Debunking Stereotypes: How Encore Entrepreneurs Are Leveraging AI for Business Success

The Issue

Two weeks ago, I was a keynote speaker at the Age Equity Alliance 's Global Fall Forum, covering topics relevant to older workers and their employers.

Preceding me on the virtual stage was Generation 's Mona Mourshed , who shared some findings from their most recent study, Age-Proofing AI: Enabling An Intergenerational Workforce to Benefit from AI.

Among the findings that struck me:

• Employers continue to have a bias against older workers, with only one third of U.S. employers saying that they would consider candidates over age 60 for roles that regularly use AI tools, whereas 90% said they would consider candidates under age 35.
• Only 13% of U.S. workers age 45+ said that they currently use AI at work.

On both sides, this seems like a huge missed opportunity. It seems to me that experienced talent can bring so much to AI use, including better ability not only to generate prompts based on built up insights and experience over time, but also to vet the results.

The Generation report went on to say:

This gap points to a need for employers to marry experience with skills to unlock the full benefit of AI—by finding use cases that incorporate AI into specific roles and experience levels.

To establish some use cases, I reached out to some friends who are encore entrepreneurs, meaning that they established new businesses after age 50, building on their prior skills and experience. I asked them each these questions:

1. What AI tools do you use, and what do they help you with in your business?
2. How did you learn how to use AI?
3. How has your prior experience equipped you to use AI?
4. What would you say to those who think that AI tools are only for younger people?

Their responses, in their own words below, establish an overall use case: That the experience of older adults INCREASES the benefit of AI use, once again debunking stereotypes that some employers may hold about older workers and tech. In short:

Experience + AI = A Formula for Success

The Use Cases: How Encore Entrepreneurs Are Using AI to Advance Their Business Success

Viveka von Rosen, Founder and CEO, Beyond the Dream Board

I met Viveka, an early adopter of AI, when we were both in one of Kami Guildner Coaching 's Mastermind Programs. She was planning her encore business, Beyond the Dream Board, a coaching and consulting business focused on empowering women 50+ to transition from corporate to entrepreneurship, creating legacy businesses aligned with their values. 

What AI tools do you use, and what do they help you with in your business?    

I have been using AI for almost 2 years now and there is NO WAY I could be where I am in my business without it.  While I am far from an expert, I am just that far ahead of the game that I am often asked to present AI tools and strategies to my client’s companies  and other associations.

Tools I use daily:

• Premium ChatGPT  - for so many things (in fact, I wrote an article about it)
• Magai.ai as an AI dashboard to manage my personas, prompts, and create images for my content.
• FlyMSG to help me streamline outreach and engagement on LinkedIn. 

Weekly I dip into:

• Castmagic.com to edit and create content from podcasts I am on
• Peech.ai to edit video 
• Brandwell.ai to help me create content at scale

How did you learn how to use AI?    

I’m mostly self-taught, but my Aha moment was watching Jordache Johnson at a conference last year.  He taught me the necessity of “seasoning the pan” to get better results.  More recently I was blown away by Andy Crestodina at the Agents of Change conference.  And of course Steve Dotto has great AI tutorials as well.  In addition, I dip into YouTube tutorials, podcasts and there’s a lot of trial and error. 

How has your prior experience equipped you to use AI?    

As someone with extensive experience in social selling and content creation, I understand how to craft compelling prompts and evaluate AI-generated outputs.

Years of working with clients on messaging and storytelling have given me a strong foundation in identifying quality results, ensuring the AI-generated content aligns with brand goals and messaging.  And I’ve always been on the leading edge of things (one of the original Social Media Influencers), so the tech doesn’t scare me.

What would you say to those who think that AI tools are only for younger people?    

Tools like ChatGPT are user-friendly and designed for people of all tech levels. Many of my clients, who are 50+ women transitioning to entrepreneurship, are discovering how AI can streamline their operations and free up time to focus on what matters most. It’s never too late to embrace technology that can make life easier—AI is here to serve us, not replace us.

Leo Robledo, Culinary Craft Founder, Global Cookbook Author and Gastromist

I met Leo, an AI Pioneer, after I gave the closing address at CWI Labs 2024 Equity Summit, encouraging participants to challenge stereotypes about older adults in the workplace. He came up to me after, with a copy of a cookbook he had just published, and explained how he was leveraging AI to amplify the knowledge he'd gained as an executive chef for Hilton for 30+ years, creating customized cookbooks.

What AI tools do you use, and what do they help you with in your business? 

I Use ChatGPT 4o, DALL-E 3, Gemini, and Imagen 3. ChatGPT and Gemini are natural language Chatbots that act as assistants for research, development of material, and proof readers. DALL-E 3 and Imagen 3 create photorealistic images with immersive backgrounds, with 3-D perspective.

How did you learn how to use AI?

I am 100% self taught.  I started using ChatGPT3 a little over 2 years ago when very few people knew of it. AI can actually mentor you in how to best use it.

How has your prior experience equipped you to use AI?

I was a chef in hotels for 30+ years. In my capacity I was proficient in the Office platform. When I retired, I started archiving my many recipes, and when I came across chatbots, I realized how important it could be as a tool. With my previous experience I am able to train the model to generate recipes and images that are accurate and resemble actual food.

What would you say to those who think that AI tools are only for younger people?

That anyone that is going to be successful with AI, must have a very strong knowledge of the subject they want to work with. AI does not generate, in my case, cookbooks out of nothing. If you do not have the base knowledge, it can not guess what you want, or interpret your thoughts.

The fact that it uses natural language makes it very easy for nearly anyone to be a proficient user even if you don't have previous knowledge of programming or writing code.

