How Canada Can Become North America’s Trusted Innovation Hub

With Senia Rapisarda,
Managing Director, Toronto, HarbourVest
This week on Swimming with Allocators, Earnest and Alexa welcome Senia Rapisarda of HarbourVest, who walks through her journey from Italy and Wall Street to leading venture and growth efforts in Canada, first at BDC and now as a major LP. She explains how Canada’s venture ecosystem has evolved, the creation and impact of the Venture Capital Action Plan, and why innovation capital is critical to national sovereignty. The conversation covers what makes great Canadian fund managers (curiosity, humility, team-building, and agility), how emerging managers should approach institutional LPs and avoid basic fund management mistakes, and why valuation discipline and non-greedy founders matter in down cycles. Also, Nick Cassin explains how continuation vehicles (CVs) give LPs a choice between liquidity and extended exposure to high-conviction assets when a fund’s term and capital are running out. He describes how the market has broadened to more types of investors and fund sizes, and outlines the conflict-of-interest controls that make these GP-led secondaries work.

Highlights from this week’s conversation include:

  • Senia’s Background, Global Career, and Move to Canada (0:21)
  • Moving to HarbourVest and Designing Canada Growth Strategy (4:00)
  • Canada’s “Perfect Storm” and Agriculture vs Geology Metaphor for Venture (5:42)
  • What Canada Needs to Fully Capture Innovation Opportunity (8:04)
  • How US Allocators Should Approach Canada and Diversification Benefits (11:21)
  • Expectations of Emerging GPs and Importance of Fund Management Basics (17:59)
  • When Continuation Vehicles Make Sense for Venture (21:39)
  • Trends in New Money Capital and Expansion of CV Market (23:40)
  • Managing Conflicts of Interest in GP-Led Continuation Vehicles (26:29)
  • LP Behavior: Who Rolls vs Sells in CV Transactions (31:14)
  • Four Filters for Durable Companies and Role of Founder Non-Greed (34:29)
  • Longevity as an Asset Class and Implications for Pensions (37:03)
  • Applying Longevity and Defense-Tech Themes in Manager Diligence (41:00)
  • Innovation Capital as Part of Canada’s Sovereignty and Late-Stage Capital Gaps (44:33)
  • How Emerging Managers Should Approach HarbourVest and Build Track Record (47:12)
  • Connecting with Senia and Parting Thoughts (51:01)

HarbourVest Partners is a global private markets investment firm managing approximately $150B in assets, with a 45-year history and venture as a core part of its franchise. The firm operates as a multi-strategy, multi-manager platform — primary fund investments, secondaries, direct co-investments, and credit — across North America, Europe, and Asia. Senia Rapisarda leads HarbourVest’s Canadian strategy from Toronto, deploying capital across funds and growth-stage companies and serving as a bridge between the Canadian ecosystem and HarbourVest’s global LP and GP network.

Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com.

Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. 

The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only.

HarbourVest Partners, LLC is a registered investment adviser under the Investment Advisers Act of 1940. This material is solely for informational purposes and should not be viewed as a current or past recommendation or an offer to sell or the solicitation to buy securities or adopt any investment strategy.  The opinions expressed herein represent the current, good faith views of the author(s) at the time of publication, are not definitive investment advice, and should not be relied upon as such. This material has been developed internally and/or obtained from sources believed to be reliable; however, HarbourVest does not guarantee the accuracy, adequacy or completeness of such information. There is no assurance that any events or projections will occur, and outcomes may be significantly different than the opinions shown here.  This information, including any projections concerning financial market performance, is based on current market conditions, which will fluctuate and may be superseded by subsequent market events or for other reasons. The information contained herein must be kept strictly confidential and may not be reproduced or redistributed in any format without the express written approval of HarbourVest.

Nothing herein should be construed as a solicitation, offer, recommendation, representation of suitability, legal advice, tax advice, or endorsement of any security or investment and should not be relied upon by you in evaluating the merits of investing in HarbourVest funds or in any other investment decision.

