So we are gearing up for SaaStrAnnual 2020, our 6th SaaStr Annual ever.  After the first one in 2015 (which was really just a turbo-charged 1 day meet up for 1,200+ planned in just 90 days), I thought I was done.  1 was enough.  But luckily, I was talked into doing another.

So after 5 years and 50,000+ attendees to our various events (including 2,500 for our second SaaStrEuropa this June in Paris), it was time for a refresh.  Every 5 years, you have to adjust your tactics, and even evolve your strategy.  When we started, we wanted to be a mix of an anti-Dreamforce and Between Two Ferns.  That was incredibly fun.  But the cloud has grown 10x since then, and most of our community wouldn’t even know what an anti-Dreamforce was.  And as revolutionary as it was to hear from Aaron Levie 1 week after the Box IPO in 2015, or Stewart Butterfield right when Slack was exploding … fast forward today, we’ve all heard them speak 100 times now.  They are amazing leaders.  But there are now 100 Cloud Unicorns.  It was time to get re-inspired.

So we did a mini-road show this year and visited all the best in their categories.  Because I’ve learned you can always learn a lot from the best at anything.

We’ve visited so far:

  • Coachella
  • Shoptalk
  • Collision
  • Hubspot Inbound
  • And up next and last, Art Basel

We also hit everything from Clusterfest to Faminecon to Traction Conference (one of our favorites) and other folks doing great things.  But we learned the most from the clear #1s in their categories.


First up, Palm Springs!! What does SaaStr Annual have to do with Coachella?  Well, maybe not a lot, except Coachella has been doing something right for 25+ years.  It is a $150m+ business (together with Stagecoach) and sells out every single year.  And it means they are doing a lot of things right.  So, knowing nothing about music or techno, we were off to the Empire Polo Club.  It turned out, it was awesome.

A few things I loved, and learned from Coachella:

  • Surprise-and-delight the user before they start using your product.  The box that came with our wristbands wasn’t just an envelope.  It was an exciting adventure before we got there, with a super cool box you’d be proud to put on a shelf, and fun games and collateral to get you excited.  I give them an A+ for onboarding excitement!!

  • Do fewer, better things.  There are crazy cool art installations at Coachella, but not that many.  Instead of 100+ activations and art pieces (which there is plenty of space for), they went for maybe 5-6.  And half were repeats from prior years.  But it works.
  • If you have scale — use it to just make it happen.  It was surprisingly easy to get to, and back, from Coachella.  They rented every single bus in the area and had shuttles leave almost 10 minutes to just zip you home.  They hired church buses.  School buses. Whatever it took to make it happen.
  • Make sure all your talent / customers feel like heroes.  Not just the whales.  The coolest stage at Coachella was not the main stage.  The main stage was probably the most boring and least designed, and the furthest and hardest to get to.  But the cool arch stage you see in A Star is Born?  That’s actually the #3 stage.  But you feel like a hero being on it, and watching it.


Vegas!! Ok, next up was Shoptalk.  Shoptalk is the leading industry event for e-commerce.  In some ways, it is what SaaStr Annual is for e-commerce.  But the team are pros.  They previously founded Money2020, still the largest fintech conference and a $50m+ extravaganza.  If you aren’t in e-commerce, you’ve never heard of Shoptalk.  But if you are — you have.

A few things I loved, and learned from Shoptalk:

