#121 Ride iQ: Peloton for Horses

Erica: Pitch 3, day 2 [clap]

Peloton turned cycling into a $1.5 billion dollar business. Strava did the same thing for running. And one of the most successful startups to appear on our show, is Fight Camp. They made a huge business out of a tech enabled punching bag.

On today’s show, the Peloton for horses. Well, for equestrians actually.

But one of these sports is not like the others. To get started with horseback riding…you to have to…buy a horse, get a coach, and a stable?! But running on the other hand is… free. Just about anyone can go outside and run if they want to. 

So the equestrian market - it’s way smaller. But it’s full of passionate riders. Is passion enough to make horseback riding the next billion dollar business?

Will the VC’s see their next shiny unicorn, or will they just… see a horse.

I’m Josh Muccio, welcome to The Pitch, where real entrepreneurs, pitch real investors, for real money.

Hey everyone, I’m Beck Bamberger, managing partner of Bad Ideas group

Hi, I’m Al Bsharah, the managing partner at Interlock Capital

Hi, I’m Jillian Manus, managing partner of Structure Capital

I’m Howie Diamond, managing partner of Pure Ventures

The pitch for RideIQ is coming up AFTER THIS. Giddyup! [neigh] And if you want to watch the video of this pitch, go to pitch.show/youtube. Episodes premiere on Wednesdays at 7pm eastern.

[hellos]

Beck: Hello ladies. I'm Beck. Nice to meet you.

Al: Hi Kinsey. Al. No worries. Al.

Jessa: Hi Al. Jessa.

Jillian: Hi. Kinsey? Hey Jessa.

Jessa: You must be Jillian.

Jillian: I'm Jillian. 

Kinsey: Hi. I'm Kinsey Lux.

Jessa: And I'm Jessa Lux. 

Kinsey: We're sisters, co-founders, recent Tech Stars grads, and former upper level equestrians. Prior to RideIQ, I was a senior investment associate at Blackstone. 

Jessa: And my background is in marketing and community building. My experience as a rider includes winning a gold medal at the Junior Olympics. 

Kinsey: I was 13 when I moved from Minnesota to Florida alone so I could learn from an Olympic coach. I made that sacrifice, but I was still riding without a coach most of the time. Eight million equestrians ride without a coach for four out of five weekly rides. Those solo rides are astoundingly unproductive.

Jessa: And that's why we built RideIQ. RideIQ is a mobile app with on-demand listen-while-you-train audio lessons, taught by the world's best coaches. Open the app, choose a lesson, press play, and you have an Olympic coach in your ear guiding you for every step. We launched in August of 2021, and have organically grown to over 1500 paying members and $430,000 in ARR. 

Kinsey: 8 million equestrians paying $30 a month for RideIQ equates to a $3 billion TAM. And that's just with our launch product. The TAM is north of $20 billion when we expand across three other verticals. RideIQ is bringing world class coaching to every athlete, and we will drive a new era of athletic performance. We're kicking off a fundraise of $1.5 million, and are looking for partners who share this vision. 

Beck: Okay.

Howie: Great. Interesting. 

Jillian: So this is only audio.

Jessa: Correct. So this really gives them the guidance they need to make progress between in-person lessons, but it doesn't replace having your in-person lessons.

Al: So can we talk more about the market size. I think you said like 8 million equestrians out there. Does that include like people that aren't really competitive, they don't care about the training, they just like riding? Like, what does that number actually include? 

Kinsey: That includes riders who ride consistently. So those are your riders who are riding four to five times per week. That said, it's not necessarily only your competitive riders. Your competition riders are definitely a big portion of that whole demographic, but there's a lot of riders who really just do it because they're passionate about it and they have the horse in their backyard or they just enjoy doing it, but they still want to develop with their horse.

Beck: But that's 8 million in the US? 8 million globally?

Kinsey: That's global. Yeah.

Beck: Okay. It's global. Okay.

