"We always like to say we [startups] operate in stealth mode and the first time you’re gonna hear from us, the word we say is checkmate."

- Keith Loo

Keith outlines what he looks for in a start-up

Talk Takeaways

Jeffrey Potvin talks with the “visionary” Keith Loo on his journey as an entrepreneur, investor and mentor. While relatively new in investing, Keith first ventured into angel investing when one of the startups he mentored needed cash. This started the ball rolling and while he might be a little conservative with his investments, for the startups he does invest in, one can expect that more than the money, he puts in his time and energy as well.

The startups he looks for are those who are seeking more than the money. While money is important, Keith believes that founders should also be looking at the breadth of experience an investor can add into the business. He has no particular verticals in mind, he is more interested in the potential scalability of the business and the right market fit.

About

Keith Loo loves scaling businesses. Regardless if it’s a startup, non-profit, or global corporation – he thoroughly enjoys the full process from ideation, to execution, to massive scale.

He is passionate about developing innovation, transformation, and go-to-market strategies that drive real, tangible impact.

He is also a:

  • Proficient technical jargon specialist, including but not limited to AI, big data, AR/VR, ML, and NLP
  • Data & Cloud Computing strategist
  • Skydiver
  • Open Source, Open Data, and Open Government advocate
  • Gamer
  • Start-up, Scale-up, and Keep Going enthusiast
  • Proud Alumnus of the Schulich School of Business
  • Raptors fan

The full #OPNAskAnAngel talk

Jeffery:
Welcome Keith Lou, we’re excited to have you here today. Why don’t we start off by maybe giving us a little bit of background about yourself, where you come from and the things that you do in the angel investment community and world that you are into today.

Keith:
Sure I’m a start-up coach, a little startup, an advisor and mentor. And I really focus on taking high businesses that can really scale and enabling them to get there. And so I’m known for building Canada’s first fractional CTO service and so that was when we really work closely with a lot of investors and their businesses that were perhaps struggling you know after they blown through most of their investments and then we would step in and help them get there. And so after doing that for a few years I’ve really kind of fallen in love with just helping startups grow and so that’s what I do.

Jeffery:
Perfect and is this been something you’ve been doing forever or were you in a start-up yourself and kind of just saw there’s this bigger picture?

Keith:
I’ve always been involved in startups in my career. I mean I had my first startup about 20 years ago back then it wasn’t called the startup was just called a side hustle or just hustling. But I’ve always kind of started even when I was working full-time roles and my startups are making more money than my full-time gigs. But yeah I’ve always been involved in startups but it wasn’t really called a start-up maybe until about eight years or so ago and I’ve had tremendous failures and
catastrophic failures and I’ve had a few success and so I’ve been fortunate that way.

Jeffery:
Okay great well we can talk about all those because they’re all good information to learn from. and hey you wouldn’t be not sitting here, you could be sitting anywhere but you wouldn’t be in the position you are today if you didn’t have the failures and you didn’t have the successes. so they’re all beneficial to who and what you are today right

Keith
Mm-hmm

Jeffery:
So I guess the the first question is why do you invest in startups and why do you have this idea that you need to be around startups? What really drives you for this?

Keith
Startups drive tremendous growth and innovation that your traditional enterprises or legacy businesses just can’t do at the right speed or have the commitment to do it right. Whereas startups tend to take more risk and are not afraid to just do things that are the right way of doing things. and so that’s just a passion of mine and love building businesses and so when I find other businesses or the people that are doing something that is just amazing and I can change the world or that can make a phenomenal amount of money, I would love to contribute in any way I can.

Jeffery:
What got you started in the investment community side of things, like what got you steered into this?

Keith:
So what got me started in investments, and so I haven’t been in the investment game for that long probably about six or seven years. When one of the startups that I was mentoring they really needed some cash to get going. And this was a business that I really believed in and I thought if I
believed in this business that much I should put in money. And that’s kind of what started the ball. And I don’t jump into investments all the time, I put in a lot of my time and energy but where it makes sense sometimes I do that.

Jeffery:
That’s awesome. So when you did do this, did it work out over the long run? Was this part of your highs or the part of the lows?

Keith:
Well the first one was a big high. And so that’s kind of in the domino effect right. So it worked out quite well and is working well and so that’s what kept me involved.

Jeffery:
oh that’s awesome. And you’re right, it’s the excitement, it’s almost addictive – it’s like gambling. so if you find the right mix you’re like ‘I’m in’, and the next one comes too like ‘man this fits the right mix I’m in’, and it keeps domino affecting but at the end of the day you still gotta have the hands on to help and drive in there to work with them. So is there a favorite part that you really love about startups or investing in startups?

