As serial entrepreneur Marty Park puts it, he was initially playing business when he suddenly found that his first entrepreneurial endeavor was taking off. In his new book, Tiger by The Tail: 99 Secrets to Tame and Master Your Business, Marty addresses that feeling entrepreneurs can experience when their businesses start to take off. It’s almost as if they have the tiger by the tail and don’t know if they’re going to get bitten, die, or hold the beast at bay. That’s how the stress and pressure can feel.

Marty speaks to entrepreneurs who have made it through the startup phase only to find that there are more challenges lying in wait. He shares the secrets, tools, and ideas of entrepreneurial tiger tamers.

Nikki Van Noy: So, Marty, talk to me a little bit about your experience being a 25-year-old, which probably doesn’t look like everyone’s experience being 25.

Marty Park: Yeah, 25. I had a lot more pressure and responsibility than most people. I think there’s a lot of that, you graduate from college and you think, “Well now, I have got to go get a job.” But at that point, I’ve been in business for four years. I’d really been playing business for a year and then my business partner Greg and I had to go to his dad and ask for a second mortgage to be put on the home.

You can imagine a second mortgage really ups the stakes pretty fast. So, over the next few years, with some guidance from our parents, our fathers, and some other guys who had become business mentors, by 25, I think we had a dozen staff, we had our first software company going, and we were just launching a second one. So, the pressures of payroll, rents, and just all the moving pieces of the business really were dynamic and stressful.

People worried about where they were going to go drinking on a Friday night. I had so many other things to wrap up and that filled my mind. As a 25-year-old, you have that energy, but I certainly had a lot more on my plate than a lot of people at that age.

Playing Business

Nikki Van Noy: Talk to me a little bit about playing business. I’m intrigued by that phrase.

Marty Park: This is fantastic. So, Greg and I started the company when we were 21 and our impression was–what do you do first? You go get office space. What do you do next? You hire a receptionist, and the criteria we had as 21-year-old boys for what a receptionist needed to be is vastly different than my perception today.

We used to head to an office space that was so large, I remember Greg would push intercom on the phone and it would take me 50 yards to get to his office and 50 yards back. There were only three of us in the office, to begin with. And so, we really were constantly updating our marketing materials and brainstorming.

One day, we were sitting around with Fast Car Magazines talking about whether it would be a Ferrari or a Porsche, and we hadn’t sold anything. We were actually transacting nothing, we were not doing business, we were simply playing business. Our bank account became the realization of what we were doing wrong.

Nikki Van Noy: That’s hilarious and sounds very accurate for what it would be like to be a 21-year-old in business. What was that business, out of curiosity?

Marty Park: We built interactive voice response systems. So, it’s the technology used in voice mail or in a telephony system, where you’re pressing one, two, and three to get to your choices. We were building that system. In fact, we started with voice mail and then realized, there were some significant telecom players who were in that space, and so one of the ways that we were fortunate was pivoting to really focus on niche programs. And this goes back a few years to the yellow pages.

They had a lot of options too. You could dial a law system, or you could dial into a health system, and so we started to specialize in those data systems for individual industries, and that’s what really made us successful.

Sounds Like Fun!

Nikki Van Noy: Throughout your career, you’ve worked in such a diverse number of fields. How has that been possible for you? I feel like a lot of us think of business as being a more limited thing, where we kind of stay in our lane.

Marty Park: I would say, there’s a couple of aspects to that. One of them is starting so young. I use the phrase blissful ignorance. I really didn’t know a lot. In fact, there’s a piece in the book where I talk about my friend Dom, who I reference fairly regularly. Dom was talking about how he chose industries and how I had, and my approach really had been that people would ask me, “Hey, you want to get into this?” And I went, “That sounds like fun, let’s do it.”

I looked and thought, “Would this be challenging?” But I never really spent a lot of time thinking, “Am I qualified to be doing that?”

I had gotten into a number of industries and by the time I really started to feel the confidence as an entrepreneur or as a business owner and felt like I could get in to just about anything, that probably took close to a decade.

Nikki Van Noy: That really strikes me as not stopping to think, “Am I qualified to do that?” How amazing it would be if we all had that mindset and kind of carried it through. That we just followed where we want it to go without stopping to ask that question. Obviously, it could get you in trouble in some ways too, but I think there’s so much freedom for discovery and joy in there.

