Empowering Teams and Taking Risks

In this episode…

Nic Cary interviews Katharine and they discuss the lessons learned during her career journey including:

• The importance of surrounding yourself with talented, diverse teams and empowering them to succeed.
• The value of embracing risk and stepping out of your comfort zone to discover unexpected opportunities.
• The necessity of owning mistakes, learning from them, and fostering a culture of resilience and accountability.

Sponsor for this episode:

This episode is brought to you by Sky’s The Limit, one of the largest nonprofit programs for underrepresented young adult entrepreneurs in the US. Sky’s The Limit is a quick-growing digital platform that connects entrepreneurs with their peers, volunteer business mentors, training resources, and funding.

Our goal is to develop the social capital that founders need to chase their business dreams.

To learn more, please visit www.skysthelimit.org today.

Episode transcript

INTRO (00:04):

Welcome to the First Buck podcast where we feature stories about entrepreneurs and the people who support them. Now let's get started with the show.

Nic Cary (00:22):

Hello and welcome to The First Buck Podcast, brought to you by Skysthelimit.org. We feature stories about entrepreneurs and the people who support them. Today we're joined by Katharine Weymouth, Chief Operating Officer at Togetherly Parents, a community for parents with struggling teens and young adults. Ms. Weymouth also serves on several public boards, bringing her experience as a former CEO and leader responsible for transforming a business in the midst of a large scale disruption into a truly digital platform. In addition to her startup experience, Ms. Weymouth brings extensive executive leadership and strategy experience gained through numerous leadership positions over 17 years at the Washington Post, including seven years as a Publisher and Chief Executive Officer, and four years as VP of Sales responsible for over half a billion dollars in revenue annually. Ms. Weymouth also serves on the board of many other organizations. She had a time as an assistant general counsel at the Washington Post.

(01:16):

She has a JD from Stanford Law School, a BA from Harvard, and she serves on the board for Public Services Cable, one Graham Holdings, Xometry and Sequoia Mutual Fund. And besides all of that extensive professional experience, she also is an incredible philanthropist, serves on the nonprofit Meadow Reproductive Health and the Philip Graham Fund and is an advisory board member of the C Cipher Brief. So we had an amazing introduction to her already and we're so excited for you to be on the podcast today. We have a little tradition around here. We always like to learn. How did you earn your first buck?

Katharine Weymouth (01:52):

Well, thanks for having me. I was thinking about that. I think my first job was in college working as a barista to make a little cash on the side, and I actually really enjoyed it. It was a great way to meet people and get a little extra cash.

Nic Cary (02:09):

I love that. So from helping people get a little bit of caffeine to get going in the mornings, talk to us a little bit about what happened after college and how did you sort of start to think about entering the workforce or beginning your career?

Katharine Weymouth (02:23):

Yeah. Well, I was an English major, so it was not a practical degree in any sense, and I knew that, and I didn't really know what I wanted to do when I grew up. So I did what a lot of people do, which is I decided to go to law school and get a more practical degree. So I ended up, I think people had all my life had told me I would make a good lawyer. I don't know why they told me that, but I was like, okay, I'll go to law school. So that was kind of my path to getting a regular job.

Nic Cary (02:58):

So we go to law school graduate. What does entering the world look like at that point in your life?

Katharine Weymouth (03:06):

Well, it's kind of easy if you just follow the path. You get a summer job at a law firm. If you do okay, they offer you a permanent slot. So I started, actually, I clerked for a judge for a year, which was great experience. And then I moved to Washington DC and joined a law firm. And I think of it for me as sort of my marine bootcamp. I cried for the first eight months. I think I had law school unfortunately, had not prepared me in any way for actually working as a lawyer, and I had to learn a lot on the job, but it was an amazing group of people and I learned a ton and I actually loved it. So we just practiced general litigation and they kind of threw you in and you worked with a partner and figured it out as you went along.

Nic Cary (03:55):

It is one of the things I think we hear a lot from professionals that have had pretty interesting and difficult careers is that there's usually a period of time early on where things are very difficult and they have to enter the workforce. They may not know everything, and some people deal with getting a lot of adversity at them in different ways. What were some of the, how did you approach that because being told you're not good enough or that you're not doing it right or people take criticism sometimes very difficult in a difficult way. So how do you get through all that?

