Why you're getting this: At one point, you signed up for my newsletter over the last 12 years. I'm getting back into sharing my thoughts weekly on the state of B2B. These are things that I wrestle with on a daily basis, distilled and shared with other B2B founders. I hope you find them useful..
Before I get into this one, I need to say something up front.
I'm a little embarrassed to even write this newsletter. The stories I'm about to tell you are going to sound like a flex. They're not. I'm sharing them because the lesson underneath them is the single most important thing I've learned in 20 years of building companies, and if I don't tell the actual stories, the lesson won't land.
So if it reads like I'm trying to flex, I promise that's not the intent. I'm trying to save you from a mistake I see founders making every single week.
Alex starting Groove 15 years ago
Last week I wrote about SaaStr. 120+ demos, $30K-$50K ACVs, the panda incident, all of it.
What I didn't talk about was the thing that actually made it work.
It wasn't the booth. It wasn't the protesters. It wasn't even the offer.
It was the 14 years of writing I'd already done before I ever set foot in the Moscone Center.
Most people in my world don't know how Groove actually got off the ground.
When I started it in 2011, I had no money for ads. No connections in B2B SaaS. No name recognition. Nothing. I was a first-time founder going up against Zendesk, who already owned the category.
So I started writing. The "Journey to $100K MRR" blog. Then the newsletter. Then more posts. Year after year after year. Most of those early posts got 12 visitors. I'd spend 8 hours writing something and almost nobody would read it. I almost quit a dozen times.
The original 100K blog series circa 2011
But I kept going.
And that blog is the entire reason I'm still in business today.
We scaled Groove to $5M ARR bootstrapped, serving 2,000+ companies, with zero paid acquisition. Every single customer came from someone reading something I wrote, or someone who knew someone who did. That same audience is what made the Helply launch possible 14 years later.
I didn't start with a marketing budget. I had a keyboard and a willingness to write honestly about hard things, week after week, for over a decade. Today I can drop $100K on a single conference booth without flinching, but back then the blog was all I had, and it was enough to build a real business on.
That's the only reason any of this exists. Not the SaaStr booth. Not Helply. Not the panda. The blog came first, and everything else was built on top of it.
Now back to SaaStr.
Last day of the conference. I'm walking up to get a margarita at the happy hour. Some guy stops me.
"Dude, Alex."
"Yeah, what's up?"
"Bro, I've been reading your content for the last 15 years. You saved me, like, multiple times. I used to read your 100K content religiously every day."
I honestly didn't know what to say. I'd been getting emails from readers for years and always knew the content was hitting, but having a stranger walk up to me in person and tell me it helped him through some of the hardest parts of his career was a different thing entirely. I just thanked him. We talked for a few minutes about where he was at, what he was building, what he was struggling with.
It turned out he ran support at a B2B SaaS company. Right in our ICP. He asked if he could see Helply. I said yes.
This is the part I'm embarrassed to write, but I have to. That wasn't a one-off. It happened over and over the whole conference. People walking up to the booth asking if Alex was around. People wanting pictures. Someone literally referring to me as "the LinkedIn influencer" at the bar. One guy who'd been reading the Groove blog since 2012.
I'm sitting there at the booth thinking, what the hell is happening?
What's happening is this. The same asset that built Groove to $5M ARR is now building Helply's pipeline. The audience kept reading. The trust kept compounding. And 14 years later, that same audience is showing up to take demos for a brand new product.
That's a completely different sales motion than a cold booth at a conference. It's not even the same game.
The founders I see who are crushing it right now are the ones who started writing five, ten, fifteen years ago and just never stopped. Greg Eisenberg. Adam Robinson. A handful of others. They built the asset before they needed it.
The founders who are about to get cooked are the ones who looked around, saw what's coming with AI, and only now realized they need a personal brand. They're 18 to 24 months behind the eight ball and there's no shortcut.
There's a reason I felt comfortable spending $100K on a single conference. There's a reason I felt comfortable bringing 16 protesters and an 8ft panda and Hawaiian shirts. There's a reason I felt comfortable going on the offensive against incumbents.
It's because the downside was capped.
If the booth had been a complete disaster and we'd booked zero demos, I would have lost $100K. Painful, but not fatal. And I still would have had the newsletter. Still would have had ~50K subscribers and ~63K LinkedIn followers. Still would have been able to launch Helply to a warm audience the next week.
The asset doesn't go away just because one campaign flops. That's the same reason Groove survived a dozen near-death moments over 12 years. When everything else was on fire, the blog was still bringing in customers.
Without an audience, every bet is existential. With one, I can take asymmetric shots all day long, because I built the safety net before I needed it.
If you're a founder building right now and you don't have an audience, my advice is to start writing on LinkedIn today. Not when the product is ready. Not when you've raised a round. Today.
It will feel pointless for the first 6 to 12 months. You'll write posts that get 4 likes. You'll send newsletters that get opened by your mom. You'll wonder why you're spending hours a week on something that has no measurable ROI.
I felt all of that in 2011 and 2012. The ROI doesn't show up in month one. Or month six. Or sometimes even year one. It shows up in year three when your blog starts driving real signups, in year five when you cross $1M ARR without spending a dollar on ads, and in year fourteen when a guy walks up to you in the margarita line at SaaStr and books a $40K demo because he's been reading you since he was 22.
And it matters more now than it ever has. AI is making cold outbound borderline useless. Every founder's inbox is being filled with AI-written cold emails right now. Every LinkedIn DM is getting more spammy. Every channel is being saturated. The only thing that cuts through is being someone people already want to hear from before you reach out.
That takes years to build. There's no shortcut.
If you're a founder reading this and you haven't started, you're not behind because you didn't go viral last week. You're behind because the founder you're competing with started writing in 2011. The only fix is to start today and keep going.
I'll keep writing about what I'm seeing on the ground at Helply. The good, the bad, the embarrassing parts.
That's the deal.
Alex Turnbull
Founder of Helply
The first AI-Native Help Desk built for B2B
P.S. If you're a B2B SaaS company $1M-$50M ARR currently on Zendesk and feeling the seat pricing squeeze, I'd love to show you what we're building. Book a demo here.
P.P.S. The guy in the margarita line? We're talking next week. Honestly, the conversation meant more to me than the demo did.