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On this episode of the ‪@WhatWorked‬ podcast, Tyler Rachal and Mike Wu sit down with Ian Jackson, CEO and Co-Founder at Enshored. Are you interested in learning about the BPO industry? Listen to this episode to hear Ian's insights from building his company.

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We covered a ton of great topics:

• Transitioning from FinTech to bootstrapping a service firm
• Overcoming unexpected challenges
• Asking for and giving help in the professional world

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Transcript edited for clarity:

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Tyler Rachal

We're back. We're live. Another awesome episode of What Worked Podcast. We're on episode, we were just talking about this, we're on episode 12. So, gosh, I feel like I blinked and we blew by episode 10. So for all the haters out there that thought we wouldn't make it this far, we're eating your lunch, buddy. 

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Mike Wu

This is for you.

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Tyler Rachal

That's right, it's for you. Speaking of haters, just kidding, with a hilarious  introduction. Today, we are joined by, first and foremost, my friend for a long time, Ian Jackson. We've known each other for a very, very long time, all the way going back to our days at a little startup called, TaskUs, which has now gone on to do many, many, big things and be huge, hire thousands of people. 

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Ian and I connected, there and we've stayed really tight, as you tend to do with the folks that are kind of in the fox hole with you. But now he's the founder of a wonderful company called Enshored, and Enshored is very much in the same space as Hireframe. So I'm particularly excited about this episode because I have a lot of kind of inside baseball questions for Ian, but, Ian, if you don't mind as his customary on what worked, would you mind giving a quick introduction? Who you are, what's Enshored, maybe who your kind of core customer is too. That'd be great to hear about that as well.

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Ian Jackson

Yeah, thanks, Tyler. Thanks, Mike. Excited to be here. So I'm Ian Jackson. I am the CEO and co -founder at Enshored. I am originally from Scotland and worked in FinTech in the UK and globally prior to moving out to California in 2012, which is when Tyler and I's bonding started over him teaching me all about these things called Philly cheesesteaks, as I recall, on Fridays. 

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Tyler Rachal

That's right. Magical things.

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Ian Jackson

Yeah. At Enshored, I've been set up to support disruptive startups with outsourcing services for the past 10 years. And we just recently kind of popped through our 10 year anniversary, which is quite exciting. At this point, we're somewhere around about 2,000 employees and we've been growing pretty consistently over the past six or seven years. I think with everyone else, we're having a little pause right now, but it seems like growth is just around the corner again. So I'm quite excited by that.

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Tyler Rachal

Definitely. And Ian, you're officially our first, do I say Scotsman? Is that the term? You're our first Scotsman on the pod?

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Ian Jackson

I'm definitely not Scotch, that's a drink. Scot or Scotsman, I think is fine. Yeah.

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Tyler Rachal

Okay, there you go. You're our first Scott or Scotsman on the pod. So very excited. And I'll say that, Ian is extremely humble, being at TaskUs, and going through their hyper growth years as  a BPO or outsourcing company, and then now growing Hireframe, I'm extremely appreciative of just how hard it is to build one of these businesses. And you are at 2000 employees. What you didn't include was the fact that you've been named to the Inc 5000 list several times, which is very hard to do. One of the topics we're going to dig into right here, right away is just the challenges in building a bootstrap service company. I know that in this space in particular, there are some unique ones. So I guess a, the, the first question I want to jump into Ian is when when you were growing Enshored and getting those first couple of logos, and then hitting those first couple of growth spurts, what are some of the challenges that you ran into that relate to a service company and specifically a bootstrapped service company?

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Ian Jackson

I think the decision to be bootstrapped came through partially choice, partially no choice. But, you know, there are people out there like Mike Bloomberg, who built his empire and never gave away a single share of that company to anyone. He built incentives to keep employees highly motivated, but he kept ownership of his business throughout. And he was always kind of in the back of my mind of don't give something away if you don't have to. And I also think with the services business, there should really be, and I'm sure we'll talk about this in some more detail, there should be a pretty close link to your money in and money out, right? We're not investing in building a product. We are supplying a service. There is some hardware, software, other expenses around about the sides, but really what you're doing is providing a service to people, which you bill them for on a monthly basis, which kind of fits in with your, your cash out in terms of payroll. 

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So the idea was that we should be able to fund the business from a bootstrap perspective and also not with a lot of capital at all. And so that really led me at the beginning to make sure that from the very first contract that we signed, that we were clear that our operating margin was positive for a start and also with a view to how many of these clients that we need to have before there was going to be any money left for the founders to start earning some money from. And that was all kind of built into the economics of the business model. And we really stuck hard to that in the first few years.

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Tyler Rachal

I think people always love this question, so I can't help myself, but I am curious, when did you start earning anything from Enshored? I think it was quite a while.

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Ian Jackson

It was, I'm going to say year three where I started earning what I was earning in year three of my corporate life, probably inflation adjusted. So I don't know what that is. 20 plus years on and you know, it's like we're back here, but it just felt so different, because you could see the progress and you could see where you're at.

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And I think by that point we'd got through some of the key learnings, which could have killed us in terms of growing the business. And we'd had probably enough of our bad luck out of the way by that point.

