First Time Founders with Ed Elson – This Mother-Daughter Duo Started a Leadership Coaching Platform

Ed speaks with Jordan Taylor and Edith Cooper from Medley, an online platform for group-based leadership development and coaching. They discuss how they dealt with funding challenges and pivoted their business, the importance of mastering “soft skills”, and the struggles and joys of being a mother-daughter team. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

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• 0:31Speaker 01

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• 0:59Ed Elson?

  Scott, what would be your advice to someone who wanted to start a company with a family member?

• 1:04Scott Galloway?

  First word that came into my mind was "don't."

• 1:09Scott Galloway?

  Look, I just think it's situational. It's so much of resting on the family dynamic. I mean, I always thought I would never want to leave my kids a lot of money, and I wouldn't want to work with my kids because I enjoy my relationship so much with them that I'd hate if we didn't get along professionally, that it could put strain on the relationship itself. But at the same time, I also love the idea of building something that I could give to my kids, that they could enjoy and build. And family businesses, a lot of people, you know, there's a lot of family businesses, and for a lot of people, I think they're very rewarding. I just think it's situational.

• 1:51Scott Galloway?

  If two brothers get together and they have an idea for something, I get it. I would think, and maybe this is because I'm not very close with my family, I was close with my mother, but I hate having that many eggs in one basket. It's just the idea of adding another potential point of dysfunction, where you start a business together and it doesn't work. I just think it'd be devastating. Like, if I started a business with my son... And it didn't work, right? And it put tension on the relationship. I would just, that would be heartbreaking for me. So what I would suggest is that if you are thinking about a business with a family member, that you immediately have an informal board of directors.

• 2:32Scott Galloway?

  And that is someone outside of the family that you both trust that can serve as a fiduciary for kind of coaching you around issues. Because it's one thing if your business goes bad, but to strain a relationship in a family, I think would be devastating. I knew one of the nephews and nieces, one of the privileged jerks of the Bronfman family. And I remember I had a share with them in the Hamptons. And this person was shitposting Edgar because he'd lost so much money.

• 3:01Ed Elson?

  I'm confused why a Bronfman was in a share house.

• 3:03Scott Galloway?

  Yeah. I was in a share house. Yeah, I did it because she had hot friends. Anyways.

• 3:10Scott Galloway?

  But I remember her just talking so much shit about Edgar because he bought some company and turned eight billion of their fortune into a billion. I don't know, it just feels, and then, you know, my entire insight into a family business is succession and they all look fucked up and like they hate each other. So my general, my general instinct is I don't want to say never, but I think you're better off doing it with friends because I'm still, I'm still close with my initial business partner. No, that's not true. We're still friends, but we're not close. We just had a different approach to business over time. And while we're still friends, I invest in his companies. I, he could, I know I could count on him for anything and he knows he could count on me. But if we were like brothers and there was sort of that, what I'll call easing back

• 3:54Scott Galloway?

  from the relationship, I think it would put a strain on our brotherhood. And I just, I think family is so precious. My initial inclination is tread carefully around that.

• 4:10Ed Elson?

  Welcome to First Time Founders. Since COVID-19, the dynamics of the workplace have significantly shifted. Nearly half of Americans today feel unsatisfied with their jobs and more than half feel they are lacking in professional growth. Companies meanwhile have done little to address this. Eighty-three percent of companies say developing leaders is important, but only 5% have actually developed leadership programs. My next guest, while at business school, came up with an idea to address the problem: an online platform for group-based leadership development and coaching. And to get this idea off the ground, she tapped a veteran. Her co-founder is a former partner at Goldman Sachs, a current board member of Amazon and PepsiCo, and also happens to be her mother.

• 4:54Ed Elson?

  After launching in 2020, the mother-daughter duo went on to raise $4 million in funding from investors including Andreessen Horowitz, and now works with over a dozen Fortune 500 companies to support their emerging leaders. This is my conversation with Jordan Taylor and Edith Cooper, the co-founders of Medley.

• 5:13Ed Elson?

  Jordan and Edith, thank you for joining.

• 5:15Speaker 04

  Thanks for having us.

• 5:16Ed Elson?

  So you are definitely the first mother-daughter duo that we've had on the program. We'll get into that relationship in a bit, but let's just start with the company. Jordan, what is Medley and what inspired you to start this company?

• 5:31Speaker 05

  Medley is an enterprise group coaching platform. So what does that mean? We work with large companies to design, launch, and scale group-based coaching programs, solving for connectivity in addition to leadership development. And our participants are usually people in their twenties, thirties, who are really looking to figure out their careers and how they want to lead and influence others. The idea for Medley was actually inspired by a course that I took in my last semester at Harvard Business School. It was called Authentic Leadership Development, and the class took place in small groups. So you're sitting with six people in a room for two hours every single week. It was completely transformative.

• 6:14Speaker 05

  I learned so much about myself, about other people, how to engage with them, my perspective was expanding. And after I did some digging, I realized that these small groups were actually...

