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Courtesy of Afenya Montgomery

This Six-Figure Entrepreneur Encourages Women To Invest In Themselves & Their Dreams

"I always tell people that I never wanted to be an entrepreneur. It was more of a God-given assignment."

Money Talks

Money Talksis an xoNecole series where we talk candidly to real women about how they spend money, their relationship with money, and how they get it.

As we are out here getting to these coins, I want to ask you all something really quick. If you could write down the first idea that pops into your head, how much is it worth to you? And I am not talking about how much money you THINK people would pay for your idea. But how much money do you honestly believe your idea is worth right now? I ask this because a lot of times, as creatives, when we are coming up with ideas, we struggle with being confident in knowing how valuable they are. Now, no idea is too big or too small. But, with so many possibilities in the world with how you make a statement, it can get a little cloudy with believing that your idea can stand out among the rest.


I believe the trick is to not focus on how much faith you have in other people to buy in, but to focus on having faith in yourself. Do you believe in yourself? Do you believe your idea is valuable because you are valuable? You should always be confident in your capabilities first to really push forward your ideas/dreams. Your ideas are an extension of you, so they will always be pretty expensive. It doesn't matter how you came up with the idea or if you feel it has been done before. When you take a chance on your idea and stay determined to see it through, you are taking a chance on yourself. Every time.

This mindset is something I learned from six-figure entrepreneur Afenya Montgomery. Last year in 2020, I was able to attend an event at a coworking space where I connected with other women who were pursuing different businesses in different industries. It was so amazing listening to all their stories, especially the host, Afenya Montgomery. When we met, I knew we would stay in touch instantly. Now one year later, Afenya reminded me of how important investing in yourself is when it comes to entrepreneurship.

"I'm the kind of investor where I invest in myself and my ideas to watch them grow and flourish. I had this idea and I had to see it through. Nobody wants to look back years later and think, 'I should have done this or that.' I felt like if I was going to bet on anything, I was going to bet on myself. Always remember, when you are putting real money behind an idea, don't be in the talking stage or dating the idea. You have to be married to it."

Courtesy of Afenya Montgomery

Afenya Montgomery, born and raised on the south side of Chicago, started her professional career in the nursing field. Afenya was able to obtain her Master of Nursing degree and an MBA with a focus in executive leadership. In the year of 2017, Afenya felt that it was time for her to pivot. During that time, she started meeting up with her friends at local coffee shops and noticed that there was a lack of resources for people of color in entrepreneurship. That is all it took for Afenya to come up with an idea to help change that problem. Afenya mentions, "The idea began to form that it would be great to create a network of people that could act as accountability partners, potential business collaborators and resources for each other. Our first event was a panel discussion in June 2017 titled, 'Leveraging Your Network to Create Impact,' and we haven't looked back since."

Afenya is now the founder of The iCAN Collective. The iCAN Collective was founded on the pillars of Innovation, Collaboration, Accountability and Network. The iCAN Collective strives to give women a space to build a foundation of collaboration, authentic connections and support as they blaze new trails on the path of entrepreneurship or in their careers. This company is a collaborative coworking space for women of color entrepreneurs, creatives, and game-changers, where it offers memberships, exclusive events, networking opportunities, and brand packages. Afenya wants to be a resource for creative entrepreneurs and celebrate them for going after their dreams.

When you chase your dreams and execute them no matter what, nobody can tell you nothing.

In this installment of "Money Talks", xoNecole spoke with Afenya Montgomery about how trusting your gut, being strategic, and building your business at your own pace are the keys to creating financial freedom.

xoNecole: How much money do you make in a year? A month?

Afenya: I usually make mid-six figures with my company in a year. My revenue breaks down to making around $15-20K a month.

What do you define as “wealth” vs “success”?

Success for me means you are setting goals for yourself and getting them accomplished. You create these milestones for yourself and they can be small or big. Either way, you are getting them done. As far as wealth, wealth to me is being able to have certain things you want in your life, but more importantly, leaving something behind for your children and building that legacy.

What’s the lowest you’ve ever felt when it comes to your finances?

