-heavy sales cycles, and a clear gap between having HubSpot and not having anything to actually deliver sales content through.

That post went out March 5.

I had met up with Steve the next day, and it surfaced some things I want to document.

fun stuff (before we get into things…)

my eldest had a birthday party last week, so it was super fun to see friends and family get together to celebrate that.

also, getting my 2.5 year old into baseball, so we’ve been going outside to get some swings in every other day.

fun times.

the honest pulse check on linkedin

Steve opened the call with a question I didn’t have a clean answer to: how do I feel about LinkedIn as a channel so far?

And honestly, I can’t tell.

Connection rates are normal. In-mail reply rates are better than email typically performs. So there’s nothing that says the channel is broken. But we’re doing something with a finite group of people over a finite window of time, and those experiments always feel inconclusive early. I’ve learned this from running outbound… you almost always have to wait longer than feels comfortable before you know anything.

What I’ve been sitting with is a different fear: that it’s not the channel, not the targeting, not the copy, but something about the offer itself.

the gamma question i keep avoiding

When Steve and I first connected, he sent me a Gamma, my first reaction was to immediately compare it to Journey. And I had a hard time.

Gamma is free. You can embed videos in it now. You can add calendar links. You can build something that looks well-designed from a prompt in about two minutes.

So what does Journey actually do that Gamma doesn’t?

It was hard for me to put together a good, valid answer.

What I came back to was something that came up in a separate conversation I had with another founder (shout-out Ken and meetsona.ai) who had described his ICP in a way I’d never heard before:

“I’m not targeting the person who needs to post more. I’m targeting the person who’s scared to post.”

His platform is built around authenticity, not virality. He’s not competing with the volume tools. He’s serving a completely different emotional state.

It was helpful because the thing I’ve been telling myself about Journey — that I’ll never compete with AI tools that create content at scale — is actually the right instinct. Gamma has that. Claude has that. Canva has that. Journey isn’t about generating the content.

Journey is about prescribing the order in which your content gets consumed.

I actually ran into this recently when I recorded a Loom explaining five or six things and then I also needed to send the recipient the actual things I was showing.

Two links, two PDFs. So I sent the Loom with four attachments in an email.

And then I sat there thinking: he’s going to watch that Loom right before a meeting, close out of email, and never open those attachments. And if he goes looking for the Loom later, he’ll have to find the email, re-open it, and hope the attachments are still there.

So I put everything into a Journey. One link. Video at the top. Supporting docs in order. Now if he goes back looking for that video, everything’s right there with it.

Steve put a name on it at the end of the call: it’s a packaging problem. Not a content creation problem. Not a design problem.

A packaging problem.

We’re not building a deck builder. We’re building…. something else haha (and I don’t know what that punchline is yet)

what changed about the offer

The last newsletter described the outreach close as: “I built a sample of what your product line would look like as a Journey using your public content. Want me to send it?”

That framing came from before the call. After the call, it’s shifted.

The version Steve pushed toward is: don’t ask if they want to see it. Build it for them specifically, from their actual assets, and send it. Include it in DM1. Include it again in DM2. Put it in every message. Don’t gate it behind a question.

The whole point of the permissionless value prop is that they already have it before they agree to anything. The ask isn’t “would you like to see what this could look like.” It’s “I already did it — here’s the link.”

There’s a practical constraint worth naming: Journey doesn’t currently make it easy to automatically ingest assets. Text is simple. But pulling in actual PDFs and spec sheets programmatically — that’s harder with the way we track assets on a page. So for now, this is semi-manual. I go to the prospect’s website, pull their product pages, find what’s there, and build it.

sprint 3: founder-led b2b services

We also planned out the third outbound sprint on the call: founder-led B2B services.

The people I have in mind are solo operators and small teams running video production companies, creative agencies, design studios — people who sell visual work, and share that work via Google Drive links with file names like “ClientX_Final_v3.mp4.”

The pain is that the delivery undermines the work. If you’re a video production company charging $10k a project, sending a Google Drive folder is a bad first impression. Your work is only as strong as the frame you put it in.

We have existing customers that fit this. And one that’s quite interesting is a Hollywood game show producer who pitches major networks. Before Journey, he was sharing scripts, mockups, and sizzle reels in a folder. Execs would click around randomly. With Journey, he controls the narrative arc. He can see that NBC watched his video. He can see that Paramount spent time on the storyboards. That’s not a Gamma feature. That’s a different problem entirely.

The challenge with this segment is unit economics. ACV is $39–50/month, which doesn’t support the same level of outbound we’re running for manufacturing. So the channel strategy is different:

• Content-led inbound — post about the packaging problem, attract founders who recognize it

• Lightweight LinkedIn engagement — show up consistently, DM softly

• Lookalike lists from existing customers

• Native LinkedIn video — Steve’s suggestion, and I think it’s right. Record yourself walking through a Journey you built for a lookalike company. Send it as a DM. For someone who cares about visual quality, a scroll-stopping thumbnail is a more compelling cold touch than any text message.

This one is next on the list to try.

the intent question

One more thing from the call that’s worth documenting.

Steve made a point about buying intent data that I’ve thought about a lot since: it’s been promised for 10–15 years, and it mostly doesn’t work. The exceptions are when the signal is structurally forced — a government permit, a job posting that mentions specific tooling, something mandated and therefore reliable. But for most B2B SaaS, you can’t get a clean read on who’s “in market” from third-party data.

His framing: stop trying to find intent. Start engineering it.

Cold traffic becomes warm traffic when they click your Journey link. Warm becomes hot when they visit your pricing page, or open the Journey you built for them twice. You can’t know who woke up ready to buy today. But you can message enough of the right people that when they do wake up ready, you’re the first thing that comes to mind.

This is why the Journey link goes in every message. Every click is a signal I generated. If someone opens the thing I built for their company and spends four minutes on it without replying, that’s information. That’s warmer than silence, and I know it from data I own, not from a third-party platform guessing.

so where are we

Manufacturing sprint is live. I’m watching connection rates, click rates on the Journey links, and waiting long enough to actually learn something.

Sprint 3 planning is done. Founder-led B2B services is next.

And I’m sitting with a cleaner answer to the Gamma question than I had a week ago, even if I still have to figure out how to say it in a cold DM.

More soon.

Let’s keep it going.

Cheers, Danny

Dan Layfield wrote something on HackerNoon this week called “AI Isn’t Ending SaaS — It’s Rewriting the Playbook.”

His argument is that the fundamentals of building a business haven’t changed. You still must find an arbitrage, get profitable distribution, build defensibility, but the way you execute against those fundamentals has shifted faster than anything since the internet.

He uses this analogy about the forward pass in football: when it was introduced, it changed how the game was played, but not what it takes to win.

You still needed to score more points.

What we’re doing right now at Journey isn’t changing what we sell, but instead, it’s changing how we find the people who need it, how we prove we understand their problem, and how fast we can do all of that before they default back to the status quo.

