Today’s episode has been one I’ve been looking forward to since I started this show…
There are certain people out there that can completely change the trajectory of your life forever.
Today’s guest Wiley Cerilli, the CEO of SinglePlatform was one of those people for me. Wiley took a chance on me when I joined his company and my life has never been the same.
He’s a personal inspiration and one of those rare people whose incredibly humble despite how talented he is.
Today Wiley talks about the early days of SinglePlatform and some of the sales mindsets he’s used throughout the journey from idea to a massive startup exit. We also touch upon some of his philanthropic efforts and a few stories here and there.
This was a real joy to listen to. Check it out below : )
Scott: Wiley what’s up man, how’re you doing?
Wiley Cerilli: I’m awesome buddy; really, really great.
Scott: Dude, I’m so excited to have you here especially on the heels of a conversation about Kenny taking cars for joyrides across the country [Laughter] and for anybody who doesn’t know, Kenny is a colleague, one of my mentors who me and Wiley worked with at SinglePlatform. And today I thought we could really talk a lot about sales and how you’ve taken a sales first approach in the companies that you have built and been a part of. And I think this is really important because I see a lot of people out there trying to build technology and building things that people don’t necessarily want.
And the way that you have gone about building some of your companies in particular, SinglePlatform, has been really insightful for me as I go out and think about how to do this. So, can you talk a little bit about when you decided to go and start SinglePlatform and how you approached getting the company off the ground?
Wiley Cerilli: Yeah, sure. So basically, where a lot of the ideas for SinglePlatform came from was me going out with a — I had an overall concept, a virtual concept that I liked but I didn’t know if it could work. I didn’t know if local business would buy it and so what I did was I put together a deck, a PowerPoint deck and made it — it actually had a [Inaudible 0:01:26] [technical difficulty] which I sort of envisioned the product looking like. And I went out and cold-called; not people I knew. I specifically wanted to talk to restaurants and bars who I didn’t know because I really wanted to get an idea of what our sales metrics would look like —
So I took a deck of what the idea may look like, went out made cold-calls and went and met with local businesses and I say out of the first 30 meetings, 27 of them said ‘no’ and would be disinterested when I got to slide number two. And so after every meeting, if I could even get through those slides, I would go back and adjust the decks. The reason why I wanted to do it in person was I wanted to see — you can tell when someone is interested just because they — all of a sudden they are making eye contact or they sit up or their tone changes or and so I wanted to get a first-hand feedback.
So whenever I saw someone react to a certain buzzword that I used or a slide that I put up, I then rearranged the deck and then would go out and try to sell the product again the next day with an updated deck.
Scott: And real quick, I’m curious, I mean how did you get 30 people to commit to a meeting with you via cold-calling?
Wiley Cerilli: So, I used a lot of different scripts for the most part. When you are first starting off and trying to actually get meetings, I didn’t try a lot of things in the beginning; I would like to try something in three to four days to get enough data. So I called and for three or four days I would use A script and then for the next three or four days, I would use B script because the challenge is, if you are calling in every single time and you go maybe I’ll try this and I’ll try that, you don’t know if you just got lucky with someone who was open to meeting or maybe you were more confident about this and that’s why it worked.
So, whenever I try to make a change to a script, I tried to do it over a 3-4day period [technical difficulty] getting meetings. So I called and I’d say, ‘hi, I work for a company called SinglePlatform and I would like to talk with you about a way to manage your website and mobile site and Facebook all in one’ and that did not work out because nobody really cared about SinglePlatform [Laughter] and [technical difficulty]. And so I tried to play with the social aspect of it, I tried to play with the website aspect of it and then eventually got to the point where I would test using different publisher names just to see if I could get a meeting that way.
So I would call and say, hi, I managed a program for A and B website and I’d like to talk to you about adding your menu to their website. And then when I got to the meeting, I talked about how the product could do that but the other benefits were that we could also — when you update your content on SinglePlatform, it also updates your website and mobile sites and Facebook and Twitter. So that was a problem we — I don’t know what iteration of the pitch that was or the call that was, but it certainly wasn’t the first one.
So basically I went out and I would try to sell the idea and I would get all the way to the point and — some people would go, whoa, why would you — it sounds a little weird that you would actually go out and sell a product that doesn’t exist and accept money for it but I didn’t accept money mainly because people wouldn’t give money but the other [technical difficulty] was, I wanted to get to the point where they would actually take out their checkbook or credit cards and be willing to pay for this. And at that point I let them know that this product was launching in three or four months and I would circle back when it was ready.
And the reason why was I didn’t want to quit my job and ask other people to quit their jobs and raise a round of funding if I didn’t know that people would actually buy a product. And I hear a lot of entrepreneurs that have an idea for a concept say, well, and they were already in the process of building this thing or it’s already launched and they say well, I’ve met with 20 businesses and they said that they would do it once it’s live. And the reason that I don’t like that is because I feel like they might just be — saying no to someone when they are sitting right in front of you, is an uncomfortable thing and so there’s an excuse for the local business owner or whoever it is that you are trying to sell to that they have that the product is not live to say, oh, I like that.
So for instance, even when I am throwing an idea out to a friend of mine, an idea that I am having for a company to a friend of mine, I won’t say, I have this idea; what I’ll say is, oh, my friend has this idea for an app that does whatever it is and that [technical difficulty] feedback because my friends don’t want to say that’s a shitty idea, Wiley. So —
Scott: It’s like nobody is ever going to tell you that they hate your shirt because they are your friends.