Al: And so of those, have you done the research to figure out like how many of them actually want training to go along with it?

Kinsey: Yeah. I mean, based off of the customers we talk to, the users in the market, I mean everybody is looking to improve. We have a user who she's an 89 year old woman who she loves to go trail riding with her friend, but she's a paying user of RideIQ because when she's not trail riding with her friend, she wants to develop with her horse and she wants to learn something. Our users, they coin themselves horse nerds, and there's always an opportunity to educate yourself. And for $30 a month, I mean, it's a really small subset of what they're already paying. 

Al: How long have you had your customers? And do you have anything on retention and -

Kinsey: Yeah. We launched in August of 2021. Our one month retention is 84%, our three month retention is 67%, and our 12 month retention is 42%. And I'll note that normal consumer apps that are subscription based, um the 12 month retention is 21% is the median. So we are double that. 

Howie: I like that you've experienced the problem first hand and you really deeply understand, it seems like, the customer journey, because you've been on it yourself. But just educate us a little bit on like, is there a general playbook for success or like general best practices for each of these disciplines? 

Kinsey: So the way that we're thinking about our coaches is we have very strict criteria that we recruit coaches under, and our number one priority is that they have a history and a reputation of proper horsemanship. And we wanna make sure that the information that they're putting out there is accurate and it puts the horse first. So it's a very compassionate approach. And then two is do they have a proven record of producing riders, and then as themselves as a rider. A lot of our coaches are celebrities in their own right because they have that proven record, they have decades under their belt of being successful in these sports. I mean, there's a reason that the oldest Olympians every summer Olympics are the equestrians. Because it really takes decades in order to become an expert, and that's why these - having access to the best coaches, is just like absolutely so valuable. 

Beck: Where's the research or where's the conviction around audio learning, And I'll give you an example. I do krav maga and I do group classes, which are fine. That's great, that's fun, it's super social. But then I do one-on-one, and my instructor yesterday was just saying, oh, you're a visual learner. I show you exactly this, you do it exact. And it's also someone who's yelling at you one-on-one. You can't hide. So it's very impactful. So where do you think on the audio learning and how does that sit into this - to someone who might say, no, I need a coach who's right next to me or with me on the horse. I don't even know how the coaching happens. So where does that fit? 

Kinsey: So the real value of audio for horseback riders is during the activity. So it meets you where you are when you need it most, which is when you're in the saddle. And the way that we think about the effectiveness of audio is we hear from our members, they are never more focused than when they're listening to these lessons. you channel in, you're not thinking about that meeting that you had 30 minutes ago, you're not thinking about what you have to do after your ride. You are focused. And they are saying that they get the best rides out of their horses when they have audio lessons in their ear. And then the phase 2 of RideIQ is having a video support for every audio lesson. So before you get on and take this audio lesson, watch this 2-minute video. You can see the coach doing it. It can make visual learners feel safe, because that's what we want. It's obviously - it's gonna be a higher cost to roll that out, but we're at that stage of the business. 

Al: What did it cost you to get the recordings done, getting them put into the app?

Kinsey: Yeah, so it's $100 on average per lesson. 

Beck: That's it? Wait, that sounds exceptionally cheap. 

Jessa: It is exceptionally cheap and that is the natural response to that. We pay the coaches $100 per lesson that they record. It could be a nine-minute lesson or a 45-minute lesson, it doesn't matter to us. Our coaches record their lessons while they're on their own horse. And we tested every way that a coach could approach these audio lessons. They could record from the ground watching somebody, they could record with a lesson plan in front of them, or they could record on the horse, and we tested that with our test riders ahead of time. Every person said they prefer it on the horse and they enjoy the experience. They feel like the coach is in their head while they're riding.

Al: They're on the back riding with them.

Beck: I get it.

