137 Scale or Fail: Serial Entrepreneur Allison Maslan on How She Scaled 10 Businesses to Multimillion-Dollar Success

Allison Maslan knows first hand the secrets of scale: She has built 10 businesses into the 8 and 9 figures and now pays it forward to entrepreneurs and business owners as CEO of Pinnacle Global Network, a mentoring and mastermind company. Her new book, Scale or Fail, debuts this October, and she shares how it was burnout and a devastating car accident that enabled her to “get out of her own way” and master scale.

Melinda Wittstock:         Allison, welcome to WINGS.

Allison Maslan:                 Melinda, I’m so happy to be here.

Melinda Wittstock:         Oh gosh, me too. I’ve been excited about this interview for some time because I look at your career and I see somebody who is brilliant, not only as a serial entrepreneur but someone who knows how to scale companies, all kinds of different companies, and do it from the outside looking in, certainly with ease, and so I wanted to ask you, how early in your career did you know that you had these entrepreneurial superpowers?

Allison Maslan:                 Well, I often say I came out of the womb as a business owner. I grew up in a very entrepreneurial family. My father built the largest chain of women’s clothing stores that were privately owned in the United States starting 1955 through the early 80’s, and so I was hanging on his coat tails, going from store to store, in my earlier life, and I thought, gosh. I want to do that. I want to be like him, and I remember when I was 12, I was in the car with my dad and he said, “Ali, you know how to start a business?” And I was like, “No, dad. I’m 12.” And he pulls out a business card and he goes, “You just print a business card and you’re in business.” And basically he was saying, if you want something, go make it happen.

Melinda Wittstock:         What a wonderful lesson because so many kids grow up around people who are not entrepreneurial and kids in the education system and so many things reinforce this idea that you’re supposed to fit in. You’re supposed to be a good soldier. You’re supposed to work hard. Do all the right things. Tick all the right boxes, and yet to be an entrepreneur really is to color somewhat our side the lines, think of things that other people haven’t done and really kind of live differently, so to have that permission at age 12 is a game changer.

Melinda Wittstock:         How did it feel for you compared to say your friends who had ‘civilian’ parents?

Allison Maslan:                 It’s interesting but I never thought of it that way because it’s all that I knew. In fact, I didn’t really even compare myself-

You know, in fact, I didn’t really even compare myself either because I didn’t really probably fully understand where their parents were coming from. You know, the mentality was always you got to work hard and there was a lot of expectation there. He just didn’t really care how I did it or where it came from. I just need to find something and work hard and I couldn’t hold a job for more than two weeks. I mean, I was just bored out of my mind and I was pretty much unemployable.

So I thought, if I don’t figure out this entrepreneurial thing, I’m in big trouble, you know? So, yeah, and I didn’t have a trust. There was no money coming from my family, nothing. They were, like, woo, you’re on your own. And I’m so grateful for that because I knew that I wanted to make it on my own and I knew that if I didn’t make it happen … Well, actually, in my mind, I thought, it is going to happen because I want to create a nice life and it’s really got to be up to me. So, looking back, I appreciated that, having my back against the wall.

Melinda Wittstock:         Yeah, often, we have to get out of our comfort zones to be able to innovate and just be a little hungry, I guess. So your first business, you know, as an adult. You’re 19. What was the first business and what prompted it? What was the idea and the spark behind it?

Allison Maslan:                 Well, I loved writing poetry and so I created a company called Expressions by Allie and I was in college at ASU and I started doing personalized poems for birthdays and anniversaries and I would do calligraphy, right. So I was making, like, 25 bucks a pop and I though, oh my God, this is it. I’m going to be a poet!

And I told my dad, I’m like, “Dad, I founding my calling. I’m going to be a poet.” And he’s like, “Oh, Allie. That is so great. I’m so proud of you. But did you know that most poets don’t become famous until they’re dead?”

Melinda Wittstock:         Oh dear, talk about a dream being crushed.

