E26: Stepping Into Entrepreneurship with Annalyn Cruz

You do have the power, and you do have the agency to flip the script. You don't have to continue to maintain the status quo, or to maintain the way life has been so far.”

- Annalyn Cruz

Episode Summary:

The big decision to jump into a life of entrepreneurship can be a daunting one, and should not be taken lightly. At the same time, many of us have this calling, and when the time is right, it is also important to heed that call. 

On the show today is Annalyn Cruz, and she is here to talk about her journey and how she made the decision to quit her corporate job and the important steps and resources that helped her along the way.

Annalyn is a leadership and career coach, group facilitator, and professional speaker. Her philosophy is grounded in taking the right kind of risks and allowing success to grow in surprising ways, acknowledging the non-linear nature of our lives. Much of her work is focused on helping BIPOC women to reach beyond the limitations and conditioning that we are all subject to in varying degrees, and hearing Annalyn’s commitment to this important work is truly inspiring. 

In our chat, we get to talk about some of the hurdles and ceilings that we face as people of color, what it means to transcend these into a successful life in entrepreneurship, and how important it is to share these lessons with our growing networks. Annalyn also unpacks some of her important milestones, mindset shifts, biggest wins, and how the power of community has aided her along the way. Join us to hear it all!

What You’ll Learn On This Episode:

  • [03:06] An introduction to Annalyn’s journey with entrepreneurship
  • [05:51] The part that coaching has played in Annalyn’s work
  • [07:32] Annalyn’s decision to leave her corporate position to go it alone
  • [11:19] Common themes that Annalyn addresses with her coaching clients
  • [13:40] Continual learning around internalized racism
  • [17:36] Annalyn’s strategy when helping her clients transcend limiting fears
  • [20:15] The mindset shifts required when diving full-time into entrepreneurship
  • [26:28] How the TRANSCEND Community has supported Annalyn’s business
  • [29:41] Annalyn’s proudest moments to date
  • [32:44] Navigating concerns about pricing[
  • [37:34] Gaining confidence from conversations with fellow entrepreneurs
  • [41:21] Surprises that Annalyn has experienced in the world of entrepreneurship

Resources Mentioned:

Connect With Us: 

Connect with Annalyn Cruz:



AC: I’m really proud of it. It was the first thing that I basically did within my first month of having the business, pitching it, having the slide deck ready, putting my price out there. Thank you so much for consulting with me on that, of yeah, what is the value that the participants are going to get? Just being able to have that confidence to do the pitch and then to get the contract.”




[00:00:30] AW: You’re listening to The Transcend Podcast. I’m your host, Asha Wilkerson, an attorney by training and an educator at heart. This podcast is all about empowering you to build a business and leave a legacy. Here’s the thing, the wealth gap in America is consistently increasing. While full-time entrepreneurship is not for everyone, even a side hustle can change your financial landscape if you’re intentional about using your business to build wealth.


I’ve run my own law firm for over 10 years. In that time, I’ve helped countless California businesses go from idea to six figures. On this podcast, we talk about what it truly takes to build a sustainable business and find financial freedom. Let’s dive in.




[00:01:16] AW: Welcome back to another episode of Transcend the Podcast. I am so excited that you are still here listening with me. Every time that an episode goes out and you all tell me that you’re listening, my little heart just pitter-patter, pitter-patters, and I’m so grateful for your presence, and so happy that I can support you on your entrepreneurial journey.


In today’s episode of the podcast, I have a new friend of mine named Annalyn Cruz. We came to know each other through actually, Transcend the Membership. I have watched Annalyn just blossom as a new business owner. She came to me to form her LLC and join the Transcend Community and has really taken off. We discussed some of the things that we have learned as people of color that may be holding us back in entrepreneurship, some of those pieces of advice from our parents and our family members that were given to us to protect us, but that we have to shake now, because we’re no longer in a situation where that advice applies.


We also talked about some of her wins, her mindset shifts and the power of being in community. This is a really good episode and I’m super excited for you to listen. All right. Enjoy.




[00:02:24] AW: All right, Annalyn. Thank you for joining me on Transcend the Podcast. How are you doing today?


[00:02:30] AC: I’m good. How are you doing, Asha?


[00:02:32] AW: I am doing pretty well. Living the life, working remotely, fighting with the Internet. Trying to pretend I’m still in the US. All good things. Those of you listening who have these online remote businesses where you have to show up on Zoom, let me know what country you’re in, because apparently, that’s the one I need to be in if it’s working for you.