Transcript

Earnest Sweat 00:03
Welcome to Swimming with Alligators,

Alexa Binns 00:04
the VC podcast from the LP perspective

Earnest Sweat 00:07
with your hosts Alexa Binns

Alexa Binns 00:09
and Ernest. Are you ready? Let’s dive in. Welcome, Sania. So lovely to have you.

Senia Rapisarda 00:16
Fantastic to be here, Alexa and Ernest. Thank you for having me,

Alexa Binns 00:21
Of course, you are a true global citizen, so we appreciate that you will be a translator for us, sitting here in the States. Would you mind giving us a quick background on how you’ve come where you are today?

Senia Rapisarda 00:35
Sure, so I’m Senia Repsada. I have been in Canada now for 15 years. You can hear from my very slight accent that I’m Italian. I left Italy many years ago, and I went to study in the US, where I worked as a lawyer at the beginning, and then I went to work in Wall Street, came back to Europe for 12 years in London, where I met my Quebecois husband, and he persuaded me 15 years ago to move back to Canada, and I’ve been here for the past 15 years investing in companies and Canadian funds.

Earnest Sweat 01:10
So, Senia, you’ve had an illustrious career in the Canadian ecosystem since at BDC. Could you speak about your time there and what you were doing,

Senia Rapisarda 01:22
of course. So, BDC is the Business Development Bank of Canada, and I was hired when I was in Europe to lead the bank effort in really creating an ecosystem on the venture and growth side, because Canada’s ecosystem 15 years ago was really underperforming. There were few funds and very few companies. Much of the talent would then go south, and we would lose a lot of companies and potential upside for wealth. So I arrive at BDC, and my role was to create a process and a system and fund to back emerging managers, therefore identify managers that never had institutional capital, and so I spent the first three years really working with different groups of investors, from angels, from the BDC, internal groups, of course, but also creating a playbook to institutionalize Canadian funds and become then backable by many different groups, not domestic or international, so my role was VP of Strategic Investments at BDC. One other important part of the point was to also realize that it really took a village to build companies and funds, so we also needed not only the BDC, the EDC, the domestic players, but we also had to bring the private sector in. So a second piece of my job became something that probably has been the most rewarding activity in my career, which was to work with the Canadian government with the hand at the time of BDC and design a program that could attract the private sector in the asset class, and that was the genesis of VCAP, the venture capital action plan that we designed at the time with the Conservative Party, that then became was adopted also by the Liberal in Vicky in following years, and again, think about it, especially in this time of polarization, how important and how great is to have something that is working and that both parties will adopt. So this has continued for the last 12 years, that’s what we’ve been implementing, and that started when I was at BDC.

Earnest Sweat 03:42
that literally sounds foreign to me. So you guys got that going, and then, and then you made the move to Harbor Vest. Could you tell us about, like, what was the appeal to your current role and current organization?

Senia Rapisarda 04:00
So I spent most of my career in the private sector, so the BDC was this kind of semi public situation where you have the double mandate, which is really exhilarating, it’s very interesting, where you are profit making, maybe not profit maximizing, but you have several double bottom line, but of course coming from the private sector and top global players, the name of Harbor Best has always been in my address book, and so at the time was one of the group that I had been asking information on how to design the BCAP program, and they had been incredibly generous and open in saying these are the best practices, this is what we see, this is how we built, because Harbor Vest had been in business for now 45 years at the time, 35 years, and really one of the first players in putting in business some of the top venture franchises in the US. So I asked them, How did you do it? What did you do? What is your playbook? And they were incredibly open, so when we did the tender Harbor. Once one of the participants approached me, and he said, “If we win, would you be interested in leading the Gandhi effort? And so that’s how we came together.

Alexa Binns 05:12
I read a wild stat: Harbor Vest was the largest growth investor in Canada in 2025 deploying 1.2 billion, catalyzing much more now, now that you are sort of spearheading this effort, you straddled sort of the government relations, and now you’re doing it on behalf of your clients, the pensions, high net worth, etc. It is the momentum there, you all, you all are now catalyzing this sort of new Canada, a new venture ecosystem.

