21. VC Portfolio Strategy (Rob Go)

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Rob Go joins Nick on The Full Ratchet to discuss VC Portfolio Strategy including:

  • Rob Go VC Portfolio StrategyWhat are the five main parameters that VCs consider with regards to portfolio strategy?
  • From your standpoint, what is the single best strategy that a VC firm can employ?
  • How is your portfolio strategy structured and why?
  • As you watch the portfolio of companies evolve through the fundraising stages and their lifecycle… what are your expectations of companies that will succeed vs. fail?
  • How do you handle capital calls?
  • What are your thoughts on specializing with a sector focus?
  • At a high-level, how are different funds often structured across a venture firm’s portfolio?
  • Do you think that portfolio strategies in venture capital has evolved in the past decade and, if so, how?
  • Have you seen any unique or non-traditional approaches to portfolio strategies emerge?

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Guest Links:

Key Takeaways:


1- The five main parameters of a VC Portfolio Strategy:
  1. # of investments
  2. % Ownership in each company in which an investment is made
  3. Amount of capital & staging of capital
  4. Capacity… How much time and mind-share does each venture professional have to contribute?
  5. Exceptions… When one breaks away from their chosen approach to items 1-4


2- Sector Focus
  • Sectors do come and go- they have a natural lifecycle like anything else and the time that a sector is venture-fundable is a small percentage of that sector or industry’s total lifecycle.  Here Rob advises that you consider the evolution of your sector focus areas to make sure that you stay ahead of the curve instead of falling behind it.
  • His second point here related to how broadly or narrowly the sector is defined.  As one crafts his or her angel or venture portfolio strategy, the amount of deal-flow that fits with focus area must be broad enough to see enough opportunities, while being narrow enough that one’s expertise allows these opportunities to be sufficiently and quickly vetted.


3- Three types of Opportunity Funds

  1. Follow-on opportunities from previous fund investments, where VC’s are using their pro-rata to maintain their percentage or attempting to increase their ownership.
  2. May do some follow-ons from previous investments but also will invest in new opportunities.  These may be companies that they decided not to invest in earlier-on b/c the economics or other factors weren’t a fit for that fund, but now would be a strong fit for an opportunity fund investment.
  3. Large opportunity funds focused on only late-stage, venture-backed, private companies.  And Rob did mention that some hedge funds & mutual funds, that typically play in the public market, are starting to move downstream to invest here.


Tip of the Week:   The Under-appreciated Exit

Below is the “Tip of the Week” transcript from the Podcast Episode 21: VC Portfolio Strategy (Rob Go): On this week's episode we touched on the timing of returns and faster time-to-exits.  We also addressed, on last week's episode, this notion of a binary outcome where a win is a unicorn investment with an out-sized return, and everything else is a loss.  I'd like to use this week's tip to discuss how, so-called "losses" from the portfolio, that experience an early-exit, can ultimately become enormous wins.  Many will talk negatively about investments that payback less than the capital invested, the same amount as the capital invested or even the modest, single-digit IRR returners.  While it's true that these also-rand investments will not make an angel's portfolio, as exits occur and capital is returned, this provides an angel more shots on goal.  Consider David S. Rose's comments from episode three.  He mentioned that five out of 10 angel investments will fail completely.  Two will return your money.  Two will be solid successes.  And just one will be (more…)Read More...

*Please excuse any errors in the below transcript

NICK: Today Rob Go joins us from Boston, Massachusetts. Rob is a cofounder of NextView Ventures, a seed investment fund focused on internet-enabled innovation, and he also writes great content over at the nextview blog. Rob, welcome to the program.

ROB: Hey Nick, thanks for having me.

NICK: So can you start us off by telling us your story about how you got involved in venture investing?

ROB: Yeah, sure, so I started my career on the operational side in product. I was at product in eBay 10 plus years ago in product marketing before heading over to the east coast for business school. While I was in business school I do some works with the startups in the area and had intended to either start a company or join a startup, but in the process, met a number of venture investors who had interest in bringing on somebody who had consumer internet experience for a large scale Silicon Valley company in Boston, so interviewed with a few groups an ultimately joined Spark Capital back in 2007 just as they were starting to invest their second fund.

