Amy Errett, Madison Reed CEO: A Leader Who Never Ignores Her Intuition

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Amy Errett named her company after her daughter as a reminder that the values we want for our children—integrity, purpose, and authenticity—should be reflected in our business practices. Enhancing her analytical training, Amy’s superpower is following her intuition, which she says, “has never been wrong.” She encourages women to balance the importance of data with those inner insights that often see around corners before others do.

Join Shelley and Amy as they take us on her personal journey from investment banker and venture capitalist to successful entrepreneur. Amy shares how she navigated unanticipated experiences like getting fired in a hotel lobby to ultimately discovering her true calling as a business leader who puts people first. Don’t miss this inspiring conversation with a passionate leader who believes that following your gut, caring deeply about your team, and leading with love aren’t just nice ideals, they’re the foundation of building an enduring, successful business in today’s complex, transactional world.

Special Guests

Amy Errett: CEO, Madison Reed

Transcript by Descript:

 Hello, Amy. Thank you so much for joining our podcast today. I am super excited to have you here and I think you have an incredible story and one that should be told. So I’m gonna jump right into asking questions.  And I know when I met you, I was super fascinated by your background. So you have a very interesting journey because if I remember correctly, you came from the VC side of the business

I love your story of how and why you decided to open your own company, Madison Reed. So can you tell us a little bit about that?  Yeah. F So first of all, Shelly, thank you so much for having me. I’m really excited about this.  Yeah. So my journey is one of, uh, three time entrepreneur, then venture capitalists than entrepreneur.

And people ask me all the time, why is that? And I.  I really like operating. It’s not that I don’t like investing, but I really enjoy operating because I like  leading and I like creating the possibility that other human beings have sort of life changing experiences through the companies that somebody like me hopefully builds successfully.

So, you know, mine is a story of, uh, being a bank investment banker, and as I then deciding to, you know, be an entrepreneur and start my own company, which I did, and sold it to a public company and then went and started, you know, helped. I was a senior person at this little company at the time, called E-Trade, which turned into a much bigger company and I was there in the rise in the not so good moments of, you know, 2002 and lived through that.

And then I had my career stumble as I call it, which.  Everybody, you know, has at least one of those. And in, in retrospect, it’s a great thing  where  I was, um, hired to take over a founder led organization that had been in business a long time. And, you know, I thought that I was being very successful, but ended up getting fired  in a hotel lobby, not knowing that I was gonna get fired in.

Even though they had been gone. So I kind of learned something there. And then I became a venture capitalist  because I, um, you know, had an operating background and I think my partners at Maveron saw that. And so I opened the Bay Area office of Maveron,  where it’s a Seattle based firm. You know, one of the founding partners is Howard Schultz.

So I had the good fortune of, uh, working in a consumer focused early stage venture fund.  And did that for six years and loved it, but kind of had kept having this experience that I’d go to board meetings  and I was wishing I was the CEO rather than the vc. And so, uh, I just decided as the firm was,  you know, going to  raise a new fund, that it would make more sense for me to decide to become, uh, entrepreneur again.

And that was the genesis of. How I came up with this crazy Madison Reed idea.  I just love it. I think that’s a fantastic journey. So today’s workforce has really changed drastically, especially in the last few years. Priorities have changed with workers. Work-life balance has become certainly more important, and also employees really wanna be part of that bigger picture of things.

How do you empower and support your team members to excel in today’s? Challenging environment. Yeah, I think that the first thing I, I’d say is that  one of the greatest attributes I think a leader needs to have is empathy. And  the reason that I say that is that I think if the pandemic taught us one thing, it taught us that, you know, curve balls happen in big magnitudes

And that understanding people’s life  holistically. Like, it, it, we talk about this at Madison Reed all the time, that we wanna bring our, I want everyone to bring their full selves to work, right? So in order for full selves to work to happen, you have to accept all the things that a full self has, including, you know, home life, anxiety, health, all those things, mental health, physical health and aspirations that people have

And what, what is the relationship that people have to work that might be different than the relationship?  People generationally  in my generation, have to work, right? So for us, it was a watershed moment. And the pandemic, we had always been a company that was really focused on, on our cultural values. I tell the story that the values were, the values existed to fourth day into the company, but the hair color and the tube didn’t  because we just knew that we wanted to set forth who we were and who we are.

