886 Caroline Dell: Co-Founder of Goodword

0:00Kara Goldin:I am unwilling to give up, but I will start over from scratch as many times as it takes to get where I want to be. You just want to make sure you will get knocked down, but just make sure you don't get knocked out. So your only choice should be, go focus on what you can control. Hi everyone and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world's greatest leaders. We'll talk with founders, entrepreneurs, CEOs, and really some of the most interesting people of our time. Can't wait to get started. Let's go. This episode of the Kara Golden Show is brought to you by LinkedIn Hiring Pro.

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2:19Kara Goldin:Get started by posting your job for free at linkedin.com slash Kara Golden. Terms and conditions apply. Hi, everyone, and welcome back to the Kara Golden Show. Some of the biggest opportunities in business don't come from what you know. They come from who you've invested in over time. Today's guest is Caroline Dell, co-founder and CEO of an incredible company called GoodWord, an AI-powered platform helping founders and operators turn their relationships into one of their greatest competitive advantages. Before launching GoodWord, Caroline helped build an incredible company as well called Chief, from 200 members to over 20 ,000 members and more than 100 million, 120 million in ARR, playing a key role in scaling that company to become one of the fastest growing female-founded companies in the country.

3:15Kara Goldin:Today, we're going to talk about her startup that she launched, Good Word, that she co-founded, I should mention. And I cannot wait to talk about the power of relationships and what it really takes to build high-performing teams and being a great operator as she is and a great founder. So Caroline Dell, welcome to the Kara Golden Show. So excited to have you here. Thank you, Kara. I'm super excited to be here. Very, very excited. So for listeners just hearing about GoodWord for the first time, what is it and what made you believe that this company needed to be built? Absolutely. GoodWord is a relationship management platform that helps you unlock the power of your network.

4:05And I believe that every great opportunity really comes from the people you know. In my experience, every job offer, every check that was written into the business, every opportunity, every door that was opened was opened by another person putting in a good word, saying my name when I wasn't in the room. And those opportunities, especially in the world we're living in today, where we're spending most of our time as professionals, heads down, chatting with a robot, those are becoming more and more and more important to professionals to really succeed. It's the trust and the social capital that comes from your network.

4:50So like you mentioned, I was a really early employee of chief, a founding employee chief. and I saw over and over the power of the right person at the right time. So for example, one member, I still remember the day she came into the Tribeca clubhouse and she was like, oh my God, I got my dream job and I literally never would have applied. I just wouldn't have applied. I didn't think I was qualified. Call it a pastor syndrome, call it whatever you want. I wouldn't have done it. But a member of her coaching group said, hey, I know the hiring manager. I know someone at this company who could get you an interview.

5:32Let me put in a good word for you. So she did. She passed along her application. She got an interview. That interview led to the dream job. And it was just that right person at the right time that unlocked a door that she wasn't even going to knock on. That's how intimidating that door was for her. And I saw that over and over, really. A lot of chief members wanted their first board opportunity. Board seats often are not posted publicly. There's something that kind of get passed around through a whisper network. You know someone who's an executive there. You know one of the investors of the business.

6:08That's how board positions typically get filled. And so it was really seeing it up close and personal achieve the power, again, of the right person at the right time, that made me say, what if we had a platform that actually allowed professionals to take everyone that they've met over their career, whether that's from university or communities they're part of, or all the companies they've worked at, their former colleagues, and pulled it together, and then allowed them to search it, use it, and really activate all that goodwill, all that social capital in the moment that you need it.

6:49Kara Goldin:This episode of The Kara Golden Show is sponsored by Wayfair. As the seasons change, I always start noticing the little things at home that I've been meaning to fix or refresh. For me, one of those was my home office. I wanted it to feel more finished and functional and a beautiful gray weathered wood bookcase from Wayfair ended up completely changing the room. It gave me the storage I needed, but it also made the space feel warmer and more pulled together. That's what I like about Wayfair. They make it easier to create a home that actually works for real life with quality products, great value, and so many options across every style and budget.

7:28Kara Goldin:I also like shopping Wayfair verified products, which are hand vetted by product specialists using a 10-point quality inspection. That gives me a lot more confidence when I'm deciding what to bring into my home. And when you're refreshing a space, the reviews really matter. Wayfair has more than 20 million verified five-star reviews, plus customer photos and filters that help you narrow things down and find the right fit. And if you're a Wayfair Rewards member, you get 5 % back on every purchase. For me, Wayfair made solving that home office problem simple, and I'd absolutely recommend it if you're furnishing a space, refreshing a home for fall, or just finally tackling something in your home that's been on your list for too long.

