Techstars Accelerator Mentor Madness Reflection

This is is part of my live-learning series! I will be updating this post as I continue through my journey. I apologize for any grammatical errors or incoherent thoughts. This is a practice to help me share things that are valuable without falling apart from the pressure of perfection. 

Episode Summary

– It is a lot of talking, information processing and stimulation
– Feeling quite tired after all of it especially when some responsibility is on you to speak and lead conversations
– 3 weeks straight of six 25-minute meetings with 72 mentors overall
– Great opportunity to refine your personal and company introduction
– Because mentors come from different backgrounds you need to be concise
– Some mentors may be more relevant to you than others but all can provide value
– The companies excelling at Mentor Madness are sending out emails before with agendas and introductions
– It is important to follow up with mentors after the conversation to thank them and drive any call-to-actions
– The recommendation is to include mentors in your monthly or weekly updates as you progress through the Techstars Program
– While they are important, our CTO Vatsal Shah at Speak Ai has had to take care of some development-related tasks and has had to prioritize that over some of the calls
– Very quickly we realized we needed to ground the conversation in a real customer case study
– Sometimes you will get recommendations that do not make sense because of your own knowledge of the space, market and competitive landscape
– I’ve been asking mentors at the beginning the best way to make the time worthwhile but most do not have a structure they would like to follow
– You are supposed to identify 3 to 5 lead mentors from the 72 mentors you connect with to help you throughout the remainder of the program and after
– The Airtable with the contact information of mentors is super helpful for preparing and following up
– We have gotten some good feedback about our executive summary including call-to-actions
– We hope to improve with better agendas, asks, and follow-ups


Product vs sales-led growth
Is this a today problem?
Mentor versus investor versus a prospective customer
A lot of different perspectives on fundraising
Narrowing focus is one of the most common feedback
Clarity on what you want to achieve personally and professionally is required
Is what you are doing compounding?

YouTube Video


Techstars Toronto Accelerator
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Techstars Toronto Accelerator Mentor Madness Thank You
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Techstars Mentor Madness
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Founder advice for Techstars Mentor Madness | Landon Howell
Reflecting on the madness (of Techstars Mentor Madness) | by Hugh Geiger | | Medium


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Automated Transcription

Hello, hello. Tyler Bryden here. I hope everything’s going well. You’ve come across this channel, you know, make videos on a wide range of topics. One of the interesting things going on in my life right now is being part of this Techstars Toronto accelerator. So basically if you don’t know what that is, it is an accelerator program for companies that show some traction, some sign that success is an outcome that is possible and they invest some money like 120,000 USD and generally throughout that program. They support you, you’re in with say 11:50 other companies. You work closely with those you grow the business, you track the success and overall become part of this community of I think around 3000 or so companies that have done Techstars before. So amazing community, amazing group of people who are passionate about growing businesses, passionate about technology and really want to do their best to help.

Maybe people who are earlier on their journeys find success on on that journey which can be super difficult, super rewarding, but also full of obstacles, full of challenges, both real ones, some mental and in in that journey support is often required. And So what I wanted to talk about today was something specific, which is basically this idea of Techstars mentor madness and for those who haven’t heard of Techstars or. Probably heard of Mentor Madness. Basically what it is is a matchmaking homo speed networking. Sort of setup that takes place over a span of three weeks and in that three weeks you meet like 72 and we meet like 72 mentors overall and so.

It’s laid out, they break it in for the for for context, it’s like say there’s twelve companies in our cohort here in Toronto and this is happening in parallel all across the world at Techstars everywhere. They’re going to split you up into morning, split you up into afternoon sessions and then you’re going to meet 25 minutes with the mentor 5 minute break and then another 25 minutes and you’re going to do that six times per day for three weeks. So basically 3 hours a day during that, you know, during that year. You know, these people who are mentors come from a wide range of, you know, expertise and skill sets and backgrounds. And I’ve actually got a post here on LinkedIn if you’re interested in who some of these people are. You can see that tech stars did a nice post just to sort of summarize and wrap this up and say thank you. You can check out some of the people who are mentors in it. They ran out of space in the post, and then they’ve got lots more down here. And, you know, overall a very incredible, inspiring and ambitious lineup of people.