[00:02:56] AC: Global nomad lifestyle.


[00:03:00] AW: Totally, totally. Trying to get it. That’s the dream. That’s the dream I’m trying to live. Annalyn, thank you so much for being on the podcast. You are a part of the Transcend Community and that’s how we met. I am so fascinated by your entrepreneurship journey and your leap, and I want the world to know. Why don’t you tell us a little bit about what work you do and how you got started?


[00:03:22] AC: Yeah. Well, thanks again for inviting me to be on the podcast. Super exciting –


[00:03:27] AW: Of course.


[00:03:28] AC: – to be a part of it. Of course, to be a part of Transcend as well. The type of work that I do, I’m a leadership and career coach. I’m a group facilitator and a professional speaker. I have my own business, my own LLC that I opened up, let’s see, July 27, I want to say, of 2021. I’m still a newbie at this game. At the same time, and I feel like, “Oh, man. It’s been a journey so far.” It’s been good. Yeah, thank you for all the support and help you’ve given me over the past few months.


[00:04:06] AW: Of course.


[00:04:09] AC: What I focus in on is really helping to empower women and BIPOC leaders with their careers and the lives that they truly crave. That really centers me and my work and it feels so good to be able to just have that be my North Star, when I’m thinking about the types of programs I want to create, the clients I want to track, to my coaching practice. To just be focused in my work. It’s just been really, really awesome. To know that I’m creating that myself, along with of course, support from what I call my hype crew of just – and you’re part of that too, of just people in my community, other women entrepreneurs, especially just other folks who have been there before.


That’s been a big part of why I think I’ve been successful so far is that community, and being able to just learn as I go. It’s been a good ride so far, but there’s still so much to learn. I haven’t even been in this game for six months.


[00:05:27] AW: Well, that’s life, right? There’s always so much to learn. I think, one of the biggest myths that – or, maybe I don’t know, if it was a myth that was told to me, or just something I thought as a kid is that when I got to be an adult, everything would just make sense and it’d be easy. No kid wants to be a kid longer than they have to be. When you get to adulthood, and you’re like, “I’m still learning this stuff.” That learning is definitely a lifelong journey. Were you coaching before you started your own business, or is the coaching part new for your business?


[00:05:56] AC: I was coaching before at my last company. I used to work for Electronic Arts, or EA for short, the gaming company based out of the Bay Area in Redwood City. I was very fortunate, to have been able to have coached some of the leaders at the company. Then I also had started my coaching certification years back. Actually, the coaching courses I was doing at UC Berkeley. My career trajectory was I started out in higher education. I was thinking about this this morning that a common thread, I think, throughout my career is how do I coach, whether it’s students in higher ed, or on-college campuses, staff, or in faculty work there?


Then further along in my career, EA was like, how do I coach these people leaders, these people managers, or just employees for the company, who are just trying to get to a space where they could grow in their leadership style, and grow in that journey of theirs? I have been doing it for the past few years, but this is really the time that I – when I opened up my business, I’m like, “Okay, I’m going to have my own private clients. Start really charging for it, because it was a part of my role before, so no one had to necessarily pay out of pocket for it.” Yeah, that’s the part that’s new is generating my own pipeline.


[00:07:32] AW: Yeah. Absolutely. How did you know that it was time for you to leave corporate and to strike out on your own?


[00:07:40] AC: Yeah. I had an inkling, probably, or a curiosity that piqued probably around three years ago. I was about two, two and a half years in into my old role, and I just started thinking like, “What would it be like to actually break out on my own and have my own business, if I was doing this similar work?” Because I loved being in learning development. I loved being able to create content and facilitate experiences for folks. I was just like, “What if I was able to do this with my own spin on it, and to able to just do what I want to do with no restrictions, or not having to be a certain brand or way?”


It wasn’t until the pandemic, honestly, that this dream of mine kept knocking me over the head over and over of just like, what I call my inner wisdom, or the whispers became really loud after a while. I just felt like something was missing. Even though the work I was doing, it wasn’t bad. I love my team, and I love my boss. EA is a fun company to work for. I was just like, something. I don’t feel as fulfilled, as I should be feeling.


When I was going through my certification process for coaching, I’m observing, every coaching session I have with my coach, and every therapy session I had, and a lot of the conversations I was having with my friends was about like, well, what would it be like for me to leave? I was just so scared to do it. Anyway, long story short, I think this past May, I was driving back up from LA after seeing my family and had six hours in the car to really sit down and think about it.


