[INTRODUCTION]

[0:00:04.5] ANNOUNCER: Welcome to Branch Out, a connection builder’s podcast, helping middle market professionals connect, grow and excel in their careers. Through a series of conversations with leading professionals, we share stories and insights to take your career to the next level. A successful career begins with meaningful connections.

[0:00:20.8] AD: Hey everyone, welcome to the Branch Out podcast, I’m your host, Alex Drost. Today, we welcome Isatou Smith. Managing Director of EisnerAmper Government Services. Isatou is natural entrepreneur who left a stable corporate role to gain a greater level of autonomy and agency in her personal and professional life. 

During our conversation today, Isatou and I discuss our experience as entrepreneurs, the mindsets that have helped us succeed and the growth we have experienced along the way. I hope you all enjoy.

[0:00:55.4] ANNOUNCER: Connect and grow your network. We are on LinkedIn, search for Connection Builders.

[INTERVIEW]

[0:01:02.7] AD: Isatou, welcome to the Branch Out podcast. 

[0:01:06.2] IS: I’m excited to have you here today, thank you for having me.

[0:01:09.0] AD: So why don’t we start out with just sharing a little about who you are, your background and then after that, let’s dive into a conversation about entrepreneurship.

[0:01:17.3] IS: Sure, absolutely. So I am currently the managing director and cofounder at EisnerAmper Government Services Ltd. here in Grand Cayman. I have been in the financial services industry for approximately 20 years now. I started my career out at the regulator here in Grand Cayman in investment funds, so I’ve always been in financial services. I did that for several years and then decided, “Okay, let’s try something different” and I went to large law firm here in Grand Cayman doing directorships and a lot of work, again, for investment funds.

I did that for several years and I started to think, “You know what? Maybe there’s more to life and this and let me try it out.” So at that point, halfway through my career, I decided let’s try the entrepreneurial route. Let’s try doing exactly what you're doing now for a large law firm but let’s try doing it for yourself and see how that works.

So I did that and I did that for several years, it was going really well and then I got approached by EisnerAmper, to where I am now to say, “Hey, look, we see you out there, we like what you’re doing, do you want to partner with us?” and that all stated in 2018, 2019, we got up and licensed and here we are in 2022, several years in and doing really well with the company.

[0:02:30.2] AD: What I really love about your story is, and we’ll dive more into some of your journey in that, but it’s the entrepreneurial drive. You’ve had a journey of doing the work you’re doing in under a couple of different structures,  and a couple of different environments, and it sounds like you have a real entrepreneurial passion and tenacity for that. 

I’m excited to dig into some of the lessons learned about that but just, let’s give a little bit of context for our guest. Can you share specifically, high level, what do you do today in the work that you do specifically?

[0:03:02.3] IS: Right. So as I said, all of my career I’ve been working in investment funds and so I work with investment funds and investment fund managers. So we help them with their regulatory status here in Cayman, we provide ancillary support services. So we do anti-money laundering, compliance, know your client procedures, all the fun stuff that clients don’t really want to do but they have to do, so we take care of all that for them.

We act as independent directors under boards of their funds, just to add that extra level of protection for investors. So we do quite a bit of support for investment funds that are based here in Cayman but the investment managers are based anywhere around the world.

[0:03:38.3] AD: Because I know, a lot of people are thinking this back in my mind and why Cayman. Why are there so many investment funds in the Cayman Islands? Let’s demystify that for a little bit.

[0:03:46.1] IS: I’d like to say it’s because of me but unfortunately, it was a long way before I was around. So Cayman is the number one jurisdiction for offshore funds. We have several thousand I think at last count, it was over 12,000 offshore funds.

We are a tax neutral jurisdiction. A lot of people misconstrue that with tax evasion but we don’t have taxes. We have indirect taxes, they’re not going to be employment taxes or any other taxes on your income here. So I think that is one of the attractive features of having your funds here.

We have great infrastructure, we have very, very good service providers here as well. So we have your accountants, we have your attorneys, we have people like myself that provide consultancy services, compliance services.

So I think when you’re looking at around all your jurisdictions, we tick all the boxes and our laws are quite flexible but they’re also set-up in such a way that it gives investors that added protection. So those are some of the main features of I think, draws people to the Cayman Islands and you will get the question from an investor’s perspective. So why not Cayman? That’s just how significant our jurisdiction is in the investment funds world.

[0:04:54.3] AD: It’s certainly the way the investment world works, if you will.

[0:04:56.7] IS: Correct.

[0:04:57.5] AD: Right? So and your – specifically, the work you’re doing is in and around compliance administrative support, is that kind of a broader way to say it?

[0:05:05.9] IS: Some of it, some of it. So you have your investment managers that they come up with the strategy, they come up with investment objective and they start a fund. You're going to often have millions, hopefully billions of dollars under management and most times, these institutional investors want someone on the board overseeing their money.