So it was a terrific time learning the business at spark. They’ve obviously gone on to do extraordinarily well, and I was able to see the early investments in terrific companies like Twitter, Tumblr, and Admail and so forth. But also see a bare experience firm go through the ups and downs of the—mostly downs, I guess, of the financial crisis and subsequent recovery. So it was a great learning experience there.

And then partly that into starting NextView with my two colleagues David and Lee, who also have a similar path as being entrepreneurs and operators at high growth internet companies before joining more tradition venture capital firms. We just all saw a pretty common gap in the market around early stage investing where the cost of starting software businesses had come way, way down but ironically in the wake of the financial crisis, the best venture capital funds were actually getting bigger as a result of quality among the LP side, so there was this natural disconnect in the market that was most acute in Boston and the east coast.

And so, we saw a natural opportunity to start a very focused seed oriented venture capital firm here and that’s what we did. So we started the firm in about 2010, 2011 time frame and we raised a couple funds now and have been employing that strategy since then. 

NICK: So was there a specific focus when you’re at Spark, as far as sectors or geography?

ROB: Yeah. Spark as a firm is a multi-geography, multi-stage firm. They look broadly within the full value chain of tech and internet, so everything from application stuff to hardware and next generation infrastrucutre. My focus tended to be more on the application side of things and less so on the hardware side, but I was pretty broadly focused geographically in terms of specific sub sectors.

NICK: So you mentioned that you were at eBay, I think you said 10 years ago. What a time to be there during a major growth phase! What were some of the key things you were working on there?

ROB: I was the business product lead what we call finding, which was the features and functionality around helping buyers buy items and products on the site. It was an interesting time mot be there as you said because the company in many ways was going through an interesting transition when I got there where the balance in the marketplace had started to tip away from their being sort of an excess of demand in sufficient supply to a situation where there was excessive supply and not enough demand.

As a company, we didn’t have that many levers to improve the demand side of the equation, you could either acquire more users at the top of the funnel or you could make the users you got to the site more efficient, through the finding flow and so it was a remarkable time to be there because we were able to push through a lot of features and functionality that significantly enhanced at the time was a pretty rudimentary and pretty broken buyer product discovery process. So that was some of the interesting things that were happening then.

Apart from my own area, we were completing the integration to PayPal at the time, and so that was a strategically important time for the company from that standpoint as well. The two companies have separated, which is probably the strategically correct thing at this point for the PayPal business.

NICK: I’d imagine that your portfolio companies appreciate that advisor perspective, but all right, the topic today is VC portfolio strategy. Rob, you think of five main parameters that VCs consider with regards to portfolio strategy. Can you walk us through each of these?

ROB: Sure, and these five are not independent. They tend to tie together in a pretty tight way. The first could say is number of investments. You can think of this in two ways—both the number of investments for the fund as a whole, as well as the number of investments on a per investor basis, which tie together. The second is the ownership percentage that you’re targeting as a firm in those companies, so essentially it’s a measure of how meaningful every one of those investments if they are successful.

The third is the—I’d say the concentration in the staging of capital. So how much of your fund’s capital goes into any one company, and at what point in the life of the company does that capital go in? There are some firms, for example, that put in a relatively small amounts of money at the seed stage, but then at the A and the B stage, they really heavy down. If you look at the percentage of their capital going into the companies, the vast majority of the capital is in the A and B stage, or later, but not so much in the early stages.

So it’s a concentration of staging. The fourth is capacity, I think of this is as the human capacity of the firm. If you’re making 10 investments per year, per partner, that’s a very little capacity per company or an individual partner. If you’re making one investment or two investments per partner, that’s a large amount of capacity and so the partner can allocate their time based on that.

The fifth is a catchall, which I just call exceptions, because every firm has a broad strategy, but every strategy has exceptions, and rules are broken all the time so I think there’s both the question for what is the tolerance for exceptions within a firm’s portfolio strategy, and what are the conditions under which an exception is allowed to occur.

NICK: I wanted to circle back on number one. We had five total, first was number of investments, second was ownership percentage, third was concentration in staging of capital, fourth was capacity and five was exceptions. On that first one, you mention that the number of investments can vary by fund and then you also per investor. I didn’t quite get that second part, could you elaborate on that?