The product-led growth motion feels quite different.

fun stuff (before we get into things…)

We have a lot of family coming over this weekend, so should have some fun updates.
Kids were sick and family was busy, so we don’t have a ton of things to share here today.

Sorry!

where we were four weeks ago

When I wrote the last newsletter about competing against status quo, I was still mostly thinking about CRE funds as our primary segment. That was our first real experiment for the PQS framework: SEC EDGAR filings, BuiltWith scans, identifying funds actively raising capital with no investor communication system.

Good segment.

We have a customer paying ~$500/month there.

But the problem was the data signals were slow. SEC filings have lag. The total addressable market of small CRE funds actively raising at any given time is narrow. And the outreach motion required a lot of manual research per prospect.

So we decided to move on and take a look at the manufacturing space that also currently occupies a good chunk of MRR for Journey.

why manufacturing

Here’s the insight that kicked this off. Steve said it during one of our retros:

“Some things, you don’t need information to buy. Candy, for example. With these guys, the information is essential to the purchase.”

Manufacturing companies sell physical products that are too large, too complex, or too dangerous to demo on a Zoom call. A 50,000 lb food waste digester. Industrial conveyor systems. Custom-fabricated steel components. The buyer can’t see the product until it shows up on a truck. Which means the content — the spec sheets, the renderings, the dimension drawings, the case studies — that content is the product demo.

And right now, the way most of these companies share that content is: email attachments. PDFs. One at a time. Into a thread that will have 50–60 exchanges over a 6+ month sales cycle. By month four, neither the rep nor the prospect can find anything.

This isn’t a theoretical pain point I’m guessing at. Our customer Power Knot sells food waste equipment — literally 50,000 lb machines. Their VP of Marketing wants her sales team to have access to which prospect is actually looking at the specs for the LFC-200 versus who said “thanks, we’ll review” and went dark.

That’s the kind of pain where Journey finally isn’t a vitamin.

three segments, one ICP

We didn’t just pick “manufacturing” as a segment and blast emails. We broke it into three Pain-Qualified Segments, each targeting a different pain and a different buyer persona.

PQS #1: “Complex Product, Can’t Demo on Zoom”

This targets VP of Marketing and Sales Directors at companies selling physical products with extensive technical documentation. The core insight is that when the product can’t be demoed, the content IS the selling. Journey becomes the product demo that a Zoom call can’t deliver.

PQS #2: “Sales Reps Drowning in Email Threads During Long Cycles”

This targets Sales Directors and VPs of Sales at companies with 3–12 month enterprise cycles. Each deal generates 30–60 email threads. Reps can’t find what they sent, prospects reference outdated versions, and leadership has zero visibility into which deals have engaged buyers. Journey’s “single link that grows over time” value prop was built for this exact pain.

PQS #3: “Marketing Team Can’t Enable Sales with Product Content”

This enters through the marketing persona. Marketing creates beautiful product content — renderings, videos, case studies — but the moment it leaves marketing’s hands, it becomes email attachments with ugly file names. This is our path to multi-seat expansion: marketing builds the Journeys, sales distributes them, both get value. And at a fraction of what Highspot or Seismic costs.

the data recipe: how we actually find these companies

This is where the playbook has changed, so I’m learning as I go with people like Steve.

And this is where Layfield’s point about AI reshuffling execution really shows up in practice.

We built a hybrid enrichment pipeline in Clay that combines native integrations with Claygents.

Here’s the actual architecture:

BuiltWith (native Clay integration) scans a company’s website and tells us their tech stack. We’re specifically looking for two things: does this company run a CRM like HubSpot or Salesforce? And do they have a sales enablement tool like Highspot, Seismic, or Showpad? If the answer is “yes CRM, no enablement tool” — that’s our gap. That’s the whitespace Journey fills.

Then we run four Claygents in parallel. One analyzes product pages for complexity — is this a physical product? Is it large or complex? How many product lines? How many downloadable PDFs? Another scans job postings for sales cycle indicators — mentions of “long sales cycles,” “complex sales,” “technical sales.” A third maps the sales team size and hiring activity. A fourth assesses marketing content quality and team structure.

All of this runs automatically.

A company enters the top of the Clay table as a domain name. By the time it reaches the bottom, we know: what they sell, how complex it is, what CRM they use, whether they have a content platform, how big their sales team is, whether they’re hiring, and how much marketing content they’ve produced.

From there, a routing formula assigns each company to a PQS (or disqualifies them entirely). And each PQS routes to a specific message template with variable fields pulled directly from the enrichment data.

A year ago, this pipeline would have required a full-time SDR spending 30–45 minutes per prospect doing manual research.

Now it runs in the background.

the outreach: showing up with the value already delivered

In the last newsletter, I talked about competing against status quo and how the old approach was basically asking prospects to imagine a better future? And how that doesn’t work because status quo bias means they’ll default to “we’re fine”?

For this experiment, the sequence runs through HeyReach on LinkedIn. Day 0 is a blank connection request — no note, because acceptance rates are higher without one. Day 1, after they accept, is the real message. And this message is built entirely from the enrichment data:

We tell them we went through their product pages. We reference the specific number of product lines we found. We note that they’re running HubSpot (or whatever CRM) but don’t have a sales content platform. Then we name the gap: their reps are probably downloading PDFs from the website and emailing them to prospects as attachments.

And then the close isn’t “want to hop on a call?” It’s: “I built a sample of what your top product line would look like as a Journey using your public content. Want me to send it?”

That’s the shift.

what’s actually different about this versus how i used to do it

I want to name the specific things that have changed because it reminds me of the work I still need to do:

The research happens before the message, not during it. In the old world, a rep would google a company, skim their website, and write a semi-personalized email. Now the research is automated and systematic. Every company gets the same depth of analysis.

The segmentation is pain-based, not demographic. We’re not targeting “manufacturing companies with 10–200 employees.” We’re targeting “companies selling physical products too complex to demo, with a CRM but no content platform, and 3+ sales reps.”

The first touch delivers value, not a request. The standard outbound motion is: interrupt someone, describe a problem they might have, ask for 15 minutes. Our motion is: interrupt someone, show them we already understand their specific situation, and offer to give them something useful for free.

Disqualification is built into the system. If a company already uses Highspot or Seismic, they’re automatically disqualified — we don’t compete where there’s an entrenched solution. If they’re not actually a manufacturer (software/services), they’re out. If they’re over 500 employees, they’re outside our pricing sweet spot. This means every message that goes out has already passed through multiple qualification filters. We’re not spraying.

so what?

You’re right. So what… if it doesn’t work.

I’m running this test now, so I’ll share if I find it to net better results than the last segment.

But at the end of the day, right now, these are all just words because I don’t know.

