Co-Founder | Strategy & Ops Leader | Ex VC & Angel Investor
Mark Dhillon | Co-Founder | Strategy & Ops Leader | Ex VC & Angel Investor

"Because if they create a solution that solves that problem, they can potentially solve a big problem in the world and help a lot of people."

- Mark Dhillon

Mark Dhillon on how he maximized his experience working with various companies.

Talk Takeaways

Co-Founder, Strategy & Ops Leader, and Ex-VC & Angel Investor Mark Dhillion shared his story of how a skateboarder from Ottawa started his first company selling fake Ray-Bans to building his own company and then leading early-stage startups. He discussed how his experience working with various companies in several roles helped him understand how a company scales. In addition, he talked about the importance of being strategic, timing, and KPI-driven. As the last point, he emphasized the importance of building good relationships with the founders, promising that it will benefit both the problem being solved and humanity as a whole.


Builder and Generalist with experience on both sides of the table, as an Operator and Investor. I love creating new products, solving complex problems, and crafting innovative business strategies that navigate untested waters. While I specialize in leading early stage startups (Pre-Seed to Series B), I’ve worked with and advised public companies with $1B+ Market Caps.

• Skillsets: Operational Design and Process Optimization (I Build for Scale), Project Management, GTM Strategy, Strategic Planning (Goals/Initiatives/Resourcing/OKRs), Fundraising, Executive Leadership, Strategic Partnerships, Product Design & Development, Regulatory Risk, Government Affairs

• Vertical Expertise: B2B SaaS, B2B & B2C Marketplaces, Future of Work, AgTech, E-commerce, DTC Brands, Industrial Engineering, Pharma, Venture Capital

The full #OPNAskAnAngel talk

Jeffery: Welcome to the Supporters Fund Ask An Angel. I’m your host, Jeffery Potvin and today we want to welcome with open arms and super excited Mark Dhillon. Thank you very much for joining us today.
Mark: It’s a pleasure.
Jeffery: Awesome. Well the way we like to kick it off and j p right into things Mark is, if you could share a little bit about yourself, your background, the startups you’ve been with, the companies you’ve built, all these great things that you’ve done up to today and then one thing about you that nobody would know.
Mark: Sure, a quick bio for myself. I grew up in Ottawa with a family of engineers. I guess something not really enough people know about me is, I’m a skateboarder. So, I’ve been skateboarding since the age of 10. I still skate to this day. So, it’s very interesting. I worked on bay street skating in the office. But that’s all other than the story. i did a couple degrees in
Engineering, realized it wasn’t really for me, so I did an MBA. That’s how I felt about the whole tech startup world. I started my own apparel ecommerce brand. And then after that, joined like an early stage startup to raise series a and then pretty much after that i joined
the dc arm of canopy growth. so i was a director there and now more recently within the past year, I went to start my own company. That’s still in stealth but we’ll discuss more information soon.
Jeffery: Very cool. And with this brand, company, that you created, how did that start and what got you interested in creating your own business?
Mark: It was like Skateboarding. It is very entrepreneurial in general. Everyone started their own skateboard brands, their own t-shirts and a couple of my friends and myself. We went to Thailand for basically like a winter escape and we started buying all the fake ray-bans to bring back to our friends because they couldn’t afford the actual ray-bans. so from there, they’re just like, why don’t we just start our own sunglasses company. Why don’t we just go on Alibaba, source some different samples, make some simple designs and then sell it to our friends? knockoffs of ray-bans to be honest but we had our own branding. We installed skate shops. so that was the initial idea about five and a half years ago and we ran it for over that time and we had national distribution. It basically gave me the foundation of how to operate a business and manage it.
Jeffery: awesome and i think those things are always super helpful and then you’ve been working with incubators and other venture groups. so it seems like at the same time while you’re building your own business, you’re heavily involved in the startup community as well.
Mark: yeah for sure. It’s always something that’s attracted me. again going back to skateboarding as my base, i was attracted to the big thinkers, the ones who weren’t like
I was really afraid to fail. and I found that same culture and tech. and That’s why I really gravitated towards it and that’s why I’ve been in the middle of it for the past six or seven years. It’s just like all my friends work in tech. It’s something I really love to read about in my spare time and in general too it’s just like you work on really complicated ideas, really smart people. so it’s always exciting.
Jeffery: no that is. and then as you mentioned before, that you went into canopy rivers and a few others like Farm Lead. What drew you to it? Sounds like as you were building through, you’ve got all this great educational background. you started to run your own business, started to run it to go into other big businesses. What learning did you gain from those more scalable companies that you’re able to relate back to this early stage community?
Mark: I think in general, what I wanted was the most amount of experience possible. and joining farm lead at the seed stage and helping them scale, go from like eight employees to 60, was an experience that I really wanted. and I was also working in a generalist position. so it was even better for myself. so those two years were foundational for everything that i’ve done since then. and then on the venture capital side, i just want to get more experience on the capital markets to the other side of the table. It’s like how it looks from tech sitting in a table with VCs? How do they view the world? How do they view the ecosystem? So, getting that really rounded out, like I think , early on in my career, was really important to me. And then I took that to start a company. So, that was like the long-term goal to start a company eventually. And I just wanted to see as much as I could before then.
Jeffery: Amazing. and I like that when you’re just talking about that, you want to see it through the other eye, the other lens that’s out there. and I want to explore that because I don’t think a lot of people take that risk or really understand what it takes to learn what another business is going through. so you mentioned scaling. Then you mentioned the VC venture side. There’s a lot to both of those businesses and there’s a lot to unpackage. so maybe you can talk about that scaling side which is what? did you learn while you were working on a scaling company? because at the time you had built your own company so maybe you weren’t scaling so much on that side. and then you pay into a fast growing company and all of a sudden you’re a generalist and you’re scaling. What does that mean?
