Launching Through the Looking Glass: Underrepresented Limited Partner Views

Those familiar with Laconia know that community, transparency, and accessibility are core to our day-to-day as we work on building a more supportive ecosystem for entrepreneurs and investors alike. Whether it’s literally opening our doors to any founders with questions or hosting educational events on the venture asset class, we prioritize closing the opportunity gap within the early stage ecosystem.

As an extension of these initiatives, we could not be more excited to announce a new content series focused on amplifying underrepresented Limited Partner voices.

Over the past two years, there has been a long overdue surge in attention toward diverse founders and investors. Organizations such as All Raise and diversity-focused investors, such as Female Founders Fund, Gaingels, Harlem Capital, and Backstage Capital, have shed light on both the institutional challenges plaguing the tech industry and the champions bringing us closer to an equitable future.

With studies on professional investors’ assessments of diverse fund managers and articles on diversity within asset allocators, we are just beginning to see Limited Partners - the people and institutions that invest in venture funds - take on a more central role in these conversations.

Despite strong foundational efforts to increase transparency in the LP ecosystem, there is little content focused on amplifying underrepresented perspectives on critical industry issues. Based on anecdotal conversations and wholly unscientific Twitter asks, even getting a basic understanding of LP demographic data presents a challenge.

 
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Given the central role LPs play as capital allocators, advocates, and arbiters of change, it is critical that we include their voices in our conversations. We could go on for days about why representation is essential, but below are a few top-of-mind reasons:

  • Just as diversity within VC fund managers has downstream effects on founders’ funding, it has an analogous impact at the LP-to-GP level. If we want to see industry-wide progress, we have to include the top of the capital stack.

  • Access to information and widespread representation are essential to narrowing the racial and gender wealth gaps that persist today. Generally, women and underrepresented minorities are less active investors, and they certainly seem to be more passive participants, particularly in private markets. Our hope is that bringing leading investors to the forefront will reduce the caginess of the industry and decrease the barrier to entry for new investors.

  • In an industry premised on surfacing outliers, following the crowd remains far too common, and highlighting underrepresented perspectives has never been more essential in driving both progress and profits.

We are thrilled to publish our first six interviews with Kelly Hoey, Amith Nagarajan, Lo Toney, Holly Lynch, Diane Henry, and Carlos Miguel Gutierrez:

Their stories cover a multitude of backgrounds and roles, providing a strong foundation for this series. We will be continuing these conversations on an ongoing basis, hoping to spotlight diverse perspectives across all possible parameters. 

If you are an active Limited Partner and you:

  • Consider yourself underrepresented within your peer group (with regard to traditional demographic parameters such as gender, race, sexual orientation, or secondary criteria such as educational background), or

  • Are executing on an “outside the box” LP approach, such as investing in underrepresented GPs, social impact companies, or other atypical strategies, or

  • Have never publicly spoken about your LP investment activity and would like to do so...

...please reach out to us! By highlighting the insights you’ve gained through your investing experience, the barriers you’ve overcome to get where you are, and the opportunity you’ve discovered in this asset class, we hope to take another step toward tangibly moving the needle on a more inclusive and thriving ecosystem.

Thank you to Beezer Clarkson, Samir Kaji, Semil Shah, Ted Seides (Capital Allocators podcast), Notation (Origins podcast), and the #OpenLP community for paving the road toward LP-focused content (please let me know who I’m missing!); to Dessy Levinson, Nitya Rajendran, and Doba Parushev for your thoughtful feedback and support; and to Nikita Singareddy, Ed Zimmerman, Kim Lew, Mike MacCombie, Shai Goldman, Elizabeth Yin, Kelsey Banos, Del Johnson, Hana Yang and Declare for the impact you’ve had on my thinking & the creation of spaces for these discussions. 

Through the Looking Glass: Underrepresented Limited Partner Views

Through the Looking Glass: Kelly Hoey

Kelly is a speaker, strategist, and investor with a focus on creating opportunities through networking solutions. She has worked with leading companies, professionals, and organizations to help them understand, leverage, and unleash the potential of their formal and informal social networks. Kelly is the author of the book “Build Your Dream Network: Forging Powerful Relationships In A Hyper-Connected World”. You can follow her on Twitter @jkhoey.

I’d love to start with a little bit about how you got involved with working and investing in the tech and startup world.

All because of networks. I left the legal industry and became the first president of the global business network 85 Broads (after the founder Janet Hansen offered me the job of a lifetime). In that role, I encountered such a diverse range of professional and career-focused women, in terms of the businesses and the ventures that they were either in or moving into, and that exposure really expanded my network. 

There was a bunch of women at 85 Broads who were entrepreneurial and involved in the NYC startup community. Two of them had an idea for a startup accelerator. As they socialized the idea within the startup community, people would say to them, “You need to talk to Kelly.” They talked to me. I came on as a co-founder. Upon reflection, it was sort of organic as to how I became involved in the startup community.

The second piece, in terms of thinking more like an investor as opposed to a startup advisor, happened because of another 85 Broads member, who started Pipeline Angels. When Natalia initially had her idea for Pipeline Angels, she reached out to me to share her idea, ask what I thought about it, and then asked me if I would be part of the first cohort. 

I did that first cohort of the Pipeline Angels and during an early presentation to the group, a male startup founder/angel investor described how he made investments. And he said something along the lines of, “I do my research into this and that, and then, you know, I trust my gut and this is why I make investments.” After hearing his approach, I was like, ‘Well, I can do that’.