Jessa: And they tell us things all the time. Like when that hor - when the coach's horse blew air out of its nose and relaxed, my horse did that in the same moment. And those are such cool experiences, especially given that this is a solo sport, so it can be lonely, and when you have someone there with you, and you're starting to feel like friends with these celebrities, it's a cool experience. But that's why we're able to pay $100, because it just makes it so that they can make $100 more than they otherwise would on that ride. 

Howie: They record one lesson, that's $100. Not how many times a lesson has been played back.

Kinsey: Correct. 

Jessa: We're scrappy, you guys.

[laughter] 

Howie: - I'm struggling with like - price is an indicator of quality and to get the best coaches, are these the best coaches that are just asking for $100?

Jessa: We have one Olympic gold medalist, several Olympic medalists, six Olympians. All of them have competed to the top of the sport. We're not making any sacrifice whatsoever in terms of quality. Like, What you're saying is the nature of the equestrian market. Unfortunately, people who are top equestrian athletes, they're still kind of living paycheck to paycheck. Like, it doesn't have a financial model that can support these people in the way they should.

Howie: See, there's something really interesting with that. Because there are amazing coaches in every sport that aren't quote unquote famous. But they're professional, at the highest level, and they're only getting paid for the coaching they're doing one-on-one. And so there's something really interesting with that gap in the market on the coaching market that you can come in and incentivize them to work with you at a scale that they've never experienced, and for the world to be able to utilize their expertise. 

Beck: How long is the focus on horses? Cos I'm thinking in the billion dollar of like, oh, this is new, audio learning. This is the next master class in audio. So for example, I fly helicopters, I'm like, oh, I could be listening to a flight thing. Like level to the - So I'm seeing it in multiple applications, but I wonder, I'm asking, are you just horses?

Kinsey: I don't think - I think that would be selling the business short, it's selling the vision short.

Beck: Yeah.

Kinsey: There - there is so much opportunity within equestrian. if we capture 5% of the equestrian market, that's 100 million in revenue. But we see -

Beck: I see that.

Kinsey: - there's so much value to expand this to other sports. Every time we talk to someone, they're like, wow, I'm a golfer, when can you do golfing, or I'm a skier, when can you do skiing. And so we do see the value there. And we just wanna make sure that we're doing it in a very methodical way where we don't risk underselling our equestrian endeavors. 

Howie: What level of scale, engagement, revenue do you feel like you need to get to before you would want to expand? 

Kinsey: For me, it's really a matter of having expanded to all the disciplines that we want to address within equestrian. We're already in the process of expanding to two more disciplines in the next couple months, and then we are getting more requests for western disciplines every day.

Howie: So how many disciplines are there total?

Jillian: Eight.

Kinsey: There's like - there's like 15 really.

Jillian: Did you say 15? Oh yeah, 15.

Kinsey: English and western disciplines are like kind of two different sides of a coin. And right now we are primarily focused on English disciplines. And so right - we're expanding within English and then we're gonna expand within western. And I think once we feel like we're on that path, that's when we start to do the customer discovery in these other markets to understand where do we go next. 

Al: So curious on the raise. One and a half million. How far along are you? Have you set terms? 

Kinsey: We're really just starting the conversations with this pitch, so it's a good launching point, hopefully. And then we're targeting 10 million post, um ideally on a safe, but we're flexible on that front. 

Al: One and a-half million, at what point does it achieve what goals? 

Kinsey: Yeah. So ideally, in the next 12 months, we'd like to hit 2 million in ARR, um and then in the next 3 years, we want to hit over 5 million.

Jillian: And where are you in ARR now? Sorry.

Kinsey: 430k. 

Al: I never thought I would say this, but I might be interested in investing in an equestrian company.

Beck: Yeah, Al.

Al: So yeah, I'm relatively comfortable at 50k. So.

Kinsey: That's be great. We'd love to have you on board. 

