321. Solo Capitalist Firm Building, Supporting Founder Mental Health, and Navigating Board Dynamics (Matt Cohen)

Matt Cohen of Ripple

Matt Cohen of Ripple Ventures joins Nick to discuss Solo Capitalist Firm Building, Supporting Founder Mental Health, and Navigating Board Dynamics. In this episode we cover:

  • What led Matt to start Ripple Ventures
  • Solo GP’s vs. Firm Building
  • The Toll of Rising Valuations and Remote Work on Founder’s Mental Health
  • Trends in the Canadian Ecosystem & More!

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Transcribed with AI:

Matt Cohen joins us today from Toronto. Matt is founder and managing partner at Ripple Ventures, a Canadian tech investor. He has made investments in Rose Rocket Voiceflow Marpipe and Lula amongst others. Matt, welcome to the show.

Thanks for having me, Nick. Excited to be here.

Of course from one podcaster to another. I’m excited for this episode. You know, feel free to take over at any time. But, Matt, tell us about your background and your path to VC.

Absolutely. Yeah. So before getting into traditional venture, I spent over a decade working in traditional capital markets and finance, working for RBC Royal Bank of Canada, Toronto and then down in New York on Wall Street, covering global hedge funds lived during the crisis, pretty exciting time in my life, but really spent a majority of my time focusing on the public markets, you know, understanding risk and understanding hedging strategies and public market exposure. And volatility. I never really had any experience in the private markets were really nothing in the you know, venture capital or private equity scene at all until I started my first tech company in 2012. When I moved back from New York to Toronto, a company called Turnstile Solutions. It was an early stage marketing analytics company for using Wi Fi systems to help brick and mortar retailers understand how to leverage their guest Wi Fi networks. And so I wrote the first check to get the company started, we ended up growing the company to about 50 employees and eventually sold it to Yelp in 2017. So I learned from an early time how to bootstrap a company and get it to a successful exit. And eventually, after making a dozen investments myself as an angel investor along the way, and spending some time working in Boston for another startup, I was asked to launch a venture fund by some family offices back home in Toronto, New York. And so that’s how ripple ventures got started in 2018, with our first fund of $10 million. 

When did you first start considering maybe doing this, you know, professionally as your angel investing?

Well, you know, the thing that I really was struggling with as an angel investor was that couldn’t get any attention, if any of the founders out there, especially some of the sought after MIT and Harvard founders, when I was living in Boston, you know, MattCohen@gmail.com, just didn’t work. So I had to come up with a brand and somewhat of a platform to really get in touch with these founders. So what I did was I created a website, RippleVentures.com, LinkedIn page, a crappy logo and Vistaprint card, and just started like pounding pavement hustling my way to meet a bunch of these founders at incubators and accelerator programs in Cambridge, and then realized, you know, I needed to have a formal fund structure, one to deploy more capital and to to really build a brand and a platform for founders to trust me with when I came in with just capital.

Yet, you know, sometimes I think back to the early days, 13, 14, 15. And it’s amazing that we got into the deals we got into like, we were running small checks as angels. And then we had an angel group on AngelList, we could never give a founder like a real number. Well, it’s gonna be somewhere between 150 and 250k. And playing that game and that whole dance, it’s just remarkable, we actually let some deals and get them done.

Absolutely. I mean, there isn’t a lot of big VC funds on AngelList, or a lot of these rolling funds around to because if you’re on AngelList, and there’s deals out there, you actually got calls and had conversations with interesting founders. I remember the first deal, one of the first deals on AngelList that I met and passed on, and still regret to this day was a company called all trails, I didn’t really believe in the community aspect and the value of like having a hiking app on your phone. But little did I know, you know how big of a success it would be. But just like that, you could get some really good at deal flow, just being an angel investor.

We all have some of those. So, but what do you think keeps you up at night? Is is it the sins of commission or omission?

I definitely always remember the ones that I screwed up on and passed on for sure. It’s the ones that you invest in, that have many reasons why they went wrong, that I don’t lose too much sleep over. But I do lose sleep over the ones that I had a chance to make a bet and did not really believe what the founder was saying or thought the outcome would be as large as it ended up being.

