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Medley's Jordan Taylor on launching a successful platform rooted in community & professional growth

Joining me on the show today is Jordan Taylor, Co-Founder of a platform called Medley.

Medley is a membership platform redefining personal and professional growth, on a mission to make high-quality experiences accessible to broader audiences. Members are algorithmically matched into small, diverse groups that meet monthly in sessions led by certified coaches.


Medley members benefit not only from these curated sessions, but also a community built on diverse perspectives – leading to positive, enriching, and engaging interactions.


In this episode we’re covering Jordan’s experiences that lead to her launching this business in partnership with her mum, Edith Cooper, the importance of testing your idea and speaking to your customer before building a product, and her experience on fundraising including lessons learned and tips.

Please note, this transcript has been copy pasted without the lovely touch of a human editor. Please expect some typos!

00:03:24 So my name's Jordan Taylor. I grew up in the new york area in the suburbs of new york city and I'm the Co founder and CEO of Medley, which is a platform that is designed to enable our community to grow professionally and personally, Membership includes access to a group that meets every month under the guidance of an expert leadership coach as well as really high quality and engaging programming members of our community, our lifelong learners. So people who are really excited about learning perspective of others, we are arranged, people range in age from twenties to sixties and we have men and women and people are really excited about the prospect of having dedicated group experience where they can learn from perspectives outside their their narrow lanes that they're in at this point sounds so interesting and something that I haven't heard of before. So I'm really excited to learn all about it before we kick things off about the how and the why and the marketing and all that kind of thing. Can we go back to life before you started the business and what was kind of happening at that time that lead you onto this entrepreneurial path and deciding to launch a business.

00:04:30 Certainly so medleys really founded from uh my own personal experience of someone in their early mid twenties living in a big city and trying to figure out what I wanted, what I wanted at work what I wanted uh in my personal life, how I wanted to show up every day for myself and how I needed to take care of myself. I sort of found myself in the middle of this, this big transition point and didn't have a place to really understand how everything integrated together and at the same time I'm someone who also really loves communities and team environment, so I grew up playing a lot of sports, a lot of activities, I was fortunate enough to be able to, you know, do art classes and ice hockey and soccer or football as you say, and in university I was also an athlete, I was on the crew team and so it was this confluence of both, really meeting a dedicated space to figure stuff out as well as really creating the dedicated type of community that you get in a school environment and and in sports environment as well, that stuck with me, that that pain point really stuck with me, that experience is really difficult.

00:05:39 Um it really affected my mental health. Um I became have been navigating depression and anxiety really since, but it sort of started in that transition point and I worked in consulting for two years after after college, and then I worked at a startup media company called Mike and the team grew incredibly quickly and it was a really exciting time and then I went to business school because I knew that I wanted to have, you know, I mentioned, I really love communities, I knew I wanted to, you know, hopefully try and create something or explore something in terms of a business idea and I was excited about the prospect of having a little bit more structure and people around me who are, who are excited about pursuing a similar path and so when I was there began testing and researching and I think that's the first step in any idea and from other friends of mine who are entrepreneurs, they say that to its understanding your customer, it's understanding what other solutions are out there. So I really don't write in after I graduated, I was fortunate enough to join with my mother actually, her name is Edith Cooper in building the business.

00:06:47 Um, she realized that there was such a big opportunity in her background, you know, she was a leading finance and HR executive, she was running HR at Goldman Sachs for 10 years and then ran a lot of businesses there. It was this sort of perfect combination of both of our lived experiences and so about two years ago we were off to the races and yeah, I'm happy to dig in on more of the tactical day once if that's helpful, but it's certainly been inventor ever since. Gosh, it sounds like it and it also just sounds so special to be working alongside your mom and learning from her as you go before we just jump into the, how, what are the kinds of things that she's taught you since launching the business together. Oh, and it is very special and I do feel very lucky to get to work with her. Um some of the things that she's taught me trusting your intuition is a really huge one. I'm really someone who loves to have all the data and you know, as much as I can about a given topic, but when you're running a company and starting something, you don't have a lot of data, so that that approach actually doesn't really work, you need to be able to, you know, read what you're seeing, but you also get, need to have the confidence to really trust your own instincts.