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Mike Wu

We got to ask you about those, Ian. So you mentioned, you know, three years in, you finally felt comfortable paying yourself like a market salary. It sounds like because you learn certain things, you identified some risks and felt comfortable about how you're going to mitigate those. Maybe it was some growth things. What were some of the, what were those things that you learned those first few years where you were finally like, okay, we've got to grasp on this, I feel comfortable paying myself?

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Ian Jackson

So I think, going back to the cash flow cycle, it was more about when we had enough money in the bank, that there was something left over, which wasn't already earmarked for growth. And so I think this is a part of what you learn when you're trying to bootstrap is you want to go fast, but if you go too fast, you just run out of cash. And that's happened to us multiple times over the past few years.

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And to the extent that it really proved itself, I think the pandemic showed us that when we didn't have to keep investing in office space and all the depreciation that goes with that we got slightly ahead of ourselves on a cash position, which was quite nice. So we were able to breathe a bit more easily at that point.

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Mike Wu

Yeah,  I think that definitely resonates with me and Tyler. I think when you're bootstrapping a services business, I want to call out a difference between bootstrapping and raising capital, raising outside capital, maybe venture capital. When you raise venture capital for a business, you've got a stack of cash in your bank account on your balance sheet that is there to pay yourself a salary, most likely, even if it's a modest one, pay other salaries, invest in product, invest in the services, whatever it might be.

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When you're bootstrapping, you start with zero or sometimes even negative cash on your balance sheet. And what you're saying is like you wanted to build up some sort of cash reserve. That was a big part of it so that you understood, hey, this business is going to be a little bit more resilient. It's going to make it to next year. Okay, I'm going to start paying myself a market salary. I think that is a big difference between a bootstrapped and a venture backed business - You're starting from zero or negative. and you have to build up that cash reserve and that oftentimes means you're going to grow slower because you're taking the time to build up and stack capital to have that capital in your back pocket.

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Ian Jackson

Yeah. And I think you also don't have access to the same kind of advice. So some of the stuff you're kind of making up as you go along. Tax planning is kind of terrifying because you only know what you know, and you don't know when you're going to find out that you were completely wrong on something. So we're taxed, like many smaller businesses, as an LLC. So it's a pass through and you have to make all these estimated tax payments. And if you get it wrong, you get fined and that's money you don't want to have to pay. And you're just trying to learn all this stuff, right? Most entrepreneurs have not had a run-through more than once as bootstrapped, right? There are plenty of people who start a second company, but at that point they have all of that knowledge from the first time around. So they're not really in that position. 

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And for me, that was a big thing was just, I always wanted to make sure that I was hyper, hyper cautious about spending any money in case it really belonged to somebody else. And an example of that, and I still don't understand it, is how we get taxed in our subsidiary in the Philippines. Because it seems that they just keep coming back and asking for more tax after the end of the year. I have no idea what this tax is and why we have to pay more of it. I feel like we're already paying more than enough there, but they come back and ask for more tax. And it's just okay, It's really hard to budget and plan for stuff like that.

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Mike Wu

Totally. Ian, one thing about this journey, going from zero to three, kind of implied in what you're saying, how you kind of deferred paying yourself during that time, it's like you're saving, you're putting away capital for things like taxes and different things. But probably, I think for a services business, you kind of imply there's not really a product, but there is people.

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Ian Jackson

Yes.

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Mike Wu

I think people is the number one expense, especially for a BPO like Enshored. You have your team members in the Philippines. but you also have your HQ team members. And I imagine those were big investments for you. I'm just curious, as a founder of a bootstrap company, how you thought about the timing of making key hires.

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Ian Jackson

That's a great question. And I don't think there's a simple answer to it. And I think, we've definitely made quite a few mistakes on that. But what we tried to do with the early budgets is have a percentage number in there for non-operating personnel. And obviously we'd either be well above it or well below it, depending on had we hired somebody or not. And at what point does it just get too much? I need to get these things off my plate and I want somebody else there. So that's been a  constant challenge. And for me, the easier ones are where there's less kind of cash on the table. So obviously hiring people within the organization in our offshore locations and seeking out great talent there is less risky than doing it here in the U S where people are just, especially in Southern California, it's just so expensive to hire people. So you've got to be absolutely sure that you need the person and that you're going to get a return on them.

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And so that means a lot of time spent on interview panels and checking references and things like that. And my advice to anybody who's looking at hiring is always do your due diligence on people before you hire them, because you just don't know. You just don't know what's going to be out there that you could have found out beforehand that would have helped you. And sometimes it feels like you just come out of an interview with someone. It's like, this guy's great, or this girl's great. I want to hire them. And then you don't follow up on the references as you would do in your regular operations. Cause it's like, Hey, it's, you know, I'm the CEO. I can know better than my business and we'll, we'll skip that stage. And I think every time I've done that, that's been an error.

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Tyler Rachal

Something I think, Ian, that you've done quite well, just me watching your journey, is in growing Enshored, I feel like you've used your partners, your customers, really effectively in growing your business. And basically the thing I'm specifically referencing is one of the biggest challenges with a business like yours is the outlay of capital for building out new office space, right? So getting new office space, building it out. That's always the challenge, right? As you get a customer and they say, you always get those customers that are like, we need 10 people, but we might need a thousand in one month. You know, very like glass half full type folks, which is great, very ambitious. But I am kind of curious, how have you been able to do that? How have you been able to have those conversations with customers? We're basically saying Hey, I'd like to provide what you need, but also I'm going to need to kind of partner up with you on that. Like how do you structure your terms and how do you think about expansion, you know, through basically partnership.