Allison Maslan:                 Thanks a lot. But that really lead to, people would say, “Well, do you do greeting cards?” Or “Do you do brochures, do you do television, do you do radio?” And I just kept saying, “Yes. Absolutely, I do that all the time.” And then I’d be, oh my God, what am I going to do? I have no idea how to do any of it, but I wasn’t afraid to ask for help, so I would hang out at the printer. I would hang out at the radio station, or the TV station, and I’d say, “Teach me everything I need to know.”

So I had some incredible mentors at that young age and so by the time I was 25, I had a full-service advertising and PR firm in San Diego called the [Barrali 00:20:10] group and we had clients, Ben and Jerry’s, Supercuts, Charlotte Russe, really just from saying yes and then hustling my butt to figure out how to pull it together and make it happen.

Melinda Wittstock:         That’s amazing by 25. I mean that is awesome. And so you scaled that company. You start out with sort of as a full-service ad agency. What was it like to do that and did you, at a certain point, say oh my goodness, agencies are hard to scale?

Allison Maslan:                 Yeah, so for the rest of the course of my life and, really, what my upcoming book is about and that is that I was great at bringing in business, I was great at flying by the seat of my pants, but, Melinda, I had no idea how to delegate, build a team, do logistics, systems, all of those things that are crucial. Maybe not sexy, but crucial in building a business and so I was falling apart at the seams. I was miserable, depressed, on the brink of breakdown, really, and ended up having a car accident that was, you know, I shouldn’t have made it. It was a miracle.

And that was a huge wake-up call for me, where I said, “Okay, I can’t live like this anymore.” I love this business thing, but I need to figure out how to do it in a way that it can scale and that I actually can build a business around my lifestyle, because I wanted to also have a personal life, spend time with my daughter, and all of that good stuff.

And so I took a year off, really studied what worked, what didn’t, what was working with companies like Supercuts and Ben and Jerry’s and these Fortune 100 companies that were my clients, and then came back with a vengeance and took all this marketing knowledge I had learned building this ad agency, and then went from there and really built this scale model so that I could step out, run the company, but not work in the company, and that’s where so many business owners get stuck and end up really quitting and shutting their business down.

Melinda Wittstock:         Yeah, exactly. Well, it’s just that moment where you’re doing something that you love to do and you do more of it, and you have to suddenly keep doing more of it, keep doing more of it, and it’s impossible for any one person. So unless you do master that delegation, you’re either going to be and burn out, or you run a business that never makes it anywhere near a million dollars.

Allison Maslan:                 Exactly. And that’s exactly what was happening to me. I mean, the business was running me.

Melinda Wittstock:         Yeah. Yeah. I mean, we see so many women actually in this situation – we launch businesses, we tend to, that we’re really passionate about and I think that’s great, but there’s also a downside to it. If you launch a business around something that you are really good at doing personally, like, hey, I’m a great copywriter, so I’m going to launch a copywriting business and then you end up doing all the copywriting for example. Or I’m a great software developer, and you end up writing, doing all the code yourself, like, I mean, that’s going to crush you. Basically, you’re creating a job as opposed to a business.

Putting the business around that passion can sometimes actually take the passion away. So how early should women really start thinking about asking for help in the sense of hiring and putting systems in place? Let’s break it down a little bit. Like say, for instance, hiring. Most women, I think, hire too late. So who are the first people you should be thinking about hiring?

Allison Maslan:                 Yeah, so this is a great question and I outline in my new book that’s coming out called Scale or Fail, and you can actually get it on pre-sale right now on Amazon, is five phases to build a self-managed company and that means how you actually take yourself out of the equation.

Allison Maslan:                 So the very first phase is you’re doing everything, right? You are the domain. You’re the solo-preneur. But pretty quickly, you need to shift into phase two, which is what you’re talking about and the hires that I would recommend initially are an assistant, so that you’re not running errands or going to the bank, or, you know, they’re able to send out emails, handle your calendar, free you up, right. Then a marketing person and a bookkeeper. So I would say those three are pretty crucial and statistics show that if you hire within the first six months of opening your business, just hiring an assistant, you will get to seven figures so much faster, like in a fraction of the time.

