Our Spotlight Recommendation
“Joe is a fabulous host. The atmosphere in his meetings is always welcoming, and the focus on connection and partnership really stands out. Looking forward to attending more in the future.”
–
Katrena Drake
I support tech founders running bootstrapped and funded startups from pre-seed to series A.
About Us
Digital Cowboy is the strategy and intelligence engine behind RepUpgrade, an AI-powered reputation and marketing system for independent and family-owned Italian restaurants.
RepUpgrade helps great restaurants turn customer words into stronger reviews, better Google visibility, useful marketing content, more reservations, and fuller tables. We focus on restaurants whose food and service deserve more online proof than they currently have.
I also host the AI Mastermind, where builders, consultants, service providers, and operators gather to understand what is changing, what matters next, and where new opportunities are emerging. Those conversations become weekly signals, full briefings, partnerships, and practical business systems.
Everything is built through the ACT framework: Authority, Conversion, Traffic. First earn trust. Then build the path. Then bring more people to it.
Digital Cowboy finds the signal. RepUpgrade turns customer words into proof, visibility, and growth.
How We Got Started
Digital Cowboy began with a simple mission: help small businesses use technology without losing their voice.
Since 2012, I have worked across digital marketing, messaging, media, and automation, including leadership roles with Schurz Communications and USA Today. I saw powerful businesses buried beneath noise, outdated systems, and marketing that failed to reflect the quality of their work.
When ChatGPT arrived in 2022, I saw more than another tool. I saw a new printing press—one that could amplify clear thinking, lived experience, and authentic language at scale.
That insight became the foundation for the AI Mastermind, where builders, consultants, and operators gather to understand what matters next. It also led to RepUpgrade, which helps independent Italian restaurants turn customer words into stronger reviews, visibility, reservations, and fuller tables.
Digital Cowboy helps good businesses become easier to see, trust, and choose. Do something great with your words.
The products and services we offer
Recommendations Received (349)
"Joe really knows his stuff! What a great resource to have!!"
"He is very knowledgeable about ways to use AI in your business"
Networking Events
Monday Aug 3rd 9am-10am CDT
Love cool AI stuff? Check the guide to get the latest: ➡Get the guide.
Join us for the AI Empowerment Connect™, a networking event designed to b...
Monday Aug 3rd 2pm-3pm CDT
💼 Welcome to the Business Growth & Relationships Community Smart Connect! 🎉
This is the room where relationships fuel growth. It’s not about pitc...
Tuesday Aug 4th 12pm-1pm CDT
AI Mastermind
The AI Mastermind is a live, high-frequency working room.
Built for consultants, builders, operators, and AI-forward professional...
Products & Services
The Clarity Session is a focused 20-minute conversation designed to uncover the key challenges your business is facing. Whether you're dealing with...
Most business owners don’t realize their Google star rating is directly tied to revenue. Want to see how much more you could be making? Tap here!
...
Recommendations Given (102)
"Jeff is an individual who clearly touches the eternal now when he’s creating. His openness and..."
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"Jeff is an individual who clearly touches the eternal now when he’s creating. His openness and the brand he’s built over the years reflect a rare harmony—bringing together the grounded strength of strategy with the flowing creativity of art. What inspires me most is how he continues to follow his dream—writing, creating, and now illustrating books. He carries both the precision of the masculine and the wonder of the feminine into his work, and that balance shows up in every project he touches. It’s rare to find someone who embodies both clarity and imagination so fully. Very cool to see where his journey is heading."
"Kara is a natural creative with a real gift for design. She built a beautiful new SmartHeat..."
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"Kara is a natural creative with a real gift for design. She built a beautiful new SmartHeat website with just a touch of guidance. Her ability to adapt quickly and translate vision into something that looks and feels right is impressive. I have worked with Brizy CMS for almost a decade (2017)...she picked it up so fast I was embarrassed for how long it took me to get where she was at in 2 weeks!
She’s also incredibly caring and easy to work with, which makes collaboration feel effortless. What I appreciate most is how she blends sweetness with sharp creative instincts—a balance that makes her a joy to partner with and a real asset to SmartHeat."
Recent Activity
The Relationship Layer is the next logical step after reviews. In E-E-A-T terms, reviews are proof of experience; referrals add the dimension of trustworthiness.
I love Alignable for this.
For business consultants and creators, Alignable is where those trust signals live. While a book,...
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The Relationship Layer is the next logical step after reviews. In E-E-A-T terms, reviews are proof of experience; referrals add the dimension of trustworthiness.
I love Alignable for this.
For business consultants and creators, Alignable is where those trust signals live. While a book, project, awards, or even Google Biz Profile (but more important for local producers) are awesome to use as your authority...Alignable provides real people with real WORDS and the best part of it is- you just have to be helpful!
