The Twin Room Episode 3: We Can All Do Hard Things

In this conversational episode, Winnie Hart and co‑host Speaker B discuss the challenges of entrepreneurship, especially the loneliness founders often feel, and how the Entrepreneurs' Organization (EO) and its Global Leadership Conference (GLC) provide a peer network that mitigates that isolation. Winnie recounts her long‑term involvement with EO since 2005, describing how the Forum experience reshaped her view of business and life. They highlight EO’s role during crises—Katrina and COVID—showcasing how the network supplied shelter, equipment, and emotional support. The dialogue shifts to current technological disruption, focusing on AI, the Global AI Summit, and digital twins, and how these trends inform strategic planning for leaders. Winnie emphasizes the importance of building strategy before adopting tools, warning against “deepreels” (mis‑used AI content) and noting that her recently published book is already outdated due to rapid tech change. Throughout, the tone remains informal, peer‑to‑peer, and optimistic, underscoring the value of shared experiences, vulnerability, and continuous learning for entrepreneurial leaders.
Chapters
Sometimes I really think about entrepreneurship and I think about how lonely it can be. Running company, you know, leading organizations, all the changes that have been happening in the world and like not having someone to go to and say like, what is going on?
Well, I know you're part of a big organization, EO. You just got back from GLC. What was that all about?
Oh my God, it's so great. EO. I could talk about EO for hours. I know it's not our topic, but I could certainly talk about it.
Yeah.
You know, I've been in so many organizations in my life and I've been in EO since 2005. 2005. I can't even— I don't know how many years that is. A bunch of years. And I think in the beginning I thought that— and this is before you came into the company— and I thought that like I needed like a board of directors or something, and I thought that's what it was about. But once I joined— it took me a long time to join— once I joined and understood what Forum was and the impact that it could have not only on my business but in my life. I mean, it completely changed the way I— not only how I see business, but like how I see the world. And you asked about GLC. GLC is— and I know you've gone to a couple of those— Global Leadership Conference. It's where all of the leaders in the organization come together once a year to learn and grow, to learn about their new role being board, being on the board in their individual chapters or being a leader in their regions or even at a global level.
And it's where—
someone mentioned to me once before that GLC is where we all begin to sing the same song.
Mm-hmm.
You know, and just how to all feel like that we're together, that we have this massive peer network, people we can rely on and trust. And, you know, back to my initial statement is It's a time where we need those peers.
I remember being with you, not at this one, but I think it was last year's, and the chairman at the time talked about that we can all do hard things.
We can do, I was keeni.
That was so inspiring. And, you know, from the times that I've been able to participate, just the vulnerability of the people there And being able to share what they've learned as a leader in a place where it was their audience. They were there with their audience, with their peers.
Their people.
Yeah, their people. And I was really inspired by that.
That was a great GLC.
Mm-hmm.
Yeah, it was a really good one for me. This GLC, I was able to be the learning lead. So I was able to work with the staff who are on unbelievable and incredible to really procure a really great collection of speakers that people want to hear. And it just felt really good to offer so much inspiration and knowledge and connection between people. This is, I think this was a first ever sold out GLC to 2,200 people.
Well, and it's for GLC, it's not in the entire organization, it's just the leaders of the of the different chapters, is that what it is?
Yeah, well, we have almost 20,000 members all over the world. Every single corner of the planet we have members that are entrepreneurs that are looking for ways to be less lonely and to learn. It sounds kind of drab, but I mean, it kind of is one of those core entrepreneurial feelings sometimes, at least for me. But I feel like that we have this network that we can lean on when, you know, Right now, I mean, talk about disruption. There's so much opportunity out there. And with AI and with all the things that are happening around the world. And on the other side, the geopolitical climates and tariffs. And, you know, there's a lot to take in and absorb. And like, how do we continue to build companies and prosper and support the communities that we serve?
Well, I think it goes back to really thinking outside the box. And I can appreciate that, you being kind of the visionary in our organization, whereas I'm more of the integrator. Whereas you come in with these amazing ideas. You come back from these events and it's like, "I got a great idea." And it's just exciting, exciting to hear what's happening in the world, not just your community. Well, where would you see that?
