Today, I am going to reveal the exact playbook I used to scale Triple Whale to the moon.

But the real story starts with four slides.

Before our Series A, I got to see the investor diligence deck. There were four slides about how Triple Whale had built a cult following.

Not four slides on the product. Not four slides on TAM expansion, pipeline velocity or whatever other nouns live inside VC decks.

Four slides on the cult. A cult following for B2B SaaS analytics software!?!

That sentence still makes me smile because it proved something I believe deeply:

There are no boring categories. Only boring operators.

But before the whale, some background for those who are new here.

I went to school wanting to be an investment banker. Then didn’t. Graduated with an economics degree from IU in 2008, which was a truly exquisite time to enter the financial system (great vibes, zero issues, everyone having a normal one).

And I had no clue what I was going to do.

I was lost in my twenties the way ambitious people often are. Not lazy. Not exactly aimless. Just aimed wrong with way too much energy and no good place to spend it.I tried everything. Web development. Photography. Funnel builds. Agency gigs. Paid media. Random side quests online.

Ran ads for Oprah once. Worked at Whole Foods running paid media for the recruitment vertical. Started an agency. Got weirdly hooked on Google Data Studio, Supermetrics and that quick hit from dashboards that actually showed the health of a business.

Then digital marketing sort of found me. Or I found it. Triple Whale showed up eventually. I noticed them early on Twitter, scrappy and interesting, basically turning the spreadsheet pain every ecommerce person knew into a real product. We started bantering on the bird app. One thing led to another. AJ slid into my DMs asking if I wanted to consult.

Sure, why not? Famous last words. Consulting grew into something bigger. Bigger became CMO. Suddenly I was inside one of the fastest companies I had ever seen.

When I joined, Triple Whale was tiny, scrappy, chaotic and wonderful.

For a stretch, I was the whole marketing department. Running paid media. Writing the newsletter. Hosting the podcast. Taking sales calls. Living in Calendly like it was haunted (jk, we were too poor to afford Calendly at the time).

I was doing way too much. Proper lunatic mode engaged. Insane. But also one of the best stretches of my career.

This is the story of the playbook we ran. What worked. What didn’t. What I would change. What I am proud of. What I regret. Which parts still matter if you are trying to build something fast today.

The whole thing boiled down to four pillars:

Community
Content
Education
Moonshot marketing

Hiring was the fifth, but hiring is not a pillar. Hiring is the whole building.

Everyone claims they want a community. Most do not. They want a distribution channel they can push feelings into. They want a Slack they can sell into now and then. They want a Discord with a logo. They want engagement, user content, a cheaper way to get noticed. That is not community. 

A real community lives on its own. It has inside jokes, rituals, status games, unofficial leaders, people who show up even when you are not around. Triple Whale had that. Our community was called Narwhal Nation. Yes, everything was whale themed. No, I will not apologize. 

Narwhal Nation turned into one of the strongest parts of the business, thousands of operators, marketers, founders and ecommerce sickos hanging out, swapping ideas, helping each other, talking attribution, creative, Meta, Google, retention, inventory, agencies, offers, everything. 

It worked not because of the clever name (but the name does bang). It worked because Kevin ran it. Kevin was my first hire, head of community, a wonderful human, one of the best people anywhere. Funny part is he did not come from DTC. He came from Yelp. 

That is exactly why he was great. He understood people, events, how to make someone feel seen, the invisible mechanics of a room. He knew how to connect people without it feeling like networking. He knew how to host. That matters more than industry experience for community. 

A great community person is part host, part therapist, part Reddit mod, part nightlife promoter, part camp counselor, part diplomat. Because the dark truth is this. It is better to have no community than a bad one. A bad community is a dead mall with overpriced souvenir shops, a hollowed out Spencers and a Cinnabon. It makes your brand feel smaller. It teaches people that nobody cares. 

Kevin made sure that did not happen. We brought in smart people to own specific slack channels, someone great at Google Ads, someone great at creative, someone great at Meta, someone great at retention. They were not there to hard sell. They were there to drop heat. And because they dropped heat they got deal flow anyway. 