Yeah, it’s pretty common in this business. Yeah, you have to miss on some. And if you’re not, you’re probably not seeing enough. But you know, tell us more about ripple. What’s the thesis? And what do you guys invest in?

Yeah, so you know, when I started the fund in 2018, what I really wanted to do was go through the same journey I went through with turn saw my first company, but obviously with early stage founders who are just not getting the attention from some of the larger global venture funds to help them through those day to day journeys of building and scaling their early stage companies, as we all know, you know, one in 1000 make it through to like the series a range. And there’s that Death Valley that a lot of companies unfortunately get soaked up in. And so what I did early on was try to help founders understand like there was investors out there to support founders on the day to day problems they were facing and given my operator experience and investing experience. What I did was we set up an incubator space in downtown Toronto called the tank, and we brought our companies to work it alongside us on a day to day basis. So we brought in fractional CFO to take over their bookkeeping Bing PR and marketing support sales, playbooks partnership strategies, people around the ecosystem to help support our founders. And we want to be known as their first call whenever should hit the fan. And that happens often. You know, a lot of people talk about all the big splashy headlines you see in TechCrunch articles. But it’s the day to day stuff that founders are really looking for help for that we want to be their first call for. And so that’s what our goal is at ripple is to be the first call for founders, whether they’re going through personal or professional problems in their company building. And so we can help them guide them through some of those troubling times to get them out of the Death Valley and onto a strong path to series and beyond.

Awesome. And you guys, are you leading deals are you co investing in combination?

Yeah, so we run a pretty concentrated portfolio and fun one and fun to both return million dollar funds. And we typically lead most of our rounds, I’d say we’d let almost 70% of the deals do co lead. And we’ll also write follow on checks as well. But we do have a preference to lead or CO lead. And that’s just because we like to have a hands on approach and operator first approach to building with companies. So we’re usually on the board, or at least a board observer, check sizes range from 500 to you know, 2 million at the pre seed to seed stage or seed plus these days sometimes, but in our third fund that we’ll be announcing soon, there will be writing a little bit more early stage checks, co investing and helping companies mature. But we don’t always have to be the lead investor.

Got it. I wanted to kind of touch on some areas of your model and just models in general, of course, there’s sourcing there selection, there’s poor, right, you got to find the startups. So you got to choose the right ones, get into them, and then figure out how to amplify their success over time, right and support those companies. You just mentioned having a hands on approach with your model. Tell us more about your support function, like how do you work with the founders? What do you guys do to kind of help them get from that sort of early exploration phase to product market fit?

Yeah, absolutely. So it depends on the stage of the company. You know, at the precede stage, some of these companies don’t even have business bank accounts. So we want to make sure they’re set up from an infrastructure standpoint, to help them from proper reporting to proper board structures and reporting cadence. So we help them set up their, you know, OKRs, and KPIs and help them think about what data they should be tracking to, you know, hit their seed or series A targets, we help them a lot on the recruiting side, we use a lot of our playbooks to help them on setting up their CRM and their sales infrastructure, or their go to market strategies. The seed stage, a lot of these companies hopefully have a bit of a go to market strategy. So more or less happens around like the senior recruiting. So we have an executive recruiting person that works with us to help some companies find their CRO CTO type hires. On the other side, we’re also helping them think about what they’re going to be doing for their next fundraising round. So building a lot of relationships for them with future seed or series A investors that we put a lot of emphasis on what targets they should be aiming for, based on conversations we’re having with those series A investors so that they’re aiming for the right targets, a lot of companies unfortunately, are in that spray and pray mode, you know, seeing what sticks with against the wall. And that’s just not really a great way to build a company. So we try to help them think about what markets they should go after which customers they should be focusing on. We’re not trying to build the product for them, that’s for sure. But we’re trying to help them target that sniper rifle approach, rather than a bit more spray and pray at the early stage, which unfortunately, happens to a lot of companies, they get caught up in chasing, you know, shiny balls, and going deep into some integrations with some large corporates. And that can end up you know, dragging a company through mud and slowing them down. And so we just want to be that sounding board for them whenever they have those big strategy discussions internally as well.

