This software will make you fall in love with your job again

We're back with another entrepreneur from our community! Brian Robertson, who is making the world a freer and more prosperous place through the organizations he's created, agreed to chat with our marketing manager, Laura Ferraz, about his entrepreneurial journey, sharing insights on how his businesses help advance capitalism, and especially about GlassFrog, his company that is currently raising capital and aims to transform every organization into a sanctuary of clarity, passion, and purpose. 

Curious to find out how Brian helps people fall in love with their jobs again? Read this interview to the end!

Laura: Brian, thank you for joining us today. It's fantastic to have you share insights into your journey with GlassFrog and Holacracy. Congratulations on your success and welcome to our community dialogue.

Brian: Thanks for taking some time to help us become known in the community.

Laura: My pleasure! So, what's your story with entrepreneurship? How did it start?

Brian: I've been an entrepreneur for a very long time. I started trying to build little businesses as a kid. I had a newsletter with old video game maps and solutions that I sold when I was around seven or eight. I started pretty young. My first more significant business was when I was 13. I was teaching people coding online, pre-internet, on early online networks. No one knew how old I was. Basically, I learned to read on software development manuals. And so I was teaching people for like 25 bucks an hour, which I thought was a fortune when I was 13. 

Laura: Better than me. I used to charge the equivalent of 3 dollars for doing my classmates’ homework (both laugh).

Brian: Oh, really? Mine was 25 bucks an hour teaching people to code on early online networks. That was my first business. Eventually, the network said “Hey, well, this is attracting subscribers”, so they just hired me instead of paying me a fixed amount every month to teach online for so many hours a week. They had no idea how old I was either. But my first adult business was when I was 20. I started my software company, which is what led to Holacracy and I basically started that company as a laboratory for finding new ways to work together. And that's ever since I've started many companies, but I got a pretty young start.

Laura: At seven, you were almost a young Sheldon. That's interesting.

Brian: I have a daughter I'm raising now, and I'd love to get her started young with these entrepreneurial projects. There's so much learning and development that comes from trying to create something in the world and then share it.

Laura: And with GlassFrog, your other child, what's your personal purpose with it?

Brian: There's my own personal purpose, of course, separate from the company's purpose. I do a lot of work with purpose discovery, so I've articulated my own purpose. GlassFrog is about changing the workplace. We use a rich purpose methodology, much more so than most. It's based on Tim Kelley's method from his book "True Purpose."

GlassFrog provides the spark of insight that ignites evolution, often by offering radical transparency into organizations. This transparency can evolve processes, structures, and policies to improve how things work. Our mission is to transform every organization into a sanctuary of clarity, passion, and purpose. So many companies crush their employees' entrepreneurial spirit and disconnect them from purpose. GlassFrog's software tool offers unprecedented clarity, breaking down purpose so everyone can see how their roles and projects align with it and evolve the organization to serve that purpose.

Laura: This is interesting because with the work-from-home working style, some people may lose this sense of purpose and eventually the ownership of what they are responsible for doing.

Brian: I love what GlassFrog adds to this. It's in that category of tools, but what I found is that everyone in an organization, the one skill that it seems everybody has anywhere, is they're good at complaining, even the most disempowered worker is at least good at complaining. And we're using AI in this really cool way that lets you just complain and it turns your complaint into an empowered proposal that you can then push to your team. It knows your structure, your policies and your processes, so you can literally go in and dump a complaint on the AI. And it can say, “Oh, well, how about you propose changing this policy adding this expectation here and this process step there? Would that solve your complaint?”

So it's basically giving everyone a way to turn complaints into proposals. There are obstacles. And when you can turn the ability to just complain about them into helping people see how they can find the power to move forward to clear the path to the purpose, that's pretty game-changing. I'm excited about what we're doing.

Laura: I love your enthusiasm and the features GlassFrog provides! About the software itself, do you use ChatGPT or other AI for your software? What do you use as the backend?

Brian: So, we're using Chat GPT on the backend, but it's not just a wrapper for ChatGPT, which is a lot of things that they're basically wrapping the interface or sending queries directly. Bute've done a lot of training on top of ChatGPT. So there's a pretty massive amount of data behind the scenes of basically a combination of Prop crafting, and then custom data we're adding into it so it's a lot more than just a basic ChatGPT run. It's basically a ChatGPT custom trained for this purpose.

Laura: Do you think you’re using GlassFrog to advance Capitalism? If yes, how?

Brian: Yeah! That's the system we're in. People that appreciate the power of free markets tend to appreciate what GlassFrog brings even more because what it's doing is bringing the kind of autonomy that you see in a free market into a company.

