SaaS Fundraising: 100 Investor Meetings for One Round

Omer (00:11.360)
Welcome to another episode of the SaaS Podcast.
I'm your host Omer Khan and this is the show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business.
In this episode, I talk to Kelsey Recht, the founder and CEO of VenueBook, a booking platform that connects event planners with venue managers.
Venue Book helps venues to manage their leads and bookings and market their space, and it helps event planners to easily find and book the right venue for their event.
Venue Book was founded in 2010 and is based in New York.
The company has raised over $9 million in fund to date.
Kelsey is a first time entrepreneur who came up with the idea for this business after experiencing the pain of finding venues and booking events herself.
And one of the smart things that she did in the early days wasn't to start building a software product right away, but by going out and talking to prospective customers in venues and learning more about their pains.
In fact, that's how she found her first few customers and even her first developer.
We also talk about raising money.
Although Kelsey's raised over $9 million, it hasn't been as easy as it may sound.
She started with a small family and friends round to get the business started, but raising a seed round was seriously hard work.
In fact, she had to go out and talk to over a hundred investors before she was able to get her seed round put together.
So we talk about the lessons she's learned there as a SaaS entrepreneur, as a first time founder, and as a female entrepreneur.
So I hope you enjoy the interview.
Kelsey, welcome to the show.

Guest (02:04.320)
Thanks for having me, Omar.

Omer (02:06.160)
Now I'd like to start by kind of my usual icebreaker question, just to find out what gets you out of bed every day.
So is there a favorite quote or in your own words, do you want to just share with us, like what drives or motivates you to get out of bed and work on your business every day?

Guest (02:19.760)
That's a really good question.
I actually heard a great quote by Winston Churchill the other day that I think embodies the way I think about the world.
Surprised I actually had never heard this one from him.
And I think it's very appropriate for startup founders, which is success is not final, failure is not fatal.
It is the courage to continue that counts.
And I think what's important about that is what gets me out of bed is that I evangelize in our industry a totally different way of thinking about the industry and to be able to inspire a very different change in industry landscape means a lot of testing and learning, a lot of small mini failures to get to that right success, but also lots of mini successes along the way overall.
And I thought that was a really, really good quote because I think of entrepreneurship as a series of experiments.
Some work, some don't.
And so it's continuing to push that ball up the hill that really kind of motivates me to wake up every day and do what I do.

Omer (03:20.300)
Great quote.
Tell us a little bit about VenueBook.
What does the product do?

Guest (03:25.660)
VenueBook is a way to find and book event spaces and book them online.
What we are truly is one of the only SaaS enabled marketplaces out there in the event venue world.
What I mean by that is that we make it very, very easy for event planners at companies to find and book event spaces by having availability, transparency in terms of pricing, instant quoting digital contracts.
But that is powered behind the scenes for some venues by a full system of record that becomes their catering and event management system and then by others with plugins to other systems out there.
And so a lot of people actually like to compare us to sort of the online travel agency equivalent in the meetings and event space.
And for those who don't understand that, it's obviously the OTAs like the Expedias, the Orbit's, the pricelines of the world that plug into the global distribution systems that exist out there for booking hotels and airlines.

Omer (04:30.770)
And you actually do more than that from what I understand, because you're actually powering a lot of the sort of the whole event functionality for these venues, right?

Guest (04:41.930)
Yes.
And so what we do is that for a lot of our venues we become what we call the full system of records.
So we are their full software system that they are doing all of their contracts through, they are managing their calendars, they are managing all of the back office things related to events such as what's happening on the day of the event, what menu does the kitchen have to prepare, what payments have been made, what payments have not been made, and also having amazing customer relationship management tools and also reporting so that they understand how their business is doing.
So we're also a full software system behind the scenes and that is actually what feeds the availability in our marketplace.
And we actually use the trends that we see in our marketplaces and the preferences from event planners booking those venues to actually optimize our software so that venues can make the most money possible off of their private events business.