Keith:
My favorite part about the startups and the startups that I am most interested in are those that are looking for more than just money. And I think most people, most smart founders realize that money is not the only thing that they need. And I think that’s a major challenge that we find while working with founders you know. I want five million dollars over ten million dollars, I want five hundred thousand dollars and once I have that I’m gonna have the best startup for best business in the world. That’s usually not the case, it’s I need that money so that I can get customers. I need that money so I can build products, right. I need that money for a variety of reasons, and so if you have an investor that can help with that particular thing, perhaps of their network, perhaps their experience, perhaps that’s what their business does. I think that’s where it’s more aligned and so that’s where I usually look for you know, ‘can this startup benefit from more than just my money or my networks money’, and we can really go in, for instance, if we are working with a medical startup and I have investors or my network can really work with these medical platforms or applications I think that would make a lot more sense. So that’s typically when I would get involved.

Jeffery:
Well that’s great. So you’re kind of a visionary because you’re looking at what’s going on in this business right now and you’re envisioning where they should be in the next three to five years and you’re going to say is that if I come in and just give you cash that might get you to here, but if I come in and help you with these things or our group comes in and helps you with these things, you’re gonna get here no matter what we’re gonna help you get to that three-year mark. So you
have to envision it. If you can’t envision yourself getting there then you probably won’t be investing or driving into that company

Keith:
Exactly. I mean and I am afraid of the term visionary because it sounds so grand. I think it’s more just someone who thinks a bit more long-term, more strategically for these startups. And that’s something that — I work with a lot of incubators and accelerators and I mentor quite a few startups and one of the major challenges that we have that we typically see is most often, startups are truly focused on the now. Which is critically important because we have to grow, we have to survive and there might not be a tomorrow. But sometimes we’re so focused on the now that we really don’t know where we’re going to be tomorrow. And so it’s that if we can find the right ones and work with them to think strategically for the long term, I think those are the ones that are going to be successful.

Jeffery:
Agreed and there’s a lot of coaching that does go into that because startups are new. You’re a whole concept of how to run one, how to execute things, it’s learn as you go and if you don’t have somebody to bounce ideas off or share, figure out what you got to do next and solve that problem or the next to problem you’re gonna have cuz they happen every day, then you’re really taking two steps back. And you’re not gonna move forward as fast, if you don’t bounce ideas and don’t think futuristic so I promise I won’t call you a visionary but I will because that’s exactly what you do. Brand as that is, it’s friggin awesome. So that’s a good thing. Do you have a — on your I guess when you’re looking at the portfolio of companies that you bring in and coach that you invest in, is there a number of companies that you look at doing this with at a time per year like you need to make sure that you’re investing in at least two companies working with five and that’s what you do every year or does it kind of vary what’s the thoughts around that?

Keith:
So I typically don’t have a set number of startups that I work with. You know between investments, coaching, mentoring or some that I said on the board on, I’m probably actively working with about 20? But you know in my extensive say hey the folks I want to book meetings once in a while or just check up calls or things like that would probably range is probably 50 to 60 by the time.

Jeffery:
Okay sounds like a lot but I guess in the scheme of things, you’re really diving into 20 solid companies and then you’ve got peripheral companies that you’re looking at moving around and seeing if you’re gonna do something with.

Keith:
Great or if I can you know send them somewhere else where they can get help and sometimes companies just need and I don’t like the when we think about startups not companies – it’s really the founders right, founders just need you know sanity checks once in a while. And I think that’s really what it is.

Jeffery:
Wow that’s awesome. Agreed, agreed. Is there any verticals that you like to focus in on? So if the world sees this one day and they’re gonna reach out to Keith they’re gonna say okay he loves FinTech or he loves this I gotta go after him for this.

Keith:
You know I have a saying I don’t really care if I’m selling toilets or if I’m selling artificial intelligence. It’s not so much the sector that is interesting to me it’s the potential in the scale of the business that is interesting. And that typically and not always but typically has a data and AI element to it but that’s not always the case right it’s just that from my experience it feels like data data-driven businesses or AI driven businesses typically are the ones that can scale the fastest. And so that might be a common theme among most of the business I work with but that’s not always true.

Jeffery:
Okay so do you you dabble in food and retail or those are you like just deep tech?

Keith:
I mean I’ve worked with food and retail and there are very interesting companies that I I do work with right now. But it’s gotta be one that’s capable of high scale, I suppose right.

Jeffery:
Yep

Keith:
Again, that’s just my personal interest.

