Deep Listening with Oscar Trimboli and Scaling Your Business with Allison Maslan

Deep listening is five-dimensional. It’s a way to think about listening in color rather than just listening in black and white. Oscar Trimboli, former Marketing Director at Vodafone and Microsoft, is someone who knows the power of being a deep listener in business and in life. He talks about the value of listening to what’s not said, exploring consistently and deliberately, and how our senses impact our perception of what we hear and understand.


All businesses want to scale, but in reality, entrepreneurs are afraid of risks that they end up doing nothing. Allison Maslan, an author and the CEO of Pinnacle Global Network, guides you in taking that step forward as she shares how scaling is about looking at your business in a very creative way, taking down the misconception that it’s about growing fast. Allison’s book, Scale or Fail: How to Build Your Dream Team, Explode Your Growth, and Let Your Business Soar, teaches helpful strategies for people to scale their company.

TTL 435 | Deep Listening


We have Oscar Trimboli and Allison Maslan. Oscar is the author of Deep Listening. He’s the former Marketing Director at Vodafone and Microsoft. Allison is the CEO of Pinnacle Global Network and we’re going to talk about listening and how to develop organizations to get to develop at scale.

Listen to the podcast here

Deep Listening with Oscar Trimboli

I am here with Oscar Trimboli who is on a quest to create 100 million deep listeners in the world. As a former Marketing Director at Vodafone and Microsoft, Oscar has always been passionate about the importance of listening to his customers. It’s so nice to have you here, Oscar.

I’m looking forward to listening to you.

I love that it ties into curiosity. You’ve got quite an interesting background. I mentioned that you were a Marketing Director at Vodafone and Microsoft. Can you give a little bit more background on how you got to that level? That’s pretty heavy duty.

It’s an unusual place for somebody who started life in accounting to end up in a marketing role, that’s for sure. Straight out of high school, my father who’s a first-generation migrant from Italy encouraged me to study, go to university and get a job as an accountant because they’re not going to be out of work. That was a great plan and I was a bit bored at the university studying full-time. I got a full-time help and studied part-time. Six weeks into my job, my manager did a quick test with me because in the days I was doing spreadsheets, they were actually paper bag spreadsheet that was about A3 size and you did them with a pencil. When you’re a manager, you could graduate with a pen but I was getting the map of accounting role. Robert, my manager, read out twenty telephone numbers to me and I was continuously transposing them. Instead of writing 919, I’d write 819 or something else completely different.

They called me in and said, “Your career in accounting is probably over. You’re not going to get very far if you keep changing these numbers around.” I was so excited the day caller ID came into the telephone world. I was meeting all these new people because of dialing the wrong number. That sent me on a career in software and marketing. Not a wide range of roles and probably that’s what’s tuned my listening need. I always came from a place of I don’t know a lot about the roles. If I listen to the people and their problems, I’ll be happy to solve those problems for them faster. I ended up in a career for the last eleven years at Microsoft in marketing, sales and operational roles, finishing up with five years as the Marketing Director of Microsoft office division.

It’s interesting because I had Rich Karlgaard on my show. He was talking about how he spent five days riding in a car traveling with Bill Gates and he was talking about how they pride themselves on having a high IQ group. You must have a high IQ if you worked at Microsoft. Part of what makes people successful in addition to having a high IQ is their EQ, which you have if you value what you get out of listening. I wrote my dissertation on emotional intelligence. I’m fascinated by what we get from our interpersonal skills and our ability to have empathy. The ability to listen is imperative for empathy. You talk about something called deep listening. I’m curious about what deep listening is.

Most of us listen in black and white. We listen for words and we watch the body language, but deep listening is five-dimensional. It’s a way to think about listening in color rather than just listening in black and white. The difference between what I would call a recreational listener and a deep listener is a deep listener listens to what’s not said. I know that sounds a bit of a yoga statement to say what’s not said is what you have to listen to. If you understand the 125-400 rule and the 125-900 rule, we speak at 125 words a minute. We can listen to 400 words a minute and the speaker can think it up to 900 words per minute. The likelihood that the very first thing that comes out of somebody’s mouth is a well-articulated representation of 900 words in their mind. You’ve got one in nine chance that’s going to be right. I don’t know about you, Diane, but if you went for surgery and you were given a one in nine chance of surgery survival, you’ll probably ask a second opinion.