Senia Rapisarda 05:44
So, this is incredibly exciting. It’s a perfect storm, and in a positive way. So, I’m a half class full person, and so, of course, we, since you know, 2016 we look around the last 10 years, we’re all exhausted about all the ups and downs, whatever your allegiances may be. This news cycle has been changing continuously, and investment is very important, and you keep a steady pace, but now more than ever, I can see there is an incredible momentum for Canada, and let me tell you why. So, obviously, when we started investing, both as BDC and then with HarborBus, I always told people there was a lot of education, education of the pension plan, education of the different players in the asset class, that venture and growth and innovation were was agriculture and not geology, meaning that having a bigger drill suddenly doesn’t make you find this nugget, so suddenly having a large pocket of capital did not make you find this big nugget of hidden managers of hidden companies that have been silently building. No, it is agriculture. You need to see the, you need to really put the different kernels in place, and then go starts at university level, at incubator level, and then see, and then provide a continuum of capital, so in the last 12 years, if you see the trajectory of startups and funds, number of funds that are now on fund two, three, and four, this has been steadily growing. True, we had a kind of a deeper capital that has happened almost everywhere in the innovation, it’s due for a variety of reasons, and Canada always overreacts a little bit, but I think right now, for a variety of reasons, Canada has every single element to really take the mantle in innovation, North American innovation, and be the trusted partner that so many LPs, so investors, or so many entrepreneurs are looking for which is somebody stable that is there and ask the capital and the talent to execute

Earnest Sweat 07:52
What do you think needs to be done for Canada to really take advantage of all that opportunity, and all those characteristics. What do you think is missing today?

Senia Rapisarda 08:06
So many people will say capital, but that is such a reductive question to answer. So, no, I will go. I will be contrary to this, of course. Capital, I think we need bigger tickets and bigger checks, and I’ll explain to you why this has an impact also on the population, but at the beginning it’s a change of mentality. Before you would meet entrepreneurs that will do a company investment, set up a company, and then sell it for $100 million say, and that was a big success. Take 80 million, whatever the share was, and go and play golf in Florida, the repeat entrepreneur was not a common element in Canada. That has changed dramatically. People would maybe take a break, but then come back for more. They will come back as a much more knowledgeable entrepreneur, the experience, and therefore creating a circle of having first of origin in the capital to their investors, but also continue to create companies, so what needs to change is this has to be done a bit more, and I think it’s happening. Building a company and creating wealth is not only for the entrepreneur, but is for the community, and that is a really virtuous circle. So this is happening at a certain speed. I think now Canada can take the pride that is really clear. I’m European and Canadian, but if you go to Europe, the appreciation of what a trustworthy partner and incredible country Canada is, it’s very, very, very strong, and so I think the timing for us to take the mantle is there. Obviously, there is the capital side. I think the one part that has been missing a bit, because you know we’re splitting provinces, is sometimes focused only on regional development rather than national development. Government, and the fact that we have some of the best and top pension planning in the world, those are powerhouses, but with power and law and size comes also the fact that investing in local innovation can be considered reductive, or just doesn’t move the needle, it’s too small, and so that has created an issue of undercapitalization from some of the big asset allocator into the country, and I think we’re finding ways to resolve it, but it has been, of course, a little bit of the friction there. So, I would say what needs to change is clearly more focus on domestic innovation and domestic investments, and domestic investments is not only infra or but is also, as I said, innovation capital, and the fact that I think for success is something good, and it’s something can be shared with the community, and

Alexa Binns 11:51
We just had the guest who came on just before you, Teddy Repko, was talking about how he’s been spending time in India, he’s been spending time in Israel for allocators in the US, what would you recommend? How would you recommend that they start looking at the Canadian ecosystem, and where are the big opportunities? You know, if you’re going to get excited, what are you going to get excited about?

