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The Struggles and Rewards of Millennial Entrepreneurship

Ruthie: I’m here with Ashley M. Williams, the CEO of RIZZARR, for our 3rd episode in her interview series. Today we are going to talk about the struggles and rewards of Millennial entrepreneurship. 

Has Being a Millennial Equipped You for Entrepreneurship? 

Ruthie: Our generation is characterized by some distinct struggles, namely college loans. That often transitions into the inability to purchase a home. We talk about those parts of being a Millennial a lot. But do you feel like being a Millennial has actually equipped you well for entrepreneurship, in some regards? 

A Millennial Advantage: Digital Nativeness

Ashley: I do, in the aspect of being a digital native. I think we’re so used to technology and having to adapt. I use technology to make things more streamlined for myself daily.

Even with the company, like building a tech platform and understanding all of these things that are available. I also think that because so many things in our society have changed so quickly for us, it’s always made us more prone to like figuring out how to adapt. 

We’re also aware of so many things, because we have the web at our fingertips. So even if people might say we’re disadvantaged because of our age, we also have other things that are equally as important for our growth and our development as entrepreneurs. 

millennial entrepreneurship

Millennials Have Lived the Technology Transformation

Ruthie: A defining characteristic of being a Millennial and part of Gen Z is that we remember what it was like before technology ruled the world. I think it’s wonderful that we’ve been able to see the transformation of our world, not even within our lifetime. I’m interested to see where it goes, but I think that helps us lean more into innovation.

I remember when we just had PlayStation, Nintendo, GameBoy, the Sega Saturn. But now I play games in my living room with my VR headset. I recognize that transformation. 

Years of Experience Isn’t Enough

I think that can also help us lean into being a bit more innovative. And to your point about us not necessarily having the wisdom, I caution people who talk to me about “years of experience in an industry.”

People might say, “Well, isn’t my 30 years of experience in the industry worth something?” Yes. But make sure that you add something else, so people know you didn’t just spend 30 years being mediocre. 

Ashley: Yes, because every year it changes. Something changes almost every month in marketing, so I totally agree with you. 

Ruthie: So being in the marketing industry for however many years doesn’t mean as much as you think it means when you’ve just been coasting along.

For example, I was on TikTok and I saw this airline ad. There was an older white gentleman with white hair who sat at a desk and spoke for 30 seconds. That’s all he did. It could have still been the same dude, but if he had dropped a “whoa” or something, it would have been TikTok appropriate.

There was no fun music in the background.


That was a terrible ad. I don’t know who told them to run that, but it was probably the person who’s been in marketing for 30 years. 

Conversely, I saw a Netflix ad and it showed this girl recording a TikTok. Her boyfriend was recording the TikTok, but then the camera started panning because he was looking at another girl. It was perfect. It was exactly what should have been on TikTok. Those are just 2 contrasting examples.

What Would You Say to Others Who Are Trying to Follow in Your Footsteps?

Ruthie: I very much admire you for your ability to drive through all of those struggles, get that funding, and build your platform. I’ve never heard of anything like it. You were able to find a solution to an industry need that nobody had thought of. So do you have a message for the rest of us who are trying to follow in your footsteps, in our own ways? 

Trust Your Intuition

Ashley: I’m so humbled by you saying that. Really trusting your intuition is so important. I haven’t understood that as much before as I have recently. I think sometimes we all can allow people to tell us what’s possible and what we should be doing. But you already know who you are supposed to be.

Once I really understood my passions and what I really wanted to help the world with, everything started adding up. 

I remember when I was at USA Today and I did a story on something related to Facebook or something, which led me to a breadcrumb around young people and the community part of RIZZARR.

And then more breadcrumbs kept coming. Study the breadcrumbs. Study what is happening around you that’s making you think, “Wait, that could be better. I could change that.” And then keep following it.

That’s the epitome of a sign for you to investigate further. 

Following Your Intuition Could Lead to Industry Transformation

One of my favorite movies is Flash of Genius. It’s about the guy who invented intermittent windshield wipers. One day, he was driving in his car in Detroit, Michigan. It was lightly raining, and the constant movement of the wipers irritated him. He thought, “I wish there was something that would make this work better.” And he invented it. 

Then there were a lot of troubles with the patent and everything, but my point is that he went through that inclination of, “This could be better. I can fix this.” And sure enough, he changed the entire industry. We wouldn’t have all these different settings on the windshield wiper had it not been for him.

Maybe someone else would have come up with it because that also happens when you don’t follow your intuition. 

Lean Into What Your Passionate About

My point is that you should really tap into your passions. What is it you’d like to do and try to see? Whatever you’re thinking about, there’s probably something just around the corner that someone needs to create in that regard.

I think most people just shrug it off like, “Oh, it’s nothing.” But it isn’t just anything, because we all have our own experiences that allow us to see something that someone else wouldn’t see. 

Ruthie: You’re definitely right. From childhood up until I was 27, not one time did I consider that I could start my own business for anything. My parents are not entrepreneurs. Their parents are not entrepreneurs. Not one time did I think, “Oh, I could invent something. I could design something. I could create something.”

Never did it once cross my mind. 

I told this to my youngest brother. He has his own goals and dreams, and I told him, “Hey, if you feel like you really want to move forward with this, we can work on a business plan. If I’m in a position to invest, then I will. I will connect you with people that I know.”

I don’t want my brothers, sisters, or children to feel like they can’t flourish because they feel like there’s no way forward. 

Are There Any Struggles You Associate With Being a Millennial?

Ruthie: It doesn’t have to be a business struggle. It could be a personal struggle, or a personal struggle that translated into your professional life. But is there a struggle that you associate pretty much directly with being a Millennial? 

Ashley: The first thing that comes to my mind is our capacity to believe in ourselves. In our world, we make a big distinction between other people and ourselves. Those are those people. This is me.

But you could be one of those people. It’s hard to imagine that sometimes because it seems so far off. I personally have struggled with that. There are times when people are like, “Introducing the founder and CEO of RIZZARR.”

And as the company grows, I’m like, “That’s me!” It’s a bit unbelievable. 

Learn more about why Ashley founded RIZZARR in our first interview.

When I was hosting a show at USA Today, I would be in the middle of the newsroom, everybody would be looking at me hosting the show, and I’d be like, “Is this my life right now?”

So I think we have the capacity to believe that we can do whatever we imagine we can. It may take some time and there may be some hardships. I’ve done lots of ugly crying, but you just have to pick yourself up and keep going, you have to. 

Ruthie: I saw a post on LinkedIn by a friend of mine who’s a motivational speaker, Rachel Druckenmiller. She posted a picture of the bread aisle, and there’s 20 different brands of bread. 

The caption was something like, “If you think you can’t do it, you’re not original enough, or that this wouldn’t work for you, just remember that there are 20 different people who thought that they could do bread better than everybody else.”

I thought about that meme several times this week, whenever that lack of confidence rears its head. 

I’ll tag you in that post. Rachel will enjoy seeing me share it with somebody else. She’s a fantastic person. She sings on LinkedIn! That’s a great way to stand out. I put my goats on LinkedIn. That’s how I stand out. 

Ashley: It’s random posts for me!

millennial entrepreneurship