E132 | From Licorice Dispensers to AI Startups: Nicole Donnelly’s Entrepreneurial Journey

What does it take to go from a curious kid crafting licorice dispensers in the California desert to a trailblazing founder building AI tools that transform women’s health? In this powerful episode of The Proven Entrepreneur Show, host Don Williams sits down with Nicole Donnelly—serial entrepreneur, AI evangelist, and founder of AI Smart Ventures—for a raw, real, and radically inspiring conversation.

Nicole opens up about the highs and heartbreaks of her entrepreneurial path, including:

• Her earliest sparks of innovation and the moment she realized she was born to build
• The emotional toll of selling her first company—and being sued by her own family in the process
• How she rebuilt her life, her business, and her relationships with resilience and grace
• The importance of hiring for fit, not just faith, and how tools like StrengthsFinder and Kolbe changed her approach to leadership
• Her latest venture: “Charlie,” an AI agent trained on perimenopause and menstrual health data that helps women optimize their wellness with personalized, cycle-based recommendations
• Why automation is a form of care—and how AI can help entrepreneurs reclaim their time and sanity
• Her bold stance on banning nefarious uses of AI, especially in human trafficking and exploitation

Nicole also shares her “AI-first” mindset—how she uses tools like ChatGPT, Claude, and Gemini to streamline everything from budgeting to inbox management—and why every founder should start testing ideas before building them.

Whether you’re a startup dreamer, a seasoned founder, or just AI-curious, this episode is packed with wisdom, warmth, and wildly practical insights.

Watch the episode here

From Licorice Dispensers to AI Startups: Nicole Donnelly’s Entrepreneurial Journey

Hey, it’s Don Williams with today’s episode of The Proven Entrepreneur Show. Now we’ve been on an AI kick for a couple of episodes and I brought in the big gun from Vancouver, Canada, Nicole Donnelly. Welcome to the show.

Thanks for having me. You know I love AI and can’t wait to talk about it.

I know you do. I

think your company is like AI smart.

Yeah, we’ve got AI smart ventures, smart insiders, smart marketing, all the things.

Okay.

Love that. Love that. Love that. So, let me take you all the way back to your childhood home. Okay. Was there an adult in your household that was an entrepreneur?

Yes.

No. No.

No. Okay.

So what’s the moment?

when you knew that you were an entrepreneur, even if you didn’t actually call it that yet.

You

I’d say there were a couple of moments. There was the really the entrepreneur moment, but it was after I sold my first company. You know, when I was little though, I wanted to be an inventor. And so it was about sharing the things that I thought people would, you know, make their lives better. And I must’ve been maybe seven or eight years old and I made licorice dispensers and we lived in a mobile home on a dirt road in the desert.

Yeah.

in the middle of nowhere, California. And I put these licorice dispensers in the neighbors’ mailboxes. And to walk to the neighbors, you had to brave the dogs and the random things out there, dirt road, middle of nowhere desert. But I just was determined because I thought it would make their lives so much better.

I love that.

I love that. So to me, an inventor is like the ultimate problem solver and problem solver and entrepreneur kind of go together. And I know many people that had built a company and exited before they could actually spell entrepreneur. That’s not uncommon at all. Okay. So how long have you been an entrepreneur?

Yeah.

My whole life. I think my whole life. I started selling things to friends in the fifth grade. Yeah.

Yeah.

Okay, good. You’re my sister from another mister. Yeah, I love that.

So thinking back across multiple businesses, multiple industries, okay, and a couple of decades of entrepreneurship, tell me about the toughest day in your business and how’d you get through it?

Yeah.

Ooh, the toughest day. I hope my mom doesn’t listen to this. When I was selling my company, my first company, I had given my mom 5 % equity and I’d given my aunt and uncle 5 % equity because they lent me money in the beginning. And when I needed to sell it was the end of 2008 and we had a good offer on the table.

I needed to transfer intellectual properties, I had to buy their shares. They did not agree that, they didn’t agree that what I was offering was fair and it was more than the LOI. And my mom had been working for my company for three years at that point. She was living with us too. And she moved out and moved to Vegas with my aunt and uncle and they sued me.

Hmm. Sorry about that.

They tried to sue me. It didn’t work out because there was no, there were no grounds, but, that was, that was hard. That was sad.

