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Posts from the ‘Venture Capital’ Category

Challenges of Being an Executive in Residence (EIR)

This is the fourth post of a multi-part series on being an Executive in Residence (EIR). The initial post outlining the full series can be found here. The previous post was “How do you get an Executive in Residence (EIR) role?

If you’ve made it this far in my Executive in Residence series, you might be thinking, “This job sounds like a dream come true.  What could be better than a role where I’m working with intelligent people, meeting brilliant entrepreneurs and given time to think carefully about my next company?”

I’m a big fan of the Executive in Residence (EIR) role, when it’s taken for the right reasons and with the right firm.  That being said, the EIR role is one of the more unstructured positions out there, and can easily lead to an unproductive outcome for both the executive and the venture firm without the right perspective and motivation.

Time Management

There is no question.  The biggest lurking challenge around being an Executive in Residence is time management.

For an operating executive or CEO, you likely have gotten used to the implicit structure imposed by running an operating business.  There are people and teams who report to you, guidance you give regularly on talent and strategic decisions, key results you are responsible for.  If you’ve worked for a company of any scale, your biggest issue previously was likely paring your calendar back regularly to give yourself time to think.

You know what greets you as an EIR on your first day?  A calendar full of empty.  More importantly, while there are meetings all the time, you aren’t actually required for any of them.

As a product manager, it’s second nature to think backwards from your goal, and create a set of milestones and checkpoints.  As an EIR, I’d recommend thinking about the following milestones, within a rough timeline of one year:

  • What’s your investment thesis / area of focus?
  • Are you going to be an investor or an executive?
  • Are you going to start something or join something?
  • Are you going to look at companies outside your firm’s portfolio?
  • What stage of company and role are you looking for?

Investment Thesis & Focus

The first thing that happens when you join a venture capital firm is that you realize the world of successful startups is much broader and more diverse than you thought.  This goes beyond simple descriptors of “consumer” and “enterprise”.  Given your unique experience and skills, you may find yourself fascinated with marketplaces, collaborative sharing, mobile communication, next generation CRM, big data infrastructure.

The problem is, no one can be deep on everything.  It’s all too easy to find yourself broadly exploring an ever increasing number of sub-segments, business models and industries.  In a partnership, you’ll find that every partner has levels of expertise and exposure on multiple domains.  As an EIR, you could potential spend time digging into any one of them.

Some of this is good, to be sure.  One of the perks of the EIR role is the time and access to broaden your horizons.  However, the challenge for an EIR is that, in a limited time frame, you have weeks and months to explore, not years.  Most successful EIRs come to an opinion fairly quickly (within 6-8 weeks) of the rough dimensions of the currently exciting areas of innovation to focus on.

Investor vs. Executive

Being at a great venture capital firm inevitably forces even stalwart operators to ask the question of whether or not they want to be an investor.  Most likely at this stage in your career, you’ve already started to take advisory roles or participated in seed rounds as an angel investor.

EIRs rarely transition to investing partners, but it happens more often than you might think.  (Most recently, Simon Rothman transitioned from an EIR role to a general partner at Greylock).

The real issue is one of time frame and priorities.  In the end, the process that investors go through to evaluate companies and opportunities has very different dynamics than finding a good fit for a CEO role.  While most EIRs have this internal debate at some point, the sooner you can resolve the issue with confidence internally, the sooner you can optimize your efforts towards a successful outcome.

Let’s face it: defining success is a big part of achieving it.

Entrepreneur vs. Executive

Alright.  You’ve figured out your investment thesis and areas of focus, and you’ve got confidence now that while you respect venture capital quite a bit, you’re an operator.  The next challenge that rears its head: are you sure you don’t want to start something yourself?

Meeting with successful, passionate entrepreneurs day-in and day-out does a funny thing to you.  It’s addictive.  Their energy is tangible.  And when you work with a great firm, more often than not, you meet superlative entrepreneurs, many at later stages of company development, proving that not only can it happen, it actually happens more often than you thought.

In my first post, I tried to explain the differences between an entrepreneur-in-residence and an executive-in-residence.  As it turns out, however, at most firms, there is a lot of flexibility around this issue.  At least in Silicon Valley, no one is going to talk you out of building something from scratch if you get set on doing it.

I hate to be cynical, but watching a number of colleagues go through this, the pattern is fairly predictable.  The reality is, most people actually have the answer to this question before they start their role as an EIR.  What actually happens is that EIRs tend to forget this fact quickly, spend some time debating it internally, and then realize that their initial assessment was correct all along.

Navigating Firm Bias

Another challenge that confronts EIRs is firm bias.  By taking a role with a specific venture capital firm, a number of questions are raised:

  • Will you only look at companies that fit the firms / partners current investment thesis?
  • Will you only look at companies that the firm has invested in?
  • Will you engage with recruiting partners from other firms or third parties?

Underlying these questions is an implicit misalignment between the EIR and the firm.  The firm is investing time (it’s most precious resource), reputation and knowledge with you.  At the same time, as an EIR, finding the right fit of company, stage, product, team & timing for a CEO role is exceptionally difficult.  Spreading the net as far as possible definitely can increase chances for a successful fit in a given time frame.

For most EIR roles, the answer to these questions is best resolved directly, with the firm, before joining.  Personally, I was fortunate enough to be an EIR at Greylock Partners, where the firm’s perspective was that any area or company that was interesting enough for me to engage with was by itself a strong vote of confidence.  Greylock is one of the oldest and most successful early stage venture capital firms, and sees its network as extending, through people, more broadly than just to the specific companies where they are currently invested.