• 6:27Speaker 05

  Everywhere. They were in a lot of different spaces, whether it was AA or Weight Watchers or religious constructs, even with executives, organizations like YPO existed and had a huge success. And so as I was thinking, okay, how could we build something where more people can access this meaningful growth experience? I had been keeping my mother in the loop and from the lens of I'm thinking about exploring this idea. I think there's something in groups, not sure what the business is. She had retired from Goldman Sachs about six months prior to one of these pivotal conversations. And she thought she was going to retire, join a couple of boards, spend a lot of

• 7:10Speaker 05

  time outside and with friends. And she actually called me after one of those updates and said, Jordan, I think we should be building Medley together.

• 7:19Ed Elson?

  Oh, wow.

• 7:20Speaker 05

  Yeah. So, you know, I think, did she know what it would be like to build a startup from scratch? No. To be fair, neither did I. But I think that's just been a highlight of the experience that I'm sure we'll delve more into. But, you know, we've been really working on the business together for the past five years.

• 7:41Ed Elson?

  My next question for you, Edith, was going to be, how did Jordan convince you? But it sounds like you didn't need much convincing.

• 7:47Speaker 04

  No, I really didn't because what she was focused on was something that had always mattered deeply to me as a business person, as a leader, and quite frankly, as a human. I had the good fortune and, shall we say, persistence to have worked in financial services for more than three decades. And my last job at Goldman Sachs was running human capital management, otherwise known as HR. That was an interesting time at Goldman. And it became very clear to me then, probably because it was my full time gig. But it'd always been clear that my job, our job as colleagues, as leaders, as people were to create

• 8:30Speaker 04

  an environment where people can really thrive, not just a certain type of person who can morph themselves into the mold of what had been successful before, but for a broad group of people who brought many talents to the organization. And so as Jordan and I were talking about the significance of learning how to show up for yourself in the context of others, that's how I think about groups and groups performance, it seemed like it was something that was so important and I wanted to join. I also wanted an opportunity to work closely with Jordan. You know, I'd been her mom since day one, but I saw the evolution of her approach to business and to commerce, and I thought I could learn a lot.

• 9:15Ed Elson?

  Yeah.

• 9:16Speaker 04

  And I certainly have.

• 9:18Ed Elson?

  How do these group lessons work? Is there a leader? Do people, is it sort of like a seminar? How does it work?

• 9:26Speaker 05

  So the way our methodology works, it is pretty far from a seminar. So we have coaches who lead every group session. So from a participant's standpoint, the first thing you do is you fill out our matching questionnaire and we match you to a group of other leaders who are experiencing similar challenges and are in a similar place in their careers and leadership journeys. The groups meet over the course of eight sessions, over the course of four to eight months. And so they're working with the same coach throughout, but it is very different and far from a typical training. You know, when you think about the training that you might have at your company, you might think of sitting in a big room, watching a big screen or watching a Zoom lesson.

• 10:08Ed Elson?

  A presentation.

• 10:09Speaker 05

  Yeah. No, this is incredibly interactive. Our coaches are really going deep with people. And our style really does incorporate the personal and the professional, because it's so clear now that there's just a blending that is a result of the world that we live in.

• 10:26Ed Elson?

  Edith, do you think that what you're providing now is missing? Based on your experience, you've worked at Goldman Sachs, you've also been on the boards of Etsy and Slack, you've now sat on the boards of Amazon and PepsiCo. Do you feel like what you're providing with Medley is missing from large enterprises, such as the ones you've worked at?

• 10:46Speaker 04

  I think that if you were to talk to most organizations, certainly the ones I've been involved in, and you asked, what really makes a difference to the culture? At some point, they would say cultural values, and they could name them, and they would say managers are important, leadership is important. But I would say historically, when you said, okay, what does that mean? You'd get a lot of different types of answers. Some people would say, oh, there's a lot of soft skills. You have to be approachable, accessible, et cetera. But what I'm seeing now, what we're seeing, is that what we used to think about as soft skills, listening, reacting, interpreting, understanding, are not actually soft at all.

• 11:29Speaker 04

  They are actually quite challenging. They're hard. And so what Medley does is it creates opportunities for people to show up in these small groups of six to eight people with a professional coach, to really put to practice how they show up as individuals for the benefit of themselves, but also the benefit of the group. What is a group? A group is a team. What is an organization? A bunch of different teams. And so it's been very, very exciting and rewarding to see the impact that we've made on the employee's experience. We work very hard to make sure that Medley is integrated into the overall talent framework, and we're excited about the forward.

• 12:12Ed Elson?

  By the way, I totally agree with that. My experience, my professional experience so far is that most of work is soft skills. Granted, I'm in a niche industry, but it's all, you're just working with people. So you've got to get along with people, and if you do that, my view is that you will succeed. But I'm wondering, having been basically global head of HR at Goldman, do you think that soft skills have historically been undervalued or underrated? Are soft skills kind of making a comeback at this point?