What I do know is that this motion is structurally better than anything we’ve run before. The research is deeper, the targeting is tighter, the message is more specific, and the value delivery is upfront rather than gated behind a demo request.

The thing Layfield wrote that keeps rattling around in my head is his point about arbitrages: every great business opportunity eventually gets competed away. The window for using AI-powered enrichment and personalized outreach at this level of specificity is open right now. It won’t stay open forever.

For me, the question is whether we can use that change to solve our own status quo problem: the one where we know our product works, our best customers love it, but we haven’t been able to find enough people in the exact right situation to hear about it.

More soon.

Let’s keep it going.

Cheers, Danny

Steve and I were reviewing messaging copy for our manufacturing outreach last week, trying to figure out why the pitch still felt like a vitamin instead of a painkiller.

And he just said it plainly:

“You’re not competing against other vendors. You’re competing against status quo every single time.”

I’ve heard variations of this before. But this time, I actually went looking for why it’s so hard to beat.

I came across a post by Chris Adams that framed it as temporal myopia — the tendency to make bad long-term decisions in order to preserve short-term comfort.

The prospect understands the problem. They nod at the pain. And then they do nothing, because doing nothing is free, familiar, and carries zero risk to their reputation.

Adams breaks down exactly why the status quo is so sticky: there’s no urgency because the current system “works well enough.” There’s perceived risk in switching: the learning curve, the productivity dip, the fear of championing something that fails.

There are sunk costs, not just in money but in the years of process built around the existing way of doing things.

None of this is irrational.

That’s the hard part.

The person who sticks with the status quo isn’t making a bad decision, which means the typical founder response of “let me show you more features” or “here’s our ROI case study” doesn’t actually address what’s holding them back.

the fun stuff (before we jump into things…)

My boys have been sick this week, so not a ton of fun things are going on. We’ve been putting socks on for the younger one because he’s been cold at night.

what status quo actually looks like for our customers

When I say Journey competes against status quo, I don’t mean “the old way of doing things” in some abstract sense. I mean specific, named things.

For a CRE fund raising capital, the status quo is a BCC blast to 50 LPs with three attachments and a prayer. It’s a shared Google Drive folder that three people have named differently. It’s an email thread where someone has replied-all asking for the deck you sent two weeks ago. It “works.” Nobody’s been fired for it. It’s free.

For a manufacturing sales rep, the status quo is emailing spec sheets as PDFs. It’s forwarding the same product render for the fourth time. It’s having no idea whether the procurement manager ever opened the email or just let it die in their inbox. It “works.” The deal might close anyway.

This is the thing I keep underestimating: the status quo doesn’t feel broken to the people living inside it. It feels how it should.

the actual barrier isn’t awareness. it’s urgency.

I read something this week that named this clearly. The author called it temporal myopia — we make bad long-term decisions to preserve short-term comfort. The decision-maker who sticks with the status quo isn’t irrational. They’re weighing the very real cost of switching against a pain that’s dull and familiar rather than sharp and immediate.

There’s no urgency. The work is getting done. People know how to do it. And the moment you introduce something new, you’re also introducing a learning curve, change management, the possibility that it fails, and the reputational risk of being the person who championed a tool that nobody ended up using.

B2B buyers aren’t just buying software. They’re making a bet with their credibility. They recognize the pain. But recognition isn’t urgency. The copy describes a nuisance. It doesn’t make the nuisance bleed.

What’s the version of this pain that has a number attached to it?

That’s the thing worth writing about in an outreach message. Not the problem in general. The cost of the problem, specifically.

how this changes the experiment we’re running

This reframe has a direct impact on the Clay outreach we’re building for the manufacturing sprint.

The original approach: identify companies with complex product lines and a content-sharing gap, then send a message asking if they’d want to see how Journey helps.

The problem with that: it asks them to imagine a better future. But the status quo bias means they’ll default to “we’re fine.” We’re asking for mental effort from someone who has no urgency.

The new approach: don’t ask. Just show up with the value already delivered.

We have a Clay integration that auto-generates a personalized Journey URL from a template, so instead of a cold email asking whether they want a demo, the first message is the demo.

We build them a sample Journey using their public product content and send it.

We follow up with: “curious what you think of this compared to how you’re currently sharing this stuff.”

It feels simple. It feels too easy a change (and it might not make a material difference, but I do recognize that it’s a different psychological ask.

It’s not “here’s a thing that would help you” — it’s “here’s the thing, what do you think?” The status quo is suddenly sitting right next to an alternative, and the comparison does the selling.

still not easy

The status quo has a moat built out of familiarity and inertia. The only way to beat it isn’t to convince people it’s broken. It’s to make switching feel smaller than staying.

That’s what we’re trying to figure out how to do.

More soon.

Let’s keep it going.

Cheers, Danny

I got asked, “Is Journey a candy?”

I didn’t know what that was referring to. I knew what the painkiller vs. vitamin metaphor was, but I had never heard of the “candy” option.

I love candy, but it didn’t sound like a positive thing.

Anyways, so I decided to do some reading.

Sarah Tavel’s old post extends the painkiller vs. vitamin framework into a third category she calls “drugs.”

I’ve heard the painkiller/vitamin thing a hundred times, but re-reading it made me think Journey might be candy for most of the people using it right now.

Not for everyone. And not in a fatal way. But more often than I’d like to admit, I think people are using Journey because it’s delightful… not because they need it.

And if that’s true, it explains a lot.

the fun stuff (before we jump into things…)

I use a spreadsheet to run our family budget. I don’t like stuff to be connected to our bank accounts, but more importantly, I like the “manual entry” part of a spreadsheet because it holds my wife and me accountable a little bit.

Anyways, over the weekend, I started building a web app version in Replit. Finished it up last night, and I’m excited to boot it up and start using it (my wife is not).

the framework, quickly

Kevin Fong, a VC in the Bay Area, is credited with breaking business plans into three buckets:

“We divide business plans into three categories: candy, vitamins, and painkillers. We throw away the candy. We look at vitamins. We really like painkillers. We especially like addictive painkillers.”

Painkillers solve urgent, obvious pain. Customers don’t shop around; they just pay. Think Uber. Getting around SF was miserable until it wasn’t.

Vitamins are nice to have. People tell you, “I love this idea,” and then get on with their lives. A lot of SaaS graveyard residents here.

Candy is pleasurable and fun. People use it. They might even love it, but they can live without it. Clash of Clans made $1.5M a day. Candy can work, but it’s a completely different business than a painkiller.

Sarah Tavel adds a fourth: drugs. Like vitamins, drugs can’t harvest existing demand. But unlike vitamins, they become addictive.

Two things make a drug: accruing benefit (the more you use it, the better it gets) and mounting loss (the more you invest, the harder it is to leave).

so where does Journey.io actually sit?

Here’s my honest read.

Journey is a candy-vitamin hybrid, with occasional painkiller moments, and which one it is depends almost entirely on who’s using it.