ROB: Yeah, so the second part actually ties to the capacity issue. The simplest example is a one partner firm. If the one partner firm is investing in two companies per year, which is what a typical life cycle VC does, and invest over three years, that’s six companies in the entire portfolio, and that’s probably not enough diversification for it to work. You kind of have to think about both levers at the same time.

On the flip side, if you have a firm with six partners and you have a model where each partner does five investments a year, six times five is 30 investments a year, across three years, that’s 90 investments. Is that too big of a portfolio or not? Unclear, right? So I think the two are related but they’re both somewhat different considerations.

NICK: And then on that second point, ownership percentage, is that related to a specific strategy VC firm may have about how much equity of a target startup they need to own in order to make a placement?

ROB: Yes, it is, and a lot of these are around thresholds, so there’s some level of ownership where a VC says it’s just not worth our time or our capital to invest in this company because it’s not meaningful enough to us. But then the question is what does meaningful enough really mean? For whatever reason, historical threshold for most of the venture industry has been in the 20 to 25 percent ownership threshold, so that’s been sort of the historical target.

With seed funds, often the ownership is quite a bit lower but different funds employ different strategies. In our case, we usually look to own roughly seven to ten percent of the companies that we invest in, other funds own less, some funds may target owning more. The way to think about this is your ownership target as a fund is directly related to your fund size. I like to say let’s think about a particular outcome. So say a 300 million dollar exit for a company.

If you’re a 40 million dollar fund, and you own 10 percent of the companies, that 300 million dollar exit returns 30 million bucks which is 75 percent of the capital fund, that’s pretty good. If you’re a 300 million dollar fund, and you’re targeting 20 percent ownership, that 300 million dollar exit return, 60 million out of your 300 million dollar fund, that’s not as good, right?

While a big fun may own more, the ability for an exit to impact their portfolio might be much less if that fund is much more larger. So what I found curious actually is for the larger venture capital funds, you don’t see a relationship with the larger the fund gets, the bigger the ownership needs to be, even though it kind of intuitively should be the case because you’re a billion dollar fund, and you’re owning 20 percent of those companies, a billion dollar exit is only returning 20 percent of your fund whereas if you have a much smaller fund, you still have the 20 percent ownership. You lose the needle much more significantly, so it’s an interesting dynamic there.

I just think that the market doesn’t tend to bear more than 20 25 eprcent ownership for venture capital fund unless they participate in a financing where there wasn’t as much competition or the firm was able to write a huge check and maybe give liquidity to founders or something.

NICK: So you go on to cite the single best strategy that a VC firm can employ, sort of from a theoretical standpoint? What is that and why is that not the strategy used by most VCs.

ROB: Right, so I don’t think this is particular to VC, I think it’s pretty much at any sort of investment where the single best strategy you can employ is to invest in only one  company, and to invest in the company that has the biggest outcome and invest as early as possible at the early evaluation. If you can invest a 100 million dollars into FaceBook’s very first round, that is better than any portfolio strategy or any other invest you could possibly make, right?

I’m sure—it scares me now, but Warren Buffet talks about this where having concentrated positions is infinitely better than diversification if you actually believe that you employ good selection and your investment actually makes a difference. So obviously there’s way more risk in the market to be able to invest in just one company, and so investors need to build broader portfolios. My argument is the larger the portfolio one builds, the more one essentially admits there’s luck and chance in what one is doing. The reason why you’re investing in company N+1 is because you think that what you give up in terms of the size of your position is made up for by the fact you get the benefit of having one more shot on goal.

And again, different funds have different perspectives on how many investments to make, how large portfolios are to build. It’s been a guiding principle for me ever since I’ve heard the concept of the single company portfolio. If we’re investing in tons and tons of companies, that’s essentially saying we can’t outfox the impact of luck and chance and so we need to build diversification, but with diversification potentially comes dilution in terms of the impact of any one company.

NICK: Yeah, we recently had Jerry Newman on the show and he was talking about how essentially you can’t pick. You can’t pick these unicorns. Eileen Lee’s article illustrated that venture back companies, I think it was 0.7 percent end up being unicorns. Maybe we can touch on that a bit later. So along those five dimensions of VC portfolio strategy that we discussed before, how was your fund structured and why?