Omer (05:39.300)
How do you make money?
What's your business model?

Guest (05:42.500)
We make money via two Revenue streams.
We make an annual software fee for our system of record, our operating system, and then we make a booking fee for any events that we send to the venues via our marketplace.
That book.
Got it.

Omer (05:57.860)
Okay, so you launched the business back in 2010.
How did you come up with the idea for venue book?

Guest (06:06.690)
So I came up with the idea for VenueBook because I was the person planning a lot of events.
I was planning a lot of nonprofit fundraisers, a lot of alumni events, a lot of networking events, and, you know, had that typical entrepreneur, there's got to be a better way to do this type mentality.
When I was living in Chicago at the time, and I basically remember walking down a street of sort of high end bars and lounges asking if they would host our fundraiser because there really was no easy way to find venues that were willing to do that.
And on the other side, those high end lounges loved having private event business because it was guaranteed revenue upfront deposits.
So it was a win win for both sides to do more private events.
But I realized it was very, very difficult to find and discover these venues.
But what's interesting is, as I really got into it, I realized that I had come from the event planning world and that I really had never been on the venue manager side of this world.
I'd never actually managed a restaurant, a bar, a club, been sort of a sales manager at a hotel for private events.
So one of the things I did early on was really to try to understand why those event spaces really had a lot of difficulty attracting private events and managing private events, which actually led us to build the software that we have today.
And that digital booking seemed like something that I wanted as an event planner booking that space.
But I realized quite simply, the venues themselves weren't digital.
So of course you couldn't digitally book them.
So you actually had to make them digital first.
So our early roots were just as a software company.
And within the last year and a half, we've really focused on ramping our marketplace and driving demand to the event venues on our software.
But our early days were that we actually had to first move the venue to digital and then start to allow event planners to book those venues digitally.

Omer (08:10.650)
Okay, so you've got the idea and you're kind of, you know, it's born from scratching your own itch.
What do you do next?
How did you kind of move forward with this idea?
Did you start going out and trying to talk to potential customers?
Did you start building a product?
What did you do?

Guest (08:29.700)
That's a great question.
So I had had some really good advice in the early days.
Sort of start small, but think big.
So the, the first year of the company, I actually, I had moved to New York City.
I had this idea, I basically told all of my friends, I will plan an event for you.
So do you need, if you need to do a networking event or a happy hour for your company, you need to do a private dinner, just let me know and I will find you the venue.
And the reason I did that is what I was trying to really understand is get in front of as many venues as possible and really do a lot of deep user research on why they had the problems that they have.
That is actually what led us to software first rather than a marketplace first, is that through that booking process I realized one of the reasons why I was having so much trouble booking these venues was because that these venues were doing everything with pen and paper.
I couldn't put up their availability in a marketplace because they were keeping their availability, you know, in a paper calendar behind the bar, for example.
That in the digital age was a little bit surprising to me, but it was that knowledge of sort of being very scrappy and almost being like a high volume event planner that actually taught me some of the lessons that became the foundation for what is now venue book.

Omer (09:43.910)
So how do you get into a business like that?
How do you go about building a software product when all the data that you need is stored on paper?

