Archives For startups

I’ve spent many of my commuting hours over the last year listening to podcasts from Stanford University’s DFJ Entrepreneurial Thought Leaders lecture series.  These lectures have taken place every Wednesday for the last ~9 years, so there are hundreds at this point.

I started with the lectures in ’05 and have been working backwards.  Below are some of my favorite presenters from ’05 and ’06.  I’ve included select quotes, but each of these has dozens of quotes that are equally insightful.  Despite being nearly a decade old, the advice and themes presented in these lectures are timeless.

Stay tuned – I’ll release the rest of the 2006 speakers in my next installment.

Mark Zuckerberg in ’05 (Facebook) – From Harvard to the Facebook

Starting at 49:40

“As organizations grow, a lot of the issues and structure that’s put in place is put there because a comfort level breaks down in people communicating freely, in a way that they can when they’re friends… If you’re working with your friend, you can tell him or her whatever you’re thinking and it’s not going to offend him or her and they’ll probably comprehend it similarly to how you imagined it… A lot of the stuff, like saying take 20% of your time to go put it into action an idea that you might have is necessary in a large organization where people can’t necessarily speak the same language or where ideas can’t get out freely…

One of the things that I do focus on at Facebook is making sure that the culture is very friendly in that people hang out. Instead of having 20% of people’s time spent working on their own projects, I make people hang out with each other…  I can’t force people to hang out outside of work, but I can make it so that people are more comfortable with each other and can communicate more freely… By doing this, we create a culture where people just talk to each other about stuff and get what each other is thinking more clearly than they would if the organization was more bureaucratic or if people wouldn’t be heard.  Since people are always talking, ideas get bounced off each other and then eventually someone starts making something and then, we’re done.”

Joe Liemandt in ’05 (Trilogy) – The Passion and Perseverance Behind a Start-up

At 23:20 “When you’re doing your startup, it is so much better to be lucky than right.”

At 27:00 “Fortune 500s don’t want to buy from startups, but if you’re the only one that have it and they want it, the corollary is that they are price insensitive because they are only buying it from you because they have no other choice.”

Tom Byers in ’06 (Stanford) – Ten Enduring Success Factors for High Technology Entrepreneurship

9:06 “I’d love to be ready to have another 50 year career because stuff, whether it’s in IT or nano or bio or my favorite one here, the environment and energy.  It’s really the intersections of these (that’s most exciting).”

15:00 “Great leaders have a this wonderful ability of keeping this in mind: vision drives strategy, which drives execution.  CEOs and founders have to evolve as people.  It’s really interesting to watch and track that.”

Janice Fraser in ’06 (Adaptive Path) – Entrepreneurial Leadership Qualities

5:52 “You have to chose your partners based on who you want to go through the rough times with.  Every single entrepreneurial venture, whether it’s very successful or a dismal failure, will go through rough times.  You’re going to have to make really difficult decisions.  Every day, you’re going to have to wake up and decide what to spend money on or more importantly, what not to spend money on.  You’re going to have to decide which of the ten ideas you have is the one you’re going to do.  And you’re going to argue about that, at least if it’s good.  If there’s potential, you’re you’re going to have really hardcore meaningful arguments every day.  So the most important foundation piece for any business that you want to start is having a solid partnership.”

16:50 “You need to create meaning not just in the world, you also have to create meaning for the people who are making this entrepreneurial venture go.  It takes tremendous effort to get a new venture off the ground.  You have to be 100% passionate about it.  You have to keep your feet on the ground and be rational, but at the same time you have to live this dual life where you are just zealously pursuing this opportunity.”

Marissa Mayer in ’06 (Google) – Nine Lessons Learned about Creativity at Google

11:40 “It turns out when we were small we launched really rough things that weren’t very good all the time. But the key is iteration. When you launch something, can you learn enough about the mistakes that you made and learn enough from your users that you ultimately iterate really quickly? We make mistakes every time, every day, thousands of things wrong with Google and this product that we know we could fix, but if you launch things and iterate really quickly, people forget about those mistakes and they have a lot of respect for how quickly you build the product up and make it better.”

Kathy Eisenhardt in ’06 (Stanford) – Research Lens on Understanding Entrepreneurial Firms

Starting at 36:40

“If there are a lot of opportunities around a space that’s a really good place to be.  On the other hand, there are some really bad places to be and that’s in complicated markets.  That’s a market where you have to get a lot of things right to be successful.  Biotech is a classic example of a complicated market where you have to get FDA right and you got to get a whole bunch of things right to be successful.  You want low complexity, high velocity.