That is how real community works. You create a room where generosity compounds. One of my favorite stats from Narwhal Nation was that 51 percent of the messages were not in public channels. They were DMs. Sounds bad if you measure community like a dashboard goblin wearing khakis and sperrys (note to self don’t become a dashboard goblin). But it was actually incredible. It meant the inmates were running the asylum. 

The community no longer depended on us. People were forming relationships, helping each other, doing deals, sharing context, building trust outside the official rooms. The strongest communities eventually stop needing you to start every conversation. That is the whole point. People helping people. Power stuff. 

People love to dunk on merch. They are usually right. Most merch is landfill with a logo. The mug from swag.com (no shade cool service) with the logo so the overworked marketer can tell their boss they have company swag. This ain’t the path.

Great merch is different. Great merch is not a t-shirt. It is a badge. It is a signal. It says I was there, I get it, I am part of this thing. We did a lot of merch at Triple Whale, good merch, fun merch, stuff people actually wanted. And yes it mattered. 

When you see people wearing your brand voluntarily, when they post it, when they bring it to events, when it becomes part of the visual language of the company, it does something no performance campaign can do. It makes the brand feel real. 

B2B companies forget this all the time (B2B should actually stand for Boring to Boring). They think because they sell software they are not allowed to create physical artifacts. Wrong. Software is invisible. Merch makes it visible. A dashboard lives behind a login. A hoodie walks into a coffee shop. Do not sleep on merch. Just do not make bad merch.

One of the things Triple Whale did incredibly well was activate nodes in the community. Not influencers in the disgusting spray tan discount code sense (OMG I am obsessed kinda of vibes. Fun fact, they indeed are not obsessed).

I am talking about real nodes. People with trust. People operators listen to and respect. People whose taste carried weight in the market. At one point there was a belief that we were paying everybody. We were not. Ninety five percent of those people were not paid. Trust me I was spending way too much money on dumb shit. This was pure organic love.

They just liked the product. They liked the team. They liked the energy. They liked being early to something that felt like it was going somewhere. That was one of the best feelings I ever had as a CMO. 

That is why those four slides in the diligence deck mattered so much. They were not just about marketing. They were proof that the market believed.

If you make people feel something they will remember you, even in attribution software, especially in attribution software. 

One of the most magical feelings in the world is bridging the digital to real world. It’s the marketing equivalent of breaking the fourth wall (editor’s note no this isn’t AI this is just how I talk you f*cks!). So we decided to take the community offline. 

We geoclustered our customers and ran the Whale Roadshow in New York, Toronto, LA, Austin and London. Simple idea. Find where the most customers are. Put them in a room. Make the room good. That last part matters. The room has to be good. Not a sad hotel conference room with warm white wine and a branded step and repeat that looks like a hostage backdrop blasting Creed (TBF One Last Breath low key bangs, but you get the point). A real room. Good energy. Good people. Good programming. Good drinks. Good reasons to talk. Pro Tip: Kevin was so good at choosing rooms that forced interaction via the layout. Try and do this. If the layout has a lot of compartments you end up with cliques and clusters. No bueno.

The Whale Roadshow worked because it made the community tangible. People who had seen each other online got to meet in person. The brand stopped being software and became a scene. This is the part most B2B companies miss. They think events are about pipeline. Events are about memory. Pipeline is downstream of memory (warning do not say this during your budget review). 

The second pillar was content. And content was everything. Content is the king of the inbound motion. Not boring content. Not download our 47 page guide to attribution maturity content. Not SEO chum. Not white papers written by people who have never had an original thought in their lives. There is a place for that stuff sometimes, maybe, if you must. But that is not where the magic starts. 

The first two things I started at Triple Whale were the newsletter and the podcast. The newsletter was called Whale Mail. Again whale themed. Again no apologies. In the beginning I made it hard on myself, writing a long form essay and a weekly wrap up. It was a lot of work especially while also doing everything else. But it became one of our most important content assets. 

Eventually the indomitable Alexa Kilroy took it over and made it incredible. Alexa was one of the best hires I have ever made. More on hiring later. Whale Mail worked because it gave us a direct line to the market. 