Howie: I love the scrappiness of you two. You guys clearly know the equestrian market really well. Like, in a deep deep level and the customer problem and everything that you're solving for that. I get concerned about expanding outside of that. Is it just gonna be a natural easy evolution into these other markets and speaking the lingo and knowing the customers with these other sports. And then just the revenue projections, you know, a three year 5 million ARR doesn't make me super excited either. I would really want to see you get to 2 to 3 million in ARR within the equestrian sector, and then one expansion out of the equestrian sector into another sport and then I'm gonna be in. But for right now, I'm out 

Kinsey: We'll keep your number.

Beck: I agree on that. I have the same concerns To get to Howie's point, where are those other ones that are as sticky and small as horse -

Jillian: Fly fishing.

Beck: Fly fishing, golfing -

Howie: That's so random.

Jillian: I mean -

Beck: But let's hear it from them. I wanna hear like where do you see that?

Jessa: Some of the verticals that we're excited about would be things like boxing or gymnastics. I also don't want to rule out activities, like photography or physical therapy. There's a lot of opportunity for audio lessons. We don't have a lack of conviction in these other verticals, but we certainly have less testing that's been done.

Beck: Sure.

Jessa: We feel a lot of conviction and product market fit in our current equestrian market. I mean, I would encourage you guys to look up reviews on social media or in the app store of RideIQ. The word 'gamechanger' is used over and over. They're glowing reviews. Seven of our members have RideIQ slogan tattooed on their body. 

Al: Wait, how many?

Kinsey: Seven.

Al: Holy cow.

Kinsey: It's a - yeah. I mean -

Beck: Permanent tattoos?

Kinsey: Yes.

Howie: It's, It's fanatical.

Kinsey: It's a passionate user base. 

Beck: to use an analogy, like, with the kind of like the horse blinders. I think you're too horse-focused. Because, and that's why I'm a pass for now, I would wanna hear, listen, audio learning is about to take off. Now, we have found this first market, which we know deeply about, so we're gonna own that market, and then here are the next five ones so I can paint you the picture of how this is a multi-billion dollar company. That's what I would want to see. 

Jillian: See, I disagree with you and Howie. 

Al: Let's do this.

Jillian: Okay.

Beck: Let's do it. 

Jillian: You're missing the point here. The point is a very, very active engaged entry point. You know this market cold. I don't want you to think about any other market right now, because if you do this well, you can take every strategy that you're gonna learn from this, and bring it to another fanatical market. 

Beck: So are you in?

Jillian: Yes, I am in.

Beck: Oh. Okay. There we go. 

Jillian: I want you to crush this. I'm in for 50k. 

Josh: Are you good on those terms? 

Jillian: I'm a little uncomfortable with 10 post. 

Al: Yeah. I wasn't totally comfortable with it. 

Howie: Cos you're - that's - you're basically 10 x over revenue right now and that's -

Jillian: That's not palatable to me.

Howie: That is very high.

Kinsey: What valuation do you feel like is appropriate? 

Howie: Six million. I'll just tell you. It's six million.

Jillian: Yeah. 

Kinsey: Jillian we'd love to have you on the team. So, well, if it works for you guys, do we go into diligence, have these conversations and then take it from there? Does that work?

Jillian: Yes.

Jillian: That's how it works.

Howie: There's a contingency on Jillian's investment, though. You have to teach her how to ride a horse.

Kinsey: Easy.

Jillian: let's gallop here. 

Kinsey: I love that. Well, thank you guys so much for your time. This was a blast.

[thank yous] 

Jillian: You guys are morons. 

Howie: They'll take our money in a year and a-half from now.

Jillian: Maybe not because -

Howie: They will. Trust me.

Jillian: Well, maybe I won't let them.

Howie: Oh, okay. You're gonna block them from taking our money?

Jillian: Yeah.

Howie: All right, I'll block you in the next deal.

Jillian: Okay, fine.

Howie: Fine. 

Jillian: Okay. Well, that's on the record.