Getting involved in early stage investing has really brought together so many of the things that I believe in: being actively engaged in your financial health, taking an active interest in companies I believe in, as well as the education component of being a lifelong learner.

When you started angel investing, how did that compare to your level of involvement with other financial asset classes? 

Doing the angel investing bootcamp really had me look at my other Investments differently, in terms of what my exposure was, and it made me much more vocal. I have an investment advisor in Canada (because of retirement funds there), and I have an investment advisor here in the States, but my involvement with my investments typically meant meeting with them annually and going over what's in my account. After the bootcamp, I asked a lot more questions (why is a particular stock in there, what I want in there etc.). I think doing the angel investment boot camp made me much more vocal as opposed to you know, just kind of nodding slightly, as the advisor reviewed the account. 

Did you approach your startup investments from an international lens? Or was it sort of opportunistic? 

It's the same way as I invested in Laconia. It's about who you know. It's totally relationships. Angel investments are made purely on the basis of knowing the founders. Products and markets change, people rarely do. Being an angel investor worked when I had the time to be really fixated on getting to know founders and had the bandwidth to be there to help them out and research opportunities etc. My two cents: if you're going to be an angel investor, then you need to decide whether you're going to be all in. You’ve got to be there and be active in whatever vertical or sector you’re looking at. After a certain point, I didn't have the time to do that. I figured if I'm going to be a passive early stage investor, then it's much better that I have somebody else do it, so I became an LP.

One thing that seems to come up repeatedly is that LP demographics typically skew a certain way. What have you seen work or not work in terms of expanding the traditional decision-making base in venture to a next-gen LP base?

I'm hoping things like this interview.

The women who are investing need to speak up and say why they are investing and who they're investing with and what they do. It's one of those things that when I'm asked to talk about it in situations like this, I do because I think women need to be much more active and visible.

And women need to think about how they are investing their money.  Your traditional investment advisors will not give you advice on early stage. It's one of those things you have to seek out. We seek things out through people we know and socialize with people, who look like us.

With the amount of wealth that is sitting in the hands of women, I'd like to see us actively doing something with it as opposed to bemoaning the fact that we don't see the types of products, services, and founders we want. My attitude is we can either complain or we can direct the wealth in the direction we want to go. And if you need education, get an education. If you need inspiration because somebody else who looks like you has done it, read this article. 

It seems like even in conversations I've had with underrepresented General Partners who have networks of women and minorities, their close rate is significantly lower. Why? 

At the early-stage, you have a lot of conversations in order for people to get comfortable and to get them to see themselves as investors and valuable contributors beyond money.

It is just going to take time. There will be a trigger point. Because this is not something we need to complain about as that’s not a solution. There's a really easy solution in terms of women saying they can't see female founders or fund managers, or people running investments who look like you, Geri. Pull out your pocketbook ladies! There are women to invest in. What's the problem? 

Speaking as an LP, as a female investor, besides knowing Jeffrey and thinking of him as mentor of mine and one of the people who I've always trusted in the New York startup community, when he told me about launching Laconia, my reaction was ‘How about me? Can I be an investor in your fund?’. 

There was also the way the fund was set up in terms of the complete transparency and the ability to get involved, because I hadn't thought about being an LP. I recognized it was important to be invested in early stage companies, but back in 2015, I was thinking about writing my book and knew I could not be a successful full-time author and angel investor at the same time. I remember Jeffrey and I were having breakfast, and he was talking about raising the fund. As he described the structure of the fund, something about the fact that it was really hands-on was really appealing to me as opposed to just handing over the check. I think that transparency in the ability to add value and get involved more than just writing a check is probably what tipped me over to be an LP. 

Any thoughts on people who are considering investing in any capacity on the best ways to get started?

If you don't understand your investment portfolio, go and meet your financial advisors. I'm sure people have a traditional financial advisor who can help them understand what stuff is really safe, where's the risk, etc. But you should figure out what percentage should be in a higher risk, greater return category (early stage investment) and then actively make a commitment to do that.

If you don't know how to get involved, then I would say go and do an angel investment boot camp. There's enough of those out now, and all you put at risk for doing the boot camp is the amount of money that any of us would be writing for a table for a rubber chicken dinner at a not-for-profit gala. So just consider it your nonprofit investment. Or become an activator with SheEO (global community supporting women-led ventures launched by Vicki Saunders) because you can dip your toe in, gain exposure to incredible female founders and then you get to write that contribution off as a not-for-profit investment. Do something to get the exposure and flavor of early stage investing. For me, going from an angel bootcamp group to investing as an LP was a really natural progression.

I also think doing the angel investments made me a better LP investor. I’d suggest to anyone that they think about what asset classes should be part of their overall investment portfolio and then think about how they want to be involved with those investments. Do you want to just have a meeting once a year and never hear from someone you’ve trusted with your money? Maybe that's what you do with your financial advisor. Early stage companies need more help and you want to be involved. 

You had written a piece a while ago about Aruba. Tell me a little bit more about your takeaways from that trip. 

What's funny about that piece on women in leadership in Aruba is that the first thing people (typically women) say to me is, “It's a small country” and my response is, “Time out.” It was a perfect petri dish ecosystem to examine leadership and competitive behavior between women. It's the same dynamics as with industries here in New York City -  not everyone gets to have the top rule.

