AI transcript
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0:00:37 Hey, I’m Jon Collin Hill, host of a brand new show from Vox called Explain It To Me.
0:00:40 This week, the ethical murkiness of zoos.
0:00:46 Do we as humans feel like we deserve to just be able to walk around and see these animals?
0:00:48 Maybe we don’t deserve that.
0:00:51 Maybe there’s just some animals we don’t get to see.
0:00:53 To zoo or not to zoo?
0:00:55 That’s this week on Explain It To Me.
0:01:02 Listen wherever you get your podcasts.
0:01:07 Scott, what would be your advice to someone who wanted to start a company with a family member?
0:01:12 First, first word that came into my mind was don’t.
0:01:17 Look, I just think it’s situational.
0:01:21 It’s it’s so much of resting on the family dynamic.
0:01:28 I mean, I always thought I would never want to leave my kids a lot of money and I wouldn’t
0:01:31 want to work with my kids because I enjoy my relationship so much with them that I’d
0:01:36 hate if we didn’t get along professionally that it could put strain on the relationship
0:01:37 itself.
0:01:40 But at the same time, I also love the idea of building something that I could give to my
0:01:46 kids that they could that they could enjoy and build and family businesses.
0:01:50 A lot of people, you know, there’s a lot of family businesses and for a lot of people,
0:01:52 I think they’re very rewarding.
0:01:53 I just think it’s situational.
0:01:58 If two brothers get together and they have an idea for something, I get it.
0:02:03 I would think, and maybe this is because I’m not very close with my family, I was close
0:02:08 with my mother, but I hate having that many eggs in one basket.
0:02:13 It’s just the idea of adding another potential point of dysfunction where you start a business
0:02:15 together and it doesn’t work.
0:02:16 I just think it’d be devastating.
0:02:22 Like, if I started a business with my son and it didn’t work, right, and it put tension
0:02:26 on the relationship, that would be heartbreaking for me.
0:02:31 So what I would suggest is that if you are thinking about a business with a family member
0:02:36 that you immediately have an informal board of directors and that is someone outside of
0:02:42 the family that you both trust that can serve as a fiduciary for kind of coaching you around
0:02:48 issues, because it’s one thing if your business goes bad, but to strain a relationship in
0:02:51 a family, I think it would just be devastating.
0:02:56 I knew one of the nephews and nieces, one of the privileged jerks of the Bronfman family,
0:03:01 and I remember I had to share with them in the Hamptons, and this person was shitposting
0:03:03 Edgar because he’d lost so much money.
0:03:06 I’m confused why a Bronfman was in a sharehouse.
0:03:07 Yeah.
0:03:08 Sorry, go ahead.
0:03:09 He was in a sharehouse.
0:03:10 Yeah.
0:03:11 Yeah.
0:03:12 He had hot friends.
0:03:17 Anyways, but I remember her just talking so much shit about Edgar because he bought
0:03:21 some company and turned $8 billion of their fortune into a billion.
0:03:22 I don’t know.
0:03:26 It just feels, and then, you know, my entire insight into a family business is succession
0:03:31 and they all look fucked up and like they hate each other, so my general instinct is
0:03:38 I don’t want to say never, but I think you’re better off doing it with friends because I’m
0:03:41 still close with my initial business partner.
0:03:42 No, it’s not true.
0:03:44 We’re still friends, but we’re not close.
0:03:47 We just had a different approach to business over time, and while we’re still friends,
0:03:49 I invest in his companies.
0:03:53 I know I could count on him for anything, and he knows he could count on me.
0:03:57 But if we were like brothers, and there was sort of that what I’ll call easing back from
0:04:03 the relationship, I think it would put a strain on our brotherhood, and I just, I think family’s
0:04:04 so precious.
0:04:13 My initial inclination is tread carefully around that.
0:04:15 Welcome to First Time Founders.
0:04:20 Since COVID-19, the dynamics of the workplace have significantly shifted.
0:04:24 Nearly half of Americans today feel unsatisfied with their jobs, and more than half feel they
0:04:27 are lacking in professional growth.
0:04:29 Companies meanwhile have done little to address this.
0:04:35 83% of companies say developing leaders is important, but only 5% have actually developed
0:04:37 leadership programs.
0:04:41 My next guest, while at business school, came up with an idea to address the problem, an
0:04:45 online platform for group-based leadership development and coaching.
0:04:49 And to get this idea off the ground, she tapped a veteran, her co-founder as a former partner
0:04:54 at Goldman Sachs, a current board member of Amazon and PepsiCo, and also happens to be
0:04:56 her mother.
0:05:01 After launching in 2020, the mother daughter duo went on to raise $4 million in funding
0:05:05 from investors, including Andreessen Horowitz, and now works with over a dozen Fortune 500
0:05:08 companies to support their emerging leaders.
0:05:15 This is my conversation with Jordan Taylor and Edith Cooper, the co-founders of Medley.
0:05:17 Jordan and Edith, thank you for joining.
0:05:19 Thanks for having us.
0:05:24 So you are definitely the first mother daughter duo that we’ve had on the program.
0:05:29 We’ll get into that relationship in a bit, but let’s just start with the company.
0:05:33 Jordan, what is Medley and what inspired you to start this company?
0:05:36 Medley is an enterprise group coaching platform.
0:05:37 So what does that mean?
0:05:43 We work with large companies to design, launch, and scale group-based coaching programs, solving
0:05:47 for connectivity in addition to leadership development.
0:05:52 And our participants are usually people in their 20s, 30s who are really looking to figure
0:05:57 out their careers and how they want to lead and influence others.
0:06:02 The idea for Medley was actually inspired by a course that I took in my last semester
0:06:03 at Harvard Business School.
0:06:09 It was called Authentic Leadership Development, and the class took place in small groups.
0:06:14 So you’re sitting with six people in a room for two hours every single week.
0:06:16 It was completely transformative.
0:06:21 I learned so much about myself, about other people, how to engage with them.
0:06:24 My perspective was expanding.
0:06:29 And after I did some digging, I realized that these small groups were actually everywhere.
0:06:34 They were in a lot of different spaces, whether it was AA or Weight Watchers or religious
0:06:40 constructs, even with executives, organizations like YPO existed and had a huge success.
0:06:45 And so as I was thinking, okay, how could we build something where more people can access
0:06:53 this meaningful growth experience? I had been keeping my mother in the loop and from the
0:06:58 lens of thinking about exploring this idea, I think there’s something in groups.
0:07:00 Not sure what the business is.
0:07:08 She had retired from Goldman Sachs about six months prior to one of these pivotal conversations.
0:07:13 And she thought she was going to retire, join a couple of boards, spend a lot of time outside
0:07:16 and with friends.
0:07:20 And she actually called me after one of those updates and said, “Jordan, I think we should
0:07:22 be building Medley together.”
0:07:23 Oh, wow.
0:07:24 Yeah.
0:07:25 Okay.
0:07:29 So I think, did she know what it would be like to build a startup from scratch?
0:07:30 No.
0:07:34 To be fair, neither did I.
0:07:38 But I think that’s just been a highlight of the experience that I’m sure we’ll delve
0:07:39 more into.
0:07:40 Yeah.
0:07:44 We’ve been really working on the business together for the past five years.
0:07:48 My next question for you, Edith, was going to be how did Jordan convince you, but it
0:07:50 sounds like you didn’t need much convincing.
0:07:56 No, I really didn’t because what she was focused on was something that had always mattered
0:08:01 deeply to me as a business person, as a leader, and quite frankly, as a human.
0:08:09 I had the good fortune and shall we say, persistence to have worked in financial services for more
0:08:11 than three decades.
0:08:16 And my last job at Goldman Sachs was running human capital management, otherwise known
0:08:17 as HR.
0:08:20 That was an interesting time at Goldman.
0:08:26 And it became very clear to me then, probably because it was my full-time gig, but it always
0:08:34 been clear that my job, our job as colleagues, as leaders, as people were to create an environment
0:08:38 where people can really thrive, not just a certain type of person who can morph themselves
0:08:43 into the mold of what had been successful before, but for a broad group of people who
0:08:46 brought many talents to the organization.
0:08:51 And so as Jordan and I were talking about the significance of learning how to show up
0:08:57 for yourself in the context of others, that’s how I think about groups and groups performance.
0:09:01 It seemed like it was something that was so important and I wanted to join.
0:09:07 And I also wanted an opportunity to work closely with Jordan.
0:09:15 I’d been her mom since day one, but I saw the evolution of her approach to business
0:09:19 and to commerce, and I thought I could learn a lot.
0:09:21 And I certainly have.
0:09:24 How do these group lessons work?
0:09:25 Is there a leader?
0:09:28 Do people, is it sort of like a seminar?
0:09:29 How does it work?
0:09:33 So your methodology works, it is pretty far from a seminar.
0:09:36 So we have coaches who lead every group session.
0:09:40 So from a participant standpoint, the first thing you do is you fill out our matching
0:09:44 questionnaire and we match you to a group of other leaders who are experiencing similar
0:09:49 challenges and are in a similar place in their careers and leadership journeys.
0:09:54 The groups meet over the course of eight sessions, over the course of four to eight months.
0:10:01 So they’re working with the same coach throughout, but it is very different and far from a typical
0:10:02 training.
0:10:06 You know, when you think about the training that you might have at your company, you might
0:10:10 think of sitting in a big room, watching a big screen or watching a Zoom lesson.
0:10:11 Yeah, a presentation.
0:10:12 Yeah.
0:10:14 No, this is incredibly interactive.
0:10:19 Our coaches are really going deep with people and our style really does incorporate the
0:10:23 personal and the professional because it’s so clear now that there’s just a blending
0:10:28 that is a result of the world that we live in.
0:10:34 Edith, do you think that what you’re providing now is missing based on your experience, you
0:10:39 know, you’ve worked at Goldman Sachs, you’ve also been on the boards of Etsy and Slack,
0:10:44 you now sit on the boards of Amazon and PepsiCo, do you feel like what you’re providing with
0:10:49 Medley is missing from large enterprises such as the ones you’ve worked at?
0:10:53 I think that if you were to talk to most organizations, certainly the ones I’ve been
0:10:58 involved in, and you asked what really makes a difference to the culture, at some point
0:11:02 they would say cultural values and they could name them and they would say managers are
0:11:05 important, leadership is important.
0:11:10 But I would say historically, when you said, okay, what does that mean?
0:11:14 You’d get a lot of different types of answers.
0:11:16 Some people would say, oh, there’s a lot of soft skills.
0:11:22 You have to, you know, be approachable, accessible, et cetera, but what I’m seeing now, what we’re
0:11:29 seeing is that what we used to think about as soft skills, listening, reacting, interpreting,
0:11:32 understanding, are not actually soft at all.
0:11:36 They are actually quite challenging.
0:11:37 They’re hard.
0:11:42 And so what Medley does is it creates opportunities for people to show up in these small groups
0:11:47 of six to eight people with a professional coach to really put to practice how they show
0:11:53 up as individual for the benefit of themselves, but also the benefit of the group.
0:11:54 What is a group?
0:11:55 A group is a team.
0:11:57 What is an organization?
0:11:59 A bunch of different teams.
0:12:05 And so it’s been very, very exciting and rewarding to see the impact that we’ve made on the
0:12:07 employees experience.
0:12:12 We’ve worked very hard to make sure that Medley is integrated into the overall talent framework
0:12:15 and we’re excited about the forward.
0:12:17 And by the way, I totally agree with that.
0:12:22 My experience, my professional experience so far is that most of work is soft skills.
0:12:26 Granted, I’m in a kind of niche industry, but it’s all you’re just working with people.