Jeffery:
Yeah, yeah. No that’s perfect. My scale is good. Verbal agnostic is good too. So it’s just figuring out what the the right little mix is which is good. So now you value tied in, you’re working with the startups, you’re getting lots of information, you’re moving along, is there anything when you’re diving into really diving into the company — from a DD perspective you’re doing your due diligence, is there things that you look for to make sure that this is something you want to get behind? Because I’m sure not every company you look at are gonna be buddies and friends that you’ve got to get in and work with. So is there a process or is there something that you really have to dive into right away in order for you to commit?

Keith:
I mean it depends. So sometimes if it’s a really tech driven startup then of course we have to do a very deep technical due diligence right. And so that does range from you know looking at the products , sometimes looking at the code, sometimes looking at the people involved. But really I think a big part of it is based on the founders. From you mean the founders and the team in my mind, some of the most important pieces of building a successful startup. And so that’s where we focus a lot of the images so getting to know the founders, getting to know you know what their goals are, and how they work etcetera that’s probably part of the most important thing for m.

Jeffery:
So if the founders are the most important piece of this whole startup community and what you’re doing, how do you find with COVID and being the separated side of things and doing things through zoom or whatever it might be, do you think you can still work and invest in a company if you don’t get the opportunity to meet face to face or you’re gonna make that happen no matter?

Keith:
At first I would say the first month or so COVID it kind of changed the investment landscape a bit. You know and a lot of most deals are done with a handshake and probably with a drink the night before. But it’s actually in my mind changed for the better now. It’s a lot less BS and it’s a lot more focused on hey is this business awesome? Are these founders the right people to get it done? Are they right in the right industry? Because I don’t you know have the opportunity to do more of the soft stuff, if I if that means anything. But I find that now I think now that we’ve had time to adjust I don’t think it will slow down anything, in fact I think it just makes things a lot more efficient.

Jeffery:
So kinda just moves everybody into more of a digital space which is what we all talk about and do but now we actually have to act on it?

Keith:
Yeah we actually have to do it. The craziest thing is because I’ve been working in tech for 20-something years and you know when we’re working in large tech corporations and even though they are selling 100% digital products, you know multi-million dollar or hundreds of multi-million dollar deals are always done in person and always requires big meetings with like 50 people. Meanwhile I think now we’re truly actually doing everything digital – which is awesome.

Jeffery:
Well maybe that means that people are actually taking more risk, and they’re making calls, and not having tied 40 people into a meeting. And they’re just saying you know what I have been tying around everybody up even though I may have done it in the office but now I got to get this done tomorrow so I’m just gonna make the call.

Keith:
Yeah

Jeffery:
That’s good so it might be change in the world. Big change and that’s good because I love digital so I’m glad the world’s caught up and open it that way. So in the DD is there anything that you look for on terms or paperwork that also kind of really I guess gets you interested more. Like you’ve done the due diligence, you’re a big fan of the team, you like where they owners go on the CEO, on a term sheet are you okay with the way it structured if it’s gonna be done as safe or it’s done as equity? Is there anything like that you stay away from or that you’re open to?

Keith:
I think I’m open to anything. And again as long as the way that they structured it makes sense right. And the one thing I have to clarify, I speak on behalf of a lot of different investors that I work with, myself I don’t typically put in a lot of money myself anymore. It’s really about the people I work with that potentially do that. Most of the time there’s not a particular structure or anything we’re looking for as long as it’s something standard and it’s not something that you know it’s out of Moon right? Or anything that’s crazy. But I don’t think there’s anything that really catches people, it’s really if the business is awesome we’ll find a way of working together.

Jeffery:
So you have your own kind of preferable terms that you’ll put together or do you leave it on the startup to put this together and then you’ll go through it and just validate it and go forward?

Keith:
We’ll leave it with the startup and then it’s a conversation right.

Jeffery:
Yeah, awesome. One thing they tell I guess people always look at is that because you’re coming into the business, you’re routing everybody up, does this mean you’re leading the round? Does this mean that you’re taking that stance on finding all of the investors so you agree the terms then you go out find the money everybody else is excited for it you close the round Bob’s your uncle? Or do you let the startup go out and find the rest of the funds, like you commit half of it and let them do the rest?

Keith:
Yeah again completely open to how we work together. I mean sometimes we’ve led, sometimes we followed. It doesn’t really matter.

Jeffery:
So you do not have a preference?

Keith:
I do not have a preference.

Jeffery:
I like it. You’re like easygoing person in this stuff, this is amazing.

Jeffery:
In my mind it’s not the money side, it runs fairly easy to settle. It’s you know and the terms of how that money works. I was just in a in a pitch contest yesterday with Schulich and you know you got a start up there that in eight days hey closed two million dollars, right. And were people really picky on the terms or whatever? When you have a great business, you have a great business and we’ll figure out how to work together.

Jeffery:
No pressure. Now I’m curious who this company was that raised two million in eight days.

