Liam McIvor Martin On Bootstrapping His Startup To $20 Million In ARR By Helping Employees To Work From Anywhere

In the fast-paced world of entrepreneurship, few stories are as captivating as that of Liam McIvor Martin. From a competitive figure skater to a seasoned founder, Liam’s journey is a rollercoaster of experiences in academia, raising money, and navigating the challenges of remote work.

In this episode, you will learn:

• The journey from competitive figure skater to remote work pioneer showcases the diverse experiences that shape a successful entrepreneur.
• The trials of early ventures, including a sporting goods business and an online tutoring company, laid the foundation for resilience and adaptability in the entrepreneurial landscape.
• Time Doctor, born out of a chance meeting and a need for accurate time tracking in remote work, emerged as a game-changing tool, setting the stage for the success of multiple brands in the remote work ecosystem.
• An emphasis on asynchronous management, detailed in “Running Remote,” provides a philosophical framework crucial for the success of remote businesses, emphasizing process documentation and robust technology stacks.
• The compounding power of the SaaS model propelled ventures into exponential growth, showcasing the unique advantages and long-term trajectory of the software-as-a-service approach.
• The foresight into the future of remote work, coupled with the impact of the COVID-19 pandemic, challenges traditional notions of returning to the office, with data indicating a significant shift towards long-term remote work.
• Entrepreneurs and investors are advised to build for the growing segment of the workforce embracing remote and hybrid work models, recognizing the shift in focus from corporate real estate to tools that cater to the evolving work landscape.

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About Liam McIvor Martin:

Liam is the co-founder and CMO of TimeDoctor.com, Running Remote Conference, and Staff.com. After graduating with a Masters’s in Sociology from McGill University, Liam opened a small tutoring company that grew to over 100 employees and looked to solve a problem with remote employees not reporting accurate work data, which turned into Staff.com.

He consults on outsourcing and process design and is passionate about how to gain insights into the inner workings of how people work.

Connect with Liam McIvor Martin:

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• Simple Leadership
• LinkedIn

Read the Full Transcription of the Interview:

Alejandro Cremades: Alrighty hello everyone and welcome to the deal maker show. So today. We have quite a unique guest you know because we’re always talking about racing money and big exits and stuff like that. But today we’re making an exception. We’re making an exception because this founder has an amazing remarkable story. Ah, story where he has had the opportunity of bootstrapping. They’re a company now and they’ve been able to get it to an amazing you know level. You know we’re talking about 20000000 arr you know which is really fantastic for the resources that they had you know, initially going at it. So we’re going to be talking about. Ah, what were some of the experiences in academia you know the experiences too with racing money at the beginning which didn’t pan out the way that they had hoped for as well as getting the initial traction and then also where the world of remote work is heading. He also recently published a very interesting book that we’re gonna be talking about as well. So. Without farther ado let’s welcome Liam Macivever Martin welcome to the steelmaker show.

Liam McIvor Martin: Thanks for having me very excited about getting into a lot of those details.

Alejandro Cremades: So originally born in Ottawa and raised there as well. Give us a walk through memory lane. How was life growing up.

Liam McIvor Martin: Ah, it was okay. You know I had a resident suburban lifestyle so 2 parents that were very happy and loving I actually ended up doing a lot of competitive sports and ended up getting into pair skating. So there’s 2 things that you do in Canada either play hockey or you figure skate. And around 13 I was really interested in all these girls in very short skirts. So I switched over to that and did very well so around the age of 14 or 15 I actually ended up leaving home. That’s why I said it was Ottawa ish where I grew up because I ended up traveling around with the olympic preparation program. That are in various different cities throughout Canada and that was a difficult but discipline building environment for me that I think is so critical for the world of entrepreneurship that I exist in today.

Alejandro Cremades: Now very much a competitiveness now and and an exposure that that gave you know because I obviously as a founder now you know you got started very early I mean we’re talking about 18 years of age when you started your first gig. So how do you think that thing that that world view that I gave you? How do you think it has helped you. Later on that competitiveness as a founder. So.

