Ep 16: Meet Kenny, Serial Entrepreneur and Master Delegator

Ep 16- Kenny Schaumacher_20230802_185335_0000

Akua interviews serial entrepreneur Kenny Schumacher. Kenny has been starting businesses since college, where he studied accounting. For him, the thrill is all in the startup and the building of the company. He has founded many businesses and successfully sold 2 of them. He thrives in handling operations and building out teams to operate the business.

It may sound crazy to many business owners, but Kenny tries to remove himself from the business he created as soon as he can. Many CEOs would say their business is their highest priority and that they can’t imagine things running without them. Akua asks Kenny to explain why he delegates so much, how he delegates effectively, and when he knows it’s time to move to the next project.  

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What's Covered in this Episode About Passive Income

  • Advice for founders and CEOs who need to delegate
  • When to let go in the business world 
  • Getting started even if you make mistakes 
  • Finding passive income
  • Separating yourself from your company

Quotes from this Episode of Open Door Conversations

  • "I always try to focus my time on what only I can do, or at least things that I can provide the most value, which I think would be the basis of delegation, really." - Kenny Schumacher
  • "If you are considering selling your business, which was always kind of in the back of my head, you definitely want to make a business in which you can separate yourself from that business." - Kenny Schumacher
  • "As soon as possible try to sell even if you just means like making a landing page or if you're building a product like having a Kickstarter, whatever, but just some way to get like real feedback." - Kenny Schumacher

Mentioned in Meet Kenny, Serial Entrepreneur and Master Delegator

Get to Know this Episode's Guest

LinkedIn: Kenny Schumacher

Twitter: ​​@KennySchuma

Get to Know the Host of the Open Door Conversations Podcast

Learn more about your host, Akua Nyame-Mensah.

Akua is a certified executive and leadership coach, recognized learning and organizational development facilitator, speaker, and former startup executive. 

Since 2018, she has had the opportunity to partner with amazing organizations, from high-growth startups to multinational brands all around the world, to maximize people, performance, and profit.  Outside of her coaching and corporate speaking engagements, she is a regular mentor, coach, and judge for various entrepreneurship-focused organizations.

Stay in touch with Akua Nyame-Mensah, Leadership & Culture Advisor:

  • Read about Akua’s services if you’d like to learn more about how you can hire her to help you strengthen your organization’s culture.

  • Complete her contact form to jump on a call.

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Here’s the transcript for episode 16 about Serial Entrepreneurship

