Venuebook

Kelsey Wrecked came up with the idea for Venuebook while planning nonprofit fundraisers, alumni events, and networking events in Chicago. She'd walk down streets of high-end bars and lounges asking if they'd host her fundraisers, frustrated by the lack of an easy way to discover and book venues. While venue managers loved the guaranteed revenue from private events, the discovery process was painfully manual. Kelsey realized this was a two-sided problem—but the solution wasn't obvious. She had never managed a venue herself, so she knew she had to learn from the source.

Moving to New York in the early days, Kelsey didn't immediately start building software. Instead, she offered to plan events for her friends—a deliberate strategy to get in front of as many venues as possible and understand their pain points. This immersive research revealed the real problem: venues were still using pen and paper calendars to manage availability. "You couldn't put up their availability in a marketplace because they were keeping their availability in a paper calendar behind the bar," she explained. This insight shaped everything that followed.

Kelsey recruited a developer from the Postgres database community who had experienced the same pain planning meetups. Together, they built the first version: online contracting, digital contract acceptance, basic CRM tools, reporting, and banquet execution orders. Critically, they designed the system with a strong data foundation from day one, tagging events and packages in ways that would later power sophisticated analytics and pricing recommendations—similar to how hotels and airlines manage revenue. "We built our software products. It's a very, very strong data foundation," Kelsey said. This wasn't just a booking tool; it was the infrastructure to transform an analog industry.

The first customers came from Kelsey's personal event-planning work. She found forward-thinking venue managers who embraced the digital-first vision—one of whom loved the product so much she eventually joined the company. These early adopters believed in the vision and provided the proof points Kelsey needed.

But scaling beyond this required overcoming a fundamental objection: venues feared losing the human touch and their negotiating power. "They really didn't want to adopt the transparency and collaboration because in many ways they felt that diminished their value as a venue manager," Kelsey recalled. She drew parallels to OpenTable's early days, when restaurants feared digital booking would eliminate their hostess stand—when actually it enhanced the experience.

Kelsey's solution was patience and density. She built marketplace liquidity methodically, targeting at least 100 venues per geography before launching the marketplace. "We focus on building density in neighborhoods and building density and price points that are typical event planners are looking for," she explained. Once she had critical mass, she turned on paid search.

AdWords became the unexpected growth lever. With an average ticket of $4,000–$5,000 and software fees of $1,200–$3,000 annually, the unit economics worked. But the insight was deeper: she ran ads targeting event planners searching for "private dining restaurants in New York" or "corporate event venues." These ads didn't just bring planners to the marketplace—they attracted venues who researched what their customers were looking for online. Both sides drove inbound interest.

Kelsey also introduced product tiering: a "light" version with basic booking and contracts, and a "pro" version with full system-of-record capabilities. This allowed risk-averse venues to taste the product before committing fully. "Once they start to understand our ecosystem and why we've built the software in the way that we have, they become very interested in using our pro software," she said.

But not everything worked. Kelsey fell victim to the "faster horse" problem early on. She listened too closely to customer feature requests and built complexity that actually hurt growth. The breakthrough came from digging deeper. When venues asked to send multiple proposals, Kelsey realized they really wanted event planners to compare and contrast options transparently. This insight led to "Express Book," which reduced inquiry-to-booking time by 80%, cut interactions by 80–85%, and increased conversion rates four to five times above industry averages.

Raising money proved harder than the product itself. Kelsey bootstrapped initially, sharing a desk with her first developer to save money. When she went out for a seed round in 2014, she had to pitch over 100 investors before getting her $2.2 million round. She credits angel investors like Joanne Wilson, who advised her to keep going, and her own resilience shaped by competitive figure skating—"when you fall, you have to get up and move on and make it look really easy."

The Series A, for $6.1 million, was faster because she had real numbers and a proven business. "One of the reasons why I spoke to so many investors with our seed round is that with the series, it was based on the type of investor we were speaking to," she reflected. Series A investors either said yes or no quickly, unlike smaller seed investors who dragged their feet.

By the time of this interview (roughly 2018, given the podcast references), Venuebook had just under 1,000 venues, nearly a million annual website visitors, and tens of millions of dollars in annual event request volume. Kelsey had learned hard lessons about hiring—wishing she'd brought on a recruiter earlier to avoid both overly senior and overly junior hiring mistakes. Her biggest insight: "It's all about the people."

Looking back at her 2010 launch, Kelsey's path was counterintuitive. Most founders would have rushed to build a marketplace. She did the harder thing: digitizing venues first, building data infrastructure second, and only then opening the two-sided network. Her key advice to other founders mirrors her own journey: understand your customer's real pain (not just their feature requests), be disciplined about critical mass, and when doors close, have more at bats. As she put it: "It literally takes just more at bats. That is one of my biggest pieces of advice to founders, that it's not actually easy to raise money."