Yeah, tough day. How’d you get through it?

how did I get through it? That’s a good question. It took a lot of years. I mean, at that time I had to push through in order to keep the business running and, you know, keep people in their jobs. So I couldn’t not.

you know, and being the breadwinner for the family and having a little kid there. There wasn’t an option, but it was more the years that came after that to heal the relationships because there’s even more more than that. Yeah, but it took years and I went to landmark.

Well, we won’t ask you to go there. Okay. But, but thank you for sharing.

was unfortunate cause COVID kind of ruined that in-person experience, but it was in landmark where I got just, it is up to me. It is up to me to reach out. Like my mom could never text me or call me again. I’m the one to do it if I want that relationship. And if I want that relationship for my daughter, took about six years before my mom came and visited.

and she came up once for my daughter’s birthday. it was, yeah, it still is a thing.

Yeah.

Well, there’s a lesson there, entrepreneurs.

can be a challenge involving family in your business because it’s multi-layered. so it can be, it’s a challenge working with people period, but it can be a deeper challenge with people that you have a multiple relationship. And I’ll tell you this that, I don’t know, 25 years ago, my son’s mother and I were divorcing.

and my business was on its backside. It was horrible. And I came home one day and like everything was gone. And except the boys and me and the way I got through it is I just put one foot in front of the other. And it was a couple of years of I wouldn’t say I was graceful. I wouldn’t say I was super intelligent. I would say I was persistent.

Hmm.

Yeah.

I would not

quit and there were days when there was no money, no resources, no nothing. But what do do? You’re a parent and you got people relying on you and so you go, go. Okay, thank you for sharing that. What about a lesson you wish you learned sooner as an entrepreneur?

Yeah.

I think with the family stuff, I had a mentor from WPO and they had a family business. They were going into their third generation in this family business. And if people grow up in it, you had asked me before, were there any entrepreneurs in the house? Well, there weren’t. And so if you work and you’re expected to and it’s a legacy, then it’s a different environment typically. And I could see how the family could work together.

for myself and for the people that I hire, it’s also looking at not just that I like the person, but making sure they really do have the skills and they’re the fit, right? That was a really rough lesson in the first business because I believe in people and I believe that they can learn and they can do a good job and…

Yeah, it’s not in that way. It feels like I have that naive optimism, you know, when it comes to hiring and people. And I have definitely learned a lot in that and to not be shy about saying, Hey, let’s do strengths finder and Colby and you know, we’re culture index and some of those things to see if we are a good fit and make it more objective and not just me because that is not my magic.

And it is for other people, but it’s clearly not mine.

Yeah.

Yeah, I totally understand. For years, I tried to hire people that look like me, talk like me, walk like me, act like me. Challenge, I’m kind of a unique, everybody’s unique, but like I’m kind of like on the edge of unique. And so they don’t grow on trees. And then it took me a long time to learn that the best teams are teams made up with people who have different skills, different superpowers. And that’s the best team.

Mm-hmm.

Mm-hmm.

shared my Clifton Strength Finders the other day with a part where we’re entering a partnership. And he sent back to me, he’s like, your top five in the order they are, there’s only one person out of 33 million that have that in that order. And I was like, okay, well, my dog thinks I’m special too.

Yeah.

You know, but but you know, that’s how goes.

Yeah, it is. I love StrengthsFinder.

Yeah, I like all of them. In fact, I put them on my website. It’s DonWilliamsGlobal.com about, because I’m an open book. I’m like, either we’re going to work really well together or if we’re not, let’s just not. I’ll still love you and I’ll do anything I can to help you, but maybe we don’t actually line up to where we’re complimentary to each other. ⁓

Yeah.

Yeah. Yeah.

Yeah.

Because hey folks, life is short. And I saw something Gary Vaynerchuk did the other day. And so I ran my own math. But he was saying, the opportunity to have a life is pretty astronomical mathematically. And so me and my good buddy, ChatGPT, we went and did some math. And I said, if we go back to 500 AD, and if I’m 60,

Mm-hmm.

today and if at the moment right before conception there is 300 million people that could have been born, you you fertilize the egg. know, each sperm was a person. You survived. And if you run that math,

Mm-hmm.

1 in 300 million for 60 generations. It’s like for you to actually be on the planet today is 1 in 2 with 477 zeros.

Yeah.

There’s a lot of zeros.