[00:09:42] AW: Good thinking time.


[00:09:44] AC: Good thinking time. I was like, “I need to do this. I need to take this leap of faith. I need to make this jump. I’ve been wanting this for years now.” Even though I had still so many fears about going off on my own, I just knew I had to do it. The other pivotal point I would say is that when I came back to work, my manager had set out team goals for the next year. I was working on stuff that I really wanted to do. I requested to do this work. Yet, it wasn’t exciting me as much as I wanted it to. That to me was a huge sign to be like, “Okay, you have what you asked for, and it’s still not enough? You need to make some moves.” That’s what happened.


[00:10:36] AW: Got it. I like that story, because I think it gives some context to the time. Sometimes we feel we’ve got to make a move and strike out on our own, or people feel they have to make a move, and strike it on their own right away. You don’t have to do anything right away. You can take time and figure out the right opportunity. There is a difference between waiting for the perfect time, and then realizing that the time is now. People can wait and wait and wait and let that fear hold them back. You didn’t do that. You waited until you felt like, “Okay, I got to do this.”


Even in the midst of some fear and uncertainty, stepped forward anyway. Kudos to you for taking that leap of faith for sure. I’m curious, now looking at the folks who you coach, so women of color, BIPOC women, are there recurring themes or issues that you tend to see within the people that you coach that you are helping them work through?


[00:11:35] AC: Yeah. I would say, there are a few different themes that come up. I coach both BIPOC and white women as well. I would say that from – two things. From a gender lens, there is the challenge of finding one’s voice and feeling confident in sharing their perspectives, or showing up in a different way, when they’re perhaps the only woman in the room, or they’re the only person of color in the room. Being able to just figure out, “What’s my own leadership style?” Particularly if someone is BIPOC.


We have a lot of cultural nuances and experiences that we bring, where just yesterday, for example, a woman leader, black woman leader that I was working with said to me, “I don’t feel like I could be my authentic self. I’ve been told not to.” I think for instances like that, or I had another woman who’s Asian Pacific Islander, who said, “The reason why I want you as my coach, not only because I know, you know how to coach me, but you have lived experience that when I had a coach who wasn’t from my background, I had to explain to her what it meant like to walk in my shoes and what I was born into.”


I think that the commonalities there around being other, and being in these dominant spaces where folks often have to find out like, “Yeah. Who am I as a leader? What is it that I want for my career? How do I advocate for myself, when this system wasn’t necessarily built for me to succeed in the same way?”


[00:13:32] AW: Right. Right. Yeah, absolutely. I didn’t mean to cut you off.


[00:13:36] AC: No, no, no. Go for it.


[00:13:40] AW: Okay. I was just thinking, what came to mind is that I say all the time on this podcast, and just in life in general, bring your full, authentic self to the table. Whether you are doing that as an entrepreneur, or as an employee, if you held back Annalyn, and who you were, your essence. You are Filipino, right? You have Filipino heritage, and bring that culture with you, the clients that you were looking to coach would miss out on that if you didn’t bring your full culture and heritage in these things that we have been taught our differences, and maybe may make us the other. That’s what makes you so great at what you do, because you can do this from your own lived experience. It sounds like, you’re also encouraging the clients that you coach to also bring that full lived experience with them as well.


[00:14:33] AC: For sure, for sure. It does start with us, one, obviously having a safe space to do that. Two, being courageous enough when we do have opportunities to do that. To be like, “Yeah, here is my story. I have battled internalized racism, for example.” Earlier in my career, where it was hard for me to find my voice, because I grew up in a family that said, “Don’t rock the boat. Don’t argue with your boss.” My dad would tell me that.


While I have an awareness of that, and know that I don’t have to adhere to those rules, or generalizations, there’s been a part of me that has internalized some of that. How do I even push back on that to know, are these messages still serving me at this point of my career? No, they’re not. I feel very privileged to be a coach, to be someone who could help another person in their journey in finding their voice, in finding the leadership style that works for them, in advocating for themselves and what they want, not just within their careers, because I’m also a holistic coach, where I’m like, whatever happens at work, there’s other stuff in your life that’s affecting how you show up.


To me, it’s like, how do we look at this holistic way in which you are living? What’s a dream that you’re trying to go after right now? I’m going to help you get there. I’m going to be your champion through all of that.