Mark: I think in general, it’s just like you’re throwing yourself in the deep end. And you have to do so much in a short amount of time. and there’s a lot of expectations there. so i think it just really bled me from a really young perspective like a young part of my career. but what it does at the same time, it’s like it’s the best amount of learning. It’s like learning times five in most careers. and that’s what really excited me about the early stage scaling. But like most people, it’s like no, it’s extremely hard. it’s extremely hard to go from the pre c to the series a. and once you hit series b, you really have those metrics. you like the product market fit. then you have an engine and then you figure it out from there. but really getting to that point where like your product market fit it’s probably one of the hardest things to this day that i’ve ever done in my career. and I’m consistently trying to achieve that on a daily basis.
Jeffery: So maybe in exploring that scaling side of things, and like you said, going through each one of those stages is pretty detrimental to a company. Can you share a little bit of the hard learnings that you had to take? And I’m sure we can all say it was 20 hour days but that’s probably the hard working side of it. but mentally, what was the business going through and how did you see that shift? because really a lot of companies that we we work with and we all work with in this ecosystem are really early on and they’re trying to figure out, ‘am i scalable?, what does scaling mean to me, like i’ve got a million dollars in revenue? Am I scaling? So how do you associate each of those stages and what does that mean for a company that is scaling?
Mark: i think like, at the very beginning, you’re just trying to find like your power users who really
are your ambassadors and then from there really when you get those, it’s like okay, can i scale this? Can I move it to the next level? And then where are the gaps in our roadmap and gaps in our value proposition that we need to really consolidate our efforts towards to get to the next stage? but identifying that is really really hard and at the same time you also have to get a little bit lucky because timing plays a lot into a lot of this. So I think a lot of startups, when they raise money, they’re on this proverbial treadmill and they’re running really fast towards these revenue targets. and it sucks. And you get it because once you take money, that’s like part of the deal. but at the same time, you also don’t want to be streaming too far through like we need to make more money. or in reality maybe, we should take two months. We kind of build the product and readjust ourselves and reposition ourselves in the market. and i think it’s like two parts to jumping on the treadmill and making sure you’re making the right decisions but i find that most early stage jobs are working really hard but not working smart sometimes. so if i unpackage that in that stage that you came in, commercializing what you’re trying to offer, what it means is that you’re cookie cutting it. so you’re figuring out how we get to packaging this up really tightly. so right now we’re at the top of the funnel. things are pretty open. everything’s hitting us. we haven’t really defined our strategies, our logics, how we want to do all of this, and we really need to tighten that up. so that we can get to a point where it’s cookie cutter. We’ve got the sales team that just understands in and out. this is all we’re doing ones and zeros, one is sail on by is that how you’re looking at this.It’s moving towards, where say you’re like an early stage enterprise SAS company and you got one contract or you got two contracts and you have about say like 250,000 of AR in the door, that doesn’t necessarily have a product market fit. It just means that two big customers really like what you do. but i think really what it is, is like you don’t have to have the repeatable sales process like you said. but you have to find it. but you only really hit that once you have a product market fit where it’s just selling the same story, selling for the most part. or over again, i’ve seen other startups that become almost dev shops to a certain extent. and they keep tailoring the product around different customers. but i think it’s like you said, once you start hitting that conformity in terms of like a sales process, you can start repeating it very quickly, start creating that engine. So I think it’s getting to that point and getting to that point is, like I said, extremely hard. and who’s determining this is this all done by the founder. Is this their team?
Jeffery: because you mentioned that, you took eight people and made them 60. Does that mean you’re scaling because you went from eight to sixty? or does that just mean that you’ve created so much opportunity inside the business that you need more brains running on this? or is it what we really in in order for us to scale the more bodies that are going to bring into this business means that we’re able to adapt, compress, build this, funnel out and really be articulate on where that story is going? and how are we going to move it forward? But is that all founder driven? Is that executive team driven? What’s making this happen?
Mark: it’s kpi driven at the end of the day. it’s like you have to hit certain kpis. you set your ‘okay ours’ for the quarter. Okay, here are the numbers we need to hit. For us to hit these numbers, you have to work backwards. so it’s like, okay, this is the roadmap. The roadmap is going to need x amount of resourcing. so we’re going to need x amount of developers. These are individuals. then we need x amount of people selling. so you create your revenue to headcount ratio. So really at the end of the day, what you do is, you set targets and then you look at your roadmap. and then basically understand exactly the resourcing, put together that strategy and you hire for that scale. but you’re also betting that your product at that point has a repeatable sales process. I’ve seen the other time too where you’re on the treadmill, you raise like five million dollars, you bring a bunch of capital and you’re hired like crazy. but in reality, you really haven’t hit that point where you really need that many people. and one of the companies that i love, Notion, i don’t know if anyone’s ever used Notion, but if you haven’t you should, notions of an amazing all-in-one workspace. but the founder really had this philosophy of only hiring when you need it and only hiring when you start seeing those results, versus a lot of startups raising really fast because they have that network and they have the ability to sell that narrative. but it also gives a negative signal that kind of confuses founders, like, oh, i raised all this money that means i’m successful. It means my company’s doing well. but really, it’s only a resource for the potential opportunity to create for yourself long term.