It’s a lot of zeros and

and chat GPT I have no way of verifying this but they say that’s more than the atom count of the entire universe So hey if you’re alive today, you’re a miracle Your kids are miracles your friends are miracles act like it it’ll it’ll work for you. Okay next question if somebody listening today

Yeah.

wanted to follow in your footsteps. You were their role model. What’s the first step?

The first step, well, I was having a conversation with a friend who wanted to launch something and I said, just launch it, put up a website and see if people sign up. You know, I don’t believe, okay, so some of the things need a lot of research, but most of the ideas people have, it’s like, just get it out there and do it and test and see if people will pay money for it.

Mm-hmm.

Pay money to get on a waiting list, even if it’s $5, it shows that buying intention. And with AI, you can put up a website almost instantly. It takes a couple minutes now if you use something like Gamma. And you can test your ideas really quickly, at least to see if they have this validity. There are certain things. I mean, I’ve worked in biotech, too, and fintech. There are products that take a long time to develop.

you see this fit, but now we can put up landing pages and test it. We can try to sell things, know, whatever it is, make it at home, digital services, t-shirts, whatever you want, but test it and like, just don’t be afraid of it. And that’s the number one thing is just to take action because I get asked all the time about these things and…

you know, if I think something’s a good idea, it’s like, I might think it’s a good idea. Just like hiring that person. is a good idea? But does the data say it’s a good idea if I post that somewhere, are people going to like it? Are they going to pay for it? You know, so I don’t think it’s most of the things it’s not worth building out the backend until you see if it’s even viable. And we can test viability so fast now.

I love that.

I love that. So the two things I’ve really heard is one, start ugly. Don’t wait till it’s perfect. Don’t overthink it. A junkie first draft is better than no draft. Okay. And two, and I think this is critical, will people pay something anything? And

Yeah.

Yeah.

Yeah.

And if you put something out there and you put together a waiting list of a hundred people who will pay something, man, you might have something. But if you can’t, you might not have something. I mean, it just, just because you think it’s a good idea or I think it’s a good idea or Nicole thinks it’s a good idea. What I’m always telling my team is like, I’m a horrible example.

Yeah.

Don’t ask me. I’m the world’s worst example. Things I think that are really cool, other people don’t. Things that are like, I’m totally over my head. You know, they go gangbusters. So ask a bunch of people. if you can get, and if you can put a hundred customers on something, you really have something. I mean, for sure, for sure.

Yeah,

I’m working on a new project right now and I shared it with a couple people and before I knew it, I had a list. It just spread so fast. And it’s like, okay, I’m going to take the next step and invest. I built the first version myself and I did a rough, you know, GoDaddy website where it was the AI website builder. And then I built an AI agent and

You know, it took maybe a day and cleaning the training data for this agent took the longest time and having it formatted properly. But I had it up and just sent it to a couple of people and they sent it to more people and, you know, got a list. I was like, all right, that’s a good one. You know, and it was something I had started building for myself because I wanted it. So of course I thought it was a good idea.

Yeah.

Well, and it maybe is a leg up if it solves a problem for you, maybe other people have the same problem. And the easiest way to sell is to solve a problem. Make something stop hurting. It’s much more challenging to make something feel better.

Mm-hmm.

Yeah.

Yeah.

that’s, so it’s cycle wise and it, I trained it on perimenopause and menopause data and research. And so you can say what symptoms you have and it gives different recommendations for supplements and exercise and I don’t know, lifestyle things as well. Sleep. it goes into, so I keep adding more things that it can do.

Mm.

But it’ll make my meal plan for a week and based on where you are in your cycle, there’s certain foods to eat at certain times so that you don’t have bad cramps. If you get your legumes on a certain days of the month, like the 13 to 15, then you will have less PMS and period symptoms. And so there’s some little magical things like that that I can’t keep top of mind all the time and remember and know what day I’m in.

So I made an AI agent, Charlie, that helps with that. And now I’m paying somebody to build out more to make these calendar integrations and some of those so that I can get alerts on my calendar of like, hey, get your black beans today or whatever, you know? Time for evening Primrose oil.

love that. I have a friend who, he was an art major and his wife is an MBA, I think. so, you know, kind of the whole opposite attract thing. And he’s like, hey, I automate everything. I automate everything.

Yeah.