A well-written recommendation or verified connection here, isn’t just social proof — it’s structured data that feeds discoverability and credibility. These reviews can now be placed on your website. This is where Alignable truly signs for consultants, coaches, and creators looking to build into this new economy. If trust is (it really always has been) the future, and you are helping people and getting real recommendations based on the custom and format of your brand...
Those real words build your authority. And:
Real authority now is authenticity, and real reviews are the backbone of both.
Got me curious @ericgroves with all the mention of CRMS...we getting access to a REST API? 🤠 Cuz my Moxie (my CRM) would appreciate that.
Glo is such a real, authentic person who has this unassuming personality....but she is a Lion! One of my most favorite people to listen to for answers that will come from a different angle...
🤠
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Glo is such a real, authentic person who has this unassuming personality....but she is a Lion! One of my most favorite people to listen to for answers that will come from a different angle...
🤠
@samrafoss... 🌹 You are number 9 here, number 1 in Canada and number 1 in my ❤️ and many others. ♾️.
Congratulations to all!
🥂 You all are Doing Something Great. 🤠
(more)
@samrafoss... 🌹 You are number 9 here, number 1 in Canada and number 1 in my ❤️ and many others. ♾️.
Congratulations to all!
🥂 You all are Doing Something Great. 🤠
2 Replies
Love the responses so far. ⭐⭐⭐⭐⭐ Alignable does so many things well. But, I am only going to give one reason why I love it so much... Before I do that I want to extend my genuine thanks and gratitude to all of the amazing people I've met on Alignable. This has been the most authentic year of...
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Love the responses so far. ⭐⭐⭐⭐⭐ Alignable does so many things well. But, I am only going to give one reason why I love it so much... Before I do that I want to extend my genuine thanks and gratitude to all of the amazing people I've met on Alignable. This has been the most authentic year of my life and everyday is better and better because of you. Thank you to the people who have shown me the gift called: Know, Like, and Trust. The list would be far too long to name everyone. lol. But y'all know who you are. Much ❤... 🔥Here is the reason: I am lucky enough to have met my business partner on this platform. She is amazing. We see the same thing (through different filters). And, I can't wait for 2024. Somebody tag her ➡ 🧭 since I can't do it in the post. Thanks! I only need one reason to justify loving Alignable, but I could give 997 more. Then some... 🤠
2 Replies
⭐ ⭐ ⭐ ⭐ ⭐
1. Claim and optimize Google Business Profile. It is the who, what, where, when, why, and how. Make sure you list ALL SERVICE areas. Not just where you are located.
2. Make sure your website reflects what your GBP says. This tells confirms for Google the answers above.
3....
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⭐ ⭐ ⭐ ⭐ ⭐
1. Claim and optimize Google Business Profile. It is the who, what, where, when, why, and how. Make sure you list ALL SERVICE areas. Not just where you are located.
2. Make sure your website reflects what your GBP says. This tells confirms for Google the answers above.
3. Authority and trust- ask for reviews every single chance you get. The keywords in your reviews will drive your ranking when people look for photographer in your area.
1 Reply
Back in May, Pew did a poll. Lots of people tried it. Once.
Very few have gone back. In my experience with most people, it is like learning a whole language.
Understanding prompts;
Context, Instruction, Details, and Input
can be a challenge.
When it doesn't work like Google does,...
(more)
Back in May, Pew did a poll. Lots of people tried it. Once.
Very few have gone back. In my experience with most people, it is like learning a whole language.
Understanding prompts;
Context, Instruction, Details, and Input
can be a challenge.
When it doesn't work like Google does, people go back to what they know. Which is Google. I think this is funny because Google now has custom AI generative answers first, at least organically.
1 Reply
"Always face the brutal truth, but never let faith waiver."
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"Always face the brutal truth, but never let faith waiver."
380 comments in 10 minutes... 😳 😮 Whoa!
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380 comments in 10 minutes... 😳 😮 Whoa!
At USA Today we offered them for $199 to $399 monthly. it really depends on what you are offering. E-comm vs service based. Local vs regional vs national.
The other thing I would add, is that people only pay for what they understand.
SEO is a form of traffic. It is also the most...
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At USA Today we offered them for $199 to $399 monthly. it really depends on what you are offering. E-comm vs service based. Local vs regional vs national.
The other thing I would add, is that people only pay for what they understand.
SEO is a form of traffic. It is also the most important and hardest to get.
While it is important, making the distinction between conversion and traffic is exceptionally important. Everyone sells traffic. EVERYONE.
I guess all I am saying is that there is a massive difference between conversion and SEO.
2 Replies
I use Covve. Scans card, mini CRM built-in, reminders for birthdays, etc.
Plus it comes with a built digital card that people can scan a QR code and grab all of your info.
Lots out there. Covve UX is excellent.
(more)
I use Covve. Scans card, mini CRM built-in, reminders for birthdays, etc.
Plus it comes with a built digital card that people can scan a QR code and grab all of your info.
Lots out there. Covve UX is excellent.