Very few of us get a second opinion when we’re listening to somebody. They might start off with a statement that may be about the background or it might be about the context of the situation. We immediately use that in the Western voice. Eastern orientation around listening, particularly in high context cultures like China, Korea and Japan is very different and the world becomes more global for business. The reality is if you can spend a little bit more time with a very simple question, if there’s one thing you want to take out up to the last conversation, it’s this, “I’m curious, what else were you thinking about on this topic?” I love that that’s your word, curiosity. If you can get them to explore what else they’re thinking about on this topic, you’ll hear some magic code words and the audience will be nodding as we say that. The speaker will draw in a breath after you say that. They’ll say words like, “Actually,” or they’ll say, “Do you know what I haven’t told you that’s really important?” or they’ll say, “The critical issue is,” or they’ll say, “Honestly, if I thought about it a little longer, this is what matters.”

Typically, as they are accessing that thought, you’ll notice that breathing goes deep and they have a big exhale. It sounds like a sigh. When they do that, they’re spending a little bit more time listening to what they’re thinking. “Although you’ve done nothing more than pose the curiosity question, I’m curious what else were you thinking about on this topic?” You’re helping them get rid of those other words in their head. Even a washing machine has more than one rinse cycle. Our brain is a lot like a washing machine in the suds cycle when we’re thinking about things by ourselves, but when we talk about it, it’s like a rinse cycle. The clean water comes down and gets the idea out into the world. For the deep listeners, they’re exploring consistently and deliberately what’s on said. It’s not for the listener, it’s for the speaker to discover what matters to them. As a result, you get told, “You’re a good listener.”

[bctt tweet=”If you want something, go get it and make it happen.” via=”no”]

When you’re saying this, this is making me think of not just curiosity but perception. Our senses impact our perception of what we hear and understand. We may think we’re listening but are we perceiving in color because we’re perceiving based on our cultural norms and what we think things mean? How much does all this impact our perception?

I’ll feel this play a critical role, whether it’s our origin story, whether it’s our sequencing birth, whether you’re a firstborn, second born, third born, your language, whether the language you’re speaking in is your native tongue or it’s not. What experience that you might have, whether that’s in business or individual relationships. One of the things we spend a lot of time talking about is in the ‘80s and the ‘90s, there was an amazing movement called the Active Listening Movement. A lot of people being trained through the Active Listening Movement that paraphrase and engaged the person speaking. As powerful as that is, the most important person you need to listen to is not the speaker.

The most important person you need to listen to first is yourself. For a lot of people in corporations, they’re running endlessly from meeting to meeting and homemakers are doing the same things. They’re picking the children to school. They’ve got chores to undertake. They’re thinking about what they need to prepare for dinner or what they need to do for the weekend, around sports and all these things. We have so much noise going on in our head that we’re not available to listen to the other person and overlay that with modern distractions like technology, but you’ve got a whole bunch of bludging going on in your head.

You’re talking about what you need to do apart from listening to this conversation. You’ve got technology distractions, whether that’s a cell phone or a laptop or an iPad or all these other things. Your foundations of listening completely evaporate. We’ve done some research with 1,410 people. We’re in two to three years of study with them. The three things that consistently blocked them before they can get to those filters is their attention, distraction and focus. All of it is a self-orientation and the listening because they’re not available to listen to the other person, plus their mind is completely taken off with all the other things happening in their world.

Are those the four villains of listening you had mentioned about?

The four villains show up that way. One of the four villains is the interrupting listener. The minute you draw breath, they give you their opinion and it’s the most visible of the listening villains. Another listening villain is the lost listener. That’s the one that I just described. They’re completely lost in their own thought. They’re not even sure why they’re here or if they’re here, they’re not completely present in the dialogue. They’re drifting off because the speaker can’t speak fast enough for them. If you go back to the 125-400 rule, that speaker speaks at 125 words a minute and you can listen to 400 words. It’s happening to you whether you’re driving, walking or wherever you are, you’re filling in the gaps because I’m thinking way too slowly for it. The other two villains of listening are the dramatic listener. They love listening to you because they’re going to tell a bigger story. If you’ve had a bad boss, they’ve had the worst boss. If your project’s a disaster, they have a bigger one. If you’ve got divorced, their divorce was worst.