Liam McIvor Martin: Well I was really kind of almost like an entrepreneur in the closet. So I ended up coming out completely around my early twenty s my very first business was a sporting goods company and I actually ended up selling some pants. And skateguards specifically to protect figure skaters like myself from being cut because I had actually 2 or 3 friends of mine that had cut their arteries and one of them had almost bled out and died. On the ice. So. It’s incredibly dangerous. So I actually ended up developing these products and selling them and this was before really I mean the internet existed but like I built my own website. Um I did everything on my own and that was a great business I ended up actually doing. Pretty good numbers on that one the very first year ended up getting a loan actually that was my first time I ever raised money by the way. Um, which is hilarious so I ended up raising a very small amount of money from the bank when I was 80 x or it wasn’t raising money. It was a loan and I raised 50000 I believe or 100000 and then the very next year I went back to all of those same suppliers and they were not interested in doing a reorder at the same amount that I was purchasing that they were purchasing for them initially. So it was a really problematic issue where I thought I knew my cogs.

Liam McIvor Martin: And then the next year I go back and the cogs get completely obliterated I almost got out of that business with my shirt on I ended up selling it for a very small amount of money and I was relatively successful in terms of my learnings but not very successful in terms of the monetary. Advantages that I had doing it and it was It was a great experience but I would probably say more of a learning experience than anything else.

Alejandro Cremades: But I’m sure that that made your mom happy because as a result of that you went into University So what happened there you know with the academia side of things because it did not unfold the way that you had hope for.

Liam McIvor Martin: Yes. No, so my mother really wanted a ph d in the family and I had been accepted to graduate school at mcgillly university in Montreal and so I didn’t have the money to actually go so I ended up selling the business in order to go and also to just focus me on academia. And I went through that program for about 2 years and for those of you that don’t know most graduate students end up actually teaching first and second year classes and so I got my very first class I remember so clearly it was 300 students beginning of the semester by the end of the semester I ended up with less than 150 students and the worst academic reviews in the history of the department and the department had been running for about one hundred and eighty five years so very bad I ended up walking into my supervisor’s office and I said I don’t think I’m very good at this and he said. No, you’re not and I said so what do you think I should do next and he said well you got to get pretty good at this teaching thing if you want to enter academia so either get better at that or figure something else to do four weeks later I threw a master’spiece under his door and I was out into the real-world which gave birth to my next business which was an online tutoring company.

Liam McIvor Martin: And that company was relatively successful. We actually ended up having hundreds of tutors throughout North America and Europe that would be connected with a student virtually so this was in the days that we didn’t have Zoom or we didn’t have zencast or any of these other types of apps. But it was Skype and it worked at the time and we ended up working with these students primarily for premed prerequisites. So for anyone today still interested in actually running a tutoring business premed prerequisites are the place to be because parents will pay exorbitant amounts of money. To make sure that those kids have a 4.0 gpa to be able to get into the right schools and the problem that I had was I couldn’t actually account for the amount of time that was being spent with these students. So I’d bill a student for 10 hours the student would come to me and say I worked with my tutor for 5 I go to the tutor and say did you work with Jimmy for 10 hours or 5 hours he’d say 10 of course I build you for that I’d ended up having to refund the student for the 5 hours and pay the tutor for the full ten hours this was destroying the business I ended up speaking at a conference called south by southwest which is basically like um spring break for nerds. And I met my now business partner Rob Rossing who had this really crappy alpha of time doctor which is the tool that we have worked on over the last eleven years that could very clearly equate for the amount of time that someone worked remotely for you and you know.

Liam McIvor Martin: Basically at this point now we’ve got a couple other brands. We’ve got staff dot Com which is our enterprise version of time doctor and then we also have running remote which is the largest conference on building and scaling remote teams.

Alejandro Cremades: So then tell us about you know the how how how you guys you know, like really got gotten to work here with the with the company because I mean obviously you had build ah the last one you know to 500 people which is pretty amazing. Ah, and they.

Liam McIvor Martin: Hard.

Alejandro Cremades: It’s unbelievable. You know to think hey you know I want to switch ship. You know at this point at what point do you were you really clear that that was the next chapter for you and and how did you go about selling the company as well.