NOTE: Please excuse any errors in this transcript; it was created using an AI tool. Akua Nyame-Mensah 0:07 Welcome to the open door podcast. My name is Akua Nyame-Mensah Chaos respond to Aqua and I'm a certified executive and leadership coach recognised facilitator and former sort of leader that loves supporting reluctant buyer fighting and overwhelmed leaders. I've worked with them to help them clarify where they should focus their time and energy each and every day so that they can love themselves, love their work, and ultimately love their life. If you're looking to learn leadership information and hear different perspectives, you are in the right place. My aim in this podcast is to help you see that one of the most productive and profitable things you can do is deeply understand yourself. Understand how you show up, understand how you thrive and allow yourself to align everything in your work in your life, and in your business to support that think of this podcast as your weekly opportunity to receive leadership support. And remember, there is no one right way to lead yourself or others. Thank you so much for taking the time to join me today. Let's get started. Hello, and welcome to this episode of the open door conversations Podcast. Today I am it's so excited. As I always am about this interview, I'm going to be sharing with you all about delegating and letting go I think it's such a great follow up episode to my previous episode that I will include in the show notes all about how difficult it is for us to delegate and ask for help. But today's interview is with someone who is a serial entrepreneur, he actually was an accounting major before starting his many different businesses. So today we're gonna be talking a bit about his background, where we talking about one of his products that I actually use to use for my business, that's called della sign that is all about his ethos about delegating, and how important delegating is in order to be able to scale your business. He also provides a lot of advice for founders and CEOs around not just delegating, but around when to let go and when to leave a business. If you are a founder, entrepreneur or CEO that wants to get some insight into someone who has successfully built several businesses, and spun them off to invest in things that he is very passionate about. This is the episode for you. So without further ado, let's get into it. Alright, so today I am joined by Kenny Schumacher to talk all about delegating and letting go. Kenny, welcome to the show. My pleasure. Thanks for having me. So for folks who are meeting you for the first time, could you please share a bit about who you are and what you do? Speaker 1 3:02 Yeah, absolutely. So I'm an entrepreneur, I've founded solo founded and sold two businesses, both of them in the product space. And I after my exit, I'm now working on two other businesses, happy to go into more detail on them. But I'm just yeah, overall, an entrepreneur looking for things to do investments to invest in and ways to stay busy. Akua Nyame-Mensah 3:21 Yeah. So let's talk a little bit about Yeah, some of the first companies that you've built, and how you even knew it was time maybe to let them go. Tell us more. Speaker 1 3:30 Yeah, so I founded many companies of the past, but most weren't successful, especially in college, I found a lot. But that was kind of like my way of getting into the entrepreneurial mix, learning mistakes, learning things, from mistakes, doing lots of things delegation. In college, I couldn't really afford to hire local people, or really, most people really. So a lot of that was finding my friends, finding other partners I could work with on a kind of free basis. And then beyond that, I kind of got into outsourcing out of necessity, because I you know, again, couldn't afford to hire local people here. But my first real success with business was after college or kind of my senior year of college. I was at that point in time, I had finished working on two other startups. One of them was an app, kind of similar to Yelp, but focused on dishes like specific food dishes, Yelp, you'd search for like a restaurants. And then you'd find the photos from their other dishes. But for ours, you could search like pasta, and get results of say, like actual pasta dishes, and then find the restaurant. But as I mentioned, I was you know, a poor college student couldn't really afford to, you know, hire people to do a lot of the work. So and I definitely couldn't afford to pay for ads for that startup. I had to think to myself, like how can I find people that would be interested in using this app? And more importantly, to how could I really find them in specific cities because this business was or this app was focused on finding food in your location. So we couldn't just launch and the entire world had to be launched by cities. So I kind of stumbled across Post Instagram because that was a good way of finding people by location. And there's a bunch of foodies on Instagram too. So that was my like, Aha moment of like, Oh, I could probably utilise Instagram to find users for this app. But my next problem was like, how could I get these people to actually be interested in what I was doing. So I have the idea of creating a foodie page on Instagram that was focused on a specific city. So I'm in San Jose, California. So I made one like San Jose foodies account on Instagram, I would post a bunch of like food photos from San Jose. And then using that account, I would interact with people in that general vicinity of San Jose or surrounding cities. So that worked pretty well. And I was able to automate that. And that account grew fairly decently. But the the most important aspect of this was that I then apply this to other cities, too. So by the end, we had about like, 300 different instrument counts that were being managed using VAs using software. And in total, we had about like 3 million followers cumulatively over those, you know, 300 accounts, so varying from like, 5000 followers to like 30,000 followers on the bigger one. So it kind of became its own thing, like the initial startup that I mentioned, like we we did, okay, like I got into this accelerator programme, in like, it was a government