Who in generally seem to have the best interest. Of people who are part of Techstars in mind. And I think there is some, you know, side benefits of saying that you’re a Techstars mentor. There’s credibility, you get to learn a lot and it’s probably very inspiring to talk to so many different people who are on their own journey. And then from an investment perspective, it gives you this idea of deal flow, meaning that you’re getting early looks at companies that may become successful. And if you’re looking to invest money, whether it’s an Angel investor or through more institutional investment, that you’re getting an early look.

At some of the companies that basically tech starts his pre vetted for you. So I think there’s a combination of reasons why mentor stuff like why mentors join sort of tech star and then become part of it because it’s pretty grueling. I think their mentors themselves are taking on like 2 sessions so they’re meeting at least 12 companies and then were as someone going through the cohort we’re meeting at around 72 people that three hours a day is definitely you know we got a chance to meet with everyone I get together in person. After, because the mentor Madness had taken place place online, everyone was very overwhelmed. Very.

You know, just inundated with information and opinions. This idea of mentor whiplash, where one mentor is saying one thing based on their personal experience and another one is saying another. And overall there’s this sort of weird 25 minute time frame where you can get to know each other a little bit, but there’s not much you can really give beyond sort of somewhat general advice or at least advice coming through them. That experience and that experience could be bucketed into maybe it was, you know, a while ago and things have changed. Maybe it wasn’t a different vertical or industry or space.

And so all of it has a little bit different shades of being directly applicable to what your business is doing and maybe the support and the advice that you need on your on your sort of journey as you’re going through and everything that’s going on in the world today. And I will say like overall, you know, I’ll give some actually very, I think more concrete takeaways apart right through this video. But a couple of sort of things that stuck out to me is just how tired you felt after those conversations and it was sort of this cognitive load that you’re having this isn’t. Tuning into a call where you’re sitting and. You know, maybe have your your camera off and you’re listening the background and typing things. This is like, no, you’re just staring one-on-one with two, you know, with a person whose time is very worthwhile. They’ve got many things they volunteered their time and you know, if you leverage them the right way, they can give you great advice. They could introduce you to possible customers or investors. They could invest themselves. And so that brings a lot of sort of pressure and intensity into that call. And they used to do all of these mentor madness meetings in person, but that’s no longer the most practical thing with.

Everything going on. So that’s through zoom, which I think actually makes the process, you know, very sort of streamlined. But I also think you end up, you know, just staring at a screen all day and has an impact on your eyes. And in a way it also reduces the the the stimuli in a little bit of a way where if you’re sitting down, you’re standing talking to someone, there are things that you’re picking up on that you’re not picking up on in a zoom call kind of thing. So lots of different structures. I would always ask people like, hey, is there if you found a structure or a way to like make this most worthwhile?

Generally the answer was no. Introduce yourself, maybe you give me, you know, where you are today, why you started this business and then what’s challenging you most. And then that would be sort of the groundwork of where we would then build from. And I think generally it was helpful to. I do a little bit of pre work on them. Tech stars was nice enough to stand out basically like an air table with a lot of information with LinkedIn, with emails, with context on who they are, why they’re part of Techstars mentor group. And then you can use that to then even hone on ones who I think you have even more tailored conversations with or who you might see as a more leading mentor or who you might see us up investor or prospective customer, something like that. So lots of different ways to sort of filter through these kinds of people to then maximize the value not just for you but for them as well.

And I think that’s something that felt, you know very onerous on you as a tech startup company was how do we make this time worthwhile and make sure that your experience as a mentor is good, although their experience is the opposite. How can they make sure our time is good. And it was very obvious from the conversations that they were trying to facilitate that to happen. So couple notes on like how did companies that, how did companies. Excel in Mentor madness. So it was ones who did the pre work, I would say ones who did an e-mail before. We didn’t do that the first week and I felt the conversations were a little bit unfocused and unguided. And then we actually had a monthly update e-mail that we sent in. I actually did more personalized version to the upcoming tech stars mentors and then the ones I previously met and I got some really good feedback because I had sort of made that touch point with them. They knew a bit about us and then they had sort of a a thought process sort of filtering.