0:12:28 So you’ve got to get along with people.
0:12:31 And if you do that, my view is that you will succeed.
0:12:37 But I’m wondering, you know, having been basically global head of HR at Goldman, do you think
0:12:43 that soft skills have historically been undervalued or underrated or soft skills kind of making
0:12:45 a comeback at this point?
0:12:49 People are showing up at work today as humans.
0:12:54 They are not as excited about leaving who they are behind.
0:13:01 They want to be able to see leadership and be themselves authentic.
0:13:08 And they want to be able to talk about not just what’s going on in the day-to-day workplace,
0:13:11 but what’s going on everywhere else.
0:13:17 And that’s hard if you don’t actually take the time to be intentional to learn how to
0:13:24 listen to people, to figure out who is talking and who’s not talking, to think about how
0:13:28 to respond when you disagree with someone.
0:13:32 And an environment like this where the pace of change is extraordinary, there’s a lot
0:13:37 going on in the world that presents interesting opportunities, but there are a lot of challenges.
0:13:39 You’ve got to be able to do that.
0:13:40 Those are not soft skills.
0:13:47 Historically, if you are a deep subject matter expert, and it is probably still true in certain
0:13:48 organizations, you can get a long way.
0:13:54 You really can, deep, deep, deep understanding of your craft, whatever organization you work
0:13:55 in.
0:14:00 But what happens is over time, as you get better and better and better, what do you get?
0:14:06 More responsibility, and it’s more responsibility for other human beings.
0:14:12 And so medley is an opportunity to give people the space to learn what that should feel like
0:14:14 and how you should action it.
0:14:16 And it’s a completely different job, right?
0:14:22 When you’re a manager of a team, that’s not the same as just being really good at being
0:14:23 a great programmer.
0:14:28 But it’s strange that we have this system where if you get better at your vertical in
0:14:31 a way, then you get more responsibility of the people, but I guess you don’t get taught
0:14:34 how to manage people.
0:14:37 I mean, if you could solve this problem, I would love this.
0:14:44 I would love it if I could myself be an incredibly good listener, work well with people, and
0:14:46 I could make everyone at my company be the same way.
0:14:49 That would be a dream.
0:14:52 But it seems very difficult to do.
0:15:00 And I could imagine walking into one of these group coaching sessions, and you know, someone
0:15:05 tells me you got to get better at listening, and I’m like, okay, sure, how do you actually
0:15:06 implement this?
0:15:12 How do you actually coach this stuff, which to me feels like more of an inherent trait
0:15:13 in people?
0:15:18 You know, I think certainly if the session was designed and you showed up and it said,
0:15:23 all right, your growth area is listening, just listen better, would not be incredibly
0:15:25 effective.
0:15:31 That said, if you shift the frame and really do accept that listening can be a skill you
0:15:35 can practice, a group is an incredibly powerful space to practice that.
0:15:40 Because imagine if you’re working with a coach one-on-one, the coach can relay back,
0:15:44 you know, I’ve heard in your feedback that sometimes you come across like you’re not
0:15:45 paying attention.
0:15:46 Great.
0:15:52 If you’re in a group of eight other people, and the coach is actually saying, Edith, how
0:15:56 do you respond to what Ed just shared, it’s putting you on the spot.
0:16:01 It’s creating that space for you in a pretty low-risk environment to actively listen and
0:16:02 to practice.
0:16:07 And so, you know, in a group session, there is active role-playing where we will do and
0:16:14 practice listening or communicating, navigating conflict, those types of skills that are incredibly,
0:16:16 incredibly difficult.
0:16:21 I will also add that where we are from a technology standpoint presents a pretty exciting opportunity
0:16:26 to make these skills much more tangible for people and actually build upon them in a way
0:16:28 that people can measure and understand.
0:16:32 And that’s something that we’re spending a lot of time on now, is how do we take these
0:16:39 skills like listening, giving feedback, influential communication, inclusive leadership, how do
0:16:45 we take these skills and really make them measurable and understandable for both individuals
0:16:47 and for companies?
0:17:10 I’ll be right back.
0:17:14 When Kamala Harris and Donald Trump met on the debate stage, it was obvious that these
0:17:16 were two very different people.
0:17:19 But JD Vance and Tim Walls actually have a lot in common.
0:17:21 They’re both white men from the Midwest.
0:17:24 They’re both family men, and they were both in the service.
0:17:27 But they disagree on what it means to be a man.
0:17:28 Here’s my light pack.
0:17:32 Surround yourself with smart women and listen to them, and you’ll do just fine.
0:17:35 Today Explained, every weekday, wherever you get your podcasts.
0:17:50 We’re back with First Time Founders.
0:17:55 When I look at your resume, so you worked in consulting, you worked at Boston Consulting
0:17:56 Group.
0:17:58 You were a chief of staff and a successful startup.
0:18:00 You went to Harvard Business School.
0:18:03 You have kind of the perfect founder resume.
0:18:05 Did you always know you wanted to start a company?
0:18:06 I did not.
0:18:13 I think my experience at Mike, which is the startup that I worked at prior to business
0:18:18 school, really started to spark that interest.
0:18:24 I was excited by the amount of ownership that you can have in building a business.
0:18:28 I was excited by the genuine and authentic sense of teaming that you have with people
0:18:32 who are all in it, trying to do something crazy with each other.
0:18:39 After I’d graduated, I did have a strong instinct of wanting to build a company, but I do want
0:18:41 to go back to something you said.
0:18:47 On paper, I think I do have a resume that can scream entrepreneur, but Edith and I are
0:18:50 a very atypical founding team.
0:18:56 Firstly, we’re mother-daughter, secondly, we’re both black women, third, we don’t come
0:18:58 from a technical background.
0:19:04 Although, for the business that we’re in, I will say our technical skills are quite
0:19:07 relevant, just different.
0:19:12 It’s been interesting for us as we’ve built the business, grown the business, built a
0:19:17 team, engaged with investors, engaged with enterprise-level customers, figuring out our
0:19:23 own style, and actually figuring out how we can use our difference to our advantage.
0:19:30 You launched in 2020, as I mentioned, you raised this $4 million round, you’re partnering
0:19:32 with Fortune 500 companies.
0:19:36 Take us through just the trajectory of the company so far.
0:19:39 What have been some of the highlights, maybe some of the challenges?
0:19:42 How has the company changed over the last four years?
0:19:44 We’ve had two big pivots.
0:19:51 The first pivot was our original plan was to launch in April of 2020 as an in-person
0:19:55 membership community for people looking to invest in their personal and professional
0:19:56 growth.
0:20:01 If you can imagine a worse business to launch in April of 2020, where you bring people together
0:20:08 in small groups, in small groups, closed environment, in a physical space, Medley’s
0:20:11 pretty much it, the first iteration.
0:20:17 We remember vividly in March, we had the coaches lined up, we were putting finishing touches
0:20:23 on the office space for the space that we just signed, and we had to completely pivot
0:20:25 to an online model.
0:20:31 We had no idea if we could replicate that sense of connection, that impact, the dynamics
0:20:33 with the coaches.
0:20:34 We had no idea.
0:20:41 And so we ended up regrouping, doing some online testing, and launching Medley as a primarily
0:20:45 online community in August of 2020.
0:20:51 We then spent a couple of years building with individuals who recognized the need and who
0:20:55 were excited to invest in their own leadership development.
0:20:59 We had members from, I believe, 20 different countries around the world.
0:21:02 We got a great amount of traction.
0:21:08 And then towards the end of ’22, we actually were getting market pull from organizations.
0:21:11 So people were going back to their companies saying, “I participated in this thing called
0:21:12 Medley.”
0:21:15 I think other people here could benefit from it.
0:21:20 And then we’d get emails from people in the talent side of organizations saying, “Hey,
0:21:22 we’d like to learn more.”
0:21:28 And so it became really obvious at the beginning of last year that this was the huge opportunity
0:21:29 for Medley.
0:21:36 It was in helping large organizations connect and grow their emerging leaders, and help
0:21:41 solve for a few combining challenges that they’re experiencing right now.
0:21:49 It’s been very exciting, although a challenging time to build a company, most definitely,
0:21:51 but we definitely have enjoyed it.
0:21:54 So why don’t I add a couple of challenges?
0:22:01 Pivoting is exciting, but it’s also hard because you’ve invested in building the apparatus
0:22:04 to support an in-person model.
0:22:10 You incur the expenses associated with that, and then you don’t need it anymore.
0:22:19 This challenge, the fundraising environment can be challenging.
0:22:27 We were well-positioned in our seed round with a terrific group of investors.
0:22:40 We were marching towards the next raise in, was it the spring of last year, SVB, problematic.
0:22:46 Just say some of the people that we were in serious conversations with were very distracted.
0:22:48 That’s challenging.
0:22:57 Fitting your business into the expectations of a certain type of funding can work, but
0:23:02 it could also be challenging when the expectations shift.
0:23:10 So when you move from growth at any cost with profitability not being important to an environment
0:23:19 where people are focused on profitable growth and positive cash flow, could be a challenge
0:23:20 for us.
0:23:27 It’s been a real opportunity because our business has really grown as we’ve bought on more companies.
0:23:32 So therefore, that has swung back the other way, but I think the lesson that we’ve learned
0:23:39 throughout all of this is that you have to be very focused on your customer.
0:23:46 Make sure that you understand the value proposition that you’re offering, and then be prepared
0:23:52 to take in all that you learn from testing to adapt along the way.
0:23:57 You often say we’re flying the plane and we’re changing the windows at the same time.
0:24:05 Maybe that’s not a very nice analogy, but nevertheless, you’ve got to be able to adapt.
0:24:10 I have to say, that’s one of the things that I’ve had to really get used to because when
0:24:15 you work in a large enterprise in financial services historically, you have quarter to
0:24:18 quarter earnings.
0:24:23 These are tremendous amount of focus on risk and risk management, and just give it a go
0:24:25 and hopefully it works out.
0:24:31 But when you’re building something in a new category, you have to be willing to try things
0:24:34 and some of those things will not work.
0:24:35 Very different.
0:24:38 Yeah, I’m sure a huge mindset shift for you.
0:24:43 I do want to shift to the mother-daughter dynamic.
0:24:45 We’ll start with you, Edith.
0:24:50 What is it like starting a company and running a company with your daughter?
0:24:53 What have been some of your main takeaways?
0:24:58 I think that in the first instance, I got what I signed up for.
0:25:07 I have always, always believed that the future is in the hands and in the minds of those
0:25:13 that are coming up through schools, arriving in the workplace, et cetera, and I’ve gotten
0:25:14 all of that.
0:25:19 We had a different way of thinking through opportunities.
0:25:26 Our team is in the same genre and it’s just been an incredible experience.
0:25:34 It’s a very trusting experience because we’re related and I therefore don’t have the, “Okay,
0:25:37 well, what’s happening with this person and is she thinking this and the other?”
0:25:40 There’s that inherent trust.
0:25:50 I think that the challenges, though, are that in some ways, it feels like work is getting
0:25:54 put before our life.
0:26:00 For example, Jordan calls me Edith and every now and then, outside of the workplace, she’ll
0:26:01 say, “Hey, Edith.”
0:26:02 I’m like, “Oh, no, no, no, no, no.
0:26:03 This is a mom moment.”
0:26:04 Oh, so you switch.
0:26:05 She switches.
0:26:10 And that’s important from our colleagues’ perspective.
0:26:16 So that’s been kind of interesting and then the only other thing that I would add is that
0:26:23 I have worked in large organizations and been responsible with incredible colleagues for
0:26:29 many, many people, big budgets, big opportunities, big challenges.