Senia Rapisarda 12:16
So, my CEO just recently spoke about the most important tools that we all have, which is the only free lunch at the end of the day, and it’s diversification. So I think diversification is essential for any asset allocator. We are a global firm, and we’ve always been kind of trail based in markets such as Israel or Asia for many, many, many years, and India, among those. So, the way I present Canada, and I marry it with the type of managers that I usually choose, are managers that are incredibly curious, where other markets are top of mind in an again diversified way. I’m an investor, for example, in a seed fund where 90% of their investments are between Canada and the US, but recently they’ve been looking at a base in Vancouver, they’ve been looking at India, and to me that is a very interesting exposure, and that’s how I present Canada to my US investor, my global investor, is the fact that you can have North American exposure in an incredibly kind of more very disciplined way, and at the same time have 10 15% exposure to different emerging market markets, and so just a matter of actually getting out of your comfort zone, spend the time to investigate who are the best managers and the best companies, or hire someone to do it for you, because we only have 24 hours in a day, and go from there. The firms that have diversified abroad and the allocator that diversified abroad in the past 10 years, rather than just concentrating on the easy part, are the best to outperform the best.

Earnest Sweat 14:10
Are you seeing with Canadian fund managers any kind of like through lines on the kind of best of the best? You mentioned curiosity is something that you look for, are there other kinds of expertise or characteristics that you find in the best Canadian fund managers?

Senia Rapisarda 14:30
I think first of all is awareness that being a fund manager and an investor, it’s an incredibly long-term game. Moreover, if you’re in venture, your cycle before you actually see some returns in for yourself as a carry, not to your LPS, hopefully sooner is 1415 years. So I always tell people that want to be emerging managers that come and talk to me, so first of all, you need to know. That this is not a short game rich type of path at all, so I would say curiosity is definitely essential. Obviously, we would not be in tech and in venture if we didn’t, if we were not curious. Being humble is a really good team member, and being a team player is critical. I know sometimes we see this tech bros, mostly bros, difficult to see. Tech bros kind of being, you know, very sole riders, but in reality it really takes a team, and so some of my best managers are definitely good at building around themselves. They don’t have a high turnover in the team, which is something that is critical. And then they really need to be so agile at changing the type of focus in technology. Now, I’ve been doing this for 35 years, and the speed at which technology is changing is so different from 10 years ago, 15 years ago. I remember, you know, everybody was doing nanotechnology, like a certain sub sector, right? And now you can’t really be in one sub sector, because it’s probably going to be obsolete tomorrow. So I think the agility and capability of adapting is very important, as well.

Alexa Binns 16:25
You had told us that Harbor Fest puts a fund two through the same rigor that you would put a, you know, fund 12, considering a re-up opportunity. Can you sort of tell us what that calibration gets you. It seems unique to Harbor Vest.

Senia Rapisarda 16:46
Well, again, the power of the global platform here is in full display to me. First of all, we are all aligned in our firm. A deal happening in Singapore, a deal happening in Toronto, has the same impact on the firm and on people’s compensation, in a sense, so therefore everybody is clearly aligned and cares. That is very important. We’re not siloed, therefore there is a desire to compare and benchmark, and we also have a very, very strong quantitative team, and so for me it’s very – I don’t want to use the word easy, but accessible to be able to compare emerging markets have never scared us, as I said, we were first movers in Asia, in Israel, in South America, so we did have this kind of desire to see where the pack is going, is part of our nature, but yes, the same scrutiny applies, and so there are some very interesting investment committee discussion, but people have a kind of a playbook of seeing what we call it, you know, recognition pattern of success in what we look at, and maybe you don’t not have a 12 funds track record, but you do have a history of success, a history of how you’re building the team, how you are struck, how curious. Like some of our managers came to Boston and came to Toronto to talk to us and ask us, how do you build a successful firm? And I remember the one at the time, and not retired, the founder of HarborBust, Brook Zook, sat down with a Toronto-based $60 million fund, and basically spent time telling the GP how to build a successful carry and option and incentive, and how to support the younger group people in the fund to be able to contribute, really going to the nitty gritty of what makes it successful, and that to me is a very important because it again is a way to calibrate at any stage.

