The financial services industry is notorious for its intransigent barriers to entry and overwhelming complexity. Financial wellness and wealth are a cornerstone of overall health and happiness. Having the power to control your destiny in those areas allows for increased economic freedoms attributed to many factors, from social and economic mobility to better mental health, reduced stress, etc.
Dana Wilson is the Founder & CEO of Changing How Individuals Prosper (CHIP), a B2B financial services marketplace that makes finding Black and Latinx financial professionals easy. After being the only Black woman in the financial industry for over 15 years, she wanted to make the financial journey for Black and Brown individuals accessible. Her mission is to rebuild the economic trust factor.
Dana said, "I don't think the industry hasn't reflected the Black and Brown communities. We haven't felt wealth was synonymous with us and our families in building that type of generational wealth. In understanding, not only all of the products and different things are available but also the fact that there's a professional that looks like me, who might better understand my journey.
I don't have to walk into a room and feel like I have to learn a bunch of stuff or worry about somebody judging me or, hey, maybe I am making six figures. Still, I should know more and feel like this person might stereotype me based on how I look, talk, or dress at this moment, but not really knowing more about me."
What's the biggest fear you had during your business journey?
Dana had a different perspective on what her biggest fear was. She said, "The biggest fear is that it does not exist because when it does not exist, it continues to show people in the industry that Black and Brown individuals may not matter from a financial inclusivity perspective, that our dollars are not important for changing the economics within society.
The biggest fear is not having these types of platforms like CHIP in the world and not being able to let people know that, hey, you belong. You should be able to build your generational wealth in the way that you want to.
You can start to redefine words like wealth—like what you want your generational landscape to look like and how you can become your own financial architect. If companies like mine or my company do not exist, that's a very scary thing for me to think about."
Tell us about a major setback you had in your business and how did you recover?
Like many entrepreneurs, Dana echoes the sentiment of feeling like she's not doing enough. She's learning to balance accepting the pace of change and refocusing as her business shifts. Dana is learning that not everything will be perfect, and in the process, she's learning to get out of her own way.
What's the biggest risk you've taken in your life thus far?
Dana admitted her biggest fear was publicly failing. That took her a long time to process and reframe. She said, "Every day is a risk. I don't know what normal is. I don't know what life looks like without taking risks. I also think it's just a redefining of what risk is. So for me, it's not like a defining negative word, same as fear. It just propels me further to do the greater work that I want to do."
What are you most proud of when it comes to CHIP?
Being a solopreneur gets lonely for Dana, but she's most proud of the community and the support she receives. She said, "The community support for me is something that I'm just super proud of because those are the things that keep me pushing as a founder, knowing that this is extremely important, not just to other professionals in the industry who have felt like their voices have been ignored, or their faces haven't been seen, but also to the consumers who will just feel like, I can do this.
I could have what I have from a financial perspective, and I can actually get to this next step, and I can actually get to that goal, which changes the lives of so many others after them and their current life and their family."
Describe what it was like preparing for the pitch competition.
This was Dana's first official pitch competition. She said, "It was amazing standing on that stage, standing in that room to be able to share what we're building with people who haven't heard it before was just—it was truly a high, one of my highlights of the year. So there's definitely that preparation that goes into it. It's not just jumping on stage and you just start talking. It was scripted out. I practiced it.
And then, you get to a point where you just go out on stage, and you perform. And being able to share your passion with people, see the head nods, look into their eyes, and know that they get it. So it was exciting."
When it came down to crowdfunding, Dana relied on her community for support. She only had a weekend and a few days to campaign for votes, and her community asked her how they could help. But Dana is also very competitive. She glued herself to her computer until she connected with her entire network.
Dana's advice to those who are looking to pitch is, "Start early." She says to start early pitching and start early crowdfunding for the votes. She said, "Be aggressive, and don't give up."
CHIP plans to use the pitch funds to up-level the next generation of their technology in addition to marketing.
Support is not always given to Black and Brown women in business. When has this disappointed you the most?
Dana was candid with her experiences as a Black woman in business. She said, "I think it's just all of the promises. There are still a lot of promises of just money and things and stuff being out there. And yet you still see it not really going to Black and Brown businesses. It's like maybe it's trickling in, and it's always like the first thing people just stop doing when the money and things start to change, right?
We're the first cutoff, and it's just like, why? And what message is that truly sending? So I think for me, That's the thing that disappoints me more of the promises or people saying that, Hey, I don't know where to find Black and Brown businesses or Black and Brown services to support and things like that."
What's the most critical lesson you've learned about business?