0:26:34 Although I always prided myself in not being the decision maker, I always wanted everyone
0:26:39 to own it and would step in when I needed to.
0:26:45 At the end of the day, people knew that I was the decision maker and I was accountable,
0:26:46 too.
0:26:51 But working with Jordan, when we first got started, I didn’t want that dynamic.
0:26:52 She’s the CEO.
0:26:56 Jordan is the CEO of Medley and I am the co-founder.
0:27:01 And so there were many circumstances in the first months where we would be in meetings
0:27:04 and I wouldn’t really say much.
0:27:07 And I remember that meeting, Jordan, when we walked out and you’re like, “Why didn’t
0:27:08 you say anything?”
0:27:09 I was like, “Well, you’re the CEO.”
0:27:11 I was like, “Yeah, but you know the topic.”
0:27:13 Can you just jump on in there?
0:27:19 And so it’s been really great because I didn’t want to be the over-the-top boss lady.
0:27:22 We’re peers in this context.
0:27:25 We’re running this business and building this business together with our colleagues
0:27:26 at Medley.
0:27:31 And so that’s been a bit of an adjustment to know that we are coming at things.
0:27:34 There are some different angles and there are going to be moments where I’m going to
0:27:36 take the lead and that is the right way.
0:27:39 It’s kind of like what it’s like in any organization actually.
0:27:44 But here, I was more sensitive to it than I had been if she were not my daughter.
0:27:47 I can imagine it’s way more sensitive.
0:27:49 I would imagine it’s more difficult.
0:27:51 What’s the experience been like for you, Jordan, as the daughter?
0:27:54 It’s been incredibly meaningful.
0:27:59 Even just from the standpoint of growing up, my mom worked a ton.
0:28:06 She had very high-powered jobs and 10 a.m. on Tuesday, I was at school.
0:28:10 She was at work and we would reconnect when she came home from the office.
0:28:15 Now we start most of our days talking to each other.
0:28:21 And it is a highlight when at 7.30 a.m., 7 a.m., 8 a.m., I get a call.
0:28:22 Are you awake?
0:28:23 How are you doing?
0:28:24 I still have bad habits.
0:28:31 I start super early and I still kid myself and say, “You don’t have to answer me right
0:28:36 away at 6.30 a.m.,” so I work it on that, but that’s a hard one to break.
0:28:41 But I will say sometimes it’s work and sometimes it’s not.
0:28:47 And I have learned so much from getting to work with her.
0:28:50 How to engage with people, how to listen to people.
0:28:53 A lot of the skills we’ve been talking about earlier.
0:28:58 My mind is often blown and sometimes I leave the meeting and I’m like, “How did you even
0:28:59 see that?
0:29:03 How did you know that this person was thinking X, Y, Z to tee this up?”
0:29:05 It’s absolutely incredible.
0:29:09 So from a professional standpoint, I’ve learned a lot.
0:29:14 And I will say also from a personal standpoint, I’ve learned a lot by getting to see my mother
0:29:21 in a working environment and see how she handles stress from work that I’m very, very close
0:29:27 to and juggles it from priorities and it’s constantly prioritizing.
0:29:34 And I think I will echo the challenge that she shared around creating space for work
0:29:37 and life.
0:29:41 That is always difficult.
0:29:49 We have built up enough trust now that if I say, “I need mom mode or I need work mode,”
0:29:50 we’re able to switch between them.
0:29:51 Is that what you say?
0:29:52 Mom mode, please?
0:29:53 Yeah.
0:29:58 Can we just put Medley on pause for a second and talk about X, Y, Z?
0:30:03 So all in all, it’s really enhanced our ability to communicate and we’ve gotten to know each
0:30:06 other in a very different way.
0:30:12 It’s a very unique experience and I’m excited for the future as we continue to grow the
0:30:17 business and both of our roles continue to evolve to continue to learn.
0:30:21 The co-founder relationship is a very stressful and fraught one.
0:30:29 I’m very close and then the mother and child relationship is very close, trusting, loving
0:30:32 and also pretty fraught and stressful.
0:30:38 Has there ever been a moment where the pressure of work has put a strain on your personal
0:30:41 relationship in a negative way at all?
0:30:42 No.
0:30:43 I’m getting a shaking of the head.
0:30:44 Do you agree, Jordan?
0:30:45 No, no, yeah.
0:30:46 I don’t think so.
0:30:47 It’s not great.
0:30:48 She’s like no.
0:30:49 She’s aggressively saying no.
0:30:50 No, it’s perfect.
0:30:51 Go, Jordan.
0:30:52 Exactly.
0:30:53 Sorry.
0:30:54 Go ahead, Edith.
0:30:55 Your own’s with no.
0:30:56 No.
0:31:00 I just, first of all, we want to let it go there.
0:31:02 And it’s not that we agree on everything.
0:31:13 I think we’re very conscious of being respectful of each other’s opinions, taking into consideration
0:31:20 the opinions of other people on the medley team, and I honestly cannot think of a single
0:31:27 time where it’s gotten so challenging that I would sit and talk to my other two children
0:31:32 or my husband about, you know, oh my gosh, you know, this is just out of control because
0:31:33 we talk about it.
0:31:40 See, that’s the thing about being a related mother, daughter team is that we really do
0:31:45 even when we’re not agreeing on something, believe that we have the same goal.
0:31:49 Yeah, I think that we work it through.
0:31:50 What do you think?
0:31:52 I would absolutely agree with that.
0:31:56 And it doesn’t mean, as Edith said, that we don’t disagree about things, that there
0:32:02 aren’t moments of challenge or tension in any healthy relationship, you’re encountering
0:32:03 all those things, right?
0:32:10 You’re encountering joy, you’re encountering affection, you’re encountering disagreement.
0:32:15 But we do really have each other’s best interests at heart, and I think that’s important for
0:32:19 any relationship period, but especially a co-founder relationship, if you have that
0:32:26 level of trust, and you know the other person is, you don’t have any worries about the other
0:32:33 person’s intentions, you’re able to communicate and navigate three different challenges, and
0:32:37 it’s really been a highlight of building the company, has been getting to work, to work
0:32:39 with Edith, work with my mom.
0:32:47 So it hasn’t all been sunshine and roses, but we know each other so much better.
0:32:52 We know like a third dimension of how we exist and how we operate, which is really fun.
0:32:59 It sounds like you both went into this kind of unusually skilled at the separation of
0:33:07 work and life and making strategic decisions and separating that from your emotions and
0:33:14 you describe, you call Edith in certain situations, mom in certain situations.
0:33:17 Did you know this going into, or has this been a training program?
0:33:18 How did you figure this all out?
0:33:19 There’s a playbook.
0:33:20 There’s no playbook.
0:33:25 There’s no playbook for someone like myself who worked in large institutions previously
0:33:33 for 35 years to roll up into an organization where it’s Jordan and myself sitting in a
0:33:38 two-seater because we didn’t want to spend the money on a three-seater in a shared workspace,
0:33:40 but you pay attention and you learn as you go.
0:33:46 We were looking for our first analyst as an example, and there were so many things going
0:33:47 on.
0:33:51 It was really super early days, and Jordan looked at me, she said, “This was calling
0:33:52 me mom.
0:33:53 There’s only the two of us.”
0:33:59 And she says, “Mom, you ran HR for 35,000 person organization.
0:34:02 You must know how to find candidates on LinkedIn.”
0:34:05 And I’m like, “Uh, that would be a no.”
0:34:10 I said, “I could call somebody who can help me figure out candidates on LinkedIn.
0:34:17 I’m willing to give it a go,” but there were those moments of, “Oh, oh, yeah.
0:34:24 You actually weren’t operating yourself personally every aspect of all of the roles for the last,
0:34:31 I don’t know, 15, 20 years,” but we moved forward and we sit together and we figure
0:34:37 out how to leverage the platform or any other platforms and et cetera, et cetera, but there’s
0:34:40 a lot of that because what do I know?
0:34:48 I know a lot about the things that I’ve experienced, as does Jordan, but I really respect that
0:34:56 there’s much in this construct of standing up medley from ground zero in a new category,
0:35:01 working together as a mother, daughter, co-founder team.
0:35:07 There’s as much that we have to learn and there is no playbook for that.
0:35:10 There’s no playbook.
0:35:17 That’s one of the things we have most in common is our voracious need to try to learn as much
0:35:19 as we can in every context.
0:35:26 We both fundamentally believe we can learn from any situation and from any person.
0:35:31 That shared value has enabled us to work through these types of things and build up that muscle
0:35:33 of communicating with each other.
0:35:38 For myself, I take my growth as a founder, as a CEO, really seriously.
0:35:45 I have had a coach, I’ve been in a group, a group of other founders, I have a therapist,
0:35:50 I take my exercise, sleep, all that stuff pretty seriously and so does Edith.
0:35:57 She does not miss a workout, let me tell you, every day, she doesn’t mess around.
0:36:02 I think that has been a huge enabler for us because it’s not as though we showed up on
0:36:06 day one and then just said, “Okay, let’s see what happens.”
0:36:11 It actually was a super intentional process for both of us to always be trying to learn,
0:36:15 to share feedback with each other, to invest in ourselves and invest in each other.
0:36:22 But this concept of there is no playbook is, I think, becoming the norm, not just for founders,
0:36:27 but for any organization that wants to be relevant today and into the future.
0:36:29 What is the playbook?
0:36:33 What is the playbook when a new drug changes the consumer appetite?
0:36:39 What is the playbook when technology that has been around for decades explodes into this
0:36:43 new incredible world of machine learning and AI?
0:36:49 What is the playbook for next year, let alone for the next 10 years?
0:36:57 And so I think that much of our experiences are similar to what we are talking with the
0:37:02 organizations that we’re working with about.
0:37:08 When you think about what it takes to really build sustainably important organizations,
0:37:13 you’ve got to really have a culture that enables people to connect how they operate,
0:37:17 how they interact, all those things that we were talking about with respect to listening,
0:37:21 communicating, et cetera, to the ultimate goal.
0:37:28 So if everybody walked out of the room and says, “I feel really heard and I feel included,”
0:37:32 but you have no idea what you’re supposed to be delivering and how you’re supposed
0:37:35 to deliver it, that’s not the point of all of this.
0:37:41 The point of all of this is to really appreciate the fact that in any kind of a business environment
0:37:48 where the playbook may be known today and not, you’ve got to have intellectual versatility
0:37:55 to operate and to engage in a very meaningful and steady, quick way.
0:38:01 And that’s what’s super exciting for me about sort of reinventing myself into a founder.
0:38:16 We’ll be right back.
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0:39:54 This is an unexpected question.
0:39:56 So good job.
0:40:06 I think it’s something that I knew, but I would say it’s been accelerated to the top
0:40:14 of my consciousness, and that is, you have to be present.
0:40:18 I think throughout the years, I have three children, Jordan’s the oldest, I have two
0:40:19 boys.
0:40:28 As Jordan described, a pretty intense professional existence, and as time went by and I got more
0:40:35 ownership of my schedule, et cetera, I would show up from Mars, it seems, sometimes.
0:40:43 My longest trip was from New Zealand to Providence, Rhode Island to see my Sunplay soccer.
0:40:53 But I would say that sometimes I was there, and I could have been more present.
0:40:56 But I was doing the best I could, and I was giving myself high marks.
0:40:57 I just shared this story.
0:40:58 It wasn’t that incredible.
0:41:00 I traveled all the way around the world.
0:41:06 But I do think that I’ve learned, particularly because we have to be very deliberate about
0:41:14 the separation of work and our lives, that when Jordan says, “Oh, can I just talk to
0:41:19 you about a few things that are not …” That is focused time.