Earnest Sweat 18:55
What are your expectations from a GP? And then what are the things that you feel like are still like spaces for them to learn, and you’re willing to teach.

Senia Rapisarda 19:37
So we have an open door policy, and part of the month, my mandate, of course, mine, you know, I represent the public, the private sector, and most of the private sector are my investors. Therefore, my mandate is absolutely, absolute returns. On the other hand, I take my kind of double bottom line very seriously. So, educating and giving really good, important tips to emerging managers is. Important, so when you go in front of an institutional investor, don’t go there as a visit just to see how they look and what they do, and a fishing expedition. Be prepared, so managing a fund, there is so much capital that is left on the table by bad management, basically not understanding the principle of fund management, whether it is recycling, the difference between gross and net, and which is what makes you then appear on first quartile, second quartile, third quartile, and a lot of people would come into my office and say, well, first quartile, so when they don’t think I check, of course I would check, and maybe they’re not, so it’s very important that you know what moves the needle, and the needle is moved a lot. There is, like, quite substantial dispersion when you don’t manage your fund properly. Those are boring stuff. I know it’s much more interesting. You know, I’m going to invest in this company because it’s going to be the best in AI, and it’s going to be the best in the stock market. That is a very good story. Fine, but also to show how good steward of other people’s capital you’re going to be in every single aspect is so important, because it shows you’ve done your homework. So this is because it’s my field that shows that you have done your homework in a place where you and I can compare notes, because as I said, technology is super quick, so it will change in. So, if you come and you said, I just have the best AI stack that is going to be native language that is going to do A, B, and C in those 10 minutes, there’s no way I can check whether you’re telling me the truth or not, or whether it’s, or you don’t, but I can check the, you, I can check how good you’ve been in really building a structure for a successful fund, and that really takes just a bit of research and a bit of willingness to study.

Senia Rapisarda 21:49
on this, the Canadian managers were behind, I think. Now they really have been quick studies. We spent a lot of time educating. We sit on every single ELPAC, and we have been really trying to raise the bar there. It’s an easy one to raise, by the way. You just need to study.

Alexa Binns 22:07
Speaking of raising the bar, it seems like there’s a recalibration required, given the velocity that technology change can kill portfolio companies. And curious, how you’re addressing that in your manager selection, the sort of the new world of just technology, you could call it annihilation.

Senia Rapisarda 22:32
So, new competitors, okay? The typical entrepreneur will always come into my room, into my office, and say, whatever, in Europe, in London, or in Toronto now, and for the last 15 years, and said I’m the best. There are no competitors. When I asked, who are your competitors, there are no competitors. I never found somebody who said this is actually a very crowded space, we’re thinking about acquiring them. No, there are no competitors, and still I would then say, okay, if there were competitors, how much of your revenues would they capture, and it was always 1020, 30% and now you use the right word, annihilation, because now it can come a new company and actually takes you out completely, right, so the same way we did a COVID kind of a benchmarking and going through, which you know, triaging our portfolio, existing portfolio. We call it done the same thing with SaaS, and the impact of AI. So we do have a model that we use on our existing portfolio, and now, of course, we use the same model, if not even better, on future investments and new investments, and how big is the moat, and how big, how defensible that is, and the speed at which that can impact. Surprisingly, I think the impact of AI is clearly going to be very felt by companies that don’t have proprietary data, and they don’t have proprietary data that is embedded in payroll or in activities that require regulation. That’s our analysis that we did on software, because just even replacing those is very complex. It will make things quicker, but not necessarily kill the revenues. It may shrink some of the workforce, some of them substituted, but not necessarily, so I think we’re still in a wait and see impact phase, but we do have a very robust model that we use to run our portfolio through.