Al: One of the things that I was super excited about with these two is early 2000s I was big into four-wheeling. I started a website called Jeepaholics, it was this ridiculous community, we had like millions of page views every month. I didn't know what the heck I was doing with the business, and I was a solo founder. I made all the mistakes. um But I had this ridiculously passionate group of people. And they're on the inside, they have this thing - I just - at this stage, it's very much about the team and this investment is not a huge investment, it's an early stage investment and -

Howie: Just get your foot in the door and -

Al: Yeah. And like it's - this team just felt right in a lot of ways and the position that they're in. So a lot of that stuff got me really fired up about what they're doing, so.

Jillian: I love a good fanatical market. Years ago there was a book, it was knitting with dog hair.

Beck: What? What?

Jillian: This is an important story.

Al: It's a thing?

Jillian: And it was. And they came and they pitched this to me and I thought, this is the most ridiculous thing I ever heard. But they showed me the numbers on dog owners, and they showed me the numbers on knitters, and then they said, this is combined, every one wants to have a little piece of Fifi that they can wear. It was crazy.

Al: No. Really.

Jillian: Well, I passed. Okay. This has taken off. And it just showed me that if you have a fanatical market, you can sell them anything.

Howie: It's like Twitch - Twitch is a great example of that too.

Beck: Yeah, that's true.

Howie: When people - if someone pitched me on a voyeur platform for people watching other people play video games, it would be like - what?

Beck: No. No.

Howie: That's the stupidest thing I ever heard. 

Josh: So what do you think you'll get the terms at?

Jillian: Six.

Josh: You think you'll get it down to six?

Jillian: I'm not gonna do it if it's not six. 

Howie: Their margins are great; their growth is not. 

Jillian: Yeah

Howie: So like six, between six and seven sounds - 

Josh: I think what's unique about this is it really is horse-led growth, which I think is the way -

Beck: Horse-led growth.

Howie: Wow.

Al: Tackle this market -

Howie: You went there. That's a lot of - you're talking a lot of horse sense. I like that they're combined intellectual horse power too.

Beck: Oh god. All right we're done.

Jillian: You know what -

Beck: We're done.

Jillian: God, you know what, I love that so much. 

Al: I feel like this conversation's a little bit of horse shit.

Jillian: We're wrapping. oy

Beck: Okay break time.

Kinsey and Jessa trotted out of the studio with $100,000 in commitments from Al and Jillian, who were ready to take this Mustang for a ride.

But there’s a loose end left untied. The founders think their company is worth $10M. The investors think it’s worth 6.

That’s a bit of a gap. When we come back, Kinsey & Jessa will try to close it. But terms end up being the least of their problems.

—

Welcome back. A week after their pitch, Kinsey and Jessa got on their first due diligence call with Jillian and Al. Please fasten your saddle, keep your arms and legs inside the horse at all times. No seriously, buckle up, this is a bumpy, tense series of phone calls.

Jillian: First of all, you have a lot of competition. There's one from the International Equestrian, it's called Horse Riding Lesson App. There's another really big one called Rider Guider. Why are you going to win?

Jessa: There's only one other company that is truly doing listen while you ride audio lessons by top coaches. And they took that page right out of the Ride IQ book because they've seen the hype around Ride IQ, which is great. Like it's a good sign to us. The company is called Noelle Floyd. 

 Jillian: I saw that 

Jessa: They launched audio lessons between 10 and 14 days ago. So this is fresh, but it's very much been on our radar. We've had coaches call us and talk to us about the fact that they were approached by Noelle Floyd. But there's not a concern there from our standpoint, they have said that they'll release new lessons each month. We're releasing new lessons every week. And I just can't imagine people really doing what we're doing better, given the network we have and the commitment that we have to this. So they are our biggest competitor. Is it a concern to us? Honestly, truly no. 