Melinda Wittstock:         Well, you know what’s interesting, is you start exercising your delegation muscle and it becomes easier and you start learning about how to manage other people or motivate them or inspire the, right, all of those things, which you kind of need to practice to get good at it.

Allison Maslan:                 Oh, yeah. I mean, there was a wake-up call for me when I saw, I have to shift from boss to leader and this mentality of just telling people what to do versus, as a leader, inspiring them to take action, is a whole different ball game.

Melinda Wittstock:         Right, because you want to create people who feel, you know, they’re bought in on your vision and your mission, but have the initiative or feel that they can, right, act independently. I mean, right, like, or come up with ideas or don’t have to be supervised. You don’t have to micromanage them all the time, but that’s tricky though too, right? Because this whole control freak thing in women’s nature, you know, where we talk about our businesses as our babies, right? And that sense of loss of control of allowing somebody else to just kind of fly a little more freely than maybe we feel comfortable with. That’s tricky, I think, on some sort of deep psychological level. How did you grapple with that and what would you advise, you know, other women who are in that situation?

Allison Maslan:                 So I’ve been through that many times in the different businesses, so I’ve had ten companies and I think I had to have a couple therapy sessions going through the process of letting go-

Melinda Wittstock:         Just a couple?

Allison Maslan:                 It was tough letting go. Right now, we have a mastermind called Pinnacle Global Network where we mentor business owners around the world and I have a team of ten CEOs that have built their own very successful companies that are on my team and they help mentor these amazing business owners.

Allison Maslan:                 But in the beginning, it was just me, so to make that shift and let go was hard. No question. Why? Because I care and that’s why others are being controlling, because you care and that is a good thing. But if you can, you know, the energy about you, the energy about your brand, if your team and your company culture is emanating the energy that you carry, it’s like they’re taking that energy and they’re casting a much wider net, impacting so many more people than you could do alone. So it’s really like helping you to touch all these people with your caring hands.

Melinda Wittstock:         Right.

Allison Maslan:                 That’s the shift that I had to make and it’s exactly true and the truth is that it’s really our own ego that’s in the way to think that it has to be us because your customers want to be taken care of. They want their questions answered, they want to be supported, they want to get good results. It doesn’t have to be you.

Melinda Wittstock:         Yes. I think that’s so smart, I think any entrepreneur’s life is – that the business growth comes with each spurt of personal growth. There’s such a correlation between the two which is one of the reasons why we talk about this intersection between mindset, mojo, and money, that it really starts in your head. So with each new challenge that entrepreneurship throws at you – and they’re always going to be many, some of them are predictable, but the longer you’re at it right? But a lot come from left field, a lot come from places and things and just events that you can’t control.

The only thing you can really control, I guess, is your reaction to them. So the personal growth part is critical to success. So share with me, if you will, some times when, gosh, you know, you were challenged by something in any one of these ten businesses. My God, ten businesses. When you were challenged and what that meant in terms of sparking personal growth.

Allison Maslan:                 Oh, you know, it’s such a huge part. You’re absolutely, hundred percent correct. It really is in our own growth and I believe when we do hit these road blocks, it forces us to level up and I believe the difference between someone that’s going to successful and someone that is [inaudible 00:30:47] that more successful just gets out faster. We all get knocked down, but who’s going to get back up, right, the fastest and jump back in and let it go, right? You can’t keep carrying that pain around with you.

So, you know, it’s like in basketball, right? If they miss a basket and they’re running, trying to get the next point, they keep thinking about that basket that they missed, then they’re going to keep missing the ones moving forward. So I think the biggest thing is being able to learn from it and let go. I’ve been knocked down so many times that I can’t even tell you. I mean, there’s so many things that have happened in every single business that I’ve had and it just, you know, I don’t let it throw me anymore. I’m just so used to it.