8:14Kara Goldin:Transform your space with pieces that hold up to real life. Join Wayfair Rewards today and get 5 % back on every purchase. Head to Wayfair.com or shop the Wayfair app for all things home. That's W-A-Y-F-A-I-R dot com. Wayfair. Every style, every home. Wayfair. Every style, every home. This message is a paid partnership with AT &T Business. Hey, everyone. Kara here. Let's get real about those early days of building a business. Not the highlight reel. The actual day-to-day, the friction, trying to manage everything across time zones, across teams, across locations, and realizing how much depends on staying connected.

9:01Kara Goldin:I remember those days at Hint, a retailer call, an order, a decision, all of it. And you realize quickly, connection isn't a nice to have, it's the lifeblood of your business. As a founder, you don't want to think about your connectivity, you just need it to work every time. That's why AT &T Business Matters. AT &T Business is the reliable provider for small business owners. And when you have that kind of reliability behind you, you can focus on what actually moves your business forward. Powered by AT &T Business, built to work. Get AT &T Business at business.att.com. Support for today's episode comes from Perplexity Computer.

9:51Kara Goldin:If you're running a business, you know the drill. Your day can start with five different dashboards, a couple of spreadsheets, and way too much time just trying to figure out what's actually going on. That's why I've been so impressed with Perplexity Computer. Perplexity Computer can connect to the tools you're already using and bring everything together. revenue, ad spend, inventory, margins, email performance, and actually flag what changed and where you should be paying attention. But what I really love is that it doesn't stop at giving you information. It can actually get to work. It can help build your next ad campaign, rewrite a Klaviyo flow, draft creator outreach, even help build your CRM.

10:42Kara Goldin:You give it a project, not just a question. And here's the really interesting part. You're not locked into one AI model. Perplexity Computer works across the leading AI models and chooses the right one for each part of the job. For a limited time, you can try Perplexity Computer for free. Head to pplx.ai slash Kara Golden. That's pplx.ai slash Kara Golden to try Perplexity Computer today. Most AI tools are still answering questions. Perplexity Computer is getting the work done. I love this so much. So when you were helping to build Chief, you saw the company from a very small, a couple hundred members to 20 ,000, what would you say was the magic there?

11:40Kara Goldin:Because I think scaling a company from that kind of, you know, that's a big range, right? So you were there early and saw the hockey sticks, so to speak. So I'm excited to see what you're going to do with Good word, but what do you think it would, if you had to sum it up for founders, what do you think is the key there that you know needs to exist besides having the relationships? But there's more to it too that you can, just because you have relationships doesn't mean that you can build and do what you all did at Chief. Yeah, absolutely. I think that Chief hit on a fundamental human truth, which is that we all crave connection.

12:27We all crave community. And interestingly, Chief started in 2019 with a single clubhouse in person and a couple hundred members. And one year into the business, the pandemic, the COVID-19 pandemic hit. And frankly, a lot of our investors were like, well, that company is going to go out of business. It's an in-person physical experience and the world is on lockdown. And, you know, what we did instead is we moved the whole experience online at a moment where community and connection mattered more than ever, right? We were home, we were isolated, we didn't have that human connection and we were craving it.

13:13And that actually allowed, you know, two things. One, I think we hit on a a fundamental human need that was so pervasive of a feeling in that moment. And two, it actually unlocked growth because it removed the barriers of real estate and the physical constraints. So I think it's maybe the generalization or lesson for founders is one, is it a real need? Is it a true need and it is a visceral need that your customer feels? And then what are the constraints to growth? And are there ways to sort of unblock those? And sometimes it's macro, right? This is a macro factor that kind of worked in chief's favor.

13:58But are there controllable factors that you can unlock, that you can address to unlock growth? So for Goodward, we took some of that insight of we are all looking for that human connection. There's been a lot of studies over the intervening years about how loneliness is one of the biggest epidemics of our time, how it can have physical impacts that are worse than smoking cigarettes, and really saying, well, how could we help facilitate human connection and opportunities with technology? Instead of putting technology in the center of a human relationship, right, not outsourcing our relationships to agents, but using AI to actually say, let's empower the human to have more connections, deeper connections, more memory than we could do alone as humans because our brains are limited by how much memory we have in our brains.

15:03which unfortunately, if you've ever read about Dunbar's number, it's about 150 people that we can remember with any real detail. Show up at any wedding, it's about 150 people. It's like the magic number. And we envision a world where instead of 150 people, what if you could actually remember 3 ,000 people, 10 ,000 people? What if you could show up for them with your expertise, your network intros and actually, you know, those personal details too. They live in San Francisco. They have a parent named Tiki. Their children are, you know, their daughter's about to go to college. Those things that actually are the fabric of a relationship.