I mean, we have access to so much content now and news and, you know, touch on what's happening around the planet, but it's different when you're in a room with people from around the world and having real real conversations or even in the elevator or, you know, over a cup of coffee, like what people are really concerned about, what they're excited about, the things they're working on. It's so exciting. It is again, you know, as I thought in the beginning that EO would help my business, you know, to help me grow our business, but really what it helped was it helped me be a better human. Like it helped me be a better wife, a better friend, a better mother. And I'm so incredibly grateful for the opportunity that it's given me.
And I also think in terms of challenges, you know, that every business has, you know, a lot of times people think that leaders have all the answers, but they really don't. No. And they're learning just like everyone else. And just the challenges we've had over the years, I think, you know, a reflection of EO, remember you said when it was Katrina, it was 20 years, many, many years ago. And I remember you said you had gone to an EO event and you said that the one thing this guy— was it Bill Bourne?
Brandon? Or was it Bill Bourne? Bill Bourne was the— from Crisis Comes Opportunity.
From Crisis Comes Opportunity. And we took that and ran with it.
Yeah.
And then, you know, we did it again during COVID It was one of our best years. Best years ever. But really, you know, knowing that there's people out there that can, you have a network of people that you can reach out to when you need it. I mean, we, after Katrina, we had nowhere to go and I think that was an EO, one of your EO partners in Baton Rouge that gave us a place to stay.
Yeah, hired some of our employees.
It was incredible.
Sent us equipment. You know, I always feel like we're kind of one step away from some major disaster. I don't know if anyone else feels that way. Knowing that there's a support group there that will drop everything and do anything for you anytime is very— I mean, I can't even put a value on that.
So if a leader came up to you and said, why would EO be good for me? Why should I join an organization like that? What would you say?
Why not?
I mean, I— Well, there's so many organizations out there.
Well, there is. And there's so many competing ones. I would, you know, I think EO has been a very difficult experience to put into words. You know, EO is a feeling, you know, it's an experience, but it is a network of peers that support you to help you find your potential, help you grow in great times and in challenging times. And having a world sense of things is critical today because like we have to be, even if we're running a business in a small localized business in a city or we're running a regional business in a country or a global organization in the world, we have to understand what's happening in the world. And this is a way where you have a real, a real touch on and a real sense of what's happening, not only in the world, but in people's businesses, like inside the businesses, where the opportunities are. Right now, there's a program called the Global AI Summit, which is an Aneo initiative. I had the opportunity to speak there. Was it last year? Last year? Yeah.
Earlier this year.
Was it earlier this year? To talk about digital twins. And it was such an honor to go and do that and to have that opportunity. But what I learned from it was like from all the leading people in AI about what's really happening, who to reach out to, what tools are people using, like fast learning. And I don't know how to put it again, a value on that either, because like it helped, it's helped us like build our AI strategy to really support our clients and bringing them up to speed on what's happening and how AI can support them. But also just knowing that this is going to change and evolve so fast that you've got this big network that is there to support you. I mean, unlimited. You know, we saw Brené Brown last week who was phenomenal. Christina Harbridge interviewed her. Oh, wow. I need to share that video recording with you because she was just amazing. And she— I think her new book is called Strong Ground. And it's about like the things that keep you steady in all of these volatile times. But, and having Kristiana Harbridge interview her was just like, just one of those, like, this is a once in a lifetime moment right now, right here on Zoom, watching her. And I mean, it happens weekly, weekly.
It's incredible.
I know.
The, you know, I've had the opportunity to participate in some of those things too. And, you know, the one thing that that really resonated with me was sharing, sharing experiences rather than—
Well, you're in Executive Forum, aren't you?
I'm in Executive Forum. Yeah, Executive Forum. Yeah, I've been, I think, for 5, 6 years, something like that. And I really get a lot out of it because, you know, to your point, you're talking to people that are dealing with the same things you're doing, and you can really be vulnerable with them and really talk about that, that 5% of things that you really wouldn't share outside of your, you know, outside of the team. You know, might be the struggle that you're having in the business or something operational. And they've all been through it.