Just seeing what these various service providers are doing, so that they have an extra pair of eyes that’s independent from the manager themselves that’s actually conducting the management of funds. So that’s what we do, we come on board, we act as an independent director, we bring the expertise and value from the perspective of Cayman, knowing the jurisdiction, knowing the laws. 

But then also having worked with other funds, we can show, you know, what’s best practice, what have other funds done? And just bring that added value. So we can act as independent directors or on the other side of it, we can also assist with tax filings. Like we have tax filings here in Cayman for the department of international task corporation here. They facilitate filings with the IRS and other agencies around the world.

So we can assist with those filings and then we also do the compliance part of it. So lately, compliance has been a massive, massive, massive feast where people need that additional work. You’re not always going to have the resources in-house so we can do that outsourcing to our clients, where we conduct familiar client procedures. 

We conduct the sanction screening, obviously with the big piece with Rasher recently, that’s, you know, a very topical point but we can take all of that in for the clients themselves and do it for them.

[0:06:33.5] AD: That makes a lot of sense there. Now let me ask this: How did you get into it? How like, did you start there, and how did you stumble to doing the work you are now and that I think will lead us into our entrepreneurial conversation?

[0:06:46.5] IS: I feel like I sort of fell into it actually, I did not start wanting to be in financial services. I actually thought that it was not intriguing enough in the beginning. I wanted to be in marketing but coming back out of college and university, I just said, “Look, I need a job” I applied to various jobs and this was the first one that said, “Look, you have the expertise, you have a degree in business, you have, you know, the background, we want you.”

Three weeks in, this is at the regulator here at Cayman, three weeks in, I got an offer for marketing, which I thought I was going to work for the Department of Tourism and I was going to be an ambassador for the country and all these fun stuff and that I thought, “You know what? Financial services isn’t that bad, let me just stick it out.”

And so I stuck it out for four years at the regulator and then I moved on to private sector and then I stayed there for seven more years. So it obliviously wasn’t that bad that I stuck around for that long but as I said, halfway sort of through my career, I started thinking, “Okay, there can be a bit more to what I’m doing.” There can be more to in the sense that I can get more fulfillment. I like what I do. 

I don’t like how I’m currently doing it, I don’t have much options in terms of how I’m doing it. So, can that be rectified by going the entrepreneurial route and a lot of it was. So I thought, let’s take that chance, let’s see what happens and worse case, I can always go back. So I decided to make that leap.

[0:08:05.2] AD: And a leap is a good word for it. For anyone who has been to the process, a leap is a great word. I want to jump into your story. I want to highlight something you said though, you said that you liked what you were doing but not how you’re doing that, and I can say for myself personally, and I can say, for countless other professionals I’ve spoken with, right? 

Where you’re performing a professional services that is a largely a knowledge driven resource, that has everything to do with your effectiveness and efficiency and how you get stuff done in leveraging your knowledge, and whether you’re a lawyer, an auditor or in your case, right? 

I mean, this is an ultimately, the number of folks that I hear that take the entrepreneurial leap, tend to be those that enjoy the work, enjoy what they do in many ways but just look around and say, “There has got to be a better way to do this, there has to be” right? And it sounds like that was your motive there, right? 

There’s like, “I like this, I see opportunity but I want to go do something. I want to go do it differently” right? Okay, so you took a leap, talk to me about that? When did you do it, how did you decide, what did you learn, let’s dive into that process?

[0:09:10.9] IS: So I took the leap and it was a major leap because ultimately, when you're coming from that set salary, set processes, everything’s set and sort of given to you, easy to get complacent when you’re in that work, larger organization thinking, “You know, I can do this” it’s not until you step away that you realize, you take a lot of things for granted, like paper and photocopier and just having like the Internet and simple things that you then become responsible for because now, you’re in charge of everything.

So I think the largest meat was just not knowing at the end of every month that you’re going to get a set salary transferred to your bank account, and that you then have to determine how and what you’re going to make. Even though that’s what you signed up for, it still doesn’t hit you until you’re actually doing it and it hits you more when you think, “I’m doing everything right, but nothing’s happening.”

So I think that is the biggest leap. You know, I started out thinking, “Okay, I’ve planned for it, I’ve set aside some salary, this is going to be able to take me through, for you know, maybe a year or two” and I thought, “By year three, I’m going to surpass what I need, I’m going to be doing great and you know, all the naysayers are going to be saying, “ha-ha-ha, yeah, I wish I was her”” That didn’t happen.

Year three, I was still struggling, I was still thinking to myself, “What am I doing, should I be looking to do go back to a set sort of organization that’s going to give me a set salary, have that, you know, stability” and then I said, “I could do it and I could do it and I could do it well but I probably wouldn’t enjoy it.” 

So I said, “You started it, stick it out, let’s see what happens” and I would say, by year four, it was when I was starting to see, “Okay, not only have I surpassed or not only have I started making more, I surpassed where I was four years ago when I had actually left” sort of private sector and having a set job.