15:45Kara Goldin:This episode of the Kara Golden Show is sponsored by Wayfair. As the seasons change, I always start noticing the little things at home that I've been meaning to fix or refresh. For me, one of those was my home office. I wanted it to feel more finished and functional, and a beautiful gray weathered wood bookcase from Wayfair ended up completely changing the room. It gave me the storage I needed, but it also made the space feel warmer and more pulled together. That's what I like about Wayfair. They make it easier to create a home that actually works for real life with quality products, great value, and so many options across every style and budget.

16:24Kara Goldin:I also like shopping Wayfair verified products, which are hand vetted by product specialists using a 10 point quality inspection. That gives me a lot more confidence when I'm deciding what to bring into my home. And when you're refreshing a space, the reviews really matter. Wayfair has more than 20 million verified five star reviews, plus customer photos and filters that help you narrow things down and find the right fit. And if you're a Wayfair Rewards member, you get 5 % back on every purchase. For me, Wayfair made solving that home office problem simple. And I'd absolutely recommend it if you're furnishing a space, refreshing a home for fall, or just finally tackling something in your home that's been on your list for too long.

17:10Kara Goldin:Transform your space with pieces that hold up to real life. Join Wayfair Rewards today and get 5 % back on every purchase. Head to Wayfair.com or shop the Wayfair app for all things home. That's W-A-Y-F-A-I-R.com. Wayfair. Every style, every home. Wayfair. Every style, every home. Yeah, definitely. I love that you mentioned that. So every founder has that moment where they stop building someone else's vision and decide it's time to build their own. What was that moment that you said, it's time, I need to go and do this? It was actually a gut punch moment. I was serving as the GM of a new vertical at Chief.

17:59And we were trying to build and launch something new. I was super excited. It was almost like I was a founder within the business. And for a number of reasons, we decided that that initiative wouldn't be launched on the original timeline. we had been aiming for. And so we went from conversations with the board that were like, how fast can you launch this, Caroline, to I think we need to postpone it indefinitely to put the business resources in other places. And this then CEO of Chief came to me and she said, you always have a job here, but I don't think I have a job that's big enough for you anymore.

18:43and I remember I got off the Zoom and I turned around and we were still working from home and I looked at my husband and he said you look like a ghost and you know I sort of had gone white and I said I feel like I just saw a ghost it was almost like that it sort of flashed before my eyes and I realized that that you know that desire to build right to really build something from nothing that I had spent the last eight, 10 years of my life doing at Lola and then at Chief, that opportunity wasn't there. The business needed something different when you get to 100 million in ARR and we weren't going to launch a brand new initiative in that environment.

19:26So it was actually an invitation and it was a gift. In hindsight, I feel like I kind of got kicked out of the nest. And the founders of Chief said, you're ready. We think you can found your own thing. And actually both wrote me personal angel checks and said, go do it. You know, fly from the nest and we believe in you. And here's our money to prove it. So it was a great gift.

19:51Kara Goldin:I love that story. So how has that shaped, I guess, you know, real relationships that you're describing and, you know, definitely must have shaped you into the leader that you are today. What do you think you took away from that experience above and beyond the kind of operational mechanics of the how to build a company as you've been a part of? But leadership, I guess, is really the key thing that I'm hearing that they were able to be very honest with you about feedback and sort to what the company needed. And now you're now the CEO and running what you're doing. And I think that's, it must have had some impact on you so far.

20:38The leadership lesson I took from that was there is the, there are two parts of the equation. There are the company needs and there are the employees needs. And in a best case scenario, they match. And for as long as they match, the company should do everything they can to retain the employee and to make sure there's a great job for them that contributes to the mission of the business. But when there isn't a match anymore, whether that's, and it could be because the employee's interests change, you know, it could also be because the company had to pivot or adapt. And when that match isn't there, I learned it's okay to name it, for the employee to name it, for the company to name it, to be honest about it.

21:27It had actually happened to me once earlier in my career too at Lola. I had joined as a third employee. It was the founders and the head of marketing. And so when you're in that role, you're doing a little bit of everything. You're sort of this jack of all trades. And I love that. I loved a little bit of recruiting, a little bit of a finance manager, a little bit of product development. And as we grew, you know, we got to 10, 20, 30 people, the founders said, hey, Caroline, we're actually not going to have a full-time chief of staff role right now, which is effectively what you've been doing. So here's a couple of options.

22:08You could do this role, you could do that role, you could do this role, which option is most exciting to you? And I think that was my first time. I didn't have the name for it then. But now I love the phrase, give away your Legos, which is this idea of like, you know, don't hold so tight onto a title, a job, a responsibility. If you're willing to kind of, you know, put these Legos down, you get to actually go build something new and something different and probably something more exciting if you're willing to adapt your skill sets in whatever the direction the business is headed. And again, if the business is headed in a direction that you're not excited to contribute to anymore, that is okay.