Liam McIvor Martin: So that actually ended up I ended up getting push out and I won’t tell you the name of the acquirer because there if I don’t tell you the name of the acquiir then I think I can tell you the real nitty gritty details of this I ended up talking to.

Alejandro Cremades: Go for it. Go for it.

Liam McIvor Martin: This company and they were really interested in our online model and they were running an offline model and they were way way bigger than like we’re talking you know they were the dominant force in this particular industry and so I ended up talking to them and they wanted sock to me and they were very interested in how to do online tutoring. And so they flew me down to their head offices I was really excited to be able to talk to them and I sang like a songbird for two days telling them all the details of the business and instead of them buying me. They built a competitor that ended up actually. Taking more and more of my market share away from me and then I essentially went back to them and I said well listen I’ve got no choice here I would love it if you guys would buy the company. They gave me a shit offer I accepted it lesson that I gain from that is recognize when someone is trying to buy you and shut up. As much as you possibly can because the less information that you give them. You need to be able to get your m and a guy in you need to be able to have those those people in place that handle that side of the business for you because from an entrepreneurial perspective I just didn’t understand I was too naive at that point and it ended up you know i. Probably it was one of the greatest fapas of my professional career which was not getting the exit that I deserved.

Alejandro Cremades: I Hear you I hear you you always need that a good and bad cup. No when always see you talking about how beautiful vision and everything is going to be but then always you know getting like you said you know the M and advisorr that is going to help you with achieving the best possible terms on negotiation. So um.

Liam McIvor Martin: Exactly. Um.

Alejandro Cremades: So good stuff and that’s by the way why we do our Pantera advisers now with that being said, you know with time doctor you know you got you got going so how were the early days like for time doctor. Okay.

Liam McIvor Martin: They were tough me and my cofounder we bootstrapped the business but we had a few 100000 that we invested inside of the business and it was a very tough time I remember about 2 years in I I reduced. My personal salary down to and personal salary I wasn’t getting paid by the company at all. But I said to myself I can live on about $40000 per year pretty comfortably so I kind of reset my lifestyle I was in my mid to late twenty s at that point and I said okay I’m going to. Take a couple years off I’m going to learn saas I’m going to learn software because this is the direction that I want to go and this is where I want to take my professional career and 3 years in I had approximately $20000 left in the business. We had a multimillion dollar business at that point which was great but every dollar. We were investing back inside of the business because it’s so important particularly in those early stages every single dollar that you can put back inside of the business and you can turn it into $2 $3 particularly with a saas model. It’s amazing for your long-term trajectory but I remember. Talking to my business partner Robin I said so I’ve got like three months of cash left in the bank I need to be able to start paying myself something so I actually ended up taking a salary first. It was $26000 we could just you know that was the minimum amount that I needed to be able to survive.

Liam McIvor Martin: And then my business partner Rob then took a $26000 salary and we just started raising our salaries by like 10 percent every year which is pretty amazing to be able to see where we are today I was telling him literally a couple weeks ago. Thinking about where we were ten years ago versus where we are today. We never would have thought we were at the levels that we’re currently achieving now but it just goes to show you that Sas has this model of compounding that no other business model in the world can can equal. In terms of getting that snowball rolling and then once it’s rolling on its own. It’s just moving right? 67% of our customer base comes from referrals as a business so it’s a really now very easy business to run but in the first few years it was incredibly difficult.

Alejandro Cremades: And that speaks volumes of the value that you guys are bringing to market. No I guess for the people that are you know are listening to really get it Liam. What ended up being the business model of time doctor and all the different branches associated. How are you guys making money.

Liam McIvor Martin: So Saas Software is a service which essentially means we have we work with a company as opposed to you paying $200 to be able to purchase time doctor for life. You instead would come to us and say it’s $10 per user per month which is our current pricing and. Then you just work on a recurring model and the advantage is that you get the most up-to-date version of the software all the time We’re always constantly updating it. But then the advantage to us is you pay a premium for that and so it’s a really great model because at any point you can quit if you’re not seeing enough value. And ah for us we get that premium for you sticking with us.

