Build Quiet. Lead Bold. The Mindset Behind Legacy-Driven Success

Not every entrepreneur wants to go viral; some are building for the long game. In this powerful episode of Shine On Success, host Dionne Malush sits down with a young founder who’s defied the noise and built multiple companies by focusing on what matters most: legacy, leadership, and doing the work. 

They dive deep into what it really takes to grow, scale, and sell a business, including the emotional toll, mindset shifts, and the hard decisions behind the scenes. Whether you're starting out or scaling up, this conversation is packed with real talk, honest reflection, and refreshing perspective. It’s a must-listen for any entrepreneur tired of the hype and hungry to build something that lasts.

Connect with Jordan here:

Website: https://www.jordancalderon.me/

Instagram: https://www.instagram.com/itsjordancalderon/

LinkedIn: https://www.linkedin.com/in/jordan-a-calderon/

Transcript

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Introduction to Jordan Calderon

Speaker 1 0:02

Not every entrepreneur wants to be the loudest in the room . Some just want to build something that lasts . Today's guest is proof that strategy beats spotlight . Jordan Calderon is a two-times exited founder , TEDx speaker and the president of StratDev , a top 100 marketing firm that's helped generate over $150 million in client revenue . He's built a national college apparel company , launched a wine brand and walked away from buyout offers most people would grab in a second . Why ? Because he's not chasing attention , he's building legacy . So , Jordan , welcome to Shine on Success . How are you doing today ?

Speaker 2 0:34

I'm doing fantastic , and even better after that rock star introduction .

Speaker 1 0:40

You're the rock star . I'm just the one creating the good stuff , but yeah , it's impressive that what you're doing . So I always like to start with this question what's one thing you'd love people to know about you that they wouldn't find on your bio ?

Speaker 2 0:52

You know what ? That's a fantastic question . I am inherently lazy as an entrepreneur . The reason why I work so hard and for the audience that doesn't know , I'm 26 years old the reason why I work so hard is so I can live out my dreams of being lazy when I'm 40 , 45 , 50 years old . So , while all my other friends are making the most of the ever made , ever right , I'm on the beach sipping Mai Tais and Bora Bora . That sounds like life worth living to me .

Speaker 1 1:19

So yeah , Hopefully you're sipping some of that wine that you've .

Speaker 2 1:24

That's right .

Speaker 1 1:26

Sounds so exciting and you know I'm almost . You said 20 . How old did you say 26 ?

Speaker 2 1:31

26 . That's right .

Speaker 1 1:32

I'm literally 31 years older than you . I am in that space where I'm doing everything I can to make the most I can because I'm on the other side of my life , right . So that's amazing . So I'm so excited for you and for me to get to know you . So you've already exited two companies . What's one thing nobody tells you about ? Building and then selling a business ?

Creating a Sellable Business

Speaker 2 2:03

You know , I have had a lot of friends who have attempted to sell their business and found themselves in the 11th hour of an acquisition just to find out that there's something called a retrace , which means an adjustment into costs that end up turning into a price that they don't want to take and therefore the deal doesn't go through .

Speaker 2 2:11

The business ends up dying and they leave with nothing .

Speaker 2 2:14

Most recently , I actually heard that there was a retrace from a $50 million purchase price all the way down to $1 million .

Speaker 2 2:21

That's crazy to lose throughout a negotiation in terms of valuation , but the way that I've been able to prevent that was actually through one of my mentors really wise words to me , which is about six months before I sold my first business . They came to me and essentially told me to , instead of trying to sell your business , when you decide to sell your business , before you decide to sell , work on creating a sellable business . Right , to create a sellable business rather than try to sell your business . And so what that does did is what it essentially forced me to think in the lens of what a prospective buyer would look for Right . Ok , they want consistency , they want growth , they want a really stable organization , they want really clean operations , no-transcript , and so building that sellable business has allowed me to essentially ensure that I am creating the right types of opportunities for the right types of buyers , attracting the right types of buyers for that matter as well , and ultimately , leading with myself , getting the best purchase price and exit I possibly can as a founder .