Jeffery: I love it. I’m hitting the red green button right now. I use both because I don’t know which one’s the best one to hit at this stage. but the stage is lighting up like the sun beam that’s coming through right now and hit me in the face. it’s that button. it’s hitting. but so now you’re taking the scaling side. and the founder, like you said, they’re only hiring when they need to. which i think is brilliant. and it is the way i try to push this with all companies to realize just because you have money, doesn’t mean you got to go spend it. What it means is that you have to be strategic enough to unpackage your business, and then figure out what’s the best next steps to package it all back up nicely and tightly. and then only when you need that resource to come in because you’re overworked with work or opportunity that that person is going to alleviate you. so that you can go on to that next stage. So what drives this out? like i keep going back to this founder’s got eight people on the team. you’ve come on board. they’ve raised some cash and now you’re saying, hold on, let’s put the brakes on here. Let’s unpackage all of this. Let’s figure out what the real opportunity is here and let’s start scaling this. but we don’t need people to scale it. we need revenues. we need kpis exactly. and i think it really depends on the business and how the business is viewed from the founders perspective. if really, like i think, when capital markets got involved in the tech community or whatever, and maybe even 1950s or 60s, when venture capital started really, it became this path to liquidity. so literally, it’s like, oh, you don’t need revenue. don’t worry, you can just go public and you’re fine. and we’ll figure it out later. but i think that mentality is switching at this point, especially what’s happening right past 12 to 24 months is a lot of boundaries. they are starting to move towards that profitability standpoint. it’s like how can we get profitable if we need to get profitable. Can we become profitable and still sustain all the old Harvard that we currently have? But I think what I’ve seen in the past is the previous versus like shotgun raising money. we’ll raise more money, don’t worry. we’ll raise more money. we’ll raise more and burn in as fast as possible where i think there’s this traditional thought process. or it’s like first, to be there versus first to be right. and i think it’s a lot of founders. The founders are trying to be there. First, they want to be the first company in that space because they think they have an advantage. but i think it’s really taking a step back and first of being right. and if you’re selling and your revenue is growing and your user base is growing, even though you don’t have as many people, it doesn’t really matter because you’re on the right path to a certain extent. Then you can figure out when to turn on, basically like pouring gasoline on the light of a fire. so that commercialization component is really strategic and needed so that you can figure out when you’re packaging and take that pause like you said. and you have these dollars. How can I build this plan that says in three years, we’ll be doing 10 times the revenue. but we’re also going to have 10 times the employees. How do we manage all of this? So how do we actually get there? and sometimes it’s slowing it down. to speed it up to process, throw gasoline on the fire now. it takes off because you can throw gasoline on the fire because now, you’ve got a really adjusted strategy that’s allowing you to expand at the right times. And I think, don’t get me wrong. There are startups who’ve succeeded in the other way, where they just shotgun through cash and it eventually just took out the market. but i think those stories are over glorified and they’re the outliers of the reality of the startup world. if you really focus on fundamentals, where you’re focusing on bottom line revenue, you’re focusing on margins, you’re focusing on user growth, and i think you know it’s said over and over again, you don’t have to go raise money as often as possible. and in case, it gives you more time back to your business which is really important. It is the most important thing. I think time is everything. so do you think when that moment side kicks in and let’s just say, you were able to close a round in the first three months because you’ve got strong moment and you’ve unpackaged things, you’ve got a good strategy, you’ve got a good base team like the eight people you mentioned, you just keep scaling, do you just keep trying to bring in as much cash as you can, close more cash, close and then figure out the details along the way? or do you think that that’s a good way to fail and it’s people, are tired of failing? and that’s why they’re trying to look at this process differently.
Mark: i think it’s like, to each their own personally, i really, at the automated day, it’s looking at revenue. and it’s like i’m not going to go raise money until i know we’re on the right path. and
i think really at the beginning of it, again i’ve worked with a lot of earth stage founders. they’re able to raise literally before they leave the job. and they have all this cash and they’re experimenting with it. but it’s always best when you can struggle a bit and really figure out what you need to do. but i think really, cash is only there for you. It’s basically a catalyst for you to get to the next stage and you have to set those stages and set those examples and set the benchmarks. you need to meet and when you’re close to it, then you go raise money. But at the same time, it’s like the ocean’s a perfect example. wonderful story. they raised i think 1.1 million dollars initially, literally used that. I think they had the pivot. The two founders moved to Osaka, I think osaka japan. basically worked in our underwear for a year, redesigned the whole product. I think one of the boundaries took like a hundred thousand dollars. and they pivoted the business and they just built it back on fundamentals. and then i think up until this point, they were profitable and i think during covid, just to give themselves another 10 years rather, they raised 50 million dollars and a three two billion dollar valuation. and they basically skipped venture capital. I think a lot of founders, a lot of angel investors who were in that round, like they skipped venture capital for the most part. and they’re like a huge company.
Jeffery: amazing. yeah. that’s one of the stories that we all want to be part of or at least want to hear about because it sounds pretty exciting. So if you take that initial team that you talked about, can you describe who you would think you need to have on that team to help you with this eight to sixty? what are the type of roles or what are the type of people you think really meet the needs? and it doesn’t matter if it’s sas or cpg or deep tech? are there a couple of key people that you think really will help you better understand and position that CEO and that company for that next stage? I think then, in the day, like it again, it’s subjective to the actual company. it’s the stage and the vertical they’re going after. but the three core pillars. It’s like how much money do I have left, how much money am I making, who’s building the product and who’s selling it. so you just need to feel that that’s it in general. and then usually, i would say you have one smart generalist who’s running across the board.
Mark: I can jump from department to department, but like you’re just building and selling and trying to get to that. It seems like we have a lot of customers now. people, this is becoming really easy to sell. Okay, let’s go build a bigger team.
Jeffery: I love it and when is this key role in this scaling side? Is it a part-time cfo, part-time cto, full-time cto, full-time cfo? like are those roles something you want to fill? or those are still later down the line and you really got to make sure you’ve got that strategist marketing sales roles filled and running at full steam?
Mark: I think part-time cfo’s fine, or controller or whatever. it may be just someone to make sure that they handle the books. people get paid. That’s all that matters on the cto side. depends what business you’re building, if you’re building an ecommerce business, working your shopify, probably not so much. but if you’re building a traditional tech company, you at least want someone who’s leading the technical bill and has skimmed the game. so i always recommend a technical co-founder at that point. or if you’re technically great, you can build it yourself and then you need someone to sell it to. I think someone selling is really important, someone focused on the product full-time.