Katharine Weymouth (04:29):

Yeah, that's a great question. I think, and maybe this is especially true of girls and women school, I was good at school. I was good at following instructions and doing the homework and getting it in on time and all that kind of stuff, but that doesn't prepare you for the workforce. And I guess I didn't really have mentors at that time who could tell me how to find a mentor at the law firm, how to ask advice of somebody, what to do when you mess up. And I was kind of used to getting good grades and doing so I will never forget, but it was a great lesson. A partner pulled me aside. I had paired some kind of document and he handed it back to me and he said, there are typos in here. And he's like, you need to go back. He's like, details matter.

(05:15):

You need to go back. You need to review this and do not hand me another document with typos in it. And part of you is thinking, oh, whatever, it's just a typo. But it was a great lesson. It's annoying. Nobody wants to proofread something after you've written it or read it twice or edited or whatever. So it was just a lot of lessons like that. Or one time I was in a deposition and the partner was taking the deposition and it was a divorce case and the partner had to run out of the room for something and he was like, Catherine, you just take over for me. And I was like, what? I don't dunno what I'm doing, but I appreciated that because that's the only way you kind of learn is a little bit being thrown in the deep end and then just putting one foot in front of the other and maybe you make a mistake, but it's okay.

(06:01):

So there was a lot of stuff like that. I remember we had a trial in one case, and I guess I secretly am still, I was an incredible introvert. I was so shy, I couldn't do public speaking at all. And the partner told me that I had to cross examine or examine one of the witnesses. And again, I was utterly terrified, but I did it. And I even got feedback later from the jury that they really liked me. And so it was scary. It was hard, but it was so good for me and I appreciated that the partner believed in me and pushed me to do something I wouldn't have chosen to do on my own.

Nic Cary (06:42):

I like that story a lot. Thank you for sharing that. I think those first sort of mentors, advisors, coaches are sometimes tough bosses that can show a little bit of confidence. It helps sort of open the aperture up of one's possibilities. And I think it's important for young people to know that sometimes being criticized or told that you're not doing a good enough job, isn't a personal attack. It's a potentially opportunity to just improve. And if you can see it as that, it helps basically invite more of it in a way that you can sort of improve over time. And so thank you for sharing that. Yeah. You mentioned something important, which is how to go about finding people that can be those advisors, coaches, or mentors. And it's not always easy, especially maybe if you are a little bit introverted. So what advice might you give young people for finding those kind of professional mentors across their careers and who should they be looking for?

Katharine Weymouth (07:33):

Yeah, I think that is so, so important and can really change your career in so many ways. And I'm not a believer in formal mentorships in companies when you're just assigned somebody because that doesn't always work. I think it's about looking around wherever you are working and finding people that you sort of admire. And in my experience, if you just approach somebody and say, Hey, can I buy you a cup of coffee? I'd love to get your advice. People are actually usually flatter. They usually are happy to help somebody and then just ask them, this is what I want to do, or this is why I want to be in five years. Do you have any advice about how I should get there? And then if you gel, then they can become a friend and a mentor for a long period of time. And so I think it's great to find people like that around your company.

Nic Cary (08:28):

Amazing. All right. Great recommendation. So earlier we learned that you earn your first buck making coffees. What was the first puck you ever donated or gave away to charity and why?

Katharine Weymouth (08:39):

Oh, gosh. I'm not even sure I remember, but I'm sure I have a very soft heart. I'm a deep empath, so it was probably something around animals. I'm a total dog person, but I think I am blessed. I came from a family with means, and my grandmother was the owner and publisher of the Washington Post. I had grown up around strong, successful women. My high school friends used to call us the Amazon family because they viewed us as these tall, strong, contented women, which we were. So I think I had always been raised with a sense of, you're incredibly lucky. You've been given an amazing education and incredible opportunities, met really interesting people, and you owe society a debt. You need to pay it back. So I think I always had that sense. And that has also, it is a gift and actually giving, if you believe in whatever the charity or organization is doing makes you feel good. And I think it is part of our responsibility for those of us who have had opportunity and success and they're able to do it.

Nic Cary (09:53):

Cool. So I guess the apple didn't fall too far from the tree in your case, which is amazing. Let's talk a little bit about your experience at the Washington Post becoming a CEO, and what were some of the maybe steps that if you could reflect on that sort of helped prepare you for that? You learned some public speaking, doing battle in court and complex litigations and then negotiations and imagine taking care of budgets and hiring people. How did you sort of expose yourself to those things?