For the AE who wants to impress a VP of Finance with a beautiful mutual action plan, Journey is candy with some vitamin qualities. They could send a Google Doc, but Journey looks incredible and makes them feel professional. They use it, enjoy it.

For the founder doing their own outbound, staring at an email they sent three days ago, wondering if anyone even opened it? There’s a real pain here. Their emails get ignored. They have no signal. Journey gives them intelligence and a professional presence they can’t manufacture otherwise. That’s closer to a painkiller, but not a drug (not addictive).

For the CRE fund managing 50+ investor relationships across a 6-month fundraise, drowning in reply-all threads and “can you resend that deck”? That’s painkiller territory. Genuine urgency. Real willingness to pay. We have a customer in this segment paying ~$500/month, and they are seeing value.

I’ll get to this in another newsletter, but after some initial tests, I’m finding that it’s not just as simple as “go find more of these and they will also get addicted”. There is nuance to it.

Overall, the problem is that I’ve been building and marketing to all three of these people at once.

where we fall short

We don’t make ourselves hard to leave.

This is the Sarah Tavel “drug” test, and we fail it (for now). There’s no meaningful accruing benefit or mounting loss in Journey today. You create a beautiful link, send it, the deal closes, or it doesn’t, and then you create another beautiful link. Your past Journeys don’t make future ones smarter. The product isn’t learning. Every rep who churns takes everything with them because there’s nothing they’ve built that they can’t rebuild in 20 minutes somewhere else.

I feel like I always sensed this, but it took me several times of going through this Medium post by Sarah Tavel to be able to put my observations into words.

our differentiation is mostly aesthetic.

Beautiful design is real value. It’s not nothing. But it’s not a moat. It’s a headstart someone closes in a couple of weeks.

we’re serving the wrong moment in the funnel.

Journey lives in late-stage sales: that’s where reps use it, where prospects interact with it, where we measure success, but I’m starting to believe the real pain is earlier. It’s in the first 48 hours after a discovery call when a prospect goes cold. It’s in the outbound touch that needs to stand out. That’s when people are most desperate for a signal. That’s when they’d pay anything to know if their prospect is actually interested because, without the initial signal, there really isn’t anything that follows.

This is where I’m starting to maybe start leading into something addictive.

Is there an addiction to value we can build where EVERY exchange of value via content, case studies, videos, PDFs, one-pagers, lead magnets, videos, demos, etc., for a prospect is ALWAYS housed in a beautifully designed Journey?

And does the product today enable such an experience to the users?

the hypotheses I’m actually testing

These are bets. Writing them down forces me to commit.

Hypothesis 1: the engagement data is the real product. we just haven’t built around it.

Right now, analytics are a feature. They should be the spine. Who opened it, how many times, which sections they lingered on, whether they forwarded it — that’s not a dashboard nicety. That’s the difference between a rep knowing they should follow up and knowing exactly what to say when they do.

Hypothesis 2: our ICP isn’t “sales reps”. it’s people who are in active, high-stakes communication cycles with groups of people they can’t afford to lose track of.

CRE funds raising capital. Founders in enterprise sales cycles. Manufacturers with complex products and long evaluation periods. The common thread isn’t industry or company size, it’s situation. They’re in an active communication mode where every missed signal costs real money. That’s the PQS lens I wrote about last week applied directly to our painkiller question. Who is in so much pain right now that they’d pay us to make it stop?

Hypothesis 3: we need a network effect or we’ll always be a feature.

Every Journey link that gets received is a top-of-funnel moment. Every prospect who clicks through and thinks “wait, what is this?” is a potential future user. But we don’t capitalize on it. If receiving a Journey became a reason to create one, we’d have an organic growth loop that compounds. We don’t have that today.

so what?

There’s a line from one of the readings I was going through this week that stuck: if you find yourself convincing the prospect that they have a problem you can solve, chances are you created your solution too early.

We have a product that genuinely solves something for somebody. I talk to those people. They light up. They refer friends without being asked. They use it every week without prompting. The work isn’t to make Journey better for everyone. It’s to find more of those people and then build so deeply around their pain that we stop being a nice-to-have for the masses and become a can’t-live-without-this for a few.

Stop selling candy.

Let’s keep it going.

Cheers, Danny

Last week, I sat down with Steven Brady and we defined who Journey.io is actually for.

If you’d asked me a couple months ago who Journey’s ideal customer was, I would have given you a confident answer.

Something like: “Teams that need to share complex information with stakeholders and want to track engagement.”

Useless.

That description could be a CRE fund sharing deal memos with investors, a manufacturing company sending spec sheets to procurement teams, or a solo founder pitching with a Google Drive link.

All technically true. All completely different buying motions, pain points, and willingness to pay.

The issue wasn’t that we didn’t have customers.

We do.

The issue was that I couldn’t articulate why those customers bought, what specific pain drove them to us, or how to find more people in that exact same situation.

That’s the gap. And if you’re a founder reading this and you can’t answer those three questions for your best customers, you have the same gap.

Here’s what I’ve learned, and what we’re now building.

fun stuff (before we jump into things…)

With the boys sharing a room, I moved my office from the guest bedroom to the extra room that we have now. Still a bit of organizing to do, but it’s nice to have a bit of room (although I’ve subconsciously walked into the other room at least a half dozen times already this week).

enter PQS and PVP

Reading through Jordan Crawford’s Blueprint GTM methodology (here’s a Substack that talks about this), I got introduced to two concepts that I think every early-stage founder needs to internalize:

Pain-Qualified Segments (PQS) — These aren’t just ICPs. A PQS is a specific situation a specific type of company is in that creates a pain your product solves. The key word is “situation.” It’s not about demographics (industry, size, revenue). It’s about what’s happening to them right now that makes your product relevant.

Permissionless Value Propositions (PVP) — This is the outreach angle that proves you understand their pain before you ever ask for a meeting. A good PVP uses publicly available data to deliver an insight the prospect hasn’t connected themselves. It passes what I now call the “Holy Shit, that’s useful” test — from their perspective, not yours.

If you can’t define your PQS and build PVPs against them, it means you don’t deeply understand the value of your own product. Not in the way that matters for growth. You might understand it technically. You might have a nice features page. But you don’t understand it from the buyer’s chair — which is the only place that counts.

Here’s an example of a PQS and PVP:

PQS #1: “New Fund Raising Capital Without a Communication System”

Ideal Customer Profile Experiencing Pain

Company: CRE fund or alternative investment firm, 2–15 employees, actively raising or deploying capital Persona: Founder / Managing Partner / VP of Investments Situation: Running a fund that communicates with 30–100+ investors per deal. Currently sending deal memos, webinar recordings, and quarterly updates via email attachments or shared drives. Every deal cycle means rebuilding the same email thread chaos from scratch.