Marty Park: There really was. I had so much enjoyment. I was very fortunate to be involved in industries that really, for a guy in his 20s when I started out, were fun. And this technology side was very challenging. I’ll give you an example. A good friend of mine who was really expecting to be a lifetime bartender one day said, “I want to open a music club and a bar and business,” because I had been in it for a while by then, and we were in our late 20s.

He said, “Would you help me set it up?” And I thought I negotiated the best deal ever. I said, “I will take 5% equity and free beer for the life of this club.” To this day, I still think that’s my best negotiation. What happened was other business partners that he had taken on, who were other bartenders, slowly started to fall off. I said to them, “Listen. When it’s a cash call and we need to put more money in, you can’t be trying to sell a car.”

Six weeks later, a guy was trying to sell an RV and I said, “Hey Mike. I thought we talked about this.” He said, “Well you said car, this is an RV.” I slowly started picking up equity, and the day we opened, I owned 50% of a bar and music club, with no knowledge of the industry. I’d had some bartending experience but knew enough from my other businesses to know revenues needed to exceed expenses.

There was a little bit of luck, we opened strong, and there was an opening in the market that we recognized. But certainly, it was really lean when we opened up. I think it drove a lot of innovation because we did not have a lot of capital.

But what a great experience, I mean, in terms of fun. Those are the kinds of businesses that we really just love putting in the hours. The community we had with the musicians, and that crowd, and so many customers became great friends. Some of those kinds of lessons have actually really carried me through in all sorts of businesses and with clients. I’ve referenced some of that stuff, like building community and how you go about doing that, in the book.

Tiger by the Tail

Nikki Van Noy: I love that. This experience you’re talking about reminds me of this metaphor that you’re using throughout your book, which is having a tiger by the tail. When your business starts to take off, that’s what it can feel like sometimes. Talk to me a little bit about why that’s how you see it and also, what that experience feels like when you’re in it.

Marty Park: Yeah, absolutely. If you look at how business is supported, there’s so much when you start out in business as a startup, whether it’s technology or any kind of startup. Often times, there are programs, there are funding programs, government support, lots of websites and online stuff that you can use that focuses on startup.

Now, what I discovered is, beyond this startup, when you have reached stability, where you have some customers, and you’ve got a physical space, brick and mortar, and maybe you got a couple of employees. As you get to that place of stability, the resources drop off.

If you think about somebody who starts a business, often times they’ve gotten their business cards, they know what they’re going to sell. They figure out how they’re going to price it. Well, that’s pretty easy, but things certainly get complicated the second you start to get clients, have to transact, and you take on an employee. And all of a sudden you realize, “What about time sheets? What about payroll? What about contracts? My god, we just got a client, how do we invoice? Wait, accounting.”

You can see the snowball effect of all of the moving pieces of a business and it really starts to become a lot more daunting than I think a lot of people realize. The phrase tiger by the tail came to me when I was sitting with a gentleman who owned a business. If you can imagine, he leaned in across the table and it was just the both of us. He leaned and like he was going to whisper. He had been pretty confident and almost a little bit aloof or casual about the meeting.

Something I had said, obviously, hit a nerve with him. He leaned in and said, “You know, I never expected it to get this big. I mean, I just went out on my own and now I have got 22 employees. I mean, it’s overwhelming, I don’t know what I’m doing, they think I know how to lead, and I don’t. I don’t have all the answers and I’m telling you, man, every day, I feel like I’ve got a tiger by the tail.”

That phrase and that experience of hearing the stress in his voice, and seeing the concern of, I think a little bit feeling like a fraud, really led me as I was working on the book to say, “That’s the feeling.” It is that sense of chaos–of fumbling around a little bit. You know that there are some big stakes involved. Lots of entrepreneurs have their house on the line when it comes to running a business.

Yeah, it really felt like having a tiger by the tail sort of summed up the day-to-day emotion and feeling a lot of days.

Business Growth=Personal Growth

Nikki Van Noy: When you look back at the moments where you’ve perhaps had that feeling, what, in retrospect, are some of the advantages of being in that position?

Marty Park: I think that when you’re in those moments of really feeling like you’re in over your head, or there are so many things you don’t know, I think one of the things that entrepreneurship and business ownership forces you to do, it’s not like you can turn around and say, “I’m just not coming in tomorrow.”

