I have known Keith Fields now for a few years and I can honestly say I have seen him go down rabbit holes if a software comes by him. It doesn’t matter whether he truly “gets it” at first or not. He is bound and determined to get to a level of usable understanding. Keith is also a part of The Sensational Six, a POD group in Chad Nicely’s Entourage Mastermind.
Please join us today as we discuss Nicely’s Letterman software: how it came to be in Keith’s life, his work and how through Letterman, Keith shows that automation isn’t about removing people. It’s about freeing them to do more of what matters most.
Carol: What first drew you into Chad Nicely’s Entourage, and what led you to start using Letterman?
Keith: I have followed Chad for several years. I have watched him on webinars; been on several workshops with him which almost always were hands on. You went right along with him in those workshops. The software systems that he made always intrigued me. They would always accomplish something, so when he talked about Entourage and that it was going to be something different than what he has done before, there was another challenge. Learning his process systems techniques. I was all for that.
Then he brought forward Letterman. I thought to myself, how can I use this to my advantage? Actually, I’ve always had a tech-minded approach, and I saw Letterman as a tool that could enhance my ability to get more technical with Chad’s software than with the automation. For me, it wasn’t just about publishing content. It was about using a platform to show my expertise while building systems that run smoothly in the background.
Carol: You mentioned being intrigued by Chad’s systems for years. Was there a particular moment when you realized, “This is different, this is the challenge I’ve been waiting for?”
Keith: Yes, when Chad started Entourage I thought it was another workshop that had been done before. I was wrong. It was so much more than what he had done before. For example, the “Boxes” he put together with T-shirts, coffee tumblers and workbooks and other things, and then there was a letter that was personalized that talked about the journey we were about to embark on and how the first box ( one each for a total of 24 workshops ahead) and that each would have a box sent to me. That was absolutely amazing because never have I seen anything like that before.
Carol: Those boxes are definitely a “trademark” of Chad’s for sure. Keith, as you’ve started putting Letterman into action, what’s been the most powerful or even surprising part of the experience for you?
Keith: What surprised me most was just how powerful Letterman really is — not only in what it does, but in how seamlessly it’s put together. It felt like I finally had a complete system for building and running newsletters instead of a pile of disconnected tools. The automation, structure, and technical precision behind the platform gave me the freedom to focus on creating real solutions while it handled the presentation and distribution in the background. It was a real challenge. It challenged me in the best way — pushing me to learn how every piece worked together and to appreciate the innovation that makes it all run so smoothly. Seeing the community rally around that same excitement made it even more rewarding.
Carol: I love how you called it a “real challenge.” Can you share a specific “aha” moment where you saw the automation and structure free you up to focus more on solutions?
Keith: Carol, my big ‘aha’ moment was realizing that once the automation was in place, I wasn’t stuck inside the weeds anymore. Instead of spending hours formatting, scheduling, or chasing details, Letterman’s structure handled that for me. That freed me to focus on what I do best — building solutions, spotting opportunities, and connecting the dots. The real challenge for me was letting go of the busywork, but once I saw the system run on its own, it clicked: this is how you multiply results without multiplying effort.
Carol: Everyone brings their own strengths to the table. What do you feel you’ve brought to Letterman that helped you get results or set you apart?
Keith: I bring a technical aspect an innovator’s perspective. I don’t just use tools. I think about how to make them to solve bigger problems. With Letterman, I took what could have been “just content” and used it like infrastructure: a foundation to build influence and opportunities. My ability to see systems and connect the dots is what helped me stand out and get results quickly. I really examine and pursue with the future in mind.
Carol: You see Letterman as infrastructure. Can you give me an example where your “builder’s mindset” turned what could’ve been just content into a real opportunity?
Keith: One campaign that stood out was when I tied automation with real-world outreach. I used Letterman’s structure to run the content and follow-up automatically, but I paired it with partnerships in the community, like local businesses who shared it with their networks. The automation kept it consistent and polished, while the human side gave it trust and traction. That mix proved the system could scale while still feeling personal.
Carol: Subscriber growth is a huge part of Letterman’s success. Outside of Facebook, what have you tried, or are you exploring, to bring in subscribers? How is your approach different from what others are doing?
Keith: I’m molding digital innovation with real-world connections. I use automation platforms, AI tools, and smart outreach systems to capture and nurture subscribers. Using all social media platforms, not just Facebook, and then take the communities, network and bring in business partners, so growth can be organic as well as tech driven. This mix makes my approach more sustainable than just ads.
Carol: When you blended tech-driven growth with organic networking, was there a campaign or partnership that stood out as proof this mix really works?
Keith: One example was when I used Letterman to feature local businesses alongside my own content. Instead of it being just another newsletter, I framed it as a platform that gave others credit for what they were doing. That small shift opened the door to partnerships, because those businesses started sharing my content with their networks. It turned what could’ve been a single issue into an ongoing opportunity to grow my reach and create collaboration.