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Ian Jackson

Yeah, so I think maybe just tackle it slightly differently. I think what I saw with our client base as it grew is that in the nicest possible terms and for the best possible reasons, they're all pretty terrible at forecasting because they write a budget and it's out of date within a quarter because they're growing faster than they expected to. Some of our clients really have that flywheel spinning and they've been going through major growth. And you're just trying to work out what do you need to do to keep up with that? So obviously having regular check-ins with them saying what does it look like? How much does the future deviate from where we think we're going right now? And then at some point, I think our aggregate organic growth with clients was somewhere around about 80%. And at some point we just had to say, let's just assume it's going to carry on. So let's get ahead of it and let's plan for the next office.

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So one of the things I think we've been really excellent at, and this was pre-pandemic and then we had a little pause for a minute and we're back in it right now, is finding the right office space, fitting it out for the right amount of money and having it fit for the clients who are gonna go in there. So right now we're fitting out some space for an existing client. That's quite easy because they're an existing client. They're just saying, we need to return to the office five days a week. We're gonna end work from home. So that's quite easy, but sometimes you're fitting out maybe a space for 400 people and you don't know whether you're going to have to divide that space into eight private biometrically controlled areas or whether it's okay to have an open floor plan. If some of your clients are going to be on the phones, if some people need some quiet space to work, you know, all that kind of stuff. It's really challenging. So we've been really lucky that first of all, we found a really good partner to build our spaces with and they've proven that they do things to budget, once we agree on a budget, it never goes up really afterwards. And that we, they help us think through all the decisions in advance so that that happens. And that they also deliver pretty accurately to their initial timeframes, which are quite quick. 

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And that's really important because, you know, three months is, you know, what we're doing right now on fitting out a space for, I think, 400 seats or something like that. And that's fine. Six months would not be fine because, you know, if you're starting to have conversations with a client and they need a bunch of space, you can't be starting off and say, yeah, we can do this for you, but in six months, they're just going to go somewhere else. And then the big challenge, especially when you're bootstrapped is you don't want to have a lot of space sitting around empty because that's just, that's just spent money or maybe it's an opportunity cost. I don't know.

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Tyler Rachal

Yeah, absolutely. And I know it wasn't always, you have this great partner now, but it wasn't always that way. I have to assume you probably had your fair share of terrible experiences. All I heard was budget never changes, projects delivered on time. I'm wondering who is this unicorn partner? Because that's not always the case, I would imagine.

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Ian Jackson

No. So we started off and we worked out of a Regus kind of shared office space. And that's how we decided we were going to spend our first year because we just had no idea. And we said, OK, we're going to overspend on this. We know this isn't the long term. We're going to do that. And then we tasked our then senior manager in the Philippines to go out and find us some cheap, very cheap office space to move into ourselves.

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We found it in a building where we were told there was air conditioning, but it just wasn't on because normally when you go and see spaces if they're empty, they're hot as hell. And it was, and it was on the 44th floor of this building. And after we signed the lease and moved in, it's like, can you turn the air on now? And they said, no, the AC only goes up to like the 38th floor. And it's like, what?

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Tyler Rachal

Wow, oh man

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Ian Jackson

So then we had to start finding AC guys to come and fit. And we actually had to rent out an extra office space because we didn't have enough electricity to run the AC and our computers, if that makes any sense. So that was a complete bust. We got out of that building as quickly as possible. It was terrible. And we learned a lot from that in terms of speak to the other tenants, find out what their experience is like, go in and out. And you know how things are in the Philippines. There's a security guard on the front door. How are they going to be? Are they nice? If they're not nice to you, they're not going to be nice to your staff, right? And if they're not nice when you're in sales mode and then really that building admin, can they get the right internet pipes into your office space? So you have a choice or you're going to get stuck with one provider and then they know that and they're going to mess with you. So I think we learned a lot of lessons very quickly with them. Yeah, we tried to do cheap and cheap was really not good value.

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All the furniture we bought fell apart within a year and everything. And it was a classic we thought we'd get away with this, but we won't. So we made cuts elsewhere. We found other ways to save money and we spent more money on nicer offices. But one of the things is that our customers, they might come to our office once a year, they're not there all the time. And so we really have to think about from the employee's perspective, what does a good office look like? And that is not the same as what you're selling to the client as the best office..

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Tyler Rachal

Yeah, because definitely clients want to come in and they want you to mirror something that they have in the US and it's just not necessarily the things that are important aren't necessarily aligned. And yeah, what you touched on something that I think is very foreign to people, anyone who's looking to potentially open up an office in a place like the Philippines. And I imagine it's similar in other places. You know, if you think about how you lease office space here, yes, you might inherit something that maybe you got to put some paint on the walls or ask for some tenant improvements or something like that. But the cabling isn't literally yanked out of the walls, which is what you inherit when you get a new office space, typically in the Philippines, unless you're using a Regus type type solution, there's literally nothing. And so you might think you're a tenant, but actually they're expecting you to invest in it like you're the landlord.