Katharine Weymouth (10:23):

Yeah, I think what really changed for me, I went from being a lawyer and at some point, somebody from, I had moved to the Washington Post as an attorney, and after four years of doing that, somebody from the then vice president of advertising reached out to me and said, Hey, would you be interested in coming to the advertising department? And I was like, what? I knew nothing about advertising. I knew nothing about sales,

Nic Cary (10:54):

Which is the core business actually of how

Katharine Weymouth (10:56):

Totally core business operate. At the time, I was working@the.com entity, which was a separate company, actually Washington post.com, and everybody was like, print is dead. And she wanted me to go back to the newspaper, but I did it. I just took a leap of faith. I was like, you know what? That was the revenue driver for the paper at the time. I was like, that's the way I'm going to learn the business and I'm just going to take a leap of faith. So I did it and I started calling on auto dealers and carpet makers, and you name it, I called on them and I actually loved sales. Sales is just people, it's just you go in and you learn about their business and how can I help you grow your business? So if you had asked me before I joined advertising, would I ever end up doing sales, I would've laughed.

(11:50):

So I think the lesson for me, and I often do share this with young people, is don't plan your whole career out 25 years. You never know there are going to be pivots and turns. And I would say, be open to that. You actually don't know what you might end up loving. So I started in advertising and then I graduated. I had my first job as a manager running what we then called the help Wanted section, now the job section. And again, I was terrified. Suddenly I was managing 40 people. I had never managed anybody and it was in the Help Wanted section. And so I would go to cocktail parties in Washington DC and people would ask me what I did, and I would tell them that I ran the Help Wanted section and they would run as fast as they could away from me because it sounded so boring.

(12:36):

But again, I loved it. I learned so much. Again, it's about people. How do you motivate them? And at the time, we were in a total battle with suddenly the internet had come along. And so we were in a battle against Hot Jobs and Monster and Career Builder. And so it really was a very strategic job of thinking about, we have this great print product that makes a lot of money. How do we transition this to the digital world and do it in a way that serves our customers? So I just started doing one thing after another, and then I ended up running the whole advertising department, which was 300 people and half a billion dollars in revenue. And I had no plan of becoming publisher and CEO that was not on my radar. And at some point, my uncle started talking to me about whether I would wanted to do that or was ready to do that.

(13:27):

And all I could think was, I'm totally not ready, not ready at all. But I also had a vision for what I thought we should be doing as a business. And he finally said, actually, it was somebody else who said to me, Catherine, if you're going to make those changes, only you can make those changes. So if you want to make them, you got to step up and do it. So I did. And again, I was completely terrified. I still was, I guess I had learned some public speaking as in running the advertising department and gotten a little more comfortable doing that. And my grandmother had told me that's the only way you're going to get comfortable doing it is just do it. Just do it. The more you do it, the more comfortable you get. And I definitely learned to take some deep yoga breaths before I give a speech and just slow your heart rate down. So that was kind of my path.

Nic Cary (14:16):

Okay, so just do it. And stepping into the uncomfortable, I think one of the things you mentioned was sort of when you talk about unique management or leadership style and sort of developing that over time, one of the hardest things for business leaders is always, I think figuring out how they're going to hold people accountable and what their structure for doing that is. One of, we listen to a lot of young entrepreneurs talk about how difficult it is when they hire their first employee or their first few to get them really contribute. And I wonder if you'd had any words of advice around how to make that. I would say that decision earlier on or not about when you work with someone or when you let 'em go, those are hard things about hard things, but I'd love to hear what you think.

Katharine Weymouth (15:01):

And not just from my own experience at companies, but also sitting on boards of both large companies and small companies. I've seen all kinds of different leaders from startups to very established businesses. I am a firm believer in identifying talent and just surrounding yourself with great people. I remember when I first took over the helm at the Washington Post, my uncle said to me, Catherine, you don't have to be the smartest person in the world, but you have to surround yourself with the smartest people and then listen to them. And I think that's the key part. A lot of people say, oh yeah, yeah, no, I'm happy to get different feedback and people who disagree with me, but it's not often true. A lot of people really like to surround themselves with yes people, but in my experience, that doesn't work very well. And so I really just tried to surround myself with brilliant people, way smarter than me who knew more than I did.