Wiley Cerilli Interview: Yeah, [technical difficulty] shirt [Laughter] fuel the dreams — if you build it they will come kind of thing, just don’t — I don’t like the idea of pouring all this time and money into something if I don’t believe that they are going to sell it; if you buy it, then I’ll build it kind of thing. And so that’s how I really started SinglePlatform and after three months of doing that, I got to a point where a business a day would be willing to take out their checkbook and their credit card and say, I want to pay for this. And that’s actually when I went back to all these businesses that said yes, took that money and used that as a down-payment for a production company to build the initial product which was $25,000.
Scott: Wow, talk about de-risking your startups. So these businesses, when they committed and they said, ‘yes, like this is something that I want’, would you just say, ‘okay, I’ll be back in three months’ or would you take a check from them and say ‘I’ll pay you back’ or what was logistically — what did the pre-sale look like logistically?
Wiley Cerilli Interview: Yeah, so what I did with people was I would to get a check from them, most of them were writing checks and I would say, okay, I’m going to take this check and we — they knew that the product wasn’t live yet and I said it’s going to launch in whatever it was, like in 2-3 months and I would say I’ll cash it upon once it goes live and I’ll email you out your login and password. And so what that — I actually paid the firm up with my money out of my account but I knew that the safety net was there of these businesses but I also knew that if this thing didn’t launch for six months, I didn’t want to take their money and then all of a sudden we get in this huge argument over ‘well, you said this was going to be three months’ and so I just told them that if it’s not live in three months then I would give them their money back.
So, that went really well and I also built in with a company that — and I outsourced the technology. It was actually, they agreed to do it for $50,000; $25,000 upfront and then the other $25,000 once it went live but that was contingent upon it going live in three months. So they did not meet that deadline, it was actually just over the deadline and I reached out to the businesses and said, okay fine, we’re a little bit behind schedule as every company is and they were all fine with launching it still.
Scott: That’s a really cool story and one of the things that you mentioned that I think is really interesting is some of the things that you look for when you’re doing a sales pitch. And you mentioned the eye contact, you mentioned people sitting up in their chair; I would love to just get inside your head for a second when you go down to pitch somebody because you’re one of the best sales people that I have ever been around in my life. And I mean, let’s first talk about before you go into a meeting; what are the types of things that you are thinking about and the mindsets that you take when you are about to go and pitch a product that maybe you have never pitched before?
Wiley Cerilli: So there’s this test — we took this test when you worked at SinglePlatform it was the controller, stabilizer, analyzer, persuader, remember that?
Wiley Cerilli: And so usually people have one dominant one and so your persuader is usually more like sales people, they like to celebrate; the stabilizers look for harmony, the analyzers are looking for data and the controllers want to get from A to Z as quickly as possible and they just want to build a solution and get there. And they are good at doing that. So all of them have their strengths and weaknesses and everything and one thing I think regardless of whatever I am trying to sell is — and I keep in mind is trying to find out ways to identify which one is their most dominant personality trait.
Let’s say you go in and you’re meeting with an analyzer; well an analyzer doesn’t want to be sold, you don’t want to use a lot of adjectives, you don’t want to promise them the world. What they want is data, they want to see like who has used it, the exact results, that kind of thing, like ROI. They want to talk numbers and data and so these — the stabilizers were harmony and so you want to go in there and you want to establish more of a relationship with them. You’re asking more personal questions just to get that meeting going, you want that connection whereas the controllers don’t want to establish the connection, they just want to know like why are we here, let’s get through it, let’s work this thing through quickly and so I can make my decision and they are quick to make decisions. So that’s one of the things that I keep in mind is just ways to identify the type of personality that you are dealing with.
Scott: I have never asked you this, but have you ever studied NLP?
Wiley Cerilli: No.
Scott: So it’s actually a concept, the concept that you are talking about now and for those people that don’t know it, NLP is as it stands for Neuro Linguistic Programming and it’s essentially like —
Wiley Cerilli: [technical difficulty]
Scott: [Laughter] It took me a while to figure it out as well but essentially what it is, the ways that we can persuade people using our words, it’s almost like verbal copy-writing so that they take the actions that we want. And one of the key concepts is calibrating with the personality type of the people that you are presenting to because people are going to respond to you differently. So it’s really cool to hear that you are basically using this sophisticated NLP, what Tony Robbins calls a technology, without even really knowing it. And I’m curious, are there any types of — how would you figure out early on in your action what type of person somebody was?
Wiley Cerilli: Yeah, so by the way I think it applies to not only to just types of questions that you are asking but the way that you sit, the way that — the tempo of your pitch and the different parts of the tempo like when to speed up and when to slow down, it all sort of plays into it. When you take breaks and what you are saying has so much emphasis in it. Anyways, so how you identify with it? So there’s some natural — just questions upfront; so if you are meeting with someone on a Monday or a Tuesday, you ask them about the weekend, the controller is not going to talk about it, the persuader will go right into it; you can see how — if someone is going to engage you more on the personal side —
Kenny is a master at that. He goes in and he can identify very quickly, if someone wants to talk more about their personal life and he asks those questions. So I think asking some personal questions up front, you can tell whether someone wants to talk about those things and [technical difficulty] a persuader will talk about how he went out last night and how — you are sort of echoing and mimicking their personality. And you can ask them a lot of questions, [Inaudible 0:13:24] at SinglePlatform has done an awesome job with the enterprise sales which is like a longer sales cycle and its asking a lot of questions about what they are looking for, what their goals are.
And so analyzers will use more numbers and controllers won’t talk about the short — they won’t talk about what they are going to hit — like this week they were going to talk about their overarching vision and stabilizers might talk about the people on their team. And so we asked them about the problems that they are having and the challenges they are having and it just — I think once you are aware of it — I try to remind myself before I go to a meeting every time, because it’s so easy to forget but if you get in a habit of reminding yourself before you go into a meeting, there’s just red, green and yellow flags all over the place when you start to meet with someone. You’ll start to see a lot more.