Alejandro Cremades: And what about the actual business. What are you guys doing in terms of the actual value you bring to customers I mean what can they expect when they come to time doctor for them to understand that. Also.

Liam McIvor Martin: In terms of.

Liam McIvor Martin: Um, yeah, so it’s a time tracking tool for remote workers and what we do is we measure not just the amount of time that you spent throughout your workday. But we measure the websites and applications that you interact with throughout your workday and this allows you to number 1 be able to figure out. Really interesting insights towards work activity and it also allows you to be able to do a lot of interesting data with regards to artificial intelligence. We can predict when um, you are going to quit your job as an example, we can. Predict when someone is ready to become a manager we can predict with a pretty high ah false positive rate or a pretty low false positive rate. Whether or not, you’re going to be properly onboarded inside of your company. So essentially think about it as like Google analytics for your workday.

Alejandro Cremades: That’s amazing now you guys are doing pretty well ah you’ve been able to build this thing you know, just from like an investment that you and your partner had made initially of literally like a few hundred thousand dollars that you had but you tried raising money and they. And that ended up not working well I think in hintsite you know for for those you know investors when they see that you guys are already at 20000000 plus in a r I’m I’m sure that they’re probably like oh my god I can’t believe we missed this one but why didn’t that you know why did did that not unfold the way that you guys had hope for what. What was missing you know on those capital racing efforts that they didn’t pan out as you had hoped for.

Liam McIvor Martin: Very simply it was a disagreement on vision. So our vision and our mission as a company is we’re trying to empower the world’s transition towards remote work that is what feeds into everything that we do as a company. The conferences that we run the book that we publish everything that we’re doing. And we went around to a few vcs and they were quite interested because we had had pretty successful growth up until that point and every single one of them asked for us to be able to bring not just the founders but the entire team. To that particular location in every single term sheet that we got and we argued with them saying well. Our mission is to empower the world’s transition towards remote work. Don’t you think we should be eating our own dog food and they said oh we love your vision. We love what you’re doing. We love your mission but where vcs trust us. moved to Palo Alto moved to New York moved to Toronto and we just decided not to do it because it wasn’t the right fit for us as a company and looking back on that that was actually one of the best decisions I ever made because Twenty twenty rolled around and just in the. Year of 2020. We grew at two hundred and two percent and it was like monumental growth for us for an 8 figure saas business to be growing at two hundred and two percent is off the charts and realizing that if that had been forty fifty sixty percent owned by vcs.

Liam McIvor Martin: Me and my business partner wouldn’t have the freedom to do what we do today which is we run about 20% ebito we’re able to put that money directly into our pockets as the founders of the business and we’re able to run a a functional business as opposed to a business that’s focused purely on acquisition. Which I think a lot of the companies that raise money I mean that’s the end goal right is to either get acquire or go public and the vast majority that can make it through that process generally get acquired as opposed to go public. So for me I really like running a real business and it allows for us to have a much bigger and deeper remote.

Alejandro Cremades: You were talking about this earlier, you know about vision on how you disagreed on vision with with these folks that when you guys were discussing the financing side of things but to just double double click on that imagine you were to go to sleep night Liam and you wake up in a world where the vision.

Liam McIvor Martin: And most other companies that I see.

Liam McIvor Martin: Oh.

Alejandro Cremades: You know if the company’s fully realized what does that world look like.

Liam McIvor Martin: Um, oh well that was about that was March of 2020 so February of twenty 24% of the us s workforce was working remotely by March it was 45% of the US workforce that was working remotely the month after that it was 67% of the US workforce working remotely.

Alejandro Cremades: Wow.