You have to be able to go back in and say, “Okay, I’ve got a face this, I’ve got to face it for my customers, for my staff, I’ve got to face it for my family.” It forces personal growth–it forces you to think innovatively. It forces you to persist, and I think those are all traits that can help you, not only in your business, they help you as a human being, as an individual.

So, I love the idea that entrepreneurship not only might help you create a great business, but I think it can help you become a great business owner and improves your skills dramatically, better than any other opportunity that might come along career wise.

Nikki Van Noy: In your own life, you’ve grown up in business. I’m curious about the correlation that you make between business growth and personal growth. How do you see those two dovetailing?

Marty Park: Well, it’s interesting. A business is very much a reflection of the owner. You know, when you get to be a larger corporation, a business extends beyond a president. Although very often, if you get a great corporate leader, people talk about the business culture, what’s important and its focus, and everything starts to mirror that CEO. It is very, very true when you are dealing with a small to medium-sized business that the business is a reflection of the owner.

I will give you an example if your natural tendency was procrastination–you will find that deliveries are always late. Bills are always slow being paid, and there is a lot of delay and procrastination in the business operations as well. I’ve just found that there is such a great opportunity as the business owner is forced to grow and look at their own personal habits. They can change the way they work, change the way they communicate, and learn new skills like maybe how to sell or how to market, that as they grow, the business starts to grow.

Anybody who thinks, “Well, the business is just going to grow, but I don’t have to do anything.” I always say that there is such a direct correlation between the opportunity for you to grow as an individual and it is absolutely going to be reflected in the growth of a business.

Biggest Lesson

Nikki Van Noy: How do you feel like you’ve grown the most personally through being a business owner over the years?

Marty Park: Wow, I mean I could make a list of so many different skills. When I started out, the first thing I learned about–recognizing that going from playing business to doing business–the first thing you need to do is actually convince somebody to buy your product or service. I went from being really unsure. I mean, I am a fairly confident person, but in that sales situation, for years, I was convinced they were just going to turn around and say, “Get out of my office.” Or, “I have seen through you and we are not buying this product.”

So, developing sales skills, developing a confidence in that space and then starting to hire people. Recognizing, almost like being a personal relationship, “Where are my communication skills good and where are they not very good?” And then starting to say, “How comfortable am I with promotion?” Or, “I have a chance to get in front of a group, how comfortable am I public speaking?”

Then being able to get into, “I really don’t like finances, but I really have to dive into learning about accounting and numbers.” I touch on this in the book that I, as a general rule, hated accounting. I took it repeatedly at college. Finally, when it was my own money, it got interesting to me, but I had to learn all about finance. There are just so many aspects.

Then you get into marketing, and now you go from learning traditional marketing to digital marketing, and now to social media. I haven’t even talked about what the product or service might be and all the innovations that come with that. I feel like there is such a progression of the ways it can improve you.

Some of it, that is maybe the most impacting thing, is the comfort zone it creates, that you have tackled so many different things that other areas of your life seem much more manageable. You just start to develop that confidence of, “Well, I know I could tackle this. I know I could tackle that. Because compared to what I dealt with last year in business, these seem really easy.”

Nikki Van Noy: That makes sense. So now that you have reached the point of being a serial entrepreneur, do you still find yourself in these situations where you can be in a tiger by the tail sort of scenario? Or does that not happen to you anymore with all of these backgrounds behind you?

Marty Park: Well, I would love to say that never happens, but I think that would be misleading. Do you know where it happens? I give this story of a young guy. I had spoken at a conference and he came up to me and asked about cash flow. He said, “When do you stop lying awake at night thinking about cash flow?” And I said, “Well, what time do you wake up, usually about 2 AM?” And he said, “Yeah, how do you know that?” And I said, “Oh, that is sort of the entrepreneur’s alarm clock.”

I said, “Your cortisol level spikes, you are wide awake. You are thinking about cash flow.” But I said, “The progression becomes how much you’re thinking about. How much are you worrying about now?” He said, “Well, about $500.”

I said, “Well, the next progression would be you don’t get out of bed or it doesn’t wake you up until it is $5,000, and then eventually you would be comfortable at that level, and then at $50,000 it is keeping you awake. It just keeps going like that.”

I certainly have the same anxieties looking at other companies I might buy or going to a bank and thinking, “Okay, well, this is a much bigger number for this loan now.” So, it is still the same, maybe that balance of the same nerves and concern and fear. But offsetting that now is the experience and the confidence of, “Hey, I have done this before. I can do it again and I know a lot strategically and tactically. So, I’ve got a lot more tools to be able to make the next business a success.”