And, you know, my wife likes flowers. don’t ever remember to send flowers. I have a subscription that sends her flowers every four to six weeks at random times. I automate everything. And to me, one of the big advantages and kind of simple, simple uses of AI is just, I’m not even sure all automation is AI. It’s not, but

No.

But man, it makes people’s lives so much easier. Automate, delegate or automate or question, should I be doing this at all?

Yeah.

Yes. Yeah. And this is where I get really excited because there’s so much that you can automate and there’s ways that you can use AI automation and humans in every workflow and process in your business and life too. And we call the systems like systems of care, either for your customers, your employees, and how can you automate systems of care, which kind of contradictory perhaps.

But the flower example is a perfect example of an automated system of care. He knows that she wants that. I would love that. I wouldn’t care if it’s automated. If I get flowers, I think that would be nice, not just as an apology thing, but to have in the house. so when you can do that in your business and you can deliver more of that magic to your customers because you’ve automated the care, they’re going to

they are going to have a better experience with you.

Okay, what’s one simple way any business owner can use AI today to save five or ten hours a week?

that’s a good question. There’s so many ways.

Just

one simple solution.

I’d actually say it’s the mindset of it. More than what you’re doing is getting in the habit of asking AI first. So if you have to sit down and do a spreadsheet, say, can AI help me with this? know, if doing a budget, something like that, those are the things that I hate to do. And so I try to pawn it off on AI. And so I would say become a little bit more lazy, ask AI first, and then dig into it, double check your work.

And if you can get in that AI first mindset, even when it comes to writing emails, like I have AI in my inbox. It organizes my inbox and it drafts responses to all my emails. Yeah. Affirmative and negative. Yeah. It is a huge time saver. And that one, that was a big one for me, the inbox.

Mmm. What a time saver.

And I tried a lot of different tools and there finally one came out that really made a difference for me. And I’ve been on it for maybe two or three months now. but it saves me so much time in my inbox and I don’t lose things that I need to pay attention to. yeah. So get in that AI first mindset more than anything, just open up chat, GBT, Claude, Gemini, whatever you like to use and have it start doing your tasks for you.

I love that. I can share that I’m selling an interest on a company to my partner. And so a couple of years worth of P &Ls, a couple of years worth of balance sheets, their offer. so because I’m very jealous of time, I send it to my accountant with just an email.

Just one question. What do you think my interest is worth today? And I upload it to ChatGPT and say the same thing. And they come back within 2 % of each other, the account and AI. And my total effort, maybe two minutes.

Yeah.

And so, I mean, I literally never looked at any of it. so, so I love that. Okay. all right. Here’s a tough one.

Okay.

If you had to ban one use of AI forever, what would Nicole ban and why?

you

If I had to ban one use of AI…

nefarious uses of AI. ⁓

if you had to ban

one use forever.

I know I’m saying I’d ban nefarious uses. mean, it’s a broad category, there’s so many, anything that has to do with like sex trafficking, human trafficking, children trafficking, child porn, those sort of things. This can spread that kind of stuff so fast. And those are the kind of people that will adopt and use and.

Okay.

even more than the military warfare because they’re going to be warring and warfaring forever, right? Like those battles will happen. And it’s the human trafficking uses.

I love that.

I think that’s a great answer. you know, it may have all started with the military anyway, you know, 40 or 50 years ago, probably did, you know, and we’re just now seeing it today. Okay. If one of our listeners wanted to reach out to your company or you, what’s the best way to do that?

Yep.

You can go to AI Smart Ventures and we’ve got an email list you can get on. We do a newsletter every week. We try to keep it short and interesting of cool AI projects going on. We always cover med tech too. There’s a lot going on in medicine, but all the usual suspects as well. And we also, in our newsletter,

So once a week we do AI labs and we’ll do a summary in the newsletter of what the experiment in the lab was that week or what we learned about. And we cover things like AI SEO or current marketing things that you need to know with AI. And so we try to keep people up to date because AI changes so much. But we do newsletters every week. So I’d say a bare minimum, like get on the email list and start.

listening and see what interests you and then come participate when we do open sessions.

Love that. Nicole, thank you so much. It’s been my pleasure to have you as a guest on The Proven Entrepreneur Show.

Thank you, thank you so much, Don.

You bet. That’s today’s episode of The Proven Entrepreneur Show. We’ll see you next time. Thanks. Bye.