Jeffery: I love that you said that. and that’s all great advice of course. and it’s huge. I love that you said that having a generalist that can bounce in and out of each grouping. I’m not sure I’ve seen this role yet. So how do you find this? is this a consultant that you can bring in? because i think a lot of these companies that get to this seed stage, they wean between how they get to that series a and they they think they’ve got some market fit, which in your term maybe they’re not really at market fit yet for another raise, but they’re still trying to unpackage it and figure it out. So where do you get this person that has a generous idea of how tech and supply chain and operations is? Is it a consultant you bring in to work with you? Because I think this is crucial for you to get to that next level.
Mark: It depends on the individual. I mean in general it depends on how you see the journal. So maybe someone is really good at design. Someone is really good at engineering. so that could be former journalists, but there’s different permutations of it. but i think if you’re looking for a high level profile in a position, it’s mostly like chief of staff, head of special projects and most likely it’s the traditional background. I think most companies look at it like you have a consulting background. Do you understand some type of product roadmap? something like technology-wise? and will you work hard? Do you want to learn a lot? And that’s it. Usually I see a lot of existential consultants who really want to jump in at the very bottom of a startup. and they go from ending every part of the business. and it’s just up to them to execute on these projects. but I don’t think there’s any traditional profile. they’re really hard to find, the good ones. but if you can get one, it’s great.
Jeffery: I like it. and now you take and slice this up. and you’ve really helped this company scale in the case, the one you’re talking about from 8 to 60 people. That’s obviously awesome. super success. then you’ve shifted into these venture firms and helping with tech stars and coaching and mentoring, so now you’ve got to take in this experience that you’ve gained over that 10 years. he said, yeah, i’m going to use this in a bigger way. and i’m going to start working with more startups. you start expanding out that knowledge. What can you share that you gained in doing that transition? because you went from being in the thick of things. you went from being an engineer to then working at high level execs inside of scaling businesses. and then you’ve kind of gone into that really early stage again, back into that building from the ground up. How much new learning have you shifted into that space? And where did that leave you? What mindset does that put you in now that you’ve hit like three streams of business?
Mark: I think one thing is this, like from both sides, understanding both sides a little better in terms of what they’re looking for, how they see the world. my communication skills at both sides are much more effective at this point. I think also taking the best fundamentals of both sides too. It’s like having the visionary entrepreneur who wants to build really big, but also the investors to see the fundamentals of things like these are five core pillars you should focus on. So I think being able to have intelligent conversations across the board to investors and entrepreneurs and operators has been super helpful, but I think the transition over to the mentoring of tech stars, working in venture capital firm things, like that. it was more serendipitous in nature for one point. it just sort of happened. I wasn’t really looking for it. but i think at the end of that, i was really curious how investors see the world, who they need to raise money from and how angel investors think. I just wanted to understand everything about 80 percentile and then go jump back into areas that I really love but bring that perspective with me.
Jeffery: So what were the five things that you learned that really stuck? like really made an impact in kind of where you are today from the venture side of how they think?
Mark: I think that really at the end of the day, venture capital firms too sometimes, they want to be helpful. but sometimes they’re helpful in the wrong ways. you really want to keep the least amount of distractions to the batteries you invest in. That’s one part. This really gives them value like async. I think most of the time don’t jump on calls too often. I think on the other side too is really there to help the founders and basically like, through hard times, like you’re gonna be investing into this relationship, installation sometimes not gonna go really well. so you really wanna be there for them to be like that open space where they can talk because i find too many times to investors, they don’t have that conversational relationship with the founders and the families. I really don’t want to tell them what’s actually going on. Sometimes it’s hard to tell them that things aren’t working but if you’re an investor that understands, it’s like I’ve been there. it’s okay, just tell me what’s wrong and let me see how i can help you. It builds a wonderful relationship there. and then on the other side too, like yeah, like venture capitalists also raise money from their investors. so they go to family offices, they go to different people, so they have to do the same thing as you. so they typically understand it. Entrepreneurs, associates and analysts are like sdrs. they go out there and source and try to sell. and at the same time, it’s like the managing directors are like the founders. they need to go to these other funds and pitch to them like, this is why we’re gonna make you money. so there’s a lot of synergies I learned. but in general, those are like the three things that really pop out.
Jeffery: no, I love that. and when you’re working with the founders, obviously you came in from wearing multiple hats. which i think is phenomenal. and it really does make an impact to that founder. What did you find allowed you to relate the most was it obviously you learned the humility side as you mentioned, but it was the fact that you really could have them trust you because you’ve done this. you’ve been there so they felt more open to communicate with you versus maybe maybe a lot of the VCs don’t tend to have that side of it. they’re spending their time raising funds and doing all the businessy things. we’ll call it. So did that shift you into that more of a comfort position that allowed you to then bring in that business knowledge and share it easier?
Mark: yeah for sure. and actually my position at the venture capital was actually working with the founders primarily. and i think really, why that was since i’ve been through those ups and downs that i’ve been through, those tough situations may not be exactly in that vertical.
Jeffery: But I understand generally what you’re going through. and I think that is why in general like, that’s been like my piece, where I can really relate to founders because they’ve been through it. but I can also communicate the things they still need to be aware of on the investment side. so yeah for sure, it’s just like you can build better relationships. but i think at the end of the day, it’s like you’ve been in their shoes. like it’s easy to have a conversation about it if you haven’t. It’s much harder and you can tell a good story. You can help them feel comfortable by just sharing a story of like you said when you and your buddies started to sell in and buy products, and have that secondary ray-ban business that got other people excited. because now they’re sitting there listening, go, hey i’m doing something similar. or I’m on this angle. so you can really shift that whole mentality over into making them feel comfortable and sharing problems or what they’ve gone through so that you can help tackle them before they get to the wrong stage of the business which is failing.