Now, that may seem sort of insignificant because yes, you surpassed where you were but you could have done that thing in that same job. But not only did I surpass where I was in terms of income, I just had greater autonomy, greater control over my life. I could determine what I did, when I did it.

Not everyone needs that and not everyone wants that but for me, I wanted that, I needed that sort of work life balance and it sounds, you know, very trendy now and it sounds very, “Oh, everyone’s doing it” but I can tell you, seven, 10, years ago, it was not topical. It was not trending, it was still very much, “Are you crazy, do you know what you’re doing? Why would you do that?” 

Because, you know, you can easily be on a very good track in an organization, get hefty bonuses and just sort of stick it through but I thought, it wasn’t for me and I’m just happy that I actually made that decision to stick it out because there were a lot of times where I thought based on the number of deals that I was getting, that it wasn’t for me. 

That I should just go back and just go back into, you know, where I wouldn’t have to worry and I would have to hunt and I wouldn’t have to seek and I wouldn’t have to just get all the rejections, you know, on a regular basis.

[SPONSOR MESSAGE]

[0:12:09.2] ANNOUNCER: This is Branch Out, a Connection Builder’s podcast.

[INTERVIEW CONTINUED]

[0:12:17.5] AD: So I, again, I commend you in that process because it’s sticking it out, it sounds like the really important element. I want to dig into that in a second but you made me think of something when you said that the leap, and I’m speaking a little form my own experience but also from others that I’ve had a conversation with.

I think often times, the initial leap is almost easier. It’s almost the easy part because it takes time to mentally get yourself there and say, “Okay, here’s what I want to do, here’s why I want to do it” and the “why” very often times, it’s autonomy for most folks I talk to in entrepreneurship. You use the word specifically, right? South Asians see autonomy, control over one’s destiny.

Fiduciary, your own time, stew at your own time, however you want to phrase it. It’s like, you want control. Even back to the statement of, I like what I do but I don’t like how I do it. The how I do it has everything to do with the autonomy, the control, the – again, in my own experience, you wrap your mind around “Okay, that’s important to me and I’m going to go do it.”

You build the confidence to say “Yes, I can do this, I’m confident in my own skillset, my own ability to go do this and I’m going to drive for it and do it.” You do it, I call planning and you know, the financial element, the economic element the execution, you can only do so much before you actually have to go start doing it but you step back and say, “Okay, here’s what I think, here’s how I can pull it off, here is what I’m going to do.”

And then you take that leap and that leap is again, I think almost easier and often times because you’ve mentally gotten yourself there, you’re hyped up, you’re ready, you’re good, and you do it. There is definitely the first missed paycheck, it feels a little weird, the second this paycheck feels really weird, the third, fourth and fifth one, which you were saying, “What is going on?” 

I think it’s harder in that I think and I don’t always necessarily a point in time as much as it is a spectrum but time goes on that leap, if you will, becomes harder and harder and harder and harder and I think maybe instead of the word leap, maybe the real way to look at this is the endurance, the perseverance, right? 

Because pushing through it all, because ultimately, you made that jump and now you have to figure out how to keep pushing through it. So tell me about that, tell me about the “pushing through phase?”

[0:14:24.3] IS: The pushing through phase. When you’re in it, you don’t think you’re going to get out of it because you feel like—

[0:14:29.1] AD: You feel trapped?

[0:14:30.3] IS: You feel like you’re constantly pushing but I think, a lot of it is that once you’ve come so far, you’ve said to yourself, “Okay, well, you know, how much further do I really have to go before I start seeing this whole light at the end of the tunnel?” or “How much further do I have to go before I just call it and say, this is too much?”

But I think you just have to stick it through and I had friends that come in, try to do the same thing and a year in, they’re back and we just said, “This is not for me. I can’t do it, I don’t have the perseverance, I don’t have the patience to wait just to get out to see if it’s going to, you know, sort of be fulfilling for me.”

And I stuck it out because I knew that, had I not stuck it out, what I was going to is not going to be genuinely where I want it to be. So I would again be for a lack of a better word, stuck. I would be okay in the sense that I knew every month, I was going to have that set salary come to me but I would be probably very unhappy.

So I stuck it out because I knew that ultimately, I would have to make a decision. The decision would have to be, are you going to stick it out to see that it gets as good as you thought it was going to be? Are you going to stick it out and just see that it’s going to be okay for you to survive?

For me, there was – even though I knew the thought within the back of my mind to go back. It really wasn’t an option. I just thought that there was so much happening around me and there were so many people talking to me saying, “You know, I’m so happy for you, I‘m so glad that you're doing this” not knowing all the struggles that I was having. 

Not knowing that I was thinking to go back and constantly say to them, “You know, it looks glamorous” right? It looks glamorous because you think I’m at a coffee shop today, you think I’m out picking up my kids, you think I’m doing all these things and there’s nothing behind it.