Speaker 1 3:49

I love that . That's great information . I really never thought about it that way . And , owning a business myself , you know , inevitably , if I told you I'm 57 , like 10 years from now , I might be at that position that I want to sell . So I need to prepare to sell it now , right , instead of waiting to say , okay , one day we're going to sell but we haven't prepared . That's great advice . So take me back to where your entrepreneurial journey really began , and what was the first moment where you said I'm

The Entrepreneurial Journey Begins

Speaker 1 4:14

doing this ?

Speaker 2 4:14

Yeah , yeah , you know , I remember it actually very clearly 2017 , I was 20 or 18 years old 18 .

Speaker 1 4:21

Yeah .

Speaker 2 4:23

I just did math there . 18 years old , I just got into college at UC Santa Barbara and had a little bit of a Justin Bieber haircut .

Speaker 2 4:30

My hair is actually quite long right now , but imagine it was much longer . I walked into my first econ class , I flipped my hair and I sat down and had the biggest smile on my face , ready to learn as much as I possibly could about economics . And I started listening to the teacher , the professor , and hearing him speak about all these theoretical things , and I realized very quickly , oh my goodness , I thought I was going to learn something that I could take home or take to my dorm room that night and apply in stocks and business and whatever it might be . But instead what I got was something very , very , very theoretical that I really couldn't directly apply to anything other than maybe being an economics professor . And so I realized in that moment , or at least by the 90th minute of that class , that I did not want to work four years just to start an entry level job and not use my degree at all for that , for that , for that entry level job . So I went back to my dorm room that night and I came in with the plan . I said you know what ? I'm going to go create my own career . And so I looked up what was hot , what was popping back in 2017 .

Speaker 2 5:33

And back then , something called dropshipping was Essentially that model for those that don't know is when you sell an e-commerce product that's not yours but a Chinese supplier . Usually the Chinese supplier will then go ship out the products to your customer once the customer buys it from you . So you don't touch the product yourself , you don't have to hold on to any inventory , and that's usually the most costly part of an e-commerce company . So all you basically do is market their company , slap your label on it and boom . The idea was make a couple million dollars , right . But as any 18 year old theyyear-old , I didn't realize how much work goes into making your first dollar . So I don't know . I probably put a couple hundred dollars into my first company dropshipping company that night .

Speaker 2 6:12

I lost it in a couple of days , shut it down . I said , okay , this isn't for me , but something kept drawing me back to it . And so I tried my hand again at a different dropshipping store and it failed again . And then I tried my hand again for the third time and it failed again . The fourth time I said , okay , you know what ? Maybe drop shipping isn't for me , but I really like the idea of e-commerce . I'm really comfortable with the Shopify platform . I now know how to run some ads , I know how to create an SEO blog . What can I do in e-commerce that I think I can do much better ? And so I actually started to give it some thought .

Speaker 2 6:48

And I was in college , I was a freshman , I was making 20 friends a day and I asked all of them . I said , hey , what's a product that you really want , really need ? And we all agreed that creating a design or apparel for your university that actually resembled the student culture and camaraderie , rather than just university lettering , established 1872 or whatever it is right is , is what people wanted . And so that was the inception of my , my first real company called college clout , uh , where we made custom designs for fraternity , sororities , clubs and organizations , and that was the inception of my , my , my entrepreneurship so do you still have that company ?

Speaker 2 7:15

I sold it , uh , back in 2021 to uh greek house , uh , which was the biggest competitor in that time , which wasn't too massive by any means . Um , they're much smaller Luke McGurran and Karthik Shanadi . They ended up actually selling that business to University Tees , which is a massive organization . If you have any children or of the like that went to college over the past decade , if you look at the back tag of their t-shirt , it'll likely say University Tees , so very , very big . And now Luke and Karthik are doing Athletes Thread , which is , if you're familiar with the NIL rules a couple of years ago . Now college kids can monetize their ability to sell their merchandise and things like that .

Speaker 1 7:54

Oh , that's cool . I did not know that .

Speaker 2 7:56

Yeah , so Athletes Thread has made more than a couple of millionaires in that space and it's been very cool to see . I mean , they've made some pretty big headliners as as a company too . So it was , it was a good , successful uh exit for , I think , all parties involved .

Speaker 1 8:09

Cool . So , as an entrepreneur , have you ever hit a wall so hard that you almost quit ?

Speaker 2 8:13

Dude every single day .

Speaker 1 8:15

I thought just because you're young doesn't mean you don't have to hit these walls right .