Guest (09:54.180)
That is a great question.
And what is interesting is that, for example, think about the way you book a hotel or an airline.
One of the reasons why it's so easy to book those transactions online is that those industries have been run on sophisticated software systems for years that have tracked pricing, tracked demand, tracked analytics.
And so one of our first steps was literally just get these venues onto a software system and then you can start to run analytics around how they price, how often are they booked, you know, what is the average response time, how long?
For example, if a venue spot responds within seven days, how likely are they to book the event?
The reason all of that is important is that to be able to drive digital booking in this space, you actually have to build the data set in the software platform to actually even understand what pricing you're going to show, what availability you're going to show when you recommend venues change their pricing.
And so in many ways, we are very much at the point in this industry of where people were sort of switching from travel agents to booking online and that they were starting to reveal these systems that were behind the scenes that travel agents were using and were allowing your average person traveling for business or pleasure to actually access that information and book it online.
Because in the end, venues to date have not necessarily thought about how do we create fixed prices that drive our capacity utilization up from 30% on average, up to 50.
What's the trade off between trying to negotiate somebody up to $10,000 when they have a $7,500 budget?
And so it's all of those analytics that we use to out of our booking platform to basically be understand how to give recommendations back to the venues both in our marketplace and across their whole business for the best way to drive their business overall.
And that it may seem really simple right now that a flight the day before Memorial Day is going to be a lot more expensive than a flight on a random Tuesday during the summer, for example.
But it's that sort of data foundation that's being built in this industry currently.
And so what we also did in the early days is knowing this about where the industry was going is we built our software products as a very, very strong data foundation.
So our software product actually under the hood can do a lot different things than the other sales and catering products out there.
And here's what I mean by that, is that if you look at other sales and catering platforms you have, you would say, for example, this is a three course meal that might just be a line item that's stored in that software system, but in our system we actually tag that as a very specific type of package, a very specific type of event, so that over time we can give analytics back to venues to say, okay, the average price of a three course meal at all of your competitors is $75.
You're priced at 90.
That's why you're losing business.
So there's all of these things that we do under the hood that don't necessarily show to venue managers right now, but we'll be able to provide our ability to actually really drive this industry into more of the revenue management and utilization optimization that you've seen in other industries like this, like hotels and airlines.

Omer (13:33.950)
So you're spending a lot of time not just enabling the bookings, but also trying to create a lot of structured data behind that in terms of the example that you gave.
So that over time you're going to get a much richer view of why one venue is more successful than another or is able to optimize the event better than a similar location somewhere else.

Guest (14:03.610)
Yes, A great example of this is that we have something in our product that we call an audit trail.
What an audit trail does is it tracks all of the interactions between the event planner and the the venue.
We can actually run analytics to say, I could tell you right now that on average, if you do not respond to an event planner within 24 hours, you have almost no probability of booking that business.
So we collect a lot of data points underneath to make sure that these venues are making a lot more money.
In other words, we don't want to generate PDF contracts, we want to be the truly digital enabled booking platform for them because that's where we really see this industry going.

Omer (14:43.820)
Okay, so let's go back to when you started out.
So you talked about this philosophy of start small, think big.
You had the idea, you said you're in New York and you start helping friends with bookings and that's giving you an exposure to learn more about the market and not just the booking side, but also understanding more about the venues and how they operate.
What was the next step?
How did you go about building the software product?
Did you raise money?
Did you find a developer who was willing to get you started?
What was the next step there?

Guest (15:20.950)
Well, part of the reason that I went out and planned all these events is that I wanted to meet a lot of venues.
Through that I met some very forward thinking venue managers who maybe were either using pen and pencil or were.
We're using catering and event management solutions, but not solutions that were designed to be interactive and collaborative from the start.
So I found a couple of amazing resources on the venue side of these things.
Actually one of our very first customers, she now works for us actually because she loved our product so much on the venue side.
And we basically used their pain points and modeled what we did off of some existing sales and catering solutions, while also building towards what we believed was a world of more interactivity between the event planner and the venue.
And what I mean by that is that instead of being able to just create a contract on the venue side, actually allowing that contract to be collaborative in a digital environment, such as choosing a menu, choosing a time.
So in other words, it was taking a lot of the models that existed, but building towards openness.
And at that time I also recruited a developer who was planning a lot of events for the postgres database community.
He came on in the early days to basically help us build out the platform because he'd had this problem himself.
He dealt with venues, trying to find locations for his meetups.
We were lucky to have first off, venues who were really forward thinking and really believed in what we were doing and a developer who was a phenomenal engineer that also understood the pain point that he was building to solve.

Omer (17:05.460)
Tell me about the first version of the product.
What did it do?
Because I'm sure it was very different from what you have now.