Carol: What drives your passion for entrepreneurship, and how does that show up in your work day to day?
Keith: What drives me is solving problems with technology and turning concepts into working systems. Every day, I look at how different tools — whether it’s AI, automation, or sustainability tech products like Herbie — can make life easier and business smarter. My passion shows up in building solutions that people can actually use, not just ideas on paper.
Carol: You even brought up sustainability tech like Herbie. Herbie is a far infrared infused glass disc that helps with food reservation, right? Can you share one example where solving a problem with tech made someone’s day tangibly easier?
Keith: It sure is. It is an amazing product. There was this time when I introduced Herbie to a family that was struggling with food going bad too quickly. They were constantly tossing produce and leftovers, which meant wasted money and frustration. When they started using Herbie, they saw their food last noticeably longer. It wasn’t just about saving money. It gave them peace of mind and made daily life easier. It is a creative passion of mine to engineer tangible change with technology.
Carol: Looking back, what’s the most valuable lesson you’ve taken from Chad or from being in Entourage?
Keith: The biggest lesson has been that tools are only as valuable as the action you take with them. Chad reinforces that momentum matters more than perfection, and that clicked with my tech background. I realized that a half-built system in motion creates more results than a perfect idea that never launches.
Carol: Keith, what’s one project you launched “before it felt perfect” that ended up teaching you the most about momentum over perfection?
Keith: A product I launched before it felt perfect was my first automated newsletter workflow. The design wasn’t polished, the copy wasn’t flawless, but I pushed it live anyway because I wanted the system to run. Within a week, it not only reached readers but also generated real conversations and opportunities I wouldn’t have had if I’d waited. That experience taught me that speed of deployment creates momentum—action drives momentum, and momentum delivers breakthroughs that overthinking never will.
Carol: What’s one creative twist or strategy you’ve tried, whether with Letterman or your business, that really made a difference?
Keith: My twist was to treat Letterman like a tech platform, not just a newsletter. Integrated it with automation tools, AI, and partnerships so it became a hub — more than just content. That shift created leverage, letting one action ripple across multiple channels. It made the system more powerful than I expected.
Carol: Turning Letterman into a hub is powerful. Which integration or partnership gave you that first glimpse of how far that leverage could go?
Keith: The first time I saw Letterman’s real leverage was when I integrated it with my website and automation tools. Once published it didn’t just create a newsletter, it updated my site, seeded social content, and gave me a ready-made asset to share with partners. That single connection showed me Letterman wasn’t just a publishing tool—it was a hub that amplified every move I made. It was the moment I stopped seeing “content” and started seeing “infrastructure.”
Carol: If someone brand new came to you and asked how to succeed quickly with Letterman, what advice would you give them?
Keith: I’d tell them to think like a builder: use the system as your framework and plug into it right away. Don’t get stuck tweaking — launch, then refine. The faster you connect Letterman into your workflow, the faster it compounds results.
Carol: If you could boil that down to just one first action : the single “plug this in now” step, what would you tell them to do?
Keith: If I had to boil it down to one first action, I’d tell them: connect Letterman to an automation platform right away. That single step transforms it from a newsletter into a workflow engine—your publish goes to your site, your socials, and your partners automatically. It’s the fastest way to see leverage without adding extra work. Once they feel that compounding effect, they’ll never treat it like “just another email tool” again.
Carol: How has being part of this mastermind changed your business or the way you look at things?
Keith: It’s expanded the way I think about blending technology with relationships. The mastermind showed me that innovation doesn’t just live in code or automation. It’s in how you connect people and ideas. That shift made me see my business less as a solo project and more as a network of systems working together.
Carol: A “network of systems.” Agree. Can you share what shifted for you, maybe in how you approach partnerships now versus before?
Keith: I used to see partnerships as quick exchanges—help each other out, maybe share some visibility. Now I see them as pieces in a larger system. When I connect a partnership through automation and workflows in Letterman, one simple collaboration spreads across multiple channels and keeps producing long after the first push. That shift showed me partnerships are most valuable when they’re built into systems that keep compounding, not left as one-and-done deals.
Carol: What is the legacy you’d like to leave and/or is there a very clear message in all you do that you’d like known?
Keith: My legacy is to be known as someone who turned innovation into impact. The clear message in all I do is that technology isn’t just about efficiency, it’s about building better futures. I want people to remember me as the one who made tools and systems that saved money, improved lives, and created opportunity where there wasn’t any before.
Carol: That’s a big, inspiring vision. If you could wave a wand and see one part of that legacy in action today, what would it look like?
Keith: If I could wave a wand, I’d want to see the systems I’ve built already helping entrepreneurs free up time and focus on solutions instead of survival. It would look like people launching faster, wasting less, and seeing that momentum fuels opportunity. My legacy isn’t just about tools—it’s about proving that structure and innovation can give everyday people leverage. That vision, in action, would be a network of builders multiplying impact together.
To contact Keith:
Far Infrared Technology: hello@firdisc.com
