Big dreams and goals have almost become prerequisites to building a successful business. But, taking leaps to chase those dreams shouldn’t happen at the spur of the moment; it needs preparation and support. You need to be equipped to deal with the barriers and challenges that entrepreneurship life will constantly throw at you.
In this episode of Unlearn Lab, Alyssa Hall shares her journey to becoming an entrepreneur. She explores the hardships of growing a business that no one seems to talk about — but is what we really should be talking about if we want to achieve greater success in our businesses. Alyssa also discusses the barriers we need to overcome for our business to thrive. Then, she shares how she redefined her own success and wealth as an entrepreneur, a mother, and a woman.
If you want to learn about the struggles of being an entrepreneur and how you can rise above them, this episode is for you!
Here are three reasons why you should listen to this episode:
- Explore the difficult side of entrepreneurship that no one talks about.
- Discover how to break down barriers in entrepreneurship and be empowered.
- Learn what success and generational wealth mean to Alyssa.
- Connect with Alyssa: Email | Instagram | LinkedIn | Facebook | Website
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[02:38] How Alyssa Became An Entrepreneur
- In late 2018, she bought her own domain and became a single mom.
- Becoming an entrepreneur seemed like the most realistic way to survive with her daughter.
- Six months into entrepreneurship, she quit her nine-to-five because she seldom saw her daughter, which was painful for her.
- If you quit your job unprepared, it won’t be easy.
[07:08] The Hardships Of Being An Entrepreneur
- She got good tax returns, which made her feel secure enough to quit her job and focus on building her business.
- The child support agreement also included her daughter’s dad paying for her rent.
- With around $6000, she was able to coast for a few months.
- When her lease was about to end, things started getting difficult even if she had a solid support system; ultimately, she ended up having to move in with a family member.
[13:46] Defining Success
- When she entered a group coaching program filled with moms, she felt angry and bitter that everyone just wanted to make extra money, while she, on the other hand, was barely trying to survive.
- She felt guilty that she wasn’t financially prepared to provide for her daughter.
- For her, success means providing her daughter with the life she deserves.
[19:57] Breaking Barriers in Entrepreneurship
- People often end up glamorizing numbers rather than thinking about sustainability.
- She despised asking for help but realized that we could only break through barriers that hold us back and become empowered if we lean on our resources.
- Know when you need help, and don’t hesitate to ask for it.
[25:23] Struggling with Generational Wealth and Identity
- She couldn’t grasp the concept of generational wealth.
- Eventually, she came to the conclusion that generation wealth is freedom of options.
- She wants to give her daughter that flexibility that we should be afforded.
- Because of her different identities, she fits into so many boxes yet doesn’t fit perfectly.
- She used to feel like she had to prove herself, but now she doesn’t conform to anyone else’s description of her.
[29:57] Unlearning Professionalism
- The biggest thing she’s trying to unlearn right now is professionalism.
- She always strived to look professional, but the pandemic has propelled her to change what professionalism means to her.
- However, she’s also balancing being herself and how she must appear in corporate spaces.
Alyssa Hall is an anti-racism consultant and executive coach. Upon completing her training at the Institute for Professional Excellence in Coaching (iPEC), she began her journey of coaching corporate leaders and business owners on mindset and leadership. She now uses those same skills to work with coaches and other service providers to become active in the anti-racist movement.
Her main area of focus is strengthening the leadership skills needed in promoting an anti-racist environment. In addition, she ensures her clients continually uphold their values of diversity, equity, and inclusivity, which in turn brings them greater success in their lives and their businesses.
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I felt like I was never black enough. I felt like I was never Hispanic enough. I felt like I was never — I had to prove that I was an actual gamer. I have to prove all of these different things that I hold close to my identity to now where I am where I’m just like, “I’m never going to fit into whatever someone else’s description of me is, but I’m just going to exist in it in a way that feels really, really good, and instead, change their perception of what that looks like.”
Jess Moy: Welcome to Unlearn Lab with me, your host, Jess Moy. Together, we’re going to demystify what culture really means nowadays, and how we can show up as our whole-ass human self through the lens of wellness, entrepreneurship, and impact. Really thriving, in the long run, requires you to remember who you really are. Unplug from the matrix, and write your own damn story. We are going to cover some serious ground together y’all.
From what culture really means, to unpacking modern-day spirituality, to peeling back the layers of multi-passionate entrepreneurship — we are going to explore it all together. Let’s unlearn some shit.