In the background, so when we actually got to meet a little bit more meaningful, worthwhile conversations could happen. So that was definitely one of the bigger ones. The form of feedback, just as a note that I was really happy to get was in our executive summary that was sent to these people before and they looked at them, but they’re glossing over a lot of different companies sheets was that we actually had a call to action. Basically, here’s how you can help or here’s how you can contribute. And we’ve got multiple feedback from mentors that that we were one of the only companies who put that in. And that’s sort of that marketing sales mindset if you don’t.

And I called action. They don’t really know how they can contribute. So if you’re ever sending out documentation or just anything in life, add a call to action if it makes sense. That can really be a meaningful differentiator from, you know, great information, but not sort of mobilizing the person at the end of that information to do something meaningful. So the other people also, I think this is now taking place now because it was so busy, but are now following up with mentors. So I don’t think you can follow up personally with every single one of them, like in the Super personalized way unless you’re spending.

You know, your whole day doing that, but I think picking your safe top five to 10 that you have really great conversation with and reaching back out to them and saying, hey, I’ve really enjoyed this. I’d love to continue the conversation and here’s based on our conversation, what would be valuable explore investments or relationships or customer opportunities, whatever that actually is. And so you know, I think the other thing is. In that they were recommended to send out weekly or monthly updates after we’re on a monthly cadence. I enjoy that cadence. I think weekly is not think weekly is too much. You inundate people. I get enough information that as it is and there’s not that much transfer, you know, transforming on a weekly basis that I’d like to summarize and send at the end of the week. So we’ll continue with the monthly schedule, but that’s one way to then mobilize these relationships that you’ve met and I think is a worthwhile recommendation if you can hit that cadence and enough is transforming quickly.

Couple other things are. I think we had to split the time in some instances, so. That’s all the CTO Spki you know is head down. It’s on some big sort of architecture changes with this system as well as some sort of feature development and some solutioning for some customers and you know that’s super valuable worthwhile things. And then on my side I’m doing some marketing activities. I’m actually doing sort of customer onboarding or relationships and those are super, super meaningful and when you’re just stuck with these three hour blocks you know every afternoon for three weeks you have to sort of prioritize and so there was multiple times I said that’s.

You take this, you know, you go do the work that you need to do. I’ll take these two days. And then you know, being the sort of CEO and the person who talks a lot, I ended up doing most of them. But there was multiple times where I said, hey, that’s I got an important sales call I got to do because you take this one and he was happy to sort of trading that off. I do think there’s a valuable experience in both of you being there at all times, but you can take really diligent notes throughout and that’s what we did, Google Doc notes everywhere and they’re highlighting and referring back to these notes and that’s why I think I’m able to tackle this with some sort of a.

Your memory and visibility even though it was now past three weeks in a sort of flew by and a lot of information, other thing is you’re pitching yourself over and over again and so some of the conversations sort of blur, at least the first couple minutes of conversation blur, but. Overall we iteratively adjusted in that journey and started off with you know very I guess feedback of hey, we don’t really understand who your customer is or what a customer journey is. And so after the first or even second day basically did a quick sort of case study slide show and then I used that to then present you know how we work and what a customer journey is for the rest of those calls. That really grounded the conversations and had a much better outcome than the first conversations that we had. So iteratively adjusting the messaging that you have or how you at least.

Speculate that messaging and then also if they’re supporting sort of documentation or slides or or product demos or whatever that it can that can enhance that is super meaningful. And I think that’s just a meaningful thing in anything. So a lot of these things that you know were will take place over time by doing meetings really get sort of expedited and accelerated because you’re doing it such a focused quick interval. And so that was one of the things that I think was meaningful that came out of it. No, overall you have to measure your time like this is about 36 hours to 40 hours probably in the end around 50 hours of your life is going into these mentors madness sessions great that Techstars is giving you some investment but they’re also taking equity and there’s also a terms within their convertible note structure. If you take that that if you don’t you know raise more money then it’s going to convert to debt. And so it’s not like they’re really paying you to do this. Yes you’ve got some money in the bank hopefully you’ve extended your runway meaningful meaningfully.