00:08:01 And she has just helped me become more confident in my own instinct and I've also just seen her time and time again um really be clear about, no, I think we should do X, y Z. I think we should hire this person. Uh and that's really helps me as well. I think the other thing that I've realized is it's just an important life skill that I've learned a lot from her um is her ability to connect with people and to listen to them and to help them feel heard and seen um as themselves and that shows up in a lot of different forums. Um you know, whether it's she and I approaching working with a partner, um you know working with a freelance designer or working with um you know, another potential company as a partnership, she can go into meetings and get people on the same team in a way that is truly her unique special skill in the world. And so I've also learned a lot about how to connect with people and motivate people and from that point of view, it's really just like listening to them and coming in with an open mind, Gosh, that just sounds so amazing, I love that.

00:09:15 Okay, so you have the idea, how do you then go about actually bringing this to life? What are the steps that you used to launch this business? Get it off the ground, get it funded potentially, you know, that kind of thing? Yes. So first thing we wanted to do was to both really understand the problem that our customers experiencing as well as start to test out initial versions of the solution. So we really dove deep into the problem first because we just felt like we weren't going to be able to make decisions on the product side without having that deep, deep expertise. And so what that meant for us. We did interviews, we did interviews both with people who we knew as well as people who we didn't know. Um and what was fun about the interviews that we were doing for medley and and something that I think honestly is because so many products and services can impact Mosul parts of people's lives. That experience is actually really fun because I got to even just get to know my friends who I was asking uh in in a very clear way. So step one was really writing down okay, here are the questions that I want to ask, making sure that they were open ended enough and not leading and you know, gay people space to share really what their experience was like making a list.

00:10:30 Okay, these are the types of people I want to interview, setting those up, taking copious notes, going through it again, talking about that with them with Edith, we did focus groups, we did surveys uh and we really spend 3 to 4 months just understanding, okay, how are people going about finding community and growth in their lives now and what does that look like? You know, people are setting goals for themselves, people, some people I spoke to have their own systems where they were setting goals every year and they did like little annual reviews for themselves. I love that. Yeah, I also did um a lot of competitive research, so I went and looked at existing programs out there courses, you know, there's everything from self help books to life coaching programs to individual one on one coaching and that was also really helpful to understand, okay, here's what's working in the existing solution set and here where we see the opportunities are so that was probably the first 4 to 6 months of medley. And then from there we started prototyping the group experience. Uh so we held free group sessions for us to work out the content, the coaches, the group composition, those types of things, but I think that that framework of really okay understanding the problem understanding solution than starting to test on the solution ist and as possible is pretty applicable to any type of business.

00:11:49 And looking back, I think the only thing, the thing that I would really wish that I did sooner was to push to test even faster than we did before and I think that's something we're working on now is just continuing to iterate, got it. I have a few questions on different points that you mentioned going back to the interview process. How many kind of people did you interview? Probably 20-25 in that very first batch. But we've done different Sort of sprints of interviews since then. So overall we've spoken to a couple 100 people, a lot of people over the past two years, but you know what we found was after 10-15 interviews you become able to anticipate what the person is going to say. Uh interestingly, you know, there is certainly a wide variance in people's experiences but there's certainly a path to identifying different customer personas and you know, there are diminishing returns after doing more than 15 I think got it and when you were asking those questions, what were the clear problems that we're coming out of that and was anything unexpected?

00:13:04 Yeah, so I think what are the clear problems? I mean, one was that there were a lot of communities out there and people will say, oh there's a lot of, you know, there's membership club type things where you go to a place, there's social media, where that's definitely a community where I show up with people, there's free panels and events and speaker series that you can go to. But the consistent pain point on the community piece was just that there's a lot of low engagement and sort of lower commitment type experiences and what we heard from people was that they really liked, that they liked being able to just drop into a speaker event or something, they find an event, right? But they weren't really necessarily meeting people or forming new relationships in a way that they were hoping for. So, you know, that we just saw was a really big learning from the community standpoint and even just talking to people who belong to various membership type clubs, because originally medley was going to be an in person experience. We just heard a lot of really consistent feedback that yes, you know, I I feel connected to others in the sense that there's people around me, but I'm not meeting these people, I'm not forming new relationships and that's where our big insight was like, you know what, there's a lot of lower commitment type experiences out there, but the best benefits often come from really being engaged and from really being committed to other people and yet those like high commitment experiences are really hard to access.