Alright, welcome, welcome, welcome back to Unlearn Lab with me, Jess Moy. We are here with my biz bestie and also amazing human, Alyssa Hall, who is an anti-racism consultant and leadership coach. We are just going to dive right in. Welcome to the show and to my little online space on the interwebs. I wanted to start off with your story. This is what Unlearn Lab is about — us making the experts that we know and love, and bringing it down to the human level. Let’s talk about it.
In your journey, you entered into the coaching space. I want to know why you became an entrepreneur and what motivated you to enter this industry at a time that’s kind of unprecedented, right? You entered into 2020, and we all know what happened then. Tell us about it.
Alyssa Hall: Right before we got on — and actually like a couple of weeks ago, we spoke about the typical story surrounding people entering entrepreneurship and what that looks like. For me, it was definitely out of necessity. I officially became an entrepreneur in late 2018. That was like the day where I bought my first domain, I was so excited.
But a few months prior to that, I had just become a single mom. For me, entrepreneurship felt like the most realistic way to be able to just survive with my daughter alone and also living in New York City. At the time, I was like working either in a doctor’s office or in a restaurant, or just like switching back and forth. The most that I was making was like $20 to $22 an hour, which is nowhere near enough for a single mom.
Jess: I think it’s interesting that you mentioned this idea of entering entrepreneurship as a necessity, which is — when we spoke about that, it was such an “aha” moment because, at least in the coaching industry that we’re in and the online digital entrepreneurship space, everything looks so fuzzy, and bright, and through a rose-colored lens, and you’re like, “I’m just going to quit my nine to five and pop into this new arena, and make $10 million tomorrow.”
Alyssa: That piece alone — that, “I’m going to quit my nine to five.” I had a moment where I did the, “I’m going to quit my nine to five”, and even that was out of necessity. That was six months into being an entrepreneur, and the job that I was working made it so difficult for me to see my daughter. I only saw her on the weekends, and her dad would take her Monday through Friday. That was the most painful time of my life — also, the most painful time of my parenting life. But also, it really pushed me to actually make this work.
Then, one morning when her dad came to pick her up, I just broke down. I was like, “I can’t do this anymore. I can’t do this whole, ‘not seeing her for five days and trying to work on this business.’ I’m just going to quit today and attempt to work on this business.” It wasn’t all sunshine and roses — that’s another thing that people don’t talk about. When you quit the nine to five, if you’re not appropriately prepared, it’s not always sunshine and roses.
Jess: Let’s talk about that preparation a little bit because I was in a very similar space where I quit my job out of necessity for my mental well-being. At the time, the rhetoric around quitting your job was, “If you don’t take a risk”, or “If you don’t bet on yourself — those are the people that make it.” I think this culture of entrepreneurship is a little bit misleading because we are not seeing the back end of what was the structure, what was the support system that people already had in place before they took the jump.
I think there’s a difference between taking the jump off of a cliff with no parachute and just — I don’t know — leaving it up to God, or source, or who you identify with, being like, “I hope that I make it down”. You’re like, “What scenario would that ever work?” versus people that say, “Take the jump”. But you don’t see that they have a parachute on their back, maybe like a thing to catch them on the bottom — we don’t see that.
Let’s talk about the preparation that you had, and maybe the preparation that you wish you knew or had if you could do it all over again. No regrets, right? No regrets, but hindsight 2020 a little.
Alyssa: Yes. Oh, I love this question because I feel like I am easily used for people as like, “She’s a black single mom. Look at her, she’s the poster child of, “You can do it”. I’m like, “Y’all have no clue.” First of all, the structures that I did not have, and the structures that I actually did have. At the time that I quit my job, it was literally right after tax season. If you have children, or if you’re still paying for school, we actually get a good tax return. I got a really good tax return.
I had just gotten paid like two days before, so I got that bi-weekly check. I had money that was just — not just sitting there, but it was there for me to visually see and feel comfortable with. I was like, “Okay, cool. I’m just going to make this business work. At the time, the child support agreement that I was doing with her dad was that he was paying for my rent. That’s a huge ass bill that was not even in my brain.
I was able to take those $4,000, $5,000, $6,000, and really coast for a few months. As the months went by, and as we got closer to, “Oh, my lease is about to end. I need to figure out what I’m going to do.”, that’s when things started getting hard. Although I had that support from my daughter’s father, who is one of the big reasons why I’m actually even able to do all the things I am today because of the way that he supported. He would take off of work if he knew that I had a networking event to go so that he could take my daughter, and I could just like stay out all night, and then pick her up at his house in the morning.
He would do so much that — me watching my mom who was also a single mom, she didn’t have that. It was the regular every other weekend, “Whatever happens in between that time, I’m giving you your child support check. Hopefully, it can cover that. Other than that, I’ll see you in two weeks. And that’s the norm.