They love listening to you because it puts them on the state of a melodramatic story about you and them. Finally, the shrewd listener. The shrewd listener is the one which you think is a good listener. You can picture them with their hand on their chin and looking at you intently and they’re not doing that at all. All they’re doing is problem-solving. They’re saying, “You think that’s your problem? That’s your simplest problem. I thought of three more problems and the three solutions. I wish you’d hurry up and catch up with one.” This proportionally represented in the sales professions, the consulting and professional services industries, accountants, lawyers. Those four villains are present in all of us because listening is situational and relational. We listen differently to our parents and we would have thought that we listen differently to a boss than we would to a coworker. We listen differently to children than we would to a lawyer for example. Those villains show up differently, but we have a predominant villain that shows up for most of us.

I talked to another guest who was saying if you look at an email somebody sent you, in your mind, if it came from the person you trust the least, you’re going to interpret it a certain way as compared to the same person you trusted who completely said the same exact thing. You’re going to have a glowing view of it compared to the other person. We do the same thing with listening. It also brought to mind what you said on paraphrasing because I have a lot of students who I still teach business courses to. With their courses, I won’t let them directly quote. I make them paraphrase their citations because I want them to show that they’re able to digest information and put it in their own words and still give credit to the author. Being able to paraphrase what people say can be helpful. Just because we’ve heard something doesn’t mean we’ve understood.

Paraphrasing has its plot, don’t get me wrong, particularly when you’re dealing with abstract, brain work or thinking methods or new concepts that have been described for the first time. A simple phrase, “If I heard you correctly, what this means for me is,” and you’d explain them. That gives the speaker an opportunity to go, “It’s about 80% there, but here is the 20% that I didn’t explain properly or you didn’t get.” Paraphrasing definitely has its place, but it’s not the only technique in the journey to moving from listening in black and white to listening in color.

TTL 435 | Deep Listening
Deep Listening: There’s so much noise going on in our head that we’re not actually available to listen to the other person.


What made you interested in listening? Did you have a time that you didn’t listen and you thought, “I need to help people with this,” or did you work for somebody who didn’t listen? What was the point where you thought, “I need to help people with this?”

I’ve been unconsciously competent as a strong listener. I went to a school with 23 nationalities and we played card games in English. We played Italian card games. We’d play with Chinese card games. Looking back, it was always played in pairs. Quite often, I was asked to be in pairs. Remember, I am atrocious when it comes to math. I wasn’t a very good card counter. There must have been some reason why these people were getting me on their team. I could read the body language of those people playing cards better than anybody else. In hindsight, I say that now. It was many years ago where a vice president of Microsoft said to me, “Oscar, that’s amazing.” We’re in a very tense meeting where we were dealing with global, regional and local issues around the big transformation that Microsoft was moving from charging people right up front to charging them a month.

Tracy looked at me after the meeting and she said to me, “You’ve been told you’re a good listener and I know you’re a good listener, but I want you to understand this. Not only do you hear people, but you see who they really are. If you could code that, you could change the world.” At that moment I thought nothing of it. In fact, the two years I thought nothing of it, then somebody else said to me who was in that meeting, who heard what Tracy said, “What are you doing about getting that coded?” When you’re at Microsoft coding it literally means make it into software. I went on this journey to go, “How would I code something as abstract and immaterial as listening?” What I did was I worked with a bunch of students in our graduate program. A lot of Microsoft graduate were second, third round picks. We weren’t getting the cream of the crop. I went through a process of listening to everybody for the last three years who’ve been in the program, who either left and went to the competition or didn’t join us and went to the competition.

This little petri dish of experimentation around how do you listen beyond the words in this graduate community? That program that we designed from that ended up taking 26 theories around the world. That same vice president said to me, “This is your calling. Stop wasting your time selling software. You can make a bigger difference in the world teaching the world how to listen.” That started the journey to where I am with the research, the books, the podcast, and playing cards and jigsaw puzzles. We’re working on Alexa and Google Home app that will be a listening coach. It will listen to your conversation with permission, then 30 minutes or whenever you schedule it, you’ll say, “Alexa, debrief me on that meeting.” It will say something like, “At the twenty-minute mark, you were using too many why questions. You interrupted twice at the 30-minute mark and the 35-minute mark, only three people spoke. Don’t practice those things the next time.” One hundred million listeners sound like a lot, but when your perspective is software, it’s completely possible. I’ve got a lot to thank Tracy for.