Keith:
I don’t know if I can say publicly so I’m pretty sure I can but in the case I can’t, I just won’t say it.

Jeffery:
Text it to me after because I feel like I’m missing out on a deal flow now. Okay so that makes sense. Do you have a follow up structure where you’re saving X amount of money to invest again? Or you just keep following the sequence of the next series, the next series, and just kind of tying in the right investment at the right time?

Keith:
No there’s no specific structure as you can imagine it. And I think this is where it sometimes gets a little daunting for startup founders because it feels like there’s so much structure is this the right way of doing things? After my friends and family round is this the preseed, and is that the angel and then is the seed like if it can seem very daunting. At the end of the day I think but the reality of very far from that. It’s hey we’re a startup and you guys are the investors, you’re in our board perhaps and we’re working together and you know we need another 250k for us to get to the next milestone I don’t know what that round is called but we just need money. Right and so when we just work together with them. If it’s a company that you believe in is probably that you’ve invested in then you’ll continue working with them to get them there. And I think that’s… I feel like that’s relatively normal and that’s how we work with people and again it’s not always money, a lot of times it’s hey you know what we’re getting into this space and we really need some help here. Or you know our products are having some major issues or hey we’re getting some you know get some lawsuits (inaudible) how can we help? And so I think it’s just that ability to continuously can work with the Founders on you’re startups.

Jeffery:
Well that’s good. I think that it really leads into the kind of the next point I wanted to chat with you about and that’s on mentorship. Do you find it, I know from a coaching perspective you certainly do. So do you feel that startups should go outside of their norm and find multiple mentors and coaches to help them along the way from day one? How does that story kind of pan out for you?

Keith:
I think they’re just — we have to be careful with mentorship. There’s a lot of mentorship available right. There’s a million and one incubators and accelerators and different networks and so and I think we’re all bombarded with a crazy amount of mentorship and fireside chats and conversations and TED Talks right. I think we really — and a lot of them — most mentors have great intentions and great experiences but often times they could be opposing views of something and it could end up taking a lot of a startup founders time. And so I think the first step is probably making sure that we’re finding mentors or coaches that are a right fit and are aligned with the founders and what they want to achieve. And secondly if they actually have the time to put in to get them there. Right I think for there are some mentors that we would want to have that we can travel half an hour one hour of conversation with a month maybe but in a lot of in the big scheme of things that’s probably not very helpful. Maybe a little inspiring once in a while but in my mind I mentor, coach or someone that can actually work with you and actually you unlock doors for you. You know help you solve a specific problem and that requires a bit more time. And so that’s how I view mentorship I think it’s important to have some but it’s important to have the right kind of mentor and not too many of them.

Jeffery:
So do you help facilitate that? Do you kind of see — cause’ you are now really invested in this company you’re in there — do you kind of look and see okay there’s a problem here let me find the perfect person that’s gonna mold into this and you go out and find them? Or do you kind of leave that up to the founders to go and search around and look for other mentors or advisers that they want to pay and bring in?

Keith:
Yep that’s what I typically I work with the startup to go and find them. Right so sometimes it’s — and it’s interesting again perhaps it’s my network or the people I work with, a lot of the investors, investor friends, that I have want to be supportive and advisory in the startups that they go into. And it makes sense right because perhaps they were former founders and they’ve exited and they’re very successful they want to help the next generation of businesses to succeed and they know that beyond the money it’s what else they can do. Is it the network? Is if the partnerships? is it customers whatever..

Jeffery:
Agreed. And that’s great that you you have a good network of people that you want to give back. It’s tough a lot of people are either on to the next business or maybe they’re hanging out in their cottage in their beach and they’re there for the next 20 years until they snap out of the days that they’re in. But you know, it’s good that they’re coming back ,so that’s that’s pretty awesome.

Keith:
Yeah it’s a, I think this former exited startup founders. Is that the right word? They are often bored. you know sitting at their new homes or cottages and especially with COVID, it’s been a lot of them have been getting quite antsy once and awhile and want to do things – so investing .

Jeffery:
That’s good that you can kind of pull those strings and get them in because it’s super helpful. There’s a lot of knowledge there that could be lost if they don’t get pulled in. So based on the environment that we’re in, you mentioned this earlier actually so I’m not sure that the answer is gonna go this way but because of COVID have you found that there’s been a slowdown in investment side of things for startups? Have you found that people are pulling back and waiting things out or ramping forward and saying you know what there’s deals out there let’s go after them?