Core Pain:

• Sending 50–60 investors the same deal materials via individual emails or BCC blasts

• No visibility into which investors actually opened/read the materials vs. ignored them

• Investors reply-all or email back asking for documents already sent 3 weeks ago

• 6+ month fundraising cycles with no single source of truth — just scattered email threads

• Can’t tier investor interest (who’s hot, who’s cold) based on engagement

• Sharing sensitive financial documents via email attachments feels unprofessional and insecure

Pain Data Recipe

Data Point Source Timing Signal Fund currently raising capital (open fund or new vehicle) SEC EDGAR filings (Form D), AngelList, fund announcements Active raise or within last 90 days Using Dropbox/Box/Google Drive for investor documents Website tech stack (BuiltWith), job postings mentioning tools Current Investor base of 30+ LPs Fund size + minimum check size math, LinkedIn network Current NOT using Juniper Square or similar investor portal Website tech stack, job postings, G2 reviews Current (absence of signal) Small team (2–15 people) LinkedIn Company Page headcount Current

Why This Segment Matters to Journey Now

These funds are in active communication mode — they MUST get materials in front of investors consistently and professionally. Every missed open or buried attachment could mean a $25K–$150K+ check that doesn’t get written. Journey’s tracking turns investor communication from a black box into a tiered pipeline. We have a customer in this segment paying $500ish/month so it’s proof this segment pays premium and stays long-term.

Example PQS Message Hook

[Mirror] Noticed [Fund Name] is raising Fund II — congrats on the momentum. With 40+ investors to keep updated across a 6-month cycle, I’m guessing your inbox is becoming the de facto deal room right now.

[Insight] The investment firms we work with that manage 50+ investor relationships found that the biggest leak in their fundraise wasn’t deal quality — it was communication visibility. They had no way to know which LPs actually read the deal memo vs. which ones let it sit in their inbox. The ones who closed faster started using a single evolving link per deal instead of email threads — it let them tier investor interest by engagement and follow up with the right people at the right time.

[Ask] Curious how you’re currently tracking which investors are actively engaging with your materials vs. going quiet?

PVP 1.1: “Your Form D Says You’re Raising — Here’s Who’s Reading Your Materials”

Rating: Gold Standard

Target Persona: Managing Partner / Founder of CRE fund Core Insight: SEC EDGAR Form D filings are public. When a fund files a Form D (Regulation D exemption), the raise amount, date, and executive names are on record. Cross-reference this with whether the fund has any investor-facing content platform (BuiltWith scan) and you can identify funds actively raising capital with no engagement visibility system. Data Basis: SEC EDGAR Form D filings + BuiltWith tech stack scan + LinkedIn headcount Value Proposition: “You filed your Form D 6 weeks ago for a $15M raise. Based on your web stack, you’re managing investor communications through email. Here’s what that looks like from the investor’s side — and what the funds closing faster are doing differently.” Low-Effort CTA: “Want me to build a sample investor Journey using your fund’s public materials so you can see the difference? Takes 10 minutes to set up, zero from you.”

what this can look like in practice

We mapped Journey’s market into three ICPs: Commercial Real Estate / Finance, Manufacturing / Industrial Products, and Founder-Led B2B Services.

Within each, we defined Pain-Qualified Segments — not just “who they are” but “what’s happening to them right now.”

For CRE funds, one of our PQS targets is: “New fund raising capital without a communication system.” That’s a fund with 30–100+ investors, actively raising, currently managing deal memos and quarterly updates via email attachments and shared drives. Every deal cycle, they rebuild the same email chaos from scratch. They can’t tell which investors actually read the deal memo vs. which ones let it sit in their inbox.

The timing signal? SEC EDGAR Form D filings. When a fund files, the raise amount, date, and exec names are public record. Cross-reference that with a BuiltWith scan showing no investor portal, and you’ve identified a fund in active pain with no system.

For manufacturing companies, one of our segments is: “Complex product, can’t demo on Zoom.” These are companies with 7+ product lines, 40+ spec sheets, beautiful renderings on their website — but the moment a sales rep needs to share materials with a prospect, it all becomes email attachments. They’ve got HubSpot but no content platform between marketing and sales.

The data recipe here is scraping product pages, counting downloadable assets, checking the tech stack for sales enablement tools (Highspot, Seismic, Showpad), and confirming the gap.

For founder-led services, we’re looking at founders sharing portfolio work via Google Drive links on LinkedIn. The PVP here is almost absurdly direct: take their public work, rebuild it as a Journey with proper visual presentation, and send them the before/after. Their prospect currently sees “ClientX_Reel_Final_v2.mp4.” We show them what it could look like instead.

the humbling part

The thing that really hit me during this process was realizing how much of our positioning was so generic.

That’s the difference between “Journey helps you track engagement on shared content” and “Your last webinar had 75 registrants. The recording on YouTube has 23 views. That means roughly 52 investors who were interested enough to register never watched. And you have no idea which 52.”

The first is a feature statement. The second is a PVP.

One gets ignored. The other gets a reply.

Our highest-paying customer, who’s in the CRE segment, didn’t come to us because of a cold email about features. They started using Journey for webinars and community content, then expanded to all investor communications. They now power every LP touchpoint through Journey. That journey (no pun intended) from entry point to full adoption is the exact path we need to engineer for new customers and the PQS/PVP framework gives us the map.

will it work is my question

I don’t know, but this is all a forcing function because if it doesn’t work it just means that Journey is just noise and another generic SaaS tool without a specific corner of the market.

If you’re a founder still operating with a vague ICP and sending generic outreach, I’d encourage you to do the exercise we just did. Ask yourself: for your three best customers, what specific situation were they in when they bought? What was happening in their business that made your product urgent? And can you find more people in that exact same situation using publicly available data?

If you can’t answer those questions, you don’t have a targeting problem. You have an understanding problem, a positioning problem. And no amount of volume is going to fix it.

That’s what I’m working towards…

Cheers,

Danny

It was both a sigh of relief and a bit of panic because it made me feel somewhat “seen”. I’m not some savvy veteran who’s gone through it all with SaaS entrepreneurship, but I do believe I’ve been smacked in the face enough times to know what pain feels like and to know what resiliency requires.

So when I read this, it felt good to know that I’m not alone… and it took me a bit of time to get over some of my anxiety and find hope.

fun stuff (before we jump into things…)

My eldest is 4. He’s pretty awesome at drawing. I love that he can sit and do this for an extended period of time. Shout-out to my dad who’s the best artist I know for feeding my son’s passion (because I’m trash at drawing).

quick tl;dr on what I read

Again, credit all goes to Topline (none of this is uniquely mine).

Over 80% of public SaaS companies are trading below their 2021 prices.

And here’s big one: the cost to generate a dollar of net new ARR has nearly doubled…from $1.24 to $2.23.

Growth has collapsed.

Median ARR growth for public SaaS companies has cratered from 34% in late 2021 to just 15% in early 2026. There are fundamental shifts in how buyers evaluate and purchase software.