After 35 years of being a business owner, we’ve had months where there’s zero cash flow and there’s 200,000 dollars of bill coming through, or, you know, we have a big launch and all the technology has died in the middle of it, or, you know, you have an event to fill and all of a sudden, the hotel says, oh, we’re going to give this away to XYZ corporation and your event’s in two weeks. I mean, you just … I don’t think that there’s anything that anyone could throw at me at this point that I couldn’t handle.

Melinda Wittstock:         Yeah, like I’ve had all of those. I had an embezzlement in an earlier company, which was devastating, because it rocked the whole team. Oh my God, it was horrendous. I’ve had, you know, a mobile app I was about to launch that was heavily dependent on Twitter and Twitter’s API and their Terms of Service which they changed a week before our launch. So, you know, there’s stuff like that that happens, but it’s really how you react to it and also letting go.

You know it’s interesting that you mentioned that you were in a pretty catastrophic car accident and it made me think of someone who I met at an event a couple week or so ago, a couple weeks ago, named Hal Elrod who wrote “Miracle Morning” and just a marvelous entrepreneur, but he really came up with this five minute rule that you can’t change the past, so there’s no point being upset or in any way angry or carrying any of that with you for longer than five minutes, so it’s literally … He had a catastrophic car accident aged 19 and it’s a miracle that he’s alive, but you know, when all the doctors told his parents that he was somewhat delusional, because he seemed too happy for the condition that he was in, and you know, his parents were dispatched to talk with him. And, you know, he just said to them, well, look, you know, I have this five minute rule. You know about this, right? I can’t change it, so I’m just going to let that go. I’ll let myself feel the grief, the pain, the anger, the resentment, you know, all-

Feel the grief, the pain, the anger, the resentment, all that stuff for five minutes only. So, that’s hard … Maybe hard to do for people. Five minutes seems a bit radical, but at least no longer than 24 hours.

Allison Maslan:                 Yes. Exactly. Exactly. And we do that with our team here. I said, “You guys can scream about it and cry for a minute and then, let’s figure out what the solution is.” And I think the whole idea is just to … I mean, nobody’s super human. We all have fear. We all have grief. We all have anger. And sometimes, even anger can give us strength and power, right? You don’t want to become an angry person.

So, it’s okay, I think, to feel these things, but really it’s when you get lost in it. When those things become bigger than you. So, one of the exercises I do is to tell people to visualize themselves, like the Jolly Green Giant. Like massive. Just see your energy and your ‘beingness’ as this massive being, like huge. Magnanimous. And whatever the problem is, is a tiny pea. When you think of the Princess and the Pea? This tiny, tiny little pea? And so, you’re looking down on it. Your confidence, your strength is over taking this tiny little thing.

And so when you can shift the level of the impact that it’s going to make on you energetically, then you’re not drowning in it anymore, you are overcoming it.

Melinda Wittstock:         So, so astute. And so you have this … You’ve mentioned it already, but Scale or Fail, a wonderful book coming out. Which, I think, is so important for all entrepreneurs to read, but particularly women. What made you decide you wanted to write the book?

Allison Maslan:                 So I do feel like there is this nowhere land that people really don’t talk about. You hear a lot about start ups and how to get started, but once you start making traction in your business, how do you break through that wall? And what I know to be true is that once you hit that seven figure mark, you really have to have … You have to reconstruct your company, because what worked in the early days is not going to get you to that eight or nine figures. It’s that old saying, “What got you here won’t get you there.”

And so this book really speaks to that. It’s called Scale or Fail, How to Build Your Dream Team, Explode Your Growth, and Let Your Business Soar. So, it’s my scale it method of the strategic vision, cash flow, alliance of the team, leadership, and then putting it all together in a really strong execution plan to take your business to that next level.

Melinda Wittstock:         That’s great. I mean, what are some of the predictors of success? Is there anything about someone’s personality, or their outlook, or how they go about their day; we talked a little about mind set and the attitude and letting things go. But are there any other things that are suggestive of someone whose going to be able? A CEO that’s going to be able to take a company to scale?