Today, companies often look more like a feudal empire, even the ones led by leaders who get the power of free-market capitalism. They look more like a top-down plan of the economy, which is not the best way to organize in the face of high complexity. It works great when complexity is low, but in most companies nowadays, in the environments we're in, complexity is not low, it's high. And in those environments, we need something that relies less on planned order, and more on emergent order, like free markets do.

Laura: And what is your biggest dream for GlassFrog?

Brian: It's literally to turn every organization into a sanctuary of clarity, passion, and purpose. I have so many friends whose organizational life is not the source of their greatest joy. And this is less true of my founder friends, founders tend to have it, reasonably good until they get completely overwhelmed and overloaded as the company grows. But I want everyone right down to the frontline to experience the thing that otherwise it really stops at the top. I want them to experience true leadership, self-leadership, leadership, of their area, real autonomy, real empowerment, not the kind that you have to ask a boss for, because that's not real empowerment. The kind where the environment itself supports people just leading their peace. I think there's lessons in that. I want to see a world where instead of looking to the politicians to solve our problems, which is another form of deferring authority, it's not different from looking to managers to solve our problems, deferring power up the hierarchy.

Laura: And with this quality of self-leadership that I’m sure you require from your partners, was it difficult finding people to help you build this up?

Brian: No, there's a lot of people that get this problem set and want to contribute towards it and see the potential of this. We've got a really amazing team working on it.

Laura: Brian, how the Liberty Ventures Community can help you build this build-up in case anyone who is reading this article wants to get involved?

Brian: Just try GlassFrog. There's a free version of the products, but obviously we also offer the premium paid version.

I want to see more people empowering their workforce in deep ways, and ending the reliance on a lot of top-down controls and a lot of meetings because both of those are things we can do better.

And the second, I'm always open to good connections of any sorts. We're in a capital raise now, so we’re always looking for good angel investors that get our kind of thing and for people that can just help us connect into clients that can really use the kind of organizational clarity that we provide.

Laura: I’m glad that you mentioned being open to good connections because we are having a Principal Business Summit in New York this September. I’ll use this opportunity to invite you and the person reading this article to join us there. This is a good example of an event that could help you attract more investors and make more connections.

Brian: Love it! Send me more details.

Laura: And returning to the questions, what has been the most surprising to you on this entrepreneurial journey?

Brian: That's an interesting one. All my capacity to build a good company and to lead well are so interwoven with inner work. The more I do my own personal development work, the more effective my companies are. The biggest transformations in my companies come right after my biggest inner transformations. Consistently, everything for me comes back so much to the self-work of especially to founder or key leaders in a company. nit's almost to the point where whatever major business problems I'm facing, I will be just as likely to figure out how to transcend them by going and doing inner work on my own things. As I will be strategizing about my business. The link is so much stronger than I realized when I was early in this journey.

Brian Robertson alongside his HolacracyOne co-founder Tom Thomison in 2007. Since then, they have been developing and sharing the self-management framework known as Holacracy, that evolved to GlassFrog.

Laura: Sounds like a but challenge. By the way, speaking of challenges, what challenges have you experienced so far, and how did you overcome them?

Brian: Well, it's been several times over by now, a multi-decade entrepreneurial career where I just get really stuck in some way in my business. And the answer is almost to figure out how I'm stuck in some way in myself. Once that is transmuted in some way, once I've transcended that issue or integrated something new, usually, the business thing takes care of itself. Although at times it's been in the past by me leaving, it's one of the hardest things I've learned to do as a founder is when to leave, which I've done now, two times from businesses that I built for years into things.

I have now had to exit and leave those, and not simply exit. We're at the natural point where we exit and sell but realize that “no, this thing is still growing. It's on a great path. And I'm the wrong guy to continue it on at this point." And the best thing I can do is get out of the way and bring somebody else in which I've figured out how to do and, I can still have a relationship with the companies on the other side. I can still hold equity on the other side, or I can sell them but the single biggest mistake I've made is staying in too long. And I think I've finally figured that one out, but we'll see.

Laura: When you first started these other companies, what was the motivation?

Brian: I've never created any company just for the intent to build, grow, and sell. I've created them because I wanted the thing they create to exist in the world and I created more as a passion for every one of the companies I've started. I've assumed I would just be at it for decades. So it's quite difficult to then reframe it and realize “Oh, I've actually done my work here. The thing I wanted to create does exist and I'm no longer the right person to grow it and build it. So now I need to choose to either sell it or exit and have somebody else come in and grow it or whatever.” That's a hard thing to realize when I started thinking I would be there for decades because they were never created just to generate wealth. They did do that, but they weren't created for that purpose. They were created for creativity to create something in the world that's beautiful and that needs to exist.

Laura: It was an exciting conversation. Thank you for what your doing with GlassFrog! As I said, not only do we need to be accountable for what we are doing, but seek ways to improve our processes.

Brian: Thanks for having me. I appreciate the opportunity.

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