So you know, as you’re helping these companies find customers and helping them with strategy on customer selection and outbound customer acquisition. How do you guys think about the sourcing piece as a venture for, you know, how do you identify these really early stage startups that you’re investing in?

Yeah, absolutely. It’s a great question. I always say this to our team, like, you cannot bet on the best horse unless you’ve seen all the horses showing up for the race that day. And so we really focus on top of funnel lead generation. So we have a really good inbound lead sourcing strategy, our ripple X Fellowship Program, which is our diversity initiative to help underrepresented students across the US and Canada understand venture capital and startup building generates a ton of deal flow for us. We focus a lot on content, my podcast as well, the tank talks has a lot of great benefits for operator stories out there that we get a lot of deal flow from. And then we’ve also developed some proprietary deal sourcing scraping technology to help us look for companies that may not necessarily be fundraising, but they have a presence online, maybe they haven’t been backed by institutional investors yet. And we sort of develop an outbound deal sourcing strategy at the early stage, which is somewhat reserved more for series A or B stage funds or even private equity funds. We’re deploying that outbound sourcing at the early stage, so reaching out to founders on Twitter, or LinkedIn, and you know, finding out that they’re bootstrapped. And then trying to convince them to work with us and go from Bootstrap to venture backed is also a way for us to generate unique deal flow.

So the last piece is selection here, right? So you’re doing some unique sourcing sounds like you’ve got this distributed network, you know, how do you guys think about selection and what is it you’re really looking for in the founders and also the businesses that you’re backing?

For sure. It’s depends on the stage obviously, like one we’re sector agnostic. You know, we’re focused on b2b enterprise SAS, predominantly, you know, we don’t invest in hardware, deep tag biotech pharma stuff, or so we’re predominantly focused on the SAS, it can be, you know, b2b to see professional consumer type products as well. But what we like to look for, especially that precede stage, and we talk about this, a lot of the time, our Monday morning calls is like, it has to do a lot with the team at their very early stages, everyone says, but the market also has to be there. And so we have to go from very, like, top down thesis driven approach to understanding if this company does get to like a series a stage, are they still gonna run into headwinds, because the market is saturated, or it’s just not growing fast enough. And because we’re betting for, you know, seven to 10 years, you have to take a lot of those later stage thought processes into the early stage equation. And we do that a lot as well. But at the end of the day, at the very early stage, the most important thing is team and whether or not they have the ability to sell the vision and fundraise and also recruit people around them, I’d say the hardest thing a lot of early stage founders don’t account for is their ability to continue recruiting the best talent, especially in this very, very competitive recruiting environment, as well as thinking about strategic ways to deploy the capital, when they do eventually raise it, because a lot of people will go from raising a million dollars to then $10 million, and they still don’t know what to do. And they’re still running their business as if they just raised a million dollars to try to suss out all of those things early on is really important for us.

So Matt, you are a solo GP, we’ve seen a dramatic increase in the number of solo capitalists, there was a great article recently, the generalist on this topic, you know, there’s a lot of single GPS out there managing institutional quality funds, you’ve got a couple funds under your belt now, maybe a good place to start, did you always plan on running the solo? Or, you know, was that your intention from the beginning? Or did you consider partnerships? You know,

I don’t really consider myself a solo capitalist, like some of the others mentioned in the generalist article. And the reason why is because I’ve always been focused on building a team around me. And so even from day one, I never took a salary from the management fee, I used all the management fees to invest in my team. I’ve also brought on some outsource support from our fund administration, Team Maduro advisors, to our PR and marketing support to our data scientists and things like that, that we work with. So there are a lot of people. And my partner, Dom like has been with me since day one, Dominic Lau, he’s been amazing and building out our ripple X fellowship program. So I don’t like the word solo capitalists. I think from day one, though, I did know that I wanted to build this firm, as a founder first focus fund. And so in order to do that, and move quickly, I didn’t think that I needed someone else to kind of work with me. But I do plan on bringing on more partners and future funds. And so that’s not something I’m hesitant about. But I do think the benefits of being a solo capitalist, as I have been, when I started it was that I was able to be really nimble, I was able to work really closely with founders and develop a unique brand that represented who I was, as a operator. And as an investor that resonated very closely with the founders. And so I think that all stem from you know, my ability to be empathetic towards the problems that founders are going through. And when you have a bunch of partners that may come from different walks of life, it’s hard to have a cohesive brand that speaks that same language to founders. And so that’s the benefit I’ve seen for myself.