[00:16:15] AW: I love it. Come coach me. Sign me up. Yes. No, I absolutely love it. I mean, those same things. You’re focusing primarily on folks who are still in that corporate world. A lot of those things still come up in entrepreneurship, right? Where we’re finding our voices, battling those things that we’d heard like, don’t rock the boat. Or, on my side of the family, I heard, “You got to be twice as good as the next person.”


I was saying yesterday, I don’t remember if I was recording the podcast or not. Just, the thing about hair. I think I was recording a podcast yesterday, talking about hair. When I was in law school, and I had my hair straight, or straight as it could be, for my interview, and then I got the job. I was tired of doing my hair, so I got braids. I remember my mom being really concerned that I wasn’t going to be able to keep this job, because of the way that my hair looked. Now in 2021, that probably sounds a little bit crazy, but that wasn’t her experience. She had known people who had lost their jobs, or not been hired.


Now in California, we have the CROWN Act to protect discrimination from hair. The point is that those pieces of advice like, don’t rock the boat, or keep your hair straight, conform, essentially, no longer serve us as entrepreneurs. How do you support people in breaking out of those limiting fears that have probably come from a good place to keep us safe, but now no longer serve us as after people, entrepreneur or not, who were trying to go out and build our dreams?


[00:17:56] AC: Yeah. Well, I think the first thing is even acknowledging that it’s their right to know, what were the messages that I was surrounded by? Regardless if it was one of our parents, folks we grew up with. What were those messages that we heard early on? Thinking about the origin of it. Then it’s like, well, why are they showing up? Why was this person telling me this? To your point, maybe it was to keep us safe.


We all have our own Gremlin saboteurs, our inner critics come up pray and will tell us like, “No, don’t do that, or stick to this way.” I’m thinking about this chart that I ended up designing for this keynote that I did recently, which was, okay, so how do you flip the script on that? Are those messages still serving you? How are you feeling about it? How is that affecting your well-being, your mental health, your emotional health? If you realize it’s not serving you in a positive way, well, what’s another way to look at it then? It’s like, what a different perspective in how you could see what’s happening to you right now?


I would say, to answer your question directly, it’s being able to walk someone through that process, and then allow them to see, “Okay, well, what else is here? How do you want to approach your life now?” Because you do have the power, and you do have the agency to flip the script on it. You don’t have to continue to maintain the status quo, or to maintain the way life has been so far. We do have power. We do have agency in that.


I think, it’s allowing people the reflection time to think about where are these messages coming from? Are these fears still serving me? Then okay, well, here’s what I’m going to do about it then. Here’s a path I’m going to take for myself that feels more empowering and full and creative, instead of it holding someone back.


[00:20:08] AW: Yeah, absolutely. I feel that is work that is always done as an entrepreneur. Maybe just in life in general, but certainly as an entrepreneur. I am curious now, after making the transition from corporate to entrepreneurship, what are some of the mindset shifts that you have had to make to be successful? Then, we’ll talk about some of your wins along the way that you’ve had since July.


[00:20:30] AC: Yeah. Oh, mindset shift. Well, I think you helped me along with my other business coach and other folks who’ve been doing this for a while, which is, you can’t do it all. You’re the CEO now. Coming from an immigrant family, coming from someone who prides herself on, “I could get it done.” I’ve had so much adversity in my life, I could do it by myself. The mindset shift there for me has been, yeah, you can’t do it all. Or you can, but do you really want to learn how to be great at HoneyBook, or Dubsado? Or are you trying to be the expert in finance systems that you have no idea what that means, or even how to go about it?


I realized that I was spending time thinking through things that I shouldn’t have no business researching, or really taking as much time as I was prior. Because of that, I just was like, “It’s time to get some help. It’s time to realize that I need to take a step back. I need to delegate.” Last week, I hired a virtual assistant, again, based on some of the advice that you had shared over your podcast and what we’ve been talking about within Transcend. I was able to hire someone who hopefully, within the next week or so, will help me move my business forward in a way that I wouldn’t have been able to, if I was getting stuck in all this minutia and trying to do all the things.


[00:22:22] AW: Oh, my gosh.


[00:22:22] AC: Are we good?


[00:22:23] AW: All right. Since you have transitioned from the corporate world into entrepreneurship, what are some of the mindset shifts you’ve had to make in order to find the success that you have found today?


