I Attended Chilipalooza, Drive, and Spryng — Here's How They Compare

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Hey. I’m Dave, marketer turned cofounder. I'm the CEO of Singulate, an AI email editor for B2B marketers that makes hyper-personalized and segmented marketing messaging 90% easier to create using all the data you already have in HubSpot.

Quick background on me: I was on the founding team at Hopin, where I led marketing and growth for ~5 years. Originally from New York, I now live in the Baltimore area with my wife of 13 years and 3 kids.

Meeting your LinkedIn network in person

I attended 3 really cool B2B marketing conferences in the last 12 months that followed a similar “unconference” style model:

I wanted to share my notes and observations about what they were like and how they compare.

This is not a recap of learnings and takeaways (another post for another day), but rather a journal of observations from a random attendee about what it was like to be at all three and how each experience was different.

Bottom line: These events were massive successes in their own ways. The teams behind them are amazing at what they do. I love each of them and highly recommend you attend all of them.

Content winner: Drive

Drive struck the perfect balance between content and networking. It’s tough to beat Devin Reed, Amrita Mathur, Ross Simmonds, and others giving away their playbooks and secrets. Daniel Cjmela is essentially a standup comedian (who was also at Chilipalooza). Plus, you get CMO wisdom from companies like Zapier, Copy.ai, and GoTo. The content gave attendees something to discuss during the breakouts.

Chilipalooza didn’t have any speakers, which frankly, was ballsy. Alina gave a casual welcome speech but it was mostly to say hi and give shoutouts to sponsors, but that was it. Intentionally. Good speakers can anchor a conference, provide takeaways, and phone-raising UGC. But they can also be boring, lose people, and slow the event’s pace down. You don’t want to force people to sit through what they already get from LinkedIn every day. Chilipalooza avoided this risk entirely and it paid off, but I can’t help thinking… imagine if Emily Kramer spoke about newsletters, Jordan Crawford about revops, Kyle Lacy about scaling demand, or Robin Daniels about leadership. Feels like a missed opportunity.

At Spryng, except for a handful of talks like the Fletch guys’ website roasts (laughed out loud) and Adam Robinson’s lightning session, the keynotes this year fell kinda flat? I talked to several other attendees who said they would rather have spent the time networking or in groups. This is where it would’ve been awesome to have some sort of Austin activity together (see next section).

Venue winner: Chilipalooza

All three cities were excellent choices. Burlington’s green mountains and view of Lake Champlain were beautiful. The dessert mountains and warm sunshine in Phoenix manifested Chili Piper’s brand perfectly. Austin’s creative and no-bullshit vibe fits Spryng’s energy.

The venues — where you spend the majority of your time — were very different, each one with pros and cons.

Drive met at a giant, fresh-looking coworking space on the lake with a stage and local offices.

Chilipalooza booked out an entire health and wellness resort with spas, massages, hiking, cold plunges, saunas, steam rooms, pools, pickle ball, sound baths — should I keep going?

Spryng met in an artsy, grungy brewery event venue with outdoor space and a full-service restaurant and bar.

The very obvious winner for me here was Chilipalooza for one reason and one reason only: booking out an entire resort made it 10x easier to be immersed in the experience with everyone else. It cut down on commute time. It unplugged the constant temptation to stay and do work from your hotel. By having a room onsite, it was so convenient to just step outside my room and immediately know that anyone I see is someone to connect with. Everything was a quick walk away. The feeling of being cloistered together made it feel much more like a community. Shout out to Chelsea Lassen for organizing!

Btw, I met Sam Yarborough who puts on a similar conference called Arcadia where tech people disconnect in the mountains of Montana in tents listening to bluegrass and it sounds like it does this.

Networking winner: Three-way tie

Unlike massive conferences like Inbound and Dreamforce, all three of these events brought together highly curated groups and made it easy to meet each other. Not sure if you’d agree but getting to meet people and make new connections in-person is the number one reason why I go to these events, especially as someone who works from home.

The three best environments to meet new people that all of these events got right are:

Pre- and post-parties (Spryng did the best here) - love it or hate it, alcohol helps break the ice. One request that everyone agrees with: don’t make the music too loud. Make it easy to hear each other, don’t force people to yell.
Smaller breakout sessions where everyone introduces themselves and gets to share
Meals - sitting down and breaking bread at tables for 30-60 minutes

One thing that Chilipalooza did well was give us physical activities to do. Sports, hikes, yoga — experiences that hinged less on talking and more on doing. It broke up the repetition of direct face-to-face networking and provided shoulder-to-shoulder space to stretch our legs and take off our work hats. Of all three conferences, the hike in the mountains of Phoenix was my favorite because I felt like a could finally disconnect. Drive did a 5k run in the morning, where I was a loser and missed out on it, but can see that being similar.