Scott: Yeah, I thought I’d share real quick another tip that I learnt recently, that makes so much sense but I never did this. So when you are in a meeting and somebody says like, ‘okay, so tell me about your company’ or whatever it is, a great question that you can ask is, ‘well, what would you like to know?’ And then that basically prompts that person to —
Wiley Cerilli: Yeah, that’s right.
Scott: — to give you exactly like what they are interested in, whether it’s metrics or one of their figure out — where your favorite places are to go out in New York City or whatever it is and you can kind of pull out exactly what you want from this person and calibrate the way that you pitch them.
Wiley Cerilli: It’s a great idea, yeah.
Scott: So dude, I’m also interested personally to know about this. A lot of people — they had $25,000 in revenue more or less, a lot of people would have said great, awesome, I have a software as a service product, I have money in the bank, I’m just going to go ahead and bootstrap this until it gives me the lifestyle that I want or whatever. But you decided to go out and raise institutional capital. Can you tell me a little bit about your thought process behind that decision?
Wiley Cerilli: I love building things and things can be — I think that’s a cheesy thing to say but I love — whether it is technology or teams or nonprofit organizations, I love building and I like trying to solve — now that I have been out of school for like 15 years now, I like to try to solve problems that are — I just try to solve bigger and bigger problems each time I go out to try to solve the problem. And so what I was trying to learn throughout that process was it’s just a problem that not just restaurants have, but bars have and spas have and salons have and florists have is that the last business we had [Inaudible 0:16:25] certainly solved a lot of problems for consumers ordering food and then also for restaurants as well.
But I wanted a product that was going to go beyond that I felt like I could bootstrap it but if the angle was to help empower hundreds or thousands or millions of businesses, I’m not going to get there. I may eventually get there by myself, but very likely not and when you do an institutional round of funding, there are obviously pluses and minuses to it. But one of the big pluses to start with is you are going to — it’s going to need you to bring on all these other people than can actually do the things that you want to do. For a — I think I’m a unique CEO in a sense that I’m not very smart and I can’t do a lot of things that most people can do. Scott, you’re super-smart, I think you could walk in to most companies and take over most jobs and do a great job.
You are first for learning and wanting to grow and the way that you can take in all this information and process it and have an intelligent conversation about it; like the idea of having a podcast with all these people from different industries to me is frightening. I’m not that smart so there’s an advantage to being smart and a disadvantage. For me — a disadvantage that I can’t do all these things, I am learning disabled, I can’t — I’m not good with numbers, I’m not good with reading, really not good with reading beyond few sentences like just reading [Inaudible 0:17:56] is difficult.
So you may nearly see that as a disadvantage but the advantage to that is I had to do it at a very young age; learn how to identify talent like meet with you and I’ll never forget our meeting and thinking, ‘whoa, this guy can do a lot of great things’. And when I say lot — I can say that sentence about a lot of folks at SinglePlatform; whether it’s Adam or Kenny I mean the whole team is just incredible. So I think the advantage of not being very smart is that you get to be able to identify talent and then empower them. And so I learnt that at a very young age, dropping out of college when I was 19 that I couldn’t do these things and therefore I needed to be able to identify the talent and then empower people.
What’s that quote, ‘if you want to sell the sea, you don’t gather a bunch of men and tell them to build you a boat. You teach them to yearn to sail the sea and they will build you that boat’. So I think I know how powerful it can be when you find great people and allow them to build ships and sail across seas. I think with institutional — going back to your question, raising money and even for you to bring on resources like a Kenny and an Adam and a Pete and a Stephanie and a Lee and a you and make that dream come true. So a big part of making my dream come true was raising that round of funding and bringing on those kickass people to make the thing happen.
Scott: Dude, thank you for sharing that and I’m blushing big time here. So good thing, this is audio only [Laughter] but I think — I actually kind of want to dig into this because I think when I think about your strengths and you do have a ton of them, you are definitely really smart and you are selling yourself short but I love the humbleness, is that you can really get the best out of people. Like I remember being at SinglePlatform and every time that we would meet, me just trying — thinking so hard about how I wanted to please you and then I wanted to do an amazing job and I wanted to leave that meeting feeling like you were pumped about my work.
And I know that I’m not the only person that feels that way and I think you have this magical way of getting out the best out of people yet while maintaining your grace and likeability. And I’d be curious to kind of know like, how you think about that.
Wiley Cerilli: I think I am — so Brad Feldt a proven entrepreneur and investor; he said, ‘I think it’s a complete fallacy that a CEO and a leader can motivate people but what they can do is provide an environment where motivated people can excel’. So I think that I don’t motivate you, the motivation comes from within you; you always had that in you and Kenny always had that in him and all those people always had that in them. You need to find people like you and Kenny and everyone has varying degrees of it.
So, I don’t think I motivate you or I don’t think I make you work harder, I think I just helped enable an environment where you can take the reins and then run full-speed and therefore you get this high off of it which is awesome because you are doing what you should be doing and you also have a responsibility in it — which is rare for younger people but that letting go aspect is honestly one of the hardest things to do as a CEO is to let go. And I see a lot of CEOs and they talk a lot about that, they don’t want to give up and for me, I can’t not give up and so I know the results that you can get when you empower people.
Scott: So what do you say is the most important function of a CEO is in your opinion then? [Discussion off the record] So we talked a little bit about, I guess, your ability to get the most out of people and it sounds like a lot of this actually has to do with the function of the CEO and what really makes a good CEO. So I’m curious, what do you think the most important things that a CEO should be focused on are?