Keith:
COVID has changed the investment landscape. I think it’s changed business full-stop. Right so I think definitely there has been a change. And this is just from my experience on what I see, that traditional / legacy type of investors they may have seen a big hit in their portfolio. And they react differently. Some are you know pulling back in terms of you know hey we’ve just taken a bath on the market we have to do things differently and so they might have tightened up their wallets. Meanwhile what I’ve been seeing is a lot of I don’t call smart investors, opportunistic investors ,and I don’t mean that in a bad way. But there are a lot of investors who are seeing that this is a great opportunity to invest. Say you know gaming companies because gaming is blowing up right now, in health related companies because you know it’s more important than ever. There’s a lot of different types of companies that are great opportunities right now and the smart investors are going in. And so it’s certainly changed, but your traditional investors probably they might have taken a bit of a pause but there are a lot of other investors out there who are doubling down.

Jeffery:
And I think that’s a really fair analysis of for sure that people slow down a little bit you know. If they’re invested million now they’re only putting in half or if they were going after a hundred companies they’re going out for 20 companies. Like things have shifted a lot and rightfully so there’s gotta be a way to kind of steer through what’s gonna be coming right. From all the companies that you’ve worked within the past, the companies that you’re looking to work for in the future — is there something that you can kind of say that you know here’s one or two or three things that really stand out for you from all the ones that have been successful that you really would like to port this over to any new startup. So some advice you give and say hey you know what if you’re an early-stage company, here’s three things that I learned that really will make you the Rockstar if you guys utilize these somewhere in your journey.

Keith:
Wow that’s a really good question. So let me let me try to rephrase that. What are three things that I look for, that I suggest in future startups to attract investors? Is that the right question?

Jeffery:
It could be to attract investors or just to be successful and growing their companies. Like really anything across the line, anything that’s gonna make them rock stars.

Keith:
Well I mean I’m gonna sound like a textbook I guess but I mean the one thing is you have to make sure that one it’s the right fi. It’s gonna sound really bad when I say that because this was literally startup 101 but product market fit that’s what we talked about. But it’s critically important that you actually have the right product for the right market. And the thing the one question I ask every single startup is how are you going to defend against people with bigger networks and deeper pockets and more relevance in this space? Or more experience in this space? And the startups that can come out and truthfully answer that question in a strong position are the ones that are going to succeed. Right and so we are going to for instance, we will defend against you know hey the Walmarts are the world coming in to do this because we are a new retail type of company by doing X Y Z and we have this in our back pocket. Or we have this specific thing that no one’s done before or that we’re doing very differently. And this is not something we’re talking about, this is something that we already have or money, or already doing. I think that’s something that’s critically important right that’s pretty much a number-one question. I mean I build business as I build startups for a living, so what stops me if Keith was a very evil type of investor and I saw that you had a great idea why can’t I just go out and build that I had them one year of the experience and I have the people could do it. So if you can defend that to me if you can argue against you can do that then I think you’re the right company.I think you’re smart company.

Jeffery:
No I like that. Yeah you’re defending your I guess your product, your honor make sure that you know how it’s gonna move forward and if that’s done through IP or it’s done through contacts in certain markets or its focus. There are a lot of things that really tie in to that uniqueness I guess and your ability to really hone into how you’re gonna be successful in that market, so I like that you phrase it as more of a question and a way of getting them to defend their thesis if you will on why they’re gonna be successful and how they’re gonna get there.

Keith:
Yeah and let’s not forget that it’s not so much just a Q&A, it’s more about really — because you learn about that business that way right and it’s really important and that’s you know a lot of times are so focused on building most awesome widget in the world and we don’t think about if there’s someone who can build it better than me.

Jeffery:
That is the case. Yes you’re right or that big business is already in the same process of building it yeah I was on a call this morning or it was podcast? I can’t remember where it was but what was occurring was the story on Microsoft and what I found fascinating about it was that when Microsoft first started off, nobody believed that they could be anything because no one believed that the change was worth going into. No one wanted a desktop computer, nobody wanted a mobile phone so if you as a start-up, you can go under the radar because you’re doing something that’s revolutionary but you’re being quite enough that people aren’t looking you as a threat because then when you do turn on the threat meter that’s when everybody else starts to panic and what I’m seeing a lot of in the last few years there was a lot of everybody’s an entrepreneur now but then in the last year that’s shifted. A lot of people are like you know what this entrepreneur thing’s too hard and now the ones that have stuck it out they’re looking under the radar and they’re thinking how do I get into that market? How do I really make this dent and then turn on the valve and let people know that we’re here so then it’ll start to feed itself. So I think to a lot of your points on how you’re really solving this problem which is how do I defend my business – well I think their big thing is how do I create a funnel that eventually the next two years people are coming to me I’m not going to them. I don’t want to always have to go and sell to everybody but if I could do this right at the beginning, people are gonna be coming to me to find where this problem is that I’m gonna be the solution.Right and there’s a lot of just like the Microsoft story I’m gonna secretly get out there when I turn the funnel on they’re all coming to me because we’re gonna build something that’s fantastic that they’re all gonna be herd mentality and they’re gonna want in.