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Ian Jackson

Oh, absolutely. And it's learning that. There are some wealthy families who have a lot of the real estate in the Philippines and a lot of the class A offices are owned by them. But the class B, which tends to be where we go, it's mostly in the hands of smaller owners. And so, you know, it's just, it's very different. They don't have the access to the money and to do these things. And yes, that's up to you. And so you have to work out, OK, how much am I going to invest in this place for a five year lease? Now am I going to make it really good and we've had some really good experiences. Our first good office, we had a clause in the contract, to get in probably too much detail, But there was an escalation clause in the in the agreement for the years we had it. And then it said they would reset to market rates. And we'd actually taken another space in that building. So we knew what the market rate was. But our landlady actually said, no, you're fine. Just keep going with escalating rate at whatever it was, 3 % a year or something like that. And we just stuck with that. And so finding these people, some of it is chance, obviously, but some of it is just doing your homework and speaking to different people and looking at it.

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Tyler Rachal

Yeah, absolutely. And you've gone through, this is a tougher transition to make, but you've gone through a lot of these challenges, these stories that you sort of, you and I have caught up over the years, grab beers, that sort of thing. And I've learned about a lot of the challenges that you've gone through and you've gone through these largely alone. Yes, you are building a business with, as you put it, 2000 people, but largely you are the head of that business and it's you, you're the owner. 

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But that wasn't always the case. You did have a partner. I don't want you to have to go into any details that you, you don't care to, but your partner  very suddenly passed away. That was very tragic and I was talking to you shortly after that happened. I think one thing is founders, we really don't do a great job of talking about the hard times. And so I am just kind of curious, open-ended question, what you were going through during that time? What were some of the  things that you learned throughout that? And I guess a very direct question for you is, did you ever consider giving up is not the right word, but getting out might be the right expression?

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Ian Jackson

Yeah, so in terms of what happened, I started Enshored in 2014. So Jeff, my co-founder, and I met in 2013 through a mutual friend. We spent a couple of months working out whether we thought we could potentially be business partners. It was a bit like dating, I would say. It was kind of weird. 

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Tyler Rachal

We can relate.

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Ian Jackson

Yeah, yeah, well, you guys knew each other a little bit.

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Tyler Rachal

No, but we definitely had a courting period, no doubt about it, where dating is the right term. We dated, Mike, right before we got married. Hmm? Shrug?

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Mike Wu

Yes, no we did. No, exactly. I don't think it's that uncommon for co -founders. I think it's best practice actually to do the dating to get to know each other. It's actually more intimate than dating almost I think because like you're getting married way quicker than the average romantic relationship.

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Ian Jackson

Yeah, for sure. And so Jeff and I met and we definitely hit it off. The first two meetings were over beers, the third one, we got serious and it was over coffee from that moment on. And we sat and thought about culture, values, and all that kind of stuff. And then we kind of set off to start the business and part of his bootstrapping, he stayed in his prior job for a while until we had our first clients and that was fine because it actually helped him to bootstrap. He was out in the Philippines sometimes anyway. So that really helped us to, you know, to make, you know, make some connections over there and do some of the kind of basic groundwork, legal and banking and all that kind of thing. But he died within three years of us starting the company. He had a, he'd been living in DC and he'd come home to Southern California to go fishing with his dad and his brother. And he had a brain aneurysm and there is no coming back from these things. In his late thirties that was super sad. 

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And for me as a co-founder, I was actually in the Philippines at the time and his dad didn't know how to get in contact with me at all to tell me, because why would that be a connection, right? But he needed to let me know. So he actually used the contact us form on our website and I'm sitting looking at it and it's like, there's no way this is good news. At that point I could feel the hair stand up in the back of my neck. And I got a call and I don't think this is going to be good. And I was braced for something bad, but I didn't know what. And so it was that he was in a coma in the hospital. And it was only a couple of days before they said that there's no coming back. So they kind of turned it all off. 

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And I was completely in shock, which I think is probably understandable. but I'd never anticipated something like that happening, right? We had a risk log. We had a lot of things in the risk log and none of it really involved the two of us. I think we were doing okay at running the business together. Maybe we could have done things better, divided things up a bit better. And maybe we didn't talk things through as much as we should, but I think it was pretty, pretty good.. And then all of a sudden the next day I'm sitting there and it's just me at this point. And what do I want to do? Do I want to go on? Who am I in business with now? And I was lucky that, you know, Jeff’s family had his share of the business. And I went to speak to them quite a lot in that time. And we became really quite close. And his dad had actually built and sold a business, a fantastic car dealership business in Southern California and had basically retired. I think in my head it's in his thirties, but it must be in his 40s, but really quite young. 

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And so the family definitely didn't need the money and they understood this was a services business and a people business and if they had any future, probably I needed to be correctly incentivized. So we came up with a process for me to buy them out of their stake in the business, which allowed me a potential way out. But you know, obviously, I had to earn money to pay that back plus also then, earn money for a salary for myself at that point and everything else. And we're not talking about very much money, right? We're, we're living off my wife's earnings at the time. And it's also great that you have some other sources of income, and we had an Airbnb, I'm sure I was cleaning that. I think I was Uber driving for a bit just to try and make ends meet through this time. And we somehow came out the other end of it, but absolutely I thought, do I want to do this? 