If you’re in a highly ambiguous market (unclear business plan, don’t know who customers are), it doesn’t really matter what you’re doing.  You can just do a bunch of stuff and it’s mostly about luck.  In contract, a low ambiguity market is all about skill and about being at the right structure.  If you’re in a really ambiguous new market, you want to structure it.  If you’re a skilled person you want to get rid of that ambiguity by structuring it.  If you’re not so skilled and you want to learn it then don’t want it to structure.

If it’s an unstable, uncertain market, then what you really are trying to do is find the optimal structure. As you go in an uncertain market, what you typically want is less structure and you typically want to manage the amount that you have. What makes uncertain markets so hard for big companies is they’re coming from markets where it didn’t matter how much structure you had and they’re going to a market where it does matter. The risk for young companies is they don’t get structured enough. In my experience most of the best entrepreneurial companies have more structure than their peers.”

Over the past few years, I have helped many of my friends understand options in their employment contracts.  Most candidates have a general misunderstanding and discomfort when it comes to options, so I’ll give a brief overview to try and shed some light on the issue.

First, options are not equity.  If you receive options, you won’t actually own any of the company yet.  You are being given an opportunity to buy shares at a later date for a fixed (and predetermined) price per share.  You will make money by buying at the predetermined price and selling during an exit event at a new, higher price.  Without an exit event (sale, merger, or IPO), you won’t be able to sell your illiquid shares and your purchase will represent an investment in the company’s future.

Options vest (become exercisable) over time based on your vesting schedule.  If you leave the company at any point, you will typically have ~90 days to exercise your vested options or you will forfeit them. If you are leaving the company because it isn’t doing well, it’s unlikely that you will want to invest cash in exchange for shares.

On the flip side, if a company gets bought for a valuation that is 10x larger than it was on your grant date, you can immediately convert your vested options into shares and sell them for a 900% profit (assuming no dilution, which is highly unrealistic).

Almost every company will insist on a 1-year cliff so that none of your options vest until you’ve been with the company for a full year.  But what happens if the company gets bought after 10 months of your being employed there?  If you don’t have an acceleration clause (and most contracts do not come with one), you get nothing.

Things you should look for in your contract

  1. A grant date – Important for many reasons including determining when your vesting schedule / 1-year cliff begin and for tax purposes.
  2. A strike price – At what price you can buy shares of the company.  Options are exercised and converted to shares by paying the company the strike price per share.
  3. Total # of options granted – With this you can determine what your cash outflow will be if all your options vest and you buy shares at the strike price.  Keep in mind that the company will probably issue additional shares to you each year or with each promotion.
  4. Total # of shares currently outstanding or % of the company your options represent – How much of the company will you own (prior to dilution) once all of your shares vest?  If they give you the total shares outstanding, you can just divide your # of shares by the # of shares outstanding.
  5. Dilution – This is where the company issues additional shares, which they will do for multiple reasons.  You should assume that your % ownership will be 1/2 of what it is now by in an exit event.  They probably won’t give you dilution protection, but it doesn’t hurt to ask!
  6. Vesting schedule – Typically 4 years.  Vesting is the rate at which your options become exercisable.  Before any of your options vest, you can’t convert them into ownership and there is typically a 1-year cliff on vesting.
  7. A 1-year cliff – Will likely be in every contract and prevents the employee from having any options vest in their first year.  If you have a 4-year vesting schedule, 25% of your options will vest on your 1-year anniversary.  Be wary of any cliffs that have a longer duration, especially if you don’t have an acceleration clause.
  8. An acceleration clause – Single trigger if the company is acquired and double trigger if acquired and you get fired.  At a minimum, 25% of your options should vest in a single trigger and another ~25% in a double trigger situation.  Many contracts won’t include anything about acceleration, so make sure to bring this up.  This is particularly important if the company is doing well and has already raised significant ($2m+) capital, as they are more likely to be an acquisition target in the near-term.

Have you come across anything that I’m missing?  Please let me know in the comments or shoot me an email.  I’m happy to dive deeper into any of these topics or speak with you 1-on-1 if that would be helpful.

Many new entrepreneurs, especially those located in Silicon Valley / Bay Area, are drawn to the allure of consumer focused startups.  It’s easier for entrepreneurs (particularly ones with little business experience) to imagine using consumer products and they are typically simpler to design.  In addition, consumer focused Minimum Viable Products (Eric Ries’ The Lean Startup) can be enough to draw widespread attention from target customers and news feeds like TechCrunch or PandoDaily.

Enterprise focused startups are a tremendous opportunity because 1. there are fewer competitors and 2. most enterprise customers are already paying for a legacy product that is likely not web-based (SaaS).  According to Jim Goetz of Sequoia Capital, “Enterprise remains an ‘enormous opportunity’ because companies are spending  about $500 billion a year with legacy enterprise companies and those budgets are  ripe for the plucking.”