Mindset and Persistence

Nikki Van Noy: All right, let’s say we have a listener who really is resonating with what you are talking about right now and realizes that they’re in this situation. What’s the first thing that they can do pretty immediately to start to feel like they’re maybe not necessarily bringing that tiger under control, but at least getting a teeney-tiny step closer to it?

Marty Park: Well, the way I open the book is talking about mindset. People have said, “Well, why don’t you dive into some of the tactics of a business first?” But to me, when you get control of how you’re thinking about the business, it really starts to dictate and change what happens in the business. The results of the business really begin in a business owner’s mind. Some of the things I talk about is I try to get the message across to people that while you may not feel like it today, you absolutely have the skills and ability to do this. That really my message of, “Yes, you can,” I hope resonates with people because just believing that is a huge thing.

I think one of the best skills as an entrepreneur is persistence. Being able to persist, adapt, and innovate a little bit and then continue to persist. If somebody says, “Well, it is going okay,” my number one message would be to just keep going. Start to add some of these ideas and just keep working at it.

I think people give up too quickly on what could be a really, really successful business because they have been misled that in the first year it is just going to take off. Really, the cycle for a lot of entrepreneurs can be up to seven years before the business really explodes. It’s like that rock band that tours in a van for 15 years, and then they become an overnight sensation. People don’t appreciate the 15 years of lead up. I think a lot of business owners are like that.

One of the things I love is talking to people about that there is an abundance of business–more than ever before–for every small business, whether it is online international markets, being able to reach more people right to their handheld smart phone. There are so many great things about today being the time for entrepreneurship. I like to point those out to people because if they are struggling, it brings them back to recognize, “Oh, yeah there is opportunity, and I just need to focus on that abundance, that opportunity.” That focus certainly makes business day-to-day way more fun.

Nikki Van Noy: When you look back at your career thus far, what are you most proud of retrospectively where you realized that you were out of your depth but resolved it and came out ahead?

Marty Park: I had a moment where I built out a restaurant, without knowing anything about the construction process. I had run a restaurant, but again, never built one or designing one. I remember one of those moments just before we opened when everything was set up, the furniture, everything was absolutely complete, all the decorating plates were ready to go in the window of the kitchen.

I had a quiet opportunity to open a bottle of wine and just sit and appreciate what had been built. I think I’ve had a lot of those moments and I think a lot of business owners recognizes that sometimes if you’re in your shop or your store, and sometimes it is at the end of the week on a Friday night and being able to flip off the lights and appreciate that, “Hey, look what I have built and we had great sales, or look at all the customers we’ve served.”

To me that is one of the most rewarding parts, those little moments where you just stop to say, “Look at what I’ve built, look at what I’ve created from nothing, look at the people I’ve served.” Those are still the things that drive me forward. The next business I want to look and say, “Well, who is the audience going to be? How are we helping those people? What are we doing?”

I think for the book, my motivation was that if there was an established entrepreneur, somebody already running a business, and having a bit of struggle, that they could read this and say, “Not only did I get some ideas, but I am re-inspired. I feel a little bit empowered and I’ve got some new tools that I can bring to work tomorrow, and ideally make it more fun and more successful.”

Nikki Van Noy: That’s such a great reminder, especially in the entrepreneurial world. I feel like we can get so focused on driving to the next thing that we forget to stop and take that moment to recognize what we’ve built.

Marty Park: Absolutely. And I will say, it sounds really smart as I talk about it today, but that lesson took me a decade to figure out and learn.

Beyond the Startup

Nikki Van Noy: Okay Marty, is there anything I haven’t asked you that you want to be sure to get in here?

Marty Park: I don’t know, I think we’ve covered a fair amount. One of the things I stress is that I really want people to buy the book. Because there’s only so much you can dive into in a book in each of the areas that I’ve set it up. There are all sorts of tools we’re going to have available on the website and we want you to use those tools and move your business forward.

There’s nothing worse than something that gives you the idea but doesn’t give you the how-to. With the book, we really try to make sure that we give the idea in a clear simple way. Then we say to people, please, go to the website, there’s a template that you can use, there’s a tool there, there’s a sample. So that people really have the ability to apply it.

I want people doing it and taking action, not just finishing the book and going back to their struggle.

Nikki Van Noy: What is that website, Marty?

Marty Park: It’s