But what you don’t see are the late nights where I’m constantlytalking to people on LinkedIn. I’m sending in the messages, I’m traveling to New York, I’m pounding the pavement, I’m spending my own money to get business and I don’t get anything.

You haven’t seen that, you don’t know that because – but that’s what’s happening behind the scenes and that’s what happens for years and then, you know, you start getting small glimmers of hope. 

You get previous clients that say to you. “Hey look, we worked with you before, we heard you’re still in the industry, do you want to come onboard?” and you say, “Oh, okay, yeah, sure” and then slowly, those clients start adding more and then you realize, “Oh look, I’m growing” and not only am I growing in terms of having more clients, I’m growing in terms of the income that I’m getting. So now that’s one thing that’s off of your back.

You’re not too concerned about what you’re making and at the same time, you are still not having to focus so much on all the other small stuff because you’ve done it already. You set the base, you’ve done the ground work, you’ve done the planning, so now you’re just constantly trying to build.

So I think the biggest thing is, sticking it through. As hard as it is, I think you just have to stick it through. I think you have to know who you are and what you want and if you know that, I think that is going to make all your decisions that much easier. 

For me, I knew that I wanted to do this. I think a lot of people that have come and tried and were not successful, they wanted to do it because they wanted immediate success. They wanted to be back where they thought they left and they wanted to be able to say, “I’m still making he same thing but I can do all of these other things and me time.”

Well, that’s not the reality. So I think you have to know who you are and know what you really want out of it and then that will guide you in terms of whatever decision you end up making.

[0:17:51.0] AD: I’m going to share a little of my own experience reflecting on what you said there because a couple of things really hit home. I think it’s very easy to instant gratification is the word I guess I grab. It’s very easy to say, “Well, I want to go do this, I want that” right? 

And it’s also very easy to look around at other success that you see from the outside and not have a darn clue what’s going on behind the scenes. Whether the success isn’t as real as the success it might look or whether it is the number of challenges that we’re endured to get to that success that you’re unaware of, right?

So recognize that I’m saying for myself personally and anyone listening, if you are an entrepreneur, if you’re going through that, either you’re taking the leap or you’ve taken the leap and you’re working through it and even just general in life, when you started comparing yourself to someone else, “Well look at their success and look at that” it becomes really – it’s really easy to stumble down a trail that’s not going to get you anymore productive. 

So it’s looking internally and then what you said that really hit home is, you’ve got to know who you are and what you are, right? And who are you as an individual and what do you want and what I heard you saying that I look, I do myself and I think a very similar prism is, who you are is someone who want to set goal, sticks to it, pushes through and will do what it takes to get where you want to go.

That drive, motivation, grit, determination, that real motivation to keep kind of going but then, also what you really want, it is the agency, it is the autonomy and I think many folks want that. I think most humans you talk to, I know there are studies out there that point to the greater level of agency.

Someone feels the greater level of happiness and satisfaction they feel in their job and their life and I think as humans that tends to be something we all desire to have but really, being clear to yourself on why that’s so important and how you want to achieve that and not keeping yourself centered in, reminding them that. 

I have to imagine for you, again, speaking to my own experience to this, I have to imagine that that’s what helps you keep going on the hard days and I’m sure it’s a constant battle of reminding yourself that, “It’s going to be okay” or “I am doing this. Here is why I’m here, here is how I show up” maintaining that kind of personal confidence to continue to persevere.

[0:20:02.5] IS: Absolutely, absolutely and I think one of the things you touched on was that, you have to know, what is more important? So for me, while I wasn’t making this same sort of income for years that was not as important. Yeah, it’s all good and you want it but that was not as important as having the greater control of their bigger agency, having to counter best, how I did, what I did and when I did it. 

So while that one aspect is missing, for me, I was still happier because I was having a lot of those other things were being fulfilled. Whereas, if you don’t know that for yourself, it’s going to be difficult because you’re going to be saying to yourself, “Well, you’re not happy” despite the fact that you have all these autonomy but if people are driven by different things, right? 

So if someone’s driven by you know what they’re earning and what they’re making and they’re not doing that for several years, it’s going to be hard to be able to stick it out because you’re not getting what’s giving you satisfaction. So while we may want the greater autonomy as well, that may just not have as a significant of an impact on them than getting that high salary, that instant gratification right away. 

So, often times, that’s why it’s harder for some people to stick it out because it is a tough road, it is tough to get back to sort of, you know, pretty entrepreneurial earnings.

[0:21:15.4] AD: Instant gratification is the word I want to sit around and if you speak to anyone in the baby boomer generation, I think that’s the number one way they would describe a millennial or the younger generation, right? And we do live in a world of now, right? You and I are 1,200, 1,400 miles apart right now and talking. The world of now, right? 