So why is Aruba succeeding in behaving in a certain way (advancing and retaining women) and why can't we all do that? What struck me were the network dynamics of women in Aruba truly helping other women. There was no work culture of backstabbing and kneecapping. Women who understand the pressures and demands that other women have to deal with in their roles (whether industry or government) are delivering advice and feedback based on the role or position their friend is in, and not with any sort of rivalry or cattiness or scarcity mindset. 

The other factor that stands out in Aruba is that these women leaders all stayed in the game. It never crossed their minds to step out or exit their career, and that makes a huge difference because across the board at all levels, from top to bottom in government and industry, you have female role models and gender diversity.

When I was interviewing Arubans for the New York Times piece, I asked a young man what he thought about having all these female bosses. He told me he’d never even thought about it. Other than realizing they live in a place where there may be limitations on career, women in Aruba don’t have any feeling of a glass ceiling or limit on what they can do.

I immediately tell people, usually women, that this is an example for the rest of us to follow. Don't just dismiss the story. There was this immediate jerk reaction to dismiss the story when it came out, as opposed to saying ‘What can we learn from Aruba? Is there anything in my individual behavior I can change?’. We may not be able to change the entire country, but we can change our individual behavior. Shifts in individual behavior is what starts cultural transformation.

Thinking about Aruba, what I want other women to look in the mirror and ask themselves how are they supporting other women. Look at who you have promoted or recommended or sponsored. 

I’m really proud that I had the opportunity to highlight the women leaders in Aruba. Highlighting them hopefully encourages more women to see themselves in leadership roles. I'm also so interested in making sure we're shining bright lights on people who are succeeding rather than simply continuing to talk about the challenges. Problems are solved by action. If we only keep talking about how shitty things are, things won’t change.  


Through the Looking Glass: Amith Nagarajan

Amith is a serial entrepreneur who believes in combining purpose, passion and profit. He is the founder of Aptify, a purpose-driven company focused on providing technology and services to the not-for-profit sector around the globe. More recently, Amith founded Association Success Corporation, a group of businesses rooted in a shared purpose of helping associations achieve greater success. Association Success’ companies include rasa.io and AssociationSuccess.org. You can follow him on Twitter @AmithNagarajan.

I'd love to hear about your background and how you started your first business.

I am a Silicon Valley native. I was born and raised in California and grew up with computers. My dad taught me how to write programming code at a very early age. I've always wanted to be an entrepreneur, so early on, I had a variety of businesses a kid. I started my first real business when I was a junior at Cal Poly, San Luis Obispo, which is in the Central Coast of California.

That company turned into a business called Aptify, which I scaled globally over 23 years and ultimately sold in 2017. That was a really long chapter of my life and a fantastic experience. I grew a lot as an individual. The company grew tremendously, and it was a big success. There's a number of elements in that experience that shaped my perspective on entrepreneurship and the role I should play in entrepreneurship. 

Aptify evolved in many ways, as companies do over that long of a period of time. Roughly 15 years into the journey in the late-2000s, I thought the company was in a place where my own direct involvement was becoming less important on a day-to-day basis. I was still very much the strategic, visionary driver of the company. I loved the creation of innovative, disruptive new things, the team, and the culture, but I didn't really like the operations side that much. At that point, the company already grown quite a bit, with offices all around the country and starting a global expansion. I was fortunate to have a great executive team that was far better than I was at operations. 

I should mention I never raised money or took on debt at Aptify. That approach has its pros and cons. The bootstrapping process taught me a lot of valuable lessons at various points in time. 

I realized that I wanted to get involved in earlier stage businesses again and started investing in early-stage companies as a way of giving back. My investment process was about finding entrepreneurs who I thought had great potential, decent ideas and were solid people. I wanted to take on the highest possible risk at the earliest possible stage because that's where I felt that there was a need. 

That’s my story. Aptify has been a big part of it, as has investing in companies over the last ten years. Since selling Aptify, I have been actively focused on an artificial intelligence startup called rasa.io. It is a platform for content personalization, specifically in the form of (what we call) Smart Newsletters. That’s what I spend most of my professional energy on.

I'd love to talk a little bit more about the bootstrapping angle. You mentioned it didn't necessarily make sense to raise money for your company. How do you get a sense of whether or not early stage companies are what we would refer to as venture scalable or whether the business warrants taking outside capital?

Well, I think that it depends on how you want to focus the business. In product-led companies where products are capital-intensive to create, there's a significant ramp-up period of time before there's any noticeable revenue. In those types of businesses, you typically need funding. 

What I ended up doing was doing a mix of products and services. The DNA of Aptify was always a product company, but we supported ourselves through professional services. You could argue that approach is great because it allows you to bootstrap and reinvest services profit into product development. You could also argue that slows you down tremendously because you're distracted from the product development. But then you can argue that by doing services, you're on the front lines with the customer, with a far better understanding of the customer’s problems. You can craft a product solution across multiple customers based on that pattern recognition that people who are in the ivory tower of pure product development couldn't do. So, you can go back and forth on that.

I think it depends on the intentions of the founders. It's obviously the cool thing to do to say ‘Hey, we're going to do a venture scalable business. We're going to have an exit or an IPO,’ and those are great businesses on a number of levels. But the probability of success in that format of business is usually significantly lower. The risk levels are higher intentionally since they are going after the bigger opportunity and deploying a lot more capital earlier. In the other business model where you're starting a little bit slower, you can have a hybrid model of services and product, funding part or perhaps all of it yourself.