By the way, for this reason, it’s not unusual to see EIRs split their role between two firms, just to signal strongly to both the firms and the outside world that they are not committed to a single firm.  While I don’t believe this is necessary for a successful EIR role, I do personally recommend that EIRs broaden their network to companies and opportunities beyond a single firm.

Company Stage & Role

This might be one of the biggest challenges an EIR faces in their search.  What are you actually looking for?

  • Are you interested in a startup that is pre-product/market fit?  Or do you operated best when product/market fit has been established?
  • Do you add the most value at a 20-person company going to 100+, or a 300 person company going to 1000+?
  • Are you willing to consider a COO role, or only a CEO role?
  • Will you consider GM roles or functional leadership roles at larger companies?

To some extent, you have time to entertain and consider a wide variety of roles.  There is significant learning, both about the company and yourself that takes place when you engage on a potential role.  That being said, spending time on roles you are not inclined to actually take is expensive, for both you and the company.

Tell Us Your Story

In the previous four posts, I’ve tried to remain objective and incorporate lessons from other EIRs that I’ve had the opportunity to both know and work with.  Due to popular demand, however, my final post in this series, Did you like being an Executive in Residence (EIR)?, is coming up next.

How Do You Get an Executive in Residence (EIR) role?

This is the third post of a multi-part series on being an Executive in Residence (EIR). The initial post outlining the full series can be found here. The previous post was “Should I be an Executive in Residence (EIR)?

One of the most mysterious aspects of the Executive in Residence role is the relative obscurity about how these roles come into being in the first place.  After all, you’ll never find a job posting on LinkedIn for an EIR, and as a result there is no obvious description of the requirements or the process to get one of these roles.

However, a simple search on TechCrunch or Pando Daily reveals a fairly regular stream of people joining top tier venture capital firms as Executives in Residence.  How did they get that role?

Relationships Matter

Venture capital partnerships value relationships, and so it’s rare that you’ll find an Executive in Residence that doesn’t have some direct relationship to the firm that brings them onboard.  The three most typical ways executives form these relationships are:

  • They were an executive or founder at a company backed by that venture capital firm.
  • They worked with one of the partners at the venture capital firm in a previous operating role.
  • They sat on the board of directors of a company with a partner from that venture capital firm.

There are of course exceptions to these examples, but in most cases the most likely way to get an Executive in Residence role will be from one of the venture capital firms that you’ve personally worked with in the past, where they have a high opinion of your capabilities as an executive, your relationships in the entrepreneurial community, and your expertise in an area that the firm has prioritized.

Situations Matter

The Executive in Residence role is typically opportunistic in relation to timing.   There is some event, some inflection point where a talented executive ends up potentially free from an existing role, and yet will be looking for time to assess the market and decide on their next operating role.

The most common events that lead to this situation are:

  • Acquisition of a company. During acquisitions, executives either leave on completion of the acquisition or after some reasonable transition period.
  • Reorganization of a company.  As companies grow, they periodically will hit strategic shifts or management inflection points where it makes sense for some executives to leave the company.
  • Long tenure / Company size.  Sometimes as companies grow, executives who prefer earlier stages of company culture and growth will decide they want to pursue a role a new startup, but don’t necessarily have visibility into the full field of opportunities.

Once again, while there are exceptions to the above, you’ll find that almost all Executives in Residence come from a situation that generates a need to leave their current role, without sufficient time for the research and match-making process involved in placing a CxO.  These situations can also generate the catalyst for a venture capital firm to take the opportunity to deepen their relationship with a talented executive.

Reputations Matter

In the end, venture capital firms bring on Executives in Residence in order to bolster both their access to talent as well as their relationships in the startup community.  As a result, the reputation of the executive matters quite a bit in terms of getting an offer to join a firm as an EIR.  Common attributes are:

  • An executive with a well known reputation, or strong ties to a recent, well-known successful venture-backed company
  • An executive whose reputation will be compatible and additive to the brand of the venture capital firm
  • An executive whose existing relationships in the technology community will be compatible and additive to the venture capital firm.
  • An executive with expertise in an specific market or technology sub-sector that the venture capital firm is strategically interested in going forward.

You Don’t Ask, You’re Offered

The Executive in Residence role is, by its nature, a fairly opportunistic hire on the part of the venture capital firm.  If you are a founder or executive at a venture backed company, and one of the situations described fits your condition, make sure you are investing some of your time in relationships and being “top of mind” with venture capitalists you’ve worked with.

My next post in the EIR series will attempt to answer the question: “Challenges of being an Executive in Residence (EIR)

EIR Series: Should I be an Executive in Residence (EIR)?

This is the second post of a multi-part series on being an Executive in Residence (EIR). The initial post outlining the full series can be found here.  The previous post was What is an Executive in Residence (EIR).

The most common question in relation to the Executive in Residence role has been a simple one:

Should I be an Executive in Residence?

The truth is, when people ask me this question, they are very often asking two similar, but different questions:

  1. Is the Executive in Residence Role a good opportunity?
  2. Is the Executive in Residence Role something I should pursue?

The answer to the first question is fairly simple, but it has an over-arching caveat.  Like most things relating to venture capital, the quality of the partnership that you’ll be working with and the expectations of that partnership around the role are paramount.  As long as there is strong alignment of expectations between the partnership and the executive about the expectations for the role, the Executive in Residence role can be a unique and fantastic opportunity.