But overall this is eating up time in your life that you would be sending up spending on growing the business by talking to customers or doing product development etcetera. So there’s a trade off and there’s a prioritization and I I think that’s a difficult one to make at this stage in any company. And so I’m kudos to people who have gone through mentor Madness, kept themselves. Together through it and then continue to excel on the business side and hopefully in their personal lives while doing this. I know there I had a joke to the one mentor that I’m going through like the five stages of grief doing this every day, where some days you’ll wake up and I’m super excited. The other days I’m like, I never want to see another mentor again. And you sort of toggle between that in the end as a whole, you know, super valuable process time that I’m never going to get back, but definitely interesting, exciting and fun and something that.

I I will remember and that not that many people get to go through on a speed round basis with people that are that you know that high of quality so. Umm. Other pieces that I wanted to sort of highlight were just actual real takeaways because I’m already coming up on 13 minutes in the video and I think this is meaningful. I do have a couple sort of links and everything here, you know, first of all my own link and then if you’re interested in this, a couple sort of highlights of tech stars that had done this in the past. And so you can see sort of this one here.

Mute it. But they were meeting in Pods, looks like you would like you know, shuffle through very quickly and that’s how you would have the meetings in the past and obviously a little bit different time, but this would be super engaging, super fun. I like the idea that they’re like writing things on paper and stuff. I think there is a lot of value in that experience of doing it in person, which we didn’t necessarily get. But overall still you know, valuable, valuable time and you know quite, quite, quite a journey so.

Couple of takeaways and these are a little bit relevant to obviously myself as a person, but I think these are relevant to anyone building businesses or a founder was going through Techstars or meeting mentors. Hopefully these make sense and are are meaningful for you. So the first one was and this is very relevant to speak I is this idea of product versus sales lead growth and we have a company that’s OK. I can just share this too as I walk through it. This is sort of the value proposition of the company 7000 people have signed up.

And really sort of this idea of like product LED growth and that you can come sign up. We originally had a freemium model. We converted that to a free trial and the goal is that you sign up, you have a great product experience and then that you know that product experience is so good that you convert into becoming a paid customer and that all sounds reasonable. That sounds actually ideal, but it hasn’t been as easy as that. And one of the things came out is that when you go from a product you know you switch from the city of a product LED growth to more of a sales like.

Within some of them enabled them, you know, together. The deal sizes get bigger. I think especially one of the things that I found is that because of sort of the complex capture analysis and sort of data work that we’re doing with speak, it can take a lot for us to successfully unlock value proposition, value or full understanding of the product directly when you sign up into the application. And so the need for a little bit of obviously there’s two ways that we can go. We can go through better onboarding experience, better user experience, better product, better documentation, better guides.

But in the end, the other one is, hey, jump on a call with me before you start using the platform or or you know start using the platform and let’s jump on a call right when you’re starting to use it. So we can make and then you can qualify those people as customers. And then instead of showing them every little piece of the application and letting them find that out and maybe it works well, maybe it doesn’t by turning on exactly how they think about it, you can guide them through that journey to make it successful. And so that’s something that’s really stuck out to me is like product versus sales like growth and how do we set speak up. To do that’s the best and there’s pros and cons to each way that you go. I’m going to detail this in some other videos that I do because I think this is super important and a big decision to make as a, you know, as an entrepreneur. And I think a lot of us, I dream of product LED growth but it’s not always it’s an anomaly that companies are making that happen compared to the norm. So super, super interesting that came out. So that was take away one product versus sales like growth #2 was this idea of like is basically the question, is this a problem?

Today, is this a today problem? And so when you are constantly shuffling so many priorities as a business owner, as a startup, there’s many things that you should be solving, could be solving, would love to solve. But what you have to ask yourself is, is this a today problem? And one of the things that the guy painted, this picture of awesome sort of mentor sort of talked about the rhythm of being a venture backed company and sort of precede round his head round a, Series A, Series B and the sort of time period between that and then within those periods there are sort of milestones. That you should be achieving and if you know that the milestone of say serious, say me say it’s product market fit with repeatable cost per acquisition and positive unit economics.

That’s a Series A problem, but you’re only in a pre seed round. Maybe then you shouldn’t have, maybe you should be other things that you should be tackling in today’s and obviously there’s always optimizations towards that end state that you want to get to. But as you’re prioritizing and talking about brutal prioritization, it’s very important to figure out what is the problem today that I should be tackling versus what is the problem tomorrow versus next week versus months for versus years. And so that one really stuck out to me and seems like a simple. Sort of question to ask yourself, but I think if you repeat that throughout your life, you can really start to hone in and prioritize on what matters most.