Al: I - I think it's good to see that this other company, this Noelle Floyd, is copying what you guys are doing and reaching out to your trainers But, I also think it is something that you should be very, very worried about. and not, as flippant about it because, uh, it's just an example of, Oh, somebody who's in the space is able to flip this and turn it around and release and test it. So I think it's important for you to recognize that you do have some people nipping at your heels. You may have had a head start, but you got to stay in front. 

Kinsey: One thing I would like to add is just Our goal has been to create a product that expands beyond like the possibilities of the equestrian space and our real mission and the vision of the company is to give everyone access to world class coaching. And I think that that's really different from what these other companies are doing. it's a much smaller scale than what rideIQ is trying to accomplish. 

Jillian: Okay, and you're raising, remind me. 

Kinsey: We're raising a million and a half. 

Jillian: and what is the valuation? 

Kinsey: We're, we're targeting a 10 million post. 

Jillian: I don't think anyone at this point in time would come in with anything higher than six. 

Al: uh, there's, look, I, it's super rare and, and. Not really typical for a founder to come to the table with, hey, these are our terms. When you have had no validation from investors that this is actually what the market will bear. It just feels off and not quite right for, for where you guys, where you guys are. 

Jillian: I need to do more work on this. I need to understand. A little bit more about the competitive landscape. Uh, so I'm not gonna invest right now. I, I feel there's a lack of defensibility here, and I'm not quite sure how you're going to win. 

Kinsey: thank you Jillian. 

Al: Um, I'm not out yet. Um, I think the valuation is the biggest gap we've got to work towards, uh, to make sure that, that we figure that part out. Um I don’t know if the 6 million, makes sense for you guys, or if that’s a no altogether. Um but would definitely like to have that conversation because I think that’s where we’d like to be as well.

And just like that, Jillian was off the horse. Of course. But Al was still in. A week later, they got on another call, but they were still stuck on terms.

Kinsey: where is your appetite? Like, what is the valuation that gets you really excited about being involved in Ride iq because … 

Al: So for me, I kind of look at it as that 6 million number is good because that's like still a 15 X your revenue, which is still a pretty sizable markup. So that's where I'd like to see things. 

Kinsey: Totally hear you on the 6 million. My inclination is to try and push for 7 or 7 and a half? I don’t know what your thought is there, and I know we’re just like splitting hairs at this point, which I also don’t want to do, because it’s not a good use to anyone’s time. But I don’t want to walk away and be like, man, I wish I had just like, asked, and find out what he thinks. So that’s kind of how I’m feeling about it right now.

Al: Yeah no that’s reasonable and, you know, I would say 7 is worth having a conversation about. We do, what I walked about on the show was kind of a 50k allocation out of our fund, right, but we also have the opportunity to invest out of our syndicate as well and I can tell you that that the 6 million number is definitely going to attract far more attention. We’ve seen it over and over again. 7’s not bad, it’s something we should, we can certainly discuss. assuming you get traction at that amount. 

Kinsey: yeah… 

Josh: If the terms were at the, at a six mil cap on the safe, would you be willing to write the check more quickly, as opposed to waiting to see how the round is going?

Al: Uh yeah 100% and I’d probably spin up a syndicate almost immediately too. If it's the right stage and the right valuation and things like that we have the ability to do around 150 K out of the fund. If we're at seven, then I'm, I'm definitely in for the 50, assuming you get your traction. 

Kinsey: That definitely helps, like the faster we can execute this fundraising round, the sooner we can get back to operating the business. So we're I mean, that is huge for us and great to understand. I don't know if you know right now or if you need to think on it, but would the number you're investing change at six as well?

Al: If we're at six, then yes, I would potentially be more interested in going higher. Closer to that 150 number out of the fund itself. And like I said, I could start spinning up a syndicate pretty quickly if that's where we're at. when we get things dialed in where we want them, then we, tend to go in a little deeper.

Kinsey: Yeah. I mean, if it's, if it's the difference between like getting a safe written next week and waiting until we're, like have full commitments on our round, I think it definitely changes our stance on the valuation. So, um, just let us discuss it and we'll come back to you. 