I mean, it is the world I understand. I’m a very – if I were to describe myself, the word impulsive is probably the word I would use. I love things now and so, I get that. I just want to point out for listeners to remember, this isn’t a macro or broad statement that’s always applicable but money tends to be instant gratification terms of a measurement form, right? 

Wealth, wealth is measuring delayed gratification. Income, money, cash flow, often times is much more in terms of instant gratification and that’s not to say we, understanding that people have a lifestyle, that you have responsibilities and requirements and it costs money to live, right? 

I mean the reality of our world, you have to have some kind of economic model or a support system that allows you to be able to continue to live and thrive. Knowing that, often times for many folks and I definitely sense this myself, I’ve seen this in many others as well that I’ve worked with, there is a level of recognizing the difference from what you need versus what you want and understanding where that gratification comes in. 

Knowing that some of that sacrifice, some of that discipline to say no and to delay the gratification can at least for me, has ignite it more personal growth than probably anything else is being able to see through that and make that mindset and hold onto that, recognizing that over the long run and it is really easy to think about life in one, two or three-month intervals or even a year but think about, anyone listening, think about what’s changed in your life in the last five years. 

I know there is one major thing that changed for all of us in the last five years that we never would have seen coming, right? A lot can change in five years and five years is it feels like forever at times but it’s also a short period of time and when you really think about a lifetime or a career time if you will, it is very easy. I guess the whole point I’m driving at is it’s really easy to get stuck in instant gratification.

To get stuck in the here and the now and not thinking about the what could be, what the future could build to if you persevere and continue to push into what you are trying to accomplish. 

[0:23:37.5] IS: Yeah, I agree with you 100%. I think that that is a lot of probably what causes people not to stick things out a lot as well because when you look around, if you are driven by instant gratification and you look around with the people around you that’s saying, “I’m stuck” in their traditional jobs or getting that set income, they look as if they’re progressing much farther and much quicker than you are because you’re in the entrepreneurial stage where you’re building. 

You haven’t gotten back to where you were before but you see them and they’re buying new cars and they’re buying new houses and they’re travelling but you’re not doing that because you had to set yourself up to say for the next however many years going to take me, those things are going to be, you know, secondary to me building my business, to be building my practice to me. 

So I like what you said in that five years plan, so much may have happened with the people around you but if you focus on them, you are going to lose focus in yourself, right? Because you are going to start thinking about, “Well, how come they’re doing this? How come I didn’t do this?” and I feel like I’m being left out but you focus on yourself, you focus on where you’re going, keep your goal in mind at the end of that five years. 

Then it’s not a us versus them or you know, a competition but at the end of that five years, you will have seen that despite the fact that you did not do all those things that you thought everyone else around you that was doing it and they look very successful, I’d like somebody to tell me at the end of those five years what they look like as an entrepreneur and I am almost pretty certain that they are very successful in every aspect with one, the autonomy on their life and then also their income. 

So yeah, you can look around and you can say, “Well look, you know I can get to this point XYZ much quicker if I do this” but is it really what you want and it goes back to knowing who you are, knowing what you want and then just focusing on that and sort of shutting out all the other noise that surround you because if you don’t, you can easily get distracted and it is that much easier to say, “I don’t want to stick this out” because you’re busy focusing on everyone else’s and their journey as opposed to staying focused on yours. 

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[0:25:41.7] ANNOUNCER: This is Branch Out, bringing you candid conversations with leading middle-market professionals. 

[INTERVIEW CONTINUED]

[0:25:49.1] AD: A really important point to remember, for anyone who is either currently enduring the journey if you will or anyone who is thinking about taking the leap and starting the journey, remember that what you consume and who you are around can influence your thinking profoundly and it is if you are surrounding yourself with individuals who are living a different life or living in a more traditional type setting, the reality is you are likely to be part of conversations and to hear things and hear discussions or see things that are going to be very in contrast with how you are trying to live and it can make it very difficult to keep yourself centered and on track. 

Now, I am not saying throw away your friends and community and find just a group of entrepreneurs to hang out with but I am saying that you should be conscious of knowing who you’re talking to and conscious of how that affects you and how it can shape kind of your own thinking because again, I can speak very openly from my own experience in this. There are a number of friends that I have personally or my wife and I have. 

There’s a couple of friends that we spend time with and great people, enjoy the conversation, love the relationships I have built with them but also sometimes the discussions, we just talk about wildly different things because to your point, you said that comment about sitting in a coffee shop. It looks great because you are sitting in a coffee shop and so on one hand, they’re saying, “Oh, that’s so cool” you’d sit on a coffee shop. 

On the other hand I am saying, “Do you realize I am frantically sitting in the coffee shop trying to figure out life?” right? Then on the other hand, you’re talking to them there, “Well, we did this or we’re doing this” and “Well, I can’t do that now. I have to put that off. No, I can’t partake and it is challenging but again, the point I am driving is recognize that who you surround yourself with, the conversations you have, what you read, what you listen to, what you watch on TV, all of that really affects the way you think. 