Guest (17:13.780)
The first version of the product had online contracting, online payments.
Actually the first version didn't even have online payments, I correct myself there.
But it had online contracting and the ability to share that contract digitally and accept, accept that contract digitally.
We had early customer relationship management tools such as an address book tracking of basically your best customers, all of their contacts, what company they're at.
We had basic reporting to tell the venue what, how their business was doing.
And then we had something in the events world that is called basically banquet execution order.
They're one of the sort of the what a venue lives and dies by.
Sort of, okay, I need 25 of this appetizer, I need 15 of this.
That is sort of what is basically to make sure the event runs smoothly.
What all of the operators at that venue have day of.
That was basically what we had in the early days.

Omer (18:12.770)
And so you talked about these sort of forward thinking venue managers or venues.
These were probably the easiest people to get on board because they kind of had a shared vision for what you wanted to do.
But tell me about beyond that.
When you went out and started talking to other venues to get them using this system, what were some of the objections that you started to hear?

Guest (18:40.760)
One of the things that we heard from that next wave of venues is a lot of venues really worried that they were going to lose that human touch and lose that ability to customize and cater to a client and lose what they they viewed as the ace in the hole of you call me and I build you something for your budget overall.
And so 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.
And it's interesting, I heard from many, many mentors of mine that were at OpenTable in the early days that a lot of restaurants also felt this about OpenTable, that they really felt, oh well, open table is going to get rid of the hostess stand.
And the hostess stand is so important for introducing people to our restaurant and our brand and our ethos.
And what they didn't realize, that OpenTable was actually a compliment to the people who sit at the front of the restaurant and greet you and provide that experience.
It wasn't a replacement.
And that's really how venue book functions, is that we're not a replacement for the human touch and that customization, we're an enhancement of it and that we actually make it easier to service the customers faster and in the way they want.
In terms of digitally enabled service, how

Omer (20:03.640)
many venues did you get on board before you felt like you had enough critical mass there to be able to offer some kind of marketplace?

Guest (20:17.480)
Yes.
So we believe that it takes at least 100 venues in every geography to have a critical mass overall.
And that's sort of the bare minimum.
So once we were over 100 in our core geographies, we really felt that we could turn on a marketplace.
And the reason is that venue inventory is not uniform.
And what I mean by that is that two restaurants, one might have a 50 person private room and one might have a 10 person private room.
And so to be able to service and provide enough selection to event planners, you do need more inventory because it's not as if every single venue we recruit is going to have a great private dining room for 20 people.
We focus on building density in neighborhoods and building density and price points that our typical event planners are looking for and building density in certain geographic areas.
So, for example, we'll say we need more venues in Chelsea.
We don't have enough selections in Chelsea.
And so we have a very targeted way too that we build our venue base to make sure we're adding enough selection for the event planners on the other side.

Omer (21:25.460)
One of the challenges of building any marketplace is the chicken and egg situation, right?
So you've got to have the venues, but you've also got to have the event bookers and you've got to be able to offer both of them something to get the flywheel sort of spinning with this marketplace.
So once you had enough of a critical mass of venues, what did you do to find event managers?