Wiley Cerilli: So I think a lot of it goes back to what stage of the business that — I think I’m a good CEO for the first two stages of the business which is like the testing phase and the tuning phase; going to scale but not to scale phase. The test phase is like when you are family, I used to talk about it all the time, like a family two to five people and everyone is wearing different hats and you’re in it — you’re so passionate about the vision and business but you’re testing to see, is there a business there?
And I say we were in that phase for I don’t know, for the first year a half and then you go into the tune phase. And the tune phase is like okay, we know what our model is now we need to tune this thing and get it ready so that we can scale it out. And so I think it takes more of a different skill set when you get to that phase of the business. People start to specialize in these little families, you may have a sales team, you may have an account management team, but small team; let’s call it 10-70 people or so. My favorite time, because you are still scared about this not being a business, you think you found your model and you add some more strategic people in and you came right around the top which is awesome.
And you are so more in the test phase actually and then we sort of into the tune phase and the next phase is like really scaling it out. It’s when you have directors — you are bringing in a very senior HR person and a head of Finance and you go from beyond 70 people to 100 people and 100 people up and everyone doesn’t know each other’s names and people work there not necessarily for the vision but they are there because they want a job at a cool company. It’s kind of more of a job as it’s opposed to this thing that is just burning inside you and the whole organization and everything.
And so I think it — it’s a long story but I think it takes different things at different phases of the business. And so, I think for the first phase of the business, being able to sell people on a vision, just know [technical difficulty] vision is super-important and a I’ll say, one of the reasons why it is so important is because you don’t have anything. You need to be able to help influence people to buy into your idea; that’s investors, that’s the angel investors but that’s most importantly, the team. So, you need to be able to recruit good people to make things happen because those initial people are the most important people because they are going to — they are going to be the ones that make this happen or not. And so I think a lot of that goes back to being able to sell and get people excited about an idea.
Scott: Is there any particular thing that you would focus on when you are trying sell a vision? Like quantifying the size of the opportunity or like how much fun this is going to be working together or why this is such an important problem that we need to solve; I mean I’m constantly thinking about how I can captivate people in a conversation and I am curious to hear what you think.
Wiley Cerilli: I think in general, I like not trying to use the word ‘I’ and instead telling stories of other people’s problems and why. And I did this all the time at board meetings too where when we were trying to sell a business. Instead of saying, this is what I like most about the business, what we like most about the business, it was like this is what Howard at First Round Capital loved about this business, this is what this person was blown away by, this is what this business Ken at Blockheads loved because his problem at Blockheads was A, B and C.
And so the story-telling is just so important because when you can tell a story and people don’t feel like you are selling this much, but they get to enjoy this little ride that you are taking them on as opposed to, ‘let me tell you why I think this is such a huge opportunity’. It’s more of a, here’s what other people think and other people’s problems are. And if you can do that in an open way, you can really get a lot of people to buy in.
Scott: Yeah, that’s a tactic that I would use all the time that I learnt from you guys; basically a non-obnoxious way to show social proof and instead of people like so, who do you — why is this awesome or whatever, I could say, ‘we work with Google’ and I would come off like a fool and people would probably hate me. But if I say — it’s how I phrase it again is something that you just alluded to and I learnt from you guys and — well, one of the things that X-Y-Z big player loved about us is the fact that we can do this thing and it’s like a much more endearing way to phrase something.
Wiley Cerilli: It’s funny because I remember being in our old office and there’s like nobody there, single digit people and I remember having that exact conversation. I remember the desk I was sitting at with Kenny and we were writing the publisher pitch and I remember saying that to him like when — where we would say, ‘oh this is what Google loves about this’, or ‘this is what this love about it’ and it’s just great to hear that [Inaudible 0:32:52] effect; because I really think it’s important.
Scott: Absolutely, and by the way, that is not just in business stuff; that’s life man. That’s what — in communicating with your peers I feel like there’s constantly just situations where we are like — are in a position where we could say something cool about ourselves and we don’t want to but we still need to communicate the thing; so I use this tactic all the time in my life because I just feel weird talking about myself.
Wiley Cerilli: I agree with that.
Scott: That’s cool man, so vision; any other things in terms of like stuff that you would think about or focus on or stuff about early CEO?
Wiley Cerilli: Yes, I would say there’s — I don’t remember if you were [Inaudible 0:33:44] I don’t know if you saw them speak when Angus from Swipely came and spoke?
Scott: Oh yeah, I love that guy.
Wiley Cerilli: He said this friend of his, I don’t remember who it was but back — for those who don’t know who Angus Davis is, so he starts a company called Swipely but before that he’s the cofounder of TellMe which sold to Microsoft for 800 million dollars. The guy is like super-brilliant and he was talking about his past experience and he said he met with someone who said to him like the winner between — in the battle between the alligator and the bear is determined by the terrain. And what he meant by that was, you can’t be an alligator and a bear; you can’t have all — you can’t be Iron-Man and Spider-Man and all these things. You can’t dominate water and land.
And I think there’s a tendency for a CEO to want to make their thing perfect and to make sure that when he or she looks at potential competitors, there’s a feeling like ‘they have that and then we need to have that’. And so what ends up happening is we say, ‘okay, well, we’re going to dominate land but this is what we are going to do for water and this is what we are going to do for air and this is what we are going to do for space’ and so you end up moving forward and having like, almost like five sort of priorities and building a lot of things that if you were to give them a grade, give them like a C as opposed to focusing on just land. Like ‘forget it, I’m a bear, I’m going to fu**ing dominate land and I’m going to be really great at one thing’.