The lowest point for me was back before I was in nursing school. It was during the Great Recession and I got laid off. At the time, I was a newlywed, I had just bought a house, and I was about to have a baby. So that was when I started to look at money differently. I realized you can't only depend on a job. You need other ways in order to sustain money. I didn't think about entrepreneurship at that time honestly, so what I did was, I started a blog about my journey. Then, I looked at what I was passionate about, what careers aligned with that, and thought about how I can have more control over my money.

How important is investing to you?

I have always been interested in investing and how I can save money better. Even before my company, I would open money marketing accounts and make sure I was smart about utilizing what I had for the things I needed at the time. When it comes to investing, I think it is really important to know which type of investments are right for you. Because let's be real, it is not easy investing thousands of dollars or 500 dollars into something that you want([laughs). I'm the kind of investor where I invest in myself and my ideas to watch them grow and flourish. But it is important to have a diverse portfolio and that you are married to this investment/idea.

When it comes to structuring your business, what are your streams of revenue and how did you go about establishing them?

Prior to having a physical space, The iCAN Collective was about creating workshops and networking events/opportunities for women of color interested in entrepreneurship. I found myself having these events in different spaces and figured why not create a space that was permanent. From there, I wanted to provide different things that a lot of spaces do not offer. So with this space, we provide membership, a coworking atmosphere, host events or intimate gatherings, and we offer brand packages. It's important to have something that is unique and stands out from the rest.

What are some unhealthy habits about money or some unhealthy mindsets about money that you had to let go of to truly prosper?

The first thing I had to change was this mindset about money as if it will never come. My brother would tell me these affirmations stating, "Money is always free-flowing. I am abundant. Money will come my way, etc." Affirming to myself that money is always around me shifted my scarcity mindset. I think a lot of us think about money with this mindset and we cannot continue thinking, 'If I spend this amount or I go after this goal, I will never have money again.'

"Affirming to myself that money is always around me shifted my scarcity mindset. I think a lot of us think about money with this mindset and we cannot continue thinking, 'If I spend this amount or I go after this goal, I will never have money again.'"

Courtesy of Afenya Montgomery

What keeps you motivated? 

If you are passionate about something, then build the strategy behind what you want to do. I have heard people say that when it comes to business, do not go after your passion. But why passion is important to me is because that is honestly what keeps me going. If I don't have any interest or drive to be in that space, then I can't innovate in that space. Entrepreneurship is not one of those things where you're going to get a check just for showing up. You have to be really good at what you do and also have passion for it to see it flourish.

What is the most important lesson you’ve learned through being a businessowner?

It is important to be flexible and roll with the punches when you're an entrepreneur. But more importantly, my main lesson has been trusting your gut and trusting God. If God gave you an idea/mission, it is already protected by Him. I always tell people that I never wanted to be an entrepreneur. It was more of a God-given assignment and I have faith in what I am creating to be aligned with my purpose.

What was it like learning to expand your business from one city to multiple cities?

We are looking to expand The iCAN Collective to New York, which is funny because I actually wanted to move to New York when I was 18 years old (laughs). I am so in love with the vibe of New York and I also have family who live there. What I learned about creating a space in a new city is to always poll your people. It is really important to build relationships with the people in the community. I try to look at it through the lens of what I can I bring to this space to support the community the best way I can? I ask myself, what is the main need and what can I provide?

Was it easy to become a well-respected businesswoman in your respective industry or did it take time?

In the beginning, I was letting people know 'ya'll better put some respect on my name' (laughs). The thing about Chicago is that we are known to be a little cliquish. So it is not that I didn't know people in the industry, they just didn't know me. I won't lie, navigating through the industry was hard. I would go to a bunch of events, hand out my business cards, and network, network, network. But as time goes on, you realize that it is not about everyone knowing who you are, it is about the right people knowing who you are. You want to know the people who can speak your name in rooms that matter.

"As time goes on, you realize that it is not about everyone knowing who you are, it is about the right people knowing who you are. You want to know the people who can speak your name in rooms that matter."