Guest (21:55.780)
So first off, we actually have very good natural SEO for our website because of the fact that we are a SaaS platform behind the scenes, which works to our advantage.
What we used is actually a lot of AdWords.
AdWords was really successful for us in the early days because we do have a high ticket.
And people are tending to search for event venues in Google in that for the people who do it, they might do a handful of events a year, but every time they're looking for the next new things.
So they're going into Google and they're googling private dining, restaurants, New York City, raw spaces, New York City.
And so we actually brought on some experts that had been at Google to actually build up our online marketing presence, build up our analytics, build up all of our tracking so we could really learn how to start driving demand to these venues.
The other thing that we did is that we do evangelize a slightly different way of booking.
That for some venue managers, they embrace it and some are not our early adopters.
So about a year and a half ago, we tiered our product.
We have two products.
We have sort of our entry level light product, which is basic booking tools, you know, simple contracts, online payments.
And then we have our more pro booking product, which is the much more powerful system of record.
And we actually use the light product as a gateway or taste of the way that we evangelize booking your event space, which then serves as the process for upgrading to our pro product.
So we also learned a different way to also help drive people into our way of booking.
And that what we find we hear from venues is that 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 R Pro software versus other tools.
Because R Pro software is built in a slightly different way than some of the other catering sales and catering products out there.
And that we're much more interactive, we're much more allowing the planner to self service, for example, we evangelize.
Every venue should have payment set up.
A lot of venues don't want to take digital payments, but we give them the stats to tell them you're actually going to book less business if you don't take digital payments.
Because for somebody to sign a contract digitally and then have to call you over the phone to give you your credit card, it's just friction.
And every time you put friction in a booking process, people are less likely to book.
And so tiering our product has actually been really successful in driving our ability to evangelize our different way of booking and our software system.
Because people can get a taste of it and then decide to roll it out across their whole business.

Omer (24:46.340)
Tell me a little bit more about what you did with AdWords and how you figured that out.
Because often I hear from a lot of SaaS founders is that they haven't been able to get AdWords to work for them.
And so you mentioned that you have a high ticket.
Well, first of all, tell me what that means and is there a number that you can share with us there?

Guest (25:06.740)
So our average ticket for in our Marketplace is about 4 to $5,000 and our software costs a couple of thousand dollars a year.
So anywhere from $1,200 up into the $3,000 range annually.
And one of the reasons why I believe we've been able to get AdWords to work for us is that once we started to have a certain level of venue saturation in a market, we turned on the marketplace.
And the marketplace actually drives the inbound venue requests.
Because almost any business needs more, is always willing to do more business.
Not every business necessarily needs an operational tool.
And so we use our AdWords dollars to drive event planners to our website, which in turn drives venues to our website.
Because actually, when venues go out there looking for solutions, they often try to figure out, what are the event planners looking for?
What are my customers looking for?
What do they find valuable?
So we have found by using our AdWords to attract event planners and business into our marketplace, that has actually attracted venues to our software platform.

Omer (26:20.330)
So what kind of keywords are you trying to target?
Is there an example you can share?

Guest (26:25.290)
So that would be, for example, event venues, corporate events, private party spaces, meeting spaces.
Sort of think about what you would do if you were looking for an event space and you didn't really know where to start.
What would you type into?
Google.

Omer (26:41.660)
Got it.
So you're doing that because event bookers may not necessarily be looking for an online place to book, but they are looking to figure out what are the best venues for them or for their event.

Guest (26:56.620)
Yes.

Omer (26:57.060)
And then, as you said from, if I understood this correctly, that the venues are also trying to figure out, okay, how do I get more business?
And part of that research is looking up those kinds of keywords to figure out what the event planners are doing online.
And both of those are helping to drive traffic to venuebook.com, both from a buyer and a seller side.

Guest (27:24.650)
Yes, exactly.
And we do have an inside sales team that then educates the venues, provides demos to them.
But we get a lot of inbound interest actually, based on the AdWords that we are running for event planners.

Omer (27:39.230)
So I believe you've raised over $9 million so far.

Guest (27:45.070)
Yes.

Omer (27:46.350)
When did you decide to raise money?
When did you feel like you had the business had enough traction to be able to go and find investors?

Guest (27:56.050)
It's a great question.
In the early days, we really bootstrapped the company.
Overall.
We raised a very, very small friends and family round to build out the software, have a very small team.
Our early developer and I, we actually literally used to share a desk.
We sat at one of these desks that was meant for one person, basically right next to each other to save money.
And we raised our first seed round in 2014.
When we felt we had pretty good product market fit in terms of the software system and had learned the early lessons of how to sell the product and what attracted venues to the product.
So we used our seed round to really, really focus on learning how to drive a lot more venues and hiring more salespeople.
And then we raised our Series A when we felt that we were getting to the critical mass we needed in key geographies.
And our Series A was designed to drive more of the marketplace and really have the marketing dollars to be able to drive traffic inbound to venuebook.com and really grow the business in a faster way.