And when you do that — and so with SinglePlatform what we decided early on was that we would only focus on bars first and once we got the initial products launched, we said, we’d only focus on bars first and then after that we go to delivery restaurants in top markets and then delivery restaurants everywhere and then high-end restaurants and then spas and salons and florists and that took us a long time for us to make our way through the category. But you could say well, and that’s where we are looking to say well, you only work with bars but that’s what I’m going to invest but that is the opposite because what we did is we created metrics that were so good because we were so good to just selling to bars that [Inaudible 0:36:04] okay, you did that well then we’re going to assume that you will do the next category well and the next category well.
So I’d say, going back to the question, the ability to focus on one area and build one thing that delivers that knock-out punch and not to be distracted by competition instead of trying to do a lot of things at once. And I think it’s short-term goal for the best way to do that, you say to a whole company, ‘this is the one thing that we are trying to prove or disprove this month’ and then go after it and attack it with every ounce of energy that your organization has.
Scott: Dude, that’s also such a great mindset for just your own mental health like when you approach like your problems, when you are trying to be an entrepreneur and start a business, it’s like there’s never a shortage of crap to do. And when you don’t know what to do or what to focus on, it’s probably the most frustrating, annoying thing in the world.
Wiley Cerilli: It is.
Scott: And just that like laser focus, I love that.
Wiley Cerilli: Yeah, I mean it’s so easy to become distracted by all the different things and try to move — well for instance like if you are going to do — I met with the founder last week and he wants and he wants to build out his sales force, and I was like, ‘what was your sales metrics like?’ He said, ‘well I think I should sign 40 a month’, I forget what that number was and I was like, ‘oh, how many did you sign when you were doing sales?’ And he said, ‘well, you know, I was dedicated like 20% of my time to it so I didn’t multiply that times five, but I multiply that times four’.
And I told him, I was like ‘I really highly suggest that you dedicate a certain period of time and just do a 100% sales just like you would as a sales person. You understand your model so much better and that’s not just for sales, it’s splitting your time doing everything which was CEO and how do you call people out for that’. So I think the more that you can just focus blocks of time out to achieving a certain goal, the better you’re going to be at it. You’re such a great example of this and I think whenever you push the blog around like New Year [Inaudible 0:38:22] about resolutions and everything, every year you can do one or two things, you can write out the 50 things that you are going to change about your life in every category, and I’ve done that so many times it’s embarrassing.
[Laughter] I’m going to do this, I’m never going to eat unhealthy again, and I’m like, write a letter to every person I love every day and [Laughter] it’s such a beautiful vision but [technical difficulty] and then you don’t do that and then you just don’t do any of them. So instead, you focus your energies on like I’m going to focus on this one aspect and this one area of my life where — and this is just a more effective way of going about things and so, anyways —
Scott: Totally; no dude, it’s good. So, I had to figure out a way to get this story into this podcast about you riding a bike around the country because it’s just so good and it’s probably — I don’t know if there’s anything the business people out there are going to learn from this. Hopefully though, but I really wanted to get the story in there because it’s so cool. So can you tell us a little bit about your — you were 19, right?
Wiley Cerilli: Yeah, I was 19 years old and I was living on a wood floor in Manhattan and [Inaudible 0:39:40] floor and just completely broke and I had a certain period of time where I felt like I could — people say, ‘oh my gosh, it’s so risky of you to drop out of college at 19’ and I don’t get it. And the reason I don’t get is like, you’re 19 years old you go back to college the following year, you know what’s risky is when you have a big mortgage and a family and all these people that are depending on you.
So, I felt like at a younger age, I wanted to take some big swings and I read Lance Armstrong’s book, it’s about the bike and I wanted to do a fundraiser for my dad who passed away when I was 16 from lung cancer and also a fund raiser for some educational organization, nonprofit because I had to drop out of school because I didn’t have a lot of money. And so, I decided to like — why not try to do something where I just learn a lot about myself by putting myself in a super-challenging position and hopefully inspire some people along the way.
So I decided I was going to bike across the country and bike for a month straight and people would pledge a certain amount per state that I made it to within a one-month period. So you donate a dollar per state, I made it to 30 states then you donate $30. And so with no training or anything I just I jumped on a bicycle and flew to Arizona and started there and because I knew that there’s the four corners there so I biked out for the four corners and —
Scott: Early momentum.
Wiley Cerilli: Yeah, [Laughter] I’ll never forget that feeling when I got up the airplane, my bike [Inaudible 0:41:21] I was like ‘oh my god, what did I just do?’
Scott: What did your friends and family say when you said you were going to go bike around the country? This is like Forest Gump stuff.
Wiley Cerilli: Rachel [Inaudible 0:41:32] said this quote [Discussion off the record] so she said, ‘set your life on fire and seek those who fan your fire’. So you asked what my friends and family did, they fanned my fire from such an early age whether I was dropping out of college or doing that going out to sing acapella or whatever it is. All these things I could be potentially very embarrassed by and they just supported me and that’s one of the things that I am most — I’m the luckiest person of all because of all those folks and so they supported me along the way.
I didn’t have a cell phone or anything, I’d bike about 100 miles a day, I had a trailer on the back of my bike that I pulled and would pitch a tent at the end of the day all the way up these mountains or out in the Sangre De Cristo valley, like New Mexico and I’d knock on doors and ask to camp in people’s backyards all the way until about Florida. So I biked from Arizona to Florida and out to Maine in 30 days and raised a lot of money actually, $30,000 for American Association for Cancer Research [Inaudible 0:43:09] and I kept a journal along the way that I would write in — that was incredible.