In so much of the journey especially in that front part of that initial onset of going through an entrepreneurial kind of journey is around that determination, that grit, that focus, that endurance and it will make it harder. You are adding more friction to the journey the more you’re around that type of discussion or thinking that way. 

[0:27:58.5] IS: Yeah, I think there is a saying, I can’t remember exactly how it goes but basically saying you attract whatever you’re surrounded by. So if you’re surrounded by you know, people that are in different path, then you then – chances are that’s what you’re going to attract, that’s what you’re going to become. I think having that sort of key circle is important not just personally but in the professional arena as well because relationships are so important for building businesses. 

It could be for simple things, it could be trying to have a new automated service but if you are surrounding yourself with likeminded people, you know, perhaps there’s some within that circle that can help you and say, “Hey look, I work with Alex, he told me about this guy. Why don’t you check him out?” or it could also be even more to the point where you can be getting business from certain people. 

So I take your point, you know my husband and I also had friends that are not necessarily in the same path as we are and for their own reasons, they think that you know, having that set nine-to-five is what they do, which makes sense but they don’t understand the risk. They don’t understand taking chances, they don’t understand being entrepreneurial and they don’t understand why sometimes you make certain decisions. 

But again, there is different mindset for being an entrepreneur and I think you have to be able to foster and continue relationships in a way that are going to benefit you professionally and personally. I am not saying like you were saying earlier, you know, you don’t have to cut those friends lose but you just have to know when you’re building a business and where you’re trying to get you just stay focused on that and not sort of get sucked in to things that are not going to benefit you professionally and personally because it is easy to get suck that way. It is really easy. 

[0:29:32.4] AD: Unbelievably easy and recognizing that tradition of society, most people in their social circle, you’re an entrepreneur you are stepping outside of it by a longshot, right? I have read a number of books and articles and just kind of thought leadership around entrepreneurship and two things that really jumped to mind that I have seen often times is one, being an entrepreneur is unbelievably lonely at times. 

It is not different than you know, the CEOs of large organizations tend to feel the same way, right? Anyone that is in a position of leadership can feel very isolated and as an entrepreneur, you are in a very leadership focused, right? You lead your organization, lead yourself, lead anyone else that’s part of your team and it can be an isolating lonely journey and know that because of that, it is really important that you do find a community. 

You find a circle and you find folks to speak with that help with that because the loneliness, the isolation can make challenging to function or to show up as your best but also recognize that I guess maybe the second point that I’ll point out, I’ve seen many, many people, right? And talk about entrepreneurship is loaded with anxiety and depression, right? That I think has to do with the isolation and there is a lot of challenge. 

There is a lot of overwhelm that tends to come with it. So it is important that you find that support, you find those folks and you know, maybe a word of advice for anyone going through the journey, if you find yourself in a point where it is really hard, make sure you’re taking care of yourself. You have to show up and do things that are good for your mental health and it’s always easier said than done but take care of yourself and recognize. 

For myself, when I am in a rough patch or having a hard week or hard day, I’ll get more done by not working and taking a little time for myself and then come back to it later and if you have to do that as an entrepreneur, you have to keep yourself in the right headspace and keep yourself focus to keep pushing through and know that on a daily battle, it’s going to be challenging. 

[0:31:24.9] IS: Yeah, I mean so much of that rings sort of so true for me. You know, mental health is obviously I think of coming out of the pandemic, you know, I think there’s a lot more focus on it now because obviously there’s a lot of working from home and people like seeing people and interacting and things like that but as you said, being an entrepreneur it is very, very lonely because I don’t even know what percent of the world is entrepreneurs. 

But then when you start going down to people that are in your industry and doing the same thing that you’re doing, it gets to be an even smaller and smaller circle. So you don’t have people all the time that you can sort of you know, say create a network with but you have to try to put one in place. I think it is very important to have that one thing that you do to help you with your mental sort of wellbeing because you are going to get to a lot of stages a lot of times on many days, where you’re just burnt out. 

Because you are just constantly going, trying to find your relationships, those relationships are failing and trying to find new clients that’s failing, you’re just always trying. You feel like you’re always going and you don’t have a choice because you are the marketer, you’re the accountant, you’re the engineer, you’re so many things all in one because you are growing that business and I think you know, find that thing whether it means going to work out, whether it means going for a long walk, yoga, whatever works for you, find that and sort of stick to that. 

Know that recognize when you’re getting to that point where you need to do it, take a break, things can wait. You know, as much as you feel like you always have to be on but I think if you don’t show up in the right way, you are not going to benefit the business anyways. You do have to take that time off. If it is an afternoon, if it is an hour or you know, you don’t check your emails for a bit but just take that time out, check your mental state of being. 

