In today’s episode of The Startup Chat, Steli and Hiten talk about whether being an entrepreneur really the right way to gain more freedom in life.

It’s common for some people to think that being an entrepreneur is the right way to gain more freedom in life. However, this is not often the case, as sometimes, entrepreneurship can rob you of as many freedoms as it gives to you.

In this episode, Steli and Hiten address this belief by many that entrepreneurship grants you all freedoms in life, they stress the importance of defining what freedom means to you and much more.

Time Stamped Show Notes:

00:34 About today’s topic.

01:38 Isn’t freedom the main motivator for people becoming an entrepreneur?

02:09 Why you should do what whatever you need to do.

03:06 Why other people telling you what to do is easy.

03:53 How there’s a value in being told what to do.

05:31 Why you’re gonna need to have to work with people to be successful at something.

06:16 How entrepreneurship can rob you of many freedoms.

07:20 How you can design a life of freedom.

07:53 Why it’s important to define what freedom means to you.

08:22 How you can have a boss and still not feel like you’re being told what to do.

08:48 The biggest problem with the word “freedom”.

3 Key Points:

  • If you want the freedom to do whatever you want, then go on and do it.
  • Other people telling you what to do is easy.
  • The way everyone defines freedom might not be the same.


Steli Efti: Alright everybody, this is Steli Efti.



Hiten Shah: And, this is Hiten Shah.



Steli Efti: And in today’s episode of The Startup Chat, I accomplished one of my favorite things to accomplish when I talk to Hiten, which is when I suggest a topic, and his reaction is, “oh God” or some version of that. That is usually, that means we are on to something interesting here. So, here’s what I want to talk to you about today, Hiten, to share this with the listeners. Which is, somebody recently asked me, two days ago to be precise, is being an entrepreneur and is running a start up really the right way to gain more freedom in life?



Hiten Shah: No



Steli Efti: Nice, alright so, this is it from us for this episode of The Startup Chat.



Hiten Shah: Yeah, we’re done. No.



Steli Efti: No [crosstalk]



Hiten Shah: You want special, go away, go do something else. Please do something else, do yourself a favor. Right now, don’t do this, stop.



Steli Efti: Alright, so, let me challenge you now. I will play the devil’s advocate, you know I really agree with you, but just for the fun of it. Aren’t most people or aren’t many people becoming entrepreneurs because they want to be their own boss, they want to have more freedom and do whatever they want, they want to achieve financial freedom and get so wealthy that they can do anything they want in life. Isn’t freedom the main motivator why people become entrepreneurs?



Hiten Shah: If you want freedom to do one thing, one specific thing, yes you should become a founder, entrepreneur, start your own business. That one thing is simple, if you want freedom to do whatever you want, whatever you want, you should do that, yes. Whatever you want doesn’t mean go on vacation. Whatever you want doesn’t mean go traveling, but it is whatever you want with your professional life, whatever you want. Meaning, whatever decisions you want, buck stops at you. Nobody is going to really give you any guidance, tell you what to do, sometimes even your co-founders. Yeah. That freedom of space to do what you want, that freedom of not relying on anyone to tell you or hand you responsibility or any of that and you having to figure all that out yourself and wanting that, I do believe, Steli, that one freedom you get. I don’t believe you get any other freedom.



Steli Efti: But, Hiten, another thing I hear a lot is people saying some version of “the reason I became an entrepreneur is because I can’t have a boss. I just can’t have anybody telling me what to.”



Hiten Shah: Well I mean, first I will say welcome to the club. Many of us think that other people, we don’t like when other people tell us what to do. But the thing is, that means what you’re telling me is you don’t want the easy life. Other people telling you what to do is easy, it’s a good thing. And trust me no one has really told me what to do in my life. I’ll tell you the truth. My father never did, thank goodness or maybe not. I am the product of not being told what to do by anybody. I think that’s rare and I don’t wish it upon anybody. And, the reason for that is you don’t really have a structure or framework or any concept of how do I decide what to do then? Cause you weren’t taught. What I am trying to say, there is a value in not having a boss and not being told what to do. That being said, I think people think about this the wrong way. Right, I think what you need to think about is work and business and your professional life. It’s not that anyone is telling you what to do. It’s that you are trying to figure out for yourself what can I do to improve the situation that I’m in and improve the situation my company’s in. So if someone’s telling you what to do and you’re being managed by somebody, it is generally because they think you can help the company and they want to tell you how to help the company. There is varying degrees of management there. From micro-management all the way to hey this is the goal, go do whatever you want or even you set your own goals which is even crazier. I would say, I think the way people think about this, they’ve either had terrible bosses or they’ve had an upbringing, like mine, which I’ve heard is rare, where no one has told you what to do so you don’t know how to deal with it. I don’t know how to deal with it. If someone tells me what to do, I have hard time with it unless I already believe in doing it, to be honest.