I just did something that I didn’t think I was going to be able to do and learnt a ton about myself and met so many amazing people along the way.
Scott: You still have that journal?
Wiley Cerilli: Yeah, I do, I look back at it and it’s hysterical. Keeping a journal I think — that’s one of those things that’s in my yearly list of like ‘I’m going to do that this year’ because every time I read the journal from way back then, they are so great and I — unfortunately I don’t keep a journal but it’s great to read that journal.
Scott: And somewhere along the way, The People’s Court got involved?
Wiley Cerilli: Yes [Laughter] it’s a crazy story. When I got to New York I went upstairs and did a speech to the 24/7 Media who sponsored my bike trip and came downstairs an hour later and my bike was stolen. So here I am, this 19-year old kid and doing this fund-raiser in honor of my dad and on the sidewalk I was just like crying because my freaking bike just got stolen and it was so defeating. I took a train home and brought a new bike and finished up the trip and then two years later, was walking down the street and a bike master [Inaudible 0:44:20] pull up on my bike. [Laughter]
I knew it was my bike because it was — it’s a special bike; a beautiful, specialized alloy bike which cost a lot of money and that special rims on it because I was pulling a trailer. And it had my water-bottle holder on it and my timer on it, so I could track how many miles I was biking and it had a plaque on it that said ‘Brought at East Providence Cycle, East Providence, Rhode Island’. So, unless this guy went to East Providence, Rhode Island and brought the same bike and had everything customized, it was definitely my bike.
And so I tried to buy it back from him and he said he brought it new and we got into this argument and a policeman came over and took the bike and I had to file a small claim to try to get the bike back from him. And People’s Court called and they said, we’ve read the story because it’s a public file and we’d like to bring you on People’s Court so you can talk about your bike trip and get your bike back. So, went on People’s Court and the way it works is that you go on the show and if I won, the person that I was suing doesn’t have to pay me, People’s Court does.
So that’s why they get all these crazy folks to come on the show. And you go on the set, it’s like 12 feet tall, it’s so ridiculous and the music [technical difficulty] at the end of the show the judge comes back out and she says, ‘you know Wiley, I know why you did this bike trip and I know you did it for your dad but unfortunately the police made a mistake and they auctioned off your bike and we don’t have it anymore’. So I lost my bike again and was near tears again, I don’t cry as much but [Laughter] so that’s two crying stories in one podcast.
Scott: It’s a really sweet bike.
Wiley Cerilli: Obviously the bike meant a lot to me. So, I did another fundraiser where we ran around the perimeter of Manitou, and it was a 50-mile beach run and anybody [Inaudible 0:46:13] promote it and on my television day, rolled my bike out and presented it back to me. And so I still have the bike, it’s locked up in the basement here now and I don’t ride it very often but I smile every time whenever I see it because it’s a great story and just an insane and incredible experience. If you don’t believe, you can just Google and you’ll see [Inaudible 0:46:39] still out there on YouTube.
Scott: That will be in the show notes, we will make that available to people that want to check it out.
Wiley Cerilli: Yeah.
Scott: And this is a good transition because now I know you have been focused a lot on raising money for charities that you care about and this to me is really awesome and interesting as well because I know a lot of entrepreneurs who get started and say, I’m going to build my business and then I’m going to go and do something philanthropic. And to an extent, you have been able to do this and I just love to hear what the experience of that has been like because that’s what so many people say they want to go do.
Wiley Cerilli: Yeah, and I’d love to talk to you about that. I — first I wanted to just go back the last point around like that’s why I did it and I think you are a perfect example of this. Of someone who appreciates their willingness to put themselves in an uncomfortable situation because they know that they are going learn and grow a tremendous amount from that. Matthew Mar [Inaudible 0:47:46] is another perfect example of this, Matthew Mar had been part of the SinglePlatform, we met and he had no product experience he was actually finance and he — he managed the whole product for SinglePlatform and he’s on the executive team now and he’s unbelievable.
I asked his sort of philosophy about his career and he’s like, ‘I want to put myself into a position where I am learning the most at all times’. And he does and it’s just incredible and whether it’s a physical challenge like the one I did, where you are picking up and going to another country and learning another language like you have; the value of putting yourself in an uncomfortable situation and even though you know you are going to lose, I think it’s such a valuable lesson. And I think it’s one of those things that helps — motivates you to take bigger swings in life like you aim for the stars and you are mostly going to miss but you end up on the moon.
And it’s a great thing that I think of you all the time when I think about why I am scared to just take a chance on something. Anyways, I just wanted to say that.
Scott: I love that; that makes me so happy, thank you for sharing that. Honestly, it’s the key to success. The key to success is pushing your edge because truthfully, what holds us back from doing amazing things I think more than anything is ourselves and when we dig deeper into that, it’s the beliefs that we have about what we can do. And truthfully, we can do whatever we want; it’s just whether we are actually going to have the stones to take the action to go do it. But we can at least try and we are always going to be better and happier that we tried. So that’s really cool that you feel that way and I love that at 19 years old, you had the foresight.
Wiley Cerilli: Yeah, and I had some amazing people fanning the fire and to support me at such a young age, saying, ‘go for it’. So you either look at things and you look at them as challenges or you look at challenges or things or problems and you look at them as bad things or you look at them as opportunities. My dad, this is the last story I’ll tell about this, but my dad, he was a real estate developer Providence [Inaudible 0:50:01] and a very successful one and then lost all his money.