• 12:42Speaker 04

  People are showing up at work today. As humans, they are not as excited about leaving who they are behind. They want to be able to see leadership and be themselves authentic. And they want to be able to talk about not just what's going on in the day to day workplace, but what's going on everywhere else. And that's hard if you don't actually take the time to be intentional to learn how to listen to people, to figure out who is talking and who's not talking, to think about how to respond when you disagree with someone.

• 13:25Speaker 04

  And in an environment like this, where the pace of change is extraordinary, there's a lot going on in the world that presents interesting opportunities, but there are a lot of challenges, you've got to be able to do that. Those are not soft skills.

• 13:38Ed Elson?

  Yeah.

• 13:38Speaker 04

  You know, historically, if you are a deep subject matter expert, and it is probably still true in certain organizations, you can get along well. You really can. Deep, deep, deep understanding of your craft, whatever organization you work in. But what happens is, over time, as you get better and better and better, what do you get? More responsibility. And it's more responsibility for other human beings. And so Medley is an opportunity to give people the space to learn what that should feel like and how you should action it.

• 14:12Ed Elson?

  And it's a completely different job, right? Like, when you're a manager of a team, that's not the same as just being really good at, you know, being a great programmer. But it's strange that we have this system where if you get better at your vertical in a way, then you get more responsibility over people, but I guess you don't get taught how to manage people. I mean, if you could solve this problem, I would love this. I would love it if we could make everyone, if I could myself be an incredibly good listener, work well with people, and I could make everyone at my company be the same way. That would be a dream. But it seems very difficult to do. And I could imagine walking into one of these group coaching sessions.

• 14:56Ed Elson?

  And, you know, someone tells me, you got to get better at listening. I'd be like, OK, sure. How do you actually implement this? How do you actually coach this stuff? Which to me feels like more of a, you know, inherent trait in people.

• 15:11Speaker 05

  You know, I think certainly if the session was designed and you showed up and had said, all right, your growth area is listening, just listen better. Would not be incredibly effective. That said, if you shift the frame and really do accept that listening can be a skill you can practice, a group is an incredibly powerful space to practice that.

• 15:32Ed Elson?

  Right.

• 15:32Speaker 05

  Because imagine if you're working with a coach one on one. The coach can relay back, you know, I've heard in your feedback that sometimes you come across like you're not paying attention. Great. If you're in a group of eight other people and the coach is actually saying, Edith, how do you respond to what Ed just shared? It's putting you on the spot. It's creating that space for you in a pretty low risk environment to actively listen and to practice. And so, you know, in a group session, there is active role playing where we will do and practice listening or communicating, navigating conflict, those types of skills that are incredibly, incredibly difficult.

• 16:13Speaker 05

  I will also add that where we are from a technology standpoint presents a pretty exciting opportunity to make these skills much more tangible for people and actually build upon them in a way that people can measure and understand. And that's something that we're spending a lot of time on now is how do we take these skills like listening, giving feedback, influential communication, inclusive leadership? How do we take these skills and really make them measurable and understandable for both individuals and for companies?

• 17:08Scott Galloway?

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• 18:08Scott Galloway?

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• 19:19Scott Galloway?

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• 20:33Ed Elson?

  We're back with first-time founders. When I look at your resume, so you worked in consulting, you worked at Boston Consulting Group, you were a chief of staff at a successful startup, you went to Harvard Business School. You have kind of the perfect founder resume. Did you always know you wanted to start a company?

• 20:51Speaker 05

  I did not. I think, you know, my experience at Mike, which was a startup that I worked at prior to business school, really started to spark that interest. I was excited by the amount of ownership that you can have in building a business. I was excited by the genuine and authentic sense of teaming that you have with people who are all in it, you know, trying to do something crazy with each other. After I'd graduated, I did have a strong instinct of wanting to build a company. But I do want to go back to something you said. You know, on paper, I think I do have a resume that can scream, you know, entrepreneur. But Edith and I are a very atypical founding team.

• 21:36Speaker 05

  So, you know, firstly, we're mother daughter. Secondly, we're both black women. Third, we don't come from a technical background. Although I, you know, for the business that we're in, I will say our technical skills are quite relevant, just different. And so it's been interesting for us as we've, you know, built the business, grown the business, built a team, engaged with investors, engaged with enterprise level customers, figuring out our own style and actually figuring out how we can use our difference to our advantage.

• 22:08Ed Elson?

  Yeah, you launched in 2020. You've, as I mentioned, you raised this $4 million round. You're partnering with Fortune 500 companies. Take us through just the trajectory of the company so far. What have been some of the highlights, maybe some of the challenges? How has the company changed over the last four years?

• 22:28Speaker 05

  So we've had two big pivots. The first pivot was our original plan was to launch in April of 2020 as an in-person membership community for people looking to invest in their personal and professional growth. So if you can imagine a worse business to launch in April of 2020, where you bring people together

• 22:46Ed Elson?

  I just put that together.