[00:22:35] AC: One of the biggest shifts that I made recently was really understanding that you can’t do it all or you can, but you’re going to be wasting a lot of your time spending time and energy on things that other people have an expertise in. I want to say, one of your podcast episodes, and we’ve talked about this within the Transcend community is hire a virtual assistant. I went ahead and did that last week, and it has already been, having since serviced as it is.


I met my VA today. One thing I want to say about that is coming from an immigrant family, and being a person who I realized is a good, or excellent student, like I prided myself on being really determined and doing all this stuff myself. I’m like, it drains me. Two weeks ago, I had such a bad week, because I was trying to take it all on. I was like, “Okay, I need to shift my mindset in, even though right now, I’m a solo LLC CEO, I’m still a CEO.”


People, like my business coach was like, “You are now the CEO. Do you think other CEOs do everything in their companies? They hire people who are excellent at those tasks, or those projects, so that it can free up your time.” I just kept hearing that message over and over again, whether it was from you or her, or other folks who have been in the game for longer than I have. I’m like, “I need to invest in my business and in myself, in order to keep the passion growing, in order for me to not burn out,” because I was just feeling really unhappy about that. That’s one thing.


Then the other thing I would say, which has been actually, a really beautiful experience since going into entrepreneurship, I’ve been reconnecting with people from my past, who whether I used to work with them, or they were an old student of mine at a university I used to work at. We’re just connecting on different levels of, what are you up to now? People are curious. Like, “What made you take the leap?”


Honestly, I think sometimes it gives people the courage and also, just the curiosity to be like, “Maybe I could do that, too.” I’ve had this dream around opening my own business, or I’ve had this dream to quit my job and go into a different industry. That’s been really cool, too, in terms of let me reconnect with people from my past and past folks who have been within my circle, who I just lost touch with, especially during the pandemic. It feels really good to just reconnect with other human beings, especially having been isolated during the pandemic. It makes me just realize how much community and connection is so important, to my values and how I live my life. That’s been a really beautiful process.


[00:25:46] AW: Yeah, and I love that. Absolutely love that.




[00:25:48] AW: Hey, excuse me. Pardon the interruption. I know you were listening intently to the podcast. I just want to tell you that I’ve got this great checklist for you to download, if you are a new business owner. Or even if you’re thinking about starting a new business. It’s called the New Business Checklist. It’s got 12 things that you need to know as a new business owner, to help grow your business and make it ready for the wealth infusion that you’re going to have, so then you can leave a financial legacy for your kids and your kids’ kids and your kids’ kids’ kids.


If you’re ready for that checklist, head on over to transcendthemembership.com/checklist and get it for free.




[00:26:28] AW: Thinking about, the first thing you talked about in terms of not taking everything on yourself, there is – I feel like, especially in communities of color, one, because of lack of resources. Two, we have mostly worked so hard to make our parents proud. Also, that was instilled because that was what we learned to do. You have to hustle. You got to work really hard, because that old motto of work hard and success will come was what we, most of us grew up with.


Now, we’re working on working smarter, not harder. If you work hard, fine. But at least, make sure that it gives you the return you want. There’s nothing wrong with hiring the experts to do the things that they are expert at. That’s why they are the experts. Then, the power of relationships and community building. I think that is so, so important. Can you talk a little bit about how the power of Transcend and the being in the community of Transcend has helped you in your business?


[00:27:25] AC: Yeah, for sure. I mean, first of all, just the resources that you have within the program. That’s the reason why I signed up for your program was to do the online, how to even build an LLC, or what is that process like? Because I tried doing it on my own. I got Google doubt. I was like, “Oh, my God. I cannot deal with this.” I’ve heard other people say the same thing to me of like, it’s such a daunting process for many of us. That’s one thing, are the resources.


The other thing is recognizing that I’m not going through this alone. That community aspect of when we get together on Thursdays at noon, is being able to hear what other people may be challenged by, or struggling with. To be like, “Yeah, me too. Plus one on that comment.” It’s like, even though we may all have different businesses and folks that we’re serving, there are some commonalities that happen, especially when you are a BIPOC business owner. There are just things that we have in common. That’s been really great.


Arianna, who was on the podcast recently, she helped me look at my website, and just give her opinion on my front page. That was really generous of her to do. It’s like, now my network has expanded even more. When I was saying before, of reconnecting with folks from my past, my network has now grown exponentially since July. It’s like, people are hearing things that I’ve – the keynote I did. Or now, I’m working with a different company, on a leadership development series for women, that I wouldn’t have met these women if I was at my same company.