And how that  created a roadmap, as I call it, to every decision we would make and all the hires we would make. So we tend to, in our case, um, recruit people that are purpose-driven, mission-driven. They believe more. They believe as much as the efficacy is the product as how we do the work we do, and what we do culturally and how do we treat each other, and what do we want the experience to be around personal growth, financial growth, and professional growth.

So as the pandemic happened, all of a sudden this notion of going to an office and doing things that were more traditional, just, you know, it was just thrown upside down. And at the same time, our business doubled in six months. Wow.  So we had this dilemma, right? We had a dilemma of good fortune in our company while there was massive life anxiety happening for our workforce.

Right? So, hold  once.  Taught us a lesson that if you talk about bringing your holistic self to work, you have to understand that everybody has different experiences. And so we did a lot of things right. And I, and I talk about this and I think, and there are things we continue to do. We started offering, um, mental health benefits.

That’s  great. Mental health care.  Um,  and sort of partnering with a company that did that anonymously online for people who wanted therapy. We started to be more conscious about,  you know, times of meetings, days of meetings. You know, realizing that if you had little kids at home, it just wasn’t gonna work that same way.

And so we  addressed the way the business sort of operated, rather than saying to people,  it’s just the way it is. Make it work. Right? We listened and we did some things.  Hundred percent’s  moment now.  We’ve had some good fortune of the culture. Not, I mean, of course culture is harder when you don’t see each other,  but we have a lot of rituals in the company that create.

For instance, I have lunch with the company every Wednesday at 1215, no matter where I am in the world.  I love that, and I have coffee with Amy every Friday. At 9:00 AM Pacific time, and we don’t, we, it’s the lunch is mandatory. We talk about what’s happening in the company. We give shout outs to people. We welcome new people.

We say goodbye to people that are leaving. And on Fridays, it’s just a life question that I pose. It has nothing to do with work. And it’s all about, you know, can we find ways to get to know each other on a deeper level? So I think that there’s no simple answer to the question. About, you know, how do you perfectly adjust your culture to a new workforce?

I think the first step is recognizing there is a new workforce and recognizing  what it is in your culture you need, that fits for recruiting people and retaining people and promoting people, and career developing people. Many, many people in our company have coaches that we pay for,  um, because we’ve also learned that.

You know, someone’s development is not only about what the organization can do, but there’s something somebody needs to talk about that are outside the realm of what’s happening at work. Right? We create listening circles. We our, you know, management team has a coach that we, we work with in, in-person sessions that are about conflict resolution, building trust in the circle,  so.

How do we say hard things to each other and still get our business done? So  I guess my, you know, long answer that is maybe a, maybe complexity into simplicity is you have to invest in people as human beings fully. And sometimes that requires understanding things that may be different from how you worked or, you know, I had never worked in a remote environment before.

I was going into an office kind of person and. So I’ve had to adjust my own level of how I expect things. Yet we changed our routines and the things that we did that created what I would consider be the container that keeps the culture alive. And I think that’s a,  that consciousness raising is something that leaders have to understand.

Lots of businesses are saying, now you must come back.  Like that is the current piece, uh, of, of news. And I think everybody needs to understand their workforce, their culture, what works for them, and there’s not one simple answer.  Being leader means that you have to sometimes make decisions that are hard a lot of times every day,  and yet can you do it with empathy and compassion?

Yeah, it’s definitely not, as you said, it’s not a simple answer and it’s even more difficult to execute such a  very thought out and engaging employee culture in the company. So I’m wondering, can you share with us maybe an example of a difficult decision you had to make and  the thought process behind it?

Yeah, so when the pandemic hit, we had 12 stores. We had a very vibrant. We only had 12 stores in March of 2020. We had 87 now. Okay. I know. I’m surprised. And yeah, and,  but we had, you know,  team members that worked in the stores.  And so what was a different, difficult decision? Like, do we, our online business was going crazy.

Our relationship with Alta was, you know, on fire because.  As you remember, every woman in the world now needed to color their hair at home. And we, we did gain, you know, out, you know, sort of outpaced competition in market share ’cause everyone had heard about the company. But now salon goers were needed to do something and, and we were very fortunate and blessed that they came to us,  but we had  people that we didn’t know how long stores would be closed.