It let us teach. It let us entertain. It let us shape the conversation. It let us show taste. A newsletter is not just a content channel. A great newsletter is a recurring appointment with your worldview (like for real tho try to send out at the same time same day same structure/content; think of it a like a social contract if you break this social contract people will get pissed and leave aka unsub). 

Then there was the poddy. You're Not Your ROAS. I hosted it. It did really well. But the important thing about a podcast is not always the download number. This is where marketers get stupid. They look at a podcast and go only 700 people listened to this episode. Okay. Were 17 of them perfect fit buyers. Did three of them mention it on a sales call. Did one investor listen. Did one future employee hear it and decide this company was different. Did one customer feel smarter because of it. 

Use Gong, talk to sales, talk to customer success, listen for the echoes. We had people come into sales calls saying they listened to the podcast, liked us and wanted to sign up. That matters. A podcast does not need to be Joe Rogan to change the slope of a company (although we did have our podcast studio built by the same guy that did Rogans). Sometimes it just needs to be good enough to make the right person feel like they already know you. 

Then there was social. And social was its own beast. Tommy Clark came in as our social media lead. One call hire. Absolute killer. Fresh out of school and already had the thing you cannot teach easily. Taste plus velocity (are seeing a recurring theme of taste).

When you are building a brand it helps to know the human archetype you want it to represent. Triple Whale was not supposed to feel like a corporate analytics platform. 

The archetype was something like a really smart professor with elbow patches on his wool jacket who also smokes weed. Brilliant but approachable. Technical but funny. Analytical but not dead inside. That mattered…a LOT. Because it gave the voice a center. We leaned hard into meme marketing and it worked. 

Our Twitter account exploded. We passed competitors left and right. People paid attention. Humor is one of the most powerful tools in marketing because humor disarms people. A court jester can say things a king cannot. A meme can smuggle truth past someone's defenses. In ecommerce there was endless pain. Attribution was broken. Meta was chaotic. ROAS was lying. Dashboards were messy. Agencies were fighting with clients. Founders were confused. Memes let us say the true thing without sounding like a software company diagnosing the market from a webinar deck. 

But there was a downside. When we tried to pivot the Twitter account into more serious educational content it did not really work. We had trained the audience to expect one thing. They wanted the jokes. They wanted the memes. They wanted the whale account to be funny. So here is the lesson. The algorithm will reward you for becoming recognizable, then punish you for trying to become dimensional. Choose carefully.

Meme marketing gave us reach, a lot of reach, but it also created a ceiling on that specific channel. Would I do it the same way today. Probably not. Not because humor is dead. Humor will never die. But brand accounts are in a much harder place now. The better version today is probably founder led, team led, creator led. People want people. They do not want a logo pretending to have a personality unless the execution is truly exceptional. The principle still holds. The tactic may not. 

One small thing that became very big. We owned the whale emoji. When people joined Triple Whale they put the whale emoji in their profiles. It became a little signal. You could tell who was part of the world without needing to read a bio. That is powerful.

Symbols matter. Religions have symbols. Countries have flags. Sports teams have colors. Luxury houses have monograms. Great brands compress identity into little marks people can carry around. 

For us it was the whale emoji. Simple. Stupid. Effective. That is often how branding works. Sidenote: We even did a whale eyes campaign to mimic the bitcoin maxi campaigns. Looking back it was low key cringe, but shooters shoot.

Everyone talks about product market fit. That matters obviously. But there are other kinds of fit that matter too. Founder market fit. Does the founder actually understand the product/market. Have they lived the pain. Triple Whale had extreme founder market fit. 

AJ and Max were operators. The first version of Triple Whale was basically their spreadsheets turned into software. They knew the pain because they had lived inside it. 

Then there is channel market fit. This is underrated. Your market is not equally available everywhere. For us Twitter (I refuse to call it X) had incredible channel market fit. That is where ecommerce operators, agency people, media buyers and founders were hanging out. That is where they were learning. That is where they were arguing. That is where the culture was being made. 

LinkedIn was okay. Instagram was fine. Twitter was the room. So we went hard in the room. This sounds obvious but companies mess it up constantly. They distribute content based on internal preference instead of market reality. They say we need to be on TikTok. Do you. They say we need a LinkedIn strategy. Maybe. The question is not where can we post. The question is where does the market already gather to decide what matters. Go there. Then learn the language.