I was wondering if she might turn on when you were saying her name, but she didn’t. I could see that she’s listening to me all day. Some of the time she can hear the guest in a situation like this on Zoom. Some of the time when I’m on my phone, she wouldn’t be able to hear both sides of conversations. She’d probably think I was a horrible listener because she’d only hear one half of the conversation. It could be helpful to somebody to do that. I love that you’re working on this because you say that only 2% of the people grasp how important listening is as being a good skill or good at it.

If you think about the twentieth century with the movement and a whole bunch of people that’s created an industry around teaching people how to speak. That’s awesome, but it’s got us into a world of back to back meetings, chaos, confusion and conflict in the world. I think the leadership hack of the twentieth century is understanding how to listen. In the minimum, 55% of your day is spent listening, yet 2% of us have ever been trying if we can remember our English teacher and our math teacher, but no one can remember their listening teacher. Do you remember yours, Diane?

No, I don’t.

The teacher you remember the most, I guarantee you is the one that listened to you the best.

That’s funny because I wrote my book on curiosity and I dedicated it to my favorite teacher. He made me the most curious and he did listen very well. Listening requires that you ask the right questions. Do you deal with the question aspect?

[bctt tweet=”The teacher you remember the most is the one that listened to you the best.” via=”no”]

Yes and no. A great listener is skillful in asking questions. I think the Western orientation of listening is all around the dialogue and the questioning. The role of silence is much more emphasized in the East, to stay still in the moment. A lot of native and ancient communities, whether it’s the Australian Aboriginal communities, the Inuit of North America and many tribes in Africa and Central America will sit around campfires in whole silence for a significant period of time. As a sign of respect, they’ll listen to what everybody’s thinking, but not saying anything. For a lot of us in the West, we get trapped into thinking questioning is the only technique. Let’s talk about some of those questioning techniques.

We probably spend too much time in the West asking why entitled questions that sound rather judgmental. “Why are we doing this? Why did you do this?” We even have methodologies called the Five Why’s in corporate settings. To understand how people are thinking, practice more of what questions and how questions. “If you arrive at this conclusion, what assumptions do you think you haven’t explored so far? Where else could this apply that we haven’t considered? If we were to come back in ten years’ time, is this the most important thing we think we need to discuss?” These questions are context-based questions to help the listener and help the speaker explore their patterns. One of the more frustrating things is if you just ask questions, when you’re the listener, you reduce trust. As you ask more and more questions, the speaker doesn’t feel you’re fully understanding them and you’re not fully getting them.

That’s where the role paraphrasing comes in. If there’s one thing I’d encourage everybody to do is to tone down your why based questions. The only time we ever heard why when we were growing up, maybe five, six or seven, was when our parents yelled at us and say, “Why did you spill the milk? Why did you do that?” There’s a lot of shame associated with why based questions. The minute you ask somebody why, and that feeling they’re not safe when you’re asking that question, they’re going to be triggered. The amygdala, the part of the brain that’s the most primitive will shut down, any thinking part of the brain as well. Whereas how and what based questions will help them to explore future or entitled possibility rather than significant events that came from that path.

It’s making me wonder if you’re an introvert more than an extrovert. Am I correct?

The answer is it depends. I think introversion, extroversion, omniversion is situation and relational. Compared to a lot of software engineers, I’m a raging extrovert. Compared to a lot of sales people and a lot of marketers, I’ve come across as a raging introvert. If you think about how Susan Cain describes it in a book, where did you get your most energy from? I get the most energy being by myself and just relaxing and having that quiet time. Yes, I’m an introvert.

I loved your book. It opens up a world of discussion. I came from a sales background where everybody was an extrovert when I was in it. Now, we’re seeing a lot more introverts because we need more listeners and sales are teams more now than in the past. It’s a nice balance. I could see what you’re talking about is so important. I always share a lot of my mortifying not listening stories on my sales speeches I give because I had quite a few times when I could have been a better listener. Do you have a reason why you want to share with why it’s important for leaders to be good listeners and how they can learn to be a better listener?

There are many examples of the cost of not listening immense and prolific, but the one that comes to mind and most people will be aware of is the BP deep horizons oil rig off the coast of Louisiana. We’re a couple of years down the track from that disaster, which cost seventeen lives and still counting $54 billion for BP. The engineers who were on the oil rig, Halliburton who designed the oil rig had told BP on numerous occasions, “These are the operating parameters that it’s designed. If you go outside it, there will be a significant risk.” The engineers who were operating on the rig knew because they could literally feel the rig moving. They were trying to tell the managers they couldn’t make this production. They know they couldn’t go any faster because those managers weren’t listening to the staff. The engineers put their hands on the rig, who actually looked at it as they were coming up from the rig. That cost, in that case, was extraordinary. Not just in terms of legal costs, in terms of financial cost to the tourism, the fishing industries and all the jobs lost along that coastline.