Steli Efti: Yeah, I think that some of this applies in the sense, that people that are rule breakers, people that don’t just want to conform and do what has been done before them and don’t just want to fit in. A lot of times, that’s not the only thing, but these type of people might be more suited to be entrepreneurs. To start their own things and vent and create new solutions and build new businesses and organizations and all that. But if the sole goal is to not have anybody tell you anything, maybe being an entrepreneur is gonna be useful, but you know, if you want to have success at a certain level of scale you’re always going to have to work with people and you’re gonna have customers that are gonna be telling you what to do and you’re gonna have investors telling you what to do and you’re gonna have advisors and you’re gonna have employees that are going be pushing you and telling you what to do. They might be your strict bosses in the sense that they can just demand you do something, or else. But it doesn’t mean that you can just do whatever you want every day. At the least you’re gonna have customers. Even if you are a single entrepreneur with no employees, no teammates, no advisors, no investors, hopefully, you’ll have customers. These customers are gonna be demanding things of you. You can’t just make money doing whatever you want, usually, you’re gonna have to be of service to others. And, the freedom thing is funny because the way I think about entrepreneurship, it can provide you certain freedoms and it can also rob you of many. Even a simple thing to stop thinking about work once you leave work. The freedom to take a vacation and not be on at least in your mind. The freedom of certain things you’re not gonna have those. The way that I think about this more is, the better vehicle to think about what entrepreneurship can give you is, it is going to give you a lot more responsibility. It might give you a lot bigger chance for impact and for growth. But freedom, maybe, depends on how you design the whole experience for you and what your priorities are. But, not necessarily. It is not like every entrepreneur by default is “more free” than people that are in employment. We could open a can of worms of what even freedom means. How do we define freedom in the grander scheme of things.



Hiten Shah: You know, yeah when you think about it like that, you could design a life of freedom, for sure. You could design a life where you are like, look I’m gonna get some revenue goal or something for myself and then I am gonna travel the world for some amount of time. Or you could say, again if you are that smart, I’m not this smart, but you’re gonna create a company and in x, y, z amount of years you’re gonna retire because you are gonna to sell it or make enough money that you can quit. Then you have freedom. I think for me this question has a lot to do with, as I think about this, if someone asked me this or told me this statement, I would start by first saying “hey, tell me how you define freedom?” Let’s make sure we’re talking about the same thing here because the way I define freedom and you define freedom, Steli, might not be the same. The way everyone that’s hearing this defines freedom might not be exactly the same. Cause to me, how I was raised, freedom is what I have right now. No one is telling me what to do, but if I had a boss, I still wouldn’t necessarily think they’re telling me what to do. You can have a boss and still not feel like you’re being told what to do. I think a lot of it is a matter of what do you consider freedom. Some people that I know, for them freedom is literally, I don’t need to work. Period, for money. I think one of the biggest issues with this word and many other words and many other things in startup land and why people think they should be entrepreneurs or shouldn’t has a lot to do with, it is a personal choice. This is one of those personal choices and I think that you need to make it personally based upon what you are looking for. For me, like I said, I have freedom to be creative, I have freedom to make decisions. I also have more responsibility than I knew I was getting into many years ago. And that, actually, is not freedom in some people’s eyes because they don’t want responsibility.



Steli Efti: Yeah because freedom feels like something like light and responsibility to many people might feel like something really heavy. I’m like shit I wanted to be lighter on my feet and dance just dance around life and now I have this huge bag of stones that I am carrying around. I’m responsible for so many things and it just weighs on me, on my shoulders and this doesn’t feel like freedom and fun and doing whatever you want. I think that’s where that question came from. The context was really just somebody that thought entrepreneurship would give them a lot more freedom and now one year into having quit their job and having hired some people and having tried to launch something, things haven’t worked out. The experience hasn’t been as much adventure and fun and has been a lot more pressure and stress and failure. The person’s in this life crisis of reflecting on, is this really, did I do the right thing? Was entrepreneurship the right way or am I just too dumb to make this work? Is being an entrepreneur really the right way to become, to have more freedom in life, to do more of the things that I want because that hasn’t worked out yet. I think that was the moment in time capture that made this person reach out to me and ask that question.



Hiten Shah: Yup, I think that a really key thing to think about and I think, defining freedom for yourself, if I were to give a tip on this one would be really think through what freedom means to you. Again, just like with many things you deal with on a daily basis or you deal with in your life, it came from place that you might not be conscious to. It took me a long time to be like, oh crap, I was given a lot of freedom growing up and that’s how my definition of that word, that’s where it comes from. That’s how I was sort of trained to think about what freedom means to me.



Steli Efti: Love it. Alright, this is it from us for this episode. As always if you join it and you want to spread the love and give a little bit back, do us a favor, go to iTunes or wherever you listen to us and give us all the stars in the world that are available and a little review, highly appreciate it.



Hiten Shah: See ya.



Steli Efti: Buh-bye.