The second question, however, is much more complicated.  And that’s because it implicitly brings up some of the most difficult career questions we have to ask ourselves.

What Do You Want From an EIR Role? 

Last year, John Lilly wrote a simple blog post about leadership and the key questions to ask when you’re asked for advice.  If you are at the point in your career where you are qualified to be a CEO, then the question of what you want from your career becomes increasingly dominant.

What are you optimizing for?  Is it passion for the product you’re building, particular technology or a target market?  Are you looking for a particular business model, corporate culture or lifestyle? Are you looking to join the ranks of the Forbes 400?  Are you looking for power & influence and if so, in what industry / sector?

These questions can become increasingly difficult as you progress in your career because to be uniquely qualified to lead a company, there needs to be incredible alignment between your values and goals, and the goals of the company you want to lead.  Put another way, matchmaking for the right company actually requires a deep understanding of your own motivations, values & priorities.

Benefits of the EIR Position

The Executive in Residence role offers a lot of unique benefits.  These include:

  • Create, Build & Grow Relationships.  It’s an incredible opportunity to make new relationships, re-establish dormant relationships, and deepen existing ones.
  • Broaden & Deepen Your Knowledge of the Market. When you are in an operational role, you tend to become extremely deep on the companies related to your market and space, and tunnel vision sets in.  The EIR role gives you the opportunity to explore a much wider range of product categories and sub-sectors, and learn more deeply what strategies and tactics have been successful outside your specific niche.
  • Learn about New Companies.  We all like to think that we’re in the flow of knowing the important, successful private companies being built in Silicon Valley.  The truth is, there are a shockingly large number of amazing private companies that you haven’t heard of.  The EIR role gets you fantastic exposure to a large number of companies you haven’t heard of.
  • Platform for Thought Leadership.  Top tier venture firms have great reputations, and EIR roles offer a unique opportunity for you to nurture, develop & grow your own reputation around specific topics and issues.  The venture firm benefits from its association with thought leadership, and the EIR benefits from its association with the firm.  The end result can be magnified opportunities for both parties.
  • Try Before You Buy.  The EIR role gives you an exceptional ability to spend time with portfolio companies.  They are usually extremely happy to get additional help, and the time spent can help both parties figure out if it’s a potential good fit or not.  The best part about the role is that if it isn’t a good fit, the time spent was without firm commitment, and can be easily ended at any time without few (if any) negative relationship or reputation effects.
  • Self Discovery.  The EIR role is structured to give you time to ask the hard questions about what you are looking for in a company, a product, a market, a culture.  It’s structured enough to provide stimulus and ideas, but unstructured enough to give you gaps to ask (and answer) the hard questions.

Problems with the EIR Position

While I’m extremely positive about my experience as an EIR at Greylock Partners, I’m one of the first to caution people who ask me about the role that there are real issues to consider.

  • Firm Lock In.  When you are immersed in the people & culture of a particular firm, it’s very easy to de-prioritize networking and intellectual debate outside the firm.  Venture firms tend to discuss their own successes and failures, and the burden is really on the EIR to ensure they broaden & deepen their relationships outside the firm.  This is why, for example, some successful executives will take EIR roles at two different firms.
  • Paradox of Choice.  We are all human, and humans don’t do well with a massively expanded selection set.  The more companies, industries, products & concepts you are exposed to, the harder it can be to assertively make a choice to pursue a single company.  This is why, for example, successful EIRs will often frame their time in waves – spending weeks or months on a particular area or topic, and then shifting to another, rather than trying to explore and pursue everything at once.
  • Portfolio Work vs. Discovery.  Working with portfolio companies takes a certain amount of time and effort to be effective.  If you are going to spend 1-2 days a week with a company, you’ll quickly run out of days of the week.  As a result, it’s important for EIRs to find a system that allows them to balance networking & discovery time with active engagement with companies.  6-12 months can pass unbelievably quickly, and in the end, your goal is to find that next great role.
  • Operating Skills / Credibility.  Technology moves incredibly quickly, and it’s amazing how even in a matter of months the landscape of ideas and tactics can change.  Venture capital firms tend to be comfortable places, but never forget that you always need to be learning & growing, most likely by engaging and helping entrepreneurs with real challenges they have today.  The lessons from 2012 are interesting and useful in 2013, but the half life of those lessons can be shorter than you might think.

So, Should You Do It?

I’m colored by own personal experience, which was with a great firm and a great outcome (I’m exceptionally happy with my role at Wealthfront).

If you are looking for either your first CEO role, or your next CEO role, and you have the opportunity to be an EIR with a great firm, I believe the Executive in Residence role can be a unique & excellent opportunity.  Going into it, however, you need to do two things to be successful: be prepared to take advantage of the unique opportunities of the role, and be extremely cognizant of the potential pitfalls and issues inherent with the position.

Going forward in this series, I’ll be focusing on the Executive in Residence role. My next post will attempt to answer the question: “How Do You Get an Executive in Residence Role (EIR)?

EIR Series: What is an Executive in Residence (EIR)?

This is the first post of a multi-part series on being an Executive in Residence (EIR). The initial post outlining the full series can be found here.

One of the first things I learned when I accepted the role of Executive in Residence at Greylock Partners was that almost no one actually knows what that means. (I can hear my father asking me now, “You’re a resident now? Like a doctor?”)