Courtesy of Afenya Montgomery

What’s the best advice that you’ve received about finance during your first year of entrepreneurship?

The best advice I think that helped me during my first year is to build slowly. There is this misconception where you see people starting their businesses and everything is happening so fast, so you feel you have to catch up in a sense. But you really have to look at your strategy for your business, intentionally, in order to scale. Another really good piece of advice I received is that, a lot of people talk about an individual having multiple streams of income. But I don't think we talk enough about businesses having multiple streams of income. I have learned that it really helps to diversify what you provide in your business. If you are trying to be a million-dollar business, make sure that every move you make feeds that desire.

To learn more about Afenya, you can follow her on instagram @afenyabsn. You can also check out her business website here.

Featured image courtesy of Afenya Montgomery

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You may not know her by Elisabeth Ovesen – writer and host of the love, sex and relationships advice podcast Asking for a Friend. But you definitely know her other alter ego, Karrine Steffans, the New York Times best-selling author who lit up the literary and entertainment world when she released what she called a “tell some” memoir, Confessions of a Video Vixen.

Her 2005 barn-burning book gave an inside look at the seemingly glamorous world of being a video vixen in the ‘90s and early 2000s, and exposed the industry’s culture of abuse, intimidation, and misogyny years before the Me Too Movement hit the mainstream. Her follow-up books, The Vixen Diaries (2007) and The Vixen Manual: How To Find, Seduce And Keep The Man You Want (2009) all topped the New York Times best-seller list. After a long social media break, she's back. xoNecole caught up with Ovesen about the impact of her groundbreaking book, what life is like for her now, and why she was never “before her time”– everyone else was just late to the revolution.

xoNecole: Tell me about your new podcast Asking for a Friend with Elisabeth Ovesen and how that came about.

Elisabeth Ovesen: I have a friend who is over [at Blavity] and he just asked me if I wanted to do something with him. And that's just kinda how it happened. It wasn't like some big master plan. Somebody over there was like, “Hey, we need content. We want to do this podcast. Can you do it?” And I was like, “Sure.” And that's that. That was around the holidays and so we started working on it.

xoNecole: Your life and work seem incredibly different from when you first broke out on the scene. Can you talk a bit about the change in your career and how your life is now?

EO: Not that different. I mean my life is very different, of course, but my work isn't really that different. My life is different, of course, because I'm 43. My career started when I was in my 20s, so we're looking at almost 20 years since the beginning of my career. So, naturally life has changed a lot since then.

I don’t think my career has changed a whole lot – not as far as my writing is concerned, and my stream of consciousness with my writing, and my concerns and the subject matter hasn’t changed much. I've always written about interpersonal relationships, sexual shame, male ego fragility, respectability politics – things like that. I always put myself in the center of that to make those points, which I think were greatly missed when I first started writing. I think that society has changed quite a bit. People are more aware. People tell me a lot that I have always been “before my time.” I was writing about things before other people were talking about that; I was concerned about things before my generation seemed to be concerned about things. I wasn't “before my time.” I think it just seems that way to people who are late to the revolution, you know what I mean?

I retired from publishing in 2015, which was always the plan to do 10 years and retire. I was retired from my pen name and just from the business in general in 2015, I could focus on my business, my education and other things, my family. I came back to writing in 2020 over at Medium. The same friend that got me into the podcast, actually as the vice president of content over at Medium and was like, “Hey, we need some content.” I guess I’m his go-to content creator.

xoNecole: Can you expound on why you went back to your birth name versus your stage name?

EO: No, it was nothing to expound upon. I mean, writers have pen names. That’s like asking Diddy, why did he go by Sean? I didn't go back. I've always used that. Nobody was paying attention. I've never not been myself. Karrine Steffans wrote a certain kind of book for a certain kind of audience. She was invented for the urban audience, particularly. She was never meant to live more than 10 years. I have other pen names as well. I write under several names. So, the other ones are just nobody's business right now. Different pen names write different things. And Elisabeth isn’t my real name either. So you'll never know who I really am and you’ll never know what my real name is, because part of being a writer is, for me at least, keeping some sort of anonymity. Anything I do in entertainment is going to amass quite a bit because who I am as a person in my private life isn't the same a lot of times as who I am publicly.

xoNecole: I want to go back to when you published Confessions of a Video Vixen. We are now in this time where people are reevaluating how the media mistreated women in the spotlight in the 2000s, namely women like Britney Spears. So I’d be interested to hear how you feel about that period of your life and how you were treated by the media?