Editor’s note: One big regret was not developing a cohesive and impactful LI strategy. The reality is that the big bois and girls were probably on LinkedIn, while the operators were on Twitter.

The third pillar was education. This became especially important when attribution became the wedge. Triple Whale was doing well as an analytics company. Then iOS 14 happened. AJ saw it immediately. This was the moment. Attribution was breaking. Operators were confused. Meta reporting was getting weird. The market had pain, real pain, expensive pain. 

AJ told me we were going to launch an attribution product. I said what attribution product. He basically said don't worry about it, can you sell it. Yes. I can sell anything. 

So we sold it. Before a line of code had been written we sold roughly $2 million in ARR for what became the Triple Pixel. Then the engineering team built it. In Israel. In something like two months. From the ground up. Absolutely insane. 

I still think about that. The audacity. The velocity. The trust. The sheer startup violence of selling the future and then sprinting hard enough to make it true. That is not advice by the way. That is a war story. The important part is that attribution created an education gap (and a huge wave for the business to ride; it is much easier to ride a wave than create one). 

People needed to understand what was happening. How to look at dashboards. What attribution models meant. What lookback windows mattered. How to think about ROAS after iOS 14. When to trust Meta. When not to. How to make decisions when every platform claimed credit for the same dollar. So we taught. Webinars. Office hours. Community discussions. Newsletter breakdowns. Podcast conversations. Product explainers. Triple Whale University. 

Education became a huge part of the motion. But there is an important distinction. Education is valuable even if you never use the product. Product marketing requires the product to get the value. Both matter. But they are different. If someone can consume your educational content, become smarter and still not buy from you, that is not a failure. That is how you build trust. That is how you become part of the market's operating system. What education can do is put you in the decision set and ideally the top choice in that decision set. So when a consumer is ready to buy they think of you.

There was another education that had to happen too. Mine. When I first started I was doing everything. I was the one man marketing department, the paid media guy, the newsletter guy, the podcast guy, the brand guy, the sales call guy, the sure I'll figure it out guy. And for a while that was useful. 

Early stage companies need people like that. People who can create motion from nothing. People who do not need perfect process. People who will pick up the shovel, the microphone, the ad account, the Notion doc, the sales deck, the camera and the event plan. 

But eventually if the company works the job changes. And one day AJ sat me down and told me the truth. He said essentially you are the best IC I've ever been around, you can do anything, but I don't need an IC right now, I need a CMO, if you want to stay an IC that's fine, we'll find a place for you, but right now I need a CMO. 

That was a very hard conversation. Because competence is addictive. When you are good at doing the work, doing the work becomes a hiding place. You can always jump in. You can always fix it. You can always be the hero. You can always confuse motion with leadership. 

But a CMO cannot just be the best player on the field. At some point you have to become the coach. You have to recruit, build systems, set direction, create clarity, decide what matters, decide what does not, let other people own things (OMG delegation was sooooo hard for me), let them be better than you at things. That day I had a choice. Stay the best IC in the room or become the CMO the company actually needed. 

I told him I want to drive the boat. And that was when I really started to flourish. Not as the CMO of a one man marketing department. As a real CMO. That shift changed everything. I had an incredible run hiring at Triple Whale. 

Part luck, part taste, part timing, part the fact that the company had real heat and people wanted to be close to it. We built a great Austin office. We had the guy who built the Joe Rogan podcast studio build ours (yes I mentioned this already). 

It was ridiculous, in the best way. There was a period where Triple Whale had so much aura it felt illegal. The company was growing fast. The brand was hot. The office was alive. The team was full of killers. It was one of those rare moments where the work was hard, the hours were insane and everyone still knew they were inside something special. 

My hiring philosophy is simple but dangerous if you do not know what you are doing. I hire on vibe. Not only vibe. But vibe matters more than people want to admit. The problem is that most people cannot actually check a vibe. They confuse charisma with competence, polish with talent and confidence with judgment. 