Just continue to sort of focus on yourself, sometimes almost as much as you’re focusing on the business because they have to go hand in hand, right? We can’t just neglect one for the other because you may not have one if you have the other. 

[0:33:16.4] AD: Ultimately, they are one and the same often times as the entrepreneur, right? If you want to lead your business, you have to lead yourself, right? So if you want to practice what you preach and I think everyone around that I speak to on entrepreneurship but also most people in general say yes, it’s important to take care of your mental health. Yes, you have to do things for yourself. 

Yes, you have to have balance and we all know there is some value to that. As an entrepreneur, no one makes you do it. You don’t have weekends off, there is usually no distinction between you and work and so you have to lead yourself to that. You have to yourself do it and it’s always easier said than done and you have to focus on those habits to really endure and push on and I think that’s broader than entrepreneurship but I’d say in entrepreneurship in particular, that can be unbelievably important. 

[0:34:01.2] IS: It is and you know, just going back to what I started out with before talking about the coffee shop, you know, people will say, “I see you at the coffee shop” they don’t know what you’re doing at the coffee shop. They don’t know you are waiting for a client that said they were going to show up and they didn’t show up or they don’t know if you are trying to figure out, you know, your next marketing ploy that you try to get new business. 

But the thing, like you mentioned with entrepreneurship, you’re always on and always off. You don’t have a true vacation, you don’t have, you know, people can set their own office to say, “I am out of office for two weeks, contact so and so” and then when you get back, you peel through 200 emails if you feel like, that’s not how it works for entrepreneurship. You don’t have an out of office because you’re always in office. 

It doesn’t matter if you want to take a trip, you’re still expected to be on call, you’re still expected to respond and you have employees and you’re still always constantly in meetings. So while the outside world is, “You’re so flexible, you get to do this, you get to go here, you get to do that” yeah, I am but as much as you see me that it looks like I am off, I am always on. I am always on and that is what’s also so important. 

When you come back to the mental state of being because you’re always on, it is so crucial and critical to realize that you do need to take a break every once in a while to make sure that you keep your mental state of mind in the right spot. 

[0:35:19.1] AD: I have spoken about this I think on a previous podcast, for anyone listening, check out Jay Harrington’s podcast, I think it is number 92 and we talked about this idea that agency and freedom and autonomy, those are all things that require responsibility and discipline and self-discipline. That’s what I think at the root of all of this is, it sounds really nice to have agency or freedom until you realize what that means is you have to make every decision for yourself and making that decision of when to work, what to do, how to do it, why to do it. 

How to take care of yourself, how to balance and know that there is no easy way around it. It can be very fulfilling, very rewarding. For me personally, it’s helped me grow as a person more than anything I could have imagined, any part of my career prior to this but it really is around taking that discipline and that responsibility to show up and do the work in the right way and balance what you are doing to make sure that you show up as the best version of you. 

[0:36:19.7] IS: Exactly, discipline is key. I mean, starting out as I said 10 years ago, I didn’t have to be at work at 8:30. I didn’t have to be at work, I didn’t have a lunch hour, I didn’t have to be off at five. So you start thinking, “Okay, so then now what am I going to do with my day? Okay, well I need to make money. How do I do that?” and it goes back to discipline. We could sit there and we could spend the whole day watching TV or we could go to the beach. 

But then, what was that going to do for you and how is that going to get you to where you need to be and then slowly, you realize that that discipline then goes into overdrive because at night when you should be relaxing, you’re on LinkedIn trying to make connections. You are trying to do this, you are trying to reach out to that next person. 

So I think discipline is really, really key and I think in the beginning that is something that any person who is currently considering getting into entrepreneurship or you’re in the early stages, just be disciplined set yourself up in a way that’s going to be productive and even though you may feel like you don’t have to get up at 8:30, maybe you don’t want to get up at 8:30, maybe that is your agency that you decide your day is going to start at 10. 

But whatever you decide, stick to it and make sure that that is how you start and go through your day and see what works for you. Obviously, things may change and you may have to change that up as time goes on but I think the key is having that discipline and showing up when you said you are going to show up for yourself because there is no one behind you telling you before you’d even show up today. 

The only person that’s going to tell you that is you and the only time you’re going to realize that is when a few months down the line or a few years down the line, you are not where you want it to be and probably a good portion of that was because you were not showing up or you showed up and you weren’t fully committed to what you said you were going to show up for. 

[0:37:58.1] AD: This is probably a great kind of wind down to this conversation. If I had to and you tell me if you agree with this but if I had to look back and say there’s one thing I would tell myself of being on the journey or one thing that I credit towards keeping me going both in the early onset of even today and one thing I would recommend to anyone and anywhere but especially as an entrepreneur, it’s bring daily intentionality to how you’re spending your time. 