Liam McIvor Martin: That is the biggest transition in work since the industrial revolution but the industrial revolution took about 80 years and we did that in March completely changing everything that we understand about how we socialize with regards to work and we interact with work if you look at precovid levels Sann Francisco 2% of all corporate real estate was available. Pre pandemic right? in February of 2020 today 23% of corporate real estate is open in San Francisco and that number is going up not down. People are not going back to the office even though you would think and there is a lot of propaganda out there. To be able to say that everyone’s going back to the office. The actual numbers are more people are working remotely today than they were six months ago so we’re seeing this clear shift back to long-term remote work and I’m a very patient guy I’ve been working remotely for 20 years I’m excited about working remotely for the next twenty years so I see us probably being at about 50% of the us workforce working remotely by 2040 and at that point we’ve ah essentially achieved full salinity levels for for remote work where everyone on planet earth. Will be able to have the opportunity to work remotely if they choose to.

Alejandro Cremades: And and you’re alluding to this here but where do you think the whole world of working remotely. Where do you think that’s going you could double click on that.

Liam McIvor Martin: Sure so the last few years we’ve seen a significant pushback to the office and it’s undoubtable that the majority of those companies want to be able to have people come back because honestly. Cost of corporate real estate is very expensive and they’re in a real tough spot right now when you look at the real cost of corporate real estate. It needs to have a thirty forty percent correction before we’re actually at a point where we can continue. We can grow sustainably and move into this next stage of. Work. So I think that twenty twenty four is still going to be a really hard pushback to the office I think by 2025 people will recognize that everyone that possibly wants to be back in the office is already back and then you’ve got the other side of this industry. Which is the people that want to be able to work in a hybrid environment. Want to work remotely even people that are digital nomads location independent workers that move from location to location and want to be able to work that segment of the market is still growing quarter over quarter if I was building a business today. Would definitely be building for that segment of the worker population because those are the people that are going to completely look that’s going to be the growth side of the basically the software world of work is going to squarely be in that side of the camp.

Liam McIvor Martin: And if you’re investing right now in corporate real estate I would not find something else to invest in.

Alejandro Cremades: Yeah, no kidding now there’s probably a lot of people that are listening that are either running a remote type of a company or that are thinking about starting a company and perhaps going fully remote. What are some of the key ingredients that need to be in place to make a remote company. Successful.

Liam McIvor Martin: Sure so I go over this in our book running remote but essentially you need 3 core tenants process documentation. You need asynchronous communication. And then you also need the ability for people to be able to have a technology stack that supports those 2 so process documentation is you need to actually write everything down and write everything down is not the way I want to really say it you want a digital version of writing those things down. There’s actually a lot of really great companies right now that are using large language models to be able to pull out processes from all of your different databases of information from your email from your slack so that you can basically just ask a question like what’s my pto policy and then. Will just respond to you saying your pco policy is Xyz you have fourteen days left do you want to book off next week on your bamboo hr that type of a thing so billing those processes so that managers are not responsible for actually communicating that information to employees and that’s critical. The second side of this is asynchronous management. When I looked at companies that worked remotely before the pandemic. The 1 single thing that they all had in common is something that I call asynchronous management which is the ability to be able to work with people without synchronously interacting with them me and you were communicating synchronously but the people that are listening to this podcast are consuming that information.

Liam McIvor Martin: Asynchronously when it’s most opportunistic for them to be able to consume it so that’s really important part is if you built your business on a mindset of no one actually needs to have synchronous communication in order for the business to succeed. Then synchronous communication is just the cherry on top that allows you to be able to run faster but fundamentally you need those systems in place process documentation being critical one and then the piece underneath it is all of the software and systems in place that you need to be able to operate this so we use tools like. Zana or Jira or Zoom these are tools that are absolutely critical to the way that we operate our business and just by having those systems in place I can say like hey book this podcast off next week because it’s really important to me and make sure that we’ve written up a 2 paragraph intro to intro this next guest and I put that on a sauna I assign it to someone and it just gets completed without actually interacting with that person synchronously.

Alejandro Cremades: So you were you were talking about it earlier. You co-authored the book running remote which came out in August of 2022. So for the people that are listening what are some of the things that they they’re going to be. You know. Able to find on that book in addition to what you were just a mentioning now.