Earnest Sweat 24:33
In our pre-conversation, you spoke about there was kind of like four filters for kind of like durable great companies, and so like mission critical, big moat, capital efficient, and also not great, greedy founders, which do you think is the most important, if you had to pick one to predict the survival and kind of like thriving a. A during this cycle,

Senia Rapisarda 25:02
The answer is, it depends. It depends on your cash position. It depends on your cash position, in a sense, because if your cash position is strong, then, of course, the having a big mouth is, my opinion, critical, because being like being a mission critical is essential, but if you do not have a strong cash position, not having greedy founders is critical again, because it doesn’t matter whether you have the best technology and the best mode, if you raise at the two at a way too high valuation, and then you have to do a next round. Chances that you’re going to be cramped, and therefore a lot of value is going to be destroyed, are high. So they’re all very important, but it depends on your cash position. If you have cash at that point, clearly you have to stand on your own two legs as a company, and then the market will tell, and therefore mission critical is very important. If you do not have crash cash, I think the attitude of the funders is very serious. We really try, and this has been especially in 2122 where the valuation was so high, and so many, we had entrants in the Canadian market, like the Tiger Capital, the Fidelity, the groups that would come with very deep pockets and very interested in the last mile of a company to kind of manage the expectations of our founders, because at the end of the day, as you know, in venture, the only thing that matters is at the end is the exit. The interim valuation does not matter. Its running commentary in venture is almost unnecessary. It’s interesting, it’s fun, but it’s not an indication how things will end up. So we tried always to kind of manage the fundraising into something that is, you don’t have to do so much to grow into that valuation.

Alexa Binns 27:07
One topic I would love to touch on, while we have you, is longevity, both as an asset class that we can be looking at, and as an allocator looking after folks through their pension plans. Would you mind sharing with us your thoughts on this topic?

Senia Rapisarda 27:28
So, I’ll start from the beginning. I remember being a young associate and being at Nokia, Nokia headquarters in Europe, and sitting down in a cafeteria, and one of the technical guys, one of the engineer guys, was telling me, “Show me one of the ridiculous models, like the brick, and whatever. Say, one day your entire life would be into this, and I roll my eyes. I’m like, “Oh, these engineers, really. And, but I remember thinking, and I went home, and I said the same thing, I think at certain point all our life would be my mobile phone, and this was like 25 years ago, and people laugh, and myself included. Recently, I have been at a conference, and it was about longevity and the impact. I was surrounded by all allocators, including many Canadians, and at a certain point it was a Harvard Medical School. The professor said that he had done a sparing now in rejuvenating cells, and it was working in mice, and it was working in monkeys, so he thought it was going to be probably happening in five to 10 years, and applied to macular degeneration joints, and oh, like skin, skin, but he said no, no, it was going after big diseases, fine, but I, but that the age was going to be probably people would expect to live on 1051 10, and I had somebody, an actuarian from one of the big Canadian pension plans, saying, “Oh my god, my pension base is already one of the most biggest longevity in in the world. This is changing the mathematical model completely, and 7% is not going to cut it. And so I look at him, say, “You see, now you like what adventure it should be more adventure, because that way you can go after real alpha. So I think there is a lot to be said about longevity. There are a lot of them right now, again, we always think more of the tech bros into, you know, doing some type of injection to keep them living forever, not necessarily. I think it’s more about living well rather than living longer, and making people stay at home more. It should be an area that it should also interest very much insurers and companies providing health. Care and keeping and the government in general, because keeping your elderly more at home rather than in a hospital or in institutions is actually advantageous for society. So I think there is a lot to be said. I think that’s where actually AI can do really a lot of good in the speed in which they’re delivering a health solution, and, and also in robotics. I mean, I honestly think that many of us, if they think about old age, and they think about somebody living with you, kind of cringe, but somehow I’ve just saw this little robot that is a pet robot that can also open and give you medication, come to you and bark and tell you time for your medication, and also use me to get up from the couch, and suddenly I was thinking that would not be that bad to actually have the little pet robot doing that for me, and probably keeping me home.

Earnest Sweat 31:19
How are you all incorporating this trend in your manager conversations, or even how you diligence fund managers.