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And I think I was driven by the fact that I think if the roles were reversed, there's no way Jeff is stopping. I do feel he's kind of still out there somewhere helping out and nudging me along at certain times. And even to the extent that his tone of voice and his values are still really evident to me within the business. So I think that's been something, but generally when you find the business, you set up an operating agreement and it's a three-year agreement. So we were just coming to the end of that first three years and we probably would have had a conversation about what we needed differently from each other. For me, it's a little bit sad that we didn't get to that point as well to really hear, because I think that's kind of your 360 feedback moment, three years in, like what worked, what didn't work and what do we need to do differently now. We never got the chance to do that and to the extent from that point forward, it was kind of a little lonely. You guys have got each other to cheer each other on. Sometimes I've had to make decisions without really having the same counsel, I have people around me who are super smart. Sometimes you feel like you don't want to make this their problem, it's your problem, so you solve it.

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Mike Wu

Ian, thank you for sharing that it's very hard to fully understand what you've been through and what you continue to go through and wrapping your head around this event. I'm curious for anyone else who might be going through an extremely challenging time like that, I'm curious if there were any things that you did to help you get through those really hard times, those really hard days. Were there certain people that helped you? Did you get on your bike and just ride a ton? What did you do to get through some of those harder times?

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Ian Jackson

As you both know, I'm a big cyclist. So I did ride quite a bit and that helped for sure, just helped with getting you motivated for the day. The other thing I really changed was I started asking other people for more help because I knew that I had this big hole and I got some coaching in some areas that I didn't think I was great and I remember I was really worried about our sales pipeline. I mean, ultimately that's one of the most important things. I think that by that point we'd solve most, we still had some  fire bells rung, but for the most part, the main thing that was a challenge was getting the right speed of growth. And so I spoke to a former colleague of mine who was a really strong sales guy, who also had started up a consultancy business in that area and he was getting hired by some amazing companies. And his thing was just tell me about your pipeline. And I walked him through it and he said, you're fine. You'll be fine, you understand what you need to do. You understand the stages. You've got this down. You understand what your sales cycle kind of looks like and you've got enough stuff in it. You can worry a little less. Now getting that kind of reassurance was really, really helpful.

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Tyler Rachal

Obviously you've made it to this point, which is incredible. But do you think long-term about things like you said you've done coaching before. Have you thought about putting together like a board for Enshored or just without over-complicating it, basically just somebody to kind of check you on some of your major decisions?

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Ian Jackson

Yeah, actually and this year, my board is mostly now my wife. She was a management consultant and stepped away from her full-time role with EY during the pandemic, because we were just really struggling with all the moving pieces and I was dealing with major challenges in that first year, just making sure we kept the wheels on. And she has done a ton of work in the areas, consulting into larger companies than ours. So for her, it's actually quite easy to see the solutions to many of these problems, which is great. And so she's been more involved over the past year in helping to work some of those things out and just helping me to get my head out of of the weeds and get up back up to 30,000 feet and see things a little differently and try and do more of the strategic stuff, which I think has just been a little missing. I think I'm just being focused on execution, execution. And the reality is I probably can't take six months out to go and open an office in another country as much as it was great fun. That's not my job anymore. I will not be opening country number three in the way I did opening Portugal.

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Tyler Rachal

Yeah, by the way, I can relate to the wife thing. I know your wife came from a background in consulting and working with these large Fortune 500 companies, same thing with my wife, she's at Deloitte. And it's funny, when I break down a problem for her, I feel stupid when I say the words out loud, because she kind of looks at me, she's like I'm missing what's the complication here. And it's just because I think when you're building it, you're just so ingrained in the details and you're so everything is quite, I don't know, you tend to overcomplicate it and then she'll just say something very simple. And I'm like, yeah, we could do that, but I don't know why we can't do that.

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Ian Jackson

Yeah, I think also you become really emotionally attached to all the decisions that they made in the company. Really everything is as a consequence of your actions. So I think your default is to get quite defensive when you get challenged about your direction. And that's something I've learned to just say, I just got to give that up and just like, let's listen, let's hear what's being said.

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The other, actually the other great boon I've had is that early in the company, we were ripped off. We were ripped off by someone and I thought I was quite smart and I had everything in place. I didn't consider that we would have a proper psychopath working for a company who was capable of forging bank documents. He basically emptied our bank account with the assistance of a bank employee. There's still a warrant out for his arrest, but in the Philippines. But afterwards, Jeff and I were like, how did we let this happen? What did we miss? So we went and saw his former employer and it turned out that he'd done exactly, well, not exactly the same, a completely different grift there, but also criminal behavior and had left them in a situation. 

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And I became super close with ultimately another co-founder of another BPO, a guy called Joeri Timp from a company called Eastvantage. And it was great because he kind of ticked a lot of boxes for me. He's European, so I was able to talk to him about a whole bunch of stuff that I just find hard to talk about with an American audience. So a little different and we had a very similar kind of growing pains in our business. Different, but similar. And so that friendship is

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been really, really important for me to kind of sanity check things. And both of us, when we've had big decisions to make, we reach out to each other and have a chat about it. We can be really open and I think that that's not something that happens in a lot of businesses where you can talk to your peers. But I think actually outsourcing is interesting because we're not necessarily all competing for the same wallet. There are so many clients out there, we can all quite happily just live in our slightly different lanes and work and coexist alongside each other.