Then you're calibrating to figure out where the product goes. That model might lead you to large scale, but it can also become a business that just has an evergreen kind of a feel to it, able to generate significant cash flow and wealth for the founders and other stakeholders.

I don't think there's a single formula for venture backable companies. A lot of times people who are looking for funding look at services as being a toxic element to their business model, and I think that's an unhealthy approach as well. There are a lot of situations where services can be a strong complement. 

How do you think about Advisory Boards versus Boards of Director? And what advice do you have for entrepreneurs on setting those up and managing them effectively?

My companies haven’t had outside investors, so I haven’t needed an official board of directors. I have a group of advisors as opposed to a group of directors. Regardless of what the terminology is, I believe that outside advisors should be active in experience sharing, deliberation and even decision-making, in some cases. 

I don't like advisory meetings where everyone gets together once a month or once a quarter to say, ‘Hey, here's all the great stuff we've been doing,’ and for the advisors to say, ‘Oh, good job.’ Everybody loves to get a pat on the back, but the point of advisor meetings is to take you to the next level, to coach you up, to drive you harder, and sometimes to take you to places you wouldn’t have gone on your own.

For my meetings, we send a brief ahead of time and expect advisors to invest the time to study the materials beforehand and come into the meeting with questions. We start the meetings right off the bat with Q&A. Then, we go into two or three discussion areas where we expect to have a vigorous conversation and leverage particular advisory expertise. I construct the groups by looking for industry experiences or skill sets as well as networks for introductions. And I set the expectations that in addition to attending the meetings once a quarter, we're looking to the advisors to help us connect with partners and prospects and occasionally roll up their sleeves a bit to help on projects. 

We're looking to them to engage in a very limited way in terms of project work, as we don't expect people to be part-time employees or anything like that. But if they end up putting in an hour a week, that's a pretty big commitment over the course of a quarter. That's 10-15 hours per quarter as opposed to just attending an hour-long meeting once a quarter. And that's a different level of expectations that most advisors have, but my point would be that if all you're going to do is meet with advisors once a quarter for an hour or two, it's almost impossible to get a lot of value out of them, no matter how great these people are. So, I give my advisors a bit of equity, and then I expect them toto be a part of the team. 

How did you end up in the market segment of associations? Was that incidental, or did you seek out a mission-driven or social impact-related industry?

It was really dumb luck. When I started off in ‘93, I had no idea what an association was. I had no idea about pretty much anything. All I knew how to do back then was write code, and then I figured if I want to start a business, I better take on a business major. I knew fundamentally a lot of the basics, but I was a really good developer. I started building products. And our products were actually fairly successful the first couple of years.

We didn't make a ton of money, but we had over a thousand organizations adopt the low-priced tools that we were selling. It sounds impressive to say 1000+ companies, but they were buying either products for hundreds of dollars or services. A lot of these companies would call us up and say, ‘Hey, we purchased your tools and they're awesome. But we need you to come help us take advantage of them.’ We didn't know what professional services were. We helped our customers use our tools and checks started to come in for much larger dollar amounts, for tens of thousands of dollars. Eventually, six-figure checks started coming in for services, and we thought that was fantastic.

Then we started to realize how hard it is to scale a services organization. The DNA of the company was always focused on intellectual property and product development and building a consulting team was a very different thing. One day we got a call from an association that had come across our tool suite and wanted us to help them build a reporting application. Our tool allowed programmers to more rapidly build all types of business applications. By then it was the mid-90s.  We ended up doing a lot of service work for them and realized that selling a very generic product like ours across all verticals made it fairly difficult for a small company to find a product-market fit because you're selling anything to anyone. Anybody could be your customer.

It got us thinking, ‘Hey, what if we built some applications? We've got this platform that's so incredibly fast at building apps that rather than selling the platform, what if we picked a couple of specific applications that did a lot more for people and would be valued higher  than just tools?’ 

And that was around the time when we met this association. After working with them, we realized this could be an interesting space because it was obvious that they were spending a ton of money on custom application development. It didn’t seem like there was anything good at the enterprise level for this market.  

It also just so happened that the person who was our main contact with that association decided to change jobs, went to a different association, and took on a new job. The association he moved to was looking for a new CRM system, and he knew that we were thinking about building this type of application.

He agreed to be our first app customer in 1998. At that point in time, we stepped on the gas and grew very quickly. We were beneficiaries to the fact that Y2K was in full swing, and people were replacing systems rapidly. We grew like crazy in those couple of years and from that point forward. We thought we would go after multiple verticals, but we really never looked back from the association space as it was  a large market that served people in a way that we really enjoyed. 

The nonprofit and association space often gets a bad reputation as being a small market, and I think it leaves a lot of white space for founders to build interesting things.

It really does. It's viewed in two ways. In the first way, people look at it and say, ‘We want to do some pro bono stuff. Let's go help these guys out.’ In the second way, people look down their noses at it a little bit. And the result is that the technology in this space tends to be behind. It's usually more than five years behind that for mainstream companies. It's tough for those people, and that creates massive opportunities. 

There are hundreds of thousands of associations around the world. In the United States and Canada alone, there are tens of thousands of sizable associations. We had sold our product to hundreds of the largest ones by the time we sold Aptify. Our focus was on the largest groups because our platforms strengths appealed best to that part of the market. There's a lot of space in the market for people who have a truly innovative idea and are willing to help solve big problems. Associations are hungry for good ideas. 