We can see many other examples around the US. The 2016 election. I spent some time interviewing the editor and chief of Huffington Post. They said they didn’t spend enough time listening to the issues that mattered to people, not the issues that mattered in Washington. As the Democratic Party wasn’t listening to what was being said in the heartland of America, somebody else decided to listen to them and we have a different political climate as a result of that. What Huffington Post did, they learned from their mistakes and they created a bus tour around twenty cities in the middle of America and spent two days in each city. It was called Listen to America Tour. What they understood very quickly was the issues that mattered are with family issues, with healthcare issues, with jobs issues in the middle of America. They started writing stories about that rather than the headlines that were coming out of New York, California or Washington DC that most of these people didn’t care about. Whether we look at politics or whether we look at oil rigs off the coast of Louisiana, the cost of not listening is extraordinary.

TTL 435 | Deep Listening
Deep Listening: Impact Beyond Words

I couldn’t agree more. You’ve made such great points. Many people would like to know how they could learn more from you. I know you are @OscarTrimboli on a lot of websites and Twitter, but is there a link you’d like to share or information you’d like to share with anyone?

Listening is an awareness issue for most of us. 86% of people think they’re above average car drivers and 83% of people think they’re above average listeners. If you go to, you can download the five myths of listening and more importantly what you can do about it. That will move you from a recreational listener to a deep and powerful listener.

It’s so nice of you to offer that to my audience. It was so wonderful to have you on the show, Oscar. Thank you. I know you’re such a busy guy. I appreciate you joining me.

Thanks for listening to me.

You’re welcome.

Scaling Your Business with Allison Maslan

I am here with Allison Maslan who is the CEO of Pinnacle Global Network, the world leader in scaling businesses. Her book, Scale or Fail, is a Wall Street Journal bestseller that’s endorsed by Barbara Corcoran and Daymond John of Shark Tank. Allison’s been about everywhere. We’ll uncover some of it as we go along. It’s so nice to have you here, Allison.

Thank you so much for having me. I’m excited to be here.

You’ve been featured everywhere: Success, Fortune, Fast Company, Inc., Forbes. I was looking at this list and it would take me all day to list how successful your book has been. Before we talk about the book, I want to get a little background. A lot of people might be aware that you host your own weekly video podcast, Allie & You: The Business Success and Lifestyle Show. Can you give a little background about how you got to be to this level of success?

I grew up in a very entrepreneurial family. My father built a large chain of women’s clothing stores. I grew up holding onto his coattails and going from store to store and taking it all in. He had thousands of employees. The message I got was if you want something, go get it, go make it happen. I built my first business starting when I was nineteen. It evolved into a full-service advertising and PR firm in my twenties. I had a job for two weeks and I sucked at it. That was the longest that I could keep and my family was a little worried about me. I figured that business was my thing. It’s been over three decades. Anytime you do something for that long, you learn a thing or two and you make a lot of mistakes along the way and you become more resilient but it’s fun. I love business and they are my tenth business. We help other businesses. We help them grow and scale in Pinnacle. It’s fun helping people make their dreams come true.

It’s interesting to always hear people’s backgrounds. I grew up with no one who worked in my family, so it was the complete opposite. I’m always fascinated when you see how people come from completely different backgrounds and yet still be motivated to do different things. You talk about helping people scale and I like how you use that as a part of your method. In your book, you use a scale to stand for something. I’ll let you share what you mean by scale in your book.

A lot of people misunderstand what that means. A lot of times they think scaling means growing fast. It’s not that. Scaling means to take whatever your revenue stream you’re offering is. There’s a certain point where the business owner runs out of bandwidth. There are no more hours in the day. There’s no more that they can offer. They hit a wall and they can’t grow. That’s the time to scale or before you hit the wall. That’s figuring out a way how do we take our product or service and how can we replicate it, so that you’re multiplying your revenue and profits. You’re also multiplying your impact. You’re able to reach a lot more people, but without your expense and your energy multiplying at the same rate. That’s what scaling is. It’s about looking at your business in a very creative way and say, “How do we take this one to one thing and how do we multiply it to one to many?”