Keith:
Yeah and there’s a saying where you’re a lot of startups they operate in stealth mode. Right? And it’s not always the best option for starts, it depends, but we always like to say we operate in stealth mode and the first time you’re gonna hear from us, the word we say are checkmate.

Jeffery:
I like that so we’ve got to gone through this nice little journey. You’ve done all your information deep dive, working with the owners, coming up with the term sheets, find the investors, everybody’s ready you’re all in, you’re working with the teams – is there something else that you bring to the game to help the startups outside of just say funding and coaching? Is there other things that you really try to put them through is there like a package, like an eight week program, or is there anything that you do or you guys do that it fits just outside the box but really helps these startups move through?

Keith:
So speaking about stealth mode and I suppose this is the first time that we’re gonna say it publicly, but we have built an accelerator out of what we do and so again we don’t, we haven’t publicly shared this with anybody at least not yet but that’s essentially what we do. And our methods are slightly different right so we would put in a fractional CTO CMO CFO you know whatever it is that the startup needs to go and help them succeed and get them there. A lot of times when we’re building a business we probably have two or three co-founders or two one or two co-founders and it may be a small team of one or two or three people. And so you’re they’re typically product focus and sales focused as we are building our first business. And so we will surround that team with our team to get them there.

Jeffery:
No that’s awesome

Keith:
And that’s what we would do.

Jeffery:
Yeah well those are a little just a little bit of extras that you throw in there so that’s not a bad thing I guess it would help.

Keith:
But I mean it’s a lot of times people don’t think about their finances and it’s really important. Right? I mean hey itss do I have money in the bank account as what a start-up typically thinks about. Right but are we planning of the business the right way? Or are we going to market the right way? A lot of times its if we build it, they will come. No that’s not true whatsoever. Right and every business in the history of time has learned that lesson. And so but we don’t think about it. We think about building the best AI platform that’s ever been created for supply chain but that happens you know how often I would hear that statement we have the best product in the world when it’s out there it’s gonna be amazing – not true whatsoever. How are you thinking about your channel partnerships? How are you going to get your first few customers? Well, how about well if we haven’t thought about it then let’s not just think about it now let’s execute on that and let’s go and do it together.

Jeffery:
And I completely agree with that. And over the years that we’ve found these little loopholes as well. I’ll say loopholes words lack of focus because 98% of all startup founders are builders they just want to build they forget that they gotta sell. You happened an amazing product that nobody uses is a waste of time and effort, money, so you really got to find that sales side of things and understanding where you’re going after the verticals and get in there. So we started to and I won’t we’re not a accelerator but are but we started to hit roadblocks and when we hit roadblocks you create different things so we started off by doing partials on software side which is where we have HardBoot and we provide resourcing to the startup to build platforms but that’s really early and then we created a new one recently called Kashmir which is structured around the accounting and bookkeeping because so many companies we go to invest and they’re like well we don’t have any of this, you’ve never filed taxes, and you’re like wow how did you get this far without any of this stuff? How do you know where your finances sit? So we thought you know why don’t we help that because we know that finance is a tough situation period. But why don’t we figure out how to help that so we created this arm to take care of those things and it’s not because the startup doesn’t need them or that the company doesn’t need to focus on them. The founder should 100% be focusing on these aspects especially the money side of things but it’s helping them educate them and move them through the system at a more effective cost rate so that they’re burning the money on growing their business and there’s a point in time where they are going to take some of this back over and they’re gonna bring it in-house so why not help them leverage more of what they can to grow faster and with your CFO, CTO, CMO, offerings I think that’s amazing because those are exactly the types of extra tools that they can utilize. But it’s also the people are coming in are more senior. So they’re not just bouncing their idea off someone that’s worked on a brand project once in their life, working with someone that’s worked on 400 brand projects and they really know what they’re doing.

Keith:
I apologize I’m laughing out loud literally. I think one of the problems or one of the challenges we see in not only just startup mentorship or advisory, now I’m going to sound like a hater, but also in say fractional support you know is that just because you’ve done marketing in a bid for twenty years it doesn’t mean that you’re great marketing mentor for a start-up or a coach or CMO for a start-up in FinTech right? You have that experience which is awesome but a start-up and the RVC are two different things. And so you know that’s one of the typical challenge that we see in. And you bring a great point – do the people supporting you have a breadth of experience in a variety of different things and also in your particular field? And I think that’s what makes a great advisor mentor culture or staff member.