0:41:21 That is really focused time.
0:41:32 And when I hear, “I’m not having a good morning,” I have to really respect that in a different
0:41:33 way.
0:41:35 I’m kind of a, “Let’s go.
0:41:37 Let’s push through.”
0:41:43 And I think that’s a good lesson for motherhood, that you want to have that relationship where
0:41:52 when someone, when your child says, “I’m struggling with something that you don’t try to fix it,
0:41:55 because I’m a fixer.”
0:42:02 And so that I’ve learned a lot with working with Jordan in Medley, that when she asks
0:42:11 me a question about life or work, she’s actually most of the time not asking me for the answer.
0:42:14 She’s asking for an opportunity to talk it through.
0:42:19 In fact, just the other day, you’re like, “Listen, listen, I just want to talk it through.
0:42:20 I’m not asking you to do it.
0:42:23 I just want to …” Because I’m like, “Okay, I got this.”
0:42:24 She’s like, “No, you don’t.
0:42:25 I need to talk.”
0:42:29 I’ve been studying this for a long time.
0:42:31 So that was a really interesting question.
0:42:37 And I’ll add, we’re expecting our first child in the fall, and we’re having a girl.
0:42:39 So this will be really funny.
0:42:42 I don’t think she can work in the business quite yet, but just give her a couple of years
0:42:44 and it’ll be a three-generation business.
0:42:51 And I will say the thing that I’m trying to embrace entering this huge life transition
0:42:55 is just the unpredictability of everything.
0:43:02 I mean, I have gotten so much more comfortable with both ambiguity, so looking into the
0:43:06 future and not knowing exactly what it’s going to look like.
0:43:12 And also just the lack of control that we really have over things.
0:43:15 You don’t think that you start a fundraised process and then Silicon Valley Bank is going
0:43:16 to collapse.
0:43:20 You don’t think you’re going to launch an in-person community and then COVID-19 happens.
0:43:24 You just don’t think that’s going to happen, but that’s life, right?
0:43:26 Life is pretty unpredictable.
0:43:32 And I’ve built up a lot of confidence, my ability to just navigate unexpected situations.
0:43:38 And I think that will help me in parenting because from what I can tell and seeing my
0:43:43 friends and even seeing, you know, in my family with my siblings and my cousins, you don’t
0:43:47 know what the child’s going to be like, you don’t know what life’s going to give you.
0:43:52 And part of that is part of the fun, I would say.
0:43:53 So I’m looking forward to that.
0:43:57 Do you have any like hold boundaries, like, you know, don’t text me at this time or anything
0:43:59 like that?
0:44:10 I try not to engage and in fact, I don’t actually engage with Jordan about work on Sunday afternoon
0:44:11 at four o’clock.
0:44:18 That was a really bad habit I had because the cadence of the week gets started, I get
0:44:22 myself organized and, you know, I’ve done that for 35 years.
0:44:24 So it was a hard thing to break.
0:44:29 And it was very disruptive actually to Jordan and her husband and, and quite frankly, everyone
0:44:30 around me.
0:44:34 So, you know, and for me, that’s a hard rule.
0:44:39 We were choking earlier about the 630 text.
0:44:40 I don’t really do that that often.
0:44:42 I get up sometimes at five o’clock in the morning.
0:44:47 I don’t do that because that’s a drag, you know, you get up whatever time you get up,
0:44:50 you see this text, you’re like, don’t even have your mind, right?
0:44:57 You got to like, you know, so that’s a pretty hard rule to look if I’ve got something that
0:45:00 really needs to have a conversation.
0:45:05 I don’t put it in a text at seven in the morning, you know, say, Hey, give me a call when you
0:45:06 can.
0:45:11 And the other thing I think is very important in this conversation about first time founders
0:45:16 is that people are watching you, whether you have three people, 10 people, 20 people,
0:45:22 whatever the number is, people do care about the balance that they have in their lives
0:45:27 more every, every year.
0:45:30 And I think that’s really important and it matters.
0:45:37 And so therefore, you know, I, I can get pretty intense, Jordan can get pretty intense and
0:45:43 quite frankly, most of the people on our team can, but I really have watched very closely
0:45:50 how Jordan has been very clear and respectful of people and their lives.
0:45:55 And so that when someone is on holiday and hasn’t been on holiday and is really delivered,
0:46:02 she will literally say, okay, anything that’s going, you know, to this person, you know,
0:46:06 is going to go into an inbox, I’ll be watching the inbox just so you know.
0:46:08 And that’s different from the Goldman style.
0:46:14 Oh, perhaps. Yes. But you know, the interesting question is, what is it like?
0:46:18 I haven’t been in Goldman for, you know, six years now almost.
0:46:20 What is it like now, perhaps?
0:46:26 And there were moments then where, you know, there was no working for investment banking
0:46:31 on Saturdays and whatever the case may be, but all of this is in response to the reality
0:46:38 of who’s showing up and people show up wanting to be human beings with work being part of
0:46:40 their existence, not their only existence.
0:46:46 I’m going to shift to a quick lightning round here about organizational management, which
0:46:47 I feel like you both are experts here.
0:46:52 I’m just going to throw you some questions and we’ll get your hot takes on some of these.
0:46:54 So we’ll start with Edith.
0:46:57 How can companies make meetings more productive?
0:47:00 Make sure there’s a clear agenda.
0:47:04 Hope people accountable for doing the work before they come to the meeting.
0:47:11 And as participants in the meeting, keep it concise, not my specialty.
0:47:18 So I’ll work on that and pay attention to who talks and who doesn’t talk.
0:47:20 Clear follow-ups to conclude.
0:47:24 Jordan, is remote work overrated or underrated?
0:47:26 Personally overrated.
0:47:32 But flexibility, I will say, is really what’s valued from what we’re seeing in terms of
0:47:33 remote work.
0:47:34 That’s a really concise answer.
0:47:35 That’s good.
0:47:37 Let me see what I can do.
0:47:38 Let’s go.
0:47:39 She’s learning from the master, right?
0:47:45 Edith, what is the best way to measure employee success at a company?
0:47:51 The productivity of the company, not just in terms of the bottom line, but in terms of
0:47:58 what the reputation of the company is and how they deliver that profitability.
0:48:00 That’s employee success, right?
0:48:03 That doesn’t happen without employees being successful.
0:48:08 Jordan, when it comes to decision-making, do you prefer using your instincts or data?
0:48:09 Data.
0:48:15 But Edith prefers instincts, so we are a great match in that regard.
0:48:16 Okay.
0:48:17 Why are you pro-data?
0:48:19 Why is Edith pro-instincts?
0:48:28 I think for me, data is more my natural approach, although at this point, I’ve really been working
0:48:29 on this.
0:48:34 I do try to make decisions based off of instinct more.
0:48:40 The way I describe instinct is that it’s actually a cumulation of your experiences.
0:48:46 Instincts are informed by data, but I think to start, my natural inclination is, well,
0:48:50 I want to understand and get all the information, but when you’re running a startup and over
0:48:54 the past five years I’ve learned, you really can get all the information, so you have to
0:48:55 use both.
0:49:00 Edith, how important is DEI, and do you think it’s something that every company should
0:49:02 be implementing?
0:49:10 Every company that wants to be a relevant company needs to invest in their people and
0:49:16 create environments where everyone can thrive, and that’s everyone.
0:49:22 That’s people who are part of the majority, people who are from different schools, from
0:49:25 different languages, cultures, etc.
0:49:29 Many people have asked me, particularly in the last year, what’s going to happen with
0:49:30 DEI?
0:49:31 Is it going to be over forever?
0:49:32 I don’t know.
0:49:33 Do you want to be an excellent company?
0:49:37 If you want to be an excellent company, you continue to do the work.
0:49:39 You can call it what you want.
0:49:40 You have to do the work.
0:49:46 Do you think it’s been politicized in a way that’s been destructive to organizations?
0:49:56 I think that it has certainly been politicized, and I don’t think it has been particularly
0:49:59 productive.
0:50:07 I don’t think it’s been as disruptive as people might think, because strong organizations
0:50:13 with strong cultures understand how important it is to extract excellence.
0:50:15 People ask me, “What should we call it?”
0:50:21 I said, “Why don’t you just call it excellence,” because that’s what it means to have a truly
0:50:26 diverse organization from a number of different perspectives.
0:50:33 All the organizations that I’ve worked with and continue to talk to, they’re moving forward
0:50:36 because they want to be great.
0:50:42 To be great, you have to have the diversity of experience, perspectives, culture, sexual
0:50:43 orientation.
0:50:47 The list will just continue to get longer and longer.
0:50:49 What an exciting opportunity.
0:50:55 Jordan, this one came to me because we were discussing the idea of bringing a full self
0:50:58 to work.
0:51:04 Is there space for political opinions in the workplace, and should leaders be taking
0:51:07 up political opinions if they choose?
0:51:11 It really depends on the company and their culture and their values.
0:51:16 For some companies who have made statements that they do not want to engage in the political
0:51:21 dynamic, those companies are going to attract people who want to work in those environments.
0:51:25 On the flip side, companies where leaders really are taking a stand or voicing their
0:51:31 opinion in whichever direction, the same thing is happening.
0:51:34 People are going to be drawn to working at those companies because that’s a value that
0:51:37 they care about.
0:51:43 Finally, I think that there needs to be a way for leaders to acknowledge what’s happening
0:51:48 in the world and give space for employees who are probably processing in some way or
0:51:49 the other.
0:51:54 That’s what we try to do internally at Medley is really just giving space for people.
0:52:00 I do think that we’re just going to see some real self-selection in terms of employees,
0:52:03 and they’ll vote by going where they want to work.
0:52:08 Real questions from me, and thank you both for being generous with your time.
0:52:11 Edith, actually, we’ll start with Jordan.
0:52:13 Some advice to our listeners.
0:52:18 We have a lot of female listeners on the show.
0:52:21 Scott seems to think we don’t, but we do.
0:52:25 Do you have any advice on how to be a good daughter?
0:52:31 I will say as you grow up and as you encounter different experiences, embrace the fact that
0:52:34 your relationship with your mom might change.
0:52:35 That can be exciting.
0:52:36 It can be a good opportunity.
0:52:37 Are you a dad?
0:52:38 Yes.
0:52:39 You’re right.
0:52:43 Or you’re a dad with your parents.
0:52:49 Embrace this fact that your relationship with your parents likely will change over time.
0:52:53 I think accepting that can really enable new types of relationships to build with your
0:52:54 parents.
0:52:56 Edith, any advice on how to be a good mother?
0:53:06 Not to get a little syrupy here, but love unconditionally because it’s a ride.
0:53:14 If you make that the core of your relationship, it becomes multi-dimensional.
0:53:23 It becomes positive reinforcement, feedback, direction, and just some good hugs from time
0:53:24 to time.
0:53:26 It’ll all be okay.
0:53:33 But if you start with that center and you develop trust of caring, anything that comes
0:53:39 your way, you’ll be able to navigate and things will come your way.
0:53:40 I love that.
0:53:44 Jordan Taylor and Edith Cooper are the co-founders of Medley, a group coaching platform.
0:53:45 Thank you very much both for joining me.
0:53:48 Thanks for having us.
0:53:55 Our producer is Claire Miller, our associate producer is Alison Weiss, and our engineer
0:53:56 is Benjamin Spencer.
0:53:59 Catherine Dillon is our executive producer.
0:54:02 Thank you for listening to First Time Founders from the Vox Media Podcast Network.
0:54:05 Tune in tomorrow for Prodigy Markets.