In fairness, the role is rare enough that, outside of the Silicon Valley venture community, you might never run into it. It’s almost pathologically designed to be cryptic. Not only is it rare, but it’s also designed as a short term role, not a permanent one. If that wasn’t tricky enough, it turns out that there are a few flavors of “EIR” just to add a good dose of acronym confusion to the mix.

So before discussing the details of the Executive in Residence role, let me clarify the three different types of EIR you may come in contact with. (As a side note, the following definitions and examples are certainly biased towards my recent experience at Greylock Partners.)

  • Entrepreneur in Residence. The original EIR role, the Entrepreneur in Residence role is designed for entrepreneurs who are actively working on both the conception & execution of their next company. These roles are generally structured as 3-6 month engagements without compensation, but the entrepreneur is given resources & a place to work, and significant time & exposure to the investment team at the venture capital firm. The entrepreneur benefits from the constant challenge & framing of world-class investors, and a higher than average likelihood of funding from the venture capital firm. The firm, on the other hand, gets a significant degree of proprietary access and influence over the new company.

    Notable recent examples: Nir Zuk, co-founder of Palo Alto Networks (PANW, $3B+), Josh McFarland, founder of TellApart.

  • Executive in Residence. Sometimes referred to as an XIR, the Executive in Residence role is designed for executives, typically CEOs, who are in between companies. These roles are typically structured as 6-12 month engagements with limited compensation (well below typical executive salaries). The executive is given an office, with an expectation that they will split their time between working with portfolio companies, helping with due diligence on potential investments, and completing their own search efforts for their next role. The executive gets a platform for broadening their strategic thinking, networking and inside access to a number of extremely promising companies, while the firm gets inexpensive support for their portfolio companies and disproportionate access to top executive talent.

    Notable recent example: Jeff Weiner, CEO of LinkedIn (LNKD, $20B+)

  • “Something Else” in Residence. Behold, the age of the SEIR. In recent years, there have been a few top venture capital firms experimenting with other “in residence” roles. There have been designers, engineers, data scientists and even growth strategists in residence. The basic proposition for this role is similar to the traditional executive in residence role, with a notable tilt towards work with portfolio companies and PR to help build the reputation of the individual and the firm.

    Notable recent examples: DJ Patil, Data Scientist in Residence, Andy Johns, Growth Strategist in Residence.

There have been quite a few good blog posts on the pros & cons of the Entrepreneur in Residence role. On the other end of the spectrum, it’s probably too early to talk categorically about the plethora of new “in residence” variants as a class.

Going forward in this series, I’ll be focusing on the Executive in Residence role. My next post will attempt to answer the question: “Should I be an Executive in Residence (EIR)?

The Executive in Residence (EIR) Series

It’s hard to believe, but it is now exactly six months since I left my role as an Executive in Residence at Greylock Partners, and joined Weathfront as COO.

Diving into a startup is all encompassing, but over the past few months quite a few people have asked me questions about the Executive in Residence (EIR) role.  Some of these people have had offers to become EIRs, others are curious about the role and whether they should pursue it as a career option.  For most, however, it’s just genuine curiosity  the EIR role is largely a low volume, undocumented role that is very unique to the private equity & venture capital ecosystems.

One of the guide posts for this blog has been a dedicated effort to take the questions that I receive regularly, and translate them into thoughtful and useful content to be broadly shared.  So before my experiences of 2012 fade into the shrouds of history, I’ve decided to write a quick series about my experience as an EIR, and the most common questions I’ve received.

The series will cover the following questions:

  1. What is an Executive in Residence (EIR)?
  2. Should I be an Executive in Residence (EIR)?
  3. How do you get an Executive in Residence (EIR) role?
  4. Challenges of being an Executive in Residence (EIR)
  5. Did you like being an Executive in Residence (EIR)?

As always, I’m hopeful that the information will be both interesting and even useful.

Joining Wealthfront

It’s official. As per the announcement on the Wealthfront Blog today, I have officially accepted the role of Chief Operating Officer at Wealthfront. I feel incredibly fortunate to be joining such an amazing team, with an opportunity to help build an extremely important company.

WF Logo New

From Human Capital to Financial Capital

One way to imagine your professional life is overlay of two types of capital: the building and growing of your human capital, and the transformation of that human capital into financial capital.

It feels like just yesterday that I was writing a blog post here about my first day at LinkedIn. At its heart, LinkedIn is building, growing & leveraging human capital throughout your career.  Wealthfront provides an answer to the second part of that equation – how to grow and leverage the financial capital that you accumulate throughout your career.

As Marc Andreessen put it, software is eating the world, and it is providing us a platform to bring the features and sophistication previously only available to the ultra-rich, and making it available to anyone who wants to protect & grow their savings.

Too many good, hard-working individuals today lack access to many of the basic advantages accorded to people with extremely high net worth.  With software, Wealthfront can bring features and capabilities normally available only to those with multi-million dollar accounts to everyone, and at a fraction of the cost.

Personal Finance as a Passion

For regular readers of this blog, the fact that personal finance has been a long standing passion of mine comes as no surprise.  What many don’t know is that this passion dates all the way to back to my time at Stanford, where despite one of the best formal educations in the world, there was really no fundamental instruction on personal finance.

In fact, upon graduation, I joined with about a dozen friends from Stanford (mostly from engineering backgrounds) to form an investment club to help learn about equity markets and investing together.  (In retrospect, the members of that club have been incredibly successful, including technology leaders like Mike Schroepfer, Amy Chang, Mike Hanson and Scott Kleper among others.)