I say all that to say, “I had an incredible amount of support from my daughter’s father, but also, at the same time, I’m sitting here trying to make this business work.” During all that time, I got one client. That was a little three-month engagement, and then it ended. Then two months later, I invested in my first coach — and that’s another thing. You’re like, “Invest right now to prove how much into this that you are, and then you will get that return back.” And I didn’t.
Then, a month after that, I had to move in with a family member because my lease was ending and there was nothing else I can do. That’s the dirtier side of entrepreneurship of just taking that jump that people don’t really talk about a lot.
Jess: I think you’ve had so many things. I’m literally scribbling my notes be like, “We need to come back to this.” Y’all, luckily, we are going to be doing a part-two with Alyssa and diving into D&I and anti-racism work — the culture of that in the next episode, so stay tuned for that.
But, I think you hit some really important things because when I first started entrepreneurship, and I saw the people that were success stories, which in entrepreneurship — me being nerdy — if you’ve heard the first episode, I refer to statistics a lot because they tell a story; data tells us the story. The percentage of entrepreneurs that actually succeed is actually very low. When I saw that, I kind of asked myself, “Why is this 5% to 7% so successful?”
When you look at entrepreneurs, the breadth of entrepreneurs is so wide. You have people like Jeff Bezos that started Amazon, and now has a huge conglomerate. Then, you also have people that started a bakery and a mom-and-pop shop — and that’s also successful. I want to talk about this huge spectrum of potential because I think a lot of people don’t realize two things.
One, the people that are successful — success, first of all, is subjective. What you view as successful, what’s been passed down to you as successful is subjective. Then, the second piece is, again, that support system that we didn’t know that they had, and maybe they’re an anomaly. There are people out there that have made a huge impact in their business, and did take that leap — maybe without the parachute. But, the percentage is so small, yet we are envisioning ourselves and that as the standard, and it’s not.
I want to go into this idea of success that you had a support system that your single mom didn’t have. How do things like that and being that as part of your identity play into the subjective idea of success that you have, as well as the roadmap to what to do? If you haven’t had an entrepreneur in your life, which I personally have very few — we don’t know what’s normal; we don’t know what is the path.
Granted, entrepreneurship is all about innovation and paving your own path. But, having support, and people, and mentors to bounce off of is really crucial too. Anyways, what do you feel does identity have in cultivating this objective idea of success? For maybe people that are looking to step into this path, what is the mindset that needs to be developed to be able to sustain something in this industry?
Alyssa: I just love that you asked that question because a year after all that whole story that I told you, I finally entered another group coaching program, and it was just filled with moms. I remember feeling so angry and bitter at everyone else’s version of success compared to what I needed for success. I would be so livid when people were like getting into such a huge mindset twirl over just wanting to make an extra $2,000 a month. I’m like, “Y’all, I have to support myself and my child while living in New York City. $2,000 a month, even $5,000 a month, is not enough for me.
I’m not here because I’m playing this game, and I want to see how much I can do and how far I can go. For me, it’s not even just a sense of survival, but having my child at the age that I did — I was 23 — there was such a sense of guilt that I was not financially prepared enough to provide her with what I was able to be provided with.
I remember when my daughter was maybe like two, for whatever reason other than to just feel shitty about myself, I looked up the address on my birth certificate because I remember the home, I remember what the apartment looked like. I decided to Zillow it because — of course. I looked at it, and I remember exactly what it looked like, and I was like, “My daughter will never be able to have that.”
At the time, I was living in the projects in of the worst areas of The Bronx, and I was like, “Look at where I am, and look at where I was born into — my daughter will never have that.” Fast forward into me making money and entrepreneurship and defining success for myself. For that, it was providing my daughter with the life that I feel like she deserves compared to what I saw like a lot of people in my space, especially like a lot of moms — there’s no shade anymore. I’ve gone through a lot of that bitterness.
But, it was like, “Oh, I just want to make more money than my husband so I can feel powerful”, “Oh, I just want to remodel my kitchen”. I’m like, “Y’all, I just want to get out of my uncle’s apartment. I just want to have my own space.” That’s what that was then.
Jess: I literally just got chills of you saying that because this is the shit that they don’t tell you about entrepreneurship, and especially operating in this industry as a person of color, as a woman of color. Our measurement of success is different. Then, what can this industry do to level the playing field, and I feel it’s just transparency. It’s not that we will never strive to be maybe that parent that’s like, “I just want to make more money than my husband for the power.”
It’s not that that’s good or bad, but help us get to that level, and what does that mean? We just need people to be fucking real with what the deal is and not create these spaces that are misleading, and then guide us into a mindset of shame and guilt that we’re not achieving or getting to the same place. Does that sound right?
