- Chris Winfield owns a brand-coaching company helping small business and entrepreneurs.
- He discovered AI using Dall-E in 2021 and later became enthralled by ChatGPT and other AI tools.
- By selling AI products and using AI tools, Winfield made $2.7 million in the last 6 months.
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This as-told-to story is based on a transcribed conversation with Chris Winfield, the owner of Super Connector Media and Understanding AI, that has been edited for length and clarity.
I’d been in the public-relations business for eight years when I started experimenting with artificial-intelligence tools like Jasper and Copy.AI in 2021. They could create copy that captured my brand voice for email newsletters and social media. I got excited and thought, “This is the coolest thing ever.”
Little did I know what was on the AI horizon.
Before starting my company Understanding AI, which helps other business owners leverage AI tools, I owned a PR agency and brand-coaching company called Super Connector Media. I founded it with my partner, Jen Gottlieb, in March 2018.
Having a PR agency was never my dream, so I sold the agency side in 2022.
I used my downtime to learn AI
I remember when Dall-E was released last summer, my mind was blown. I could type something into the tool, and it made a picture — it felt unbelievable.
I no longer had to manage the agency and had more time on my hands to explore AI tools.
Later, that autumn, ChatGPT was released. I started experimenting with how to use it for Super Connector Media. At the time, our main focus was running personal-branding workshops.
I would ask ChatGPT to help me define our ideal client and write journal entries as that persona, then turn the journal entries into ad copy.
For every hour I spent learning ChatGPT, it felt like I got 40 hours back. I had never used anything that could give me results that quickly.
I started sharing what I was learning in late 2022 on Facebook and via email with my audience of business owners and entrepreneurs.
People wanted to learn about generative AI but already felt behind
Talking with my audience via direct messages and market-research calls, I found that business owners who had yet to try ChatGPT felt overwhelmed. They thought AI was everywhere and they were already behind.
I knew AI could improve their businesses and workflow if they could overcome their fears. So Jen and I started teaching AI use cases for businesses via paid online challenges.
We ran our first challenge in January and had 350 customers. We promoted the challenges on social media and through our email lists of over 120,000 people, as well as with paid ads on Meta’s platforms.
We started with a $25,000 advertising budget for challenges.
After a challenge, if someone wants more support, we offer courses and “mastermind” programs that have prices in the four-figure range and in the low five figures, respectively.
These packages show people how to grow a profitable personal brand and business online using AI to streamline the business-building process.
Teaching AI to our audience skyrocketed revenue and growth
We now run six-figure ad campaigns per challenge, and over 40,000 people have paid to be part of our challenges in the past eight months.
Since we incorporated AI products in January, our revenue has jumped to $2.7 million in sales.
We started Understanding AI with eight Super Connector team members and expanded to 17 to help with sales, ads, videos, and customer support.
We earn revenue by teaching people how to use AI tools, but we also use AI tools to maximize our revenue.
How I use AI to improve my own business’ workflow
I use ChatGPT to help create marketing material. AI generates 80% of the material, and my input is the remaining 20%. Sometimes I’ll add more of my own voice. Other times I just change the headline. I always remind my clients that AI isn’t a foolproof replacement for your brand voice.
Once you’ve mastered one tool, you can build your AI stack.
I’ve found memes work well in ads, and Supermeme.AI helps you generate memes from text inputs.
I uploaded ads recently with AI-generated memes, and they turned around a campaign that wasn’t doing well. The ads we created with Supermeme lowered our cost per click by 72%. It’s a tool that requires less than 1% of my time but makes a big difference.
I spend between $5,000 and $7,500 monthly on AI tools. It varies based on how many tools I’m testing.
When considering investing time in a new tool, I follow the rule of three. If I hear about a tool from three sources or people I trust, I will spend time looking into it. Otherwise, all the new AI tools can become just shiny objects.
I’ll then consider whether the tool would be helpful for my business and whether I can teach a lot of people to use it. I try to find tools that are relevant to small-business owners so I can teach them as part of my AI programs.
Sales AI nearly doubled our revenue between challenges
WooSender is an AI-powered sales assistant that we’ve used since April. If someone applies for our “mastermind” program, I can assign the lead to one of our two salespeople, and WooSender reaches out to the prospective customer as if it’s the salesperson with on-brand messaging.
The tool automatically finds available times in the salesperson’s calendar. If someone replies that they want to book the demo, it books the appointment, sends the calendar invite, and texts the person a confirmation.
After we implemented WooSender, we did just under double the sales for the next challenge.
In July, we hired a second salesperson because our challenges were growing in popularity. AI has helped improve his close percentage.
Before AI tools, you’d have to listen to hours of sales calls to give feedback. Now we use Chorus, which detects conversion drop-off points. For example, our salesperson spent too long discussing deliverables on the call. When we removed that section, our sales went up.
Chorus also helped us identify bonuses for our packages. The tool tracks patterns and key phrases in customer calls and helped us realize that people wanted prompts, so we include those now.
We’ve made over $2 million in 2023 by helping people understand AI largely because of AI tools we’ve implemented in our own business that ensure nothing slips through the cracks. Every person gets spoken with and followed up with, which is critical to the growth of our business. Marketing without sales is useless, and now we can do it for much cheaper with AI.