A lot of people get frustrated by that. They want to be more profitable and sometimes you’ve got to grow without the profit. Can you explain that? Is that a problem for people to get a grasp of that?

There are periods in your business where you’re going to be investing. You’ve got to invest to grow. It’s how it is. When a plant is going to grow, you have to give it water, you have to give air. It’s not going to do it on its own. There are periods in your business where you’re going to be investing in marketing, you’re investing in the team, things like that, but it should create a good ROI. It’s not just top line revenue, profits are important. Figuring out what is your net profitability quotient. In your industry, is it 10%? Is it 20%? As you grow, let’s say you’re at $1 million and you want to get to $2 million. It’s great if you get to $2 million, but if it’s a $2 million in expenses, it’s tough. You want to keep that profitability, but in some cases, you’ve got Netflix who owe $20 billion. That’s their intention to dominate the marketplace and they are.

[bctt tweet=”A great listener is skillful in asking questions.” via=”no”]

It is interesting to see how some of these companies are going without the profit for a while or the success that we normally would measure it for growth. I found it interesting watching that HBO special on Theranos and her thought process behind everything that she did to grow. Do you think we’re getting too many people that are trying to fake it until they make it?

I personally don’t think that there’s anything wrong with that because how do you know until you do it? At some point, everything you do, there’s always a first time. It’s not about pulling the wool over anyone’s eyes, but I think you have to have that conversation with yourself. Other people don’t get out of the gate because they have so much fear.

It was something I talked about with Chris Yeh, who co-wrote the book Blitzscaling with Reid Hoffman. It was how you have to take certain chances for growth if you want to be the next unicorn, I think everybody’s trying to get to be that. A lot of people are afraid of failure though. You mentioned you built ten businesses, but you said some of them have failed.

Let’s just say within each business there were many failures. The businesses didn’t fail. I didn’t have to go bankrupt or anything like that, but along the way in each business, I’ve had many things that didn’t fail. For myself, what has worked was if I’m going to do business, I decide it’s going to be successful.

That’s a good way to go in, but the fact that a lot of people are so afraid that they become paralyzed. They don’t do anything and then they end up failing. I’m always impressed. I’ve interviewed so many billionaires and interesting people on the show. It’s what people come back from and just say, “Give me more.” That’s what I admire is the fact that they don’t quit. You talk about a lot of things in Scale or Fail that are very helpful strategies for people to scale their company. You have the acronym of SCALE, what does that entail?

What the book covers is strategic vision. The acronym is Strategic vision. C is Cashflow, which is important. Strategic vision is where you have to have the vision. It seems so simple, “I’ve got a vision. I’ve got a mission,” but if there’s a marketing problem, it’s a vision problem. If there’s a team problem or a culture problem, it’s a vision problem. That’s where everything starts. Cashflow would be the scale strategies that I talk about. How do we multiply? It’s also setting yourself up for cash. A lot of business owners are afraid to spend money. They’re afraid to get credit lines. You want to get them when you don’t need them. If you have a product business and you’re importing from China but you’re not getting paid yet, you need to have some money to be able to do that. That’s cashflow and sales, that’s another part of cashflow.

A lot of companies are like, “Let’s get an investor and we’re in the second round of funding.” You’ve got to pay that money back. They’re celebrating that they owed millions of dollars. Not to say not to get investors but be revenue focused company. Focus on driving sales and the rest will follow, then A is Alliance of the team. The team is crucial and you want to build a team that’s going to ultimately take the vision and run with it. That takes you into the L, which is Leadership because it’s generally how are you driving the ship. Are you a leader or are you a boss? Are you telling people what to do or are you inspiring them into action? It’s a completely different scenario and outcome, then the E is Execution.

The leadership aspect, I teach so many online business courses and we talk a lot about the difference between being strategic and tactical. It’s so often that people are great at tactical things or one or the other, but it’s very challenging to be good at both. I found it interesting the way you lay it out because I take a lot of these clips and I put them in my courses. A lot of students can use this information because there’s more than one way to look at this. There’s no one way that works for everybody. You shared seventeen strategies to scale a company in your book. Do you want to share any of those strategies?

TTL 435 | Deep Listening
Deep Listening: When a plant is going to grow, you have to give it water, you have to give it air. It’s not going to do it on its own.