Speaker 2 8:21

Oh , my goodness . I think the beauty of being an entrepreneurship

Hitting Walls and Bouncing Back

Speaker 2 8:25

is that you hit walls every single day , and for that same reason , I don't think that everybody should be an entrepreneur , because it's so much decision-making . You have to really believe in yourself . My girlfriend said this a couple of days ago . She said decision fatigue , where you're making 50 decisions , 500 decisions , 5,000 decisions every single day , hoping that every single decision that you make is right and having the confidence to believe that that is right . And so I do that . I probably make a couple hundred decisions every single day that just are on autopilot for me , but I feel like I have the answer and therefore I make the decision . And you know , I think it's just a lot of left , right , left , right , left , right , left , right . That gets us to the point of being able to get there . But you know , I hit walls all the time , right , and so it's left , right , left , right , left oh , that's not the right way . Let's go right , right , oh , that's not the right way . And just keep going back and forth like a ping pong ball until you find that .

Speaker 2 9:17

Does that take a toll on me ? Absolutely Right . Are there days that I want to quit ? Absolutely . Are there days that I'm just super out of it or just don't want to deal with . You know , a mess that I made myself , absolutely . But what keeps me going and what keeps me driving is the fact that it's not just me . I put food on people's tables , family's tables , and a lot of people for that matter as well . You know Strativ alone , which is my current company , I probably feed 50 families at this point . So with that , you know , my failures are not just my failures . My failures are you know , could be detrimental .

Speaker 2 9:49

It could be the difference of food on someone's table or not . So , yeah , do I want to give up ? Absolutely , sometimes , absolutely . Am I going to give up ? Hell , no .

Speaker 1 9:56

Good Cause . There's a lot of people your age that aren't even started yet . So you're you're helping . Shifts had to happen for you to keep leaving at this level Because you are 26, . You could just go and be with your buddies and have fun all the time , like how do you , what do you do inside your own head to do it ? Now , you said you like the lazy idea , but that's going to come later on , right , because you're going to do it earlier than most people , so you're going to have a great rest of your life . But right now , what kind of mind shift happens with you ?

Speaker 2 10:26

That's a phenomenal question . I let my calendar dictate a lot of things that I do . If you look at my calendar , your jaw would drop because there is no white space on it . But I block everything out for business , but I also block things out for fun as well . I do my best to have a good work-life balance and not hit burnout .

Speaker 2 10:45

I've hit burnout many times before . I don't like it . I don't want to experience that if I can avoid it again . And so I block out , for example , breaks , or I block out time with buddies , or I block out 26 year old things . You know , go get drunk on a Friday night , whatever that looks like , but I block it out to make sure that I actually go and do it and I'm , you know , kind of code switching to be able to fully get into that as well , rather than trying to , you know , go out to a bar and be responding to emails at the bar too , because I'm you know a meeting was 20 minutes before that . So , with that said , that idea of time blocking is , you know , as old , for has been , has been around for quite some time . Elon Musk actually repopularized it as of recently because he does the same thing , but it's been around for much longer than I think he has . But yeah , I've adopted it and it's worked quite well for me .

Speaker 1 11:30

I'm the same as you . I schedule everything and it's really important , but I can feel right now like I'm in that midst of burnout mentally . You know . So my husband had a liver transplant nine weeks ago , so I've been caretaking at home , still running my company , you know , on the side , while you know my staff is still there every day and my partner's there , all you know , my staff is still there every day and my partner's there .

Speaker 1 11:48

But it's been a , it's been a lot and I you think , like you're working at home , maybe you'll be relaxed , but I'm , I'm not and I feel that . So you know , here's the thing I will always get back up . I know that because I've been on my ass plenty of times and you know I'm here in the middle of one of the hardest things I've ever had to deal with and I'm still working and I'm still doing this stuff right . I wish that I could relax and five years from now I'd be able to retire , but that probably won't happen because it's just who I am , the nature of me . But I'm impressed by you . It's really cool what you're doing and you know , mindset is a critical part of it , because a lot of people don't get back up and they stay in that space and I just I don't want to . I want to always be that person that bounces back . As you get older , it does get harder , I have to tell you . It does get harder to keep bouncing .