You mentioned that you started making angel investments. We’re seeing more and more startup founders starting to make angel investments relatively early on when they're still building their own business. What are your thoughts on that in terms of opportunity cost, focus, and pros and cons? What would your advice be? 

I think it depends on how involved they are. If it's ultimately purely an investment, and they are putting a little bit of money into something because they believe in it and are not really putting a lot of their time into it, I would probably fine with it. If a founder I had invested in was diluting their attention by serving on boards and doing a lot of other things, that would concern me, because startups are all-consuming and no matter how good the founder is, there's not enough time in the day to do what you need to do in your own business. That being said, I do think it's awesome that founders are starting to pay it forward.

When you're evaluating your venture activity, how do you think about making fund investments versus direct investments?

As an early stage investor, the deals that I do are more based on founders I believe in or want to support.  

I am purely focused on driving entrepreneurship forward. It is not intended to be a donation. It's intended to be an investment, but it is much less financially driven than an LP investment into a fund. That, to me, is investing in an asset class. As an LP, I'm putting dollars in looking for a return in that fund just like any other investment in any other asset. 

As for the individual investments I make, I do see returns on them, too. I've had a couple of exits already, which have been great. To me, it's more about being supportive. It's a way of giving back to entrepreneurship, which has been something I feel incredibly fortunate to have had success with. When I started out, I didn’t have any support or resources so I try to be helpful to other entrepreneurs.

Tell me a little bit about your process for making investments.

I like to see at least two founders because there's always a benefit to a balance between people. I like to see founders who are fully committed. They have to be either full time or willing to be full-time upon receiving the investment and not looking back.

I also look for people who not only have the commitment bu also have the stamina, the determination, the grit to persevere, and the emotional intelligence gained from having been knocked down a few times. People who have unbelievable talents but have had nothing but success in their lives or have been insulated from defeat don't recognize signals from the market quickly enough to react to them. There are a lot of really smart people who don’t succeed because they're so full of themselves that they have a hard time figuring out when they have it wrong.

Part of what I do is interview founders somewhat similarly to how I interview potential employees for various companies. I try to give them some critical feedback, directly in the meeting; it is very rare for people to get feedback like that, in terms of their presentation or something else. Then I can see how they react to it. Are they coachable? Do they take feedback well? I look for people who react positively to feedback in the sense that they are open to the input. Not that they are willing to change their view immediately as that would be something that is concerning too. I want people who have conviction in their beliefs while at the same time are open to hearing opposing thoughts.  In these types of discussions, you can usually tell pretty quickly if someone's genuine or not.

I look at the idea, of course,  but I don't do massive amounts of diligence on the idea at the stage that I invest in because it's so early. And idea is going to evolve tremendously. I look for a good core of an idea, and I look for a rock-solid group of people that are passionate about it. 

Are there certain values that are important when you're selecting entrepreneurs to invest in?

Definitely. Social purpose is my preferred way of describing it. Essentially, I invest in companies that exist to do something positive outside of just making money. Just making money is something of a hollow victory. My companies have always been aligned with that way of thinking, much more so in the last 10 years than before that. The success that we had with Aptify and what we’re doing at rasa.io is very much driven by this idea of a purpose that fuels the team and provides the bedrock of the culture. I look for entrepreneurs who have a belief system. I want them to be extremely motivated and driven by financial return, but I also want them to be looking for something bigger than that. I'm hoping that they are people who want to drive positive social impact as well. 


Through the Looking Glass: Lo Toney

Lo is the founding managing partner of Plexo Capital. Previously, Lo was an investing partner at GV and Comcast Ventures. Lo has held executive roles at both startups and global consumer brands. He was the general manager of Zynga Poker, the gaming company’s largest franchise, and held operating positions at Nike.com and eBay. You can follow Lo on Twitter @lo_toney.

I would love to hear a little bit of background on what led you to start Plexo. 

This all started when I was at GV. We were looking for a way to get access to a lot more deal flow to fill the top of the funnel. One of the things that we noticed was the dramatic increase in 2015 in the number of seed-stage funds. I realized that was a great way to get access to deal flow: building relationships with folks that are upstream. 

Then one of the things that we noticed was that along with the increase in the number of firms in that particular stage of investing, there was much more diversity than you would see at larger billion-dollar funds. The thing that was interesting to us in conversations -- and this was not a surprise to me -- was that the path for women and people of color was a non-traditional path relative to other folks in venture capital, and, as a result, women and people of color ended up with really interesting networks. Also, they had a different lens to evaluate deals. 

There's a number of other things but those two, in particular, are important because we realized that by establishing relationships with those folks, it would allow us to get some differentiated deal flow. One thing I have noticed is that as an African-American VC, I will see a lot of deals from African-American entrepreneurs. They almost seek me out and I've heard this anecdotally from female VCs as well: if you're a female, often you'll get deal flow from a little bit outside of your network or from referrals from other female entrepreneurs. That's an interesting way to tap into deal flow that other folks may not be seeing. 

I think what's interesting about the different lens that women and people of color have in certain instances is that there's not a lot of data. If a company is going after a particular market or a problem that the GP has familiarity with, or if the problem has some relevance to the ethnicity or gender of the GP, and there's not a lot of data to show that the company has traction yet, then, there may be an ability for women and people of color to identify very promising companies earlier. I think those two things were pretty interesting at GV. We made five LP Investments into seed-stage funds led by women or people of color, and it worked for us.