ROB: I’ll go through each. So number of investments, our fund focuses on making about 30 investments per fund on a per partner basis that equates to 2-4 investments per year, per partner. Our target ownership, as I mentioned, is in the 7 to 10 percent range. Our concentration in staging of capital is fairly front loaded, where roughly a third of our capital will go into the seed rounds of these companies, and the reserved capital is there to maintain our ownership in the companies that are performing well over time.

Capacity wise, we look to be very highly engaged in the companies we invest in, and part of our mantra is we’re one of the most highly focused investors at the seed stage, where we leave most of our rounds and we will often take board seats. The two to four investments per year, per partner allows us to do that. The way we manage capacity longer term is that we tend to stay on the boards of these companies through the seed round but come off during the series a round. At any one time, we may be on five to eight boards but there is a natural flow to that activity where we’re either coming off of boards where companies are progressing beyond our stage, or there’s natural attrition in the portfolio.

In terms of exceptions, we’ve actually had extraordinarily few exceptions, and again I think that comes down to our strategy as a firm where we look to be one of the most deeply focused funds in the market. We think about this concept of the one company portfolio all the time, and so when there’s an exception, usually the temptation is to say, well, why don’t we throw 100k into this one company that’s a flier, or invest at this company that’s a ridiculously high evaluation and so we can rake in the ownership we want.

Usually the reason why we don’t end up making those exceptions is because we believe that every investment we make needs to be dramatically meaningful to the fund and have something about the investment that would make it the theoretical one investment that returns all of our capital and then some. If our dollar runs too small, or the evaluation is too high, there’s essentially no possible away that could realistically happen so we make very few exceptions.

NICK: So is there one fund that handles both the seed investments as well as the follow ons?

ROB: Yes, it’s all one fund. Pretty standard. Most venture funds have capital that they invest in initial rounds of financing in the companies they invest in, and there’s also reserves allocated towards those companies down the road.

NICK: Depending on who I’m talking to, it’s structured either one or two ways. Either the way you’ve got it or for instance, Charlie O’Donnell was talking about how he has raised a seed fund and will deploy that on the seed investments but raise a subsequent growth fund which he uses for following on the winners.

ROB: One comment in that I would say, you have seen a wave recently of opportunity funds that have come about. Those tend to be designed for much later stage investing, so Foundry, for example has an opportunity fund. Their core fund does do quite a bit of their follow on investing out of their main fund, but the opportunity fund is for the minority of opportunities within the portfolio that raise a very, very large later stage rounds which they think is still attracting buying opportunity and so the opportunity fund is focused on that.

I would say the vast majority of funds have reserve capital as part of their core strategy and the opportunity funds are even on top of that.

NICK:  As you watch the portfolio of companies evolve through the fundraising stages and their life cycle, what is your expectation of companies that will succeed versus fail?

ROB: The rough math that we expect is if we invest in 30 companies, 10 of the 30 will essentially fail out of the gates, so they won’t get to a subsequent round of financing nor will they be acquired profitably after the first year, year and a half. So far our numbers have tracked pretty low of that, something like 70 percent of our seeds end up raising VC lead series As and so we’re a little bit ahead of that number but that’s roughly what we model. Of the remaining 20 companies, another 10 will lose money down the road, it just won’t happen as quickly, and that leaves 10 companies that leave money for the fund. The reality is that though call it 1 to 4 companies will probably drive the vast majority of the returns, and so the success of this fund is driven by how many of those we have and how big those outlier investments end up being.

The good news is, I think I mentioned earlier, given that our ownership relative to our fund size is pretty favorable is that the definition of a big fund returner for us is much, much more manageable than for a larger fund. For it to be a needle mover, it doesn’t need to be as big, but if there is a huge needle mover, it really moves the needle and the potential for a really big multiple in the fund is there.

NICK: I’m curious, I’ve talked to a range of people about capital calls and how some smaller funds will call all the capital up front. Others will establish certain tranches at fixed time period at which they call, and even others will call as it’s needed. How will you guys handle the capital calling process after an LP has committed a certain amount?