Speaker 2 12:32

My knees crack whenever I squat now , so I believe I believe it'll get worse . I believe you , I'm right there with you . I think that , though , really separates , you know , I think , the non-entrepreneurs versus the entrepreneurs . And , by the way , I don't think there's anything wrong with not being an entrepreneur . I actually think that being a nine to five worker works best for most people , right , it's ? It's less stressful , there's , you know , less less risk , there's more consistency in your life and as long as you can , you know , make enough support of family , it's , it's a guaranteed paycheck and being an entrepreneur , you don't have any of those things right .

Speaker 2 13:07

You're living life on the edge at all times , and so you know , for those that find themselves , you know , getting knocked down in entrepreneurship and don't really want to get back up , that might be a calling and you know , a telling sign that you know the nine to five might be better for you . And , again , there's nothing wrong with that . I think over the past couple of years five years , call it entrepreneurship has really been glorified , you know , back when , you know in 2020 , when everyone was like , oh great , start a hobby , everyone turned that into being an entrepreneur and if you're not an entrepreneur , you're doing something wrong . I so disagree with that mentality .

Speaker 1 13:36

I think it's so toxic and everyone's not meant for this at all . I mean , there's a thousand percent .

Speaker 1 13:41

Just not . And what you said earlier about you know , always look at it differently . And one thing I learned just from personal development seeking expert counsel is one of the most important things that I've done in my own business , where I went to people that did what I do . I didn't go learn from someone that never stood in my shoes . You know , and I think that's what you saw that day was that same feeling that I have .

Speaker 1 14:06

You need to learn from other people that are successful in the field that I'm watching you thinking I just read up here that you were like marketing . You're a top 100 marketing firm . I could learn a lot from you , and I've been doing this for a long time . Right , I've been in the real estate for 21 years . I've owned the brokerage for eight . We have 205 agents . I want to grow so much and I am like stuck right now I cannot bust through it . So that brought me to my next question about working smarter and not louder . You talk about that . So what does that look like in a world obsessed with going

Working Smarter, Not Louder

Speaker 1 14:40

viral ? Because every day I'm learning about what I should be doing on social media this one , that one making videos and I'm like , oh my gosh , none of it's working videos and I'm like , oh my gosh , none of it's working .

Speaker 2 14:51

That's a that's also a good question . You obviously came very prepared . I love it . I think , at least for me , and I don't know if this is the right answer or not , but it's right answer . Right answer for me , it is making sure that I stay my course .

Speaker 2 15:05

And yes , there are there's so many different gurus out there , or , or , or YouTube , or Tik TOK videos that will say do this , do that , do that Right , and if you go try it all , you're going to be successful at none . I'm sure that some of them work right , but if you try to do 10 things at once , or or , or or change direction every single time that you see something else , it's like shiny , it's like the shiny object syndrome , right , you're not going to go anywhere . So you know I I hear all the time I have other entrepreneur friends that are 10 times cooler and more successful than me , but you know they'll come and basically say , yeah , for example , like a couple of weeks ago , one of my buddies made over $10 million in a cryptocurrency and I look at that being like , yeah , that's really cool . And maybe two years ago , three years ago , I would have been like okay , teach me everything that you can about this one thing about cryptocurrency , so I can go try to emulate it and do it myself . But then , if I do that , it would have distracted me on everything that I've done so far and I would not have been able to grow the way that I've been able to over the past two years , if I just ditch what I was doing here and then not .

Speaker 2 16:03

The second thing is , if I don't know enough about it , it's because I'm . It's kind of too good to be true . Right , there's , I'm sure , a lot of adversity that my friend had had to go through just to get to that number . You're just hearing about him at the top of the mountain , but you're forgetting about the climb to get there . Right , I know that because I've climbed a lot of mountains . And the last thing is right , I know what I'm good at . I don't know what I'm not good at and I'm not going to go try it . I think I figured out where my footing is and I'm going to go and climb the mountains that I feel best and most confident to climb . So I'm doing good with what I'm doing here . Do I hear about other people climbing faster , you know , mountains faster , or mountains that might be bigger than mine ? Yeah , but that's not going to change my direction .

Speaker 1 16:44

Basically , you're saying stay in the lane stay in your lane .

Speaker 2 16:46

Stay in your lane , go shiny over here , right , but put blinders on like a , like a horse , just go straight .

