SaaStr

Jason Lemkin started SaaStr in 2015 as a simple idea: bring together SaaS founders and leaders to share real metrics and learn from each other. He organized the first event in the Regency ballroom in San Francisco with just a tweet saying "come to SaaStr annual." There was no other annual SaaS conference at the time, and Lemkin invested approximately $200k to produce what became an intimate one-day event with 800 attendees. He brought in early heavyweights like Aaron Levy (Box), Stuart Butterfield (Slack), and David Sacks, creating immediate credibility. The event broke even, which Lemkin considered a success given the experimental nature.

After the first event's success, Lemkin outsourced operations to Max Altshuler (who ran Sales Hacker), allowing himself to focus on speakers, content, and marketing while Max handled logistics and kept all revenue. This partnership was crucial—it freed Lemkin to do what he did best: curate speakers and build community. The second year exploded in scale, growing to 2,700 attendees and generating $3.6M in revenue (split roughly 50/50 between tickets and sponsorships). However, this rapid scaling created chaos. Lemkin didn't know event production, AV, catering, or vendor management, and he made critical mistakes by hiring mediocre people who lied about deliverables. He discovered that in events, you can't slip dates like you can in software—lies from poor event managers cost him $10M when a booking fell through in March 2020.

Growth in the early years was entirely word-of-mouth. Lemkin didn't have a mailing list; he relied on blog posts and tweets. The market for SaaS knowledge was hungry—there was no content, no precedent for VPs of sales or CEOs sharing vulnerably about their businesses. The first attendees came because they were curious and wanted access to peers. By 2015-2016, this was novel enough to drive attendance without paid acquisition. However, as the world became more sophisticated and SaaS content proliferated, Lemkin had to systematize. Today, 90% of ticket revenue comes from a single CTA email sent to his curated list of 120,000 people. Price-increase emails work best; discounts don't. He sends two emails per month and half of all annual revenue comes in the last 60 days before the event.

What worked: Email remains the dominant growth channel. Lemkin invested deeply in understanding what drives conversions—urgency (price increases) beats promotions, and simple, single-CTA emails outperform complex multi-touch campaigns with embedded links or images. Building a small, curated community of 120,000 high-intent people proved more valuable than a massive, diluted list.

What didn't work: Trying to scale events without understanding the function. Lemkin hired full-time event managers, production companies, and coordinators who underperformed, lied about deliverables, or quit under pressure. He eventually learned he had to go deep into the operational details—learning AV, catering, vendor management—to spot problems early. He settled on embedded agency partners: Cred PR handles speaker recruitment, and Montgomery Entertainment produces the event. Finding these partners took years of trial and error (one fired him, two quit, one backed out after due diligence).

The business model evolved as it scaled. Year one and two revenue came 50/50 from tickets and sponsors. Today, it's roughly 20% tickets ($5M), 8% sponsorships via media/newsletters ($2M), and 80% from event sponsors ($20M). This shift happens naturally as an event becomes the must-attend venue in its category—vendors stop negotiating and just allocate budget to be there.

SaaStr generates $25M in ARR with only 10 full-time employees (5 sales, 5 marketing/ops), achieving exceptional revenue-per-employee metrics. The 2022 event had 10,000 attendees and featured 250 speakers and 500+ "brain dates" (mentorship sessions). Lemkin runs a lean, profitable operation by outsourcing specialized functions to embedded agencies rather than hiring full-time staff. He's rejected acquisition offers (e.g., $180M from Chargebee) because the team loves the work and he still has energy to build. His next goals are to grow from $25M to $100M while maintaining quality and community integrity. He deliberately rejects speakers who won't share revenue and profit data, trading scale for curation. Lemkin also started Founder Path (a separate media business of 30+ interviews weekly) to amplify founder narratives, though he recognizes the challenge of scaling creator-led businesses beyond one person's capacity.