A Theme of Empowerment

As I look across the products and services that I’ve dedicated my professional life to building, I’m starting to realize how important empowerment is to me.  At eBay, I drew continued inspiration from the fact that millions of people worldwide were earning income or even a living selling on eBay.  At LinkedIn, it was the idea of empowering millions of professionals with the ability to build their professional reputations & relationships.

With Wealthfront, I find myself genuinely excited about the prospect of helping millions of people protect and grow the product of their life’s work.

We’ve learned a lot in the past thirty years about what drives both good and bad behaviors around investing, and we’ve also learned a lot about how to design software that engages and even delights its customers.  The time is right to build a service that marries the two and helps people with one of the most important (and challenging) areas of their adult lives.

A Special Thank You

I want to take a moment here to voice my utmost thanks to the team at Greylock Partners.  My year at the firm has given me the opportunity to learn deeply from some of the best entrepreneurs, technology leaders and venture capitalists in the world.  The quality of the entrepreneurs and investors at Greylock forces you to think bigger about what is possible.  Fortunately, Greylock is also a partnership of operators, so they understand the never-ending itch to go build great products and great companies.

… And Lastly, A Couple of Requests

Since this is a personal blog, I don’t mind making a couple of simple requests.  First, if you have a long term investment account, whether taxable or for retirement, I would encourage you to take a look at Wealthfront.  I’d appreciate hearing what you think about the service and how we can make it better.

Second, and perhaps most importantly, we are hiring.  So let me know if you are interested in joining the team.

User Acquisition: Mobile Applications and the Mobile Web

This is the third post in a three post series on user acquisition.

In the first two posts in this series, we covered the basics of the five sources of traffic to a web-based product and the fundamentals of viral factors.  This final post covers applying these insights to the current edge of product innovation: mobile applications and the mobile web.

Bar Fight: Native Apps vs. Mobile Web

For the last few years, the debate between building native applications vs. mobile web sites has raged.  (In Silicon Valley, bar fights break out over things like this.) Developers love the web as a platform.  As a community, we have spent the last fifteen years on standards, technologies, environments and processes to produce great web-based software.  A vast majority of developers don’t want to go back to the days of desktop application development.

Makes you wonder why we have more than a million native applications out there across platforms.

Native Apps Work

If you are religious about the web as a platform, the most upsetting thing about native applications is that they work.  The fact is, in almost every case, the product manager who pushes to launch a native application is rewarded with metrics that go up and to the right.  As long as that fact is true, we’re going to continue to see a growing number of native applications.

But why do they work?

There are actually quite a few aspects to the native application ecoystem that make it explosively more effective than the desktop application ecosystem of the 1990s.  Covering them all would be a blog post in itself.  But in the context of user acquisition, I’ll posit a dominant, simple insight:

Native applications generate organic traffic, at scale.

Yes, I know this sounds like a contradiction.  In my first blog post on the five sources of traffic, I wrote:

The problem with organic traffic is that no one really knows how to generate more of it.  Put a product manager in charge of “moving organic traffic up” and you’ll see the fear in their eyes.

That was true… until recently.  On the web, no one knows how to grow organic traffic in an effective, measurable way.  However, launch a native application, and suddenly you start seeing a large number of organic visits.  Organic traffic is often the most engaged traffic.  Organic traffic has strong intent.  On the web, they typed in your domain for a reason.  They want you to give them something to do.  They are open to suggestions.  They care about your service enough to engage voluntarily.  It’s not completely apples-to-apples, but from a metrics standpoint, the usage you get when someone taps your application icon behaves like organic traffic.

Giving a great product designer organic traffic on tap is like giving a hamster a little pedal that delivers pure bliss.  And the metrics don’t lie.

Revenge of the Web: Viral Distribution

OK. So despite fifteen years of innovation, we as a greater web community failed to deliver a mechanism that reliably generates the most engaged and valuable source of traffic to an application.  No need to despair and pack up quite yet, because the web community has delivered on something equally (if not more) valuable.

Viral distribution favors the web.

Web pages can be optimized across all screens – desktop, tablet, phone.  When there are viral loops that include the television, you can bet the web will work there too.

We describe content using URLs, and universally, when you open a URL they go to the web.  We know how to carry metadata in links, allowing experiences to be optimized based on the content, the mechanism that it was shared, who shared it, and who received it.  We can multivariate test it in ways that border on the supernatural.

To be honest, after years of conversations with different mobile platform providers, I’m still somewhat shocked that in 2012 the user experience for designing a seamless way for URLs to appropriately resolve to either the web or a native application are as poor as they are.  (Ironically, Apple solved this issue in 2007 for Youtube and Google Maps, and yet for some reason has failed to open up that registry of domains to the developer community.)  Facebook is taking the best crack at solving this problem today, but it’s limited to their channel.

The simple truth is that the people out there that you need to grow do not have your application.  They have the web.  That’s how you’re going to reach them at scale.

Focus on Experience, Not Technology

In the last blog post on viral factors, I pointed out that growth is based on features that let a user of your product reach out and connect with a non-user.

In the mobile world of 2012, that may largely look like highly engaged organic users (app) pushing content out that leads to a mobile web experience (links).

