All The Way Up

Most people have a weakness with Massimo Chieruzzi

January 27, 2021 Gary Henderson ft. Massimo Chieruzzi Episode 1
All The Way Up
Most people have a weakness with Massimo Chieruzzi
Show Notes Transcript

Most people have a weakness. But most people will never approach or overcome their weaknesses.

Today, I’m talking to Massimo Chieruzzi. 

Massimo founded this company called Ad Espresso. Many of you have probably used them to manage your Facebook ads or you’ve read one of their blog posts about Facebook.

Massimo is going to share his story of how he was running a web development firm. Wasn’t doing so great, found a big need, and ended up launching a company that went from a super small startup in Italy to one of the biggest partners of Facebook that eventually got acquired by HootSweet.

This episode is going to dive into his journey of working at a startup in a big company, to ultimately what Massimo does brilliantly which is how to find and approach weaknesses.
And let’s just be real. We all have weaknesses.

When we are able to identify what our weaknesses are, how to approach those weaknesses, and how to overcome them, that’s where the magic really happens.

And this episode will give you a specific strategy that will teach you just that.

Visit for direct access to Gary Henderson!

All the way up podcast family today, I'm talking to Massimo. So Massimo founded this company called ad espresso. Many of you have probably used them to manage your Facebook ads or you've read one of their blog posts about Facebook. So Massimo is going to share his story of how he was running a web development firm. Wasn't doing so great, found a big need and ended up launching a company that went from a super small startup in Italy to one of the biggest partners of Facebook and eventually got acquired by HootSweet. Well, I was going to dive into the difference in working at a startup in a big company and how to really make a difference through that whole process. And ultimately what Massimo does brilliantly is he shares how to find and approach weaknesses because let's just be real. We all have weaknesses. And when we are able to identify what our weaknesses are and use a specific strategy that we're going to share with you today, and how to approach those weaknesses and how to overcome them, that's where the magic really happens. It's a podcast family you're in for a treat, Listening to the all the way up podcast is where I bring some of the most amazing people in the world into a private conversation to help you with your business. We share lessons, stories, and insights from entrepreneurs who've been right where you are and have gone on to do Epic things on their very own, all the way up journey. So Massimo, thanks for taking some time today. Thanks for Inviting me. Yeah, most definitely. I've spent a lot of time, you know, just following your journey from afar. This is the first time we've ever actually had a conversation. So, you know, I'm super excited to do that. And Masimo, if you could get us caught up really quick on your journey, it would be amazing. Sure. And super quick intro on myself. I've always been like started playing with computer when I was eight year old in the data center of my grandparent industry, which has, you know, a huge computer, but probably a 1012 power of a calculator today. And moving forward 14 year old, it was the youngest in for cybercrime the BBS with pirated software. I was using stolen ATNT card to make Intel as it was before internet and everything arrived on the other side of the world, which was like thousands of dollar after bet in around 2000, I started the agency just because I wanted to be in my staff. Originally. I wanted to actually build the tech blogger, very similar to select doctor, which was back then probably comparable to today's tech crunch. And I wanted to do something, but they need that. But then it was two bubble. We did that and it was quite successful, but we realized that no one was paying for advertising. It was not sustainable. So we said, okay, let's just be a website for other people. And he had completely no idea of what I was doing. I was 20. I had never worked for someone else, except as a joke. I don't know how we survived. I was literally paying a credit card because no money in the bank account, but we survived. We survived got relatively big by Italian standard. Like 10, 15 people became the biggest developer for eBay across Europe. Yeah. I got a bunch of big customers, but it was boring because we were very focused on technology. I'm building stuff and it did suck what you do, them control what you were building, but it was someone else telling you how to do it. And sometime it was more focused on like branding rather than conversion rates, real results, and very often, but with normal life of an agency, when project gets bigger, if it's for a startup, then usually what happens is that they take it away and they build an internal team. So we started doing a blog network, which was kind of successful, but still not generating meaningful revenue. But the interesting thing there is that it was the early time of Facebook. It was Facebook advertising. It was around 2011 and then Facebook ads just started here and we started split testing randomly. We had a blog about books. And what we discovered is that man just sucks at reading and randomly with an experiment, we solve it. We could acquire a lie from a women for one sense. And from a man, it was like 30 cents, which was crazy different. So there, we had the idea, okay, let's do these at scale. We should split test more stuff, but it was extremely time consuming. So we'll look for a product product didn't existed, or at least it was very enterprise, but they were also too complex. We couldn't use them. They were designed for the full team of marketers, which we didn't. So we said, okay, let's just build it. And as we build it, we got more excited and we saw the blog mentor can basically use the outcome from selling the blogs to find that the press and the rest is pretty well known. 