I’ll give you an example with one of our clients. It’s probably the best way. We have a client that runs a company called Dog is Good. They are a lifestyle brand for people that love dogs. It’s actually products for the owners, not the dogs. They like the typical product. They have their products in retail stores across the country, but the retail market is iffy at best these days. There’s not a lot of profit margin when you’re dealing with wholesale. They were having a cashflow issue. We help them create several other revenue streams. We’ve been working with them for a few years now. It’s been fun to see all these things evolve. We’ve helped them develop a subscription program for the retailers. That’s an automated ordering and bundling of products. It makes it so easy for the retailers. They love it.

They also have licensing of their brand and they also do something called an exhibitor program, which is like pop-ups all over the country because they’ve built such a great brand. People love it. She’s giving all of these Dog is Good fans an opportunity to have their own dog as good business. It’s a direct sale. They buy the products from Dog is Good and then they are out selling the products at events and things like that. That become this whole massive sales force and in the last few years, they’ve sold 150 of them and there are other things happening too. It’s taking the traditional model. Right there, I shared subscription, direct sale, licensing and some other things that are coming off of it as well. We get stuck looking at things the same way and then hoping, “If I just work harder, I’m going to make more money.” That is not where the big growth happens.

Can all companies scale? Is this possible for everybody to have that as a goal?

You can scale every business model. Every industry can scale. You may have to shift the model. If you’re a dollars per hour person and you’re the accountant or the bookkeeper, you have to build a team that does what you do. For instance in my business, Pinnacle, we have nine mentors that work with our clients. It used to be me. I used to be the only one, but I can only help so many people. We have an unbelievable team. They’ve all built really successful companies. They’ve all been in the trenches. They work our methods and they work with the clients. In that way, we’re able to support a lot more people and I’m not working 24/7 falling over from health problems.

How long did you work as you being the major focus until you started to have other mentors?

I was doing the mentoring myself. I did one-on-one for a couple of years and then we started Pinnacle. The first year it was me and then one other coaching assistant and then we started growing. I went from one mentor and then I hired four. The thing is, having the guts to take that leap because so many people are like, “If I hire one person, what if I can’t keep them busy? What if I can’t pay them?” There are a lot of ifs. That’s what keeps you small though. All the things that you’re afraid of, you’re already doing.

When I’m doing some researching on my book on curiosity, one of the things I found that held people back was fear. Their assumptions, which are the things that they talked about in their head, the voice of all the things they think they can’t do, technology and environment. They get so wrapped up in what they think they can’t do and they don’t do anything. About 85% of what people are thinking and worried about happening doesn’t happen. You’re sitting there worried about nothing. As you were talking about growth, it made me think you had written something about super pros of business. How do they come into play as companies grow?

Super pros is a powerful concept. There are so many parts of the business. You have sales, you have marketing, you have team, you’ve got legal, you could go on and on. It’s overwhelming trying to juggle all of those things. What I’ve done is pared it down to four quadrants of your business. Think of a table with four legs and you think of that as your business. If one of those legs is wobbly or non-existent like most businesses are, it’s going to fall over. The four quadrants are products and revenue streams, that’s one. The second quadrant is traffic. How do you drive business to you if you’re marketing? Sales conversion is the third one and fourth is operations. Those are the four legs of your table. Are those humming in your business and who are running those? Most business owners have their hands in at least three of those things. What you want to do is if you have an expert running those quadrants, you pick the one that you feel that’s your super pro. What area do you shine in out of all of those four? Is it revenue streams, sales, traffic or operations? You stay in your lane, you get an expert for the other three, then you’ve got this sturdy table. The next step is to then replace yourself.

[bctt tweet=”When you’re micromanaging, you don’t give people a chance to shine.” via=”no”]

It’s very hard for a lot of people. I’m thinking to your four legs. I’m wondering which one you’ve run into the most problems with when you’re consulting with people. Which of the four legs doesn’t hold them up the most?

Probably sales and operations. Most business owners get bogged down in the operations and the details. If you figure the business owner’s value is worth $500 an hour and they’re doing the books or running errands or booking airplane flights, they’re losing money. Their value is working on the business strategy, building relationships and building a strong culture. That’s where you start seeing the big growth. It feels scary to feel, “I’m stepping back. My clients just want me.” It’s not true, you think it’s true. It is ego because they want to be taken care of. When you can step out, your business will run better. There are people that can do those things better than you believe it or not, but when you’re micromanaging, you don’t give people a chance to shine.