I saw the potential to scale that model up and around February of 2016, I started to think about what that model could look like. I spent some time researching it and got a lot of support, which was great. I approached it like an entrepreneur would approach building a company.

I would say that this journey has been much more entrepreneurial in nature than venture-like in nature. The first thing to do was to really understand the market, the problem on both sides --

  1. both for LPs trying to deploy capital, and, in particular, if they were looking to deploy capital in diverse GPs, and 

  2. the challenges that some of the GPs have with trying to raise capital 

-- in other words, really trying to frame the problem or the opportunity and then determine how big the market for that strategy is.

If my fund was going to be investing as an LP into diverse GPs, how many of these diverse GPs even exist? If there are only five, then there may not really be a model there. But there are many more than five. That's the good news. Then I began thinking about what I could do to differentiate the model and position it differently in the marketplace. I thought the hybrid structure of investing both as an LP as well as directly into deals was interesting. Then I got back to the roots of this, thinking about how I could work with LPs like GV: what if I could get the interest of a downstream investor to invest and feed them deal flow as well?

I started to have conversations with those who would ultimately become some of our LPs such as Cisco Investments, Intel Capital, the Royal Bank of Canada, Hampton University, Kapor Capital, the Ford Foundation and others, to really try to see if there was something interesting around this model. I even had some conversations with LPs that like to both invest directly as an LP into GPs and then also do directs. They saw Plexo as a way to ultimately learn more about GPs that they then might be interested in investing in directly. So once I started to kind of gather all of this feedback, doing my own customer development work on all the different sides of the market, I came up with what I thought was the right approach.

That was right after Thanksgiving of 2016 and then I started to work on it full-time in December of 2016. I incubated it at GV, really started the journey of raising capital, and ultimately spun it out after we did our first close in March of 2018. We brought in our founding LPS, including our anchor Alphabet, and as part of that structure, we brought the original 5 LP Investments that were done at GV. This made sense because at the end of the day, GV was not in the business of trying to manage LP investments. It really was a good match as GV was able to continue the relationship with me and continue to get access to the deal flow, while we could get started with that track record of the original 5 LP Investments. 

Can you share more about the value proposition of offering your LPs access to the direct deals, given that Plexo can also invest directly into Plexo’s GPs’ deals?

Our GPs are mainly mentoring and investing in a company at the pre-seed, and GV, Intel Capital, Cisco are all downstream investors, investing at the later stage. There have been instances where we identify companies through our GPs that are interesting, and we might invest alongside our GPs at the pre-seed or seed, or we might invest after our GPs have invested. Usually, we try to not have our initial entry point be too far down the road for a company. We try to stay at pre-Series A/B (or below a $150m post-money valuation). 

At the same time, we’re trying to surface companies that might be interesting to some of our LPs -- GV, Intel Capital, Cisco Investments, even RBC to a degree. Most of our LPs are really Series B and C investors. We're completely happy if our LPs identify deals that are not a good fit for us or that are at a later stage than we like to participate in -- or, we can also invest alongside our LPs as well. 

We have actually done one deal with GV, Blavity. We surfaced Blavity, a media company based in Los Angeles, founded by former Intel executive Morgan DeBaun -- I think about it as a Huffington Post for millennials of color. We had been tracking that company at Plexo since the start. Two of our GPs had invested. We surfaced it to GV, which led the Series A. We (Plexo Capital) participated in that Series A as well. 

When you look at the criteria for selecting emerging managers, are you looking specifically at demographic criteria of diversity or are you looking at other factors as well? 

At the moment, we're looking for people who are not well represented in the venture community by ethnicity and gender.

I’m sure you’ve seen the stats from the work that Richard Kirby, formerly of Venrock, now of Equal Ventures based in New York, did. He has looked at probably over 1,500 VCs and he found, I believe, about 18%  are women, and I know that 3% are African American (2% African American men and 1% African American women).

We try to use the representation within the venture community as our way to determine who is underrepresented and use that criteria -- so it ends up being mainly people of color and women within the United States.

We also look at other geographies. We have made an LP commitment to a GP in Latin America. We have looked at Southeast Asia and the UK as well, though we have not pulled the trigger there yet. We are also looking at the continent of Africa, mainly sub-Saharan Africa, where we will likely pull the trigger. Our criteria remain the same; we're still looking primarily at GPs by gender or by ethnicity. We like GPs outside of the United States within local markets that are large enough to have good outcomes to give us the returns that we need from our LP commitments. We also like international GPs to have strong ties to the United States in the event that they do come across a company that has the ability to achieve global unicorn status, as those markets typically don't have a venture community with pockets deep enough to get those companies over the finish line.

It sounds like a lot of the GPs you’re evaluating are emerging fund managers. They may or may not have institutional track records. How do you evaluate performance or manager quality?

We are completely comfortable investing into a first-time fund. We do not like to invest or commit to first-time managers. So, with our model, it's very important for the GP to have a track record either as a result of the fund that we're evaluating being Fund II or Fund III, or from the GP coming from an existing shop where they have a verifiable track record. We have to be able to see the deals that they were responsible for sourcing, the deals that they were the lead on, the deals where they took a Board or Board Observer seat. Then we look to understand which firms  invested both before and after.