Alyssa: For me, when you’re saying even just being transparent, I know for — again, thinking about the mom space because I coached in that space for a little bit too. What the hell does a $5k a month actually mean? What does that mean? Even if we think $5k cash, cool. Is anyone talking about the 20% that has to go to taxes? Or “the this” or “the that, or “the all the things”? What does a 5k month actually mean for someone who is using this money to also sustain themselves? That’s a huge piece that I feel like is really missed over. Instead, we’re just glamorizing numbers for the sake of doing so.
Jess: 100%. In terms of this industry, in the culture of entrepreneurship, let’s have a conversation about the solution. What can we do to move the needle? I feel that there’s two kinds of areas on the spectrum where it would be helpful to look at your identity and see, first of all, where you land. Then, what do you think are the barriers that we need to address in this space to make it a more equitable space?
But then also, as women of color entrepreneurs, I think we have work to do in terms of dreaming bigger, but also being real with ourselves. I think, for my clients that I’ve talked to that are women of color particularly or women-identifying folks — for example, instead of shooting for the 5k a month, be real with what you need and be a steward of the resources you have, leverage your network, that sort of thing.
For you, what are things that you would recommend to this industry, whether you are a woman-identifying or a person of color, or light-passing or white person — how can we bridge that gap?
Alyssa: You said something that really deeply resonated. I think this also just comes with the culture of the US where it’s very individualized compared to practically anywhere else, it’s more community-focused. The only way that y’all see me sitting here, talking about this is because I broke through my own pride to lean on my community.
There have been so many times where I had to ask for help. I despise asking for help. At least once a quarter, one of my parents is lecturing me about the fact that I don’t ask for help. The only way that we are able to truly break through the barriers that we’re created to have us stay small is if we lean on the resources that we already have. We do so from a place of empowerment instead of from a place of feeling like you failed.
The big moment that came up for me was when this whole “panini” started, my job shut down. I was like, “Oh, alright, great. I get to work on my business, finally.” Then, we realized, “This is lasting longer than two weeks.” My daughter’s father was like, “Hey, my job closed down too. Do you want me to come over and stay with you guys so that you can work on your business once Isabella’s school closed down?”
I had to get through a lot of pride to even say, “Yes.” I didn’t even give him an answer at that moment — I wanted to curse him out. But instead, I was like, “Let’s pause and be realistic about our situation here.” I said, “Yes.” He stayed for what was supposed to be two weeks — it has not been two weeks because the “panini” has been lasting longer than that.
But the mindset shift for me was later on, w hen I was with my coach about it, she was like, “I mean, you have an in-house nanny.” She didn’t say maid, but it was like a similar word to that. I was like, “Yes, I have an in-house nanny and a housekeeper. You’re right.” Being able to shift that for the purpose of even asking for help is so, so huge.
Jess: I think that’s something that we — I guess I’m only speaking from my own experience, right? Because I only can speak from that. But I also have a really hard time asking for help. I think our ability to succeed and be in this industry is a lot more gray than we think it is. I think that also plays into kind of what you were saying of, “Well, why does help have to be so binary?” It’s like, if we ask for help, then we failed. We don’t ask for help, then we’re are struggling. Can we like find it in the middle of that? I don’t know.
But I feel that also came up when you were speaking about your experience because I think moving away from the polarity that is, “yes”, “no”, “right”, “wrong”, “good”, “bad” — “weak”, “strong” even — will help us to find a path that is supportive to our life, but also expansive to our generation, and that can be both. This idea of, “If I’m an entrepreneur, that means I have to eventually leave my nine to five.” Well, what if you like your nine to five? That’s also something that’s been coming up a lot too.
In this current day and age where we have a workforce shortage because companies did not have environments conducive to employee well-being, and they’re starting to fix that in some ways. We’re starting to see a little bit of a return back to corporate America, which is the antithesis of entrepreneurship. When we talk about leaving it for necessity, what would it look like to go back or keep your job, or do both, or — we haven’t even gone into if you’re multi-passionate and want to do a bunch of different things.
I love what you said about help, and I think adding this idea of breaking the mold, which leads me to my last question for you — which is your molds. What molds have you been able to break through, or are breaking through that are fueling this identity of thriving? What does that mean to building your own generational wealth that goes beyond the money?
Allysa: Yes. Even just saying generational wealth, it’s so interesting. I never — I don’t want to say I was averse to the phrase, but I never was able to even conceptualize, “What does that even look like? What does that mean?” For me, I’m just like, “Okay, does that mean I’m paying for my kid’s college? That sounds good. But what else does that mean? I don’t understand.” As I’ve sat with even just that piece, it’s the freedom of options, and that is so, so big for me.
