As we gear up for the 5th SaaStr Annual, with an expected 12,000+ attendees, 100+ top tier sponsors, and 3+ days of content across 5+1 stages (phew!), I was looking back for our team meeting and trying to assemble what we’ve learned, and found this first tweet from almost exactly 4 years ago:

Waaay back in 2014, the type of content at, on Quora, and at our events was still novel.  Fast forward to today, and there is an amazing amount of B2B-centric content out there, and many others have put together amazing events around the hard-learned lessons of scaling revenue and scaling SaaS companies.  But all this was pretty novel back in 2014.  No one in the “next generation” had IPO’d yet (Aaron Levie came to the first SaaStr Annual a little more than a week after Box’s IPO), Unicorn rounds were close to unheard of (Atlassian had raised $60m at $400m valuation!!  woah!!  everyone couldn’t believe it), and Slack was a cool little app some of us had just fallen in love with.

But we decided it was a good idea, and a few weeks later, planned the first-ever full day, non-vendor SaaS event.  It was awesome, with Aaron Levie, Stewart Butterfield, David Sacks (fresh off Yammer’s acquisition for $1b+, which seemed so high at the time), Leyla Seka from Salesforce, David Ulevitch from OpenDNS (who sold to Cisco just a few months later for $800m, which again seemed enormous at the time), etc.

Fast forward to today, 4 years later and half-way to our 5th SaaStr Annual and everything is just so much bigger.   Dozens of IPOs.  200+ Unicorn rounds, 50+ in B2B.  Cloud companies like Hubspot, Zendesk, New Relic and more are worth $5b+.  Atlassian is worth almost $20b.  Salesforce $100b.

SaaStr as an organization has scaled along with it, and had its own growing pains.  Our first two years we outsourced the event to a great partner (thank you Max!!), and didn’t have to worry too much about operations.  So we had a net budget — and revenues — of $0.  Today, we’re managing a $10,000,000+ budget with a $14,000,000+ plan and a model for $24,000,000 in 2019.  All with a very lean team.  That’s a lot of change in 4 years.

Some meta-lessons from the journey so far:

  • Your Super Fans Carry You for A Long, Long Time.  The Annual this year will be big enough (12,000+) that we really do need to attract attendees outside of the core, long-time readers.  But until this year, we’ve sold tickets to our events almost entirely through our list.  And our list is tiny — it’s only about 40,000 names.  But the names we do have, are of very high quality.  They come.  So my learning here is, triple down on your happy customers, your most engaged users, your super fans.  They scale farther, and carry you further, than you might imagine.
  • Build On Top of Your Strengths.  Then — Add Layers.  We will close 100+ sponsors this year for Annual and Europa, but until Q4 of 2017, all of it was from inbound.  We just started to add outbound to sponsor sales in the fall of 2017.  But it did work — we closed $400k of outbound in just a few months.  This year, probably $1.5m-$2m will come from outbound.  But it took us time.  We were much better at inbound.  So building on our strengths (and not beating ourselves up where we were weaker) was key once again.
  • You Need To Materially Improve Every Year, And Probably Re-Boot Every 4-5 Years.  When we started doing content at meet-ups in 2014 and then the Annual in 2015, no one had ever done content and events like this.  But that was a long time ago.  Our 4th SaaStr Annual in 2018 represented the perfection of that formula — 5 amazing stages, 3+ days, with all the best speakers we wanted, tons of unicorns (CEOs of Slack, Atlassian, Box, Coupa, Blackline, Intercom, you name it) — and 60%+ women and multicultural speakers.  Now though, it’s time to reboot it.  We’ve moving on to mentorship as a key next frontier.  Now that there is so much amazing content out there (vs a dearth back in 2012-2014), we’ve more and more focused on enabling very high quality connections between attendees.  This is hard at scale, but it’s time to reboot things for the next 5 years. Once you’ve finally perfected your initial goal and formula … that’s probably the time to be rolling out the new one.
  • Bootstrapping Really is Different — At Least Until You Are At Scale.  In many ways, SaaStr is a bootstrapped business.  No outside capital, no salary taken by founder, etc.  In Year 5, we’re big enough now that the differences between bootstrapped and non-bootstrapped start to fade.  But you really do underinvest in a bootstrapped business, it really does take longer, and importantly, you tend to write off negative-margin and low margin revenue.   This is my first bootstrapping experience.  I have even more respect for it now.  It takes longer.
  • It Never Gets Easier.  But — You Get Better.  We wrote this SaaStr post a few years back on how it never really gets easier, and now I’m reliving it again.  Putting on the Annual actually isn’t easier this year than the last one.  It’s even harder each year in fact.  But now at least, we know.  We know what to do.  We know what works, what doesn’t, what the schedule should be, what resources we need.  We know how to make a great experience, what impacts that, what sponsors want, what speakers want, etc.  Going on Year 5, we have become experts in our little niche.  It’s no less work.  But we sweat strategy and execution more, and mysteries less.

And for the subset of you in events, a few key lessons in this micro-niche:

  • All that matters is the attendees, in the end.  If you have great attendees, the rest comes together.  Speakers will want to speak.  Sponsors will want to sponsor.  Etc. etc.  Those parts are hard, too.  But there are so, so many events in the world and in the Bay Area in particular.  The special part is getting a sizeable community to come together.  Figure that part out, and the rest will follow.
  • Dis-economies of scale are tough lessons to learn.  As events scale, they get more expensive per attendee.  This was a tough lesson to learn.  Multi-day events are far more expensive than single day events.  So stay single day as long as you can.  And beyond that, the bigger the venue, the more expensive everything gets, which is non-obvious.  Food + Beverage costs per attendee go way up — not down.  A/V costs go way up in bigger venues.  We spent $1,200,000 all-in on A/V for the 2018 Annual alone!!   Very few events get big enough to escape this valley of pain from low-cost 250-1,000 person events to larger events where you can get some scale (7,000+).  The valley in between is full of much higher costs without enough revenue to offset them.
  • NPS everything.  NPS your attendees, sponsors, speakers, everything.  Like any NPS, you will be surprised.  Easier events are easier to do well on.  Our first SaaStr Europa this year in Paris had our highest NPS ever.  But it was a relatively easy 1-day event to pull off for 1,600.
  • Domain experts are really hard to find in super-niches.  It’s hard enough to find domain expertise in general, but how many senior folks have experience running 10,000+ person, non-vendor events that can’t lose millions of dollars?  Not that many.  You have to give more here, in a super nichey space.  Events at scale are super-nichey.
  • Community first.  That’s your recurring revenue stream.  Attendees are all that matters, but it’s your community that drives it.  We don’t sell speaking slots (almost everyone does).  We don’t slot manels or boring sessions or vendor commercials.  We won’t put on anything we wouldn’t truly want to attend.  This is hard.  It’s much easier to do a cut-and-paste event.  But don’t.  Stay authentic.  And put community first.  If you do, you’ll actually have a recurring revenue stream.  For real.  We’ll have 750+ attendees this year that are on their 4th Annual, and probably 2,500+ returning from last year, maybe more.  And 70% of our sponsors renew year-after-year.  That’s not SaaS.  But it is revenue that nurtured and cared for, does renew.  In Year 5, and beyond.

See you in February at the biggest, best-est SaaStr Annual ever!  It’s just getting good in Year 5!!  And we’re already planning Years 6-10!

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