Other feedback that I got is sort of talking about this mentor madness or not feedback, but so take away 3 is this, that people who are in these can become, maybe it’s a mentor, maybe it becomes a friend, but it could also be an investor. It could also be a prospective customer. And so qualifying, categorizing, understanding, empathizing, learning from, and then guiding. That relationship towards where is the ideal outcome for everyone involved is super important and it is a big part of anything in life. But that was just something that stuck out to me where we had a great sort of walk through a customer case study in this inventor who often invested. I don’t even look at this as a mentor mentee relationship in this current state. I’m looking as being a perspective customer. I’d love to use this technology. And so that was a really powerful moment where we sort of realized that we were speaking to what could be, you know, an ideal customer.

Profile and then with that in mind we can start to pick apart the attributes of that person and replicate it moving forward. So that was another one. #4 a lot of different perspectives on fundraising, so this one really spoke out to me because stuck out to me because. Techstars, very sort of venture heavy sort of focus, hey, get your little check in here through Techstars and then scale up and raise around while you’re in the program or immediately after. And so generally you are setting yourself on the path of a venture backed company. And generally if you were taking investment in tech stars that’s what you’re doing. And I’ve had a lot of skepticism in my career about that, this journey of bootstrapping versus venture capital. And so I’d like to ask people, especially considering the market conditions.

Today, what would you? What would you think is the best route? And the other thing I would ask is a, based on the trajectories that you’ve seen from your friends in life, you know, where it’s panned out from, a, you know, say maybe a bootstrapping business or a lifestyle business versus venture capital business, which in many cases can end up in failure. Where do you see people on the success and then the happiness scale of life? And so those two questions were, you know, really?

Informative and the answers were super wide-ranging and some people said hey you got to fundraise and this this is the time to do it right now. And then other people said no. If you know if you just want to be a 15 person company and have a good business then that’s perfectly fine too. And so that was a big, I don’t think I answered ended up on any. Sort of solution or final resolution on where. My mind lies, but I thought that was a super fascinating couple of questions to ask and answers to get. So people think differently about fundraising and the lifestyle that they want to live in, the business they want to be part of. There was two sort of there’s one perspective I heard from a company that raised a ton of money and a really interesting perspective. They’ve been, you know, successful in previous roles and they said we wanted to raise a lot of money because we wanted to burn through our thesis, we wanted to burn through and validate and the biggest resource that we have in this world.

Time. And I would rather burn through all this money and watch this thing blow up so that we don’t waste time. And I thought there was a super interesting he actually articulated it better than me. But that was sort of the general theory and theme around. And I I I have to say I agree. I’ve enjoyed this journey of bootstrapping and making these decisions. But it limits you when the talent that you can hire it limits you in the products you can execute on the segments that you can tackle, the growth strategies that you can have. And so although I’ve been skeptical.

Some of the path of venture capital, I can definitely see the limitations that are ideal to not have to face so that you can be successful and validate those things and then you know make the most of your time that you have in this world. So definitely something that stuck to me and I think just to add on to that sort of this was the 7th sort of a separate but also a connected take away is that. It’s like clarity on what you want to achieve personally and professionally is required. So there’s been sort of. Conflict between even vatsal and I as CTO and CEO, not between us, but I think between our visions of what we want of like wanted to be both a billion dollar company and only having to manage 20 people, that’s quite a conflict because that generally is not how it’s going to work. You’re not going to hit that billion with 20 people is anomaly stories like Instagram and stuff where that’s happened. But that’s again that’s not a normal route that is possible here. And so the question is if you want to tackle that goal, you might have to end up being hundreds.

Thousands of people of a company that you run and that’s a lot different life than 1520 people in a good business. And so I think some of the questions while though a lot of them are tactical and around business and fundraising. Were questions around clarity personally and professionally. And I think that’s a really important thing. I’m glad people were talking about this and asking these questions. So I’ve got two more and then we’ll wrap this baby up. I think both of these are important, which is one is like one of the most common feedbacks that we get. It’s been for years. I’m guessing a lot of startups get and it just makes so much sense. But it’s such a hard thing to do is just narrow your focus. And one of the guys says, hey, give me what you do. I said, hey, we help research firms and they said no, research firms is a whole group of people.