There have been instances where the GP may be at a first-time fund without coming out of an existing shop. However, they do have some type of verifiable track record; e.g, they could be a prolific angel investor.. Prolific angel investor does not mean having two investments of $5k each, though I encourage people who want to get a feel for investing to look at something like that as a start. What we like to see for an angel investor is investing in great companies alongside or in front of great institutional investors and being able to understand how that translates into the strategy that they would like to use for their first-time fund moving forward. So, it's very important for us to have a verifiable track record, even if not part of a prior fund, because it's part of our analysis and process that we use to understand the judgment of the GP.

And do you have a minimum allocation or minimum fund size? 

For the most part, we invest in sub-$100 million funds where the primary point of entry is pre seed or seed. If it's a sub-$10 million fund, we will typically invest a straight $500,000. If it's $10m-$100m, we look to make commitments of $1-5m dollars depending on the portfolio construction. Is it thematic or generalist? We factor all those things into the context of our overall portfolio, the impact on our projected returns, and the health of the portfolio. 

We like GPs who typically take leadership positions for the bulk of their investments. We do like commitments for follow-on. We will look at either a concentrated or a larger portfolio. It depends on the approach of the manager and really comes down to whether the funds are thematic or generalist. 

Like I said earlier, we will look outside of the United States. In fact, deciding to think globally at the outset was a critical decision. 

How would you define concentrated at the seed stage? 

It is typically 15-20 companies -- a very, very small number of portfolio companies. And typically, those are going to be ones where the GP is taking leadership positions.

We run across it more in thematic investors who are investing in a particular area such as enterprise or hardware. Even then, it kind of depends. I don't have a hard rule about the portfolio size for a GP. It really depends on the strategy of the GP and their network.

We spend some time looking at the sourcing network of the GP to understand if their network and background align with their approach. We want to see disciplined managers and make sure that they have a very clear portfolio construction strategy. The number one complaint of most LPs is strategy drift. We just like to make sure that when a GP says that they're going to approach investing in a certain way that they follow through and do that. That's the most important thing for us.

Tell me a little bit about what the process is for an LP to evaluate you. 

I'm in this interesting position because we do raise like a GP as well. At GV, where Alphabet is the sole LP, there was no true fundraising. Obviously, there's an annual meeting with the Alphabet execs and founders, Larry and Sergey, but it's different than actually going out as a GP into the market and pitching family offices, fund of funds, endowments, pension funds, etc. That was a new world for me, and since we do have this hybrid approach, the first thing we look for is whether we’re a good fit for the LP, given we do have corporate investors who have different motivations.

We do have normal institutional investors LPs as well. We've got a big large European family office that behaves much more like an institutional investor. They have a CIO and in their process for evaluating us, it was clear that they were looking for returns, but they were also very interested in being able to better understand the tech market in the United States at the seed stage. The family office wanted to get a feel for interesting GPs they could commit to directly. They saw Plexo as a very simple way to be able to make a commitment and really begin to understand the market and meet some of the interesting GPs in the market. We have made a number of introductions to GPs we have committed to, and some we haven't committed to, and the family office has made some commitments to some of those GPs.

We have also received a commitment from an endowment, Hampton University, which is where I went to school for undergrad. So I was very excited about that. Hampton is a Cambridge client and looked at Plexo purely based on returns. I don't think of Plexo as a fund-of-funds. I truly do think of us as a hybrid using a strategy of making commitments to GPs to get better access and get to direct opportunities that can provide great returns more efficiently.

I’ve learned that there is a certain view of the market around fund-of-funds, and it's the extra layer of fees. What's interesting is that if you look at the research that's out there in the marketplace, there's a good bit of research that the only place where it makes sense for the type of model that we have -- investing as an LP form a pooled asset -- is in the very early stage because of the power law nature of the returns. If you have the ability to pick the right managers, the data shows that you can actually have better performance by investing through an entity that's going to be focused on the seed-stage fund market with a deep understanding of the players and the right funds. The returns are actually better than the returns of investing in multiple later stage funds. Part of the reason is that the power law really doesn't exist at the later stage, so you get a normalized distribution. And because of that, you take a hit for the extra layer of fees.

Often, we will have conversations with LPs and we just won't be a good fit for whatever reason. What I enjoy is the ability to be able to say, ‘Well, Plexo Capital is not a good fit, but let me tell you about some of our GPs that are in the market that you should take a look at’ so both sides can leave every conversation feeling super productive. I've made a number of LP introductions for our GPs, in some cases for GPs who we haven't committed to but I know are interesting funds despite not being a fit for us. I know how hard it is to raise money and if you think about it from your perspective as a GP, what's the thing that's most helpful to an entrepreneur? At the end of the day, all an entrepreneur wants is customers, employees to build the product for the customers, and financing to pay the employees to build the product for the customers. This is very similar for a GP as well -- all a GP really wants is the LP commitment so that they can go out and find the entrepreneurs. So, if I can help with that, that's the biggest value add that I can provide. 

How do you think about things like succession planning? 

Super important. In my opinion, there are a few things that come into play.  Let’s say there is a situation where a firm started by a solo GP decides to bring in another professional, either as a partner or someone that can be groomed to become a partner. I’ll make a parallel back to GP investing when GPs invest into a company: a prospective LP needs to think about whether the new professional has enough economics in the fund they were raising to remain with the fund moving forward.  It is difficult to find experienced partners, so prospective LPs need to think about the risk of a junior partner being lured away by a larger firm.