sponsored programme. And that was pretty cool. But it wasn't really successful by any means. So this Instagram thing kind of became its own thing. And then other businesses kind of found out what I was doing. And they asked if I could help them. So that became its own business separately, too. But that was like the end of my senior year of college. And I was spending a decent time doing this. So I thought that I would have to hire help, because I didn't want to spend 10 hours per day working on the business forever. So I started by hiring outsource because again, you know, I had some experience by this point doing that it worked well in the past. So why not focus heavily on that. So by the end, I had four full time workers, I was spending maybe only about two hours per day, or sorry, two hours per month on the business, I really was just paying the employee because I had manager or a manager in place to kind of manage the employees, I had the systems and processes in place to make sure that everyone knew what they were supposed to be doing. And were held accountable to doing these things. And, of course, you know, I paid a lot better than like the average rates, or even though like competitive rates for people that worked overseas, in that area of the Philippines. So it was all around like a benefit for everyone involved. And I had very loyal, very great employees on my team. So it was a good situation, but one that I wasn't necessarily super passionate about either, because I was only spending about two hours per per month on the business, it got to a point where I felt like someone else could probably do a better job if they were more involved in the business. And by that point, I wasn't really trying to spend more time in the business, it was kind of a, I guess, you could say a lifestyle kind of business. I wasn't making like crazy, crazy sums of money. But it was definitely a good amount. And it was especially good amount considering the only you know, two hours per month, whatever I was spending my time on. So that was you know, kind of my trigger to then look into possibly selling the business or if that would even be an option. And then that kind of like spelling me along to selling the next business and so forth. But it was kind of like my first real success in business. Akua Nyame-Mensah 8:15 That's absolutely amazing. And I feel like just with what you've shared, you've gone over so many important things that founders and CEOs need to learn. And it seems like you've learned that within such a short period of time. And so early on what made you comfortable, you know, delegating and finding these individuals in the majority of them weren't physically close to you never had a chance necessarily see them face to face. How did you build these processes? And how did you build this trust? Speaker 1 8:40 Yeah, I guess everything was sparked by necessity, really, because first of all, I couldn't do anything by myself, there was no way to do everything. And even if I tried to, I'd be super burnt out after maybe a few, a few days or a few weeks. So I knew that I had to delegate, I didn't really know, you know, the term of delegation or how it worked or how to do it effectively. I just knew that I had to do this. So you know, of course, when I first started doing these things, nothing was optimised. I was probably doing everything wrong, but at least I was going in the right direction of starting to try to optimise towards delegation. So first, it started off with me just hiring people overseas, I made some pretty bad hires, honestly, people that weren't great for it. So, you know, from that perspective, it was a waste of time, but it was also not a waste of time, because that allowed me to determine Hey, like maybe I should spend more time vetting people maybe I should spend more time making like training processes. Maybe I should spend more time investing on the team itself so that they better thrive in this environment. So a lot of things that I learned from doing things incorrectly. But yeah, there is like of course, like the trust issue. A lot of people maybe think they have to hire locally because they want to like meet the person and in person and maybe they don't think it's possible to trust you but you haven't really met in person. So yeah, I guess like I maybe have a different perspective because I've only really worked with With people overseas, at least that's where I've found success. So I'm just used to it. So it's not even a concern for me at all. And I think as long as you have the right, vetting procedures in place, the right training processes in place, that's, that's all going to come naturally without any, any serious issues. For the most part, of course, it is a learning process. So if you're not experienced with it, you probably will make mistakes initially, at least. But I found it to be. Yeah, it's, it's something that was definitely worthwhile. And my entire career has been based on on this outsource and delegation. Akua Nyame-Mensah 10:32 Yeah. So let's talk about your more recent business telesign, which is all about sort of your superpower of delegation and your interest in giving people access, I think, to to delegated work that's incredibly high quality, and incredibly efficient. And I can say this, because I was actually one of your customers. So tell us a little bit about how you built telesign And where it is now. Speaker 1 10:55 Yeah, so when I sold the previous business, I was thinking of different ideas of what I could spend my time next time. So actually, prior to selling that business, I had already kind of thought about this idea that design, a lot of my friends at the time, they were also entrepreneurs, but they couldn't necessarily afford to hire a full time designer, at least locally. And even beyond that, like for the things they wanted to do, they would require having many different designers. So not just one, like website designer or one like video designer, but they need to kind of everything for each of their products that we're launching. So they always saw like my websites and like my side projects, and like the design, so they're always reaching out, like, you know, kind of jokingly asking if they can borrow my designers. So