(15:57):

And we would agree on what direction are we going, what's our strategy? What are we trying to execute? What are our measurements, our key indicators and stuff. But once we agreed on that, I'm a believer in let people run, let people run, let them come to you with ideas, and you also have to be, you're going to make mistakes. And when you are the leader, you have to own those. And I had several very, very public stumbles, but I very quickly said to my team, you know what? I'm the CEO, I own that, but we cannot stop taking risks. So it's great to take credit when things go well, but you also have to take credit when things don't go well. Yeah,

Nic Cary (16:42):

Maybe someday you'll have to run the podcast. The buck stops with me. No way. I like that. Okay. Yeah, so amazing. Own your mistakes and basically foster an environment where you accept that failures happen, you learn from them, but you have to keep moving forward. So you operated that business at such a tumultuous time in some ways where the internet was coming along and arguably disrupting print media and everyone said it would maybe cause those major institutions of knowledge to potentially disappear. And I'd love to hear your perspective like now, 20 years since the.com sort of bubble and where's it headed? Is it more important than ever to maybe have a bit of a slower media that can actually analyze perspectives and study and do deep research in longer form thinking? And in this era where we've sort of become addicted to very short form information and people don't seem to be able to analyze complex issues as easily, I'd love to hear one maybe with your perspective on how the news media is going to change or what it needs to deliver in this day and age, because I think very few people have a vantage with as much expertise as yours.

Katharine Weymouth (18:02):

Yeah, I mean, I definitely do think it's more important than ever, and I wouldn't say slower necessarily, but I would say trustworthy and reliable journalists who are checking with multiple sources who don't publish a story until they know it's true. So I do think good journalism is more important than ever. I think the challenge is for a variety of reasons. I mean, as you said, people have gotten used to very bite-sized snippets. My kids probably get most of their news from LinkedIn and TikTok, which frightens me a little. But I think the challenge is the media has lost the sort of, so-called mainstream media has lost the trust of a lot of people. And I hear that all the time from really savvy business people. And I think some of that is the Trump administration calling them liars and whatnot. So I think it has really eroded trust. So I think the media has to re-earn that trust. They do have to make sure that readers understand where the facts are coming from.

(19:08):

I also think we have to reach people where they are, right? I mean, if only the 1% are reading the So-called mainstream news, then it's not reaching people. So certainly the pose, the Times, the Wall Street Journal of many others are doing everything they can to be on every platform to explain to readers how we vet our sources, why we use an anonymous source if we do. But I think it's a challenging time. Our country is so divided and people are getting their news, and now we have AI and misinformation and people don't really know what they can trust on the internet and what they can't. So I think a lot of it is just educating people about which sources they can trust, which sources they can know. And are organizations biased? Yes, of course, they're people, they're human beings, but the mainstream publications really work hard to be as objective as they can and just share the facts with their readers.

(20:05):

But the business model is incredibly challenged, and that's not changing. The internet completely disrupted the business model, and that challenge is not going away. And it's why of course we ended up selling the Washington Post to Jeff Bezos because we knew that we needed an owner who believed in the mission, who could invest in it, who could take it private. So you didn't have to every quarter report your results and how much advertising sales were down and all that, and who could invest in the newsroom. So it was a hard sad decision for my family, but I think it was the right thing for the post. So I think the business model is challenged, and that's not changing. People don't want to pay for news. They view it often as a commodity. So I think that challenge is just going to continue, unfortunately.

Nic Cary (20:54):

Yeah, what you guys went through is so interesting because one of the hardest things a company can go through is to actually pivot its business model. One day you're making money this way, and then you're watching revenues basically shrink and you have to build a completely different thing potentially. And so executing on that almost requires creating a new company. In some ways, it's one of the hardest things

Katharine Weymouth (21:14):

To

Nic Cary (21:15):

Do. We did,

Katharine Weymouth (21:15):

I mean, we did, and my uncle did create a new company. It was totally separate, and he viewed it because he was like, the mothership will crush it. So he did start Washington post.com, I think very smartly as a new company. So we did all that. We did pivot. The challenge was how to make money,

Nic Cary (21:31):

And that is always, I think, the crux of it. At the end of the day, the organizations have to be sustainable to survive, and then sometimes they require a pivot that takes a while. And I think the example you provide of taking the business private again and having a longer term investor or leader that can operate with the mission over the duration is so critical. Your points around the news media and the environment we're in are so poignant today. Thank you for sharing those. I think most people don't never really thought about the recipe that goes into making a story and how, like you said, sources are interrogated and why sometimes anonymous sources are used to protect the identity of those people that are sharing sensitive information. And what's interesting to me is that the recipe for how an algorithm works is far more complicated and even more obtuse.

(22:23):

And so people are ingesting large amounts of information now from a much more, I'd say, alien form of a recipe for it. And so it'll be interesting to see how over the long term, we're able to maybe shine light on how those things operate. It's not just it's technological bias plus human bias. And in a lot of ways, we're sort of just learning the consequences of using these types of systems today. And the way old form books were written and made, it took a long time to write up a whole book. And today with the augmentation of content through ai, we're going to have a proliferation of content. I'm not sure that's going to make for a proliferation of truth or veracity. It will not at all. So it's going to be very, very difficult to figure it all out. All right. So I had a couple more questions for you, and I know your time is precious. We help a lot of early stage entrepreneurs that would look up to someone like you and they know that entrepreneurship can feel really scary or intimidating. What advice would you give to a bunch of young women out there or girls that are sort of not sure where to get started or how to think about the stress that might come with taking that first step and what would you tell them?