• 22:49Speaker 05

  In small groups, closed environment, in a physical space. Medley is pretty much it, you know, the first iteration. And so we remember vividly in March, we had the coaches lined up. We were putting finishing touches on the office space for the space that we just signed. And we had to completely pivot to an online model. We had no idea if we could replicate that sense of connection, that impact, the dynamics with the coaches. We had no idea. And so we ended up regrouping, doing some online testing and launching Medley as a primarily online community in August of 2020. We then spent a couple of years building with individuals.

• 23:35Speaker 05

  Who recognized the need and who were excited to invest in their own leadership development. We had members from, I believe, 20 different countries around the world. We got a great amount of traction. And then towards the end of 22, we actually were getting market pull from organizations. So people were going back to their companies saying, I participated in this thing called Medley. I think other people here could benefit from it. And then we'd get emails from people in the talent side of organizations saying, hey, we'd like to learn more. And so it became really obvious at the beginning of last year that this was the huge opportunity for Medley. It was in helping

• 24:16Speaker 05

  large organizations connect and grow their emerging leaders and help solve for a few combining challenges that they're experiencing right now. It's been very exciting, although a challenging time to build a company, most definitely. But we definitely have enjoyed it.

• 24:36Speaker 04

  So why don't I add a couple of challenges?

• 24:40Speaker 04

  Pivoting is exciting, but it's also hard because you've invested in building the apparatus to support an in-person model. You incur the expenses associated with that, and then you don't need it anymore. That's challenge. The fundraising environment can be challenging. We were well positioned in our seed round with a terrific group of investors. We were marching towards, you know, the next raise in, was it the spring of last year? SVB, problematic.

• 25:24Speaker 04

  Problematic. Let's just say some of the people that, you know, we were in serious conversations with were very distracted. That's challenging. Fitting your business into the expectations of a certain type of funding.

• 25:41Speaker 04

  Can work, but it could also be challenging when the expectations shift. So when you move from growth at any cost with profitability not being important to an environment where people are focused on profitable growth and positive cash flow could be a challenge for us, it's been a real opportunity. Because our business has really grown as we've bought on more companies. So therefore, that kind of has swung back the other way. But I think the lesson that we've learned throughout all of this is that you have to be very focused on your customer.

• 26:25Speaker 04

  Make sure that you understand the value proposition that you're offering. And then be prepared to take in all that you learn from testing to adapt along the way. We often say we're flying a plane and, you know, we're changing the windows at the same time. Maybe that's not a very nice analogy, but nevertheless, you know, you've got to be, you know, you've got to be able to adapt. And I have to say, that's one of the things that I've had to really get used to because, you know, when you work in a large enterprise in financial services historically, you know, you have quarter to quarter earnings. There's a tremendous amount of focus on risk and risk management. And like, just give it a go and hopefully it works out.

• 27:10Speaker 04

  But, you know, when you're building something in a new category, you have to be willing to try things and some of those things will not work. Very different.

• 27:21Ed Elson?

  Yeah, sure. Huge mindset shift for you. I do want to shift to the mother-daughter dynamic. We'll start with you, Edith. What is it like starting a company and running a company with your daughter? What have been some of your main takeaways?

• 27:38Speaker 04

  I think that in the first instance, I got what I signed up for. I have always, always believed that the future is in the hands and in the minds of those that are coming up through, you know, schools, arriving in the workplace, et cetera. And I've gotten all of that. You know, she had a different way of thinking through opportunities. Our team is in the same genre and it's just been an incredible experience. It's a very trusting experience because, you know, we're related and I therefore don't have the, okay, well, what's happening with this person? Is she thinking this and the other?

• 28:22Speaker 04

  You know, there's that inherent trust. Right. I think that the challenges, though, are that in some ways, it feels like I'm getting, work is getting put before our life. Right. You know, so for example, Jordan calls me Edith and every now and then, outside of the workplace, she'll say, hey, Edith. I'm like, oh, no, no, no, no, no. This is a mom moment. Oh, so you switch? This is, she switches. And that's important for, from our colleagues' perspective. Oh, wow. So that's, that's been kind of interesting. And then the only other thing that I would add is that, you know, I have worked in large

• 29:04Speaker 04

  organizations and been responsible with incredible colleagues for many, many people. Big budgets, big opportunities, big challenges. And although I always prided myself in not being the decision maker, right? I always wanted everyone to own it and would step in when I needed to. At the end of the day, people knew that I was the decision maker and I was accountable, too. But working with Jordan, when we first got started, I didn't want that dynamic. She's the CEO, Jordan is the CEO of Medley, and I am the co-founder. And so there were many circumstances in the first months where we would be in meetings, and I wouldn't really say much.