Omer (29:11.590)
So you're a first time founder and so this is probably the first time you were going through the process of raising money.
What do you wish you had known about raising money before you started out?

Guest (29:25.030)
First off, we have been lucky to raise a big chunk of money, but I also believe it is just really hard to raise money.
So even though we've been able to raise a reasonable amount of capital, it takes a lot of calls, it takes a lot of nos.
It's a numbers game.
And I wish somebody had told me that the stories you read about in TechCrunch where people have 30 or 40 competing term sheets, is not actually the typical way that it is.
Because for example, to get our seed round, I think I talked to at least 100 investors to be able to get that seed round.
And we were lucky enough that our Series A was a lot easier to raise.
But just like being an entrepreneur, it literally takes just more at bats, as I like to say.
And that is one of my biggest pieces of advice to founders, that it's not actually easy to raise money.
So even the people who've been able to raise big sums of money, it's often not very easy.
The other thing that I would say is I know there's obviously a lot of talk about being a female founder and the difficulty of raising not as a female founder.
I believe that one of the things is when you pitch a company you have to go in with that just blind confidence and the focus on what is the sale I'm doing today and be very confident in your business.
Because I think one of the things that is the path to raising money is that the investors are looking for you to take a stance and have a vision.
In my early days I went in asking for a lot of advice because I'd assumed that these investors had, they'd been in the business for a while and I found that then they missed sort of my conviction and the way that I was striving to build this company, what we found actually is by going in and being less compromising about my vision, we've actually had more success in terms of raising money because in the end, they want the entrepreneur to be really passionate about what they do, and they're either going to buy into your view of the industry or not.
And if you're in the first meeting already getting advice on a completely different way of doing things, they're probably not the right investor for you.

Omer (31:38.140)
How much money did you raise on the seed round?

Guest (31:41.820)
We raised $2.2 million.

Omer (31:44.380)
Got it.
And what kept you going?
I'm curious.
I mean, 100 going and talking to 100 investors is a big number, and a lot of us would have probably given up sooner.
What kept you going and what else did you sort of, you know, you talked a little bit about some of the things you learned from that.
But maybe for somebody who is in a similar situation and hasn't had some luck yet raising money, when talking to investors, what advice would you give them?

Guest (32:15.070)
Well, first off, I do think the seed round is always the hardest round to raise because you're definitely selling a little bit more on a Hope and a Dream.
And I believe I had to go to a lot of investors because I probably wasn't.
I didn't know perfectly how to sell that hope in a dream in the early days.
The other thing is I end up getting a couple of very, very strong angel investors in our Friends and Family Angel Round One.
Who's still on our board, Joanne Wilson.
She's really well known in the New York City investment community, who really gave me the support to keep going and sort of said, just keep getting out there.
Keep getting out there.
Your business is really starting to take off.
Like, don't be discouraged because keep focusing on moving the business and the rest comes from it overall.
And so I was also lucky to be surrounded by people who gave me the strength to keep going generally.
But I think that's sort of being an entrepreneur sometimes.
It's just that it's like getting up, like when you've done something that's not perfect, just like standing up, brushing yourself off and moving forward.
That doesn't mean I'd want to go through it again.

Omer (33:24.110)
Yeah, totally.
What about the Series A round?
How much did you raise there?

Guest (33:30.190)
We raised a little over 6 million.

Omer (33:32.750)
And how was that experience?
Did you have to talk to as many people?

Guest (33:37.310)
I did not have to speak to as many people.
One of the things about the Series A Is that you start to have real numbers and you start to have more of a business, which makes it an easier round to raise.
I also found that 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 and that often smaller investors, you need a lot of them.
So they'll sort of.
They'll drag their feet is the best way to put it, Waiting to see how a round comes together.
Whereas what I found with series A investors, they either said yes or no very quickly, so you could move on very quickly.
So it was much more of an efficient process.