Katharine Weymouth (23:34):

Yeah, great question. I think about this a lot. And I have worked with many female entrepreneurs. I think part of the challenge is the way women are socialized. We're socialized as pleasers, and I see a lot of, and I don't want to overgeneralize, but a lot of male entrepreneurs who are just like, they just totally believe in themselves and their idea and they're like, yeah, I can do this. And women, they often say women don't start a business until they know it can work. So sometimes you do just have to have an idea believe in it, and just put one foot in front of the other. And I do think, I don't love reading business books, but I love reading or listening to podcasts of successful businesses and entrepreneurs. Like right now I'm listening to, and it's an old book Shoe Dog by Phil Knight.

Nic Cary (24:29):

Oh, that was so good.

Katharine Weymouth (24:30):

Nike. It's so

(24:32):

Good. And that is a great, that's a perfect example. He had this crazy idea, right, of importing sneakers from Japan for runners. His father was like, stop jacking around, like go get a real job at Pricewaterhouse or whatever. And he just had this passion for it, and he wanted to do something that he loved and he had no money and borrowed a little from his dad and then got some shoes and then started selling them at the track. And so I do think you have to believe in your idea because there's going to be a lot of bumps on the road. There's going to be a lot of people who are going to tell you you can't do it. And you have to be able to navigate those bumps when somebody tells you no, or you run out of money or whatever, and then just keep putting one in front of the other.

(25:23):

Ask your friends to help or get some mentors or whatever. And sometimes you also do have to, and he keeps saying this in the book, and Mark Zuckerberg says it a lot too, fail fast, right? 90 something percent of new businesses do end up failing. So you have to, I guess, know when the signs are, you know what? You don't have, you had this great idea, but there's no demand for it. No customer wants that product. But I also think his book and many others like the story of the Walmart founding, I was just listening to, I think it's acquired to podcast to the whole thing on the Walmart founding. And it's another totally scrappy story, I think. And Sam Walmart talks about it. Phil Knight talks about it. I think it's actually better not to get big VC money because you can get a little sloppy with that hire. Too many people get a fancy office. There's something good about having to be scrappy and having to figure out how to do something before you can buy the really nice point of sale system or whatever and learn before you can invest that kind of money. But it is definitely not easy starting a business.

Nic Cary (26:33):

Well, thank you so much for sharing all these pearls, wisdom them. I've got a bunch of things here I'd like to sort of summarize. So from the early days, I think taking what you can around you and then learning as much as possible, taking some risks, believing in yourself, I think was something that came through really strongly. You talked about the importance of forging relationships authentically. I think this is really key. If you're going to find mentors or coaches or advisors, develop those in a natural way and find people you admire that are role models for you, that was really amazing. I loved your point around getting close to revenue, especially if you're early on in your career, if you have opportunities to find the revenue center of your company, and sometimes that means getting out of your comfort zone. I know a lot of people go, like you said, I don't want to impede your sales.

(27:19):

That sounds icky. I'm like, sales is maybe arguably the most important aspect of almost everything the organization does. It's like 50 50 sales and product or service. And so getting close to that, understanding the dynamics of it, listening to customers and getting good at understanding their problems so that you can help them is so, so critical to company success. So that was really, really good though. Do uncomfortable things. Put yourself out of your comfort zone, and then your summary was really, really poignant. So believe in your idea. Sometimes you have to ignore some of the naysayers, find people around you to be supportive, recruit help. And if you're going to make mistakes, fail fast and figure out by listening to your customers, who are your best teachers? What's working and validate your idea or demand? So thank you. That was an amazing story to hear from you across your entire career. Thank you so much for sharing that with us today. So in conclusion, thank you again. At Skysthelimit.org, we connect underestimated entrepreneurs with volunteer business professionals for free one-on-one mentoring. We also provide business guides to all our members and monthly funding opportunities. So if you liked what you heard today, please subscribe or share this podcast. We'd be very grateful. Thanks again.

Katharine Weymouth (28:31):

Thank you.

OUTRO (28:36):

Thanks for listening to the First Buck podcast. Don't forget to join the community of underrepresented entrepreneurs and their supporters by signing up at skysthelimit.org. Click subscribe and we'll see you next time.