Allison Maslan:                 Well, I mean, you really have to have that driven component. You don’t have to be OCD and extreme Type A, ’cause I’m definitely not. So, but you have to be able to have that intention, get crystal clear on what it is you want to create, and you have to be … You have to make that decision that you’re going to reach that goal, no matter what. And you need to get the support, and of course that’s what this book is all about. Is giving you that support.

But I think that whether you’re just starting out, or you’re already in the seven figures, to me I can pretty much spot somebody that’s super ambitious and willing to do the work. And to do the hustle. So, it doesn’t mean work ten times harder, multiply your business by ten times. It also is being, learning that right next step. That right next strategy that will surpass thousands hours of work.

Melinda Wittstock:         Yes, leverage. Understanding leverage. That’s so important in terms of, just prioritizing and working smart. One of the reasons I asked the question, though, is that often the person who is the start up person, sometimes people are just meant to be start up people, right? Like they’re really great at starting things and they need an early exit. And somebody else is going to come and grow the company.

So, it’s a rare person, or is this true? Is it a rare person that can take it all the way from start to, say best case scenario, eight or nine figure exit or IPO?

Allison Maslan:                 I mean, is it more rare than not? Yes. But I think part of it, and especially for women, is that I feel a lot of women believe that it’s not possible. That we need to change the reality around that. We need to change the conversation. And when I talk to women, why not turn this into a ten million, twenty million, hundred million, five hundred million dollar company, or more? Why not? And all of a sudden, their eyes get really big like, “Oh my God. Why not?”

Melinda Wittstock:         Why not? Exactly!

Allison Maslan:                 I’m like, why not? They just haven’t thought about it. So I think it’s just we’re in this entrepreneurial explosion. When I was in my younger years, at 19, you didn’t see hardly any women running business. Especially at that age. It’s changed now.

Okay, so this is the time. This is the me too movement as well. And it’s … I think there are no limits. So, it’s … And the support is out there. The need is out there. And I think this is the time. So, it … But it is … Of course, it’s a lot of work and it also is what your goal is. You may be the person that says, “I’m going to stay as the CEO of the company and I’m going to run this company for the length of my lifetime. Until I pass it on to my family.” Or your goal might be, that I have [inaudible 00:40:46]. Or maybe that you want to keep it as a revenue stream and bring on another CEO and you step out. But you keep the company.

So it really depends on what your end goal is. And once you know that, then you can work backwards.

Melinda Wittstock:         Was it always clear to you where you were going and what your mission was?

Allison Maslan:                 No. No.

Melinda Wittstock:         It’s all right and it changes over time, too.

Allison Maslan:                 It does. And that’s when I talk about those five phases. That’s really in phase three, you start to get a clear vision on your company. In the beginning you just need to get it up and going. But, you don’t know how the customers are going to respond. You don’t really … You may completely change your revenue stream.

I mean, you look at Play Doh used to be a wallpaper cleaner. And then kids were playing with it. So, it was like, “Let’s make it into a toy!”

Melinda Wittstock:         Oh my goodness, that’s so funny. I think of a company like Twitter, which ironically started out as a Podcasting platform, and they were too early. Nobody was into Podcasting. And that was the first iteration of Twitter. It took them like eight business models before they became the Twitter we know now. So, this is actually true of most companies. That kind of being able to pivot.

So when are you pivoting meaningfully and when are you pivoting because you’re chasing a shiny new object? It can be tricky sometimes.

Allison Maslan:                 Right. Yeah, that is so true. It really is a different … And have the courage to say, “You know what? This isn’t working.” Right? And, again, drop the ego and really listen to the marketplace and what they’re wanting. And ask yourself, is that something that you want to do? Because you’re going to be spending a heck of a lot of time and energy doing that. But I do believe the vision will become clear once you had some mileage out into the marketplace. And then really seeing the direction you want to go.

Now I have, the company I’m running now, we’re going into our 10th year. So, I have a real clear vision on where we’re going. But, every quarter, new doors open up that I haven’t thought of before. And new opportunities that are so exciting, that … But if you have the vision where you want to go, don’t worry about the how.