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0:00:37 Hey, I’m Jon Collin Hill, host of a brand new show from Vox called Explain It To Me.
0:00:40 This week, the ethical murkiness of zoos.
0:00:46 Do we as humans feel like we deserve to just be able to walk around and see these animals?
0:00:48 Maybe we don’t deserve that.
0:00:51 Maybe there’s just some animals we don’t get to see.
0:00:53 To zoo or not to zoo?
0:00:55 That’s this week on Explain It To Me.
0:01:02 Listen wherever you get your podcasts.
0:01:07 Scott, what would be your advice to someone who wanted to start a company with a family member?
0:01:12 First, first word that came into my mind was don’t.
0:01:17 Look, I just think it’s situational.
0:01:21 It’s it’s so much of resting on the family dynamic.
0:01:28 I mean, I always thought I would never want to leave my kids a lot of money and I wouldn’t
0:01:31 want to work with my kids because I enjoy my relationship so much with them that I’d
0:01:36 hate if we didn’t get along professionally that it could put strain on the relationship
0:01:37 itself.
0:01:40 But at the same time, I also love the idea of building something that I could give to my
0:01:46 kids that they could that they could enjoy and build and family businesses.
0:01:50 A lot of people, you know, there’s a lot of family businesses and for a lot of people,
0:01:52 I think they’re very rewarding.
0:01:53 I just think it’s situational.
0:01:58 If two brothers get together and they have an idea for something, I get it.
0:02:03 I would think, and maybe this is because I’m not very close with my family, I was close
0:02:08 with my mother, but I hate having that many eggs in one basket.
0:02:13 It’s just the idea of adding another potential point of dysfunction where you start a business
0:02:15 together and it doesn’t work.
0:02:16 I just think it’d be devastating.
0:02:22 Like, if I started a business with my son and it didn’t work, right, and it put tension
0:02:26 on the relationship, that would be heartbreaking for me.
0:02:31 So what I would suggest is that if you are thinking about a business with a family member
0:02:36 that you immediately have an informal board of directors and that is someone outside of
0:02:42 the family that you both trust that can serve as a fiduciary for kind of coaching you around
0:02:48 issues, because it’s one thing if your business goes bad, but to strain a relationship in
0:02:51 a family, I think it would just be devastating.
0:02:56 I knew one of the nephews and nieces, one of the privileged jerks of the Bronfman family,
0:03:01 and I remember I had to share with them in the Hamptons, and this person was shitposting
0:03:03 Edgar because he’d lost so much money.
0:03:06 I’m confused why a Bronfman was in a sharehouse.
0:03:07 Yeah.
0:03:08 Sorry, go ahead.
0:03:09 He was in a sharehouse.
0:03:10 Yeah.
0:03:11 Yeah.
0:03:12 He had hot friends.
0:03:17 Anyways, but I remember her just talking so much shit about Edgar because he bought
0:03:21 some company and turned $8 billion of their fortune into a billion.
0:03:22 I don’t know.
0:03:26 It just feels, and then, you know, my entire insight into a family business is succession
0:03:31 and they all look fucked up and like they hate each other, so my general instinct is
0:03:38 I don’t want to say never, but I think you’re better off doing it with friends because I’m
0:03:41 still close with my initial business partner.
0:03:42 No, it’s not true.
0:03:44 We’re still friends, but we’re not close.
0:03:47 We just had a different approach to business over time, and while we’re still friends,
0:03:49 I invest in his companies.
0:03:53 I know I could count on him for anything, and he knows he could count on me.
0:03:57 But if we were like brothers, and there was sort of that what I’ll call easing back from
0:04:03 the relationship, I think it would put a strain on our brotherhood, and I just, I think family’s
0:04:04 so precious.
0:04:13 My initial inclination is tread carefully around that.
0:04:15 Welcome to First Time Founders.
0:04:20 Since COVID-19, the dynamics of the workplace have significantly shifted.
0:04:24 Nearly half of Americans today feel unsatisfied with their jobs, and more than half feel they
0:04:27 are lacking in professional growth.
0:04:29 Companies meanwhile have done little to address this.
0:04:35 83% of companies say developing leaders is important, but only 5% have actually developed
0:04:37 leadership programs.
0:04:41 My next guest, while at business school, came up with an idea to address the problem, an
0:04:45 online platform for group-based leadership development and coaching.
0:04:49 And to get this idea off the ground, she tapped a veteran, her co-founder as a former partner
0:04:54 at Goldman Sachs, a current board member of Amazon and PepsiCo, and also happens to be
0:04:56 her mother.
0:05:01 After launching in 2020, the mother daughter duo went on to raise $4 million in funding
0:05:05 from investors, including Andreessen Horowitz, and now works with over a dozen Fortune 500
0:05:08 companies to support their emerging leaders.
0:05:15 This is my conversation with Jordan Taylor and Edith Cooper, the co-founders of Medley.
0:05:17 Jordan and Edith, thank you for joining.
0:05:19 Thanks for having us.
0:05:24 So you are definitely the first mother daughter duo that we’ve had on the program.
0:05:29 We’ll get into that relationship in a bit, but let’s just start with the company.
0:05:33 Jordan, what is Medley and what inspired you to start this company?
0:05:36 Medley is an enterprise group coaching platform.
0:05:37 So what does that mean?
0:05:43 We work with large companies to design, launch, and scale group-based coaching programs, solving
0:05:47 for connectivity in addition to leadership development.
0:05:52 And our participants are usually people in their 20s, 30s who are really looking to figure
0:05:57 out their careers and how they want to lead and influence others.
0:06:02 The idea for Medley was actually inspired by a course that I took in my last semester
0:06:03 at Harvard Business School.
0:06:09 It was called Authentic Leadership Development, and the class took place in small groups.
0:06:14 So you’re sitting with six people in a room for two hours every single week.
0:06:16 It was completely transformative.
0:06:21 I learned so much about myself, about other people, how to engage with them.
0:06:24 My perspective was expanding.
0:06:29 And after I did some digging, I realized that these small groups were actually everywhere.
0:06:34 They were in a lot of different spaces, whether it was AA or Weight Watchers or religious
0:06:40 constructs, even with executives, organizations like YPO existed and had a huge success.
0:06:45 And so as I was thinking, okay, how could we build something where more people can access
0:06:53 this meaningful growth experience? I had been keeping my mother in the loop and from the
0:06:58 lens of thinking about exploring this idea, I think there’s something in groups.
0:07:00 Not sure what the business is.
0:07:08 She had retired from Goldman Sachs about six months prior to one of these pivotal conversations.
0:07:13 And she thought she was going to retire, join a couple of boards, spend a lot of time outside
0:07:16 and with friends.
0:07:20 And she actually called me after one of those updates and said, “Jordan, I think we should
0:07:22 be building Medley together.”
0:07:23 Oh, wow.
0:07:24 Yeah.
0:07:25 Okay.
0:07:29 So I think, did she know what it would be like to build a startup from scratch?
0:07:30 No.
0:07:34 To be fair, neither did I.
0:07:38 But I think that’s just been a highlight of the experience that I’m sure we’ll delve
0:07:39 more into.
0:07:40 Yeah.
0:07:44 We’ve been really working on the business together for the past five years.
0:07:48 My next question for you, Edith, was going to be how did Jordan convince you, but it
0:07:50 sounds like you didn’t need much convincing.
0:07:56 No, I really didn’t because what she was focused on was something that had always mattered
0:08:01 deeply to me as a business person, as a leader, and quite frankly, as a human.
0:08:09 I had the good fortune and shall we say, persistence to have worked in financial services for more
0:08:11 than three decades.
0:08:16 And my last job at Goldman Sachs was running human capital management, otherwise known
0:08:17 as HR.
0:08:20 That was an interesting time at Goldman.
0:08:26 And it became very clear to me then, probably because it was my full-time gig, but it always
0:08:34 been clear that my job, our job as colleagues, as leaders, as people were to create an environment
0:08:38 where people can really thrive, not just a certain type of person who can morph themselves
0:08:43 into the mold of what had been successful before, but for a broad group of people who
0:08:46 brought many talents to the organization.
0:08:51 And so as Jordan and I were talking about the significance of learning how to show up
0:08:57 for yourself in the context of others, that’s how I think about groups and groups performance.
0:09:01 It seemed like it was something that was so important and I wanted to join.
0:09:07 And I also wanted an opportunity to work closely with Jordan.
0:09:15 I’d been her mom since day one, but I saw the evolution of her approach to business
0:09:19 and to commerce, and I thought I could learn a lot.
0:09:21 And I certainly have.
0:09:24 How do these group lessons work?
0:09:25 Is there a leader?
0:09:28 Do people, is it sort of like a seminar?
0:09:29 How does it work?
0:09:33 So your methodology works, it is pretty far from a seminar.
0:09:36 So we have coaches who lead every group session.
0:09:40 So from a participant standpoint, the first thing you do is you fill out our matching
0:09:44 questionnaire and we match you to a group of other leaders who are experiencing similar
0:09:49 challenges and are in a similar place in their careers and leadership journeys.
0:09:54 The groups meet over the course of eight sessions, over the course of four to eight months.
0:10:01 So they’re working with the same coach throughout, but it is very different and far from a typical
0:10:02 training.
0:10:06 You know, when you think about the training that you might have at your company, you might
0:10:10 think of sitting in a big room, watching a big screen or watching a Zoom lesson.
0:10:11 Yeah, a presentation.
0:10:12 Yeah.
0:10:14 No, this is incredibly interactive.
0:10:19 Our coaches are really going deep with people and our style really does incorporate the
0:10:23 personal and the professional because it’s so clear now that there’s just a blending
0:10:28 that is a result of the world that we live in.
0:10:34 Edith, do you think that what you’re providing now is missing based on your experience, you
0:10:39 know, you’ve worked at Goldman Sachs, you’ve also been on the boards of Etsy and Slack,
0:10:44 you now sit on the boards of Amazon and PepsiCo, do you feel like what you’re providing with
0:10:49 Medley is missing from large enterprises such as the ones you’ve worked at?
0:10:53 I think that if you were to talk to most organizations, certainly the ones I’ve been
0:10:58 involved in, and you asked what really makes a difference to the culture, at some point
0:11:02 they would say cultural values and they could name them and they would say managers are
0:11:05 important, leadership is important.
0:11:10 But I would say historically, when you said, okay, what does that mean?
0:11:14 You’d get a lot of different types of answers.
0:11:16 Some people would say, oh, there’s a lot of soft skills.
0:11:22 You have to, you know, be approachable, accessible, et cetera, but what I’m seeing now, what we’re
0:11:29 seeing is that what we used to think about as soft skills, listening, reacting, interpreting,
0:11:32 understanding, are not actually soft at all.
0:11:36 They are actually quite challenging.
0:11:37 They’re hard.
0:11:42 And so what Medley does is it creates opportunities for people to show up in these small groups
0:11:47 of six to eight people with a professional coach to really put to practice how they show
0:11:53 up as individual for the benefit of themselves, but also the benefit of the group.
0:11:54 What is a group?
0:11:55 A group is a team.
0:11:57 What is an organization?
0:11:59 A bunch of different teams.
0:12:05 And so it’s been very, very exciting and rewarding to see the impact that we’ve made on the
0:12:07 employees experience.
0:12:12 We’ve worked very hard to make sure that Medley is integrated into the overall talent framework
0:12:15 and we’re excited about the forward.
0:12:17 And by the way, I totally agree with that.
0:12:22 My experience, my professional experience so far is that most of work is soft skills.
0:12:26 Granted, I’m in a kind of niche industry, but it’s all you’re just working with people.
0:12:28 So you’ve got to get along with people.