It was expensive to keep them.  And we kept them  and we,  we, most of these people were certified licensed colorists. And so the thought process was what was in the ethos of the company first  was, could, could I look in the mirror at night  and really feel like, well, that was just about money, sorry.  Or could I look in the mirror at night and think these people have families.

There were anxiety. They’re afraid to get sick. What does this mean for their livelihood?  Is that in the mission and purpose and oh, did I have another role that was really valuable? And so we shifted all of them in a three day period from working in stores to teaching them how to take customer service calls because  our call center was always certified licensed colorists.

’cause we give advice and course color match.  And so I said, well listen, there’s a.  People And are, we we’re under like a waterfall of customer service,  inbound. ’cause our business was exploding. Could we teach these people? So here’s what we did. We um, sure. Was it the most economical decision for the company?

Probably not. But was it a decision that set in motion that we are who we say we are. We effectively bought a whole bunch of Google Chromebooks, sent them to the, we gave people a choice. We said, here’s what your role could be, or you could decide  to pause your employment and as soon as stores open, we’ll rehire you

The vast majority of people took the opportunity to join. Many of them learned technology skills over the, we bought headsets, Google, Chromebooks. I think we wiped that out in the Bay area, sent it to everybody. Then I think in a three day period, people over a weekend were trained how to use the Chromebook, how to answer the phone, how to get back on chat.

And we just supercharged that. And when stores reopened, many people went back to stores. Handful of people are still in our call center ’cause they liked it better and learned technology skills. But my point was hard decision, right? Like not obvious yet. Um. One that I, I feel really good about. Wow, that’s a great, I can’t believe you train a hundred people in three days.

That’s unbelievable. Kudos to you and your team for that.  Well, yeah.  Well, thank you. You know, we,  I think it, I think if you believe in team first,  then every decision goes through that first lens. So, Amy, let’s switch gears here and talk a little bit about mentoring.  Have you had any mentors who really influenced you, your leadership journey?

I’d love to hear who has really made an impact on you. Yeah. Uh, I think there’s quite a few. I think early in my career there were some  very, uh, when I was a banker, there were some senior women that had fought their way through the jungle to get to be senior women, and they were very influential in helping me think through career pathing and how to  deal.

In a finance world that primarily was not women dominated. I had a, a male mentor at the bank I was at who  actually, you know, helped me a lot navigate and, and effectively helped me think through the fact that maybe you want to be a entrepreneur rather than work in a large company.  And I’d say that  in addition, believe it or not, some of my investors that are on my board have been mentors.

They’ve been, people that I’ve been able to confide in,  have helped me think through things that are not just in the boardroom, but I’m a full disclosure person. And so, you know, helping, you know,  how do I say like, thinking out loud, talking out loud,  thinking while I’m talking is, is kind of how I process.

And then last but not least, I have a life coach now. And that person has been very important in my own development of understanding where my strengths are, where my blind spots are, what are the things that trigger me? How do I deal with stress? How do, how do I show up for other people differently? And it’s been incredible for me.

It’s been going on for about 18 months and I feel like my life is very different since I’ve engaged with the life coach. Oh my gosh. That’s amazing. Well, I know you definitely pay it forward. You’ve come to speak to my class at Fashion Institute of Technology. I know you’re very fond of helping students.

What other things are you doing in terms of your mentoring others, because I know there’s a lot of women that could really benefit from all the things that you do and your leadership.  Yeah, so you know, the first thing is that,  you know. I’m involved with both of my alma maters, university of Connecticut as an undergrad  student, and I’m on the foundation board there and help start a student led venture funds.

So that’s been wonderful and which has been, you know, like an incredible experience to TP people, how to  teach young people and many of them women, what it’s like to invest early in their careers. And that’s just been great.  I’m involved at Wharton and teach classes there  and often all the time after these classes, there is a line of, there are a line of women that are asking for help.

And  I have a process which is, you know, I give you my email address, email me your issue. I can’t spend a ton of  time on the phone ’cause I just don’t have access. But if you email me, I’m gonna get you answers to those things. And I have lots of women that have. Continued in their careers and just check in with me about  those things that are important to them.