Jeffery:
Agreed and I think it’s also making sure that the CFO or CEO also knows this is their company they have control over it and they manage everything. But the more people that have knowledge and experience around you allows you to move quicker faster more nimble and move through things and I think once you realize the you’re not the smartest guy in the room or the smartest lady in the room that you’ve got some really good people around you. You’ll find that things just move so much easier quicker faster and they hopefully will protect you from the outside elements of crazy and they’ll help you move through that faster too so I do really appreciate that.

Keith:
And you know I strive to be the dumbest person in the room and I really do mean that. Like if you, if when you’re building a company and you are bringing in people who are better than you at just about everything else, I think you’ve done the best job. That’s what you want. We’re here to build a business right. a start-up is a business and for our business to be successful we need to have bright people. And so if we focus on the business as opposed to I the founder then if you look taking a step back then I definitely want to hire people who are better than me at just about everything. So I think people that can do that are going to be more successful.

Jeffery:
I like it. So to top on that success thing, now your startups have kind of gone out in the world they’re working away, you guys have helped them get to a couple million of MRR or ARR and everybody’s happy, is there anything that let’s just say if we were to share one awesome story that you could say that this startup was oh my god I can’t believe where they’re at, what they’re doing all wrong isn’t working and that they came out on the top and here’s where they are. Some amazing heart felt story that you could share that really just emphasizes what it’s like to be a startup or what people may go through and just add that element of excitement or surprise or just something crazy random story that pops in your head that you’re like you know what I got to tell this story because people are gonna love it?

Keith:
That’s a very good one. I mean I have a million stories I can think of. And you know what a great story that I’ll tell just because it’s a startup that I’m working with right now, I was one of the first investors and I actually worked with them part-time now. But this company when it first started it was you know think about back in the — are you familiar with the company called future shop?

Jeffery:
Future shop? Yeah.

Keith:
Okay just not everybody was I got the story

Jeffery:
I’m like yeah future shop okay

Keith:
So future shop you know closed down years ago. Was bought by Best Buy that’s fine whatever right. And Best Buy decided to lay off most of their senior staff and keep some of them. And this one startup that I’m working with, the founder was a general manager for their flagship store and what they saw was you know what Best Buy is laying off all my people that I helped them for years. They were keeping me but they’re laying off my team and there’s hundreds of people just from his own store that’s going to be unemployed. And so instead what he decided to do was he built a start-up that could employ all of them. and that was a pretty grand vision because that store was a multi multi-million dollar business and you’re gonna go build a startup that’s gonna try to employ all these people and you know that was I think about five years ago something like that. And it’s been a long road in in terms of the startup journey of building the right business and pivoting and it was a two-sided marketplace at first, and now it’s a SAS platform but we’re at the point where it’s grown, it’s scaling and it’s going global. And he has realized or is on the journey of realizing that dream right. And so some of his former staff now work with him in his startup. That’s a highly scalable data and AI platform. And it’s about hiring helping other people get jobs and so it’s one of my favorite stories because this is a story of someone who literally went through the you know learning everything and having to grow and having to scale and pivot and now they’re actually going global and it’s — I love it.

Jeffery:
It’s amazing.

Keith:
Great experience

Jeffery:
That’s a great story. Yeah those are the best ones and he’s gonna have a better story when it does go global and he gets to do that first interview, worst ten thousands interview and he’s gonna go tell that story that he went from being having access whole team to be hiring 50% of them back. Yeah, I think that’s exciting. So he’s a true GM he really took care of his people so that’s pretty exciting.

Keith:
Yeah he is a great guy and just really happy for him

Jeffery:
I love it. So we’re getting close to the end and obviously totally enjoyed this conversation so now we’re gonna do the crystal ball thing and I need you to kind of and because you are visionary and I think this fits just perfectly well in your wheelhouse is — what do you see in the next 12 months in the market and in general and then where do you see everything going in the next three years? So I guess 12 to 36 months how do you see the investment community in start-up worlds kind of colliding in the next 12 to 36 months? Is there an area focus? is there some crazy new tech that you can see unraveling? What are you kind of envision over the next 12 and 36 months?

Keith:
I’ve seen investment in data, AI, blockchain, and healthcare, these are the four that have been accelerating over the past few months and I don’t see that slowing down. I really think that’s going to continuously accelerate because healthcare is absolutely data, a data in AI is something that I assume is going to be everything right. So these are things are going to be watching. I don’t know blockchain, I don’t know. But these are the four areas that aren’t accelerate. And so and you know because of the the issues were having globally for a lot of different reasons know the transparency in blockchain is quite important so I can see that. And so these four areas in my mind are going to continuously accelerate and investors are going to be doubling down, tripling down whether that is 12 months or 36 months. I think it’s just going to continuously increase. We are now seeing what’s important I think it takes the world off you know burning, getting sick for us to realize hey we have to invest in transparency, we have to invest in health right, we have to invest in privacy knowledge right and so these things are happening. And so the smart investors will be continuously doing them. And so that’s that’s what I predict and I don’t think it’s gonna slow down.