That’s been really awesome, too, is to just expand my community as well. That’s just always been important to me ever since I was in college, and it’s been, again, such a blessing. It’s such a gift to have that right now, during this time when we’ve been so disconnected during the pandemic.


[00:29:40] AW: Yeah, that’s awesome. What is the win that you are most proud of in your business so far?


[00:29:46] AC: I have a meta one, and then I have a specific one. The meta one, like the 10,000-foot view, I would say is, just the fact that I took the leap of faith and I’m doing this thing. The fact that I pushed through the fears and pushed through what I thought was going to be disappointing to my parents has not been. I was so worried at first of like, “Oh, my God. No one in my family is an entrepreneur.” I didn’t learn that stuff. Neither of my parents were entrepreneurs. They had very steady jobs, their entire careers.


Breaking out of that, knowing that I was the person who was going to take that leap of faith, also being a solo person. I’m not in a partnership right now, and that was a big deal for me too, to be like, I’m truly doing this on my own. I have that much faith in myself that I’m going to do it, and I’m going to be successful at it. That to me, is just a huge win.


Then the other thing I would say is, I have built this leadership development program called – I got to get the title right, because it’s so long. Lead with Empowering Presence and Confidence. It’s really a program that I have built for women leaders who are trying to even amplify their voices and to feel fully confident in the spaces in where they’re at, and to recognize what happens when I feel choked up, or when I have anxiety around some of these things that we go through in our day-to-day jobs? How do I uplevel my skills, so that I can go after the types of roles and the types of career that I want to build for myself?


I have designed and developed that from scratch. I’m now able to facilitate this for other women leaders. It’s just been a really positive experience. Yeah, and I’m really proud of it. It was the first thing that I basically, did within my first month of having the business pitching it, having the slide deck ready, putting my price out there. Thank you so much for consulting with me on that, of yeah, what is the value that the participants are going to get? Just being able to have that confidence to do the pitch, and then to get the contract. That was huge for me.


To have a big win like that out the gate, just gave me more confidence that I could keep doing this. I did this in my first month. Even bigger and better things are possible, and it’s going to happen. I would say that that’s a really big win.


[00:32:41] AW: Yeah, that’s awesome. Congratulations, and kudos to you for all of that. Those are some amazing wins. I want to just go back to the pricing thing real quick, because I want to use it as an example that of how to move through the fear when we get uncomfortable. Because when you’re first starting out, or sometimes even when you’ve been out there for a while, but you can be isolated in your business, and you may not know what the going rates are for different projects, or activities, or items that you’re creating, or services that you’re rendering. That may not be something you can just go and look up.


The other part for that is often, I find that women and also people of color, we tend to under value and underprice our services, because there is, I don’t know, I think of I have never really been to a fancy Mexican food restaurant outside of Mexico. Because the idea is that Mexican food is supposed to be cheap and affordable, like street tacos. That’s not it. Anyone who wants to break out of that mold, let’s say, has to really have some confidence and some belief behind them.


Same thing that happens with pricing. “Oh, my gosh. I’m going to form this business for somebody. Is someone actually going to pay me what it’s worth? Or because it’s me, should I be charging somewhat less?” We actually did a little bit of work around the pricing. Can you give us just a little bit of background without too many details, whatever you feel comfortable with about that? Then talk about how we move through it?


[00:34:16] AC: Yeah. Well, to even take it further back, I remember talking to one of my best friends about the experience. I was like, “I don’t know. I think I’m going to charge $3,000 for this.” She’s like, “Girl, are you crazy?” She was like, “That is not enough.” I was like “Really?” I started thinking about, yeah, what would it take to develop this? What is the time, the energy? Going back to when I talked to you, I think what was really valuable about that conversation was you saying, “Hang on, though. Yes, there’s the time that will take to develop this, all that good stuff.” What’s the value in what’s the impact you’re going to make on each person that will be in experiencing this?


Then we broke it down into, okay, so if this is like, X is the final number, think about, well, what’s the true investment that the company would be making per individual? I think, that also opened my eyes, because I started thinking about, yeah, if someone was to attend a professional conference, for example. Sometimes that cost $1,000, $2,000, $3,000, $5,000 and beyond, depending if they’re traveling somewhere. I’m like, “And this is a way in which they’re going to build community at their company. They’re going to get one-on-one coaching with me.”