  • Spend where it matters.  At SaaStr Annual, we try to make everything cool.  And that’s fun.  But does it matter?  Shoptalk spent money where it mattered, but where it didn’t, they didn’t.  Stages 2-5 had zero decorations.  Many halls and spaces were standard Venetian Hotel.  The big party was in a ballroom.  But folks loved Shoptalk.  It is easy to spend on things that don’t matter.  Put the money where you get the highest ROI.  The Shoptalk team are pros here.
  • Connecting buyers and sellers is worth a lot.  Shoptalk does an incredible job of matching buyers and sellers (and charging sellers quite a bit).  Tickets are super expensive, and many meetings are too.  But they deliver. They deliver leads.  If your product claims to deliver ROI, worry less about what it costs.  And more about delivering 10x ROI back.  That’s my lesson learned.
  • Everyone was there.  I have made a number of investments in e-commerce.  It was super easy to just meet everyone there.  And to bump into so many other great folks.   This is what we are doing with SaaStr Annual, too.  Making it Where The Cloud Meets.
  • Brands build on themselves.  Shoptalk started 5+ years ago like SaaStr Annual.  But they didn’t have 1m+ pageviews and 3000+ pieces of content to start them.  Instead, they created a brand from nothing.  And today it’s an iconic one in e-commerce.  Once you have a mini-brand, lean in as much as you can, that’s my learning.  Mini-brands become Big Brands in a few years if you do everything you can to nurture, serve and grow them.


Then, off to Toronto for Collision!  Collision is the U.S. brand of Web Summit.  Together, they are the #1 tech events.  And they’ve been doing it for a long time.  They are the Pros, again with a nine-figure business.

A few things I learned from the best-in-the-best in tech conferences:

  • Know your customer.  One thing Collision did incredibly well, that we are just learning about, is Press.  They had hundreds of journalists there.  Why does that matter?  Well, CEOs love it.  They love jetting in and doing 10+ interviews in 1 fell swoop with all the media.  At SaaStr, we don’t really think of media as our customer.  Perhaps we are missing that key insight.  Web Summit does, and they crush it.
  • Infrastructure changes are always harder than we think.  Collision moved from New Orleans to Toronto, and got more space and easier connections.  But they were still figuring out all the challenges from new infrastructure.  Stick with what works as long as you can.
  • It’s fine to charge extra for things people are OK charging extra for.  We forget this sometimes.  In the enterprise, it is OK to charge for services and for implementation.  At Collision, they charged for coffee and lunch. We don’t, and it costs us over $1m.  Perhaps we should.  I didn’t hear anyone complain they had to buy their coffee.  I’ve also never seen a customer complain paying an extra 10%-20% for services on an enterprise-level contract that involves business process change.

Hubspot Inbound

Next up, Boston and New York!  OK we are getting a little tired now.  Hubspot Inbound is probably the #2 SaaS vendor event behind Dreamforce, so we had to check it out.  Brian Halligan, CEO was also kind enough to invite me to join a panel with him on Founders’ Day.

A few things I learned from Hubspot with 20,000+ attendees:

  • Community, Community, Community.  Hubspot didn’t spend a fraction of what we do decorating the Boston convention center.  There weren’t that many activations, and the lobby of the adjacent hotel just looked like a hotel lobby for the most part.  But … everyone in the hotel lobby was having a great time.  It was packed, everyone was smiling, sharing stories, sharing learnings.  Hubspot has built an amazing community, and that is 100x more important than almost anything else.  People loved being there, sharing, and learning from each other.
  • We are all still learning.  SaaStr Annual is now as big as Inbound.  I feel like we know some things cold, but in other areas, we know nothing.  It is always great sharing notes with the team there.  Seek out your peers and sharing your failings, your learnings, and where you need help.  It is always a pleasure to interact with and sharing learnings with Team Hubspot.
  • Go the extra yard.  And always be authentic.  This may sound obvious, but Brian and Dharmesh’s keynotes were awesome.  They weren’t what I expected.  They were more generic than specific.  But, boy they worked hard on them.  Not to promote Hubspot, but to give back and inspire their community.  They were both authentic.  Once you give here, it’s all over.  We don’t sell out at SaaStr.  It costs us a lot of money.  And that is fine.

Next up, SaaStr-at-Art Basel.  We’ll do a meet-up with 500 Startups on Dec 5 in Miami, and explore Art Basel on the side.  To learn from the best in the best here, too.

Then we’ll finish this exercise up and be heads down for the next 5 years.

Making sure SaaStr Annual, Europa, and Scale are always Where The Cloud Meets.  And that they are awesome.

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