00:14:33 You know, I had a really incredible experience when I was at business school where I took a leadership course and I had a learning group of six and we spent two hours together every single week, nobody missed a session. It was utmost confidentiality and that just jumped out at me as wait a second. Like why is there so why is it so difficult to ask this experience like this if you're just sort of a broader consumer? So I think that was the biggest thing in the community front and then on the growth front, people were just saying that they felt like there were a lot of individual practitioners out there and a lot of content, very targeted things. But it was the integration that they found challenging, where it's like, yeah, I can think about how to grow my career, but what does that mean for the rest of my life or how much I think about fulfillment outside of work and my relationships and what does that mean? And so it was that integration that sort of messier space where you know, you're everyone's exploring and trying to figure out how it all comes together is something that people also found difficult totally.

00:15:34 That all resonates with me when you're saying those those problems and what people were saying when you moved on to building the product out and deciding what these group sessions were going to be like, what that structure looks like over two months, three months, six months. What is, what is it like? What happens when someone gets into a typical like monthly? I think I read that it's 90 minute catch ups. Um, Yep. And what's the format, what does it look like? Yeah, So um, the way it works is the group meets every month and it's a year long commitment, but in the first month there is an extra meeting and that's because we found that we need an extra session for the group to really gel and get to know one another and sort of set their ambitions over the course of the year. So even backing up before the group experience, people fill out a pretty detailed application which we use to match the groups of people together and it's in the matching actually, that really creates a big piece of the medley group experience is something that we view as our competitive differentiator compared to other types of businesses.

00:16:37 And so what we've been able to do is we've been able to match people together that have a similarity in terms of what they're trying to get out of the medley experience and they're sort of broader priorities, but we also really push for diversity of experiences and diversity of perspectives and so throughout the year they go through a journey that um is charted for them at the start with their coach, so the coaches in every single session and is leading that for them, and it's a series of exercises reflecting on topics like leadership values, um your relationships, self awareness and a huge piece of the benefit is not only in the content but also in the live coaching that the coach is able to provide. So right now the sessions take place via zoom, but we have people in the community from all over the world, so I think it's 11 countries and 20 states in the U. S. And then the group is also sort of engaging with one another and checking in in between the sessions. Um We also have developed and really invested in our programming outside of the group and everything for us is like how can we make this as engaging and as interactive as possible.

00:17:45 So everything is pretty small format. Um We do workshops and we do conversations and we are really collaborative with their community in creating experiences that people are asking for and that they want. So we got a question like we'd love to have a session on entrepreneurship and we were able to make that happen. So yeah that's kind of how the experience is now, and we have a big vision for what we want this to be in the future. Um you know, creating a digital product to augment the group experience in the membership, Really thinking about how people can understand their own growth over time and how technology can enable them to do that, but we're certainly trying to really just now, let's focus on our first our first customers. Yeah. Gosh, that sounds so fascinating and so needed because when do you have those kinds of conversations and you know, for the, for the average person, you know, getting a coach can be very expensive, It can be, you know, you've really got to rely on a good recommendation or know someone. Um So yeah, that's, it's such an interesting problem that you're solving and I really do see the benefit.

00:18:47 I want to go back to that early um you know, once you're ready to launch and once you're ready to bring on your first batch of customers and the first batch of people who are going through the program, I did read that you launched with a pilot program, is that correct? Um For the beginning, yeah, yeah. So we um we did a pilot last year actually, so we had a a shorter term, it was just two months, it was free to participate and we had five groups really for us to validate Validate mentally a little bit further, but also to test out the matching as well as the coaches and this past summer we launched in July 2020, so just a few months ago we launched with discounted pricing. So founding membership and I would say the biggest thing about pre launch and sort of launch is uh, we definitely didn't feel ready, but I don't think any founder, I've spoken to really feel like fully ready for women for the day that you sort of press go.

00:19:50 Um, and so what we've really tried to do is frame it as, you know, we're continuing to learn and we will be continuing to learn even as the business grows from where it is now to hopefully, you know, reaching thousands, if not millions of people one day. So, um, you know, that's, we really try to, its use learning into every aspect of what we're doing, but we were really happy with how the launch went this summer. And how did you launch, what were the kinds of things you were doing in marketing to attract people to sign up and reach new audiences? Yeah, so for us, um, we're really lucky in that the press was really excited about our story and what we were bringing to the table, I think, uh, you know, to black women founders is pretty rare as well as mother daughter team is also pretty rare as well as the fact that we're doing something that is certainly different from a lot of things that are out there. So we were fortunate enough to be featured in several different publications were informed fast Company Techcrunch and the thing about prices, you don't really know, like we did some interviews, we weren't really sure what was gonna come out of course, um from those interviews and we were sort of hopeful, we told them, okay, this is the day that we're watching, you know, you can't publish anything until then.