As a product designer, you need to think carefully about the end-to-end experience across your native application and the mobile web.  Most likely, a potential user’s first experience with your product or service will be a transactional web page, delivered through a viral channel.  They may open that URL on a desktop computer, a tablet, or a phone.  That will be your opportunity not only to convert them over to an engaged user, in many cases by encouraging them to download your native application.

You need to design a delightful and optimized experience across that entire flow if you want to see maximized self-distribution of your product and service.

Think carefully about how Instagram exploded in such a short time period, and you can see the power of even just one optimized experience that cuts across a native application and a web-based vector.

Now go build a billion dollar company.

Joining Greylock

Today, John Lilly put up a really nice note on the Greylock Partners blog officially welcoming me to the firm.  Needless to say, I’m both honored and excited to be joining such a great team.

We’re fortunate to be witnessing the explosive growth of not one but two incredible new platforms for consumer products and services: social and mobile.  Both are literally changing the fundamental ways that consumers interact with devices, and are rapidly changing the dynamics for building successful new products and services.  After spending the past four years helping to build out social and mobile platforms, I can’t wait to partner with entrepreneurs to help them build out the next generation of products and companies over them.

Over the past few years, I’ve shared a number of insights here on this blog about building great products and companies.  Here are a few that are worth reading if you are curious about how I think:

And of course, the most appropriate for this announcement:

For now, I just want to say thank you to Reid, David, John and the entire Greylock team.  I can’t wait to get started.

Observations: The Paradox of Being a “Smart” Venture Capitalist

My last post, and observation of business & government students, was popular enough that I think I’ll share a second one here.   This is an observation that I’ve shared with a large number of people in the past seven years, as part of my greater set of take-aways on working in venture capital.

I worked for Atlas Venture from 2001-2002 as an Associate, and during that time I had the chance to observe quite a the interesting paradoxes that make up success in early-stage venture capital.  This particular observation is about the paradox surrounding being seen as “smart”.

In the short term, venture capitalists often look smart by saying “No”.  But in the long term, venture capitalists can only look smart by saying “Yes”.

This applies generally to new people joining the industry, regardless of level.  New associate, venture partner, general partner.  Venture capitalists deal with exceptionally long cycles.  It takes the better part of a decade to build most businesses, and it can take that long to really determine who in venture capital is doing the job, and who is just playing the part.

In the long term, the metric is simple: how many successful entrepreneurs & companies did the venture capitalist fund & help build to extraordinary outcomes.

In the short term, people are desperate for any tangible signal that will predict the long term.   Unfortunately, in many cases, the short hand for this becomes evaluating their critical thinking about risks and issues on every pitch.

As a product leader, I see this behavior play out on a regular basis outside of venture capital as well.  More experienced product managers will review the work of junior product managers, and will prove their capabilities by highlighting problems.

They don’t realize that they will never be great by pointing out flaws.  They will be great by translating that knowledge into solutions for other people’s products, as well as leading their own innovative initiatives.

I could always tell when a general partner, whether at Atlas or another firm, was “ready to fund”.  You would see their posture in meeting shift radically from finding ways to say no to finding ways to say yes.

Not surprisingly, my fondest memories of venture capital surround the start-ups where I said yes.

Startups, Technology Companies & Giambattista Vico

I had one of those “delightful” newspaper moments today.  I was going through my Sunday morning ritual, page-by-page through the Sunday New York Times, when I happened upon an interesting editorial in the Week in Review.

The article itself was interesting, but likely one I would have ignored in the online version.  (It’s still one of the virtues of print that I put myself in the hands of the editor, and read the Week in Review from beginning to end.)  What was delightful about it was its philosophical reference to Giambattista Vico.

You see, until today, I had no idea who Giambattista Vico was.  However, it turns out that this 18th century Italian philosopher published a theory of societies that happens to match, almost exactly, my recent theory about start-up technology companies and their development into large, successful enterprises.   Here is a summary from the Stanford Philosophy website:

Nations need not develop at the same pace-less developed ones can and do coexist with those in a more advanced phase-but they all pass through the same distinct stages (cursi): the ages of gods, heroes, and men. Nations “develop in conformity to this division,” Vico says, “by a constant and uninterrupted order of causes and effects present in every nation” (“The Course the Nations Run,” §915, p.335). Each stage, and thus the history of any nation, is characterized by the manifestation of natural law peculiar to it, and the distinct languages (signs, metaphors, and words), governments (divine, aristocratic commonwealths, and popular commonwealths and monarchies), as well as systems of jurisprudence (mystic theology, heroic jurisprudence, and the natural equity of free commonwealths) that define them.

In other words, Vico outlines three distinct phases for societies:

  • An age of gods, when man and immortal walk amongst each other
  • An age of heroes, when the gods have departed, but their children or disciples perform wonders with their power
  • An age of men, when their is equality and democracy among men, and a lack of the supernatural

(Yes, I’m grotesquely paraphrasing.  Bear with me on this one for a moment).

When I left eBay in 2007 to join LinkedIn, many people asked me why I was interested in joining a startup at that time.  Being an avid fan of Greek Mythology, I told friends that there were three phases to the tech company lifecycle in Silicon Valley:

  • The golden age, when gods (aka founders and first employees) walk the floors.  This is a time of incredible vision, passion, and risk.   The events and people of this era become myth and legend rapidly.  The company typically at this time has a product/concept, but no proven business model or engagement with customers.  The company is usually measured in tens of employees.
  • The bronze age, when the gods give way to the heroes, the first wave of executives who help grow and scale the company and fulfill its destiny.  Usually this is a time when the business model has proven out, and the larger risk to the company is its ability to manage growth and scale the organization in both talent and execution.  This is still a time of passionate debate and eccentricity, but now at a larger scale as the organization and business broadens.  This is when the company goes from tens of employees to thousands.
  • The iron age, when the gods and heroes have fled, and the company is managed as a large, public technology company.  At this point, the company is typically measured in tens of thousands.