Dana said, "I know that sounds very cliche, and people say that all the time, but I think over the years of just my life in general, a lot of people have really poured into me, and people say they see things in you and all those other stuff, and you're just like, okay, you know, great, thank you.
And you believe it, and you're extremely confident, but you still have to, like truly, dig deep and own that confidence. And for me, that has been the biggest thing. That was the change for me. And it also helped throughout my EMBA program with my cohort specifically, who helped me to dig deeper into that for myself in various ways.
Once you can just put that belief in yourself and truly step fully into all that confidence, it's game-changing. It changes the way you think about your business. It changes the way you scale your business.
It changes your ability to be a leader and what that word means to you, what it means not just to lead a team, what it means to lead your consumers, your partners—the fact that you truly can think that you can change the world or industry or whatever that thing is. But you have to really, really believe it. Like to the point of crazy where it's like, of course, I'm going to do that like I can do that."
What do you think is an important skill or asset you need to be successful in business?
Dana believes entrepreneurs have to have empathy. She said, "You have to have empathy: empathy and humility. But empathy is more important because it's something that people try to avoid or they avoid different circumstances in life that can make them great. And those could be avoiding risk or avoiding problems, or avoiding conflict.
But I think when you are a person who is a human who dives into your full authenticity, who you are and can be very respectful of other people, their values, and who they are in their full selves—and you have also gone through some stuff yourself like you become a lot more empathetic. And without a certain level of empathy, it's hard to really build things. It's hard to get people to believe. It's hard to actually listen and really listen and hear people without all of the noise and all of the stereotypes, and all of the biases.
But being able to have that level of empathy and care is a game changer, and not everyone, unfortunately, embraces that in a way that would make them a great leader or a great business person."
What's the most exciting part of your business?
Dana genuinely loves building partnerships with other professionals in the financial industry and being able to support their business by bringing more clients to them. She said, "We're able to support each other and build partnerships to make revenue and help all of our companies grow.
So for me, that's really exciting because that's a whole other wheelhouse of where we build generational wealth and revenue for ourselves just as founders and entrepreneurs are how we can go back in and support each other. So it's like all the things that we're looking forward to doing for consumers, we are doing with each other through partnerships."
What do you think the future holds for Black women entrepreneurs and small business owners?
Dana said, "I think it looks like money. It looks like our future is bright. I mean, it is. It is bright. It is green. It is powerful. And it's a time like it's just time. I do think sometimes timing is everything, and it's our time where we're just supporting each other, we're collaborating, and we're doing it in a way that's putting money into everyone's pocket. So, yeah, that's really what we're doing. There is no stopping us."
If you and I were meeting 3 years from now, looking back, what would it take for you to feel over the moon about your progress?
Dana imagines that CHIP will be solidified in the market and has taken a global stance. The financial gap exists in more than just the United States. She believes it's a global problem. She envisions touching many lives with CHIP's reach and that the money continues circulating the Black and Brown community. Dana sees that the professionals she works with have grown their practices into millions of dollars, which will trickle down into the rest of the community. Lastly, CHIP will be able to participate in large fundraising rounds that continue to help it scale.
Being a business owner is a tough job. How do you take care of yourself?
Dana makes her mental health a priority by regularly going to the gym. She sees a therapist and an executive coach. Dana meditates and rests by taking naps. She never forces herself to work if she can't focus. Dana steps away and engages in other activities, even watching TV, without guilt. She implements boundaries like saying no, which keeps her balanced.
What is your favorite quote or mantra?
Eleanor Roosevelt, "Believe in yourself. You gain strength, courage, and confidence by every experience in which you stop to look fear in the face. You must do that, which you think you cannot do."
What book and podcast would you recommend?
Book: The Everyday Hero Manifesto: Activate Your Positivity, Maximize Your Productivity, Serve The World by Robin Sharma.
Podcast: Your First Million with Arlan Hamilton, Small Doses with Amanda Seales, Therapy for Black Girls with Dr. Joy Harden Bradford, and WorkLife with Adam Grant.
What's your favorite business hack or app you can't live without?
Notion.
Name one food item you have a hard time saying no to.
Chocolate chip cookies.
What's next for CHIP?
CHIP is focused on partnerships, specifically with FINTECH companies. They have plans to scale their technology to support their customers and their team better.
Any last words…
Dana said, "I would inspire anyone to pick a word for the year. My word for the year was resilience.
And if I have to really reflect, I'm still reflecting now. Still, that word and setting my eyes on it and what it means literally catapulted everything that has happened this year personally and professionally, as you name it.
There is something about picking a word for the year, and redefining it in ways that will suit you, keep you motivated and inspired, and keep you focused.
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