What happens when you throw out the GTM playbook

That investor was wrong. Gamma is now worth $2B, with 50M users and more than half their growth driven by word of mouth.

They're one of 6 AI-native startups in HubSpot for Startups' free Bold Bets Playbook. Replit grew revenue 50x after half the team pushed back on the strategy. Ramp generated 100M+ views from a single stunt. Clay's co-founder wouldn't hang up a sales call until the prospect DMed him in Slack.

Each one took a GTM risk most founders would never greenlight. Each one paid off.

Music Monday is our weekly TipSee Buzz feature covering the live music headlines, trends, and overlooked shifts worth paying attention to.

The humidity in Nashville this past week wasn't just weather: it was a character in the story. If you were anywhere near Lower Broadway between June 4th and 7th, you didn't just see the music; you felt the thick, 95-degree air pressing against the thousands of cowboy boots hitting the pavement. CMA Fest 2026 officially wrapped last night, and while the "heatwave of the decade" headlines were buzzing, the real story was the sheer resilience of the live music ecosystem.

There’s something about a hundred thousand people descending on a ten-block radius that highlights exactly where the industry is heading: and where the friction still remains.

Night 1 at Nissan Stadium set a bar that most thought would be impossible to clear. When the lights dimmed and the opening chords of “Round Here” started ringing out, the collective gasp from the crowd was louder than the speakers. Seeing Tyler Hubbard and Brian Kelley back on stage together for a surprise Florida Georgia Line reunion wasn’t just a nostalgia play: it was a masterclass in artist-fan chemistry.

When Tyler told the crowd, “First of all, God is good. Second of all, life is short. And most importantly, your boys....we back, baby!” he wasn’t just announcing a tour; he was closing a gap that had been left open in the genre for years.

But as much as the stadium moments get the press, the real heartbeat of the week was found on the daytime stages. We’re talking about over 150 artists grinding it out on the daytime festival stages under a relentless sun. This is where the industry’s "expectation gap" is most visible.

Fans today don’t just want to watch a set from three hundred feet away; they want to participate. They want to influence the show. They want to be part of the moment. We saw artists on the daytime stages navigating massive crowds where the traditional "pass the hat" or "venmo on a cardboard sign" simply fails to scale. When you’re playing to five thousand people at 2:00 PM in a heatwave, you don’t have time for friction.

We were helping run some of the smaller stages during the week, and that made the shift even easier to spot in real time. The artists who kept things moving and made it simple for fans to jump in were the ones that seemed to hold attention the longest. Even in the middle of the chaos, you could feel how much more engaged a crowd becomes when supporting the artist feels quick and natural.

By Night 3, the conversation shifted back to the legends. Tim McGraw took the stage and, in a brilliant move, leaned almost entirely into a 90s-heavy set. It was a reminder that while the industry moves fast, the "I was there" factor of a classic hit is the ultimate loyalty builder.

Nostalgia is a powerful monetization tool, but only if you have the infrastructure to support the fan's desire to engage in the moment. Whether it's a stadium headliner or a solo acoustic act on Broadway, the goal is the same: create a lasting connection that survives long after the festival gates close.

The broader implication here is how much more intentional the fan experience has become. We are moving away from a world where live music is a one-way broadcast. The fans at CMA Fest weren't just spectators; they wanted to feel involved, connected, and part of what was happening in real time. The artists who embraced that: instead of fighting the "phones in the air" trend: were the ones who seemed to leave with the most momentum.

Since we only helped run some of the smaller stages this year, we got a close-up view of that shift without pretending we were at the center of the whole festival. What stood out was simple: when artists have tools that help fans support them quickly and without friction, it becomes a lot easier to deepen that bond in the moment. That’s the part we’re most pumped to keep building around.

Sunday added a whole other layer to the weekend. Brandon Lake’s "Cowboy Church" pulled a huge crowd and turned into one of those moments people will probably still be talking about long after CMA Fest is over. With CeCe Winans, Dan + Shay, and a surprise appearance from Lainey Wilson, it felt bigger than just another daytime set. Then everything stopped for a moment when they paused to pray for a fan who had passed out in the heat. In a weekend full of noise, it was a reminder of how quickly a crowd can shift from celebration to care.

Sunday night at Nissan Stadium closed things out with the kind of energy only CMA Fest can really deliver. Luke Bryan debuted his new song “Country and She Knows It,” giving the finale a fresh headline moment, and Russell Dickerson took things in a totally different direction by bringing out Fetty Wap for a mashup of "Boots" and "Trap Queen." It was chaotic, unexpected, and exactly the kind of swing that keeps a festival finale from feeling predictable.

As we look forward to the ABC special airing on June 25th, most of the world will see the polished, edited version of the weekend. They’ll see the FGL embrace and Tim McGraw’s timeless silhouette. But for those of us on the ground, the takeaway is different.

The takeaway is that the hustle has changed. The "Broadway Hustle" used to be about how many hours you could stand on a stage. Now, it’s about how many real fan connections you can create in the moment.

The heat might have been the story on the weather app, but the evolution of the interactive performance was the story on the street.

So, here’s the question we’re thinking about this week: As live music becomes increasingly interactive, are we reaching a point where the "passive fan" is a thing of the past? And if so, is your setlist ready for a crowd that wants to call the shots?

One last note from the weekend: we had a record weekend in hat sales. If you’ve been seeing them around town and want one for yourself, grab yours from the TipSee shop.