I am old enough and have made enough mistakes to know what I am looking for. I hired for talent, taste and social context. I hired for what people had built. I wanted people who could change the slope, not 1xers maintaining the slope. 

Alexa Kilroy is the perfect example. I did not know exactly what role she should have at first. I just knew she was a killer. Kept trying to get her to join. Head of content. Head of brand. Something else. Whatever, just come here, we will figure it out. It took me six months to convince her. Worth it. 

Tommy, same thing. Kevin, same thing. The best people had energy you could feel. A players change the physics of a company. C players create drag you explain away until it is too late. 

My advice is hire slow. Fire fast. I know that sounds cold. It is not. Keeping the wrong person in the wrong role is not kindness. It is cowardice dressed up as empathy. Let them go well, give severance, be humane, let them keep the laptop if you want, but do not build a rocket ship with people who make the rocket heavier every week. 

Now for the fun part. Moonshot marketing. The stuff people love to talk about. The stuff I love to talk about. The Whalies. DTC After Dark. The Beluga Bash. Sending an iPhone to space. Product launch stunts. Scarcity mechanics. Retro pixel discs. Big swings. Weird ideas. Things that make the brand feel alive. We did a lot of this. Fun as hell. And some of it didn’t work. Some of it worked okay. Some of it absolutely exploded. 

The Whalies is probably the best example. It was stressful, ridiculous, beautiful and somehow still lives on. The fervor around it was real. The team showed up in a huge way, Kevin, Alexa, everyone. It became a signature moment. 

But here is the part people do not want to hear. Moonshot marketing only works if the meat and potatoes are already there. If you do not have community, content, education, product pain and real distribution, your moonshot is just a stunt floating in space. 

A stunt without a system is theater. A stunt attached to a system can change the slope of growth. That is the point of moonshot marketing. Not attention for attention's sake. Slope change. You are looking for asymmetric bets. Things where the downside is contained but the upside is narrative, reach, memory, community energy and market belief. 

Most companies cannot do moonshot marketing because they are too afraid to look stupid. The best ones are willing to look a little stupid on the way to becoming unforgettable. Not every big swing worked the way I wanted. 

DTC After Dark is the one that still bugs me. I thought it had the ingredients. It had the format. It had the vibe. It had the ambition. It was not another webinar. It was not another founder interview with bad lighting and a worse title. It was trying to be a late night show for DTC. That was the right instinct. But it only did okay. 

The biggest issue was timing. We were not able to release it inside the window where the momentum was open. And when a creative idea misses its moment it does not matter how good the idea was on paper. Momentum is its own currency. 

Wild story. I can share it now because it was so long ago. The reason it was released so late was that the people we hired to film it had a full production meltdown. One of the producers had a falling out with the director and STOLE ALL THE FOOTAGE. Not kidding. They had to threaten to sue him and a few weeks later he had cops show up at his door to confiscate the stolen footage. You say you want to be a CMO, huh!? Like WTF. I remember thinking to myself, is this real life?! Anywho, the show goes on.

That is life. Startups are messy. Production is messy. Companies are messy. But the lesson is simple. Creative has an expiration date. Especially in a fast moving market. A great idea released too late can feel like a pretty good idea. A pretty good idea released at exactly the right moment can feel like genius. That one taught me a lot. 

Not every moonshot fails because the idea was wrong. Sometimes the operation misses the weather window. 

There was one idea I really wanted to do that we never got around to. DTC Cribs. Basically MTV Cribs but for ecommerce brands. We would pick five to ten of our biggest or most interesting customers and go to their HQs. 

Full tour, founder interview, warehouse walk through, desk setups, creative rooms, weird rituals, favorite products, the whole thing. Make DTC feel like a world. That was always the bigger opportunity. Not just how do we sell more software. 

But how do we document the culture of the people building these brands. DTC Cribs would have done that. It would have made our customers the stars. It would have given operators a reason to watch. It would have created social clips, founder stories, community pride, customer love and category lore. 

I still think that format has legs. Maybe not exactly like MTV Cribs. Maybe more modern, more founder led, more cinematic, more operator focused. But the instinct was right. 

Your customers are not just logos. They are characters. Most B2B companies treat customer marketing like a case study PDF. What a waste. A great customer story should feel like a backstage pass. 