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Tyler Rachal

Yeah, that's so funny you say that. So as some context, for anyone who's listening, Ian and I were on a panel together a couple of weeks ago, which was a joy to do. It's always good to hang with Ian and someone from the crowd actually asked that question. They were like, how are your businesses different? And it's funny because we're, we're obviously a slightly different focus. We do  remote staffing, all of our team members work from home and we tend to focus on positions where it's not going to be a team of a hundred people. It might be a team of three to five or maybe max 10 doing one single function, something like accounting and that sort of thing versus Enshored, it does a wonderful job in spaces like content moderation where you need potentially thousands of people. 

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But I love that point and I couldn't agree with you more, outsourcing is really weird because it's extremely competitive.You're oftentimes pitted against in every deal you're pitted against. It can be anywhere from two companies to 15 companies. But in a weird way, we're not competitive at all because it's just such a big blue ocean. The world of work is just always kind of, in my opinion, it's changing, it's growing. One vertical kind of gets automated away and then a new vertical kind of pops up or one scope of work, that sort of thing. So I couldn't agree more.

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I wanted to circle back on something you mentioned, Ian. You talked about opening your office in Portugal. So today, Enshored is operating in the Philippines, Portugal, and, some people in LA would consider a different country, the wonderful area of Long Beach, right? I think Long Beach would consider LA a little different, et cetera, et cetera. But I'm always curious about businesses like yours that are truly global, how do you think about building a really, really great company culture that is able to bring everyone together, everyone from different cultures? Do you think about things with slight nuances like the culture in the Philippines and how that differs from the culture in Portugal? Or do you kind of try to strong arm it to have everybody kind of on the same page? I'm always curious how you think about this.

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Ian Jackson

I think for me, and we've just been updating our HR handbooks for the different countries so it's kind of been in front of mind recently, is that we have some core values and guiding principles and they're kind of non-negotiable. That's how we're going to do things. So they have to be seen in operation as we do things in each country. But beyond that, then I think there needs to be a different approach in different places.

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And when you look at even the Philippines, People say it's kind of monocultural. It's not, right. We have a large office in Cebu, which is the third largest city in the Philippines, I’m hopefully not wrong there. But the culture there is very, very different from Manila and our clients who have teams in both places will point it out. They are just very different than the Filipinos in Manila. If you thought Filipinos in Manila like to dance and party, every time there's a show put on and a client turns up there and it's like people spend all their personal hours getting ready and prepping for these things. It's very, very different. 

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Tyler Rachal

They're incredible.

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Ian Jackson

 So, yeah, I think there's that. And also, when we opened up in Portugal, we knew that this was not to hire just Portuguese people because the goal of that office, and the key success of Lisbon, is it's a very, very international city with people from all over the world actually choosing to make it home. And part of the deal is, it's relatively inexpensive, it's the cheapest country in Western Europe to operate from, and it has a very diverse population. So we actually have a number of people. We have an Argentinian working out of there, we have Moroccans and we have Tunisians and we have all these North Africans there as well as our Portuguese people. And it's just, that's how we set it up. It's Portuguese to some degree, but it's actually properly an international office from day one in bed by design.

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Tyler Rachal

Yeah and I'll also bring that back to you personally. I'm curious how your own kind of personal background and core values seep into the business because I think one of the more interesting things about you is the fact that you have successfully kind of reinvented yourself. When I met you, I remember every other sentence was Thompson Reuters. You had this background in FinTech and now I imagine you're probably way smarter about content mod than the average person. 

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So I'm just kind of curious, how did you successfully reinvent yourself? And also, how does being a Scotsman, based in Long Beach, but regularly traveling to the Philippines and Portugal, that part of you, where is that present in Enshored’s DNA?

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Ian Jackson

I ended up in Southern California because we were raising a family in London and our network when we arrived in London was all of our MBA friends. And so we were this very international MBA class and there were seven marriages or something like that from it. And I don't know, I'm guessing there were five of the couples were all moved from Edinburgh down to London afterwards. And yeah, and so I carried on down there in my kind of FinTech world. 

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But when we moved out to Southern California, there was no network for me here. My wife is from here, so she had a network and I had nothing and I had to kind of go reinvent myself and understand how to make the value for my 20 years in working in the city seem relevant to employers out here. And it was hard, you know, there weren't even any FinTechs in Southern California at the time. There were two, there are companies like Equifax, which is more like working for the government. And it just that wasn't a fit for me. It was all ex-military guys and whatever. And so I came out here with very little and I just tried to, I think what you always have to do is, use your interests. Use the things that you were doing somewhere else and then see where that takes you with your network. So my faith introduced me to a bunch of people through my church, that was great. That was good to get a grounding. And I was actually lucky enough as a Catholic to meet some other Europeans, Irish, obviously, stereotype there. But, you know, the two, the first guys I met were Irish. And then, you know, through cycling, I met a whole bunch of people who've, who've stayed in my network since then.

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And then, yeah, just friends and family of my wife and anyone I could meet was just like, get the message out there. But it is really, really hard and you can't underestimate how difficult it is. So I see all these people moving to Lisbon right now and they're the, what do you call them, the digital nomads. That's very different, right? You're paid to work from wherever. You're remote by design. So you're not really doing the same thing as building in a new place as I was at that time. And the world probably looked a bit different in 2012 than it does now.

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Tyler Rachal

Yeah. Lisbon is the Austin, Texas of Europe, correct?