You mentioned some advantages of being a solo, right? Like the firm is very representative of you, you have the relationships with the founders, they kind of know what they’re getting, what are some of the other advantages and or disadvantages of you know, being a solo GP?

Well, the disadvantages are pretty obvious. It’s like being a solo entrepreneur and anything, right? Like, you’re only limited how many hours are in the day, you know, your network is only as big as the ones you keep in touch with. And the ability for you to do everything all at 100% of value is just impossible. So from day one, I focused on hiring fractional support, to help me build out the infrastructure of the fund. And I’ve been very focused on investing in that off our own balance sheet, my own balance sheet to support the firm so that whenever we do take on larger pools of capital, we do have the infrastructure to support that. And again, like that’s why I brought on top class if funded administration team like aduro, to support us, even though we were the first ever Canadian fund that they ever worked with, because I wanted to be ready early on even before we took on institutional capital, to have that infrastructure, that reporting cadence and things like that, but we just had our first kid and so the days gotten a little bit shorter for me, but I will say it is a 24/7 job being a solo capitalist, even if people don’t think it is. And so that is definitely some of the harder parts of it. But I think I mentioned the benefits of it and think the fact that I can get on a first call with a founder and not have to go through like several lines of or layers of associates and principles and then partners makes the founders feel appreciated and respected by firms like ours, which allows us to move a lot faster when it comes to making decisions on deals as well.

Awesome. Well, congrats on the new addition to the family. Thank you. Let’s talk a bit about the founder side. What are some of the biggest challenges you see early stage founders facing right now?

it’s obviously about how much capital is out there. Even though it’s a good thing for a lot of founders out there, we are seeing a lot of founders struggle with how to keep up with those valuation expectations they’ve set for themselves, or just understanding like, how to deploy that capital efficiently is really hard for some of these first time founder. So one, working in this remote world is definitely stressful, and taking a mental toll on a lot of founders. And so we’re trying to be there for them day in and day out to talk to on all forms of communication. I mean, my wife jokes about it. But like, I get calls and text messages from founders all the time, just asking you to like talk about things that are happening at their company, whether they have co founder issues, or some of their early employees are now asking for like massive pay increases in equity up top ups, just because they raised a series a raise, and they they can’t juggle all of that stress and pressure. And so trying to give founders a lot of that support is really important for us. So we have CEO coaches on staff that work with our founders, to help them go from being you know, first time founders to proper CEOs and leaders. And so that’s the hard thing for founders to graduate towards, as well as just dealing with all the different voices on their boards, or in their cap table. You know, one of our newest additions to the portfolio is a company called Lula that came out of the ripple X fellowship program. And the founder came to us after we had known him for several years. And it’s like, look, I’ve got several term sheets for this seed round. And I have no idea what to do here. They’re all amazing firms, but like, we don’t know what to do. And so we had to walk them through the process. And then eventually, we said, well, you know, we can just lead the round for you, we know you very well will co lead the round. And we’ll structure the round properly. So it benefits everyone. And so finding who the best people to talk to on your cap table at the inner layer is also hard for founders these days, because there’s so many voices in their head.

Yeah. Are you finding that Canadian entrepreneurs have expectations for valuations that may be higher or unreasonable based on you know, the headlines and in seeing the influx of capital and what’s happening on the coast, you know, $100 million seed valuations and whatnot. Now, is that something you’re coming across?

I definitely don’t think that’s in our DNA. On the outset, I think they’re trying to just catch up to the market, but not having over the top expectations. In fact, a lot of the term sheets that we have been moving forward with for some of our like series, a series B rounds are not the highest valuation valuations that we’re seeing on the term sheets, we’re actually taking the more realistic one from the best partner. And so what what is happening is founders are getting access to some of the best firms down south, which is great. But they’re also having to go through the motions of like, I don’t want that much capital, but I don’t want them to like go invest in our competitors. And so how do I work through this conversation with these investors, I really want them in my corner. But I also don’t need that much capital to deploy right now, because I just raised my series A three months ago. And now they’re saying they want to deploy 25 million into the business, I don’t even know how to spend it, is what they’re saying. So that’s some of the stuff that we’re trying to work with our founders with at the inner layer of the relationships we have with them,

Matt, you wrote a guide on how early stage founders can better navigate board dynamics, what’s the most important thing founders need to be mindful of when building their board?