ROB: Our fund structure is of a typical institution venture fund, so the LP is a whole commit to a certain amount, and that happens for us on a 3 year basis for the most part. Essentially what we tell our LP is we’re going to tell capital on a quarterly or three times a year basis. It’s not a set schedule because it tends to be set on the visibility we see in the portfolio around new investments, follow ons, and so forth. But it ends up being reasonably consistent, right? It’s not like we’re doing one huge capital call and nothing throughout the course of the year. It’s relatively consistent over the act of investment period.

We work with VSP that provides a line of credit as well that is there just to smooth out the capital call pacing, so if we miss, estimate our timing a little bit, our LPs don’t feel like they’re getting many capital calls all on top of one another, unexpectedly.

NICK: Earlier, I mentioned the interview with Jeremy Newman where he advocated a non unicorn picking strategy of sector focused investing. What are your thoughts on specializing with a sector focus?

ROB: Yeah, I think it’s an interesting strategy. There are two things I would be thinking about if I was highly sector focused. The first is that sectors come and go pretty quickly. And so, to some degree if you have a high degree of conviction around a certain sector, and you’re right, it’s great. But unusually that same sector isn’t producing great, great companies year after year for a long, long time.

So I would think about how do you evolve that sector focus as different sectors arise and become more or less interesting. The second thing I would think about is how broadly or how narrowly you would define the sectors, right? Because the fund example nowadays is every internet company, or many internet companies have a big data element, so it’s not that meaningful but the flip side is if you’re data confused, it’s very good at positioning yourself relative to other investors. It’s very good in terms of helping you develop more new sub theses in certain areas, and so it’s not a bad strategy, even though it’s very broad. So on the flip side if you say, hey, we’re a fund that’s completely focused on block chain, the block chain protocol, then that is probably prohibitively narrow, and you get lucky, but at some point there’s just not that many extraordinary companies that you can build a great a portfolio around. If you look at the broad arch of venture, funds that have some focus but not too much focus tend to do the best.

Sequoia is not that sector focused as a fund, although different partners in different points in time focus on certain areas and go very deep and make investments and then move onto the next one. Funds like union square or other funds, they’re tech focused, software oriented. They have a thesis around network effects, or something like that, but if you look at they actually invest in, it fits those thesis areas, but those thesis areas are necessarily broad and I think it’s affective for them. At the same time, they’re not investing in biotech or material science or things like that because they know that that’s well outside their range. There’s some goldilocks amount of focus that I think is appropriate and I think that our approach for better or worse is that once you narrow us down in term of being seed only, software and internet, and predominantly east coast, that universe feels like the right scale of a universe for us to be able to compete pretty effectively without needing to explicitly be singularly focused further.

NICK: So earlier we talked about how fund managers at a venture firm may specialize in a sector, or maybe they specialize in a stage. So, there’s a fund manager who just does seed investments or we discussed opportunity funds or growth funds. Can you talk about how typical venture firms structure their broader portfolio of venture funds?

ROB: Yeah, so typically a venture capital firm has a set of limited partners, so these are the investors within our firm, and we raise specific funds, to employ a strategy. The simplest example is a venture capital firm, let’s say a couple partners, they do early stage investing, they raise a fund in 2011, they start investing that for a few years, then they say hey, we’re going to keep doing this another time so they raise another fund in 2014 and then they keep going. Each fund that’s raised may have different investors but usually, a large portion of the investor base of those different funds are the same over time.

The next question is okay, that’s fund one, fund two, fund three, fund four of a certain firm, what if there are other sort of types of funds that emerge?

In some cases you have firms that create growth funds or opportunity funds, and I think in each case these start to get a little bit different, but I think for the most part, those funds are made of the same LPs of the core funds who’ve bought into the concept that, yeah, we’d love more exposure into the companies in this portfolio, we trust these managers, and so we’ll allocate more dollars to this slightly different strategy for this team or maybe for this team plus one other new team member and they come from there.

In that case, I would expect that most to the LP capital is still pretty similar. It’s from the same groups of people, but maybe not 100 percent.  Then you have situations where there are sub funds that have different strategies or different focus areas. So everything from Kleiner Perkins that announced a few years ago—it was a number of years ago. There was a big data fund, an iPhone fund to firms that start to create international funds that share the name but is a different investment team.