Omer (34:18.249)
Okay, so we talked about the effectiveness of AdWords and how you made that that helped you attract both buyers and sellers or event bookers and venue managers.
You talked about the tiered product and how that's helped you and enabled some growth there.
What were some things that you tried in terms of growth that didn't work?

Guest (34:40.729)
In the early days of the product, we, as I said, we evangelized a different way of booking.
One of the things that you hear all the time is listen to your customers, listen to your customers, do customer research.
And we found that in the middle life cycle of the product, we went out and we collected a lot of customer feedback from venues and we built some things into the product that actually they hurt our growth.
And what I mean by that is that we almost listened a little too closely for our customer to our customers.
So we fell victim to the faster horse problem where they asked for complexity and customization and then kind of came back and said, well, this is too complex and too customizable.
And so I do feel that at some point when we didn't find the right mix of what does the customer tell you that they want versus what do they really need that held back our growth?
So that what we've really started to do in terms of our product development is that what's that real pain point and what does that actually mean for the product?
Not necessarily taking venues product requests right at their word, but really trying to understand that unmet need and building a product around it.
That actually is what led to our pretty game changing feature that we call ExpressBook.
ExpressBook is basically a way for an event planner to tell the venue exactly what they want and then the venue just needs to approve it.
And what we were hearing from a lot of venues is that a lot of my leads are unqualified.
Can I send them multiple quotes?
Can I send them ways to compare and contrast and what we realized is that it's not that you actually want to send multiple proposals or quotes to the event planner, it's that you want to allow the event planner to compare and contrast different event setups to understand what meets their need and what meets their budget.
So we actually flipped that on its head to build what is now exp book, which has seen huge success in that it takes down the time from inquiry to booking by 80% and it takes down the number of interactions.
I think it's about 80 to 85% that it takes to actually take an inquiry to a booking.
And also it increases the average inquiry to booking conversion rate by about four to five times above industry averages.
And so in the early days, we probably listened a little too closely for an exact ask from our venues and that hurt our growth because we built some features that were a little hard to use and wasn't actually what they really wanted.
And we've done a much better job of really doing user research around that unmet need and building product around it overall.

Omer (37:26.970)
So that's a really good example.
So did you initially, when you heard that they wanted to be able to send multiple proposals, was that the feature that you initially decided to build?

Guest (37:37.810)
That was actually the feature that we considered building.
We actually considered allowing venues to be able to send out multiple proposals, as I said, because they wanted to show options.
What ended up coming from that and really studying the interaction was that the reason they're doing that is that the event planners didn't have the transparency and the tools they needed to actually compare and contrast.
And going back to this, that we're a data driven system is that we actually studied the interactions and the messaging and the back and forth between event planners and venues for a couple of months to realize that what was happening is that in many ways people wanted to sort of be able to have that similar to what you have in Kayak where you compare, okay, what's the cost of a direct flight?
What's the cost of making two stops, three stops?
And that is ended up what we built.
And I'll tell you, some venue managers were a little bit hesitant about expressbook in the early days.
What we find though, it's a very experiential product that once they've experienced it, they call us back and they say, wow, that was amazing.
I was a little bit skeptical, but that was just so easy.
It just made it so much easier to book this event.
So in many ways we kind of turn their request a little bit on its head to a Lot of good success.

Omer (39:03.170)
Looking back, you've been in business for, I guess about what, eight years now.
What are some of the other harder lessons that you've learned along the way that you wish maybe you could have done differently?

Guest (39:14.450)
It's all about the people.
I know that is what probably a lot of entrepreneurs say.
But my biggest mistakes have been hiring mistakes, hiring people that were potentially too senior for the business, having junior people on staff when I needed to hire a more senior person to manage them.
And looking back, one of the number one things I would definitely do is I would rehire recruiter from the start.
And, you know, I think based on my early bootstrapping days where I had no capital ever, I was very hesitant to spend money once we actually got money.
And somebody who really understands recruiting, interviewing, finding the right candidates, really identifying the job needs I think would have served, would have been very valuable in the early days.
I've sort of learned that through the school of hard knocks.
But I wish I'd had a better mentor along the way to really teach me how to hire in a really clear, smart way.