Al: Awesome. I'm, I'm ready to go with you guys. I like what you're doing. I think you guys are amazing and I'm excited to take that next step with you guys. 

So with the $150,000 carrot in place, Jessa and Kinsey had a decision to make. But first, they did their own due-diligence… on Al. They spoke to a few founders in Al’s portfolio, and he passed the test!

Just under a month later, they all got together to finalize the deal.

Kinsey: where we left it off on our last conversation was 150k out of the fund plus a potential for a syndicate investment at 6. And if everyone is in agreement on those terms, that's something that we would be really excited to move forward with with you guys. 

Al: Awesome. we're excited as well. How's, uh, how's the fundraise been going so far? how many. Angels or, funds or whatever have you had conversations with? 

Kinsey: Yeah there’s, there's two angels that we're in conversation with and then two other funds that we're like actively conversing with. And then, I mean, always taking additional introductions. There was another introduction made, made for us on Monday of this week. So, we're still kind of growing that list. 

Al: does that mean that since we've met you've had conversations with those two? Angels and those two funds?

Kinsey: Correct, yeah.

Al: Okay, um, so, I'm gonna, I'm gonna share some thoughts here. Um, that's not anywhere near enough. And I say this with love, you should be having four conversations every couple of days, if not every day. That's not what I expected to hear. I was hoping to hear that. Oh, we've got half a million committed we've got these investors who are good with this ballpark set of terms and it feels like it feels like you guys haven't really pressed on the fundraise that much and so fill me in on like, is that what's happening? Am I wrong in my assumption there? 

Kinsey: The outcome of these conversations with you guys are really going to kind of help define how the rest of the round looks. so we wanted to really see this through and make sure that we gave this, uh, our, our full, kind of the full focus that it required. And then, really push on other funds with, once we have these, these commitments, finalized and use that as like our leverage to make them move faster. 

Al: okay

Josh: So where are we at, Al? Are you, like, having second thoughts on your investment? or is there still a path forward here?

Al: Um, that's a good question. I, I, I do have hesitation. I think what I would like to do is say, okay, from the fund, we'll commit 100k at these terms But I do want to be able to see that... You guys can commit to the fundraise and that you can keep your investors updated and you can run a process, right? And so I would like to see you be able to get additional commitments. And if you get to a certain point and it's looking good and you're getting these commitments and you've got great momentum and you need a little bit to finish it out then maybe that's something that we can look at doing as well.

Clearly Al had colt feet.

But I knew this deal was in deep horsesh*t when a month later, I got a text from Al, that said he hadn’t heard from the RideIQ founders since that call.

And then a month after that, another text from Al. He still hadn’t heard from them.

Josh: Hello, Kinsey, Jessa. It's been two months since we last spoke. What happened with Al?

Kinsey: Yeah, it has been two months and it's flown by. Um, first meeting with Al, he had talked about doing 150k at 6 million and he was like, I'll do that now, or if you guys insist upon doing it at 7 million, we'll talk about 50k and it'll be contingent upon a larger raise. And so it might have, like, who knows, maybe it was a miscommunication, but we took that to mean he was kind of ready to be our first check. When that was not what he came back with, we were kind of just like, this is probably just not going to work, which is disappointing, but it's okay. 

Josh: In your minds. He was flipping to say like, I'm not going to lead this round anymore, but I'll be the last check in.

Kinsey: Yeah.

Jessa: Moments after we got off that call, it certainly was us talking about whether Interlock was the right partner and vice versa, I’m sure they were having that same conversation too. He was critical of us for not having spent the past period of time since we spoke to him, all systems go on fundraising, but under the agreement of him being the first check in the door. You know, he was, he was being critical based on expectations that he did not ever explicitly share with us. 

Josh: right

Jessa: You know, the conversation was based on them being first. 