But especially as a woman, even more so as a mom, the freedom of being able to say — whatever this situation is, whether it be a job, whether it be a location, whether it be a relationship — “This is not suiting me.” To have the flexibility to move, and to leave, and to shift.
If there’s anything that I can give to my daughter or to even my close relatives, as a result of me doing this work, it would be to be able to have that flexibility that we should be afforded, and that we say is afforded like, “Oh, quit your job and go backpacking or whatever.” It’s like, “Where are they getting the funding for that?” That is what generational wealth looks like for me — for my child to have that flexibility, for her children to hopefully have that flexibility.
In thinking about shifting the mold, I feel like I’m someone who can easily be fit into so many different boxes because of all of the different identities that I flow into. At the same time, I don’t fit perfectly into literally any of them at all, and it’s something that I always, always struggled with. I felt like I was never black enough. I felt like I was never Hispanic enough. I felt like I was never — I had to prove that I was an actual gamer. I had to prove all of these different things that I hold close to my identity to now where I am where I’m just like, “I’m never going to fit into whatever someone else’s description of me is, but I’m just going to exist in it in a way that feels really, really good, and instead change their perception of what that looks like.” I hope that I answered that question.
Jess: Yes, snaps to that. I think that’s like everyone who has multiple identities, which is kind of everyone, and especially if you’re from the United States where it’s such a melting pot. I spoke about this in my first podcast as well — first episode about being a third culture kid, and that sort of thing, it really does affect your path and how you navigate things. I so appreciate you sharing all this. I think it’s such an insightful viewpoint and keyhole into an industry that really is confusing as fuck.
Nobody quite knows how to navigate, but nobody really tells you. It’s like a speakeasy, but where you don’t actually find the door inside, and you just started looking for how to get in and you can’t, but it feels like some like secret club that some people have figured out — when it’s really not. I appreciate you sharing that.
And I lied — I do have one more question for you. Last, last question, and then we’re going to end, and we’re going to jump into the second part of this two-part series with you. But, what is something that you are currently unlearning still in this industry — that someone that is new, or even not even wanting to become an entrepreneur. Maybe, they’re just looking for a new pathway in their career, or a new avenue or hub — I don’t know. Something new. What did you have to unlearn, and what are you still unlearning that is allowing you to still be in this space of newness?
Alyssa: One that’s coming up for me right now is professionalism. When I started this work, I was doing career coaching. I still had all my old clothes for my job. Whenever I would go to a networking event, I would just wear my old work clothes because I’m like, “This is what it looks like. This is what a career coach looks like.” How old was I? I think I was like 26. They’re already going to be looking at me here because I’m young, so I have to look this way to be professional.
Then, the whole pandemic happened. I was just hopping on lives in my pajamas because that’s just what I was doing. That forced my brain to change what professionalism meant. Now, into where my stage in my businesses, where I’m trying to start working more with corporate in terms of their leaders, and creating workshops and doing things like that, I’m being hit again, especially when I’m on LinkedIn, “Oh God! Now, do I have to shift into something that does not feel like me anymore? How do I balance still feeling like myself, and also getting my foot in the door?” It’s such an odd thing to try to balance, and I have to consistently reframe it for myself every day.
Jess: Wow. That is actually a really big thing that I didn’t think about — what is the culture of professionalism now? Even how it was toxic before — the idea where you couldn’t wear natural hair because that is unprofessional, and no tattoos. Now, that’s kind of evolving. So what is this next level of professionalism? Is it — can you show up to a meeting in a hoodie and sneakers, and still be a fucking boss, and know your shit, and be taken seriously?
Silicon Valley kind of is having this new, different, bro sort of culture. But can that bleed into other things, minus the bro-ness of it, I guess?
Alyssa: Exactly. To me, as a 29-year-old black woman, show up to those exact same meetings, teach y’all shit, and y’all not have a thought about me other than what came out of my mouth.
Jess: That is a big one. That also just sparked so many things that I want to talk about with you in terms of corporate space, corporate America, and all the things. We are going to end this session y’all. But, if you are wanting to know more about Alyssa, how you can connect with her — do you want to share where they can find you?
Alyssa: The best place to find me is on Instagram. That’s where I share educational stuff. Then, if you actually watch Instagram stories, sometimes I talk a lot. But they’re also educational, or they’re just me being me. But if you want to actually talk to me, do that on email because my IG DMs are such a hot mess that I’m attempting to get better.
Jess: Yes, aren’t we are all? Okay, I will see you on the next session of Unlearn Lab. Thanks for joining.