I used to run the MBA program at Forbes, and I was thinking of all the courses I’ve put together to help people be prepared when they got out. I’m curious what you’re seeing you think that maybe they need to teach more at the university systems, that maybe people are trying to do and figure out on their own. Is there anyone skill or any one thing you think universities or even people who don’t go to universities need to work on to be the most effective?

I’m a very experiential learner. Just reading about it in a book is not going to help me. I need to live it. The more on the job opportunity they have to be in the real world of building a business and what’s it like. Unless you’re the one looking at the bank account and wondering how you’re going to make payroll, that’s the real-world business education. I think working and building teams. The biggest thing that is so important to a business owner is revenue. It’s sales. A lot of them get caught in the details and they forget to bring cash in and then all of the sudden, they’re like, “How are we going to pay for this?” If they were focused on driving in every day there has to be revenue coming in, that solves most problems.

There are so much to do when you start a new business. A lot of people want to hit it big right off the bat. Do you think it’s better to have your sights set for a smaller company or is it good to think like Elon Musk right out of the gate?

It depends on the person. Not everybody wants to be an Elon Musk. You could have a lifestyle business. It’s just side hustle thing that you’re doing or you want to keep it small. It depends, but if you scale it right, people think bigger means I have no life. In the traditional sense, yes, but it doesn’t have to be that way. If you are all about your team and you leverage them for their creativity, their eyes, their ideas and you get them so psyched about your vision and your mission, then they’re the ones that take the ball and run with it. You can scale. We’re seeing it all the time. I interviewed Alli Webb of Drybar. She spoke at one of my events. I have a lot of events. I have another event called Scale. She spoke at that event. I can’t remember how many stores exactly, but once they got to sixteen stores, they brought in another CEO.

Where is Drybar? Is that in Arizona or California? I can’t remember.

TTL 435 | Deep Listening
Scale or Fail: How to Build Your Dream Team, Explode Your Growth, and Let Your Business Soar

It’s in California. He lives here and I can’t think of his name either, but he was the CEO of Creative Nail Design. That’s a company that has been around for 30 years. Jan Arnold, she also spoke at my event and she’s an amazing lady. She sold it to Revlon for $600 million.

All that you write about and you talk about on your shows and the different things you do are fascinating to me. These are all the kinds of things that I’m interested in. Do you have something you’d want to share or a website or something that you can let everybody know how to reach you?

We have an online gift, which is a five-video funnel on scaling since that’s what we’ve been talking about. To find me directly, just go to You can also read the book at You can get all the information about the book there, but the free gift you go to

Allison, it was so nice of you to join me on the show. All your work is important. There are many people who struggle with this. Scaling is a term we hear every day and everybody’s trying to figure out what it means and how to do it. You have some great information and I hope everybody reaches out to you. Thank you for being my guest.

You asked some great questions, so I appreciate sharing this information. Thank you for having me.

You’re welcome. I’d like to thank Oscar and Allison for being my guests. If you’d like more information about Cracking the Curiosity Code or the Curiosity Code Index, you can go to I hope you join us for the next episode of Take The Lead Radio.

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About Oscar Trimboli

TTL 435 | Deep ListeningOscar Trimboli is a quest to create 100 million Deep Listeners in the world. As a former marketing director at Vodafone and Microsoft, Oscar has always been passionate about the importance of listening to his customers. Oscar and his teams were renowned for time listening to customers in the call center as well as the market research summaries. Oscar brought this passion to next generation leaders at Microsoft, rebuilding their graduate leadership program which was implemented in 26 countries.


About Allison Maslan

TTL 435 | Deep ListeningAllison Maslan is the CEO of Pinnacle Global Network, the World Leader in Scaling Businesses. Her new book, Scale or Fail is a Wall Street Journal Best Seller that is endorsed by Barbara Corcoran and Daymond John of Shark Tank. Allison’s built 10 successful companies starting out at age 19. Now, she and her team of CEO Mentors pay it forward helping business owners worldwide scale their company while, at the same time, create a passionate life. Allison’s been featured in Success, Fortune, Inc, Fast Company and Forbes magazines, is a regular contributor to Entrepreneur magazine, and a featured expert on ABC, CBS, NBC, CNN across the US. She also hosts her weekly video podcast, Allie & You: The Business Success and Lifestyle Show.



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