Those relationships, economically and in terms of the LP commitments, those vary across the board. In some cases, I would imagine that it’s actually not a separate fund. It’s actually an initiative within the safe fund that’s been gear marketed for a certain type of investing. In some cases, it’s a completely separate team where the mother ship essentially lends their name and their LP relationships and some of their oversight employing a different strategy, and it’s essentially a separate fund with some shared economics. But I can’t really speak for the specifics because it’s not something I’m that familiar with.

NICK: I’m curious about some of these later stage opportunity funds. As the nature of startups in the private market has evolved and now we’ve got these massive companies like Airbnb that are very late-stage. Is there sort of a new era of very large late stage opportunity funds that some of these venture firms are raising so that they can maintain their parade [25:54] in what are much larger private companies that are staying private longer?

ROB: Yep, I think there’s sort of two flavors of opportunity funds. I’d say there’s three flavors of these funds. One is an opportunity fund where the investor invests only in the companies they’ve already invested in, with a prior fund, but follow on opportunities. So that’s one model. I believe boundary group takes on that strategy.

Then there’s another type of opportunity fund that says we might do some of that but we’ll also invest in completing the new companies, right, where a firm is a series A and B investor typically, and they say you know what, there are a couple companies that we missed. We could have invested at the series D, but the economics didn’t make sense for our main fund, so we’re going to raise another fund to be able to go after those types of opportunities, which I think is actually quite different than the first instance.

I believe union square’s opportunity fund is more like this. I believe spark’s opportunity fund is more of that profile. And I think the third is one of the things you eluded to, funds and firms that are focused entirely strictly on later stage investing. That’s all they do. it’s not that they do early stage investing, and they have pro router rights they want to capitalize on, it’s just funds that say, you know what I think that with private companies staying private longer, the public markets are not well equipped deal, nor are founders interested in going public too early.

There’s this opportunity for companies of a significant scale but aren’t ready to be public companies, but are also too large to ever be acquired at an attractive evaluation, so there should be a capital source for those types of situations and I think tiger global does a number of these type of deals. A lot of the hedge funds, sometimes mutual fund companies and so forth are coming downstream to make these kinds of investments, and I presume that there are some dedicated funds that specifically go after this opportunity as well.

NICK: Rob, do you think portfolio strategies in venture capital have evolved and changed in the past decade, and if so, how do you think they have?

ROB: That’s a good question. I don’t think I’ve as much experience over the longer arch of time as some of my other compatriots in the other industry, but my two cents is that it probably has, especially on the software side of things. I think if you look at the data, the bifurcation in the scale of the exits has become greater, and so the big exits are bigger and they’re more plentiful, but there’s just more plentiful companies over all.

As a result, I think what we’re seeing is there is a little bit more—I think investors are seeing more of a benefit to expanding the size of their portfolio. You rarely see funds that have 25 companies, 20 companies in their portfolios, instead it’s more and more common to see funds that have pretty large portfolios because they realize even though you’re diluting the impact of any one winner, the size of the real big outliers are so extraordinary is that it’s worth stretching to make room for those and have more shot on goals, so to speak.

I think that’s a broad trend.  I think that the jury is out actually of whether that’s oging to prove to be a better strategy or not, and I don’t think anybody’s ever done much of an analysis on portfolio sizes of funds over time, so it’d be really interesting to do that analysis and see how that correlates with performance at all.

NICK: Yeah, I’ll have to do some searching to see if I can find any studies on that. I’ve just noticed myself with discussing with angel investors and doing interviews is a lot of these angel investment portfolios that have existed for decades, have sort of an average time to exit from investment to getting your money out of somewhere from 9 to 11 years, I say. And then you read Eileen Lee’s article, and the average time to exit from founding to exit was 7 years, so that’s not even a date from when it was venture back to exit. Certainly the companies in that study are in the software spectrum, but I have to think that a quicker time to exit does impact portfolio strategy not only that IRRs and returns are going to be higher, but if you’re getting that money out, you have the ability to make more bets, or your LPs can reinvest faster.

ROB: The other thing that’s specific to seed funds is because we’re investing relatively early, there’s a cohort of companies that build value but it’s not necessarily a great risk adjusted situation to try to build a huge, huge company. You see exits in the 20 to 75 million dollar range to 100 million dollars range, for companies that are relatively young, have relatively modest business metrics, but might have really interesting scale in other dimensions or strategic value, and those are situations that could be return for the seed investors and build really nice foundational returns relatively quickly, and so that certainly happens, but for the most part the big value drivers are built over time.