But I remember him; he took one of the tallest buildings in Providence and somewhat like an eyesore in Providence when you drove down 95. It’s just a brick building, all brick and he commissioned this artist from [Inaudible 0:50:20] to go and paint these big, but fake bay-windows on this brick building. And so when you drive by 95, you look at it and they are beautiful windows and they are still there now and you look at them and you’d think they are real windows like they are beautiful, bay-windows. And he actually painted a little flower pot where there were always [Inaudible 0:50:38] and it was kind of cool but anyways, the reason I bring that up is because he taught me at a very young age that you —
My dad saw windows in a windowless building. Whereas other people saw a brick wall, they see brick walls and he sees windows and I think if you are taught that at — the younger age that you can learn that, the best because you can appreciate all that life has to offer you and it’s like amazing and so —
Scott: By the way do you know that’s your Skype picture?
Wiley Cerilli: What?
Scott: The picture that you have as your Skype name is the windows on the walls of the buildings. So I’m looking at that right now.
Wiley Cerilli: Yes, it is, it’s so funny I used to have that as my Twitter [technical difficulty] yes, so that’s the building. So when you are driving by 95, you only saw the first top four, you don’t see down the bottom; looks like paints ripping off because he had artists make it so that it looks like someone is peeling the — like a piece of paper off of the building. But yeah, so that is what it looks like and that is right next to the building but from a few blocks away, you can tell, it’s so cool.
Scott: That’s awesome; so talk to me a little bit about the charity stuff.
Wiley Cerilli: So, like I was saying before, when I was 16 years old, my father was diagnosed with lung cancer and he went from a healthy 170 pounds to like a mere 90 when he passed away and it was just an awful experience to go through for anyone. And I didn’t really talk about it very much and I went through a destructive phase and everything and really bottled it up. And I think being at that age, a lot of people — yeah, I had a lot of friends and everything that were supportive but they didn’t know exactly how to be supportive because they don’t know if you want to talk about it because it’s depressing to talk about.
Or maybe it’s not depressing or what questions; and when you lose someone at a young age, you do want to talk about it, you feel very isolated, you feel like part of your childhood has been taken away from you and you all of a sudden are dealing with these realities of — that a lot of people don’t have to deal with till much later on in their life. And you’re teenagers and you’re still trying to figure out like ‘who am I’ and as a person, you’re going through puberty and you have college and girls and all these things that are floating around making it difficult for you to process what’s you are dealing with.
And so six years ago, I met some folks who wanted to start a camp for boys age 9-13 who have lost a parent or a sibling and it was called Manitou Experience. And the reason why it’s called Manitou is because that’s held at this camp called Camp Manitou that shuts down at the end of the summer and they give us the camp for free. And it started with like 20 kids, 9-13 years old and the idea was let’s bring them out to camp, 90% of the times just playing games, bottom to 14 play every game under the sun, it’s a beautiful camp. Let them be kids and then 10% of the times you have these group therapy sessions or exercises and one of the exercise that we have them do is write a letter to your lost person.
And these are kids that have dealt with all different things like they were three years old when their mother and father died, they don’t remember or their parents committed suicide. We have a kid whose father killed his mother and then shot himself — all these crazy stories and — but basically, it’s an environment where they feel safe and they can share their feelings and be around people they can have this insanely unique bond with and can really let the emotions out. Whereas if you don’t, it could be really destructive like I said it was for me. And so it provides an outlet for them to do that and it provides them an outlet to just be a kid and get away from all this reality and just have fun and play games.
And so we started the camp six years ago and it’s now 150 campers in Maine, we have a camp in L.A., it’s free for the kids to go to and I’ve been a camp-counselor every year like in the bunks with kids. We had to get a counselor per bunk and it’s amazing when you go around the first time around the circle and the kids will say their story about what happened to them to a camp-counselor and then I’ll say my story about how I lost my father and then all my grandparents and aunts. And they all of a sudden, look at you differently; they’re like oh, this is just, a connection, this person is a connection they have been through this and they are as many years older than me.
And a lot of camp counselors there are in their 20s and 30s, mostly younger and there’ll be some that are 40-50; mostly younger so we can have a more of a bond between the campers and the camp counselors. And so now they have like a mentor — we have all these mentors; nurses and doctors and lawyers and teachers and people that are happy with their lives that are there to support these kids that have gone through something similar to them. And so we found some real magic at this camp and we are fund-raising and we want to open up three more camps in the next few years. So, yeah, it’s incredible; it’s a little startup and it’s amazing how its [technical difficulty] the week started that I volunteer at the time that I had the most fun out of the year by far, it’s amazing going there.
Scott: Yeah, that’s absolutely amazing and I love how you’ve kind of finished it up by phrasing it like it’s our own little startup because I think a lot of — I don’t know man, like we are talking about your fundraising stuff before hand and I think a lot of people like — ‘I’ll go and I’ll be successful and I’ll do some philanthropy and I’ll be all soft and it’ll be easy’ and it was like no, you were like grinding to raise sponsorship money and it is a startup. And you know, you have the ability to impact all of these people directly and it’s just as competitive if not more, as building a software company or whatever it is that you do.
Wiley Cerilli: Yeah, it’s challenging because you are resource-constrained again and raising money is a little bit different and you are asking somebody to give you money and you’re not going to [Inaudible 0:56:59] like millions. With this obviously there is a great return with this but it’s a different approach. So it’s different from asking people for money and difficult getting that money but the great thing is because we only have one paid person on staff who makes $30,000 — and we raised that and so every penny that we raise is going straight out to [Inaudible 0:57:19] camp and so it’s great to be able to see that in the long run [Inaudible 0:57:28] camps.