Just keep walking forward. Get out there. Connect with as many people as you can. Give, give, give. Come from a place of generosity. I mean, I cannot talk enough about that. And the doors will begin to open.

And then, like you said Melinda, you’ve got to make a decision. Is this a shiny object or is this a great opportunity. And if it is, and if it feels right, and if it is where the big picture vision of where your companies headed, then you got to jump on it.

Melinda Wittstock:         Absolutely. And knowing when to persevere and when to walk away. That’s a tricky one, right? If a business isn’t really working. Is it –

Allison Maslan:                 Yeah.

Melinda Wittstock:         … And knowing. ‘Cause so many companies almost fail. I think of the story of Evernote, which is always interesting to me. I mean, he’s out of money, it’s three o’clock in the morning, he’s going to tell his whole staff that Evernote’s dead and he’s closing it down, when he gets a call from a customer at three o’clock in the morning. Like from Sweden or somewhere. Saying, “Hey, I just want to say how amazing your product is. It’s really great.”

And then the guy says that … The guy from Sweden says, “By the way, are you looking for investors?”

Allison Maslan:                 Yeah. Okay, that’s the angels. Those are the angels speaking. The wings, as you talk about. Absolutely.

You know, I really think it … You know, here’s the thing. Sometimes what happens is you beat your head against the wall so much, you’ve lost your passion. And I think when people are ready to walk away, they just … They don’t have anything left. The spirits just not there and they need to wrap it up.

I think, though, if there is a will, there is a way. If the passion is there, you can find a way to make it work. There is always a way. And it may be there is a pivot. I, personally, feel for myself, know that if I’m going to run it, a company, I’m going to make it successful just because I decide it’s going to be.

Is it going to be easy? You know, like you said early on, it looks like from the outside that it is. That’s not the case. But, you know, that’s what I think keeps people excited, entrepreneurs, is the challenge. We like the challenge. The adrenaline from it. And you stick with anything long enough, whatever it is you do. If you’re an artist, a singer, a performer, writer, or you’re an entrepreneur. You give it enough juice, you stay with it, you don’t listen to negativity, you keep your head moving towards that goal, and you walk towards it every single day. It’s absolutely going to come to fruition.

Melinda Wittstock:         Beautifully said. And so I know that you have a wonderful gift. Speaking of scaling, you have a wonderful gift for our listeners today. Can you tell us about it?

Allison Maslan:                 Yes. It is my scale formula, which is a five video training with these great downloads that really takes you through the scale formula. The vision, the team, being a leader, and executing this road map. And to get it, all you got to do is go to allisonmaslan.com/CEO.

Melinda Wittstock:         Wonderful. And we’ll make sure that that’s in the show notes and thank you. That’s a generous offer ’cause I know the value of that. Of this knowledge and just knowing it early enough. So I encourage everybody to take Allison up on that wonderful offer.

Allison Maslan:                 I wish I had it years ago.

Melinda Wittstock:         Oh God, me too. It would have saved me … Where were you anyway? It would have saved me a lot of time.

Allison Maslan:                 Me too. Oh my goodness.

Melinda Wittstock:         I’m sure. Yes. And you look back and you think, “Oh God. If I knew then what I know now,” that kind of thing, right? But again, it’s all part of that experience. And I wouldn’t personally take it back for anything. ‘Cause all the tough things, the adversity things, are the things that actually make you unique and wonderful in many ways, as well.

Allison Maslan:                 Oh yes. Absolutely. I wouldn’t change a thing. Of course, hindsight is 20/20. When you’re in it, you might be thinking differently.

Melinda Wittstock:         Yes.

Allison Maslan:                 Right? But when you look back, and you see the whole just infinite design of how all the pieces fall together when you think something is the worst and it ends up being the absolute best. Something so far beyond your own imagination. It just comes together perfectly.

Melinda Wittstock:         Exactly. Well Allison, I just want to thank you so much for taking the time. Putting on your wings and taking flight with us today.

Allison Maslan:                 It’s just been so much fun. Thank you so much for having me.

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