What the individual role and the individual job title? Who do you help? What kind of data is it that you actually scrape and analyze and what are the actual results that they’re looking to get from that? And I was like I don’t have that answer for you. And it’s because we haven’t made the deliberate intention to focus down. We’ve left the system, our system that we’re building at sea. I sort of horizontal agnostic, you know, plug and play playground almost like an Evernote notion where anyone can wander in and hopefully create some value in it. But you realize during that process, especially when you’re doing inside extraction.

That it’s hard to do that successfully and generally where value is created especially with sort of machine learning is that there’s a recommendation or prediction made at the end of it. And until we can narrow in on those datasets and then the actual outcome that we’re looking to instead of just throwing random insights, we’re going to struggle to really find this product market fit and then hit on the gas and accelerate. So that’s definitely something that was very clear and I think a worthwhile recommendation, a worthwhile recommendation. Or anything in life because, you know, I have this basically this chart where I have my public goals print out and it’s, you know, it’s here’s what I want to achieve and it’s by this timeline and some of those goals are conflicting. And then I have a prioritization layer. And I’m saying this what goal is actually more important to me this and really quickly it helps me then, you know, make those changes. But it’s a super difficult thing to do and it’s really hard to do that. And in that regards, you know, I think some of us just wanted.

All right. Now where you see people who say, OK, well I know what I want to do this in the X I’m going to focus on this for the next five years so that in this in the eighth year of of this journey I can execute and actually achieve this. And so there might need to be some short term focus or sacrifices that are made to achieve what you truly want to achieve. And in order to do that you do have to focus. And then the last one is what you were doing, is it compounding? And this actually came to me from a mix of mentor madness and in the most recent all in podcast.

David Friedberg talked about this really eloquently about having equity in a company, and I’m lucky to have equity in a company in a building here at speak. I that now has some credibility and investment from Techstars and has built up over the years, but. I’m asking you know, is this compounding enough? And you know thinking about the journey of PKI and sort of self funding this and then having COVID and then. Likely recession coming here and then public markets that were impacted that then impacted some of the customers that we didn’t. We just up and down and up and down. And you have this sort of delayed gratification that you’re hoping to achieve where maybe at some point you other other printing so much profit in the business that you can you know pay back all the money that you would have missed if you had gone and worked as an employee at a good company or you sell the business at a multiple that makes it worthwhile.

And that’s a thing you really have to play out and ask yourself because definitely have made short, you know, short term sacrifices haven’t always gotten garnered the salary that I want or, you know, accomplished. And it’s it’s really also painted my picture as like a. You know, one of the things that I also thought was like one of the feedback that we got were cyclists that was almost too soft, too nice to deal with. And I also have this mindset that, you know, basically there’s one contract that we only made 10,000 bucks from. They said this should have been $100,000. And so there’s a mind mindset gap there too. And So what I’m asking myself is, am I on the right journey where the effort that I’m putting in is compounding over time and that return in the end, and however you define that.

Return is worthwhile and I think that’s something that all of us need to be asking ourselves as we do what we do, because you can. End up at cap. You can end up cap depending on how you layout and play out your life. And most people don’t want to be that. Most people want to be able to if they’re doing amazing or they’ve done the hard work to maybe some years they underarm, but then other years they overturn whatever that is. I think that’s unambitious vision and a goal that a lot of us want to be realized and we want to make sure if we’re making an investment into something that’s compounding in the right way. So those are some of my takeaways. I’m sure there’s many more that I could go in.

I’ll end it here from Techstars Accelerator Mentor madness. This is my reflection on it. I hope you enjoyed it. Hope it was insightful. You know, if you’re a Techstars person, send me a message if you’re just interested in it. Would love to chat more about this. I think the Super valuable, super interesting, overwhelming, surprising, scary, exhausting fun. But I’m I did it. We’re through speaking. I did it. We made it through the Techstars one. Thanks to Vatsal for sticking through. Thanks to all the mentors. Thanks for tech stars and specifically Techstars Toronto for setting this all up and making this a wild ride.

Have three weeks and meeting a lot of great people along the way. So if you like this comment, subscribe to all those good things. Thank you very much for checking this out. Hope you have a wonderful rest of day. Bye bye.



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