GTM efficiency is in freefall.

While companies have gotten better at profitability (FCF margins up from 0% to 20%), they’ve done it by cutting costs, not by getting better at selling. The underlying economics of customer acquisition have deteriorated badly.

The horizontal play is dead.

Companies trying to be everything to everyone are getting crushed. The winners? Vertical SaaS companies that maintained stable growth and actually improved their GTM efficiency after 2023.

This is the world we’re operating in.

So the whole thing isn’t all bad… there are glimmers of hope towards the end, and here’s how I’m applying it.

the clarity problem

Journey is a horizontal product (not good for us based on the numbers above).

You can use it for sales enablement, customer onboarding, investor relations, event marketing, and recruiting. And that was the problem.

High traffic. Terrible conversion. Customers who used it heavily churned anyway because when you’re everything to everyone, you’re nothing to anyone.

The data from “Beneath the Benchmarks” confirms this:

Vertical SaaS companies are the ones maintaining growth and improving efficiency. They know exactly who they serve and why those customers can’t live without them.

This isn’t new, but it feels “new” for some reason.

Maybe it’s because of how big the world of PLG was. Maybe it’s because I came out of the micro-SaaS world where I bought and sold 9+ single purpose applications selling to anyone and everyone.

I don’t know, but I need to stop trying to sell “Journey” and started selling solutions to specific, painful problems.

the mechanisms for winning

I shared my last post some of the initial discovery that I started to do with a GTM buddy (more on this next week).

I won’t go through the segments that we are testing to hone in on a more vertical approach, but instead want to share a couple of ways I’m rejigging my founder brain

1. Obsessing Over Retention Leading Indicators

The Science of Scaling (referred to this in the last post as well) is clear: PMF isn’t about revenue growth. It’s about whether your customer retention leading indicator correlates with long-term retention.

For Journey, I need to understand what indicators predict retention.

I thought I knew. The previous founders thought they knew. But I don’t think we knew the right answers.

One issue I’m currently facing is that my existing trial sign-ups are no good… meaning that if I used them to develop my indicators, I would be walking along the wrong path because they are not the customers I need.

Therefore, I’m hoping this new GTM approach will help proactively get me in front of the right folks and setup accounts for the right segments.

PS - I’m tempted to get rid of my free trial self-service workflow and require a form/a conversation/a validation step before getting access to a guided, free trial.

Let me know your thoughts on this…

2. Pain-qualified segments

With Steve’s help, we’re building hyper-specific segments:

• CRE funds using an investor portal and actively fundraising (we can see this from their website)

• Manufacturing companies with complex products and 5+ person sales teams

• B2B service founders who are active on LinkedIn

Then we’re crafting messages that make them think: “How does Danny know exactly what I’m dealing with?”

3. “Done-for-you”

When someone signs up for a trial and fits our ICP, I offer to build them a Journey using their actual marketing assets. I scrape their website. I find their case studies. I show them what it could look like.

This doesn’t scale, but it’s okay.

I’m in Stage 1 (PMF), not Stage 2 (GTM Fit).

The Science of Scaling framework is explicit: at this stage, your GTM playbook is “Win At All Cost.” Win means getting customers to their retention leading indicators.

the opportunity

Here’s the thing about what I’m working everyday to embrace: tough times force clarity.

When money was free and growth was easy, you could get away with horizontal positioning and mediocre retention.

Not anymore.

The companies that survive this will be the ones that know exactly who they serve, why those customers can’t live without them, and how to acquire them efficiently.

I’m not there yet with Journey, but I’m closer than I was four months ago.

And in a market where 80% of public SaaS companies are underwater, I’ll take progress over perfection any day.

Crawl, walk, run

Do the right things in the right order.

Stage 1 is about customer success.

Stage 2 is about scalable acquisition.

Stage 3 is about growth and moat.

That’s it for this one. Let’s keep it going.

Cheers,

Danny

The growth playbook I used to buy, operate, and sell 10 other SaaS businesses since 2021 is effectively obsolete.

As we navigate the path to Product-Market Fit (PMF) with Journey, I’ve had to confront the fact that what worked for B2B SaaS three years ago is now a recipe for stagnation.

Here is what I’m learning about the “New Playbook” and how our strategy is evolving in real-time.

fun stuff (before we jump into things…)

It’s been mayhem here at the Chu residence since last Friday when we got some rough weather here in Texas.

My 2 boys have been home from school since Monday, so they’ve been watching a lot of TV, fighting a lot, but also enjoying each other more than ever.

They are great, and my wife and I love seeing them grow up.

the volume trap vs. the efficiency reality

For a long time, the standard SaaS playbook was a “numbers game”: pump the top of the funnel with high-volume outbound, prioritize MQLs (Marketing Qualified Leads), and grind to close deals.

Why it’s broken now: In the current market, the “Volume Play” has hit a wall of diminishing returns. With the explosion of AI-generated outreach, buyers are drowning in noise. Research shows that the average B2B buyer is now 70–80% through their journey before they ever want to talk to a salesperson.

If your playbook relies on “booking the demo” to explain your value, you’ve already lost. We’ve realized that growth isn’t about how many people we message; it’s about the intent signal of the person who is struggling to manage a high-stakes narrative.

The struggle here is to identify what the intent signals are, how to actually track them effectively, and do something about it with the right message, at the right time, with the right people.

why “candy” SaaS isn’t so sweet anymore

During our session, Steve used a great analogy: “Candy” vs. “Complex.”

“Candy” software is simple, transactional, and low-stakes. You don’t need a manual to buy it. But the SaaS market is currently oversaturated with “Candy”, tools that provide minor convenience but no mission-critical ROI.

PLG used to sort of be a default for “candy” software because it wouldn’t make sense to sell a low ACV software product with expensive salespeople, but now you see Enterprise software execute a PLG motion and some of these lower priced products run consultative sales processes.

So what does that mean for Journey?

Our best customers are surprisingly in rather complex industries like Commercial Real Estate and Manufacturing. As a result, they aren’t looking for a tool; they are looking for Asynchronous Education.

When you are selling a multi-million dollar real estate fund or a 50,000lb industrial machine, you aren’t looking for a “quick transaction.” You need to educate a dozen people who are never in the same room.

“Candy” doesn’t solve that; a structured narrative does.

So how do we sell a low ACV product that looks like “candy” but needs to be perceived as a vibrant, complex creme brûlée lol.

build software to solve actual human problems

The old way to grow was to look at a competitor’s feature list and try to build a “better” version. We call this “Feature Parity Growth,” and it’s a race to the bottom.

We’ve realized that Journey’s growth doesn’t come from being a “better file sharer.”

It comes from solving a fundamental human stressor: Information Clutter.

In today’s software ecosystem, “Tool Fatigue” is real. The average enterprise uses over 100 SaaS apps. Most buyers don’t want a new tool to learn; they want their current problems to disappear.