Mark: yeah that’s like one of the things i look for too, is even in angel investments, like do i understand the problem they’re trying to solve? How are they trying to solve it? and can I probably predict the problems they’re going to run into? and can i help them with those problems? and I think those are the things I look at as an angel investor. it’s like those four checkboxes there. I’ll probably invest if I like the team but that’s the same way. I look at it as generally like I understand what you’re building, what you’re solving for and probably understand the problems you’re gonna go through. so let me just look away because I spent a lot of time wasting a lot of money doing that. so try not to do it and i can give you the calls, notes and you can make a decision after that.
Jeffery: Well, it’s interesting you say that because from that investment standpoint now, you shift into this newer hat which is angel investing or putting your own dollars into these early stage companies. now you’ve built out this real kpi list that over the decade of learning and building this, you’re like, hey, wait a second. If I’m going to do this, these things have to be met. there has to be these five 10 or 20 things that have to be met. I can now speak to these founders. I can really get into their head. They trust me. I’ve learned this. I’ve done this. so now you shift into that space. How much different is a VC world from an angel world perspective?
Mark: totally different. it’s like not even close to being the same. I think that talking to angels is not like I’m not writing like a person, I’m not writing a hundred thousand or two hundred thousand dollar checks. so i’m just like a little person on the map, but really where it’s like every day, it’s like this. It’s ‘how i can help you and this is how i believe in you.’ And I only typically invest the seed. And really I invest in that level because I find it’s much easier just to find diamonds on the rough of really good people working to solve really hard problems. and i really don’t care what your solution is. it’s like you’re really smart, you’re really passionate, can i help you? It’s one of the biggest things too at the same time. and at the end of the day, will you give up. and you have the ability to listen. and then all that combined, and it’s like they’re just really passionate people, you just put money into them and just like it’s a gamble, but if you bet on them correctly, i think in terms of like, okay, how do you see the world, here see the world Sometimes you can invest in companies and they can do wonderful things for the world. I think as an angel investor, I’m really not doing this to make returns on my money. To be honest, I’m just trying to put my money and just like to give back to the community in different ways and be like, how can I help you? because if they create a solution that solves that problem, they can potentially solve a big problem in the world and help a lot of people.
Jeffery: very well said. I love that. and it goes back to the original story you talked about with the guys that moved to japan. they pivoted and they changed and they had to rebuild their business but you were investing in them. you were investing in those people that were going to have that passion that were going to take the time to figure it out. and if they didn’t, they were going to change it around, get new loans, do whatever they needed to to survive and grow but they were going to take their time to really be accurate on how they’re going to attack that market. and they obviously did it and they’re doing a great job at it.
Mark: yeah. oh well, also i didn’t invest in Notion. It was just an example. i wish i invested in Notion, but i think it’s that scrappiness. Just like Holy, they did whatever they could to get there. i think it was Airbnb, that did like the Obamas, they were selling boxes of cereal to grind and get to the next level. it’s like if they’re willing to do that, they’re probably willing to do a lot more to get where they need to. they’re going to figure it out. I like the approach of having. and you said this earlier, which was that it’s got to get tough. if it doesn’t get tough, you don’t pivot, you don’t learn, you don’t make those changes. if you’ve got too much money or too much of everything, you tend to forget that there’s a hard spot you might not hit, the hard spot at the right time. and then it can obviously potentially go in the wrong direction. So having that and this is what I love about angel investing or early stage investing, is that as you’re working with those companies, they can be sitting there opening up getting all this cash. ‘Come in, they’re working away, their sales are doing okay. they don’t really have a market fit but they haven’t had any struggles yet so they haven’t really hit the wall where they need to really go deep into their thinking to say, hey am i doing this right if i got the right process? Am I selling to the right people? So I think some of that punch that you get as you’re working through really does help you mature as a business and as a founder. It’s like we can’t say too much. we’re building right now but I will invent. but essentially we raised money and we were going to raise a bigger round. but then really me and my covenant took a step back. It’s like do we really know where this is going to go in the next two or three years because we could sell. but like at the end of the day, it’s like do we really know? we’re like, ‘no we don’t. so we raised less money. and then recently probably three months ago, we really pivoted and now it’s really working. but if we raised all that money, we would have all that luxury of like, oh we could throw money at this from any of this. We made a conscious decision to raise less money to put ourselves into that pressure. it’s like if we don’t figure it out, we won’t be able to get out of this. and I’m super thankful we did that. and also a lot of our investors also told us the same. they’re like, don’t raise venture capital right now. we’ll give you money. figure it out first then go raise venture capital. and we’re super thankful for that advice because it worked today.
Jeffery: awesome. no, I agree with that. That’s a great approach to any investor or to any startup. don’t go for the whole kit and caboodle right away. do it in stages and learn because you’re to pivot or you’re going to shift because you need to learn more about what your customers are looking for. and if you’re going to do it on big dollars, then you won’t shift as fast. and you’ll work another day and hopefully maybe make the shift next week. and I think you have to have something that just puts the pressure on you to keep working hard. yeah, and i think again, if you can build a business, not raise money, just do it. It’s intuitive to like the space that I work in and also invest in it. but i think, if you ask every founder, it’s like, imagine, like you could build the same business you had. but you never had to raise a dollar. they would never raise a dollar ever. they only do it because there’s this potential fear sometimes of, i need 20 more people or i need to be there first. or if i don’t raise money, i’m not as cool as everyone else. there’s a lot of these weird like silicon valley ethos that it doesn’t make any sense. but you look at the fundamentals of every great business just like it’s built on money making and making customers really happy. and making sure employees are really happy. and that’s it. That’s great. There is a lot of happiness that needs to happen on that side of it or it’s not going to work forward. So yeah, well shared. So now taking this whole journey you’ve been on which is pretty exciting, you’ve scaled businesses, you’re working for VCs, you’re working as an angel investor. Now you’re going to go and start your own new business again. After all these years, you’re going to go back to the grind or you’ve already started the grind. so you’re back into it. What did you do differently this time than the first time?