2014, literally in a week when we knew that we got accepted, we moved from Milan to San Francisco, relocated where the startups, which is an amazing startup accelerator. And from Bayer, we raised the first money. We became profitable pretty quickly, which was really key to our success And quite rare. Yeah. It's quite rare overall in the startup mentality. That's why I always recommend reading. If you are in to start up and you want to understand how it is to read the loss than pounder, Byron Fishkin, which is in my opinion, the best representation of how is to really run a startup raise money. And It's an amazing book. I agree, but Literally thanks to being profitable, which is pretty unconventional for startups. Every decision we took was what we wanted to do. We raise money because there was an opportunity not because we needed to raise money. We sold the company because we saw an opportunity to do something bigger together with food suite, rather because we were running out of cash and we had, yeah, of course, but also as consequences on the valuation at which you can raise money evaluation at which you sell the company and everything gets basically, it really empowers you to control the conversation. Yeah. Most definitely. How was that transition though? Like you transitioned from being an entrepreneur, running your company to being an entrepreneur. I know you had some freedoms or maybe a lot of freedoms. Like what was it like when you made that transition to Hootsuite? So you change from any point of view, from a personal point of view, like work life balance. It's probably a good thing because you are less stressed out. You don't have to make like my most important call every day. You are not in bed constant. If something happens, we could like just bankrupt tomorrow mode of a startup. It's really a great for regularizing a bit, your life. On the other side, it was a first time experience for me because I had never worked for anyone else. I've always been an entrepreneur, great learning experience. I learned so much within Hootsuite, bigger company, more complex organization, completely different challenges. So it's really been great. And I'm really thankful to be part of his journey on the other side, like zero to 10 million, maybe 20 million, a a phase because I like, I like the uncertainty and having to deal with everything with every problem, being involved everywhere and really making a difference, which is not how big companies are organized. You know, big companies, boxes. You are either in marketing or you are in product. You need to be specialized. And I don't blame them for this kind of organization. What makes sense when you are dealing with 1000 people and instead of 50 people in larger companies is more about finding very specialized people and replaceable, no one should be unreplaceable because that's create an issue also because bigger company have a higher turnover of people leaving. So it's a very different mindset, but in a startup you are hiring, but rock star in every single department because you desperately need people. But guy that can make a huge difference in bedroom. A lot of what I've read a lot of what I've listened to from you over the years or the time you seem to have this quite unique concept of identifying your weaknesses and ways to process through those. Can you share a little bit about that? I love personal growth. I think it's important. I'm reading a lot of books. I'm Callidus disorganized. So I like reading stuff like atomic habits, always book on improvements and think if you are serious and are working on yourself, there are some things that can improve that maybe by 10 20 per center. But on the other side, you have your own character. You are made in some way. And there are things where you read the feelings where you don't, you can improve, but I'll never be the killer sales guy, but make friendship with everyone and convince anyone to buy a product. For example, and I hate like cold calling or asking people, Hey, would you buy my product to a complete stranger? That completely me. So on one side I read that, try to improve them. The other side, I recognize I'm not good at this. And I can bang my head against the wall for the next five years and try to get better. But on the other side, it's something that will penalize my company, but will slow down. So when you have a choice to overcome that, either you find a co-founder or someone, but it's complimentary to you and can cover for your weaknesses. And that's exactly what I did with Armando. We have completely different characters is super organized, like to run Excel spreadsheets, super organized calendar. And we work together in an amazing way because I'm the cow guy. And he is the one that keeps everything under control, great at networking, et cetera. So that's one option. The other option. And I will say that we did both of them is to find a way where your company, your business can grow, leveraging your strength and trying to avoid your weaknesses. Couple of example, with the agency, I was not good at going out and searching for customers. I had no idea how to