Senia Rapisarda 31:30
That’s a very good question, Ernest. I honestly, as I said, for me, when I see people and I meet people all different space and technology, is to the capability to see where the puck is going, but on the other hand, not the people that jump on the wagon just because they heard it, so they have to have a history, like for example, right now the fence deck is all the rage, right, everybody’s talking about the fence deck, and I’m like, okay, but you know what you mean, I kind of, of course, DAG, and thinking of it for me, urban tech can be considered defense tech in Canada, because 80% of population lives in big cities. The safety of our water system, electrical system, all the cyber attacks, that is defense. Is this what you consider defense? So I split in the truly curious and visionary from the wagon jumper is step number one. Second is really making sure that they have been double clicking and developing a thesis that is proprietary, or there is a special sauce, something where there is this is where I’m going to go. At the same time, again, the dance is always very difficult. Have the agility to pivot, should that not really work right? Because investing, I don’t know, 400 million, say, in this part of the technology that doesn’t exist anymore, it’s problematic. So I would say that, and then, of course, you know the quality, the quality of the people. I’m very strict in the type of ethics and people that we share our time and capital with, and for me to be a good person, a good person, and considered in the society ecosystem is very important. We have a rural harbor bus where we do many, many, many reference calls, and one bad one is already a bad sign. Two is an absolute non-and sometimes in Canada we want to be nice about everyone, so you have to go a little bit off list, or you have to say generalize it, so you don’t ask specifically about a group, but it is a very important tool

Alexa Binns 33:52
That’s a helpful tip to ask about the group, not the individual. If you had to

Senia Rapisarda 33:58
pick one, which one would be the best? Yes, more than asking specific questions about an individual or a team,

Alexa Binns 34:06
who is the weakest link. You are speaking to your clients constantly about the venture opportunity. You described how Canada’s venture ecosystem, you know, swings a little further with the ins and the outs, but the capital really did leave the country for a bit in the venture ecosystem. What’s that argument to your clients? What’s making you personally really excited is that you know all of our folks listening are constantly talking to allocators who have partners, LPs, etc. that don’t necessarily feel the same enthusiasm for venture today.

Senia Rapisarda 34:52
For sure, there was a time where the word venture is still sometimes some boards don’t even allow to be mentioned, so. Call strategic capital, we find different names, right. So, first of all, I start with something very serious, which is innovation capital is sovereignty. People think that sovereignty is borders and land and war or things like this. No, innovation capital is part of the sovereignty and the sovereignty of the future, and so it’s essential that we keep and retain the talent, not only as taxpayers, please, that is very reductive, but basically really as a growing nation and a nation of visionary. We have phenomenal talent, a phenomenal university. So one starts saying this is important, this is part of who will make Canada the future. Second is really explaining that there is a virtual circle and a pernicious one, and the virtual one is when you have, you don’t have necessarily the time and the capability, because it’s small tickets to invest in innovation, so you delegate it, but then you can come later in embarking some of the top growing Canadian champions. I have a couple of companies that have done very big rounds lately. I’m not going to mention names, but they did very large rounds, and the majority of the capital you mentioned, Harper, best catalyzed 1.2 billion in those investments, they came from a pool of capital that were not Canadians, right? Because my fund in Canada can only write the size of a certain ticket, because diversification, again, I can now write more than five, $10 million So, if I want to do a very large round, then I need to go and, using the beauty of having a large global platform take out a pool of capitals, but those are the pension base of California or the pension base of Australia, and so who is benefiting from this company than going public after you de-risk it, which is, you know, double the irony is not Canadian based, and so you, and so that the big returns will go, sure, partly to us, but a very large chunk will go to different country, that is not helpful, so we need to break that, and I think the data was a 90% of tech recap tech later stage Canadian were done by international managers, and so I think that’s there is definitely room for us to take a piece and participate,

Earnest Sweat 37:31
because of the sheer size of your organization. I’m always curious on how an emerging manager should approach an organization like yours. Do you have any guidance on how to navigate that, given you all have so many legs to the tentacles out there?