That’s the autonomy, that’s the control and you can do anything you want and you don’t have to work 16 hours a day to be successful. If you are focused, you can get a lot done in six hours a day. I mean, you can get a lot done less in that even. It is less about the exact way you do it and much more about the thoughtfulness and the intent and the consistency of sticking to the plan, the discipline to stick to the plan, which often means you have to track what you do and know what you are doing and become aware of it. 

Bring awareness to it so you can actually monitor or find the gaps between planned actions and actual actions but it is all about intentions. It is all about that intentional thoughtful approach and if you spend your time going all the way back from the very beginning, “I like what I am doing but not how I am doing it. I want autonomy, I want agency” well, that just means I want control of how I spend the 24 hours in each day that I am given. 

Once you really hone in on being disciplined about that, that’s the way that you tend to get much, much more accomplished over the long run. 

[0:39:21.2] IS: Absolutely. I think you’ve summed that up more succinctly than I could have but I think that’s exactly what I was getting at and that yeah, in the beginning we came out, we said you’re going to be an entrepreneur for a reason, stick to that reason and sort of you know, put that time and place that works for you. What works for me may not work for Alex and what works for Alex may not work for Jennifer. 

But at the end of the day, we all have to find what works for us and stick to that so that ultimately, that end goal and I think we didn’t talk much about it but you know, having that focus in mind as to what your end goal is going to be and just sort of work towards that slowly to pull me at that, whether it’s a daily chip at it, a monthly, a weekly, a yearly, you know, three years but just constantly have that goal in mind. 

I think for me and in the early stages, I set it down and the goal was not just financial. A lot of it was to do to be able to spend time with family, to travel, to do a lot of things obviously that are tied to having financial means as well but I think you have to set that out and that’s the only true way that you are going to determine where you as successful as you thought you were going to be. 

Obviously goals are going to change along the line but then people start to get a bit – they lose focus and you started out saying that year three, you wanted to make X amount, you wanted to do this and you made that but then, “Oh, I wasn’t that successful” but that’s what your plan was. So I think a lot of it is just reminding yourself as to what your plan was, what your goal was and staying true to it. 

I think it’s not easy but it is definitely possible and I think anyone that has that inclination to be an entrepreneur should go for it. I think they should do it. 

[0:40:54.9] AD: It is probably a topic for a whole other podcast but you’re coming around goal setting, knowing what you are trying to achieve and why but more importantly, recognizing that expectations change very fast. Anyone who has ever been through a career that has some large financial step-ups can understand lifestyle creep, how at one point in your life you thought you needed to make X and then all of a sudden you need three X to be able to live, right? 

I think we have all been through that from time to time and that happens. The whole point around this is being intentional and thoughtful in what you are doing and recognize that set that goal, follow that goal, track what you are trying to accomplish. You are not going to hit every goal, know where you’re going, know things are going to change and realize that as long as you’re progressing forward, that’s what matters more, right? 

As long as you are continuing to take baby step forward, one percent better every day type approach, you will get where you’re going much faster once you start focusing there and less so about what you think it should be, what you want it to be and rather embracing the journey that the specific place you’re at and just being intentional and spending that time, setting the goal and knowing your why and pushing towards it. 

[0:42:00.7] IS: Yeah, I agree whole heartedly. I think that’s certainly key. Again, a bit about what we talked about before, it is easy to get sucked in and forget about what you set your goals to be, what you plan and then all of a sudden you think you’re not as successful or you didn’t do as great but just always go back and check and think and then for me sometimes, I go back and I think about a two year, particular time I realized. 

When I thought that things probably could not get any worse and we had to get better and then you realize and you thought to yourself, “Can I make it out of this?” and then you look at where you were now and you see not only did I make it out of it, I made it out of it and I’m doing so much better than I thought I would have done even at the time when I only wanted this much more to be happy, I got so much more than I wanted. 

So I think that’s always key, just sort of you know, reflect. Reflect and don’t forget sort of what you set out to do and I think you’ll be fine. 

[0:42:54.0] AD: And appreciate what you get, right? Because you said you may want one thing but you get something else and if you truly reflect on it and look at is especially in the long run, those tend to be the things that you really need it more. Back to what I want, wanting has a lot to do with instant gratification very often and so keeping mind of that. So this has been an awesome conversation. 

I really appreciate the thoughts and insights you shared. For our listeners, how can they get in touch with you? 

[0:43:18.0] IS: Sure, so I am on LinkedIn, you can find me Isatou Smith or my email is ismith@eagovernance.ky. Any of those options are pretty easy and yeah, I am always available. I’m happy to have a quick chat, help you out with anything Cayman related or anything entrepreneurial, you know, happy to help and happy to lend a hand. 

[0:43:36.0] AD: Well, we’ll make sure it’s linked in the shownotes below and for any entrepreneurs that are aspiring and want some knowledge, feel free to reach out. So I appreciate your time again, this is a great conversation. Thank you. 

[0:43:46.1] IS: Thank you so much, have a great day. 

[END OF INTERVIEW]

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