that was kind of like an idea, like, hey, like these people, obviously need designers they know about like, you know, Fiverr, and freelancer, and I think those are great options for lots of people. But for lots of people also, it's not the best option, because these people typically won't really be partners with what you're doing, they're more so just, you know, do a single project and you know, kind of forget about you, which is definitely fine. But for what I want to do, I want to make a service in which people can get everything they needed without having to worry about hiring vetting people and all that process, I mean, it could take easily months to try to find someone then vetting them, then kind of onboarding them into your, into your system or organisation. So Delos is kind of that solution, you can just sign up and then you know, within a day or even less than that you can get your first project worked on. So instead of spending, you know, months, or whatever it is to do that process, why not just spend a couple hours to get that person on your team. So that's that's kind of what sparked the idea, I knew that there were like kind of similar services already. So that kind of validated the idea that people do want a service like this, so there wasn't too much risk. But I thought that I could provide additional value that maybe other similar services couldn't provide. So that's why I decided to launch the business. And that was I think, like Christmas of 2018, I've always pretty much 2019 is when it was founded. So about two and a half years when I exited the business. before exiting the business, it was going pretty well, there was about 70 people on the team. So about maybe 50 of the people were designers and the rest of the team was, you know, support team sales, team managers, etc. that made up the team. And towards the end, we were really focusing on scaling our hiring, because of business like design. It's a service business, essentially, although it is kind of privatised, but it's still a service business. So it's one that revenue is driven by the people on our team, the designers in this case. So often we get to a point where we'd have to pause our marketing ads, because we had too many customers. And we had to kind of catch up. Definitely a good problem, but one that we faced and that was kind of like my problem that I was solving towards the end. But thankfully towards the end, we got to a point at which you could hire pretty consistently about 10 people per month through our existing system. So yeah, it was it was going pretty smoothly. And towards the end, I was spending maybe about an hour per day on the business because of those, you know, systems was processes, the managers we had in place the managers of managers we have in place too. So it was all relatively pretty passive. From my perspective, I would just primarily focusing on strategy and how to improve those, like top level problems we had. Akua Nyame-Mensah 14:15 Yeah. And so tell us a little bit about the exit. Because I think one of the reasons why I really wanted you on my podcast, and you talked a bit about this before we started recording is you really have, I think, a unique perspective on the role that a founder CEO plays, and you have no problem you know, removing yourself when you're ready. So tell us a bit about the exit. And yeah, why? Speaker 1 14:34 Yeah, I guess there's various reasons as to why I want to exit. I guess one reason really is that because like my first business, I was kind of at the point in which I felt that I've was probably doing as much as I could and it was so much everything was pretty much delegated that I was only spending like I mentioned, maybe an hour on a bad day. So it wasn't super inspirational for me. I guess what I really enjoy doing is starting a small business So we're starting a small company from pretty much scratch and then growing that to the point at which, you know, I don't have to spend any time on it becomes, you know, pretty much passive. That's kind of what I enjoyed doing. And with Bella zine being a pretty large company already, there wasn't too much more that I felt that I could do, I think it would require a different kind of person with different specialties to really grow it beyond where it was. So I thought that it would be better overall for the team if someone else was to come in and to handle this, this existing company as to where it was. So that's kind of internally why I was thinking that, but also, I mean, for me, personally, I really do like SF income a lot. That's kind of like how I've structured all my businesses to be as passive as I can as they can based on delegation and the processes in place. So this business was like kind of perfect in that sense. But I mean, being a business owner, like, even if you're not spending time directly on the business, like you're still always thinking about it. Like, you know, when you're eating, you're probably thinking about how I can improve something. And when you're about to go to sleep, you're working on some like problem to solve, right. So even though I was only spending an hour per day, actively on the business, you know, there was many more hours in which maybe my mental capacity wasn't at full capacity, because I was like subconsciously thinking about these like potential stresses or whatever. So being able to exit the business would allow me to completely separate myself from the business, of course, and not no longer have to spend mental energy. Thinking about that business. Plus, I get like a decent amount of capital, which I can then reinvest, either in like future businesses or other investments that I'm in. So I'm pretty big on like real estate and like crypto as well, and you know, stock market stuff. So generally, I found like, I've been doing relatively pretty well with those investments. And if I can kind of like get a capital injection to those like that could only benefit me even further, especially since I'm like relatively kind of young. So I guess time is kind of on my side. So like having the time to have to let these investments play out is only kind of beneficial. So those are the things going on in my head. And that's the reason why I decided that