Mark: I think I really made sure that I could sell before I built. I think before I was building something and trying to sell it, we started our company. literally, i was selling a Notion template for like two thousand dollars a month. That was it. it was like, i’ll build you a web client if you need it. It’s like, let me see if I can sell it. and i think selling before you build is really key because then you know there’s a real pain point. if they’re willing to like what, we’ll wait a month and a half and two months for this to come out and we’ll pay for it, then they know you have something. so i think that was one of the biggest rules, that stuff for ourselves where we will not start building. And I am frustrated with my code because he’s a developer. It’s like I just want to code. it’s like no, no we’re just going to mock it up and we’re going to see if we can sell this. and i think that’s probably the biggest thing i’m picking so far. and also at the same time, don’t raise money too fast. get down the fundamentals. run really lean and really understand what you’re building. and really have that site where like literally, intuitively, when you’re speaking to someone, it just comes out very naturally. So those are the things I found out about. I’m still learning every single day. so we’ll see what the lessons are in a couple weeks.
Jeffery: ah, that’s awesome. and those are great segues into many more conversations for sure. but those three points, i think really do make a big difference to a founder in hearing that because i will say that if i was to pull statistics off of all the startups i’ve ever talked to, i would say 90 percent of them are builders, from the get-go. and they don’t tend to really get market fit because they think they’re solving a problem, which they don’t realize that a lot of the time they’re solving their own problem which may not always be everybody else’s. so they don’t get that early on traction. I think from the way you shared that you should go out and try and sell this before you actually have a device or product or whatever you have in hand and see if someone’s willing to wait for it and take it. i think that’s massive because it really will get more people involved, more people excited about it and they will wait for the time if they’re really that interested in you solving the problem. and it gives you perspective. i think one of my friends told me this a long time ago, it’s like whatever problem you start with will never be the problem that you actually built a company ever. literally you’re gonna go through like a year to year and a half of just pivots and if you’re lucky, you can get there earlier. But most likely, you’re just pivoting and the only way to really understand where you should pivot is really by talking to customers and trying to sell to them. and they’re like okay, i don’t want to buy it. i’m like okay, why don’t you want to buy it secure, here’s my actual pain point and then you find a new pain point. you’re like oh interesting, we could just move towards that direction and then you start seeing a pattern. you’re like, i wonder how many more people have this problem then you tap into the same people like your colleagues, have that problem and then you see a wide spread pattern. then you start building because you’ve sold something already amazing. so i’m going to take these three bullet points that you’ve gained and learned access to and got all this great stuff along the way and you’ve come up with these three valuable points, you think this is going to be the best company you’ve built because you’ve got these learnings and you think that this is the one that you can really, man i’ve got so much goodness here that i can just shift and change, and i’m gonna see it before it happens. Do you feel that you’ve really got that edge now after all these years?
Mark: I think so. I think at the end of the day, to what it really is, my co-founder has been working together for five years. We’ve been friends for that long so we really know each other well and we’re really in this amazing ability to pivot and understand exactly what’s wrong, like we like being wrong. because if we’re wrong most of the time, we’re actually learning a lot faster. and as we learn faster, we’ll become more and more right. and I think we’ve just really taken a step back. we’re like we could be completely wrong. Let’s test it a lot faster. and i think really we’ve built our team very lean on purpose. but we’re building at the pace of a team of 10. We’ve been talking to a lot of big partners, a lot of big companies and there’s like how many people are you, they’re like four. and you’re like we thought you were like 10 to 15 or like yeah. so we optimized every aspect of it really. where now it’s more like same time, one of the biggest things is like just be ready to learn anything. but sometimes you’re going to have to do stuff you don’t want to do and one of the biggest things too is i had to learn how to design a figma because i had all these ideas for the product and then my my co-founder really just didn’t really understand it. so we’d spend like days going back and forth in terms of revision where I just literally spent every night for three months just learning how to design a figma. Now I could literally design in five minutes and center the team. and then the actual, like changes done within minutes.
Jeffery: brilliant and I love the fact that you’re always learning and not afraid to keep learning and testing yourselves and keep pivoting and changing. i think that’s phenomenal. and it goes to a test all the things you just shared. so amazing learning. The last question I’m gonna or drive into here is you talking about a co-founder. Is this crucial to this business and to any business you build in the future. Will you always have a co-founder?
Mark: I don’t know. That’s a good question. I think this one for sure, definitely. it would not be anywhere close to where we are without him but he’s been a friend and he’s one of the smartest people i know. so it’s a no-brainer. But in general, like I told you, I could start a clothing line in the future. Maybe I just want to do that. I really don’t know. i think i’m not like a cookie cutter entrepreneur in terms of i need to build a sas business. I need to build a marketplace. If I want to open up a coffee shop, I may do that. I really don’t know who I’ll need at that point in time. but i think right now yeah, i would not be able to do this alone. And I think for the most part, it’s not only just the building that’s like, I can’t code and I actually can’t build a product itself but it’s really having that emotional partner you know. i have my partner and he has his partner but really at the end of the day, you really don’t get it unless you’re in the middle of it. so being able to just let off some of the stress and tell each other what’s going wrong, how they’re seeing the world and making sure they’re more comfortable. I think that’s really a core part of having a really great founder relationship. and if you don’t have it, sometimes it may just ruin the business because of two families. Again, I’ve seen it before. It’s like two founders really getting into heated battles. They try to screw each other over but really making sure you have a really great relationship in the middle is really important to every business.
Jeffery: I love it. I love it. there’s investors out there that won’t invest in a company unless they have co-founders. So there is a true model that does fit along with this and I do think it makes a big difference and two brains can do more than one. so i think that there’s a lot of opportunity to see there. So well maybe, we’ll have to catch up in a couple years on this topic because I think it is pretty massive and I think it’s got to be pretty helpful when you’re building a startup.