Speaker 1 16:52

I definitely know how that feels . In my best year of my real estate , when I was a practicing real estate agent which I'm not anymore I actually that was the thing I used to say I'm putting horse blinders on so like get out of my way , right ? So I literally was having my best year of my career . I closed like 78 transactions I share as an individual agent . That's a lot , because most agents delegate to 12 . So I did that and then in the fall , I got a call from one of the new Pittsburgh Penguins that was joining our team . His agent there called me because he looked and found me on social media and thought I was a perfect fit . So I sold my biggest house ever to a really cool guy .

Speaker 1 17:24

And then my personal life was falling apart . And then my Achilles ruptured in the same year . So like it was like this craziness , like I'm having the best year of my career and everything else was falling apart . How do you stop that from happening ? How do you have your ? You're in your lane and working like crazy . You know you don't . You don't have kids yet , right ?

Speaker 2 17:41

No , no kids .

Speaker 1 17:42

I don't have kids either , so I was a hundred percent working on work , right , but then everything was falling apart around me . How do you not get there ? And if you are on your way there , it's not fun .

Speaker 2 17:51

I'm going to tell you that yeah , yeah , yeah , stopping and smelling the roses along the way , right to path . And , like you said , you got to put on blinders , but you also have to be aware that you have blinders on as well . There's a phrase that my young entrepreneur's friend used called monk monk mode , where they essentially just lock themselves in a room for like 16 hours a day . Maybe they'll go out to the gym for one hour and come back , and I don't hear from them for like six months , and I'm sure that everyone at like the world isn't hearing from this person . I don't feel bad , it's not just me , but I think that that is also detrimental , because maybe they achieve some level of success right , and they're . They're .

Speaker 2 18:25

Essentially the goal of it is to fast track , but at least to me , right , you're wasting six months of your life , right , like I'm busy as hell too , but I'm in New York right now . Right , I'm going to be busy as hell in New York and go enjoy myself while I'm at it , and I go downstairs and have the best pizza of my life and come back up and continue on , right , so you know , with that , I think you just got to stop and smell the roses . You got it , you got to . You know . Enjoy the fruits of your labor at some point , too . Right ? You're working so hard for a reason , right , if you're not an entrepreneur is not a blessing , it's a curse . I truly believe , right , go , go , enjoy the freedom that you signed up for . That's the reason why most people want to be entrepreneurs in the first place .

Speaker 1 19:00

And what you said about the blinders makes sense to me . So I was blind to everything . I was focused on business , but I was blind to everything else too . So you know , you definitely want to have that balance and I agree you should smell the roses . That's a big thing . While you're in New York , I'm going to tell you you need to go to Lombardi's on Spring Street . That's the best pizza I've ever eaten in my life . In fact , we were there for three days last well , six months ago and we went there three times .

Speaker 2 19:30

So I will check it out . We need to find a place to eat tonight , so I definitely will . And I also do want to add I , you know , with , with that said , like I definitely sometimes go fast , I mean I'm , I'm , I'm preaching as if I've learned this lesson . I want to make clear to the audience I am learning this lesson . So I'm talking to you , I'm talking to your audience , but I'm also talking to myself , and I say this too I , I , I very much find myself holy crap . It's been three months and I haven't looked back . Maybe I should just slow it down for a second . There's definitely those periods of time that happens and I come to that realization . So self-awareness , I think , goes very far , not just in the business world , but just in life as a whole .

Speaker 1 20:01

So for someone that's listening and that wants to scale their business and I'm one of those people

Growth Strategies and Life Lessons

Speaker 1 20:05

. I'm still in that , wanting to scale . What's the biggest mistake you see founders make when it comes to growth strategies ?

Speaker 2 20:10

Not doing it , being in analysis , paralysis , where they just want to optimize , optimize , optimize , optimize , optimize , before they actually go and do it . I'm so much more of a doer than anything . I just jump off that cliff , see what happens and veer and change direction as much as you can . It's the same mentality of you're going to miss 100% of the shots that you don't take right , and it takes a lot of iterations . The first , fourth , tenth , hundredth time sometimes is not the right thing . I'll leave you with the story . Do you know the cleaning products ? It's a multi-purpose cleaner called 409 .

Speaker 1 20:40

Yeah , yeah , for sure .