So we’ve put a lot of stress and focus on how to make the most of your board, a lot of founders either are scared of their boards, or they look at them as like the principal’s office, and they have to report to them every single quarter, and you’ll get their wrist slapped. But that’s not really the point of a board. What we try to make our founders aware of is this is your time to ask the detailed questions about strategy and operational guidance from people who should have the experience and walked in your shoes before. So one, we always ask our CEOs to write a CEO letter beforehand, kind of going to their mindset of how they thought about the business over the last quarter and their future plans for the year, we always make sure that their data is up to date, and that they share it way beforehand. So it’s not sent out like 20 minutes before the meeting. Because as I always tell our founders, people can read history and books, they don’t need to spend two hours going through it in a board presentation. So get all that stuff out of the way early. And then make sure you save enough time to have strategic conversations with your board that are not in the minute books, but are just saved for your time to have, you know, very valuable advice provided to you from these board members. And so when we do that, and we see our founders listen to us on that they seem to have very productive board conversations, where we’ve seen things go wrong, is where we just get stuck on like the first page like the agenda, because the founder hasn’t been very transparent with a lot of their reporting and they just got caught up on you know, a bunch of other stuff and then finally, the board’s like we’ve never heard any of these stats before, you know, why are you reporting on this Northstar metric and where did you get this KPI from? And so that’s a lot of the stuff that we want to make sure we take care of very early on. But I have heard that from the series A investors that have joined our companies boards when when we were a precede investor and made sure they started having board meetings that they said that that company board meeting was better than some of their Series C Series D board meeting preparations which made us feel pretty good that we were doing a decent job?

You know, I know that you’re passionate about mental health, Matt, what do you think VCs can do to, you know, better support founders through, we’ve got a challenging pandemic situation, but they’re also going through a very difficult startup bill that’s fast and furious. And there can be a lot of overwhelm and a lot of challenges mentally they’re in?

Yeah, absolutely. It’s definitely a problem we’re seeing a lot. And I think what we’ve done, I don’t know what other people can do, but I know it has worked for us is one is just leading with empathy towards what these founders are going through COVID affected a lot of people, you don’t know what a lot of the time is happening in people’s personal lives. And so being empathetic towards founders is really important, and not looking at it purely as a transactional relationship. But a long term relationship is really important. And we try to lead with that, making yourself available also, with founders for like bi weekly catch ups, we often do that with our founders. And sometimes we just don’t even talk about the business. And we just talk about life or some fun things that, you know, we’re looking forward to, you know, building those relationships from founders is really important. And we try to do that often, especially the early days when we’re just starting to get to work with the company, and then also making them feel comfortable to come to you with stupid questions that, you know, maybe you think they should already have the answer to. But if they’re a first time founder, maybe they’ve never experienced that before. And so again, it comes back to leading with empathy on all fronts, and it’s worked well for us.

Very good. Matt, Ripple recently published a series on Web 3 and crypto, I’m curious, you know, what are some of the leading indicators that you guys are following in help guide your investment in the space? 