I am not a huge product launch guy. Most product launches are just internal theater. The company cares. The market does not. But the Triple Pixel launch worked. We created scarcity. We built anticipation. We had these cool retro pixel discs designed by Zach from Foreplay who is incredible. People got numbered discs. They posted them. It felt like an artifact, not an announcement. That is the difference. 

A normal launch says we shipped a feature. A good launch says something is happening. The market does not want your changelog. The market wants a reason to care. 

Some of the Triple Whale playbook still works. Some of it does not. Community still works, maybe more than ever, but it has to be real. The era of join our Slack group as a growth hack is dead. You need a reason for people to show up, a reason for them to stay and a reason for them to feel status from being there. 

Content still works. But mediocre content is dead. AI has flooded the world with beige competence (not like this exquisite straight from Rabah’s head essay). The only content that matters now has a real point of view, real taste, real experience or real utility. 

Education still works. Especially in markets where the rules are changing. Whenever the market is confused, whoever teaches clearly earns trust. 

Moonshot marketing still works. But only when it is attached to a real machine. The biggest thing I would change now is the social strategy. I would make it more founder led and team led. Brand accounts can still work but they are harder. People want faces. They want operators. They want the humans behind the machine. 

At Triple Whale we accidentally had a lot of that. I was active. Tommy was active. Alexa was active. The founders were known. The team had social context. The whale emoji connected it all. That part I would double down on. A brand is not just what the company posts. A brand is the combined blast radius of everyone credible attached to it. 

My biggest regret is not a campaign. It is not a hire. It is not a missed number. It is that I was not present. One of the hardest parts about being a CMO, especially inside a rocket ship, is that you are always looking for the next alpha. The next campaign. The next channel. The next hire. The next event. The next launch. The next slope change. 

And then the thing happens. The event works. The campaign lands. The room is full. The team pulls it off. The market notices. The thing you hoped would happen actually happens. And instead of being there, really being there, you are already somewhere else. Tired. Anxious. Thinking about tomorrow. Thinking about the next thing. Thinking about what did not work. Thinking about what you could have done better. Thinking about the next alpha. That is bullshit. And I did that. 

There were moments I should have enjoyed more. There were rooms I should have looked around in and thought this is it, this is the thing, this is what we were building toward. You always know when something happens for the first time. You almost never know when it is happening for the last time. 

That is the part that gets me. You do not know which dinner is the last dinner with that version of the team. You do not know which event is the last event before the company changes. You do not know which office day is the last day before the magic becomes a memory. 

Ambition is useful. But unchecked ambition makes you spiritually unavailable for your own life. So if there is one personal lesson I would pull from the whole Triple Whale chapter it is this. Be present. Be grateful. Take the win when the win is happening. You can hunt the next alpha tomorrow. 

Triple Whale worked because it was not just software. It was a world. Narwhal Nation. Whale Mail. You're Not Your ROAS. The Whalies. The roadshows. The merch. The whale emoji. The memes. The education. The office. The people. The lore. 

Everything pointed in the same direction. That is what brand is. Not a logo. Not a color palette. Not a positioning doc collecting dust in Notion. Brand is accumulated meaning. 

It is what all the little decisions add up to in someone's head. At Triple Whale the meaning was clear. These people get it. These people are fun. These people are smart. These people are moving. These people are ours. That is a powerful thing to create. 

Especially in B2B. Especially in software. Especially in a category most people would have assumed was too boring for cult energy. But again. There are no boring categories. Only boring operators. 

So if you want to build something people remember do the meat and potatoes first. Build the community. Create the content. Teach the market. Hire killers. Find your channel market fit. Then when the machine is humming take the big swings. Send the iPhone to space. Throw the fake award show. Own the emoji. Make the merch. Name the community. Give people a story they can repeat. 

Because the best companies do not just acquire customers. They create believers. And for a little while there, inside that weird chaotic whale themed rocket ship, that is exactly what we did. The funny thing about rocket ships is everyone tells you to enjoy the ride. But when you are inside one it mostly feels like holding on. So hold on. 

But every once in a while, look out the window and enjoy the view.

Cheers,

R