Senia Rapisarda 37:51
So, as I said, we have an open door policy, so people will write to us and we will definitely get back to them and have at least one meeting, and then what I tell them is usually this is what I would like to see, and I said, for example, I tell very immediately, I don’t waste people’s time, say, well, maybe call me, whatever. No, listen, this is what I would like to see. A first time fund will usually, it’s better off without this type of institutional capital, because this institutional capital will burden your, you and your organization, with so much requirements, so go with the FF, the friends, family, and fools, they call them in the lingo, the 3f’s but go start and start creating. First of all, an initial, maybe you do a pledge fund, or maybe you just do it a small fund, where you show your thesis is proven by the fact that you can source the best deals, and then come back to me and show that at least that’s what you’re doing, like you do milestones that are not necessarily exit. You just tell me a story, and then come and update me every six months, telling me 15 minutes just to give you an update. We now have closed 20 million, and these are the companies we’re investing in. This is a whole day that already creates a track record in the company, because we track everything. We are very cons-paced, so I will have notes that are uploaded, and they will know, and if I end up under a bus, somebody else will know in the firm that you spoke to me before, and we will track at that point how you know the what I call the say do ratio, and if the say do ratio is high, then already creates track record. So, there is that. So, step number one: talk to us. If we say no, don’t just sulk, come back. I, you know, come back every six months with an update, 15 minutes, even an email, saying this is what I’ve been doing. Please let me know if you would like some type of footer play. Second piece, I will always make sure of myself in the team, we’re all trained to tell you this is my sweet spot for direct deal. Bring me a co-investment. I always joke that average la. The length of a fund commitment is longer than the average marriage in North America, because it’s 14 years, right. So, for me to commit to a fund and paying fees for 1412 years plus extension takes a big leap of faith, and therefore it’s much better that we date before with a deal, and which I see how you operate, what you’re doing, and even if then I end up not doing it, you are so bringing me co-investment, and that is so important, and many of the co-investment that happen in Canada are not big enough for the big allocators, but when I, when you have a dedicated fund like we do for Canada, then is the, you know, 2 $5 million $10 million dollars, that actually are the right by size to work together with an emerging manager. So, again, so step number two, bring me something, show that you are willing to do co-investment, and, and three, absolutely be prepared on all this, not only on fund management, but always prepare, be prepared to like you’re presenting to a top institutional investors, so don’t don’t come with just a chit chat, be very professional, food institution matters, still institutional investor, this still matters a lot,

Alexa Binns 42:15
And just, how do people get in touch with you if they think it’s a good fit, and to sort of self-fill, all our

Senia Rapisarda 42:24
details are on the internet, so harborbus.com My name and last name are very memorable, not that many people with this name on LinkedIn, and they can send me a message on LinkedIn, they can send us an email, and we usually, you know, I’m pretty responsive, and if I don’t respond, please pester me. It means that I just thought, “Oh, I should respond, and promptly forgot the perks of middle age.

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Earnest Sweat

Earnest Sweat is the Founding Partner of Public School Ventures, a dynamic syndicate of over 600 technical operators, go-to-market specialists, and LPs. Previously, Earnest built new venture capital practices at Prologis and GreatPoint Ventures. His focus is on investing in value chaintech, specifically vertical SaaS, applied AI, middleware, and B2B marketplaces, which are poised to revolutionize foundational industries like real estate, insurance and supply chain. Earnest has sourced and led investments in companies such as Flexport, Flexe, KlearNow, and Lula Insurance.
Alexa Binns

Alexa Binns

Alexa Binns is an angel investor and LP. An experienced investor and operator, she has climbed the ranks from associate to partner at Maven, Halogen, and Spacecadet Ventures and built digital and physical products for Kaiser, Disney, and Target. Alexa has worn every hat in venture from fundraising to sitting on boards. She invests in companies with mass consumer appeal, focusing on the future of shopping, health/wellness, and media/entertainment. Key angel investments include The Flex Co, Sana Health, and Chipper Cash.

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