I am an expert in food culture, and with the AI tools, I am going to complete this year a series of cookbook about the entire American  continent, a task that has taken me a little over 18 months. When finished it will consist of 4 volumes for Canada, 11 for the US, 1 for Mexico, 4 for the Caribbean, 4 for Central America and 6 for South America, for a total of 30. All published and available at Amazon and Barnes and Noble.

Jacqueline (Jack) Perez, Founder and CEO, Kuel Life

I met Jack at Diana Place 's Third Act Quest when she and I served on a panel on Rewriting This Life Stage. Her digital platform, Kuel Life, is dedicated to normalizing aging for women through curated content and women-driven brands.

What AI tools do you use, and what do they help you with in your business?

I use ChatGPT and the better question is what doesn’t it help with? All kidding aside, as a solopreneur, sometimes I need some “help” brainstorming and that tool is fantastic. I certainly have trained it to give me some great SEO-optimized titles for our articles - that’s for sure.

How did you learn how to use AI?

I played with it…. it kinda taught me…. which I guess is a little scary, isn’t it? I also have dabbled in some youtube videos and TikTok ones as well. 

How has your prior experience equipped you to use AI?

The ability to think critically is important. Good prompts are key to good results, learning to ask the right questions makes or breaks the experience.

It has taken me a while to get comfortable with the breadth of questions that come up that I can at least get a headstart in solving through AI.

What would you say to those who think that AI tools are only for younger people?

To quote Bob Newhart: “STOP IT.” Once you pop that cherry, I promise you won’t go back. Get on it, it’s free (at least until you’re addicted), play with it…. see for yourself.

Angelle Fouther, Principal, Kindred Communications LLC

I feel like I've known Angelle forever, from back in her days directing communications for The Denver Foundation , as well as her efforts to address a food desert in her community, when she became a client of my consulting firm. When she started Kindred Communications, LLC, I relied on her to not only create logos and a style guide for Changing the Narrative, a leading anti-ageism initiative , but also blogs and social media content, and more. And her daughter, Daryn Fouther , created my logo for Encore Roadmap.

What AI tools do you use, and what do they help you within your business? 

Currently, I use ChatGPT 4o as my primary tool. But I rely on other AI support tools like Canva, Fathom (AI notetaker for Zoom), and Grammarly (which just offered a prompt correcting the spelling I incorrectly typed 🙂).

How did you learn how to use AI?

After a couple of years of stubborn resistance, I just jumped on ChatGPT 3.5 and started asking it questions. I was impressed with the speed and the breadth of information I could find. I decided to subscribe to GPT4o because it has an internet interface, which bumps up your information access exponentially. It’s really not hard to use. There’s a chat bar, and you type in questions/prompts. It does the rest of the work. 

How has your prior experience equipped you to use AI? This might include knowing what it could be used for, generating good prompts and assessing the quality of the output, for example. 

I think anyone with experience surfing the web is equipped to start using AI. It’s about framing questions and prompts to get the outcome you are looking for and refining those if the information is off.

What would you say to those who think that AI tools are only for younger people? 

I would say, and this is harsh, prepare to go extinct like the Raphus cucullatus, Mammuthus primigenius, and Smilodon. Those are the Latin binomials (names) for the Dodo, Woolly Mammoth, and Saber-Toothed Cat, respectively (I got them on ChaptGPT).

I would also say that to keep ourselves from going extinct, each of us needs to maintain a niche and not rely too heavily on AI. It sometimes makes mistakes and is really bad, I’ve noticed, at equity-focused language.

I can’t get it to not talk about “empowering disadvantaged minorities.” The day will come when it becomes woke, but for now, it is out of touch there.

And How Am I Using AI?

I've become an avid AI user for work and play. For example, this weekend, I generated a packing list that would fit into a single carry on bag for an upcoming two week trip to Portugal, asking Chat GPT to accommodate the weather in the four locations I'll be visiting, my planned activities, etc.

At work, I use AI to do the things I hate doing:

• Finding citations in the proper format for research that I've read and am including in speeches or articles
• Summarizing meeting notes
• Generating images that illustrate how ageism is baked into AI (I know, this may seem conflicting, but it's not) for an article like this one I wrote about "Who Is An Entrepreneur?"

What I won't use AI for: Writing

I have a distinct voice and point of view, honed by my decades of working toward community, organizational and social change.

The neutral tone that AI generates never works for me even when I've "seasoned the pan" by giving Chat GPT sample articles I've written, and I've found it a waste of time to generate something and then just rewrite anyway.

Key Lesson Learned

For each of the entrepreneurs I interviewed, it's the insights and knowledge built up from their prior experience that helps them generate good prompts, assess the results and most importantly, know how it can be used to advance their business success.

If employers can tap into this, they will have a pathway for, in the words of the Generation report, simultaneously motivating midcareer and older workers to use AI and register productivity gains.

Call to Action

1. Feel free to SHARE this column.
2. When you hear people assert stereotypes about older workers and AI, speak up. Let people know that not only is AI being adopted by people of all ages, but also that the insight that experienced workers bring to AI helps generate better prompts and more critical review of output, ensuring accuracy and leading to increased productivity.
3. Share YOUR AI story. How have you used AI to help your organization or business? Let me know in the comments, and I'll include in a followup column.

@ Janine Vanderburg, 2024.

As CEO of Encore Roadmap and co-founder of Changing the Narrative, a leading anti-ageism initiative, Janine brings over three decades of experience leading social and organizational change initiatives to her current work speaking, writing and consulting with businesses, media and brands on how they can become more age-inclusive, leverage the skills of older workers, and help intergenerational teams succeed.

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