0:12:31 And if you do that, my view is that you will succeed.
0:12:37 But I’m wondering, you know, having been basically global head of HR at Goldman, do you think
0:12:43 that soft skills have historically been undervalued or underrated or soft skills kind of making
0:12:45 a comeback at this point?
0:12:49 People are showing up at work today as humans.
0:12:54 They are not as excited about leaving who they are behind.
0:13:01 They want to be able to see leadership and be themselves authentic.
0:13:08 And they want to be able to talk about not just what’s going on in the day-to-day workplace,
0:13:11 but what’s going on everywhere else.
0:13:17 And that’s hard if you don’t actually take the time to be intentional to learn how to
0:13:24 listen to people, to figure out who is talking and who’s not talking, to think about how
0:13:28 to respond when you disagree with someone.
0:13:32 And an environment like this where the pace of change is extraordinary, there’s a lot
0:13:37 going on in the world that presents interesting opportunities, but there are a lot of challenges.
0:13:39 You’ve got to be able to do that.
0:13:40 Those are not soft skills.
0:13:47 Historically, if you are a deep subject matter expert, and it is probably still true in certain
0:13:48 organizations, you can get a long way.
0:13:54 You really can, deep, deep, deep understanding of your craft, whatever organization you work
0:13:55 in.
0:14:00 But what happens is over time, as you get better and better and better, what do you get?
0:14:06 More responsibility, and it’s more responsibility for other human beings.
0:14:12 And so medley is an opportunity to give people the space to learn what that should feel like
0:14:14 and how you should action it.
0:14:16 And it’s a completely different job, right?
0:14:22 When you’re a manager of a team, that’s not the same as just being really good at being
0:14:23 a great programmer.
0:14:28 But it’s strange that we have this system where if you get better at your vertical in
0:14:31 a way, then you get more responsibility of the people, but I guess you don’t get taught
0:14:34 how to manage people.
0:14:37 I mean, if you could solve this problem, I would love this.
0:14:44 I would love it if I could myself be an incredibly good listener, work well with people, and
0:14:46 I could make everyone at my company be the same way.
0:14:49 That would be a dream.
0:14:52 But it seems very difficult to do.
0:15:00 And I could imagine walking into one of these group coaching sessions, and you know, someone
0:15:05 tells me you got to get better at listening, and I’m like, okay, sure, how do you actually
0:15:06 implement this?
0:15:12 How do you actually coach this stuff, which to me feels like more of an inherent trait
0:15:13 in people?
0:15:18 You know, I think certainly if the session was designed and you showed up and it said,
0:15:23 all right, your growth area is listening, just listen better, would not be incredibly
0:15:25 effective.
0:15:31 That said, if you shift the frame and really do accept that listening can be a skill you
0:15:35 can practice, a group is an incredibly powerful space to practice that.
0:15:40 Because imagine if you’re working with a coach one-on-one, the coach can relay back,
0:15:44 you know, I’ve heard in your feedback that sometimes you come across like you’re not
0:15:45 paying attention.
0:15:46 Great.
0:15:52 If you’re in a group of eight other people, and the coach is actually saying, Edith, how
0:15:56 do you respond to what Ed just shared, it’s putting you on the spot.
0:16:01 It’s creating that space for you in a pretty low-risk environment to actively listen and
0:16:02 to practice.
0:16:07 And so, you know, in a group session, there is active role-playing where we will do and
0:16:14 practice listening or communicating, navigating conflict, those types of skills that are incredibly,
0:16:16 incredibly difficult.
0:16:21 I will also add that where we are from a technology standpoint presents a pretty exciting opportunity
0:16:26 to make these skills much more tangible for people and actually build upon them in a way
0:16:28 that people can measure and understand.
0:16:32 And that’s something that we’re spending a lot of time on now, is how do we take these
0:16:39 skills like listening, giving feedback, influential communication, inclusive leadership, how do
0:16:45 we take these skills and really make them measurable and understandable for both individuals
0:16:47 and for companies?
0:17:10 I’ll be right back.
0:17:14 When Kamala Harris and Donald Trump met on the debate stage, it was obvious that these
0:17:16 were two very different people.
0:17:19 But JD Vance and Tim Walls actually have a lot in common.
0:17:21 They’re both white men from the Midwest.
0:17:24 They’re both family men, and they were both in the service.
0:17:27 But they disagree on what it means to be a man.
0:17:28 Here’s my light pack.
0:17:32 Surround yourself with smart women and listen to them, and you’ll do just fine.
0:17:35 Today Explained, every weekday, wherever you get your podcasts.
0:17:50 We’re back with First Time Founders.
0:17:55 When I look at your resume, so you worked in consulting, you worked at Boston Consulting
0:17:56 Group.
0:17:58 You were a chief of staff and a successful startup.
0:18:00 You went to Harvard Business School.
0:18:03 You have kind of the perfect founder resume.
0:18:05 Did you always know you wanted to start a company?
0:18:06 I did not.
0:18:13 I think my experience at Mike, which is the startup that I worked at prior to business
0:18:18 school, really started to spark that interest.
0:18:24 I was excited by the amount of ownership that you can have in building a business.
0:18:28 I was excited by the genuine and authentic sense of teaming that you have with people
0:18:32 who are all in it, trying to do something crazy with each other.
0:18:39 After I’d graduated, I did have a strong instinct of wanting to build a company, but I do want
0:18:41 to go back to something you said.
0:18:47 On paper, I think I do have a resume that can scream entrepreneur, but Edith and I are
0:18:50 a very atypical founding team.
0:18:56 Firstly, we’re mother-daughter, secondly, we’re both black women, third, we don’t come
0:18:58 from a technical background.
0:19:04 Although, for the business that we’re in, I will say our technical skills are quite
0:19:07 relevant, just different.
0:19:12 It’s been interesting for us as we’ve built the business, grown the business, built a
0:19:17 team, engaged with investors, engaged with enterprise-level customers, figuring out our
0:19:23 own style, and actually figuring out how we can use our difference to our advantage.
0:19:30 You launched in 2020, as I mentioned, you raised this $4 million round, you’re partnering
0:19:32 with Fortune 500 companies.
0:19:36 Take us through just the trajectory of the company so far.
0:19:39 What have been some of the highlights, maybe some of the challenges?
0:19:42 How has the company changed over the last four years?
0:19:44 We’ve had two big pivots.
0:19:51 The first pivot was our original plan was to launch in April of 2020 as an in-person
0:19:55 membership community for people looking to invest in their personal and professional
0:19:56 growth.
0:20:01 If you can imagine a worse business to launch in April of 2020, where you bring people together
0:20:08 in small groups, in small groups, closed environment, in a physical space, Medley’s
0:20:11 pretty much it, the first iteration.
0:20:17 We remember vividly in March, we had the coaches lined up, we were putting finishing touches
0:20:23 on the office space for the space that we just signed, and we had to completely pivot
0:20:25 to an online model.
0:20:31 We had no idea if we could replicate that sense of connection, that impact, the dynamics
0:20:33 with the coaches.
0:20:34 We had no idea.
0:20:41 And so we ended up regrouping, doing some online testing, and launching Medley as a primarily
0:20:45 online community in August of 2020.
0:20:51 We then spent a couple of years building with individuals who recognized the need and who
0:20:55 were excited to invest in their own leadership development.
0:20:59 We had members from, I believe, 20 different countries around the world.
0:21:02 We got a great amount of traction.
0:21:08 And then towards the end of ’22, we actually were getting market pull from organizations.
0:21:11 So people were going back to their companies saying, “I participated in this thing called
0:21:12 Medley.”
0:21:15 I think other people here could benefit from it.
0:21:20 And then we’d get emails from people in the talent side of organizations saying, “Hey,
0:21:22 we’d like to learn more.”
0:21:28 And so it became really obvious at the beginning of last year that this was the huge opportunity
0:21:29 for Medley.
0:21:36 It was in helping large organizations connect and grow their emerging leaders, and help
0:21:41 solve for a few combining challenges that they’re experiencing right now.
0:21:49 It’s been very exciting, although a challenging time to build a company, most definitely,
0:21:51 but we definitely have enjoyed it.
0:21:54 So why don’t I add a couple of challenges?
0:22:01 Pivoting is exciting, but it’s also hard because you’ve invested in building the apparatus
0:22:04 to support an in-person model.
0:22:10 You incur the expenses associated with that, and then you don’t need it anymore.
0:22:19 This challenge, the fundraising environment can be challenging.
0:22:27 We were well-positioned in our seed round with a terrific group of investors.
0:22:40 We were marching towards the next raise in, was it the spring of last year, SVB, problematic.
0:22:46 Just say some of the people that we were in serious conversations with were very distracted.
0:22:48 That’s challenging.
0:22:57 Fitting your business into the expectations of a certain type of funding can work, but
0:23:02 it could also be challenging when the expectations shift.
0:23:10 So when you move from growth at any cost with profitability not being important to an environment
0:23:19 where people are focused on profitable growth and positive cash flow, could be a challenge
0:23:20 for us.
0:23:27 It’s been a real opportunity because our business has really grown as we’ve bought on more companies.
0:23:32 So therefore, that has swung back the other way, but I think the lesson that we’ve learned
0:23:39 throughout all of this is that you have to be very focused on your customer.
0:23:46 Make sure that you understand the value proposition that you’re offering, and then be prepared
0:23:52 to take in all that you learn from testing to adapt along the way.
0:23:57 You often say we’re flying the plane and we’re changing the windows at the same time.
0:24:05 Maybe that’s not a very nice analogy, but nevertheless, you’ve got to be able to adapt.
0:24:10 I have to say, that’s one of the things that I’ve had to really get used to because when
0:24:15 you work in a large enterprise in financial services historically, you have quarter to
0:24:18 quarter earnings.
0:24:23 These are tremendous amount of focus on risk and risk management, and just give it a go
0:24:25 and hopefully it works out.
0:24:31 But when you’re building something in a new category, you have to be willing to try things
0:24:34 and some of those things will not work.
0:24:35 Very different.
0:24:38 Yeah, I’m sure a huge mindset shift for you.
0:24:43 I do want to shift to the mother-daughter dynamic.
0:24:45 We’ll start with you, Edith.
0:24:50 What is it like starting a company and running a company with your daughter?
0:24:53 What have been some of your main takeaways?
0:24:58 I think that in the first instance, I got what I signed up for.
0:25:07 I have always, always believed that the future is in the hands and in the minds of those
0:25:13 that are coming up through schools, arriving in the workplace, et cetera, and I’ve gotten
0:25:14 all of that.
0:25:19 We had a different way of thinking through opportunities.
0:25:26 Our team is in the same genre and it’s just been an incredible experience.
0:25:34 It’s a very trusting experience because we’re related and I therefore don’t have the, “Okay,
0:25:37 well, what’s happening with this person and is she thinking this and the other?”
0:25:40 There’s that inherent trust.
0:25:50 I think that the challenges, though, are that in some ways, it feels like work is getting
0:25:54 put before our life.
0:26:00 For example, Jordan calls me Edith and every now and then, outside of the workplace, she’ll
0:26:01 say, “Hey, Edith.”
0:26:02 I’m like, “Oh, no, no, no, no, no.
0:26:03 This is a mom moment.”
0:26:04 Oh, so you switch.
0:26:05 She switches.
0:26:10 And that’s important from our colleagues’ perspective.
0:26:16 So that’s been kind of interesting and then the only other thing that I would add is that
0:26:23 I have worked in large organizations and been responsible with incredible colleagues for
0:26:29 many, many people, big budgets, big opportunities, big challenges.