I started to really reflect on what you told me around the value. That’s what got me to the price that I did. You know what’s funny, five minutes before the meeting, I was like, “Okay, this is my number.” Then right before, I’m like, “I’m going to increase it by 5K. I’m just going to see what they say.” They accept it. They were like, “Okay, cool.” We went through the whole process of contracting and whatnot.


I worked myself up so much around, they’re going to say no, or they’re going to try to talk me down, and they didn’t. A similar thing happened recently with a coaching client that just yesterday, she’s like, “Okay, that’s the price? Cool.” In my mind, I was working myself up like, “Maybe this is too much. Maybe she’s going to try and talk me down.” I think, it’s often that fear of, is someone going to come back to me and say like, “No, that’s not worth it.” Not even that I can’t afford it, it’s more like, “No, what you’re charging me is not going to be worth the price.”


I think, part of the work that I’ve had to do, and if I could offer that to any of the listeners is just stand in your own inner wisdom and knowing that there is plenty of value of what this person is going to get out of. Any service product, or whatever we end up offering to people. To just know, and if it doesn’t work out with this person, or this company, someone else will say yes. Again, stand firmly in that. It’s a process and it’s not easy at all. It’s part of the work of just going through that and the nerves and anxiety.


[00:37:31] AW: Yeah. Oftentimes – go ahead.


[00:37:34] AC: I was just going to say, if I could add one other thing, because this has been a big aha for me, is talking to other entrepreneurs who are doing the same work, and uncovering the veil. Just opening up the curtains of how much do you charge for XYZ? Because we’re often taught to not talk about that stuff.


[00:37:56] AW: Very often.


[00:37:58] AC: Yes. It’s like, no, the more that we know, the more we could support each other and recognize that yeah, you are under-charging, or someone will tell me the same thing. No, you need to increase that, or here’s the market rate. It’s like, I think we’re often taught to keep numbers so hush-hush that hurts us as business owners when we do that.


[00:38:23] AW: Yeah, absolutely. I think, everything that you just said, just again, I think speaks to the power of being in the right community with the right people. You have those people around you who can encourage you to charge more. I think, also getting out of our own way, when it comes to pricing and offering the services. If you can take a bird’s eye view and really think about the value that you’re providing someone, like we had talked about, it takes you out of the equation. If you were thinking, “Oh, I can’t charge this much. Oh, I don’t have enough education, or I need another degree.” Forget that. Thinking, what is the value that is being conveyed to this person who is taking this course, or doing my coaching, or who is buying my product? Then you can price the value.


In that specific situation that you talked about had something to do with employee retention. I’m like, it costs companies about a $100,000 when they lose employees. Whatever the price is for the workshop, it’s going to help with employee retention, that short of a $100,000 is a great price.


[00:39:32] AC: Yes. Thank you for bringing that up. I forgot to mention that. Yes, I want to double down on what you just said, because that was huge to add a slide with legit stats that are out there of saying, here’s the cost of when someone leaves the company. Here’s the cost of what it takes to onboard someone, if you have to hire a new employee. Here are the thousands and thousands and thousands of dollars, if not millions that companies spend every year when they lose good people.


[00:40:03] AW: Yeah, absolutely.


[00:40:04] AC: I think, that was actually a huge selling point in terms of the company’s investment per person when they think about, again, the larger costs. If any of those women were to leave the company, it would cost more than what I charge for the entire program.


[00:40:20] AW: Absolutely. Absolutely. Again, there’s the mindset piece that needs to be done to be able to charge what you say what we are worth. Then, there’s also the real logistical piece of it of there is actually some value that you can compute and fall back on to help support you through this limiting belief of, I don’t know if anyone’s going to pay that, or I don’t know if my service is worth it. When you do the numbers. you calculate the value, please, you got that. Really glad that you were comfortable enough and felt safe enough to actually bring that to the community, and then we could actually talk about it. Because the community also rallied around you as well, to support you through that.


[00:41:09] AC: Totally. Yeah, and it was really cool to be able to come back and tell y’all, come get this later. Yeah, they signed the contract. It’s a yes. I was like, “Yeah!”


[00:41:19] AW: Absolutely. I’ve got two more questions for you. Why is one surprising thing about entrepreneurship? Maybe something you didn’t expect? Then we’ll follow that up with what is something in a positive way that you didn’t expect? Or what has been a benefit that has made it all worth it to date? Because there are always ups and downs. I feel like, having a business is like having a kid. It’s unpredictable, but you love the thing anyway. Things you are prepared for and then things that are positively surprising. What are a couple of those things for you?