Amazing similarity… no doubt both Vico & I were both fans of the classics.

When I joined eBay in 2003, it turns out that I joined the company well into its bronze age.  Many of the early employees (and a founder) had left, but most of the original heroes who worked under them and with them remained.   There was no separate corporate entity, and the PayPal acquisition had just happened.  In 2003, a product manager would still present a product strategy directly to Meg at times.  But by the time 2007 rolled around, as many of the heroes  departed, it was clear that eBay had entered its iron age.

Obviously, there are later phases for technology companies that can be interesting.  (Believe me, as someone who joined Apple in the mid-1990s.)  And there are always outliers (Google has stayed in its bronze age longer than most.)  But these phases do a fair job of describing the cultural dynamics of those first few phases of a technology company.

For companies, there are no clear delineations between the ages.  The transitions tend to be gradual, and as often as not tend to reflect the four-year pattern for stock option vesting schedules.  In the last few years, however, I’ve found this framework fairly effective in describing how company cultures evolve, and how that influences the enjoyment and job satisfaction of employees who prefer one phase over another.

Maybe the reason this analogy has been useful for me personally is because, as Vico supposed, it reflects a more general description of how groups of people evolve socially when they dedicate themselves to a single social contract.  For Vico, that was a nation.  For Silicon Valley, it’s a start-up.  It’s interesting to consider that the venture capital financing model and stock option vesting model tends to encourage this type of phasing almost naturally over the growth of a new technology venture.

Something to think about, of course.

J-Curve & The Hype Cycle: Potential Exits

Will Hsu had a very interesting post on his blog, Hitchiker’s Guide to 650.  (Yes, it’s a pretty cool blog title)

Will overlayed the now infamous Hype Cycle and a hypothetical startup valuation J-Curveover each other, like this:

2989415251_27295b1663

(Minor nits – the J-Curve here likely shouldn’t start at zero, but at some higher amount.  The founding team and the concept itself has some value, and typically, while the startup is nascent, the value hinges on that alone.  In fact, it probably rises initially as risk is taken off the table with a few key hires/revisions.  It doesn’t change the insight from the overlay, however.)

He then postulated a few different exit points, with reasonable valuations and time frames, and then highlighted the different ROI values for each.

  • Exit #1: 2~4x, 50~150% IRR (assuming 1.5~2yr hold, 1~2 rounds)
  • Exit #2: 2~4x, 30~70% IRR (assuming 3~5yr hold, 2~3 rounds)
  • Exit #3: 10~100x, 30~70% IRR

(You can read the full details here)

I must have seen versions of the  J-Curve and The Hype Cycle curves a hundred times, but for some reason, seeing them overlayed in the context provides some unique insight into the highs (and lows) of a venture backed startup.  It also highlights the incredible cost to being caught flat-footed (ie, needing cash) at the wrong points in the curve.

I also like the clear, numerical validation of a simple truth of venture investing (and entrepreneurship):  you achieve the highest internal rate of return by cashing out quickly.  But to achieve truly game-changing cash returns for investors (ie, return the fund), the big win is required.

The numbers really aren’t as material as the visualization of the two curves together.

LinkedIn and the Three Bears

Alright, alright.  I know I’m not supposed to be posting about LinkedIn on my personal blog.  But sometimes, the news is really big, and worth sharing with friends & family who read this blog.

So, before you read it in tomorrow’s newspapers, you might want to catch the blog post by Dan Nye, our CEO, on the LinkedIn official blog.  Dan did a great job with the intro:

One of our fundamental beliefs at LinkedIn is that the company you keep is one of the most credible reflections of who you are and what you have to offer.

Like individuals, successful companies are also built on strong networks of relationships, and LinkedIn continually strives to create the right partnerships to help us build a great service for our members, and advance our business.

Today I am happy to announce that LinkedIn has raised additional funding from our original investors and added another world-class investor to our team. Bain Capital Ventures joins our existing group of investors – Sequoia Capital, Greylock Partners, and Bessemer Ventures – and leads this round of investment at a total of $53 million.* (LinkedIn has previously raised $27 million).

The (*) is the footnote that the investment implicitly values the company at over $1 Billion in total.

As a result, there is a lot of press already published, and a lot more to come I expect.  Reading through comments already in the blogosphere, I’m definitely seeing a “Goldilocks” theme to the comments:

  • This bear thinks the price is too high
  • This bear thinks the price is too low
  • This bear thinks the price is *just* right

But I think Dan’s post reflects the true issue with an investment like this – we have a great new partner joining the LinkedIn team who believes in the vision and the value we are creating with the company and its products and services.  More importantly, it’s a reminder that investors are placing millions of dollars in trust with the LinkedIn team to fulfill this vision, and create a business of extraordinary value.  Our users also invest in us every single day with their time, their effort, their passion, and their careers.

So, I’m going to bow out of any debate on valuation, and focus on the real challenges ahead.  I’m hoping that our actions and efforts in the coming months and years will speak louder than words (or numbers, in this case).