Speaker 2 20:41

Do you know why it's called 409 ? No , because the first time , the second time , the third time , the 407th time , the 408th time the solution to make the best multi-service cleaner in the world Scientists that made the product didn't work . But on the 409th try , he ended up creating the product that he was finally happy with , and so he named the product after his 408 failures , and that's why it's called 409 . So it takes sometimes 409 iterations , and so just do it . The faster that you just go and do it , the faster you're going to get to your 409 try , which is might be your successful one , you know that's amazing .

Speaker 1 21:15

I had no idea , but I do know about edison and the light bulb .

Speaker 2 21:17

There's a lot of tries right and kentucky fried chicken yeah , yeah , look look at the back of your four after the podcast . Look at the back of your 409 bottle . Actually says the story on the bottle too .

Speaker 1 21:27

It does .

Speaker 2 21:28

Most people don't read the back of Nick Masubis . Maybe I'm a psychopath for that , but I didn't . I'm like well , that's great .

Speaker 1 21:36

So let me end with this last question , which I think is great . You're 26 . What would you say to the younger version of you who is just starting out Because there's a lot of people at 18 , 20 years old that want to try to be an entrepreneur or what's the biggest lesson that it's taught you about life ? Maybe let's spin it that way .

Speaker 2 21:52

Treat people how you want to be treated . One thing that's gone really far . It's not like a lesson I've learned . I started from day one like this , but it's been tremendously helpful . I have rarely , rarely , rarely had any team members leave or quit . I've actually never had a team member quit , thank God for any of my companies . People have left because of health reasons , because it's the next part of their career journey . You know things like that , but never because they didn't enjoy the community and the culture that I built at my companies .

Speaker 2 22:19

Whether you have a service-based company , a product-based company , any company for that matter as well , your employees , your team members , are the heart and the brain of your business , and without those two , you have no business . If everyone gets up and leaves , you have no business , and so you want to really treat these people really well . I have so many of our teammates come to me with you know . New teammates come to me with horror stories saying oh yeah , my boss was an a-hole and they're telling me as their boss this . Right , there has to be a level of comfortability for for for them to tell me this , but I've only heard good things . You know , all my companies have had amazing reviews on , like Glassdoor , never solicited a review , and I think that that's a good gauge of you know what people are thinking Glass people say some nasty stuff about their bosses on Glassdoor , so you know that that that has been super helpful .

Speaker 2 23:02

With that said , though , it is also important that you have the right team members in place , so I guess a lesson that I would tell myself is be careful with who you hire . For a while , I was really bad at hiring the right people . I've got my footing . I've gotten much better at it over the past couple of uh years , but you know and all the opposite of that , you know fire quickly if , if something feels wrong , it likely is give people a second chance , give people a third , but don't give people a 20th , and and sometimes it just sounds easier to lead people in just rip the band-aid off . I promise that it'll . It'll help your business . The opportunity cost of a bad person being in your business , if you actually look at the numbers , is like astronomical . You know , having the wrong person in the business can cost you truly millions of dollars . So , yeah , that's a lesson I would tell myself .

Speaker 1 23:42

So thank you for being on here with me . This kind of conversation actually helps people move forward , I think , when they listen and they hear someone that's 57 talking to someone that's 26 , and there's a lot of similarities , right , and you're young and learning , but I've learned a lot too , so I've you know , I've had 30 years of learning in the entrepreneur world , so thank you for sharing that with me .

Speaker 2 24:02

How can people get ahold of you ? Yeah , go to my personal website , jordancalderonme . There you can find all of the companies , businesses and projects that I'm working on . You can find my LinkedIn . You can find my personal Instagram . If you want to see the cool food and the Lombardi pizza that I'll be eating at the end of this podcast , I'll probably put on my Instagram . And then I just joined Twitter as well . I think I have like seven followers , so whoever's out there if you want to be my eighth follower ? Jordancalderonme .

Speaker 1 24:27

Thank you for being on here with me , so for everyone listening . If this episode sparked something in you , please share it with one person , because if it helped you , it may help exactly one other person , and we would be thrilled . Our goal here at Shine On Success is to help millions of people , so we have to start now . We have to keep sharing it . So thank you , jordan , it was a pleasure meeting you . I hope you enjoy pizza in New York City as much as I do , and if you ever come to Pittsburgh , I'd love to meet you .

Speaker 2 24:49

Amazing Likewise , and thank you so much for having me on .