0:26:34 Although I always prided myself in not being the decision maker, I always wanted everyone
0:26:39 to own it and would step in when I needed to.
0:26:45 At the end of the day, people knew that I was the decision maker and I was accountable,
0:26:46 too.
0:26:51 But working with Jordan, when we first got started, I didn’t want that dynamic.
0:26:52 She’s the CEO.
0:26:56 Jordan is the CEO of Medley and I am the co-founder.
0:27:01 And so there were many circumstances in the first months where we would be in meetings
0:27:04 and I wouldn’t really say much.
0:27:07 And I remember that meeting, Jordan, when we walked out and you’re like, “Why didn’t
0:27:08 you say anything?”
0:27:09 I was like, “Well, you’re the CEO.”
0:27:11 I was like, “Yeah, but you know the topic.”
0:27:13 Can you just jump on in there?
0:27:19 And so it’s been really great because I didn’t want to be the over-the-top boss lady.
0:27:22 We’re peers in this context.
0:27:25 We’re running this business and building this business together with our colleagues
0:27:26 at Medley.
0:27:31 And so that’s been a bit of an adjustment to know that we are coming at things.
0:27:34 There are some different angles and there are going to be moments where I’m going to
0:27:36 take the lead and that is the right way.
0:27:39 It’s kind of like what it’s like in any organization actually.
0:27:44 But here, I was more sensitive to it than I had been if she were not my daughter.
0:27:47 I can imagine it’s way more sensitive.
0:27:49 I would imagine it’s more difficult.
0:27:51 What’s the experience been like for you, Jordan, as the daughter?
0:27:54 It’s been incredibly meaningful.
0:27:59 Even just from the standpoint of growing up, my mom worked a ton.
0:28:06 She had very high-powered jobs and 10 a.m. on Tuesday, I was at school.
0:28:10 She was at work and we would reconnect when she came home from the office.
0:28:15 Now we start most of our days talking to each other.
0:28:21 And it is a highlight when at 7.30 a.m., 7 a.m., 8 a.m., I get a call.
0:28:22 Are you awake?
0:28:23 How are you doing?
0:28:24 I still have bad habits.
0:28:31 I start super early and I still kid myself and say, “You don’t have to answer me right
0:28:36 away at 6.30 a.m.,” so I work it on that, but that’s a hard one to break.
0:28:41 But I will say sometimes it’s work and sometimes it’s not.
0:28:47 And I have learned so much from getting to work with her.
0:28:50 How to engage with people, how to listen to people.
0:28:53 A lot of the skills we’ve been talking about earlier.
0:28:58 My mind is often blown and sometimes I leave the meeting and I’m like, “How did you even
0:28:59 see that?
0:29:03 How did you know that this person was thinking X, Y, Z to tee this up?”
0:29:05 It’s absolutely incredible.
0:29:09 So from a professional standpoint, I’ve learned a lot.
0:29:14 And I will say also from a personal standpoint, I’ve learned a lot by getting to see my mother
0:29:21 in a working environment and see how she handles stress from work that I’m very, very close
0:29:27 to and juggles it from priorities and it’s constantly prioritizing.
0:29:34 And I think I will echo the challenge that she shared around creating space for work
0:29:37 and life.
0:29:41 That is always difficult.
0:29:49 We have built up enough trust now that if I say, “I need mom mode or I need work mode,”
0:29:50 we’re able to switch between them.
0:29:51 Is that what you say?
0:29:52 Mom mode, please?
0:29:53 Yeah.
0:29:58 Can we just put Medley on pause for a second and talk about X, Y, Z?
0:30:03 So all in all, it’s really enhanced our ability to communicate and we’ve gotten to know each
0:30:06 other in a very different way.
0:30:12 It’s a very unique experience and I’m excited for the future as we continue to grow the
0:30:17 business and both of our roles continue to evolve to continue to learn.
0:30:21 The co-founder relationship is a very stressful and fraught one.
0:30:29 I’m very close and then the mother and child relationship is very close, trusting, loving
0:30:32 and also pretty fraught and stressful.
0:30:38 Has there ever been a moment where the pressure of work has put a strain on your personal
0:30:41 relationship in a negative way at all?
0:30:42 No.
0:30:43 I’m getting a shaking of the head.
0:30:44 Do you agree, Jordan?
0:30:45 No, no, yeah.
0:30:46 I don’t think so.
0:30:47 It’s not great.
0:30:48 She’s like no.
0:30:49 She’s aggressively saying no.
0:30:50 No, it’s perfect.
0:30:51 Go, Jordan.
0:30:52 Exactly.
0:30:53 Sorry.
0:30:54 Go ahead, Edith.
0:30:55 Your own’s with no.
0:30:56 No.
0:31:00 I just, first of all, we want to let it go there.
0:31:02 And it’s not that we agree on everything.
0:31:13 I think we’re very conscious of being respectful of each other’s opinions, taking into consideration
0:31:20 the opinions of other people on the medley team, and I honestly cannot think of a single
0:31:27 time where it’s gotten so challenging that I would sit and talk to my other two children
0:31:32 or my husband about, you know, oh my gosh, you know, this is just out of control because
0:31:33 we talk about it.
0:31:40 See, that’s the thing about being a related mother, daughter team is that we really do
0:31:45 even when we’re not agreeing on something, believe that we have the same goal.
0:31:49 Yeah, I think that we work it through.
0:31:50 What do you think?
0:31:52 I would absolutely agree with that.
0:31:56 And it doesn’t mean, as Edith said, that we don’t disagree about things, that there
0:32:02 aren’t moments of challenge or tension in any healthy relationship, you’re encountering
0:32:03 all those things, right?
0:32:10 You’re encountering joy, you’re encountering affection, you’re encountering disagreement.
0:32:15 But we do really have each other’s best interests at heart, and I think that’s important for
0:32:19 any relationship period, but especially a co-founder relationship, if you have that
0:32:26 level of trust, and you know the other person is, you don’t have any worries about the other
0:32:33 person’s intentions, you’re able to communicate and navigate three different challenges, and
0:32:37 it’s really been a highlight of building the company, has been getting to work, to work
0:32:39 with Edith, work with my mom.
0:32:47 So it hasn’t all been sunshine and roses, but we know each other so much better.
0:32:52 We know like a third dimension of how we exist and how we operate, which is really fun.
0:32:59 It sounds like you both went into this kind of unusually skilled at the separation of
0:33:07 work and life and making strategic decisions and separating that from your emotions and
0:33:14 you describe, you call Edith in certain situations, mom in certain situations.
0:33:17 Did you know this going into, or has this been a training program?
0:33:18 How did you figure this all out?
0:33:19 There’s a playbook.
0:33:20 There’s no playbook.
0:33:25 There’s no playbook for someone like myself who worked in large institutions previously
0:33:33 for 35 years to roll up into an organization where it’s Jordan and myself sitting in a
0:33:38 two-seater because we didn’t want to spend the money on a three-seater in a shared workspace,
0:33:40 but you pay attention and you learn as you go.
0:33:46 We were looking for our first analyst as an example, and there were so many things going
0:33:47 on.
0:33:51 It was really super early days, and Jordan looked at me, she said, “This was calling
0:33:52 me mom.
0:33:53 There’s only the two of us.”
0:33:59 And she says, “Mom, you ran HR for 35,000 person organization.
0:34:02 You must know how to find candidates on LinkedIn.”
0:34:05 And I’m like, “Uh, that would be a no.”
0:34:10 I said, “I could call somebody who can help me figure out candidates on LinkedIn.
0:34:17 I’m willing to give it a go,” but there were those moments of, “Oh, oh, yeah.
0:34:24 You actually weren’t operating yourself personally every aspect of all of the roles for the last,
0:34:31 I don’t know, 15, 20 years,” but we moved forward and we sit together and we figure
0:34:37 out how to leverage the platform or any other platforms and et cetera, et cetera, but there’s
0:34:40 a lot of that because what do I know?
0:34:48 I know a lot about the things that I’ve experienced, as does Jordan, but I really respect that
0:34:56 there’s much in this construct of standing up medley from ground zero in a new category,
0:35:01 working together as a mother, daughter, co-founder team.
0:35:07 There’s as much that we have to learn and there is no playbook for that.
0:35:10 There’s no playbook.
0:35:17 That’s one of the things we have most in common is our voracious need to try to learn as much
0:35:19 as we can in every context.
0:35:26 We both fundamentally believe we can learn from any situation and from any person.
0:35:31 That shared value has enabled us to work through these types of things and build up that muscle
0:35:33 of communicating with each other.
0:35:38 For myself, I take my growth as a founder, as a CEO, really seriously.
0:35:45 I have had a coach, I’ve been in a group, a group of other founders, I have a therapist,
0:35:50 I take my exercise, sleep, all that stuff pretty seriously and so does Edith.
0:35:57 She does not miss a workout, let me tell you, every day, she doesn’t mess around.
0:36:02 I think that has been a huge enabler for us because it’s not as though we showed up on
0:36:06 day one and then just said, “Okay, let’s see what happens.”
0:36:11 It actually was a super intentional process for both of us to always be trying to learn,
0:36:15 to share feedback with each other, to invest in ourselves and invest in each other.
0:36:22 But this concept of there is no playbook is, I think, becoming the norm, not just for founders,
0:36:27 but for any organization that wants to be relevant today and into the future.
0:36:29 What is the playbook?
0:36:33 What is the playbook when a new drug changes the consumer appetite?
0:36:39 What is the playbook when technology that has been around for decades explodes into this
0:36:43 new incredible world of machine learning and AI?
0:36:49 What is the playbook for next year, let alone for the next 10 years?
0:36:57 And so I think that much of our experiences are similar to what we are talking with the
0:37:02 organizations that we’re working with about.
0:37:08 When you think about what it takes to really build sustainably important organizations,
0:37:13 you’ve got to really have a culture that enables people to connect how they operate,
0:37:17 how they interact, all those things that we were talking about with respect to listening,
0:37:21 communicating, et cetera, to the ultimate goal.
0:37:28 So if everybody walked out of the room and says, “I feel really heard and I feel included,”
0:37:32 but you have no idea what you’re supposed to be delivering and how you’re supposed
0:37:35 to deliver it, that’s not the point of all of this.
0:37:41 The point of all of this is to really appreciate the fact that in any kind of a business environment
0:37:48 where the playbook may be known today and not, you’ve got to have intellectual versatility
0:37:55 to operate and to engage in a very meaningful and steady, quick way.
0:38:01 And that’s what’s super exciting for me about sort of reinventing myself into a founder.
0:38:16 We’ll be right back.
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0:39:54 This is an unexpected question.
0:39:56 So good job.
0:40:06 I think it’s something that I knew, but I would say it’s been accelerated to the top
0:40:14 of my consciousness, and that is, you have to be present.
0:40:18 I think throughout the years, I have three children, Jordan’s the oldest, I have two
0:40:19 boys.
0:40:28 As Jordan described, a pretty intense professional existence, and as time went by and I got more
0:40:35 ownership of my schedule, et cetera, I would show up from Mars, it seems, sometimes.
0:40:43 My longest trip was from New Zealand to Providence, Rhode Island to see my Sunplay soccer.
0:40:53 But I would say that sometimes I was there, and I could have been more present.
0:40:56 But I was doing the best I could, and I was giving myself high marks.
0:40:57 I just shared this story.
0:40:58 It wasn’t that incredible.
0:41:00 I traveled all the way around the world.
0:41:06 But I do think that I’ve learned, particularly because we have to be very deliberate about
0:41:14 the separation of work and our lives, that when Jordan says, “Oh, can I just talk to
0:41:19 you about a few things that are not …” That is focused time.
0:41:21 That is really focused time.