Omer (40:11.550)
Can you maybe share some numbers with us?
Like, I don't know if you talk about revenue, but are there other some numbers that you can share just to give us a sense of the size of the business?

Guest (40:20.110)
Yes.
So we have just under a thousand venues overall.
We get a ton of demand.
We have almost a million visitors a year to the website, and we get in the tens of millions of dollars in terms of demand and event requests coming into the business.
We don't share exact revenue numbers.
But what I will say is that event planners, especially in the corporate world, are voting with their feet that they like a different way of booking event venues in the way that venue book has to offer.

Omer (40:49.530)
Got it.
Okay, let's get onto the lightning round.
I'm going to ask you a series of questions and just try to answer them as quickly as you can.

Guest (40:56.810)
Okay?

Omer (40:57.410)
All right.
What's the best piece of business advice that you've ever received as a founder?

Guest (41:03.570)
Only probably you should follow the 8020 rule.
80% of what you do is probably wrong.
20% is probably right.
Double down on the 20% and don't worry about getting the 80% wrong.

Omer (41:15.840)
What book would you recommend to our audience and why?

Guest (41:19.120)
The Hard Thing About Hard Things.
I love that book.
It's such a realistic portrayal of what it's really like to run a company and sometimes the really hard decisions that you have to make as a founder.

Omer (41:30.880)
What's one attribute or characteristic in your mind of a successful entrepreneur.

Guest (41:36.880)
I think it goes back to that Winston Churchill quote I gave you at the start, which is sometimes it's, it's just about getting up and like having more at bats overall because you are going to experience failures.
That's part of the process overall of building something that's truly game changing.

Omer (41:54.620)
What's your favorite personal productivity tool or habit?

Guest (41:59.260)
Evernote, for sure, it's my digital memory.
It's just like because I'm doing eight different types of things and eight different types of functions, I have to write everything down and put everything in Evernote because it becomes my, becomes my repository of memories when I need to pull out something from a sales call, you know, three years ago.
Right.

Omer (42:20.470)
What's a new or crazy business idea you'd love to pursue if you had the extra time?

Guest (42:25.110)
So I have two kids.
I would say something probably in the very interesting children's activity space and indoor spaces, especially here in New York City, kids go crazy in the middle of the winter and all the places are the same.
There's probably a big business there and thinking a little bit outside the box.
Parents don't have any time and they're willing to spend a lot of money overall to get out of their tiny apartments.

Omer (42:53.209)
What's an interesting or fun fact about you that most people don't know?

Guest (42:57.930)
So interestingly, I was a competitive figure skater growing up especially think in light of the Olympics just ending and people watching more figure skating than they've ever seen.
What I find interesting about figure skating is probably a great analogy for being an entrepreneur because you're really out there alone in the spotlight and when you fall, you have to get up and move on and make it look something that's really, really hard and physically demanding look really easy.
It's very akin to the whole overnight success that people think of as people as entrepreneurs.
You're an overnight success in five years, for example.

Omer (43:33.020)
Yeah.
And finally, what is one of your most important passions outside of your work?

Guest (43:39.580)
I would say just hanging with my family.
I don't have a lot of time for lots of things, so I prioritize.
I spend all of my time basically working and seeing my family.

Omer (43:50.460)
Awesome.
Kelsey, thanks for joining me today and sharing your story and your insights about building venue book.
If people want to find out more about the business, they can go to venuebook.com and if people want to get in touch with you, what's the best way for them to do that?

Guest (44:10.140)
They can email me.
As a founder, it's very simple.
It's just Kelseyenubook.com awesome.

Omer (44:16.300)
Thanks again and I wish you all the best.

Guest (44:18.620)
Thank you.

Omer (44:19.420)
Cheers.