When we ask, “Are you drowning your clients in PDFs?” we aren’t selling a feature. We are addressing a breakdown in human communication. By focusing on the problem (the mess) rather than the tool (the storage), we bypass the “budget fight” and move straight to the “value fight.”

I’m good at this on a sales call, where I can meet someone face to face and have a human to human interaction.

What’s hard and the “nut to crack”?

How do you communicate this same level of value asynchronously, on LinkedIn, on your website, with less than 5 words on your H1, with your blog content, and with your “product” without just being “another” digital sales room…

This is where it feels like the companies we see thriving have found their “secret sauce”.

The ability to resonate with actual human emotions.

“horizontal” mirage

When we bought Journey, it felt as broad as Google Slides.

There is a massive temptation in SaaS to build a “horizontal” tool, something for everyone. The logic is that a bigger TAM (Total Addressable Market) equals a bigger company.

Unfortunately, horizontal tools are becoming commodities. If you try to speak to everyone, your messaging becomes so diluted that you end up speaking to no one.

Vertical-specific growth almost feels like the only real opportunity to build a successful SaaS.

We are moving away from being a “sharing tool for anyone” to being a high-stakes communication platform.

• In Finance, a lost attachment or an unread memo can cost a six-figure investment check.

• In Manufacturing, a missing safety spec can halt a production line.

By narrowing our focus to these “high-stakes” verticals, we can build specific workflows that a horizontal tool like Google Drive or DocSend simply can’t touch.

the takeaway

The path to PMF isn’t a straight line. It’s a series of messy, sometimes uncomfortable realizations.

I’m learning that the real work is having enough self-awareness and then the courage to adjust the playbook even when it feels counter-intuitive to “shrink” your focus.

Have you noticed your “standard” playbook starting to crack lately? I’d love to hear your thoughts.

That’s it for this one. Let’s keep it going.

Cheers,

Danny

Last week, someone shared the available snippet from Mark Roberge’s “The Science of Scaling”, and it gave me a chance to reflect on not the “what” or “how” I’m building, but “why”.

what i learned

Reading Roberge’s work matured my understanding of four principles:

1. Customer Retention Comes Before Revenue Growth

Everyone says “triple, triple, double, double.” But that’s how you end up as a cautionary tale.

At Journey, we were hiring aggressively, building features fast, and chasing every lead. Meanwhile, customers were churning silently because we hadn’t nailed what made them successful.

Now we’re exploring how we might monitor and analyze a specific leading indicator: 70% of customers spending 3+ minutes exploring a journey and sharing it with their team within 60 days. This correlates with long-term retention. Then it should be our north star.

2. Product-Market Fit Needs a Number, Not a Feeling

“We have PMF” is usually a guess. I know because I made that guess.

The framework is simple: Pick a percentage (60-80%), an event (something customers do that creates value), and a timeframe (1-3 months). Then measure it obsessively.

For us: 70% of customers + 3+ min exploration + sharing + 60 days = PMF signal.

For Slack, it was 70% of customers sending 2,000+ messages in 30 days. For Dropbox, 85% uploading 1 file in 1 folder within 1 hour.

The specificity matters. It forces clarity.

3. Do Things That Don’t Scale, Longer Than You Think

This one changed my mindset completely.

We were obsessed with building scalable processes. Automated onboarding sequences. Self-serve flows. Templated everything.

But we hadn’t actually figured out what drives retention yet. So we were scaling the wrong thing.

We are taking a step back to get some more data points on this.

Once we nail that, then we build scalable processes around it. Not before.

what i’m trying to do differently

Based on all of this, here’s how I’m applying it to different parts at Journey:

1. Retention-First Roadmap We’re reorganizing our entire roadmap around that 70% leading indicator. Every feature, every improvement, every decision gets filtered through: “Does this help customers hit our success metric?”

2. Doubling Down on “Unscalable” Work I’m personally doing customer onboarding calls. Our product team is doing weekly check-ins with customers. We’re learning what actually drives value before we automate it away.

3. Messaging Clarity Over Feature Parity We’re not building 10 new features this quarter. We’re getting crystal clear on our positioning, testing it with intent, and making sure every customer we acquire is someone we can actually help.

for my friends

Here are questions I’m asking myself (that might be helpful for you, too):

• What’s your customer retention leading indicator? (If you don’t have one, that’s your first project.)

• Are you optimizing the right thing, or just making the wrong thing more efficient?

• Are you still doing the unscalable work that teaches you what actually drives value?

The founders who win aren’t the ones who grow fastest. They’re the ones who grow sustainably, with customers who stick around.

That’s what I’m working towards…

Cheers,

Danny

ps - if you want to read the “Science of Scaling”, you can find it at stage2.capital/science-of-scaling.

The business was a consequence of a “Frankenstein of product-market fit.”

I thought the problem was optimization.

It wasn’t.

fun stuff (before we jump into things…)

I’ll save you a picture this time, but my 2-year old did “his business” on the little plastic toilet we have setup in the bathroom for the first time yesterday. He was so happy. His older brother was so happy for him, who was also doing “his business” on the regular toilet next to him.

Life is so fun with community. Even the small things, even the most uneventful things, can be memorable.

Same thing with building a business. It’s freaking lonely, especially when it’s not going well, so just putting yourself in a position to be around community, be around those that can give you energy and give you hope, are big factors to “winning” (imo).

traffic isn’t validation

Here’s some data around our previous website (we just launched our new one yesterday, 1/7/2026:

84% of our traffic was direct.

85% were new users.

They stayed for 8 seconds.

We were getting 400ish signups, but the conversion rate was abysmal.

My assumption was that the traffic is just unqualified.

The traffic is a Frankenstein. And I’m making decisions based on it.

The website reflected the years of pivots, unclear positioning, and horizontal product thinking had created a magnet for the wrong people.

Students with .edu emails looking for presentation tools. International users. People who had no business being there because we weren’t going to be the best fit for their needs.

The lesson: High traffic + low conversion means you need better targeting. My question was then how to stop trying to convert everyone and start attracting someone.

the positioning framework

Gab and I went through this exercise:

Use Case-Based Positioning

Instead of trying to be everything to everyone, he suggested narrowing it down to a specific use case.

For example,

“Following up after a sales call by sending a personalized, trackable package of content to re-engage buying committees asynchronously.”

This wasn’t about digital sales rooms. It was about asynchronous sales storytelling — helping sales teams tell a coherent story when they can’t be in the room.

The Messaging

We tested two variants:

Variant A: Onboarding-focused messaging
Variant B: Sales-led messaging

The results were stark:

• 80% higher response rate with sales messaging

• 56% of qualified prospects were explicitly seeking a sales engagement solution

• Sales messaging won on cold outbound, LinkedIn, and direct response

This wasn’t a close call. The market was telling us something clear: people want this for sales, not for onboarding.

