on a journey to PMF: lessons from 2025 and what's next

Quick first post on a newsletter that is more of an accountability partner for myself

Hi friends,

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