it would be beneficial for me to exit the business. Yeah, no, I Akua Nyame-Mensah 17:03 love that. And I think this is a really great segue to talk about the new product that you're working on. And I also want to make sure that I, I mentioned, he has never taken any outside investment for any of the other businesses that he has built. And yet his new business is all about supporting people who are taking outside investment, which I think is so cool. So can you tell us a little bit about closing and sort of how it came to be and where you're looking to take it? Speaker 1 17:28 Yeah, so the new business, like you mentioned, is closing. It's a SAS type of software that allows startup founders to better manage their investors, board members and attorneys, anyone that's involved in the fundraising round. So that could be your seed round, it can be your series, A, D, whatever you are, primarily, it's focused on the startup founders that are probably getting into raising their funding rounds. So more so the seed that anybody can can work on anyone. So some context for like, why this is even a problem. So if you are raising your startup round, or your funding round, like you're probably going to spend lots of time on tedious tasks. So a lot of like phone calls a lot of like email or slack messages to different parties, like investors, other board members, and it's kind of a waste of your time, because a lot of this is not streamlined. Lawyers, you know, they bill on a an hourly rate. So they're not really optimised towards efficiency, they don't really have a huge incentive to make things more streamlined for you. And that results in you probably spending lots more time to so we're building a platform or a solution that allows us to be much more streamline kind of like an all in one platform that allows you to manage your contracts, your forms, actually sending the forms to investors, and then back to you all kind of in one place. So I'm joined in this pro in this in this software service by two other founders, both of them lawyers, and both of them, like m&a lawyers. So they work directly with exactly these kinds of deals. One of them, he focused more so on early stage investments, so you know, your seed or series A and the other investor, or the other partner in this is an attorney who focus more on like the later stage investments like series D, and even like IPOs, too, but so that's kind of like their experience. They're not really business people. So they're the ones that like, kind of created this idea from their experience of like, why am I wasting so much time doing this, like, this isn't really a good use for, for me, the attorney or for the startup founders either. So they determine like this should be a solution to be solved. And I kind of joined them because you know, I exited my business, and I have a little more free time. And they're actually my friends too. So they're pitching me this idea. And I thought that I could be a good addition to handle the operations, build a team out and do all that kind of stuff. So the website is yet closing.com. It's like closing but without the G it's still very, very early stage MVP, hopefully should be ready in about a couple of weeks, hopefully, maybe a month. We're looking for beta testers, so anyone who is interested in getting funding for their business, we don't definitely We definitely don't want help with actually finding the funding. But if you are in the process of funding your seed or a or any round, really, we're definitely a great platform or solution to help with that problem. Akua Nyame-Mensah 20:10 Yeah, is this the first time that you've actually had co founders with your businesses? The first time Speaker 1 20:14 that fingers crossed, we'll be successful. So in college, the first step I did was, I had a co founders done it. And unfortunately, it didn't become successful. But yeah, this is the first one after that, in which I have co founders, and I'm not doing things all by myself. So it's a nice change of pace. Definitely. Akua Nyame-Mensah 20:31 Yeah. So do you have any advice? You know, based on the experience that you've had so far, with building these businesses, you know, selling these businesses and sort of deciding where you want to spend your time and energy? What are maybe the top three things that you've learned, that you maybe want to share? Speaker 1 20:47 Yeah, I think the biggest thing for me has always been delegation, I always try to focus my time on what only I can do, or at least things that I can provide the most value, which I think would be the basis of delegation, really. So I guess my framework of how I think of it is, I firstly outline exactly what I'm spending time on on a daily basis, or weekly basis, or even monthly basis, I try to map out, like how much time I'm spending on those things. And then also kind of map out like how much value that's actually providing for myself or the business. So for example, like, I may have, like different columns of you know, this is like the are these are like the $5 per hour tasks. And these are like the $50 per hour tasks. And these are like the $1,000 per hour tasks that I do. And you know, oftentimes when I first started business, I'm spending a lot of time on like those $5 per hour tasks. So it makes me kind of question like, you know, why am I doing these things like, I can easily outsource that to someone else, or delegate to someone else, and then focus more on the $50 per hour tasks, or the $1,000 per hour tasks. And that's kind of how I optimise towards what should I delegate first is by making that kind of framework or that kind of like chart, and to determine, you know, what am I spending time on? And if it's mostly on the $5 per hour tasks, like I have to question myself, why am I doing that? So that was I wasn't necessarily thinking of that explicitly when I did my first business. But that was kind of like subconsciously, what I was thinking of like, why am I spending time on this test, like I'm, it's probably a waste for me to do that when I could probably spend more time on these higher value tasks. So that's probably the biggest thing that's really, I guess, shaped my career and how I got to a point in which I was able to sell my