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Entrepreneurship isn’t just about success—it’s about failing, learning, and pivoting. In this episode, Ifeoma Ike and Dr. Kelly Burton get real about the challenges of building a business, from how the wrong team can cost you everything to the financial mistakes and tax pitfalls that trip up entrepreneurs. They break down the emotional toll of entrepreneurship while sharing the hard-earned lessons no one talks about. If you’re thinking about starting a business or already in the game, this episode is a must-listen. Tune in now!
How are you?
I’m wonderful. How are you?
I’m great. How are you feeling?
I’m feeling great.
Recognizing The Right Moment To Become An Entrepreneur
We’ve done a couple of seasons and had a lot of amazing guests but we haven’t dived into our own entrepreneurial journeys, and they’re quite long. I have a couple of questions that could help give some people some insights so that they know that we know what the fuck we’re talking about, have raised a little money here or there, and have done a little bit of something here or there. My first question to you is how did you know that it was right to be an entrepreneur? It’s not that you wanted to be, but that it was right. Were there conditions that told you it was right to be an entrepreneur? Did something pop off? What happened?
I happened. I’m bossy.
It’s good to know. You knew you could be a boss. To be clear, everybody shouldn’t have an LLC.
Most people should not have an LLC because people don’t understand how hard it is to run a business. A lot of it is romanticized but it’s hard. There are certain core ways of being that need to be in place in order for you to be able to be successful. How did you know it was right to be? When did you know it was right to be?
I didn’t know that it was right to be but I always had a side hustle. In a lot of ways, my entry into entrepreneurship was seeing my dad and my uncles always having to have something on the side while they had their full-time jobs and then also recognizing how I felt working in spaces. I didn’t necessarily have bad traditional work experiences but there were times when I felt like, “Is this it? Can I do this for twenty years? Can I do this for 30 years?”
I knew about myself that I liked change. That allowed me to be more creative. That’s how I started. I want to talk a little bit about these humble beginnings a bit as to how we started. When I was in grad school, I was helping people with resumes and their grad school admissions to medical school, law school, or whatever. My little firm was called HYPE, Helping You Professionally Excel.
That’s so you. That’s so on-brand.
This is when we had word art and stuff. This was pre-Canva. I was doing presentations. I was doing it. What I also realized was that I didn’t have the language then but I was excited about generating customers, meeting people, hearing what their needs were, and trying to figure out a solution. I had no idea I was a problem solver at that time.
It started off with resumes and writing because my comfortable place was words. It then got into presentation. I was like, “Let’s work on your pitch. Let’s work on how you show up. Pretend I’m the grumpy person at the job. Try to sell me.” I was always ear-hustling. I was hearing that people were like, “I need to get this done,” and I would think, “What about my skills could help them produce something that can solve that problem?” It was getting connected to what I liked to do and what I could produce that was viable or worthwhile to a client. That’s how I started playing and tinkering around with where I’m at. It was back in 2004 or so when I was playing around with the small stuff first. What about you?
I had played in entrepreneurship earlier, but for me, my entree was 2004 or 2005 because I was in graduate school. I was at Emory. It was fully funded but you weren’t supposed to have a full-time job. You are supposed to focus on your academics. I had to pick up some side gigs because I had a little stipend but it was $12,000 a year or something. You can’t live off of that. It was student loans or consulting.
I’m sorry. I did the division. Is that $1,000 a month?
Yes.
I wanted to make sure that the counting was right.
That doesn’t add up, right? I remember I got a gig with NeighborWorks America. My beginnings are in community development and community building. They wanted me to come in and do training. They always had these trainings and I was excited. It said, “$40 an hour,” and I was like “$40 an hour?” It was money to prepare the curriculum and to train. I was like, “It adds up to about $2,400 or $1,800.” I was like, “Oh snap.”
Hardest Lessons On The Entrepreneurial Journey
No one tells you you are supposed to get all your taxes, your retirement, and all the things. Those are the lessons you learn. You’re thinking it’s a wage. You’re thinking it’s a $40-an-hour wage. That’s not what it is. For me, it opened me up to the possibility of working for myself in a different kind of way. I was like, “I got options here. I can make a living with myself.” That was my introduction. What would you say was the hardest lesson that you have learned as an entrepreneur?
One of the hardest lessons around entrepreneurship is that it is possible that with the wrong team, you can lose your business.
That’s real.
Teams matter in entrepreneurship. I don’t think that I was prepared for not just the mourning of losing something like your business, whether it’s your IP, the direction of the way the company is going, or the way that you sometimes build with friends and then that goes awry. There were a lot of different things to mourn there but I don’t think I recognized that I needed support and that that is a form of grief that in many ways can require professional help or support.
I got myself a coach to help me prepare for the next thing because my fear or my response to that was, “I got to create the next thing. I’ve got to create a space to work.” Also, it felt like, “I’m going to create the space and it’s going to be the space that does all the things right that the other place didn’t do.” This coach sat me down and was like, “Have you given yourself enough time to put that to rest, rage, and get all of that out?”