• 29:49Speaker 04

  And I remember that meeting, Jordan, when we walked out, and you're like, why didn't you say anything? It's like, well, you're the CEO. It's like, yeah, but you know the topic. Can you just like jump on in there? And so it's been really great because I didn't want to be the over the top, you know, boss lady, you know? We're peers in this context. We're running this business and building this business together with our colleagues at Medley. And so that's been a bit of an adjustment, you know, to know that we are coming at things from different angles, and there are going to be moments where I'm going to take the lead, and that is the right way. It's kind of like what it's like in any organization, actually. But here, I was more sensitive to it than I had been if she were not my daughter.

• 30:30Ed Elson?

  I can imagine it's, yeah, way more sensitive. I would imagine it's more difficult. What's the experience been like for you, Jordan, as the daughter?

• 30:37Speaker 05

  It's been incredibly meaningful. You know, even just from the standpoint of growing up, my mom worked a ton. She had very, you know, high-powered jobs. And 10 a.m. on Tuesday, I was at school, she was at work, and we would reconnect when she came home from the office. Now, we start most of our days talking to each other. And it is a highlight when at 7:30 a.m., 7 a.m., 8 a.m., I get a call, are you awake?

• 31:08Speaker 04

  I still have bad habits. I start super early, and I still kid myself and think, you don't have to answer me right away at 6:30 a.m. So I work on that, but that's a hard one to break.

• 31:22Speaker 05

  But I will say, sometimes it's work, and sometimes it's not. And I have learned

• 31:29Speaker 05

  I've learned so much from getting to work with her. How to engage with people, how to listen to people, a lot of the skills we've been talking about earlier. My mind is often blown in meetings. Sometimes I leave the meeting and I'm like, how did you even see that? How did you know that this person was thinking XYZ to tee this up? It's absolutely incredible. So from a professional standpoint, I've learned a lot. And I will say also, from a personal standpoint, I've learned a lot by getting to see my mother in a, in a working environment and see how she handles stress from work that I'm, you know, very, very close to and juggles different priorities and is constantly prioritizing.

• 32:12Speaker 05

  And I think, you know, I will echo the challenge that she shared around creating space for work and life. You know, that is, is always difficult. We have built up enough trust now that if I say, I need, I need mom mode, or I need work mode, we're able to switch.

• 32:36Ed Elson?

  Is that what you say, mom mode, please?

• 32:37Speaker 05

  Yeah, I'm just like, can we just put Medley on pause for a second and talk about XYZ?

• 32:43Ed Elson?

  Yeah.

• 32:43Speaker 05

  So all in all, it's really enhanced our ability to communicate and we've gotten to know each other in a very different way. It's a very unique experience. And I'm excited for the future as we continue to grow the business and as both of our roles continue to evolve, to continue to learn.

• 33:02Ed Elson?

  The co-founder relationship is a very stressful and fraught one. I'm very close. And then the mother and child relationship is very close, trusting, loving, and also pretty fraught and stressful. Has there ever been a moment where the pressure of work has put a strain on your personal relationship in a, in a negative way at all?

• 33:26Speaker 05

  No.

• 33:27Ed Elson?

  I'm getting a shaking of the head. Do you agree?

• 33:29Speaker 04

  No, no, yeah.

• 33:30Speaker 05

  I don't think so. I'm resting my brain.

• 33:32Speaker 04

  Aggressively saying no.

• 33:34Ed Elson?

  No, it's perfect.

• 33:35Speaker 04

  Go, Jordan. Exactly.

• 33:38Ed Elson?

  Sorry, go ahead, Edith. Your answer was no.

• 33:40Speaker 04

  No, I just, first of all, we don't, we want to let it go there. You know, we, and it's not that we agree on everything. I think we're very conscious of being respectful of each other's opinions, taking into consideration the opinions of other people on the Medley team. And I honestly cannot think of a single time where it's gotten so challenging that I would sit and talk to my other two children or my husband about, you know, oh, my gosh, you know, this is just out of control, because we talk about it.

• 34:19Speaker 04

  See, that's the thing about being a related mother-daughter team, is that we really do, even when we're not agreeing on something, believe that we have the same goal. Yeah, I think that we work it through. What do you think?

• 34:36Speaker 05

  I would absolutely agree with that. And it doesn't mean, as Edith said, that we don't disagree about things, that there aren't moments of challenge or tension. In any healthy relationship, you're encountering all those things, right? You're encountering joy, you're encountering affection, you're encountering disagreement. But we do really have each other's best interests at heart. And I think that's important for any relationship period, but especially a co-founder relationship, if you have that level of trust and you know the other person is, you don't have any worries about the other person's intentions, you're able to communicate and navigate through different challenges.

• 35:16Speaker 05

  And it's really been a highlight of building the company, has been getting to work, to work with Edith, work with my mom. So it hasn't all been sunshine and roses, but we know each other so much better. We know like a third dimension of how we exist and how we operate, which is really fun.

• 35:38Ed Elson?

  It sounds like you both went into this kind of unusually skilled at the separation of work and life and making, you know, strategic decisions and separating that from your emotions. And, you know, you describe, you call Edith in certain situations, mom in certain situations.

• 35:59Speaker 04

  But

• 35:59Ed Elson?