0:41:32 And when I hear, “I’m not having a good morning,” I have to really respect that in a different
0:41:33 way.
0:41:35 I’m kind of a, “Let’s go.
0:41:37 Let’s push through.”
0:41:43 And I think that’s a good lesson for motherhood, that you want to have that relationship where
0:41:52 when someone, when your child says, “I’m struggling with something that you don’t try to fix it,
0:41:55 because I’m a fixer.”
0:42:02 And so that I’ve learned a lot with working with Jordan in Medley, that when she asks
0:42:11 me a question about life or work, she’s actually most of the time not asking me for the answer.
0:42:14 She’s asking for an opportunity to talk it through.
0:42:19 In fact, just the other day, you’re like, “Listen, listen, I just want to talk it through.
0:42:20 I’m not asking you to do it.
0:42:23 I just want to …” Because I’m like, “Okay, I got this.”
0:42:24 She’s like, “No, you don’t.
0:42:25 I need to talk.”
0:42:29 I’ve been studying this for a long time.
0:42:31 So that was a really interesting question.
0:42:37 And I’ll add, we’re expecting our first child in the fall, and we’re having a girl.
0:42:39 So this will be really funny.
0:42:42 I don’t think she can work in the business quite yet, but just give her a couple of years
0:42:44 and it’ll be a three-generation business.
0:42:51 And I will say the thing that I’m trying to embrace entering this huge life transition
0:42:55 is just the unpredictability of everything.
0:43:02 I mean, I have gotten so much more comfortable with both ambiguity, so looking into the
0:43:06 future and not knowing exactly what it’s going to look like.
0:43:12 And also just the lack of control that we really have over things.
0:43:15 You don’t think that you start a fundraised process and then Silicon Valley Bank is going
0:43:16 to collapse.
0:43:20 You don’t think you’re going to launch an in-person community and then COVID-19 happens.
0:43:24 You just don’t think that’s going to happen, but that’s life, right?
0:43:26 Life is pretty unpredictable.
0:43:32 And I’ve built up a lot of confidence, my ability to just navigate unexpected situations.
0:43:38 And I think that will help me in parenting because from what I can tell and seeing my
0:43:43 friends and even seeing, you know, in my family with my siblings and my cousins, you don’t
0:43:47 know what the child’s going to be like, you don’t know what life’s going to give you.
0:43:52 And part of that is part of the fun, I would say.
0:43:53 So I’m looking forward to that.
0:43:57 Do you have any like hold boundaries, like, you know, don’t text me at this time or anything
0:43:59 like that?
0:44:10 I try not to engage and in fact, I don’t actually engage with Jordan about work on Sunday afternoon
0:44:11 at four o’clock.
0:44:18 That was a really bad habit I had because the cadence of the week gets started, I get
0:44:22 myself organized and, you know, I’ve done that for 35 years.
0:44:24 So it was a hard thing to break.
0:44:29 And it was very disruptive actually to Jordan and her husband and, and quite frankly, everyone
0:44:30 around me.
0:44:34 So, you know, and for me, that’s a hard rule.
0:44:39 We were choking earlier about the 630 text.
0:44:40 I don’t really do that that often.
0:44:42 I get up sometimes at five o’clock in the morning.
0:44:47 I don’t do that because that’s a drag, you know, you get up whatever time you get up,
0:44:50 you see this text, you’re like, don’t even have your mind, right?
0:44:57 You got to like, you know, so that’s a pretty hard rule to look if I’ve got something that
0:45:00 really needs to have a conversation.
0:45:05 I don’t put it in a text at seven in the morning, you know, say, Hey, give me a call when you
0:45:06 can.
0:45:11 And the other thing I think is very important in this conversation about first time founders
0:45:16 is that people are watching you, whether you have three people, 10 people, 20 people,
0:45:22 whatever the number is, people do care about the balance that they have in their lives
0:45:27 more every, every year.
0:45:30 And I think that’s really important and it matters.
0:45:37 And so therefore, you know, I, I can get pretty intense, Jordan can get pretty intense and
0:45:43 quite frankly, most of the people on our team can, but I really have watched very closely
0:45:50 how Jordan has been very clear and respectful of people and their lives.
0:45:55 And so that when someone is on holiday and hasn’t been on holiday and is really delivered,
0:46:02 she will literally say, okay, anything that’s going, you know, to this person, you know,
0:46:06 is going to go into an inbox, I’ll be watching the inbox just so you know.
0:46:08 And that’s different from the Goldman style.
0:46:14 Oh, perhaps. Yes. But you know, the interesting question is, what is it like?
0:46:18 I haven’t been in Goldman for, you know, six years now almost.
0:46:20 What is it like now, perhaps?
0:46:26 And there were moments then where, you know, there was no working for investment banking
0:46:31 on Saturdays and whatever the case may be, but all of this is in response to the reality
0:46:38 of who’s showing up and people show up wanting to be human beings with work being part of
0:46:40 their existence, not their only existence.
0:46:46 I’m going to shift to a quick lightning round here about organizational management, which
0:46:47 I feel like you both are experts here.
0:46:52 I’m just going to throw you some questions and we’ll get your hot takes on some of these.
0:46:54 So we’ll start with Edith.
0:46:57 How can companies make meetings more productive?
0:47:00 Make sure there’s a clear agenda.
0:47:04 Hope people accountable for doing the work before they come to the meeting.
0:47:11 And as participants in the meeting, keep it concise, not my specialty.
0:47:18 So I’ll work on that and pay attention to who talks and who doesn’t talk.
0:47:20 Clear follow-ups to conclude.
0:47:24 Jordan, is remote work overrated or underrated?
0:47:26 Personally overrated.
0:47:32 But flexibility, I will say, is really what’s valued from what we’re seeing in terms of
0:47:33 remote work.
0:47:34 That’s a really concise answer.
0:47:35 That’s good.
0:47:37 Let me see what I can do.
0:47:38 Let’s go.
0:47:39 She’s learning from the master, right?
0:47:45 Edith, what is the best way to measure employee success at a company?
0:47:51 The productivity of the company, not just in terms of the bottom line, but in terms of
0:47:58 what the reputation of the company is and how they deliver that profitability.
0:48:00 That’s employee success, right?
0:48:03 That doesn’t happen without employees being successful.
0:48:08 Jordan, when it comes to decision-making, do you prefer using your instincts or data?
0:48:09 Data.
0:48:15 But Edith prefers instincts, so we are a great match in that regard.
0:48:16 Okay.
0:48:17 Why are you pro-data?
0:48:19 Why is Edith pro-instincts?
0:48:28 I think for me, data is more my natural approach, although at this point, I’ve really been working
0:48:29 on this.
0:48:34 I do try to make decisions based off of instinct more.
0:48:40 The way I describe instinct is that it’s actually a cumulation of your experiences.
0:48:46 Instincts are informed by data, but I think to start, my natural inclination is, well,
0:48:50 I want to understand and get all the information, but when you’re running a startup and over
0:48:54 the past five years I’ve learned, you really can get all the information, so you have to
0:48:55 use both.
0:49:00 Edith, how important is DEI, and do you think it’s something that every company should
0:49:02 be implementing?
0:49:10 Every company that wants to be a relevant company needs to invest in their people and
0:49:16 create environments where everyone can thrive, and that’s everyone.
0:49:22 That’s people who are part of the majority, people who are from different schools, from
0:49:25 different languages, cultures, etc.
0:49:29 Many people have asked me, particularly in the last year, what’s going to happen with
0:49:30 DEI?
0:49:31 Is it going to be over forever?
0:49:32 I don’t know.
0:49:33 Do you want to be an excellent company?
0:49:37 If you want to be an excellent company, you continue to do the work.
0:49:39 You can call it what you want.
0:49:40 You have to do the work.
0:49:46 Do you think it’s been politicized in a way that’s been destructive to organizations?
0:49:56 I think that it has certainly been politicized, and I don’t think it has been particularly
0:49:59 productive.
0:50:07 I don’t think it’s been as disruptive as people might think, because strong organizations
0:50:13 with strong cultures understand how important it is to extract excellence.
0:50:15 People ask me, “What should we call it?”
0:50:21 I said, “Why don’t you just call it excellence,” because that’s what it means to have a truly
0:50:26 diverse organization from a number of different perspectives.
0:50:33 All the organizations that I’ve worked with and continue to talk to, they’re moving forward
0:50:36 because they want to be great.
0:50:42 To be great, you have to have the diversity of experience, perspectives, culture, sexual
0:50:43 orientation.
0:50:47 The list will just continue to get longer and longer.
0:50:49 What an exciting opportunity.
0:50:55 Jordan, this one came to me because we were discussing the idea of bringing a full self
0:50:58 to work.
0:51:04 Is there space for political opinions in the workplace, and should leaders be taking
0:51:07 up political opinions if they choose?
0:51:11 It really depends on the company and their culture and their values.
0:51:16 For some companies who have made statements that they do not want to engage in the political
0:51:21 dynamic, those companies are going to attract people who want to work in those environments.
0:51:25 On the flip side, companies where leaders really are taking a stand or voicing their
0:51:31 opinion in whichever direction, the same thing is happening.
0:51:34 People are going to be drawn to working at those companies because that’s a value that
0:51:37 they care about.
0:51:43 Finally, I think that there needs to be a way for leaders to acknowledge what’s happening
0:51:48 in the world and give space for employees who are probably processing in some way or
0:51:49 the other.
0:51:54 That’s what we try to do internally at Medley is really just giving space for people.
0:52:00 I do think that we’re just going to see some real self-selection in terms of employees,
0:52:03 and they’ll vote by going where they want to work.
0:52:08 Real questions from me, and thank you both for being generous with your time.
0:52:11 Edith, actually, we’ll start with Jordan.
0:52:13 Some advice to our listeners.
0:52:18 We have a lot of female listeners on the show.
0:52:21 Scott seems to think we don’t, but we do.
0:52:25 Do you have any advice on how to be a good daughter?
0:52:31 I will say as you grow up and as you encounter different experiences, embrace the fact that
0:52:34 your relationship with your mom might change.
0:52:35 That can be exciting.
0:52:36 It can be a good opportunity.
0:52:37 Are you a dad?
0:52:38 Yes.
0:52:39 You’re right.
0:52:43 Or you’re a dad with your parents.
0:52:49 Embrace this fact that your relationship with your parents likely will change over time.
0:52:53 I think accepting that can really enable new types of relationships to build with your
0:52:54 parents.
0:52:56 Edith, any advice on how to be a good mother?
0:53:06 Not to get a little syrupy here, but love unconditionally because it’s a ride.
0:53:14 If you make that the core of your relationship, it becomes multi-dimensional.
0:53:23 It becomes positive reinforcement, feedback, direction, and just some good hugs from time
0:53:24 to time.
0:53:26 It’ll all be okay.
0:53:33 But if you start with that center and you develop trust of caring, anything that comes
0:53:39 your way, you’ll be able to navigate and things will come your way.
0:53:40 I love that.
0:53:44 Jordan Taylor and Edith Cooper are the co-founders of Medley, a group coaching platform.
0:53:45 Thank you very much both for joining me.
0:53:48 Thanks for having us.
0:53:55 Our producer is Claire Miller, our associate producer is Alison Weiss, and our engineer
0:53:56 is Benjamin Spencer.
0:53:59 Catherine Dillon is our executive producer.
0:54:02 Thank you for listening to First Time Founders from the Vox Media Podcast Network.
0:54:05 Tune in tomorrow for Prodigy Markets.
0:54:15 [Music]
0:54:22 [Music]
0:54:32 [BLANK_AUDIO]
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.
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