She also put it down to brass tacks like, “Can you afford to? Is there a way that you can work in something not connected to your expertise to give yourself room?” There are a lot of hard lessons. As Paul said in The Good Book, “I’ve been rich and I’ve been poor.” There’s always going to be money and what have you. I wish I had gotten a little bit of the advisory sticker around some things to consider not only when you’re building a business but also when you exit some ways that you need to check in on your wellness and your health before you do anything else. What about you?
What you shared is so spot on because the culture of social media generally projects entrepreneurship as a solo endeavor like it’s the hero image but it’s the team. Entrepreneurship is about your ability to build a team. That’s spot on. My hardest lesson has been entrepreneurship is more about failing than it’s about winning. It’s more about failing than it is about succeeding. If you don’t have an appetite for that or you don’t have a muscle or are not committed to building a muscle to constantly be failing, you’re not going to be a good entrepreneur. That’s what I’ve learned.
We have both launched multiple ventures. I tease that I have launched a business in every type of entity, like a for-profit service base, a for-profit product base, a nonprofit, and a social enterprise. Pick a lane and I have started something in it. Much of entrepreneurship is counterintuitive. You think you know but you don’t know. Unless you have the humility to go into it knowing, “I probably don’t know what I’m doing,” then you’re going to screw it up. That’s what I have learned as a person.
You have to be an egomaniac a little bit to be an entrepreneur because you have to be a little crazy. Especially when you come at it again and again, you’re going against the odds. You have to balance that ego with humility to understand and appreciate, “I’m going to go for this. I’m going to believe that it’s going to accomplish all the things but there’s a good chance that it won’t. How can I go with my eyes wide open so that I’m able to mitigate my Ls?” You’re going to take some Ls. The last thing I’ll say about that is every level of growth is a new bombardment of Ls.
If you remember that, can you repeat that, please?
They say, “Every level, new devil,” but every level, new fail. It looks different. It comes in different. You think you are coming out at that last level but then you get to that level and you are gut-punched.
Entrepreneurship Realities On Taxes, Teamwork, And Business Stability
Let me tell you something. I speak to my accountant a lot. That’s another thing I didn’t know when I first started. Get your ass an accountant and a lawyer. There was one year we were doing well. We were about to take on another client at the end of that year. It was maybe in quarter four, November. She contacted me and said, “You could take that but I want to show you some figures.” She showed me the figures of how that was going to impact taxes.
To your point, the conversation that is often discussed is about profit. Especially for consultants, I had one friend who was like, “You never turn down a client. You keep taking. If you need to delegate it to other people, then do that.” I understand the logic of that but you’re not always ready to take big money. She said that and I had to go back to the table and was like, “How about March of next year?” That happens. This happened to be a different type of year.
I’m even feeling a lighter lift in having this conversation with you. I don’t know if I’ve shared with folks that there have been some years where we’ve chosen not to be as profitable because of a whole range of mitigating circumstances. It is that type of insight. You need a team, whether they’re part of your team or they’re hired consultants, and you need people who think smarter than you so that you can stay afloat. Sometimes, you learn that the hard way. I never thought especially as a poor kid growing up that I was going to turn down a check. What was coming to my mind was, “You are turning down a check,” and she was like, “I’m trying to get you in check.”
To give you some sense of the trade-offs. I had someone who I love very much who tunes in to the show. They called me and were like, “I’m calling you because you’re the only person that will get this. I paid all of my taxes on time with no payment plan because I planned last year and created a whole separate account for my taxes.” I clapped for her because, for so many of us, it takes ten, fifteen, or twenty years into the game before you can have that conversation because, for the first 5 or 7 years, you aren’t paying them.
Nobody told you you are supposed to be paying them and then you’re like, “Where did this tax bill come from?” You get your act together and you’re like, “I know I got to pay them but I’m going to get an extension,” or, “I’m going to pay them on the backend.” It’s about north of ten years before you have some systems to get ahead of the game. Nobody tells you this.
That second bank account will keep you free for some days. Don’t get tempted. That bank account on days will have more money than your operating line. Don’t touch it.
Leave it alone. We go into entrepreneurship thinking, “I want a refund check.” It is a mindset shift. There is no more research. There are no more refund checks. There are tax bills. That’s it.
Here’s also another tip. I love this. If you can speak with your accountant, speak with your lawyer, or speak with the person who helped you form your business, become an employee of your business.
It’s also a long time. You can get to that because you are taking the shareholder drafts. You are deducting and thinking, “I’ll deposit or transfer.” These are all of the things.
Become an employee. Let your company pay you what your rate is consistently. You never know when you’re going to want to make a purchase. I have pay stubs from my company that allow me to show that it is a good business and a standing business. These are the things that you don’t think about. Speaking of that other team that I had to leave, I was a couple of months shy of being a co-founder of that space for three years. I took some time off and then went and started my new company.