I teach a class at Stanford out here at the gsb. Wow.  And that’s been super helpful for me. ’cause every time  it’s a case about Madison Reed that that happens. I learn something and there’s always women coming after that as well to help. And then last but not least, you know, I’m a,  a part-time venture capitalist still, and so.

I both mentor some of the women that are at the VC firm and certainly  have played a role in angel investing and getting involved in women early in their careers, later in their career. So I have a full plate. You too.  You know,  I mean, it sounds bizarre sometimes I think to myself like, oh, you should do more

It’s like an tion. But I  people, you know, women helped me early in my career and. I feel like we stand on each other’s shoulders and it’s an important factor to  be somebody that can give you guidance and, you know, give back  and it’s an important factor to seek that out on the other side. Right. Don’t be afraid to ask.

Yeah, absolutely. If you do you, what is probably one of the most valuable lessons you’ve ever learned that you’d like to share with aspiring female leaders? There’s two things. If I can note them, I’ll, I’ll make ’em quicker. One.  I’ve struggled my whole career with doubting my gut. And I’m a person that, you know, I was trained at Wharton and analytics  head things, you know, spreadsheets, head things, you know, decision trees.

Right? Exactly.  And as a business person to venture capitalist, like, look at the data, the data will tell you everything. Right?  Um, so I have that tendency, and yet my gut is amazingly speaks to me all day long. So the first thing is that I’ve learned that following your gut is just absolutely essential. As entrepreneur, you, the great companies are the things that come out of an I, I wanna use this word carefully.

They come out of sort of crazy,  right? Like we’re kind of off a little bit. We kind of see things that other people can’t see, which is why we start companies and we make bets of  seeing around a corner before we get around a corner. Everybody else gets around a corner, and that’s why the business can be successful.

So that’s one. Trust your gut. You’re not great. You’re, you’re, you’re, you’re, it, it speaks to you and it’s real. And then I think the second thing that I wanna say to people is to women in particular,  don’t be afraid to ask. And you’re worth it. Love that. Because as moms, as professionals, as partners, as.

Probably aging parents. Like there’s certain age group I’m in, my parents aging. You are what I call, we are what I call at a stage in our life called the sandwich generation.  We’re right in the middle of parents aging and our obligations and our children, and we come very low in our own sort of hierarchy of taking care of ourselves.

Right? Yeah. It’s just the way women are wired.  That’s the roles we’ve absorbed. And for many us of us have enjoyed enormously, right? Yeah. So take care of yourself, but ask. ’cause the first place you start is, do I deserve success? Here’s what I’ve learned.  Most of us are much less on the surface, Shelly, it appears that we’re scared to fail.

And I  have learned true from my own journey is that I’m more.  Scared in some ways to succeed  than I am to fail.  Failing is what we’re wired to do, right? That’s what we’re prepared to do, who prepares us to think enough of ourselves to succeed.  And I think that’s kind of, and I think the universe goes when you get your head right at happens,  right

So  that’s what I urge people to do. Believe in yourself, you deserve it.  Yeah, definitely.  So I’m gonna end with, uh, a couple rapid fire questions. So I’m just gonna ask you a quick question and you just, thank you, gimme an answer. Okay. What one piece of piece of advice would you give to female leaders that are currently working?

Go for your dreams. Love it. What three tips would you give? Students are emerging leaders. You don’t have to be good at everything that school teaches you that you should be, you know where your genius is. And construct a happy life. And my last one is, what’s your legacy? What do you wanna leave behind for that next generation?

I want people to understand that love is the most powerful human emotion and it has a place in work, and it has a place in all parts of your life. And if you love  good things happen.  Oh, I love that. Oh my gosh. Thank you. Okay, one last question. This is the last one. Sure. This is a fun one too. It can be related to work or not related to work.

Yeah. Okay. You ready? What’s your secret power Following my gut, which has never been wrong. Oh my gosh. Thank you so much Amy. I really appreciate your time. I recognize how busy you are.  Thank you so much for coming. I really appreciate it. You’re welcome, Shelly.  I cherish, uh, our friendship and I thank you for the interest in me and Madison Reed.

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