  Did you know this going into it?

• 36:01Speaker 04

  No.

• 36:01Ed Elson?

  Or has this been a training program? How did you figure this all out?

• 36:04Speaker 04

  There's no playbook. There's no playbook for someone like myself, who worked in large institutions previously for 35 years, to roll up into an organization where it's Jordan and myself, sitting in a, you know, two-seater, because we didn't want to spend the money on a three-seater in a shared workspace. But you pay attention and you learn as you go. We were looking for our first analyst as an example. And there were so many things going on. It was really super early days. And Jordan looked at me, she said, she was calling me mom, there's only the two of us. And she says, Mom, you ran HR for a 35,000-person organization. You must know how to find candidates on LinkedIn.

• 36:47Speaker 04

  And I'm like, uh, that would be a no. I said, I could call somebody who can help me figure out candidates on LinkedIn. I'm willing to give it a go. But there were those moments of, oh, oh, yeah. You actually weren't operating yourself personally, every aspect of all of the roles for the last, I don't know, 15, 20 years. But we move forward and we sit together and, and, you know, we figure out how to, you know, leverage the platform or any other platforms, et cetera, et cetera. But, but there's a lot of that. Because what do I know? I know a lot about the things that I've experienced, as does Jordan.

• 37:31Speaker 04

  But I really respect that there's much in this construct of standing up medley from, from ground zero in a new category, working together as a mother-daughter, co-founder team. There's as much that we have to learn. And there is no playbook for that. There's no playbook.

• 37:53Speaker 05

  Yeah. That's one of the things we have most in common is our

• 38:00Speaker 05

  Voracious need to try to learn as much as we can in every context. We both fundamentally believe we can learn from any situation and from any person. And that shared value has enabled us to work through these types of things and build up that muscle of communicating with each other. And, you know, for myself, I take my, my growth as a founder, as a CEO, really seriously. I have had a coach, I've been in a group, a group of other founders, I have a therapist, I take my exercise, sleep, all that stuff pretty seriously. And so does Edith. She does not miss a workout, let me tell you, every day. She doesn't mess around.

• 38:41Speaker 05

  And I think that has been a huge enabler for us because it's not as though we showed up on day one and then just said, okay, let's see what happens. It actually was a super intentional process for both of us to always be trying to learn, to share feedback with each other, to invest in ourselves and invest in each other.

• 39:00Speaker 04

  But this concept of there is no playbook is, I think, becoming the norm, not just for, for founders, but for any organization that wants to be relevant today and into the future. What is the playbook? You know, what is the playbook when a new drug changes the consumer appetite? You know, what is the playbook when technology that has been around for decades explodes into this new incredible world of, of machine learning and AI? What is the playbook for next year, let alone, you know, for the next 10 years? And so I think that much of our experiences are similar to what we are talking with

• 39:43Speaker 04

  the organizations that we're working with about. You know, when you, when you think about what it takes to really build sustainably, you know, important organizations, you've got to really have a culture that enables people to connect how they operate, how they interact, all those things that we were talking about with respect to listening and communicating, et cetera. To the ultimate goal, right? So if everybody walked out of the room and says, I feel really heard and I feel like included, but you have no idea like what you're supposed to be delivering and how you're supposed to deliver it. That's not the point of all of this. The point of all of this is to really appreciate the fact that in a, in any kind of a business

• 40:26Speaker 04

  environment with a playbook, maybe known today and not, you've got to have intellectual versatility to operate and to engage in a very meaningful and steady, quick way. And that's what's super exciting for me about sort of reinventing myself into a founder.

• 40:49Speaker 04

  We'll be right back.

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• 43:13Ed Elson?

  We're back with first-time founders. I'm sure this has taught you a lot about business, as we've just learned. I'm sure it's taught you a lot about motherhood, too, I could imagine. I'm wondering if you've learned anything new about what it means to be a mother, having done this. Is there something you know now about motherhood that maybe you didn't know before you started this?

• 43:41Speaker 04

  Now, that is an unexpected question. So, good job. I think it's something that I knew, but I would say has been accelerated to sort of the top of my consciousness. And that is, you have to be present. You know? And I think throughout the years, I have three children, Jordan's the oldest, I have two boys. You know, as Jordan described, a pretty intense professional existence. And as time went by and I got more ownership of my schedule, et cetera...

• 44:22Speaker 04

  I would show up like from Mars, it seems sometimes. Like, my longest trip was from New Zealand to Providence, Rhode Island, to see my son play soccer.