I was looking at my account and was like, “I want to look at potentially buying a house.” I went there and was asking all these questions at the credit union and they were like, “You started this business.” Due to relationships, I had all these contracts. There was money in the bank. I was like, “We’re fluid.” They were like, “Your business is only six months in formation. I felt insulted. I was like, “Did you not hear that I created Helping You Professionally Excel? I am a seasoned professional.” I’m going in like, “What’s the problem?”
I didn’t know enough that she was like, “The way the bank looks at it is if something happens to this business tomorrow, what does that mean for you as an employee of that business? Since this is your business, when that tanks, you tank in the eyes of the bank.” She was like, “It looks like that if you would’ve stayed at the other business that you had founded, then there would’ve been no problem.” I was like, “Don’t try something. The devil is a liar. They’re both my businesses. There’s nothing I can do about that.” I felt so depleted.
I’m sharing this story because I promise you, I’m not going to lie to you. There have been times when I was like, “I got to get out of this entrepreneurial game because this thing is not giving me the type of stability, especially as a woman because of the way the laws are set up.” She was telling me that if I was a manager at McDonald’s, Gap, or whatever, there was more security that the banks would look at me having than having my own business. Nobody told me that it wasn’t about how much money was in the bank or how long I’d been a professional. I didn’t know that. I found that out the hard way. Had I known, I would’ve tried to get the house first.
Leveraging Entrepreneurial Spirit And Innovation In Today’s World
It goes back to that point. That comes out of nowhere. You’re like, “If only I had known.” That is why communities like BIA and the communities created by our member organizations matter so much because sometimes when there is a major pitfall or fork in the road, the difference is some advice from somebody who has been there and done that. As we wrap up, let’s talk a little bit about how we leverage our entrepreneurial spirit in this moment. What does that look like given the state of affairs for us as a community of Black entrepreneurs?
The great thing about an entrepreneurial spirit is that even if you work at a traditional space where somebody else is cutting their check to you, you are still an innovator. You still have ideas around solving problems. You possibly also have thought about a business model. At this time, I love thinking back to Issa Rae’s dream map of the different entities that she felt would come from her humble beginnings of creating Issa Rae Productions and what that could produce from this YouTube channel and all the different worlds.
I believe in world-building. Words build worlds. Anything that’s going to be revolutionary starts with a vision. People who have an entrepreneurial spirit should give themselves some visioning time. All things well and considered because I want you well and I want you to know that you’re going to also have good moments while you’re an entrepreneur, what is it you’re trying to build? What is it that you’re trying to solve? It doesn’t have to be a social impact endeavor. If you’re trying to solve for your own stability, wealth creation, or resources for your family, write those things out.
Whether it’s in leaving and creating something separate like a side hustle or even reimagining your role in that position, who you are is not going to come from an employer. It’s going to come from you being able to stress to the world, the universe, and those spaces, “This is who I am, and this is how you get the best out of me.”
I love that the Black Innovation Alliance recognizes that the advice around innovation and entrepreneurship is not just for people with LLCs. It’s for all of us. It’s about us giving ourselves time to tap into that spirit because that spirit is your unique ID print. That is the thing that makes you different from the next person. That’s my thought around what we should be doing more at this time. What about you?
I go back to the idea of the right to innovate. What does innovation look like in your life? Oftentimes when there are things happening in the world that we don’t have any control over, we feel completely without agency and without power, but you can change the things in your life. How do you innovate your life? How do you innovate your behaviors? How do you innovate your environment? How do you innovate in your relationships? How do you refresh, renew, restore, and redirect? What does that look like? A lot of us can use some innovation in our lives. How do you start home and then allow that to ripple out? That’s how I think about it.
Why did you end there? The way you need to reimagine space and relationship with others. Shout out to the introvert. Sometimes, that’s a relationship with yourself. There isn’t anything worse than meeting an unhappy entrepreneur. It’s a lot. It’s always unhappy. I’m not talking about a season or whatever. It’s like, “You’re doing great. You’re doing this,” and it feels like the satisfaction isn’t there. When you said, “Innovate your lives,” know you have the power to reinvest, reimagine, and then declare because you do have the right to innovate.
We have the right to innovate in all the things.
Since I started this thing, I’ve got to wrap it. We are so excited that you all joined us for this episode of the show. We would love to hear from you. What are the ways that you are trying to innovate your entrepreneurial experience and how you’re trying to activate your entrepreneurial spirit? We would love to hear what your stories were. What was your first job? What was your first gig? What was your first paycheck? We would love to hear good stories and bad stories.
We are building a community of innovators and creatives who need spaces like this to be able to be truthful about that experience. We want to hear from you. Download this, share this, and follow us on all the social outlets. Please make sure that you leave us a review. With that, we thank you for joining. We hope to see you again. Take care.
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