[00:41:56] AC: Yeah. I would say, some of the biggest challenges has been the learning curve. I don’t know what I don’t know. You could do all the googling you want and all the research you want online, but you really don’t know, until you step into it, as with many things in life, right? I think, that’s been the biggest challenge of like, “Oh, my God. I have all these ideas for my business. Oh, my God. This coach is doing some amazing work. Look at what she’s doing on Instagram.”


The challenge has been, and I’m a big ideas person, right? I have ideas going on in my head all day, all night. It’s like, learning to focus in on, okay, so I just built this leadership development program. Let me continue that thread, and get that out there first, before I start thinking about my memoir, as much as I want to do that. As much as I want to do my memoir, it’s like, okay, what’s already here?


I think, the challenge has been, man, what am I focusing in on today? Just yesterday in my other business coaching group I’m part of, it’s like, what are my big rocks for today, for this week? Getting that real, laser focus on goals for myself per week, per month, per quarter. That has been, I would say, a challenge, but also, a good muscle for me to do, because it’s on me. I have to figure out what those things are, versus when I was with the company. It’s like, “No, these are the team goals. Here’s your priorities. Go.”


Then, some of the positive things, I will tell you, and hopefully this won’t change. I know, I’m still new at this, but it’s like, I have had time to breathe in between what I’m doing and to be really intentional about who it is that I’m serving, the type of work I’m taking on. Again, being able to meditate before I do a group facilitation. I never used to do that before. I would just go. It was like, go, go, go, go, go.


Now, I have built in intentional times for me to reflect, to journal, to think about, wow, all these connections of what I’ve been experiencing. Whether you want to label as God, the universe, spirit, whatever. It’s like, there’s a plan for me, and I know that I’m living my purpose now. That feels freaking good to just know that I’m in alignment with that. I felt, I was somewhat out of alignment in my last role, or what I had been doing, even years back. The intention wasn’t there. That’s what I think is the beautiful thing that happens with entrepreneurship is where you get to focus in on your dream and your purpose and what you want out of this life.


We only have one life in this body, at least. It’s like, I’m going to make the most out of it, and I’m going to forge the path that I want for myself. So far, it hasn’t steered me wrong in the past few months. I just feel, honestly, more alive than I have felt in many years. I think, it’s because I’m finding new ways of being and doing and showing up in the world differently. People comment to like, “Wow, you have such a great energy.” Just things that I wasn’t hearing before. I’m like, “Wow, is this what it means when you are in alignment and when you’re doing what you’re meant to be doing in this world?” I think, the answer is yes.


[00:45:47] AW: I think, the answer is yes, too. That’s absolutely beautiful. Well, I just have to reiterate, again, I am so happy that we connected, and so proud to support you on your journey. Also, just to witness your journey. You’ve been such a light and an inspiration. Every time I see you log in on Thursdays, or when we meet up down the road and going to [inaudible 00:46:05] Square for our little business meetups, I am delighted by your presence and your company and your shine. Thank you so much. If people want to reach out to you, maybe get interested in coaching, how can they do that? How can they find you?


[00:46:22] AC: Yeah, two ways. You can find me on my website. annalyncruz.com. A-N-N-A-L-Y-N-C-R-U-Z.com, or groundedinwisdom.co. Either way, will take you to the same site. Then folks can find me on LinkedIn as well, so they could feel free to add me on there.


[00:46:42] AW: Cool. Well, thank you so much, Annalyn. It’s been a pleasure.


[00:46:46] AC: Thanks, Asha. Thank you so much.


[00:46:49] AW: Of course.


[00:46:49] AC: Thanks so much. Yeah. Bye.




[00:46:56] AW: Hey, there. Thanks for listening. I really hope that you enjoyed the episode this week. I am so, so grateful to have you here. I hope that you are ready and feeling empowered to build your own business. You are needed. You are important, and I want to support you. If you have just started a new business and you’re not sure what to do next, I’ve got a great checklist for you to download, called The New Business Checklist. Head on over to transcendthemembership.com/checklist and put your name and your email into the box and you’ll get the checklist instantly.


Also, I want to ask you one more favor. If you want to interact with me on a daily basis, head on over to Instagram and follow my account @AshaWilkersonESQ on IG. I post on there daily. Can’t wait to answer your questions and begin the conversation. Talk to you soon.



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