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Ian Jackson

Yeah, yeah, yeah, for sure. And you know, like the different pathway as well was interesting. As you said, I used to just be all about building very complicated products for investment bankers. It was a super niche area. And there was no publicly available information about how they did what they did. But I was trying to build software products and knowledge databases that would help them make more money. And they didn't want to help. My biggest aha moment from the time working with TaskUs was just how open the startups were to ideas, to suggestions, to partnership rather than this kind of confrontational relationship between supplier and buyer, which had been really what I'd seen probably for the prior 10 years. And I would almost say that I had some kind of form of PTSD. I mean  I would turn up to meetings with clients as prepared as we could possibly get. And I was just always expecting that they're gonna find something that I'm not prepared for and they're gonna just beat the crap out of me for fun. And so, working with startups is very, very different. And so, that's how I came into things. 

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And as you know, at that point in the Philippines, I think that the relationship between business owners and their employees was not like it is today. I think people did not expect their bosses to be nice, kind, understanding, highly deferential, very much respect the org chart and don't speak to anybody two levels above you and all this kind of stuff. And that was hard as well. And frankly, that's changed quite a lot. And I think most people will speak with me, at least.

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Tyler Rachal

Absolutely, and I know you've worked very hard to make that culture. We can relate, we worked really hard to build that same sort of culture at Hireframe, but I just don't think people can fully appreciate how hard it is to change when people have had a number of negative employment experiences. It's really hard to kind of rewire them. You know PTSD is actually a very appropriate way of putting a term to it. And you just have to kind of, that, that does not happen through an offsite. It's a lot of very, very small and very deliberate actions over time. And you just have to also lead by example, truly too. But yeah, Mike and I can definitely, we're, you know, I see Mike shaking his head. We've worked really, really hard to get there. So I commend you for doing that. 

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I do want to ask you, you're in a phenomenal, but also very challenging place, in the sense that you're at 2c000 people, you have some really great logos, which I don't know how many of you want to kind of toss out there, but I'll just say that I know them and they're really good. So, I feel like in a certain way you are at a new call it a plateau. And I don't say that in a negative way, but it can be that way, until you get to that next level of growth. As someone who owns a hundred percent of the business and you, your own blood, blood, sweat, and tears to get to this place, what do you think about with, you know, the future of Enshored? Are you thinking I'm in this for the next 10 to 15 years? Do you feel like if someone were to come and offer you a large sum of money, that it would be pretty compelling? And, I know that's a hard question, when Mike and I get this question, I'm always like, I don't know. I'm just thinking about the stuff that is on my to-do list today. It's usually what's on my mind, but I'm going to hit you with this hard question. What do you think?

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Ian Jackson

You stole my answer a little bit, but yeah, there's always so much in the near term, right? So the way I've tried to look at it is my kids are still in school. I've got another nine years at least of that before the youngest is off to college, hopefully. And so I don't need to do anything urgently. I think I still have the energy for it and there are things that I want to complete. I'm more thinking towards it would be nice to have a broader team around about me to take care of things so that I can actually take a proper break, a proper digital detox. Because I remember hearing the founder of GoDaddy, and he just stood down from CEO at that point and he was talking at a conference. And what he said was the first thing he did every single morning was check the bank accounts. And I was like, yup, that's been me every morning for the last 10 years, Saturday and Sunday as well. And things like that are just so ingrained to me at this point that it would be nice to be able to think that I had a team of people who can take care of all of that stuff for me and allow me a bit more distance from that. 

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I think that kind of points towards more, again, some of the current projects we're doing, I really want to right now, strengthen up the global leadership team to get us really ready for the next stage of growth. And we've been thinking about what does an org structure look like for a company with 5,000 people potentially with many more locations. And we're always working on RFPs, and one of the ones we're working on right now as it happens is for a large consumer goods company who needs more European languages than we can likely find in Lisbon. So we're going to have to come up with a creative solution if we win it. And that's exciting, right? But then do I want to be opening an office in Helsinki right now? Do I want to be opening in Turkey? I don't know. So some of this is kind of, there's always like these short-term themes going through alongside the long-term ones. 

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So you set out a business plan, but it's like really what will, what will be validating for you personally? And I think whatever that was, and I probably can't, you know, kind of distill it down into a simple message. I think I have achieved quite a lot, right? I don't think I grew up with any big goal of leading a company. And actually I was quite happy to generally have Jeff do much of the PR and be more of the voice. The first two years that would be definitely the case that he was doing more of that. 

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So I don't know where that kind of leaves me in answering your question, just that I just, I have not really run out of energy for this, but I do have other interests and it would be nice to spend a little bit more time on those. So for this last year, I got a chance to coach, by accident, my son's soccer team just because there wasn't a coach. I've signed up for another fall this year, which is a big commitment because I am going to need to be with my game face on in a public park for two hours twice a week with a bunch of 10 and 11 year olds. And so that's a, that's a little bit different. 

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So stuff like that is good and energizing, but you know, people are always trying to buy the business or they're kicking the tires or they want to. And, I don't really feel any urgent desire to take too many of those calls. It's nice to hear if they have a real thesis around us or whether they're just trying to buy any old company, which it's how a lot of them are. So they don't really know our business. But the ones who do and are thoughtful about it, of course, take the call and see. Maybe we merge together, maybe we do something different. But that's a different path.