The experiment was one of many that we had on our list.

I’ll share more about this later, but we eventually realized that there needed to be even further narrowing beyond just use cases, so that’s where I am today (will write more about that soon).

what the struggles taught me through this

1. Churn Without Clarity

We had customers using Journey really well — thousands of views daily — and then they’d churn. No explanation. No pattern.

This taught me that horizontal products are hard to understand. When something can be used for anything, it’s hard to know why someone stops using it. We needed to get vertical.

2. The Traffic Trap

I was obsessed with homepage optimization. Gab pushed back: “You have 1.54 pages visited per session. You want 2.5. But you can’t get there by tweaking headlines.”

We ran an A/B test on the homepage. The new positioning increased outbound clicks from 0.08% to 8.52% — a 100x improvement. Same traffic volume. Different message.

The lesson: Messaging moves the needle more than optimization. Optimization of a “wrong” = “more wrong”.

3. My Incorrect Assumptions

I believed:

✗ More traffic = more opportunity

✗ Optimization = conversion

✗ Horizontal positioning = broader appeal

✗ Product quality alone = market fit

All wrong.

the real problem (and a qualified solution)

By the back half of 2025, I realized something crucial:

The amount of traffic we get and how unqualified that traffic is means we can’t just optimize our way out of this.

And by the way, let me clarify to say what I’ve been meaning by “optimization”.

Optimization is what you do when you know which direction to go. A mentor used to always remind me that start-ups die because they start scaling too fast and end up scaling the problem (and not the value).

The way we get out of this is by finding message-market fit.

We need to:

1. Stop attracting the wrong people — This means positioning so clearly that unqualified prospects self-select out

2. Get in front of the right conversations — Not just wait for people to find us

3. Build a long-term positioning bet — This isn’t a 3-month play. It’s years (or many, many months) of consistent messaging.

4. Test with intent — Use our traffic advantage to validate messaging, not just tweak copy

But here’s the thing: None of this matters if we don’t get in front of more qualified conversations.

The traffic we have is a liability if it’s the wrong traffic. So we’re shifting from “how do we convert more of what we have” to “how do we attract what we actually want.”

the takeaway

The real work isn’t optimization, it’s clarity. It’s knowing exactly who we’re for, why they need us, and how to reach them.

The traffic will follow. But only if we know who we’re trying to attract.

What I’m learning: Sometimes the best marketing advice isn’t “do more of what’s working.” It’s “stop doing what’s not working, even if it looks like it is.”

This is the work of the next quarter. Get in front of more conversations. Get clearer on positioning. Test with conviction. And stop mistaking traffic for traction.

That’s it for this one. Let’s keep it going.

Cheers,

Danny

I’m starting this newsletter to share what I’m learning as I work toward product-market fit for Journey.io. If you’ve followed XO’s journey, you know I’ve had some small wins over the last 5 years, but this one’s different. And I think the lessons I’m learning right now are worth sharing (honestly, to hold me accountable).

Fun stuff (before we jump into things…)

I’ll always try to share something personal because I care about that stuff as much as I do about start-ups, building, etc.

2025 was a struggle personally and professionally (you’ll find out more below).

Being a dad is so hard… harder than being a start-up founder or entrepreneur or even a husband.

My two boys are 4 and 2 now… and whenever I get a chance at night to reflect, I break down because I have no clue if I’m doing this right haha. I thought I would be used to that feeling having been around start-ups for so long, but it feels different.

One reflection is just how important it is that I’M.. ME… is in the best state possible because my state of being moves throughout the life of my 2 boys.

Scary, but beautiful.

Concerning, but hopeful.

Unsure, but motivating.

Overwhelming, but thankful.

ps - let me know if you think this section should go at the beginning or end.

2025: The Year I Learned That Effort Doesn’t Equal Results

Let me be direct: I worked harder in 2025 than I ever have. And I failed more than I won.

Not because I didn’t put in the work. Because I put in work without consistency.

I got 100-150 end-of-year deal emails from tools I tested or trialed. Each one was something I was genuinely excited about at the time. Each one represented a project or task I started but didn’t follow through on. I’d jump in, get momentum, then disappear for weeks. Then jump back in. Then disappear again.

Here’s what I realized: Effort without consistency doesn’t compound.

I can work 80-hour weeks and still lose ground if I’m not showing up to the same things repeatedly. Consistency beats intensity every time.

My kids missed almost two months of gym and jujitsu at the end of 2025 because of holidays, travel, and illness. When they went back, they had to relearn what they already knew. Turns out the same pattern holds true for me.

My Current Focus with Journey.io (And Why It Matters)

With the two Y-Combinator companies I flipped for 2x+ returns in under 18 months, we knew exactly who we were talking to. The messaging felt clear because the pain was specific.

With Journey.io, I’ve been struggling.

We’re getting 350 free trial signups per month. But they’re the wrong audience. Which means I’m saying the wrong things. I’m solving the same problem for completely different people. And when you don’t know who you’re speaking to, finding your voice is nearly impossible.

That’s the real blocker right now. Not the product. Not the market. The messaging.

What I’m Learning About Messaging

I spent an hour with copywriter Justin Blackman in December, and it shifted how I think about this. Here’s what stuck:

Show, don’t tell. Justin watched my product demo and said, “That’s what hooked me. Reading about it, I had no idea what you do.” My demo video is doing more work than my headline. Your demo might be more important than your copy. Record yourself explaining your product to a friend. Note when their eyes light up. That’s your hook.

Find the hidden motivator. We kept circling back to “convenience” and “making someone’s life 1% easier.” But the real driver? “It makes you look like you actually care about the human on the other side.” That’s emotional, not rational. Ask your best customers why they really chose you. The answer is rarely what you think.

Simplify your language. “A simple page for sharing assets” beats “A microsite for collaborative content management” every time. I’m verbose by nature, so this is something I’m actively working on. Simple always wins.

Position against the familiar. “The Google Drive alternative that actually looks good” or “For when you’re ready to graduate from attachments.” Don’t explain what you are. Explain what you replace. People understand new things through comparison.

Just launched the new website today… www.journey.io if you want to check it out.

My 2026 Focus: Consistency + Clarity

So here’s what I’m doing differently in 2026:

For Journey.io specifically, that means:

• Testing simple language across different customer segments

• Talking to all different types of people using Journey to find where I could actually land

• Staying consistent with that process instead of jumping to the next shiny thing

I think this is going to work because the problem is solvable. It’s not a product problem. It’s a clarity problem. And clarity comes from consistency — showing up to the same conversations, the same messaging tests, the same customer interviews, over and over.

What About You?

What’s one thing you want to show up for consistently in 2026? And if you’re working on messaging or PMF, what’s your biggest challenge right now?

Let me know.

Excited to get back to writing and excited to stay connected with those who find this helpful.

That’s it for this one. Let’s keep it going.

Cheers,

Danny