Josh: So you'll reach back out once you have some momentum in the fundraise to say, Hey, do you still want to be a part of this? Or have you just kind of written this one off with Al 

Kinsey: I would say the latter, Jessa, would you agree? 

Jessa: Yeah, I think so. Given those conversations and the change in the agreement, it was just like, this probably isn't a fit, which. Of course, it's a bummer. The momentum would have been great and those follow-on deals would have been great, but it's not worth a check to get someone in the door who's going to be a source of stress.

Josh: Do you think you dropped the ball with Al or Al dropped the ball with you?

Jessa: I, I think we certainly could have fostered that relationship better. To be completely honest, we got off the second call and I was ready to move on and build our business and I just moved on with it. in hindsight, this was a learning. You have these weird moments with people and then you have the opportunity to like be human and share what you're going through and share what you're feeling. And there's a positive trajectory that you can go on from there. And we didn't take that opportunity with Al. 

Josh: Yeah I was going to ask if you're getting a case of investor whiplash, but it sounds like for the most part, you guys are just building your business. 

Jessa: It's interesting that you should say that though, because a lot of this brings me back to TechStars, part of tech stars as mentor madness, where we meet with 60 investors in one week, which actually isn't - 

Josh: Yeah, can I just say, that’s crazy. That sounds like hell

Jessa: It is hell. there have been times that I look back and I'm like, they should not do that. That's, you know, like emotionally distressing and of course, getting contradictory advice that whole time. But as I get distance from it, and as we go through more and more experiences, including like with investors It is so much easier for us to check in with our intuition and trust ourselves I mean, venture capitalists they're brilliant and they've seen so many things, but trusting ourselves in terms of like taking that information in but not treating it as gospel is a very important skill for moving forward in the direction you intend to.

Josh: Yeah. I absolutely agree with that. Thank you both for going on this rollercoaster with us despite the investors on our show, not working out.

Jessa: Actually on that note, you guys wouldn't believe it. I don't believe it, but we've already had two calls with people who are just interested in RideIQ based on the trailer that you put out And we're like, how did you even know it was us? I could not believe it So it's a real treat to be part of it. 

Josh: That's awesome. I can't believe they found you just from the Peloton for horses line. 

Jessa: Unbelievable

Kinsey: Yeah, wild. 

There are 2 ways of hearing what just happened. Some of you will hear that the investor moved the goalposts, that Al was maybe a little condescending to the founders. I think that's a fair critique.

Some of you will hear that the founders - they weren’t communicating well enough. And will say, hey if I was in Al’s shoes, I wouldn't have invested either. 

Either way, I think you’re right. All of those things happened. It sucks, but this kind of thing happens all the time in venture. 

In the end, Al and the founders, were like ships passing in the night. Or horses. Passing on the trail. 

Next week on The Pitch… have we finally found the killer use case for VR?

Andrew: Have you used a Meta Quest before?

Elizabeth: No, I haven't. 

Andrew: So you should just be able to put it on, And if you look to your left, you should see my son's first ultrasound.

Mark: Wow. 

We’ll see you next week in the pitch room.

Applications are open for next season of the Pitch! We’re gonna be in Miami in January. 18 startups will pitch the investors on our show. So if you or someone you know is raising pre-seed or seed, go apply at pitch.show/apply. Even if you’ve applied before, apply again. See you in Miami in January.

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This episode was made by me, Josh Muccio, Lisa Muccio, Kerrianne Thomas, Anna Ladd, and Enoch Kim with casting help from Peter Liu

Music in today’s show is from JT Ruff, Onders, Chocolate Milk Boys, The Giddy Uppers, Our Many Stars, Joya, Breakmaster Cylinder, and The Muse Maker. 

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The Pitch, Inc. and their respective employees and affiliates do not provide investment advice or make investment recommendations. The information provided on this show should not be used as the basis for making investment decisions. Listeners should conduct their own research and consult with their own investment advisors before making any investment decisions.