build a sales team. So what we did over time was like specialized specialize in not the website, but anyone could build, but building the websites, making millions of visits per month with complex technology and vendor restraints, this pays to like five, 10 companies in Italy that can do better and better way finding our niche, where we were really the best people came looking for us. I didn't have to go out looking for a customer. We just build a name and people would reach out and tell us, Hey, do you want this job? Which was amazing. So your weakness at that moment was developing a sales team and getting out of being an introvert and building those relationships. So what you did is you niche down completely to this super enterprise level clients. So there was only a handful of clients, which made it way easier for you to go build those relationships and find out who your ideal clients were. Yes. And that's really, we became known in the space after a couple of jobs. So actually customers were calling us. I didn't have to call anyone because they knew all, we were one of the five that could do the job. So they knew you were one of the premium companies because you found your niche, you found your space and then you went and absolutely crushed it. You did a great job. You delivered, you did everything you were supposed to and eventually word got around. And you had probably no shortage of customers at that moment. Yeah. Yeah. I think it's interesting. So back in maybe 2006, I took a job and I worked as a vice-president of a company and it was a father son company and they ran football camps, but it was quite unique because the father was one of four vice presidents of Barnes and noble and a branch of the company that he ran was the private college bookstore division, which was their cash cow. So we know Barnes and noble as the bookstore that we go to and the shopping malls or, you know, whatever, but where they actually kept and make all their money is they kept the college bookstore division private when they took the retail bookstore public. So he ran the cash cow, the company. And I learned one of my most valuable lessons that I've ever learned in my life as an entrepreneur. And I wasn't an entrepreneur then at that moment is how to build relationships because he was building relationships with people that I'd never seen or heard of in my life. I was probably 24 years old and I learned a lot, but that was the one little thing I took from Rick, which was the CEO of the company. I had learned how to build amazing relationships with people. So I'm really curious when you and I, you know, we build our relationship and we're chatting, you know, five, six, seven, 10 years from now. I'm really curious to look back and talk about what you took from this time at who suites and where it shapes your future. Because I can tell you without my time with Rick and offense, defense sports, I wouldn't know how to build the relationships that I do today. And I wouldn't be where I am today. Yeah. That's a great learning. I tell it, I agree on the importance of building relationships. And it's also the only thing that really is left out of this experience. Of course, the personal branding, et cetera, is the amazing connection, but we may prove a journey. Rand, Fishkin, Ryan, these matters meet all people, but I was lucky enough to me then build a relationship with, thanks. What's going to make it a little easier to get a door open. When you're opening email, your opening call says, hi, I'm a co-founder of at espresso. You did a hell of a job growing at espresso into a global brand and global brand recognition. So even if someone doesn't necessarily know your personal name, they probably, if they're in the industry that you're new startups playing in, they've probably heard the name ad espresso, or they've landed on your blog at some point in time. Yeah. And that's one of the important thing with learn in music experience. Nowadays, everyone is obsessed with measurable marketing initiatives. Like what we arrive what's the technique parade was the increase in traffic, which is absolutely necessary and good. But I think nowadays people tend to undervalue a lot, the importance of building a brand on top of it. Yeah. I was going to say like an ad espresso brand, a corporate brand, but also a personal brand. And being able to take your personal name as you enter and exit startups and enter and exit phases in your life and be representative of something as a person like a Richard Branson or, you know, any of those famous entrepreneurs, any of the guys on the shark tank, you know, they don't everything they touch doesn't turn to gold, but they get the doors open because people know their names. Yes. And if you can mix like powerful business brand, plus your personal brand with like a CEO, but is very visible, very recognizable. It's like 10 X, your potential or outreach growth, et cetera. I think it's important to find the right balance between the two, because there are some companies where, you know, where the CEO is way more visible than the company. I think that then creates an issue. I agree with you 100%, I saw something the other day and it made a lot of sense in Atlanta quite well. For me, it was an SEO article and kind of geeky and nerdy, but it said, you know, use your H one of your title tag for the search engines use your H two or your subhead for your personality. And I think that's what more brands need to do is they need to show a personality and they need to develop their brand personality as well as develop the CEO personality. Yeah. Yeah. So