22:51And I actually think the best leaders name that and then support their employee in finding a great opportunity elsewhere, whether that is at another business or, in my case, in actually pursuing her own dream.

23:06Kara Goldin:This episode of the Kara Golden Show is sponsored by Wayfair. As the seasons change, I always start noticing the little things at home that I've been meaning to fix or refresh. For me, one of those was my home office. I wanted it to feel more finished and functional, and a beautiful gray weathered wood bookcase from Wayfair ended up completely changing the room. It gave me the storage I needed, but it also made the space feel warmer and more pulled together. That's what I like about Wayfair. They make it easier to create a home that actually works for real life with quality products, great value, and so many options across every style and budget.

23:45Kara Goldin:I also like shopping Wayfair verified products, which are hand vetted by product specialists using a 10 point quality inspection. That gives me a lot more confidence when I'm deciding what to bring into my home. And when you're refreshing a space, the reviews really matter. Wayfair has more than 20 million verified five-star reviews, plus customer photos and filters that help you narrow things down and find the right fit. And if you're a Wayfair Rewards member, you get 5 % back on every purchase. For me, Wayfair made solving that home office problem simple, and I'd absolutely recommend it if you're furnishing a space, refreshing a home for fall, or just finally tackling something in your home that's been on your list for too long.

24:31Kara Goldin:Transform your space with pieces that hold up to real life. Join Wayfair Rewards today and get 5 % back on every purchase. Head to wayfair.com or shop the Wayfair app for all things home. That's W-A-Y-F-A-I-R.com. Wayfair, every style, every home.

24:55Kara Goldin:I love it. So getting back to good words. So one of my favorite stories that I read or I guess I listened to in an interview that you didn't post a job description for your first engineer that you hired. Can you talk a little bit more about that? Because I think that so often people are thinking, okay, I've got to go out to the job sites or LinkedIn or whatever. What did you do? That's right. I did not. I was, when I left Chief, I was spending a lot of time researching the concept and trying to understand the true pain point. Like, why was there not a networking product or, you know, relationship solution that professionals loved?

25:44And I was hearing a lot of, you know, I use LinkedIn, but it's turned into professional social media and I don't want to, I feel uncomfortable posting on the platform or it feels cringy or I text myself and then I forget that I lose the text or I put it in Apple notes or I, you know, I cover my wall and post-its was one of my favorite ones, but I don't, you know, I don't have a system. And so I was both exploring the pain point and then exploring, is the technology even there? Like, is this feasible? And this was two and a half years ago. This was before, you know, we had some of the capabilities of AI today.

26:26And so I knew, not recognizing my own strengths and lack of skill set, I said, I'm not technical enough to investigate the technical feasibility of the solution that I want to bring to the world. and so I started asking around I thought okay who are the engineers I know and then I just sort of asked around if if they had an interest in spending some time with me no one really did I couldn't pay anyone yet right I hadn't fundraised I hadn't even officially incorporated a business and then one day I got a text from the woman who was an engineering manager on my team at Chief and she said, hey, some of the contractors that were on our new verticals team left chief because, you know, the chief isn't working on that anymore.

27:17And this one person is about to get married and go on a honeymoon. But when he comes back from his honeymoon, he's going to have some time. Do you want me to reconnect you? And by the way, he was the best engineer on our team. And I said, absolutely. Like perfect, you know, perfect timing. Feels like serendipity. And it was in some ways serendipity, but it was also that I had just kept the woman's name is Lexus. I had kept people up to date of, hey, they knew I had left chief, but what was I working on? How far had I gotten? What did I need? Who was I looking to talk to? So I never posted a job description.

27:57didn't. But, you know, within days I was on the phone with Patrick and we had a plan to chat and to explore. And he joined me 10 hours a week. I took my very, very first friends and family check from my dad. And I said, I could pay you a hundred bucks an hour for 10 hours a week. That's all I've got. But I need a technical thought partner to explore whether this is possible. And he said, let's do it.

28:27Kara Goldin:That's awesome. I love that story. So if someone were to open up their contact list today, how would you tell them to figure out which relationships actually deserve the attention that maybe is necessary for someone to be able to, you know, really build the foundation as what you're talking about at GoodWorks? Yeah, that's the challenge. If you open up your contact list today, you're going to see a flat static list of just names and phone numbers. Maybe you've put in their address or a quick note how you met. But there isn't any way of sort of grouping, organizing, visualizing, and really activating them in a purposeful way.