EO: What I said earlier. I think that much of society has evolved quite a bit. When you look back at that time, it was actually shocking how old-fashioned the thinking still was. How women were still treated and how they're still treated now. I mean, it hasn't changed completely. I think that especially for the audience, I think it was shocking for them to see a woman – a woman of color – not be sexually ashamed.

I hate being like other people. I don't want to do what anyone else is doing. I can't conform. I will not conform. I think in 2005 when Confessions was published, that attitude, especially about sex, was very upsetting. Number one, it was upsetting to the men, especially within urban and hip-hop culture, which is built on misogyny and thrives off of it to this day. And the women who protect these men, I think, you know, addressing a demographic that is rooted in trauma that is rooted in sexual shame, trauma, slavery of all kinds, including slavery of the mind – I think it triggered a lot of people to see a Black woman be free in this way.

I think it said a lot about the people who were upset by it. And then there were some in “crossover media,” a lot of white folks were upset too, not gonna lie. But to see it from Black women – Tyra Banks was really upset [when she interviewed me about Confessions in 2005]. Oprah wasn't mad [when she interviewed me]. As long as Oprah wasn’t mad, I was good. I didn't care what anybody else had to say. Oprah was amazing. So, watching Black women defend men, and Black women who had a platform, defend the sexual blackmailing of men: “If you don't do this with me, you won't get this job”; “If you don't do this in my trailer, you're going to have to leave the set”– these are things that I dealt with.

I just happened to be the kind of woman who, because I was a single mother raising my child all by myself and never got any help at all – which I still don't. Like, I'm 24 in college – not a cheap college either – one of the best colleges in the country, and I'm still taking care of him all by myself as a 21-year-old, 20-year-old, young, single mother with no family and no support – I wasn’t about to say no to something that could help me feed my son for a month or two or three.

xoNecole: We are in this post-Me Too climate where women in Hollywood have come forward to talk about the powerful men who have abused them. In the music industry in particular, it seems nearly impossible for any substantive change or movement to take place within music. It's only now after three decades of allegations that R. Kelly has finally been convicted and other men like Russell Simmons continue to roam free despite the multiple allegations against him. Why do you think it's hard for the music industry to face its reckoning?

EO: That's not the music industry, that's urban music. That’s just Black folks who make music and nobody cares about that. That's the thing; nobody cares...Nobody cares. It's not the music industry. It's just an "urban" thing. And when I say "urban," I say that in quotations. Literally, it’s a Black thing, where nobody gives a shit what Black people do to Black people. And Russell didn't go on unchecked, he just had enough money to keep it quiet. But you know, anytime you're dealing with Black women being disrespected, especially by Black men, nobody gives a shit.

And Black people don't police themselves so it doesn't matter. Why should anybody care? And Black women don't care. They'll buy an R. Kelly album right now. They’ll stream that shit right now. They don’t care. So, nobody cares. Nobody cares. And if you're not going to police yourself, then nobody's ever going to care.

xoNecole: Do you have any regrets about anything you wrote or perhaps something you may have omitted?

EO: Absolutely not. No. There's nothing that I wish I would've gone back and said to myself, no. I don’t think at 20-something years old, I'm supposed to understand every little thing. I don't think the 20-something-year-old woman is supposed to understand the world and know exactly what she's doing. I think that one of my biggest regrets, which isn't my regret, but a regret, is that I didn't have better parents. Because a 20-something only knows what she knows based on what she’s seen and what she’s been taught and what she’s told. I had shitty parents and a horrible family. Just terrible. These people had no business having children. None of them. And a lot of our families are like that. And we may pass down those familial curses.

*This interview has been edited and condensed

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Feature image courtesy of Elisabeth Ovesen

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