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Tyler Rachal 

Yeah, I mean, so much of what you just said resonates. And I think the analogy that I would use is the way that entrepreneurs like us are wired, and the part that is hard for people to appreciate that are not, is your mind is always on  that next rung. And it's not from the sense of you're like, I need to make this amount of money. It's more like, I love that you mentioned the first thing is, you know, building out a proper team around you, right? The analogy that I would use would be people that are working their way up in a sport professionally. And if you love the game and you really are married to the game, the way that you think is you're like, well, I'm right now I'm in university, I'm in college. I can't wait to get to the pros and maybe from the pros, you got to go to the minor leagues. And then even when you're in the pros you're still wired that way where you're like I just need a proper team around me. And then I'm curious, can we win a championship? And if I won a championship, can I win another championship?

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And people are so focused on you want to get rich, which is look, look, anybody who starts a business, you're crazy if getting rich isn't part of it, because it's honestly brutally hard. So you should have some type of reward. But I think that for most entrepreneurs, that only lasts so long. The thing that really keeps you going is I think that opportunity to get to that next level. And then I always say to my wife, I just want to play the game. I just want to play the game and then I want to play the next game and then I want to play the next game. I'm just buying time till the next one. It's kind of how I view it. I don't know if that resonates with you.

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Ian Jackson

Yeah. And I mentioned the coaching thing there in a different context, but the thing that's given me most pleasure through life really has been helping other people, right? I think I'm quite good at connecting and networking for somebody who's a bit of an introvert at times, I do like to do it. I like to connect people. I think about other people. I know that some people are having a challenging time and I'm trying to solve their problem for them without them needing to ask me. 

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But within the organization, just being able to do stuff for our employees, right? In the pandemic, we had a whole bunch of people who were working in travel. We're very big in travel. We actually now have a very large client who I can mention called TravelPerk, they're a Barcelona based B2B travel platform. It's fantastic. Great business. And during the pandemic, our travel clients, we spent two months processing cancellations and then there was no work for 18 months, two years. And we said, okay, these are highly skilled people and they have this salary level and they built a life not expecting a pandemic to come along. So we re-employed them internally and kept their salaries where they were. And actually the Philippines government allowed people to reduce salaries during a pandemic. You were allowed to do that in order to save your business. But we just decided, no, we'll take one for those people and their families and we'll help them out. 

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And that just, stuff like that feels great. It feels like you're an influence in the world and you're making a difference. And I regularly get some feedback from some of our people, you don't need to give us a bonus. I know you've been hardwired in the Philippines to believe that all you get for your labor is your salary, but that's not how as a capitalist, I believe it works, right? If you have an outsized contribution to the team, you should get rewarded for it. And the best way to do that is through bonusing. And so we've built a bonus culture over the past five years and people are still really surprised and delighted by bonuses. And then we find other things as well, just to really make people see the difference between us as an employer and other people. And I think then that comes back to you. My middle management team are absolutely fantastic. And most of them have been with us for a long, long time at this point. I don't have to worry about them. I'm taking care of them and they're taking care of me and it's kind of working. And that's all about culture and having good people relationships.

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Tyler Rachal

Couldn't agree more. You cannot emphasize enough the value of those, I don't care what business you're doing, one-to-one relationships and being able to really impact someone's life that never gets old. In fact, I find it to be quite addicting, to be honest, but, speaking of which, you know, you, I'm going to, I'm going to sort of land the plane here. You mentioned you love helping people. You're a fantastic connector. You're a great networker. Like you said, despite being somewhat introverted,

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If someone's listening to this episode and they're thinking, I got to talk to Ian, what's the best way to get in touch with you? Where do you like, what, what sort of, you know, channels do you prefer?

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Ian Jackson

Gosh, that's difficult. probably email. So just I Jackson at enshored.com. I'm always, always happy to help out. Find me on LinkedIn. Mention the podcast or Tyler or Mike. That's always easy.. And it is for me, that's a huge part of it, because you don't have to do it. It's when you, it's when you really realize you're intentionally choosing behavior and it's not necessarily required right now in this moment for your business. I think some of that stuff really gives me the most self satisfaction and stuff that I don't think everybody is wired that way.

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Tyler Rachal

No, and you talk to talk and you walk the walk. You truly are that way. So I would say that anybody who, you know, if there's one topic, even if you're Mike said it earlier, if you're going through a hard time, I think Ian, when he has the time, could be an incredible person to chat with. So Ian, this has been amazing for an introvert. You sure talked a lot and shared some really great wisdom. what you've done, you'll never say it because you're just not. Honestly, you're not American, so you're not going to just like pound your chest and say, what an incredible job you've done. But I know how hard it is to build the business that you've built. So I'm extremely appreciative of it. And I know that if others knew what I know, as far as your logos and revenue and all that jazz, they would say, wow, he's done a great job. 

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Mike Wu

Yeah, super inspiring.

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Tyler Rachal

So in all aspects, overcoming, you know, incredible tragedy and just, I feel like remaining true to yourself. You're just an incredible person. So thank you for being on What Worked. I hope this influences one person. You actually told us that you listened to one of our episodes and it helped you as you were thinking about making your first sales hire. So that was pretty cool. And hopefully this episode will do the same thing for somebody somewhere out there. So thank you for being on.

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Mike Wu

Thanks Ian.

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Ian Jackson

Yeah, you bet. Thanks guys.

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