Jeffery:
That’s awesome. And it’s funny everybody says the same thing about blockchain and like it’s going crazy but it’s going so it’s out there. Something’s happening with blockchain I don’t really know but it’s such blockchain and and crypto currencies they’re kind of fitting in this bucket where what’s really happening and is it is it gonna take off is it just kind of sitting in the sidelines someone’s trying to figure out though what to do with all this. But I certainly do agree that AI and how that data is big it’s happening everywhere always will people want that data. And healthcare it’s taking off even though right now I think they’ve had some 50% reduction in broken arms and legs and other issues that people have been facing because no one’s doing anything. So I think they want to ramp the world back up because surgeons are bored they’re sitting at home wondering who they’re gonna do surgeries on if nobody’s out being active so I think that there’s gonna be a shift back again and there’s probably gonna be a mask raised for Hospital lineups to take care of those types of things but there’s certainly room right now to make so much impactful changes in how the healthcare system works for being able to push people in and out of being taken care of and I think one thing I’ll add on the healthcare side is I really think there’s gonna be a big big big push in the mental health. I think a lot of people are really starting to learn more about what types of things they’re going through and I think this pandemic has helped people realize that maybe they’re in this alone and they want some help or there’s other problems. So I think there’s gonna be a few things that will really float to the top. But I love the I love the four, they’re fantastic.

Keith:
And you know just to add to what you’re saying and just as literally my experience right now, I’m finding that the medical communities because we’ve really talked about your surgeons.. Yeah, they might be, they might not be as busy as they normally are right now but they have become investors and some of them have traditionally been investors right? They’ve been investors surgeons making money and so you know they have probably always been investors but now that they have a bit more time on their hands they are looking at other opportunities to invest in. And it makes sense that a lot of our medical applications right it doesn’t always have to be but so I’m literally seeing this daily right now.

Jeffery:
Agreed. I interviewed two weeks ago a doctor in Sudbury. That he’s been investing in phenomenal the conversation is awesome just because they had so much interest and a lot of it is on the medical side and they get the tech to get where it’s going but they see the application to it right . Their there. Those things they can figure out where it’s gonna fit. Yeah I can work with this.

Keith:
So it made sense yeah that’s the best type of investor you want they’re smart they understand the industry

Jeffery:
Exactly. Yeah I well to end this off is there any one last advice you want to give to a start-up or to investors, anything you want to throw out there? Keith the floor is yours.

Keith:
Thank you. I think money, is as someone who’s a serial entrepreneur, money is important I get it. I have spent the majority of my startup life chasing money. And I totally understand the importance for a start-up to land that in for an investor to deploy I think what’s important and that we often forget is that it’s we need more than just money. And so as a start-up make sure that you find an investor who can really give you more than just money. Is that their network, is it the support, is it you know the clientele, do they have a go to potential partnership with one of their businesses who knows but that is much more important than just print money. And on the other side for investors yes it’s important to make sure that we deploy our cash and oftentimes especially most people in Canada, traction is the most important word and if you don’t have traction I’m not interested and I think that’s a very short-sighted view in terms of looking at startups. Because the typically, the most innovative, the ones are going to grow, the ones are going to change the world, change Canada at the very least, that they might not have traction right now and that’s okay. And we need to give them a chance and we have to make sure that we do our due diligence and find that they’re not wasting our money but find the right companies, bet on them even if they’re not where you other investors would have liked it to see, well like to be right now. Because if you make the right bets, you’re gonna build amazing company.

Jeffery:
I love it. Well you heard it all right here from Keith. You’re a good man thank you very much for sharing that I took my notes as I do look..

Keith:
oh wow

Jeffery:
That’s what I’m doing, I’m writing everything down man I got to make sure this stuff doesn’t go anywhere but here and then the video and everybody gets to see it. So I’m a big fan. I love it, make the bet and go after it. You’re bang on that’s what people need to start thinking about. it’s not always about traction, its futuristic. And you totally are visionary man. Go with this. Even your three things you just talked about you’re like this make the bet they may not have this this and this but make the bet — that’s a visionary, they gotta see where it’s gotta go. I love it

Keith:
I’m gonna put visionary in air quotes on my LinkedIn.

Jeffery:
I’m gonna put it on my LinkedIn. (Inaudible) quotes.

Keith:
This is a pleasure ear and it was really fun chatting with you

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