• 44:34Speaker 04

  But I would say that sometimes I was there and I could have been more present. But I was doing the best I could and I was giving myself high marks. I just shared this story. Isn't that incredible? I traveled all the way around the world. But I do think that, that I've learned, particularly because we have to be very deliberate about the separation of work and our lives, that when Jordan says, oh, can I just talk to you about a few things that are not like, that is focused time. Right. That is really focused time. And when I hear, you know, I'm, I'm not having a good, you know, morning,

• 45:19Speaker 04

  I have to really respect that in a different way. Right. You know, I'm kind of a, let's go, let's like push through. And I think that's a good lesson for motherhood, that, you know, you want to have that relationship where when someone, when your child says, you know, I'm, I'm struggling with something, that you don't try to fix it. Because I'm a fixer, right? And so that I've learned a lot with working with Jordan and Natalie, that when she asks me a question about life or work, she's actually, most of the time, not asking me for the answer. Right. Right? She's asking for an opportunity to talk it through.

• 46:04Speaker 04

  In fact, just the other day, you're like, listen, listen, I just want to talk it through. I'm not asking you to do it. I just want to, because I'm like, okay, I got this. She's like, no, you don't. Yeah. I need to talk. I've been studying this. Yes. For a long time. Yes. So those are, that was a really interesting question.

• 46:23Speaker 05

  And I'll add, I'm, I'm expecting, we're expecting our first child in the fall and we're having a girl, so this will be really funny. I don't think she can work in the business quite yet, but just give her a couple of years. It'll be a three-generation business. And I will say, the thing that I'm trying to embrace entering this huge life transition is just the unpredictability of everything. You know, I, I mean, I have gotten so much more comfortable with. Both ambiguity, so looking into the future and not knowing exactly what it's going to look like. And also, just the lack of control that we really have over things. You don't think that you start a fundraiser process and then Silicon Valley Bank is going to collapse.

• 47:07Speaker 05

  You don't think you're going to launch an in-person community and then COVID-19 happens. You just don't think that's going to happen. But that's life, right? Life is pretty unpredictable. And I've built up a lot of confidence, my ability to just navigate unexpected situations. And I think, I think that will help me in parenting. Because from what I can tell and seeing my friends and even seeing, you know, in my family with my siblings and my cousins, you don't know what the child's going to be like. You don't know what life's going to give you. And part of that is, is part of the fun, I would say. So I'm looking forward to that.

• 47:43Ed Elson?

  Do you have any, like, hard boundaries? Like, you know, don't text me at this time or anything like that?

• 47:49Speaker 04

  I try not to engage, and in fact, I don't actually engage with Jordan about work on Sunday afternoon at four o'clock. That was a really bad habit I had because the cadence of the week gets started, I get myself organized. And, you know, I've done that for 35 years. So it was a hard thing to break. And it was very disruptive, actually, to Jordan and her husband and quite frankly, everyone around me. So, you know, and for me, that's a, that's a hard rule. We were joking earlier about the 6:30 text. I don't really do that, that often. I get up sometimes at five o'clock in the morning.

• 48:33Speaker 04

  I don't do that because that's a drag. You know, you get up, whatever time you get up, you see this text, you like, don't even have your mind right. You gotta like, you know, so that's a pretty hard rule, too. Like, if I've got something that really needs to have a conversation. I don't put it in a text at seven in the morning. And I'll say, hey, give me a call when you can. And the other thing I think is very important in this conversation about first time founders is that people are watching you, whether you have three people, 10 people, 20 people, whatever the number is. People do care about the balance that they have in their lives more every, every year.

• 49:17Speaker 04

  And I think that's really important and it matters. And so therefore, you know, I, I can get pretty intense. Jordan can get pretty intense. And quite frankly, most of the people on our team can. But I really have watched very closely how Jordan has been very clear and respectful of people and their lives. And so that when someone is on holiday and hasn't been on holiday and is really delivered, she will literally say, okay, anything that's going, you know, to this person, you know, is going to go into an inbox, I'll be watching the inbox, just so you know.

• 49:56Ed Elson?

  And that's different from the Goldman style.

• 49:59Speaker 04

  Perhaps, yes. But you know, the interesting question is, what is it like? I haven't been in Goldman for, you know, six years now, almost. What is it like now, perhaps? And there were moments then where, you know, there was no working for investment banking on Saturdays and whatever the case may be. But all of this is in response to the reality of who's showing up. And people show up wanting to be human beings with work being part of their existence, not their only existence.

• 50:31Ed Elson?

  I'm going to shift to a quick lightning round here about organizational management, which I feel like you both are experts. So I'm just going to throw you some questions and we'll get your hot takes on some of these. So we'll start with Edith. How can companies make meetings more productive?

• 50:47Speaker 04

  Make sure there's a clear agenda. Hope people accountable for doing the work before they come to the meeting. And as participants in the meeting, keep it concise, not my specialty. So I, I'll work on that. And pay attention to who talks and who doesn't talk. Clear follow ups to conclude.

• 51:11Ed Elson?

  Jordan, is remote work overrated or underrated?

• 51:14Speaker 05

  Personally, overrated.

• 51:16Speaker 05

  But flexibility, I will say, is really what's valued from what we're seeing in terms of remote work.

• 51:24Speaker 04

  Good concise answer. That's good. Let me see what I can do.

• 51:27Ed Elson?

  She's learning from the master.

• 51:31Ed Elson?