Breakout sessions winner: Chilipalooza

Drive’s breakouts were good, but everyone was assigned to the same breakout group for the entire conference, so meeting with the same people over and over kind of defeated the purpose of going to the event to meet new people.

Spryng did a great job with changing up who was in the groups, which let us meet lots of new people. But had lots of other problems. The breakout numbers were wrong on our badges. Half the moderators that were supposed to be there according to the website weren’t there, and the substitutes were semi-prepared, some over-moderated the conversation. My second session had the same three people from the first.

Chilipalooza’s breakouts had the most thought put into them it seemed. The topics were pointed and specific, and the right mix of profiles were grouped together, based on what attendees filled out on the registration form.

Food & drink winner: Spryng

Spryng’s venue kept the food and drinks flowing the whole time. Delicious breakfast, lunch, and dinner. Restaurant food was always available for individual ordering anytime, an open bar available the entire time, and an espresso bar in the mornings. All free and high quality. Super nice.

Drive was more paid self-serve experience. Breakfast and lunch were included. Coffee bar was paid. And dinners were organically organized by attendees around Burlington, so if you weren’t able to get looped into a group, you were left out and you were paying for your food. A thoughtful touch was serving Vermont-local Ben & Jerry’s during a breakout session.

Chilipalooza’s food was the most unique. It was all organic, natural, and healthy. No junk food or sugary drinks. For example, there was no soda available on site. In the evening, the bar was free and open in the evenings. The food was yummy and it felt good.

Other observations:

Digitally connecting. Spryng’s event web app was “AI-enabled” - it did a cool thing of recommending attendees to meet, which helped break the ice (”the app said we should meet”) but found it a little underwhelming. Chilipalooza made a Whatsapp community, which I loved. The immediacy of connecting before, during, and after the event kept the energy going. Drive had it’s paid community in Circle so it was kind of already built-in.

Takeaways

I loved Chilipalooza’s venue strategy and vibe. While it could’ve improved a bit on content, the experience was far and away the most balanced and energizing.

Drive’s content and community made it feel really exclusive. I learned a ton, met great people, and Burlington is a unique gem of a city. And for the price tag? Holy Moses, what an amazing deal.

For Spryng’s price tag being higher than the others, I expected more, but the food and drinks and people made it totally worth it. I heard that Chilipalooza and Drive were inspired by Spryng, so maybe because I experienced those first, the bar was higher going in?

I spoke briefly with a handful of others who attended all three events, such as Natalie Marcotullio at Navattic and Madhav Bhandari at Storylane, and their takeaways were very similar.

Natalie said:

"I think they were hard to compare because they were all so different. For Drive, I really did love the talks (and I'm not just saying that cause I had one lol) and how close everyone got. For ChiliPalooza, the venue and vibe was unmatched, and I did love that you could so easily go to your room or the spa in your downtime. For Spryng, the community and events around it were so much fun, and the food was great. Honestly, I had good and a little less good moderated convos for all three. I think moderated sessions can be really tough, seems like there is always something with the groups not fully working out or moderators not showing up."

Nuggets for B2B marketers

From Drive:

You should be posting on LinkedIn, focus on quality content from personal brands, and repurpose it across channels. Your moat is the community you build around your business.

From Chilipalooza:

AI and agentic workflows are the future of GTM efficiency. But there's a lot of noise and it's difficult to tell what's hype vs. real. The technology changes every month - we're all learning together what works best for our unique teams and businesses.

From Spryng:

In the world of AI, product and marketing become commoditized. The only differentiation that remains is brand. The best way to build a brand? Events and community.

More B2B companies should do these types of events.

Especially as the online B2B world gets more crowded with AI, events like this are the best way to cut through the noise and invest in your brand. At least as a sponsor.

My company Singulate is still an early stage startup, but as soon as we start scaling, you bet your bottom dollar we’re going to host a conference like this. Not sure what it will be called, but I already know who it will be for...

Anyways, who else went to all three? Or did you go to one or two? What did you think? What did you like about each? I’d love to hear.

See you at the next ones.