Yeah, I mean, I think there’s obviously a lot of hype in the industry. And we wanted to, you know, I’ve been investing in blockchain early on 2014 In my own sandbox, and I’ve been around the industry for quite some time. But when it came to web three, I told the team like we need to get really educated here, before we just start making, you know, Twitter posts and LinkedIn posts of you know, we’re investors in web three now, and changing our Twitter handle to like ripple ventures dot eath. So we spent six months going into deep research about the industry, the people building in it, where the human capital is being deployed and and what areas we thought were going to be exciting for the next 10 years, not the next 10 minutes. And so what we came to realize was like, there is an enterprise use case here in web three, that people are going to need picks and shovels for, and we want to be investors in that. So you know, building the Shopify, for web three is like a thesis that we’ve had, and we’re trying to find the companies building that, you know, we’re trying to find investments that help credit investors and non accredited investors get access to a broader portfolio of assets that don’t have the crazy volatility, or building out smart contracts that allow you to send money or loan money in a more secure framework that you’re not going to be hacked very, you know, often on a crappy protocol that you’ve been lending towards, you know, how do you think about building those areas and so we have spent a lot of time researching it. We’ve been investing in our own sandbox in companies like Utopia Labs, which is building infrastructure layer for the DAO’s to be able to pay their employees and stable coins and run their kind of payroll properly for their for their DAO members, things like that is where we’re getting excited, but it’s hard to see through the noise sometimes. And there’s a lot of noise out there these days.

Have you guys developed in a sort of structure framework for evaluating web three and crypto investments?

What we do is speak with a lot of product people. So our venture partner Mike Silagadze, he was the founder of top hat, he’s now running his own defy quant hedge fund called Gadze Finance that we’re investors in. And so we work with him on a lot of like the defi investment strategies. But in terms of like web three, in general, what we do is try to speak with a lot of people who are building in web three, and we actually are building ourselves as well. So a lot of young students in our ripple fellowship program that are obviously really excited about it. And so we punch ideas around with them in our Discord server. But you know, it’s all about just having conversations with people about it, and seeing what they’re excited about what they’re building on. And trying it out yourself, to be honest with you. 

Matt Canada had record funding, like a lot of other areas in 2021. Any non obvious data points or aspects of the ecosystem in Canada, that you would like to share with, you know, a primarily US audience, I think 80% of our 74,000 subscribers are based in the US. So anything that you would like to share with the US investor base, to kind of get them a little more dialed into the Canadian ecosystem?

What I’d say about Canada, and we don’t only invest in Canada, for the listeners out there we do about, you know, 50/50 us in Canada, but for the Canadian investments we’ve made, we have an incredible talent pool. Obviously, we’ve got incredible universities and a great ecosystem and a bunch of great incubators, but our government is super supportive. We’ve got great you know, tax incentives, like our shred credits for a company building in, you know, in the research and software space, which is awesome, huge blockchain and crypto ecosystem here, great testbed for a lot of FinTech plays. So overall, the ecosystem is thriving, and we’re starting to really hit our stride. The other thing that COVID really helped out with was breaking down the barrier for our companies to get access to the top talent around the world who wanted to come and work for Canadian startups. That wasn’t what happening before. One because the venture funding wasn’t there and to the outcomes just we’re not big enough to let people want to leave their you know, Wall Street jobs or fortune 500 jobs to come be executives at a Series A Series B startup, but now it’s happening even in our portfolio, we’ve had top level executives from you know, series D, pre IPO style tech companies in the Valley leave to join our series, a series B companies, as you know, presidents and CEOs and CEOs, which never were the case, and these people are still staying in California to work. They’re just now working remotely for a Canadian headquarter company, which is incredible. And we’re solving a lot of the same problems that US base and global companies are solving to like Rose rocket is solving the, you know, the global supply chain logistics issues trend is solving the infrastructure issues that are happening in the US. So we’re solving global problems, where we’re doing it north of the border, and we’re still getting access to talent globally, which is also just the trifecta for us.

You’re in Toronto, of course, much bigger city than my own here in Chicago. But I moved back here in 2012, I think. And we started to see some really big successes like the Groupons, the grub hubs, Coyote, Echo, you know, big logistics companies, Cleversafe, etc. They started spinning off talent, they started spinning off successes, angels started becoming more active in the ecosystem, there were more founders starting companies. I’m curious if you’re seeing the same thing with the Shopify guys and some of the other, you know, blockbuster successes and spin out founders.

Absolutely. I mean, there’s so many founders that we are meaning coming out of the Shopify, the clear codes of the world. You know, you’ve seen companies like one password, and Fresh Books, and Hopper, Cleo, and Ada, all of these have been raising massive rounds and having some really exciting success. And some of the people who are early employees are 10, 20, early employees, they’re starting their own companies now at the seed stage. And so we’re seeing a lot of that recycling in the ecosystem. Absolutely, just like Chicago had. And just like some of the other areas around the US in Ohio, obviously now Miami’s a lot of like, kind of immigrants or transplants starting companies there, but it’s happening outside of the main hubs of like New York, Boston, and California, which is exciting for our ecosystem, just like it is for yours. 