00:21:01 And so on the day itself, we did everything from sending an email to our existing email list of people who had, you know, attended a free session or, you know, something like that as well as our immediate networks and the network on our team. And so we probably emailed personally, maybe a couple of 1000 people, um as well as posted on social media and asked people directly who we knew who had bigger followers. Hey, like would be incredible if you can support our lodge by re sharing this, like really, really appreciate it. And I think that's something that I would encourage anyone to do. Uh it's a pretty easy ask uh and people love to be supportive if they know you. And so I think that's something that I wish that we'd actually even been more organized around. It's just really tapping our networks and and friends of friends and things like that um, to ask for sort of that organic boost. But yeah, our launch was a combination of press email and starting to post on social media.

00:22:02 Is it also part of your strategy to actually kind of connect with bigger companies and get like a whole company on board. I'm aware that like, they wouldn't have them together but like bringing in, you know the company aspect versus like the individual. Yeah, so we're currently exploring that still and we already have a few b two B business business clients actually who are paying for medley membership for a few of their employees. And we definitely view that as a core part of our strategy and the opportunity that we see going forward and especially with Edith background, you know, she knows a lot, she knows a lot of ceos, she knows a lot of C. H. R. O. S. The chief HR officers around the country. Um and you know she's on the board of three public companies and so we view that as another area that we that we really want to lean in moron and at this point you know we're talking to a couple more business to business partners but really flushing out like if anything how we would change and adapt the medley experience or deliver even more value to companies.

00:23:05 But you know we're really we really are doing that because of a reaction to what happened this summer where we got so much inbound interest. We've got so much um invent interest from people who wanted to get their companies to pay for their medley membership from people who worked at companies that were interested in providing it and so um we sort of had to adapt and try to seize that opportunity for sure totally sounds amazing for companies official. I always love to ask about the money side of things, how you were funding it in the beginning. I know you've done a fundraiser now as well, um, and how that kind of evolved, and then when you're talking about the fundraise, you know, how that experience was and what was it that you learned during that process? Yeah, so we closed around a little over $1 million January and it was primarily from, you know, a couple of angel investors who were also entrepreneurs, um, you know, one VC fund put in a small check for them and, and yeah, it was mostly, it was mostly entrepreneurs actually.

00:24:08 And we set out to raise in Q four of 20 of last year, Thinking that we could raise, you know, 2-3 million. We've done a pilot, uh, we had really good traction and data from that and it was a really difficult experience. It was really hard, harder than we thought it was going to be. And so, you know, there's some tactical learnings I have from the process, you know, everyone says, and make sure that you're, you're careful about when you have meetings and you're not raising until you get your first check in and there's sort of this whole, uh, sort of mumbo jumbo and, and unspoken language that happens in the fundraising process. So basic things, you know, making sure you have a very clear target spreadsheet of who you want to talk to, you track all of your calls, all of your, all of your notes, every question that you asked, you should be writing it down because you're going to get that question again. That's a very simple tactical thing, recognize that it's a numbers game and that we probably did 60, 70 meetings, uh, and got four or five yeses, but I have friends who took, you know, 100 plus meetings and ended up with, you know, seven or eight guesses.

00:25:22 And I didn't fully recognize that beforehand. And I think if I had, I would have just been a lot more aggressive about saying, okay, I'm going to do all my first meetings within these two weeks. Uh, and then hopefully see what happens next. Um, but the more you can sort of stack those conversations, the more you can get momentum in the process and that's what it's really all about at this early stage. Yeah. Gosh, it's so, it's so many meetings and I've spoken to women who have been like, you know, it took me 200 or 300 meetings to get my first yes, kind of thing. Like really that grind of back to back to back, like some someone I spoke to was like, we did like six meetings a day, like, you know, something crazy or six calls or whatever it was. Um, and you really have to get comfortable with rejection and, and people being like, no, sorry, not interested, I don't get it or whatever, which is, it's a tough learning curve. I think it's really hard. It's a good life experience though, because, you know, up until this point, you know, I've been super lucky to be able to go to incredible educational institutions.