And yeah, we’re really lucky to have another incredible group of people like this family there that is so passionate about it that is not [Inaudible 0:57:35] so they can scale this thing out. And there’s 22,000 kids in New York City who lost a parent last year. And one of our challenges is just getting more kids to camp; how can we find more kids, there’s obviously more kids out there that we can help and we’re trying to tune this model so we can ultimately scale in the next few years so.
Scott: I love it man, it’s such a worthy cause and it clearly has value for every single person that’s involved. So, dude, the name of the show is The Competitive Edge and one of the questions I always like to ask at the end is, amongst the entrepreneurs and people that we talked to, what is the one piece of advice that you would give somebody who is aspiring to some of the same things that you have achieved on how they might be able to get an edge in that journey?
Wiley Cerilli: For someone who wants to start their own company?
Scott: Yeah, let’s just go ahead and say for somebody who wants to start their company, let’s say they are in their 20s, or they are working at a traditional corporate job, what’s one thing that they could do whether it’s a ritual, a habit, maybe something that isn’t necessarily obvious but was very helpful to you in your journey?
Wiley Cerilli: So, I would say that one of the most valuable things that you could have is — so when we — as you know we had a lot of office-spaces in — one of the office spaces that we worked out was a shared office down here and so I met like a really great group of CEOs there and we were all in the same phase — [Inaudible 0:59:14] but they had like a desk printed out here and there, Neil from Sale Through, Ross from Seek Geek and Waterfly folks were there and — didn’t know at the time that all these businesses were going grow up and be a big business but I think that going out and talking with other people that are one step ahead of you, can be really helpful.
But establishing a network of different startup CEOs that you can go to for advice and that you can go through this experience with was insanely helpful for me. And you don’t have to go and move into an office space to get that. There’s meet-ups that you can go to; it’s not that I don’t want to complain about the process that we went through but it is a very lonely position to be in, to be the CEO of a company. Everyone is looking to you when things are bad, which things are mostly bad because — things aren’t mostly great, you work through most — everybody says the startup world is straights and gutters, mostly gutters; the straights come along just so often enough and every month and half or so to keep you in the game and everything.
It’s a grueling process that a lot of people can’t understand how much your body and mind — takes its toll on you and so have a network of some other people who are going through that, helps you normalize the process a bit so you don’t feel so crazy. So, all those times which, by the way, up until the day that we signed with Google, I had an amazing day, up until that day I was scared out of my mind that I made the wrong decision 90% of the time. And it’s a tough [technical difficulty] especially at the same time when you are trying to sell this dream and it’s not by the way that I didn’t think that this business was a good idea and wouldn’t ultimately be successful. Like Vincent Bardy said, ‘we never lost a game, we just ran out of time’ and it’s the same thing with the startup world.
I didn’t think that this idea of SinglePlatform was a bad idea, I didn’t think that we were going to lose, because I knew that it made sense. I was afraid we were going to run out of time and so going through that process with some other CEOs that have gone through that is such a great support group to normalize your thoughts and just to talk through things with, that you can’t with your people in your organization because you are either focused on hitting where the goals are trying to hit, I would say is one of the most helpful things for someone about to be a CEO to talk to people that are going through that process and people that are one step ahead of you that are saying, ‘do it’.
And having that group of people around there supporting you that are going through it feels like you are able to go through this thing together and I mean honestly like Neil from Sale Through and Irvin and Dean from Warren and Paul and these guys are in my CEO network and I’m doing to another CEO network group that we meet once a month and sort of have group therapy with First Round Capital [Inaudible 1:02:24] is an awesome dude, all these folks we meet on a regular basis and get good advice, so that is what I would suggest.
Scott: That’s great. And you know, it’s funny, I haven’t read the book but I guess the guy — I think his name is Brad Horowitz from Andreessen Horowitz just wrote a book about like startups the hard stuff and I think the most popular chapter or the chapter that has resonated with the most amount of people that I have talked to who have read it, is the one about how the most difficult part is developing the emotional fitness to be a CEO of a startup.
Wiley Cerilli: It’s exhausting.
Scott: Yeah, and we, generally as humans, we also suck at evaluating the realistic part of a situation; it’s like the classic, you do nine things awesome, you do one thing sucky, you focus on that one sucky thing. And I think a peer group really alleviates that in an excellent way and so I’m happy you brought that up.
Wiley Cerilli: Yeah, it does. It definitely — the process weighs on your relationships with your friends, your family and whoever you are with; like at that time with me, [Inaudible 1:03:40] weighed on us and you need to remain positive and it’s a scary process to go through. But an amazing one, we rather [Inaudible 1:03:48] or not, you learn so much going back to the [technical difficulty] but yeah, I’d definitely suggest that.
Scott: Great parting advice Wiley, we’ve talked about everything from presales to how you rode your bike across the country and now rewarding benefits of working with something that you really care about. And I just want to thank you for coming on the show today, it’s been awesome and I want to also make sure that if people who are listening to his want to get in touch with you and want to learn more about Manitou, they have an easy way to reach you or find out more info about you. So where would you say is the best place for people to get more information on you and Manitou?
Wiley Cerilli: So, I can actually give you the video, I don’t know if there’s any way you can put it up —
Scott: I can totally put it up.
Wiley Cerilli: It’s a video but the video is probably the best thing that we have, it’s the Manitou experience dot org and then otherwise people can email me at WCerilli at Gmail dot com.
Scott: Awesome dude.
Wiley Cerilli: We got sponsors like Tesla and all these great VCs sponsoring our events and so there we’re looking for sponsors and volunteers for camp and auction items and so — whatever people would like to help out with.
Scott: Love it man, thanks again for coming on. You were awesome.
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