  Edith, what is the best way to measure employee success at a company?

• 51:35Speaker 04

  The productivity of the company, not just in terms of the bottom line, but in terms of what the reputation of the company is and how they deliver that profitability. That's employee success, right? That doesn't happen without employees being successful.

• 51:54Ed Elson?

  Jordan, when it comes to decision making, do you prefer using your instincts or data?

• 51:58Speaker 05

  Data. But Edith prefers instincts.

• 52:02Ed Elson?

  Okay.

• 52:02Speaker 05

  So we are a great match in that regard.

• 52:05Ed Elson?

  Okay. Why are you pro data? Why is Edith pro instincts?

• 52:09Speaker 05

  You know, I think for me, data is more my natural approach, although at this point, I've really been working on this. I actually do try to make decisions based off of instinct more. And the way I describe instinct is that it's actually a cumulation of your experiences. So instincts are informed by data. But I think to start, you know, my natural inclination is, well, I want to understand and get all the information. But when you're running a startup and over the past five years, I've learned you really can get all the information. So you have to use both.

• 52:46Ed Elson?

  Edith, how important is DEI? And do you think it's something that every company should be implementing?

• 52:52Speaker 04

  Every company that wants to be a relevant company needs to invest in their people and create environments where everyone can thrive. And that's everyone. That's people who are part of the majority, people who are from different schools, from different languages, cultures, et cetera. Many people have asked me, particularly in the last year, what's going to happen with DEI? Is it going to be over forever? And it's like, I don't know. Do you want to be an excellent company? If you want to be an excellent company, you continue to do the work. You can call it what you want. You have to do the work.

• 53:30Ed Elson?

  Do you think it's been politicized in a way that's been destructive to organizations?

• 53:37Speaker 04

  I think that it has certainly been politicized. And I

• 53:44Speaker 04

  Don't think it has been particularly productive. I don't think it's been as disruptive as people might think. Right. Because strong organizations with strong cultures understand how important it is to extract excellence. And people ask me, what should we call it? I says, why don't you just call it excellence? Because that's what it means to have a truly diverse organization from a number of different perspectives. So, you know, all the organizations that I've worked with and will continue to talk to, they're moving forward because they want to be great.

• 54:26Speaker 04

  And to be great, you have to have the diversity of experience, perspectives, culture, sexual orientation. The list will just continue to get longer and longer. What an exciting opportunity.

• 54:39Ed Elson?

  Jordan, this one came to me because we were discussing the idea of bringing your full self to work. Is there space for political opinions in the workplace? And should leaders be taking up political opinions if they choose?

• 54:57Speaker 05

  It really depends on the company and their culture and their values. So for some companies who have made statements that they do not want to engage in the political dynamic, those companies are going to attract people who want to work in those environments. On the flip side, companies where leaders really are taking a stand, are voicing their opinion in whichever direction, the same thing is happening, right? People are going to be drawn to working at those companies because that's a value that they care about. And so, you know, personally, I think that there needs to be a way for leaders to acknowledge what's happening in the world and give space for employees who are probably processing in some way or the other.

• 55:40Speaker 05

  That's what we try to do internally at Medley is really just giving space for people. But I do think that we're just going to see some real self-selection in terms of employees and they'll vote by going where they want to work.

• 55:52Ed Elson?

  Final questions from me, and thank you both for being generous with your time. Edith, actually, we'll start with Jordan. Some advice to our listeners. We have a lot of female listeners on this show. Scott seems to think we don't, but we do.

• 56:12Ed Elson?

  Do you have any advice on how to be a good daughter?

• 56:15Speaker 05

  I will say, as you grow up and as you encounter different experiences, embrace the fact that your relationship with your mom might change. And that can be exciting, can be a good opportunity.

• 56:28Speaker 05

  Or your dad. Yes, you're right. Or your dad, with your parents. Embrace this fact that your relationship with your parents likely will change over time. And I think accepting that can really enable new types of relationships to build with your parents.

• 56:44Ed Elson?

  And Edith, any advice on how to be a good mother?

• 56:47Speaker 04

  Not to get a little syrupy here, but love unconditionally because it's a ride. And if, if you make that the core of your relationship, it becomes multi-dimensional. It becomes, you know, positive reinforcement, feedback, direction, and just some good hugs from time to time. It'll all be okay. But if you start with that center and you develop trust of caring, anything that comes your way, you'll be able to navigate and things will come your way.

• 57:29Ed Elson?

  Love that. Jordan Taylor and Edith Cooper are the co-founders of Medley, a group coaching platform. Thank you very much, both for joining me.

• 57:36Speaker 05

  Thanks for having us.

• 57:42Ed Elson?

  Our producer is Claire Miller, our associate producer is Alison Weiss, and our engineer is Benjamin Spencer. Catherine Dillon is our executive producer. Thank you for listening to First Time Founders from the Vox Media Podcast Network. Tune in tomorrow for Prof G Markets.

• 58:15Speaker 10

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