business. So I guess the second thing I would say, too, is that if you are considering selling your business, which was always kind of in the back of my head, you definitely want to make a business in which you can separate yourself from that business. So I mean, typically buyers of businesses, they don't want to buy like a job. So they don't want to buy something that requires them to spend 40 hours per week running the business, they want to buy something that for the most part can be passive, or just maybe a few hours per day at most. And at the very least, like the more so you optimise towards that the higher multiple you'll get. So you want to make me for your own sanity, probably two, you probably want to separate yourself from the business as much as you can, so that you're only focusing on like the highest level of tasks or not only the things that you yourself can do and no one else can do. But even beyond that, if you are considering selling a business, you definitely want to optimise towards separating yourself in the business. And that requires you know, delegating, having processes in place, having the structure to allow that ideally having some sort of managers so I know for like new entrepreneurs, it's may be kind of scary to hire. But it's something that you really will have to do if you want to take your business to the next level. Yeah, I guess the last thing I would say too, is, so whenever I have founded businesses that we're successful least, I always really try to optimise towards getting like real valid user feedback. So not just like feedback from your friends and family, but actual, like actual recognition that you provide value, whatever it is. So the best way to do that is to actually just sell it. So I always focus very early on on actually, you know, selling that product, even before it was like, you know, quote, ready, or perfect or whatever. Because in my first startup, the app that I tried to run like we were, we're in that kind of mindset of oh, it's not ready to be to be shipped yet. Like it's not great enough to show it to people. So we didn't really get too much feedback early on, we were also kind of in the the false mindset of like trying to hide our idea because we thought the idea was really valuable. And we didn't want to get stolen or something like that. So all things that really hindered us. Whereas if we had instead tried to get real feedback by you know, getting people to sign up for a waitlist early on, or I mean it wasn't as relevant for that business but you know, getting like paid people to sign up. Like that would have been much better feedback than just saying to our friends like hey, this is our idea and then being positive about it, but of course they had to because they were our friends so I'd say as soon as possible try to sell even if you just means like making a landing page or if you're building a product like having a Kickstarter, whatever, but just some way to get like real feedback. Real validation from people that you don't have any like personal connection with I think is extremely crucial as you're building new business. because you last thing you want to do is spend months or even years building some product that no one really finds valuable. Akua Nyame-Mensah 25:06 Amazing. Thank you so much for sharing those three. And I think the only thing that I also want to know is who is Kenny outside of his business and outside of his investments? Speaker 1 25:15 Yeah, that's a good question. Um, I love staying active. So, I mean, anything I could do to like exercise, you know, play sports, go to the beach, and definitely all about that. Yeah, I mean, I guess this is kind of business too. But I'm pretty heavily involved in real estate. Now. That's one of the things I want to get more involved into. So I have a few like, out of state properties that I have that are just pretty passive. I have property managers in place that handle that. So I think like, maybe sounds a little weird, but like, I do enjoy business things. So like a lot of my life, even outside of like, what I'm working on full time is still like, somewhat business related. I like the idea of delegation, passive income in general. So I'm always trying to optimise my life to towards being more optimal. And whatever I do is so it kind of a boring answer, but not not definitely taking up lots of my time. So don't have too much time for other things, either. But, yeah, just staying active whenever I can. Akua Nyame-Mensah 26:07 I love it. Well, this has been absolutely great. Thank you so much for sharing your insight, your advice, your experience, where can people find out more about what you do? And about your businesses online? Speaker 1 26:20 Yeah, so I am fairly active on LinkedIn. So that's a great, great place to connect with me. I'm more than happy to connect with anyone offer a you know, free advice for you help whatever I can to help out. I enjoy working on businesses, business ideas, and trying to like solve problems. So yeah, it's honestly fun for me to do so happy to connect, and of course, help out as best I can. For anyone that thinks I can be of help. I want to get more active on Twitter. I know it's a great platform to really connect with people, but I haven't so far. But you can find me on Twitter, just search my name. And you'll probably find me. Those are probably the best ways to do that. Akua Nyame-Mensah 26:56 Right? Yeah. And I'll make sure they're in the they're in the show notes. Awesome. All right. Well, thank you so much for joining me today. I really appreciate Unknown Speaker 27:01 it, Kenny. Yeah, my pleasure. Thanks for having me. Akua Nyame-Mensah 27:04 Thank you so much for taking the time to listen to today's episode. If you enjoyed what you heard today, please share it with your friends. We can continue this conversation on social media the links to my socials so that is LinkedIn, Instagram and Twitter. You can find them in the show notes. If you tagged me in a story and include the hashtag hashtag ask Akua I will share a special little gift with you. Thank you so much once again for your time and I cannot wait to share my next episode with you stay safe and sane.


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