00:26:27 I really love school and you know, enjoyed that experience. I hadn't had a lot of nose like this before, before we started fundraising. And I think ultimately it's, it's really increased my resilience and as well as my broke down my confidence a little bit, but now I'm sort of building it back up again and building that muscle of, okay, just because someone says no to you, it doesn't reflect on you, it most likely has a lot to do with whatever they're dealing with. Uh, and the practice of just being able to respond with, you know, confidence and self assuredness is a pretty valuable life life practice for sure. 100%. Mm what are the kinds of challenges that you face in building the business today? And what's happening kind of now for, for building the business? You know, I think, um, one of our biggest challenge is, is that, uh, sort of this broader opportunity of intentional community as well as like growth experiences is certainly becoming more crowded. So there's a lot of, you know, group programs, there's a lot of online memberships with content.

00:27:35 Uh, and the space is certainly becoming more competitive and so I think I view that actually is a challenge and an opportunity because I think it will force us to really crystallize and, and uh emphasize are differentiators, our value proposition ahead of uh not ahead of, but in the face of other businesses and so you know right now we're doing a lot of testing on the go to market front, really trying to build out and think through how we're going to reach new audiences um, and sharing the medley story. Uh you know, we're going to test different types of content. Uh of course social as well as, you know, as part of social, exploring linkedin even further. I think there's a big opportunity on linkedin as a platform actually. So yeah, I think that's really the biggest thing for us is how we can reach, reach the right people totally. Absolutely. I guess that's a big challenge that any business has to face and figuring out where their people actually are hanging out, you know online in real life, all that kind of thing and finding ways to get in front of them and spread that message.

00:28:40 What advice do you have for women who have a big idea and want to launch their own business, I would say two things. Um which one which I mentioned earlier is really just test test test and do it before you feel like you're ready. Put up a landing page, you can spend $50 on Facebook or Instagram ads and you can learn something from just $50 and talk to as many people as you can and don't be so precious with the idea itself because so much is in the execution, I would say the other thing is to ask for help much more than you want to instinctively. Um I've been amazed at how willing people are to share their knowledge, share their expertise, make an introduction, give me feedback on something, but you definitely have to ask for it and that's something that um I certainly have learned over time and wish I had taken to heart much sooner. Yeah, I've heard that one as well from other women on the show and it's something that sometimes it doesn't feel easy to ask and you're like afraid to take that to take that step.

00:29:45 But then you're, it's often the case that your met with such a beautiful response of people going above and beyond and really wanting to help and you're like, wow, there is so much support out there, but you have to take that leap forward and and you know possibly also face not hearing back from someone or whatever it is. Um yeah, I totally understand that we are up to the six quick questions part of the episode question number one is what's your why two create experiences and help people be their best. I, I personally, I love being on a team and in a group experience where people are just growing in the same direction and are supporting one another and I want to make those types of experiences available to anyone who wants one and I try to do that even just in my personal life and how I show up in the world. Um the other one, the other big y for me is is there's so few examples of black women entrepreneurs and success stories and I really believe that Edith and I have a responsibility to try to make medley as great as it can be because we more examples of black women's success, especially in entrepreneurship and um I just feel like with with so much privilege that I have at this point to be able to start a company um I can't let that go to waste.

00:31:10 100% so true. Absolutes. Question number two is what's been the number one marketing moment that's made your business pop for us. It was definitely launched. Um it was, it was and it was the press around launch for sure. Um it really told our story from different facets and in different directions um from day one and I think it just it just helped us establish a level of credibility that that would've been challenging. Yeah, totally, you got some really amazing press and it's just so cool to have companies like fast company or fortune or you know, those really huge hitting media brands coming out and supporting you and and giving that credibility from day one so called Question # three is where do you hang out to get smarter? What are you reading? What are you listening to, what other corners of the Internet are you on? Yes. Um to get smarter, I'm really into listening to memoirs um and so I'll listen to audiobooks and I'll listen to memoirs.

00:32:14 But to be honest for me the biggest the biggest things that I find will spark inspiration is like reading different fiction books uh and thinking about different parts of the world and different people's life experiences I think for the business that um Edith and I are building we really need to be able to like connect to humanity and so of course I spend time on twitter and I follow a ton of really smart and savvy sort of business type people and then very exposed and plugged into like start a business culture. But yeah for me fiction really helps me expand my mind and feel sort of more connected to the human experience. Do you have any recommendations of your favorites? Yeah I read a great book recently called anxious people that was written by a Swedish author um and I really enjoyed reading it. Um The other book that I I really love lately is the three body Problem um it's a sci fi book that is written from a chinese perspective and so much of the, the literature that I usually read is written by very western or american or british point of view and just hearing um and reading this, this exploration of what the world could be like in the future from a very different perspective, was really powerful.

00:33:32 Yeah, that sounds really cool. I'm going to link them in the show not