Liam McIvor Martin: Sure so the pieces that I found very frustrating with all of the books that had come out right after the pandemic was number 1 there were a whole bunch of books that came out really quickly after the pandemic like 3 to six months after after March of 2020 so many books on remote work and. The majority of them were crap. They were really bad and the reason why they were bad is number 1 they were just rushed out the door I actually ended up talking with someone who I had never met before in the remote workspace and published a very successful book that had a big launch and I asked this person. Why. I’ve never heard of you and and I know everybody in the remote workspace and this person said oh I was working on something completely different, but my publisher told me hey can you write a book on this subject because if you can we’ll give you two hundred and fifty thousand dollars ah bonus to be able to get this out in six months because we need stuff to be on the shelf. There’s a lot of crap that was coming out there and what I realized was the only thing that everyone had in common with remote companies that were an open before the pandemic was this phenomenon called what I’m calling asynchronous management companies like gitlab run completely asynchronously, they do not actually talk to each other. On a daily basis and so for me I really don’t think it’s about whether or not you use Zoom or Google meet or whether you use Asana or monday.com. It’s more the actual philosophy the managerial framework that you need to go and change in order to be successful.

Liam McIvor Martin: When you work remotely and so for me that was the key differentiator in exactly what I wrote the book about. So if you want to know like you know whether or not you should use Salesforce or Hubspot I’m not the book for you. But if you want the philosophical framework in order to be able to change a management style running remote is the book specific.

Alejandro Cremades: Amazing And if anyone listening wants to hear about this story of a gitlab and how they did the whole remote structure. You should listen to the episode I did as well with the Citysy branddi. So I guess the yeah now for the people that are also listening. You know I like to ask your question because we’ve been talking about.

Liam McIvor Martin: On that.

Alejandro Cremades: You know vision and the future. But I want to talk about the past and doing so with a lens of reflection if I was to put you into a time machine lim and I bring you back in time you know maybe to that moment where you were eighteen years old and thinking about a world where you would start a business Let’s say you’re able to sit down that younger self and you’re able to give that younger self. 1 piece of advice for launching a company. What would that be and why given what you know now.

Liam McIvor Martin: Um, don’t launch a company buy as much bitcoin as you possibly can I Now let’s let me let me think about it Seriously I probably wouldn’t have very many regrets to be honest with you I think that I would probably sell.

Alejandro Cremades: I.

Liam McIvor Martin: Younger self. There’s going to be a lot of pain that you’re going to experience over the next few years however it’s all going to work out and you’re actually going to end up being much more successful than you possibly could have thought you could have been standing there right now at 18 years old but you’re going to have to go through a lot of shit to be able to get there and I think that that’s really the story of all entrepreneurship at the end of the day what type of pain. Do you want to experience if you want to experience the pain of no money bootstrapping a company going slow for many many years before you can actually scale up and build something big or do you want to go to the pain of. Raising money learning how to do that having a board breathe down your neck having the the stressors of everyone telling you you must grow at this rate or you’re not going to get your next round of financing. Do you want that type of pain choose your pain and either direction you’re probably going to have. Ah, very stressful time. But it’s going to be a lot of fun. You’re going to learn a lot of stuff and you’re going to be able to you know in 1015 years be able to have a fantastic lifestyle where you live where you want to live you travel where you want to travel. You do what you want to do with wherever you want to do it with for as long as you want and that for me is just the That’s the promise that entrepreneurship provides to everyone and it’s so important to be able to keep that in mind particularly if you’re that 18 year old person right now listening to this podcast. It’s going to be painful but you’re going to blink.

Liam McIvor Martin: And you’re going to be 40 and you’re going to be really excited about where you’re at.

Alejandro Cremades: That’s amazing. So Liam for the people that are listening that will love to reach out and say hi. What is the best way for them to do so.

Liam McIvor Martin: The best place would be actually going to my Youtube channel youtube.com/runningremote all of our talks are up there for free and if you want to be able to check out all the content there. Go check it out also comment and I will respond. That’s the only form of social media that I actually directly respond. In other than that Linkedin Twitter threads I’m actually having a lot of fun with threads right now. So go check me out there.

Alejandro Cremades: Amazing! Well haleyam. Thank you so much for being on the deal maker show. It has been on on earth to have you with us today.

Liam McIvor Martin: Thanks for having me.

*****

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