how do you think that experience at HootSweet shape your future as an entrepreneur? That's a great question. It gave me a lot of hints on how to manage people. I became a better people manager because you know, you work more closely with HR, with people really knows how to manage people. I got a bit more of introduction on how to run startups. The roads are bumpy. It doesn't always need to be. And a lot of processes how to organize product, how to get customer feedback. A lot of things that when you are a startup, you know that you should do it, but very often you don't have time to do it. You know? So it, it was a great learning experience in trying out a lot of different stuff and understanding, okay, I've never done visa, but it's actually very useful Masimo. Talk to me about what's next. So you've taken this transition. You've made an announcement back in, I think November of 2020 that you were going to leave at espresso and leave the Hootsuite team. So what's next for you? Yeah. So I can't events one of the great things about Hootsuite because actually not to it. We met this great guy, Gary on morale and built an amazing lead scoring engine for Hootsuite. And we started looking into the market and it's crazy. Our lead scoring is important, but at the same time, it's still a huge pain point for most of the companies because the CRM, an implementation of lead scoring, it's usually too basic. There are some good companies out there, but they rely a lot on artificial intelligence. And when the lead goes to a sales people, they're like, I don't trust with black box. I get this number. I get this name. I don't understand why I should call. It is not really useful for me. And if they don't trust the output of the lead scoring engine, then it's not going to be efficient. So we breadcrumbs breadcrumbs. We partner me or Amanda, my co-founder and espresso and Getty, who actually in the meanwhile at bill the same things like predictive scoring in another couple of companies and we partner together and we said, okay, let's productize this. And we are building a product around lead scoring for now. The brother vision is an overall concept of revenue acceleration. So really have been marketing sales and customer success team, get the information they need when they needed to get this unified view on the customer and understand which lead it's interesting to call, which customer might be churning soon because it's not very active and get sense out of it too many silos, but that are out there and very into the part. And also putting, moving traditional marketing to a concept of revenue marketing. We have a money pest on this. If you go on our website, breadcrumbs is a revenue acceleration manifesto. I think as of today, it's crazy like how most of the companies still perceive marketing as a cost center while savings considered a revenue center. Most of the sales guys are incentivized by revenue. We generate why this is still extremely rare in the marketing team. And it's crazy because nowadays we can measure the revenue contribution of the marketing team and that should be taken account. So that's what we want to build the space that we got really passionated in the last year. So it's gotta be a great journey. Yeah, I think that's exciting. It's challenging, but I think there's a ton of opportunity there. So I think what you're doing is amazing. I have full confidence that you're going to implement it with excellence as you've done in the past and full confidence that this will be your next success story. So with imposter syndrome, we did at the espresso, it was great that we need to do it again and to be sure, but it was not just like a lucky combination of events. It's going to be a lot of fun. So I'm really excited about building things from scratch, but kale is constantly thinking, how do I grow a blog? How do I increase the number of seniors, et cetera, is just so much fun. Yeah, most definitely. So Massimo, thanks for taking some time today to chat. I'm excited about your new startup. I'm super intrigued personally at spending more time myself establishing or identifying my internal weaknesses and finding solutions to get over them rather than just letting them remain weaknesses. Thank you for inviting me again. Thank you for listening. Podcasts, family Masimo just blew my mind. He taught us how to find our weaknesses. He taught us to either improve or outsource and really just focus on our strengths. He shared how he became the best in his niche and how building relationships that lasted a lifetime are. What's truly got him where he is today. He also went into something that's super dear to me, which is the difference between your personal brand and your company brand and how both need to truly have a brand. I know that I learned so much having a conversation with Masimo, and I hope that you learn by listening to that conversation. If you learned anything at all today, the best way you can say thank you is hitting the subscribe button right on your podcast app, to make sure that you get to hear every conversation that I have with all of my friends. And we're always here to help and support you along your all the way up journey. If you want to get direct access to me, open up your web browser and type in, enter your email address. And my team will shoot you a free gift right away. Then I want you to reach out and introduce yourself because I would love to get to know each and every one of our listeners, we reply to every single message we get. So do me a favor and go to right now to get your free gift and direct access to me and my team.