M; for sure.
Jeffery: yep, again it’s like usually two brains are better than one. and two brains with skin in the game at the same time and passion for the same problem always helps. agreed. awesome. Well, we’re going to transition a little bit now into this heartfelt emotional question that’s based around all the experiences you’ve gone through. and man you’ve gone through lots which is super exciting. is there one story that really stands out to you that really made a difference or something that just blew you away on what it takes to be an entrepreneur and maybe she or he just you invested in or heard of or worked with and it just was amazing to hear and see like man these guys weren’t going to make it and they just totally pulled this off and you know they’re crushing it or whatever the story is, but just something that really proves what it takes to be an entrepreneur?
M; I think Notion. it’s just like i read it and like it just blew me away. It’s like something we tailor our business around. and how they start off, I can take a step back. how they start off, they want to build a note code solution for general individuals who don’t know how to code. and they realized that wasn’t working. They were building it and they took I think the last two hundred thousand dollars, moved to the cheapest place they could go than the co-founder and literally day and night they became the number one figma user and the entire platform early on. and they were just coding and designing coding and designing coding and designing, then they took money from their parents. like imagine all that, you raised millions/ you made a couple million dollars of investors. you go to your parents, ask for more money and you’re sitting in your underwear designing and coding day and night. and like that’s a lot of courage. and then on top of that too, once you start turning that corner, you’re still like, i don’t need more money it’s just risk on risk on risk. and they kept succeeding because they built a beautiful product and they listened to individuals and they went back. I think one of the great things is that they looked at the history of the internet. They looked at the history of technology and really what are the core fundamentals of that culture like in the 1960s and 70s. They took that ethos and put it into their product and built it into a giant and literally they’re one of the most prominent companies today. and i think they’re only like 70 or 80 employees.
Jeffery: amazing! That’s a pretty good story. and I don’t like the fact that they didn’t give up. they just kind of kept tackling it and balanced out the cost. and balanced out the effort to ensure they’re building forward and that’s amazing. yeah, i think one of the big things is unfortunately we’re in a society that really focuses on the end result all the time. it’s always about the end result, how much money did you make, how much money did you do this? like how many employees do you have? but entrepreneurship is not about the end results, it’s about the journey. when you die, you don’t give a that you listed on the tsx or the nasdaq. what you care about it’s like wow, i haven’t hung out with all these three people. We were working in our living room for days. and we finally made it and we built this like the next thing. and then we went there and we went to this meeting where we were working. this billion dollar company had no idea we could pull it off. We pulled it off. like that’s what matters. That’s why you start companies and that’s why you build. it’s for those adventures and it’s for the knowledge and it’s for the memories. Everything else is a bonus. and i think if you can take that mentality. that’s why i think silicon valley is so successful, you see kids who are literally five to seven years old, typically across north america, you’d have michael jordan up there. you have like back to the future michael j fox in silicon valley. It was Steve jobs. it was marc benioff and what they really taught is like just go for it, just try it. because you’re going to be way further ahead than everyone else because you learned really on steroids. but i think if we can start bringing that back to like canada where it’s like, i think there is a lot of a community just where like they look down upon others if they fail. It’s ridiculous because probably one percent of people actually go for it. and when they go for it, you just have to back them as hard as possible because they’re the backbone of Canada, of the US. like entrepreneurship is everything.
Jeffery: So well said. I love it and totally agree with all of that. and it really is being a cheerleader for early stage risk and people that do start companies. I think again, 100%, it’s just putting your foot forward. go for it. Risk is tough to manage but at the end of the day you’re gonna love it. you’re gonna love the feeling of it. it’s up to you. it’s your domain. The only way to succeed is how you keep pivoting. and i love the line because I use it all the time on startup founders and everybody else. But I use it all by myself too. Whatever I don’t do today, I fail tomorrow. so i live the same line that you said that you have, which is i got to put myself into a little stream of where i’ve got movement. because if i put myself into too much openness, maybe i get careless. or maybe i don’t think the same way and all of a sudden it’s too easy, and then i become careless on how i spend or how i operate. so if you operate on this fine line, you’re always going to be pushing yourself to get a little bit further on that line. and that’s what’s going to allow you to feel more comfort. but also drives you. and everybody works a little differently. you got to figure out what your personality is and use that to your upside. exactly and i think everyone has their own path in life, their own vision for what they want to do. but the other day, it’s like they’ll be scared to fail. you’re going to fail a lot in life and life’s going to get harder and harder. you might as well just go with adventures when you can. and if you have the ability and luxury to do it, go for it because it will probably be one of the hardest things you ever do. but also at the same time one of the most invigorating things you ever do in your life. and if you fail, get back on the horse and ride again. man you can do it again tomorrow and start all over. somebody will want to invest in you because you brought the experience, knowledge and understanding of what it takes to be a founder.
Mark: yeah, i’ve heard so many founders i think ii heard a while ago, it’s like we don’t. that’s when you invest and found it the first time. you’re really investing for the opportunity to invest in the third time. and that’s it. you’re just like, i’ll back you, i’ll back you on this one. and probably the third time you’re going to hit a home run. but i’m just going to keep backing you until then.
Jeffery: yep, i love it. I completely agree with that. amazing. all right we’re gonna j p into rapid fire questions now so it’s one or the other ready to roll yeah alright, from the investment side will you invest in a founder or co-founder?
Mark: co-founder.
Jeffery: unicorn or four-year ten exit?
Mark: four-year 10x. actually, no, unicorn.
Jeffery: alright, tech or cpg tech brand? tech ai or blockchain ai? First time founder or second or third time founder?
Mark: first time founder.
Jeffery: first money in or series a?
Mark: first month in.