Awesome. Matt, this question is called three data points, I’m going to give you a hypothetical situation with a startup. And you can ask three questions for three specific data points in order to make your decision, right, because we both know this is how it works. Let’s say you’re approached to invest in a seed stage enterprise SaaS startup companies based in Toronto sector is sales tech. They have 250k of ARR. And they’re growing 20%, month over month again, the catch is you can ask me three questions for three specific data points, what three questions to ask?

I only need to ask you one question. If I offered you $10 million to sell me your entire company, would you sell it to me? If the answer is yes, then it’s not a company we want to invest in because their outsized return is too small, and they’re only in it for the quick flip and the quick buck? If they say no, then I know that they’re not in it for just the money. And they want to build something together. And they think their equity is more valuable than the cash I’m willing to give them today.

One of the questions so the answer is no. What are the next two questions?

Then I would ask them, you know, are you building this for the enterprise? Or do you actually believe that this can expand into multiple TAM? So is it going to be a mid market product? Can you have a product lead growth strategy to this as well? So talk to me about your go to market strategy. And then I think what the other thing I would ask them as far as like, if there’s one employee you could hire today, with the capital, you’re asking me to give it to you? Who would it be and why? 

Love it. Matt, if we could feature anyone here on the show, who do you think we should interview and what topic would you like to hear them speak about?

You know, there’s definitely someone who is an OG in the Canadian venture space that I think has one of the most unbelievable stories out there that probably some of your listeners in the US have never heard, but it’s a gentleman by the name of John Ruffalo, John Ruffalo was the founder and CEO of Omers ventures one of the oh geez of Canadian venture. John has been around the industry for a little while. He’s one of the early investors in companies like Shopify and Hopper, and HootSuite and John, just before he was getting launched his newest private equity fund Mavericks, he suffered an incredible biking accident where he was basically T boned by a tractor trailer and he was paralyzed. And so his story of being at the height of his career and then going out to set out to new highs, and then being sideswiped by a truck and having to go through a year of rehab. And then getting back on his feet again, and still going forward with this fund and building relationships with people along the way. It’s just an incredible story that everyone out there should hear. So I would say John would be one of the guests I’d recommend.

Wow, amazing. Matt, what do you know you need to get better at?

I definitely think I need to get better at time management. My wife tells me it all the time. But you know, we’ve got a lot of things on the go and I am Use my email and my calendars a way to dictate my day. And I just wish I was a bit better organized at writing stuff down and keeping things a little bit more streamlined rather than sort of first in first out with the the inbox sometime.

Matt, do you have any tools or hacks that are a secret weapon for you as an investor?

You know, what I would say is, my secret weapon is my ability to engage with people succinctly over LinkedIn, I’ve become really good at getting people either to be guest on the podcast or engage with us for future like LP conversations by limiting myself to those 300 characters limits you have when you can add a note to connection on LinkedIn. I’ve made sure to include Bitly URL links, because they’re obviously shorter, as well as easy ways for people to book a time to chat with me with like a bitly Calendly link. And so I’ve got a lot of good information and packed in a 300 character box when I connect with people on LinkedIn and my hit rates pretty high. So I’d say that’s one of my secret weapons.

And finally, Matt, what’s the best way for listeners to connect with you and follow along with Ripple Ventures?

Yeah, I mean, our website has all of our stuff listed there, RippleVentures.com, you can reach me on Twitter at Matty B Cohen, MATTY B COHEN. And obviously, on LinkedIn, there’s a lot of Matt Cohen’s out there, but I think you can find Matt Cohen Ripple pretty easily. So we’d love to chat with any founders, investors operators out there and excited to hear what everyone else is building.

Awesome. Well, it’s such a pleasure to have you on today. Matt congrats on all the portfolio success, the multiple funds in you know, looking forward to catching up in the future.

Yeah, thanks for having me, Nick.

Transcribed by https://otter.ai