In this sense, starting an early stage fund is similar to starting a company; the equivalent being how does a startup hang onto an employee when Google or Facebook could come knocking and pay this person a million dollars a year?

I had to have that conversation because that's the reality of our market: if you have good experience, you're getting headhunted every week. So that became an important conversation and a lot of the dynamics are again very similar to a start-up: Does this person have enough equity – or, in this case, carry -- for the economics to make it beneficial and worthwhile to keep this person long-term so that there can be a succession plan and handoff. 

Do you look at management company ownership? 

Management company ownership is important, but I'm really more concerned about fund ownership and economics. How much of the carry are they going to have in that particular fund?  That said, management company ownership is important to understand as it can really come into play if the partners decide to split.

Speaking of team, who else is on your team? 

I'm the sole GP but we do have four venture partners. We have Ken Coleman, a true luminary, who really is more of a sage mentor -- given us good advice, made great introductions, introduced us to one of our LPs. 

We have Georganne Perkins, who spent 23 years at the Stanford endowment working on their LP investments in private equity and venture capital.

We have Laura Alber, the sitting CEO of Williams-Sonoma, who is really amazing at understanding general business strategy and also tech infrastructure, given that Williams-Sonoma is an omni-channel retailer.

We also have Keith Walton, who is the administrative officer for an infrastructure fund out of New York.

They’ve all been extremely helpful. We also have a couple of interns -- an MBA intern and an undergrad intern. 

In the long term, I won't be the sole GP. I do want to build a franchise, but I'm going to be very patient in trying to find the right person because I've seen what happens when you don't have the right team in place. It's hard enough when you don't have the right team or founding team in a start-up. It's even more difficult when you have a partnership because it's very hard to untie and untangle that.

Where do you find your interns? 

I went to Haas, and I am a big believer in Haas MBAs in particular. I have consistently tapped into that network to find quality people. We also have an undergrad intern from Cal Poly Pomona who is studying computer science and business.

You mentioned this notion of a lot of funds wanting to have an underrepresented investor on their team, this concept of token hires – are you seeing a lot of this? 

I like to think there is a positive side to it, but without question, there may be cases, and I can’t say with certainty because I just don't know what's going on behind the scenes, where it may just be window dressing. Entrepreneurs ultimately have the power and we've seen some examples of entrepreneurs saying, “Hey, I went with this firm because they have the same values that I do. They have a diverse team and that was important to me.”

I think there are going to be some firms that are going to say,‘We better get someone up on our webpage. We don't want to miss out on deals now’. I don't like that aspect of it. But you never know. I like to focus on what happens when you get someone that's a woman, a person of color, and then they now bring in a whole new set of relationships giving access to deals and some insight that may not have been part of that firm historically. 

What are your thoughts on how everyone in the entire ecosystem can be more intentional about intersectional diversity? 

You have to start somewhere. When someone invites me to a diversity-focused event, I always have to ask, ‘What's your definition of diversity?’ Because I’ve been like, ‘Okay, I'll come to that’, and then it's just for women -- and just white women. I do think that’s just being aware. 

Soraya at Trail Mix told me about these calls that she does where she gathers female GPs to cover a specific topic on every call. To be more intentional about intersectionality, when it is time for questions, she puts women of color at the front of the line so that their voice has an opportunity to be heard. I thought, ‘Wow, now that is very intentional’. The fact that she had the awareness to do that said a lot to me. 

How long do you think it'll be until this is no longer something that has to be an actual focus area and it's just sort of the default?

I've been thinking about that since the day I first thought about the strategy for the fund. It would be great to make this model obsolete and then for us to transition and have a model that wasn't directly associated with diversity on the LP side.

Unfortunately, I think there's an opportunity for our model because you just look at the numbers and we're so far behind on the representation really matching the demographics of our society, especially here in the United States. So, unfortunately, I think this model is going to be in place for us for at least several funds.

There's another aspect of this which isn't our model, but we look at a lot of funds that have this model: GPs that focus on making investments into companies based on diversity. We're an LP in Female Founders Fund. Female Founders Fund focuses on companies where there is at least one female founder, just as the name implies. I always thought that one was interesting just because half of the population is half female, right? So yeah, I mean, you're going to see a lot. Female Founders Fund, for example, sees every deal that's worth seeing that has a female founder. I thought that was pretty compelling. Their performance has shown that when you match excellent investors like Anu with a market opportunity of half of the population that really gets overlooked, some magic can happen. There are also funds that focus on specific ethnicity. We haven’t made commitments to those type of GPs yet, but I understand why that's necessary when you just look at the low numbers of entrepreneurs of color getting funded.

I think that we're going to see these funds out here, but the thing that has to happen across the board, both at my level (the GP level) and at the entrepreneur level, is everyone has to perform. It's nice for Plexo Capital to have the impact of moving the cause along for diversity and inclusion -- but it's a much more powerful when the performance is there, right?

But if the performance isn't there, then what I get concerned about is, are we going to muddy the water? Even though in Silicon Valley it’s often said, ‘Hey, failure is fine’ -- I don't know how well that applies to women and people of color. 

So I'm hopeful that once people of color get commitments at the GP level and get funding at the entrepreneur level, they will go on to really excel in terms of performance because that's going to be the best way to show the power of this model. It's not going to be simply having demographic data that improves over time. We have to deliver the returns as well.