You’ll always have exceptions, like the Oculus’ of the world or the Instagrams, but by and large the multibillion dollar companies are built to real businesses and that just takes time to develop. Companies like Wayfare, Hubspot, two companies in Boston that just went public and are really strong business. Dropbox will be that. Airbnb. Those are companies where if they had sold out early, they would have been leading a lot of value on the table, because there was truly a big independent promising company to be built there, and so I think we’re all ultimately beneficiaries of the fact that they decided to build rather than try to flip or get a grade IRR sooner.

NICK: So I’m curious with your peers in the venture community, have you come across any unique or non traditional approaches to portfolio strategy?

ROB: That’s a good question. So I think in the seed side, there is definitely—there’s a cohort of investors who invest very, very broadly, so they invest in a very large number of companies, and their thesis is that even though you are essentially building an index of opportunities, their slice of index will outperform long term for a bunch of different reasons.

There are firms like Lerer Ventures in New York for example or Dave McClure, who take the strategy and it’ll be interesting to see how those play out, and both investors are involved with some really mature companies through that approach. There’s another fund called Thrive in New York which I also appreciate in that their strategy is to be completely opportunistic.

They really don’t have a specific focus around late stage or early stage geography or much of sector focus or return focus. Their whole sense is they’re buying great assets, and great assets come in different flavors and they have a fund size and strategy that is able to be very, very opportunistic. That’s a completely different approach from the venture mindset where there’s a very tight definition around what they do, but so far they’ve been doing really well as well. I think those are a couple examples of different approaches to portfolio building recently that I’ve seen.

NICK: Wow. Personally, I can’t imagine trying to evaluate such a range of different investment opportunities, but I guess that’s why I employ the strategy that I do and they what they do.

ROB: Yeah. You have to do what’s a fit for your own temperament and the way you think about the world. Can’t fault people, everyone has a shot at being successful, so I try not to judge too much.

NICK: Yeah, right. So Rob, what are you currently most focused on?

ROB:  We’re focused on a bunch of different areas. I’d say a couple subsectors we’re excited about, one is labor market places, so I think that there’s really been a revolution in the way that people work and how technology has been enabling that and so we’re fascinated by that. We’ve made a couple investments along those lines, but I think there’ll be many opportunities to come.

The other area is around the connected device ecosystem, the proliferation of internet enabled devices and the broad range of applications has been pretty extraordinary in both the consumer and be to be side, and so we think that there’s a lot of exciting individual devices through applications, but we also think there’s a lot of enabling technologies and pick and shovel businesses there that could be exciting as well to draft on the overall trend.

The third area is around companies that employ what I’d say certain algorithmic decision making. Historically, one of the nice things about big data is that it allows you to process huge amounts of information in real time and augment human decisions, and we saw verticals like ad tech because completely transformed by that, so we’re thinking about what are the other verticals, which exhibit similar characteristics of high velocity, large scale data, to drive real time decisions. I think we’re seeing that happening in many, many areas of the market, so that’s a different lens we also look at.

NICK: If we could cover any topic in venture investing, what topic do you think should be addressed and who would you like to hear speak on it?

ROB: That’s a good question.

NICK: Yeah, I’m trying to give you the difficult ones here. Haha!

ROB: Yeah, right. I think the portfolio size question is a really interesting one that we talked about earlier. The question of how have VC funds portfolios changed over time and how is that tied to performance. I don’t know if the recent data is complete enough to draw conclusions, but that’d be really interesting. Although I’m not sure who would have the purview to drumming conclusions there, but I think that’d be really interesting.

It’d be interesting to hear from someone, say at IVP or Tiger at late stage investing and talk through how they think about portfolio strategy and exits and the frothiness of the market at that stage and what they’re doing about it, I think that’d be pretty fascinating as well.

NICK: So Rob, what’s the best way for listeners to connect with you?

ROB: The best way is through e-mail. I’m Rob@NextViewVentures.com I have a blog, RobGo.org, which I’m active on and you can follow me on twitter @RobGo.

NICK: Rob, thanks so much for the time today for this insight on VC portfolio strategy.

ROB: Great, thanks very much Nick, appreciate it.