Jeffery: angel or vc angel? and you’ve got experience on both sides, so that’s cool. I like that. board seat or observer? sports safe for convertible note? say lead or follow equity or interest payments?
Mark: equity.
Jeffery: favorite part of investing?
Mark: meeting founders and their brilliant ideas and their vision for the world in the future.
Jeffery: I love it. number of companies invested per year?
Mark: four to five preferred terms, just typically say post money cap. keep it simple.
Jeffery: okay. any verticals?
Mark: no. It does not pique my interest.
Jeffery: Okay, two things that make a startup stand out in your eyes?
Mark: amazing founders and ability to just like to listen.
Jeffery: I love it. Okay, the last book you read? or not the last book you read. sorry. What is a book that you would recommend that you need to read? That’s a good one.
Mark: “Everyone says the hard things about hard things.” which is a good one too. but one of the books i like is, “Creativity Ink.” So I would say that one it’s “Creativity Ink.”
J; yep, i read that one. I love it. Okay now we’re going a little bit more onto the personal side. So a book or movie? Superman or batman?
Mark: batman.
Jeffery: pizza pop or ice cream bar?
Mark: pizza pop.
Jeffery: five minutes with Bezos or oprah?
Mark: yeah, i love it i’d like to sit down with her. I think she’s a brilliant marketer.
Jeffery: Arsenal or Manchester united?
Mark: manchester.
Jeffery: terrible. I’ve only met one Arsenal fan. This isn’t good. alright. bike or rollerblades?
Mark: bike.
Jeffery: Big Mac or Chicken mcnuggets?
Mark: big mac.
Jeffery: trophy or money?
Mark: trophy.
Jeffery: beer or wine?
Mark: wine.
Jeffery: alarm clock or mobile phone?
Mark: no phone.
Jeffery: hotel or hostel?
Mark: hotel.
Jeffery: king or rich?
Mark: neither.
Jeffery: oh we’ve never had anybody not pick an answer but i like it. alright. It’s good. concert or amusement park?
Mark: amusement park.
Jeffery: fortune cookie or birthday cake?
Mark: birthday cake.
Jeffery: Has life been boring without trump?
Mark: no, life’s never boring.
Jeffery: alright. favorite sports team?
Mark: Ottawa centers.
Jeffery: oh,. you still go back to ottawa. alright. Yeah, alright. favorite movie and what character would you play in the movie?
Mark: Shawshank Redemption. just that one. and I’d probably play the bird. so i can be in the air, in the wall, not gonna have to go through all the mystery they go through, just watch the whole story fall.
Jeffery: I love it. Okay, this is something that’s quite interesting and I will have to unbreak all this data at some point. But I will say that of all the interviews that I have done with this question, at least 10 percent have picked Shawshank Redemption as their favorite movie.
Mark: That’s crazy.
Jeffery: It’s a good movie. It’s very good. It’s the only movie that has been picked more than once. Maybe there’s been a couple of Star Wars movies but everybody has, like a lot of people have picked Shawshank redemption. I actually have it loaded up to watch again. I love the movie. I’m gonna watch it again. but i find it amazing. So many people love this movie. It’s incredible. It’s a lovely story. So it’s why I know why you can share, and if you want, I think at the end of the day, it’s like an underdog story. everything’s at your back. Everything’s going wrong. there’s still an opportunity to live a simple and good life. and you can always rebound from all of it. Yep, agreed. there’s always a way out. you just gotta figure it out. put your head down and make it happen. I love it. the first brand that pops into your mind?
Mark: supreme.
Jeffery: alright. the most famous person that pops into your mind?
Mark: Jeff Bezos, because you just said it. damn it, they’re gonna have to change those questions around.
Jeffery: Ah, that’s awesome. Alright, last question. last question and these were all great. So what is your superpower?
Mark: I think I get along with pretty much anyone. I think from growing up skateboarding and all over North America and weird places, back alleyways, to growing up with engineers and politicians, working with tech executives. I think I can really generally have a good time with anyone and just like to see that life is short. so just enjoy people’s company.
Jeffery: I think that’s about it, Mark. That’s been phenomenal talking with you and I love your answers on everything. Thank you very much for being super open and sharing basically your entire journey that you’ve gone through from startups to big business, to scaling to venture to angels. absolutely awesome. I can see how you are and why you are today where you’re at and I’m excited to see this new business that you’ve got ready to launch. but phenomenal again. I appreciate all your time today. exciting and again awesome answers man. and the way we like to end things is that i want to give you the last word. so anything you want to share to the audience, investors and startups. I turned it over to you but again, thank you very much for all your time.
Mark: I think if you want to build a business, go for it. you got nothing to lose. it’s just if i can get to this point, anyone can. and you’ve seen a lot of people do it but just go for it you’ll never regret.
Mark: I love it. go for it. That should be our new tagline.
Jeffery: go for it. Yeah, I agree with Mark. That’s phenomenal again. Thank you very much for that.
Mark: Thank you for sharing. Thanks Jeff.
Jeffery: Okay, that was awesome Mark Dhillon. he was fantastic. i just again loved the answers, loved the learning, what he did on scaling, the three points that he made certainly about that he’s working with a co-founder and being able to build the business but not taking too much money and figuring out how to position the business that was key. but also going out and selling before even building the company is even more exciting. so all of those little things all make a big difference in starting your business and of course when you go right into it from the investors standpoint, you know from a vc to angel side. Just like you said, it’s easier to come in from an angel side where you’re able to help and work with these founders because they understand where you’re coming from. they bring a lot to the table but you gotta bet through what and how they’re going to bring the stuff that you need into your business. but again these are all little pieces that help you grow and build your business. so fantastic conversation. and again thank you very much for all your time. It was great learning. So thank you everyone for joining us today. If you enjoyed the conversation, please subscribe to our youtube channel or follow us on spotify, apple or stitcher. You can also check us out at or for startup events visit thank you and have a great week.
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