Let me leave you with some thoughts on LinkedIn from our investors:

Here Comes Another Bubble: YouTube Video (The Richter Scales)

Hits a little too close to home… especially on the housing prices in the Bay Area. :)

So clever I watched it twice. Plus, I feel like being a fan boy because when they say “hire an engineer”, I’m pretty sure I know that engineer! :)

The Best Blog Posts on Venture Capital

Sorry, but I couldn’t help providing these pointers.

I’ve been thinking for a while about writing some posts explaining venture capital. While I have a lot of friends who are serial entrepreneurs and venture capitalists, one of the my realizations in the brief time I spent in the industry was how poorly understood it is by 99% of people.

Well, it looks like Marc Andreesen beat me to it.  His posts contain roughly 90% of what I was going to say.

He has three of them:

Marc describes his experience with venture capital as follows:

My experience with venture capital includes: being the cofounder of two VC-backed startups that later went public (Kleiner Perkins-backed Netscape and Benchmark-backed Opsware); cofounder of a third startup that hasn’t raised professional venture capital (Ning); participant as angel investor or board member or friend to dozens of entrepreneurs who have raised venture capital; and an investor (limited partner) in a significant number of venture funds, ranging from some of the best performing funds ever (1995 vintage) to some of the worst performing funds ever (1999). And all of this over a time period ranging from the recovery of the early 90′s bust to the late 90′s boom to the early 00′s bust to the late 00′s whatever you want to call it.

Normally, I’d be skeptical, but as I read his posts further, I found myself really appreciating the perceptiveness of his comments.

For example, here is a brief passage from the first post:

Within that structure, they generally operate according to the baseball model (quoting some guy):

“Out of ten swings at the bat, you get maybe seven strikeouts, two base hits, and if you are lucky, one home run. The base hits and the home runs pay for all the strikeouts.”

They don’t get seven strikeouts because they’re stupid; they get seven strikeouts because most startups fail, most startups have always failed, and most startups will always fail.

So logically their investment selection strategy has to be, and is, to require a credible potential of a 10x gain within 4 to 6 years on any individual investment — so that the winners will pay for the losers and in the timeframe that their investors expect.

All early stage venture capitalists will repeat the above analogy to you, but personally I found that in 2001-2002, very few venture capitalists internalized what that analogy really means. What it means is that you need to take a certain number of “swings” every year, just to make sure your odds of connecting with a winner pan out. In 2001-2002, too many venture capitalists sat on the sidelines, debating whether $4M should buy them 50% or 60% of a Series A company, instead of making sure that they kept investing. After all, any contrarian investor will tell you, you force yourself to put money in when times look grim.

I also really appreciated this quote from Marc’s second article:

Why we should be thankful that we live in a world in which VCs exist, even if they yell at us during board meetings, assuming they’ll fund our companies at all:

Imagine living in a world in which professional venture capital didn’t exist.

There’s no question that fewer new high-potential companies would be funded, fewer new technologies would be brought to market, and fewer medical cures would be invented.

We should not only be thankful that we live in a world in which VCs exist, we should hope that VCs succeed and flourish for decades and centuries to come, because the companies they fund can do so much good in the world — and as we have seen, a lot of the financial gains that result flow into the coffers of nonprofit institutions that themselves do huge good in the world.

Remember, professional venture capital has only existed in its modern form for about the last 40 years. In that time the world has seen its most amazing flowering of technological and medical progress, ever. That is not a coincidence.

This is what made me passionate about venture capital when I was in the industry, and it’s why I will likely return to it in some form again. There is an extremely important role to play for venture capitalists to play in getting money from large, conservative institutions effectively into the hands of risky entrepreneurs who are building the new technologies and businesses of tomorrow. You won’t get there with government funding or small business loans.

My favorite part of Marc’s series, however, is in his third article, when he discusses the current paradox of venture capital, one that has surprised me personally. The question is this:

If venture capital in the past 7-8 years has had such horrible risk-adjusted returns compared to the public markets, why hasn’t the amount invested in venture capital funds decreased dramatically?

The answer is asset allocation.

I remember my Private Equity class at Harvard, where Dave Swensen, of Yale Endowment fame, came to speak. Venture capital has become an asset class that every multi-billion-dollar institution feels like it needs in its portfolio. This is because after 25 years of modern venture capital, it because a proven fact in the 1990s that over the long term, venture capital has returned almost 2x the public market return, with low correlation to the public stock market. That may not sound like much to you, but that’s music to a money-manager’s ears.

This predictably led a significant number of institutions to shift massively into alternative investments and venture capital in the late 90′s, just in time to get hammered by the crash of 2000-2002.

Here’s the interesting part: that hammering — by people who, say, only started investing in venture funds in 1999 — has not resulted in a significant pullback on the part of institutional investors from venture capital.

Instead, venture capital has become an apparently permanent asset class of many large institutional investors — and increasingly, smaller institutional investors.

One element that I do believe Marc missed here is the behavioral finance aspect of why institutions still put billions into venture capital. You see, on average, venture capital has done poorly the last 7-8 years. But there have been some great funds that have performed spectacularly (Google, anyone?) Like hedge funds, many institutions have money managers that believe that the venture capital funds that they have picked will be the few that outperform. (Of course, most of the best venture funds turn away money regularly, but that’s another story.)  Thus, everyone believes that they will be “above average”, even though that’s not possible.

In any case, definitely read Marc’s articles. Bookmark them. Read them and think about them the next time you read some press about venture capital. They are keepers.  I just wish I had written them first.

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