Yeah.
And so you just share different experiences and it really makes a big difference. Yeah.
Where you don't offer advice. Right. It's more experience.
Share experience.
So you always feel safe and not sold to.
Yeah. And not judged.
And not judged. That's huge.
Huge. It's a great organization.
I know. I love it. I can't wait till next year. I'll see— I think it's in Japan. Nice. It's going to be fabulous.
So you mentioned earlier about the digital twin. Don't you have something coming up for that? Is that through EO?
That is through the AI Global Summit.
Okay.
That is in June, June 3rd. It's part of their— they have a monthly, I think it's first Wednesday of every month, speaker series. I know that I'm June 3rd, but the content is terrific. And there's so many EOs out there putting out amazing content. But I love this group because they're really looking to like— it's almost like a mission for them to provide the most up-to-date technologies for EOs so that they can just thrive in this environment. Because this is where, like, ERs thrive. It's like, it's crazy. We don't know what's going to happen. We don't know what the future looks like. But that's our space. You know, let's go.
It goes back to that being a visionary. Being a visionary.
Yeah. I know that's painful for you sometimes.
It is sometimes. Winnie, what are we doing now?
I know. Did you see the video I sent you this morning about that?
I didn't. I haven't seen it yet. What is her name?
Of course, it's one of those, I think one of those college speeches on a few— it's graduation time right now, so you're seeing all these college speeches. And they're talking about the key question in life that these leaders are being asked of, and it is, "What are we doing now?" And, you know, emphasize on the now because, you know, if you're doing business the way you always did business, there's something very wrong with you. Those sentiments and those foundational aspects should be the same, but things have changed so much, and there's so much more opportunity, but there's a lot of challenge that comes along with it too. In being able to change fast and agile and to take advantage of things. And knowing what's real and what's not. When to make decisions. I find it very exciting.
Very exciting. I think we're definitely at a tipping point.
I don't know if it's a tipping point or like, I don't know what the metaphor analogy is. It feels very much like, you know, What happened months ago with Claude in particular really changed the way I thought about the rate of change because I was like, oh, we got a couple years, this is gonna be great, we have plenty of time. And then I think it was like November, October, November when Claude made that big shift. I was like, whoa, okay, here we go. Not knowing when, 'cause you spend time learning all these different aspects, but then you're like, well, do I know everything? And then a week later everything changes. Or the next day. Or the next minute. But you have to get comfortable with it.
Well, what I'm excited about is that we did— we immediately— I mean, this was over 2 years ago. 2 years ago we started utilizing AI. And to me, it's fun because you're learning new things and new ways of doing it. But I think you really got to be using it on a daily basis to really understand what it is and how to use it.
And learn from others too.
I'm excited about the class.
Me too. I'm excited about too. I mean, digital twin, build it before it builds you.
Yeah. No.
You know, one thing, I just published the book a couple months ago. It's already out of date. So I'm always, I'm still in a space where I know what I'm going to talk about, but I keep thinking about what tools am I going to show because the tool we're ultimately going to use probably hasn't even been considered yet. And so, you know, I don't want to spend too much time talking about the tools and more about like strategy that you need to build and put in place as a, as a leader, because you want to be at least aware of what's happening and the opportunities that exist for you and not be caught off guard with some— I don't call them deepfakes, I call them deepreels. You know, we've obviously dealt with some of those in our business and some are pretty easily handled, but some might not be in the future.
What I'm seeing is a lot of people just rushing out there to use a tool and not really thinking about What is my strategy?
What is the purpose of this?
How am I going to use this to help me be more efficient? Whatever your goals are, and really building out that strategy, then go to the tool, rather than the opposite. So I think we've seen a lot of rogue things happening out there with these different tools.
And again, I just see them as tools.
As long as you use them in a the most strategic way. Mm-hmm. I agree.
So exciting.
Mm-hmm.
Let's go.
Let's go. I'm ready. See you next time.
Bye.