Consumer based startups may go from zero users to 100 million users virtually overnight only to fizzle out when interest wanes.  Most never figure out how to make money and have a tough time raising funds.  Enterprise startups, on the other hand, take longer to get going but have a clearer growth trajectory with real revenue.  Most venture capital firms prefer to back enterprise startups because there is a more manageable growth trajectory and usually a more lucrative exit.

Yammer, Workday, Box, Cloudera, Lithium Technologies and Nicira are a few examples of recent enterprise successes.

This blogpost from Shopify gets me super fired up.  It’s an aggregation of TED Talks that have direct relevance for entrepreneurs and startups.  TED, for those that don’t know, is an annual conference that brings together the world’s most interesting minds and challenges them to give the talk of their lives in under 18 minutes.

Over 900 of these talks and performance are available for free to the general public on and many are relevant for entrepreneurs.  Mark Hayes at Shopify pulled together 12 of the ones he felt were most directly relevant for internet startups.

One of my favorites is a speech given by Simon Sinek about why people make purchasing decisions and how to lead effectively.

Memorable quotes include:

“People don’t buy what you do, they buy why you do it.”

“If you talk about what you believe, you will attract those who believe what you believe.”

“What you do proves what you believe and people will do the things that prove what they believe.”

Simon Sinek: How great leaders inspire action

If you learn to program you’ll have a superior sense of the true cost of software development and will be a much more successful non-technical cofounder.  The most precious resource is time and many non-technical cofounders get tripped up by a false sense of how long things should take to implement.  Learning to code has never been easier and you can check out my earlier post on how to get started.

Business cofounders shouldn’t get lured into thinking that they don’t need technical skills when looking at the CEOs of multi-billion dollar tech companies.  Guys like Zuckerberg, Bezos, Steve Jobs and Bill Gates all started out with a solid foundation of technical knowledge, which contributed to development efficiency.

This article from Rob Spectre over at Fast Company points out that Donald Trump’s success is the result of his knowing the costs associated with real estate development better than any of his competitors.  In the end, running a successful startup is about out competing your competition in the pursuit of limited resources: funding, advice, talented engineers, time, etc.  Having a basic understanding of coding makes entrepreneurs better competitors.

Value of Time

July 18, 2012 — Leave a comment

Jack Groetzinger, the founder of SeatGeek wrote an article today that puts a unique spin on the cost-cutting focus of many startups.  Many founders focused on running a lean startup are focused on minimizing what they view as excess expenditures and, as a result, effectively value their time at $0 / per hour.

For example, if it takes me an hour to get somewhere by bus for $5 and 30 minutes to get somewhere by train for $10, I only save $5 in that half hour by choosing the bus.  If my time is worth more than $10 / hour to me (which it is), I maximize my value to my startup by taking the train.

However, it is tough to put a dollar amount on intangibles associated with this decision.  For instance, I may choose the bus if the bus better exposes me to other entrepreneurs  traveling from Palo Alto to San Francisco that might help my business.

A smart entrepreneur will estimate what their time is worth and the non-dollar impact of their choices and make decisions that maximize their value.

Jack’s full article can be found here.

Learning To Code

July 15, 2012 — 2 Comments

If you’ve never coded before, have no fear.  While it’s possible to start a tech business without any coding / web development background, putting some effort into learning the basics will pay dividends in getting your engineers to respect and follow you.  One of the easiest ways to get started is to take an online course, such as the one offered by Codecademy.  This will teach you web programming basics such as HTML, JavaScript and CSS to help you build interactive websites.  This is an amazing tool to get you on your feet quickly, especially if you have no programming experience.

Back-end Frameworks: Once you’re done with Codecademy, you’ll have the basics of front-end web development.  At this point you may want to learn a bit about back-end frameworks like Ruby on Rails or Django (Python).  The debate between whether to learn Python or Ruby is a heated one and you really can’t go wrong with either.  There’s a great thread on this topic on Quora.  At this point in your coding career, I would stay away from languages like PHP and Java given the time required to get up to speed and develop anything useful.

If you elect to learn Ruby, TryRuby is a great introduction to the Ruby programming language and can be accessed from your web browser (doesn’t require any installation).  This is pretty lightweight and will give you a sense for how the Ruby language functions.  Once you’ve gotten through TryRuby, you’re likely ready to dive deeper by following a Ruby on Rails tutorial.  Getting the Ruby on Rails framework up-and-running on your computer will be one of your hardest tasks and is easier on a Mac.  A great tutorial is Michael Hartl’s Ruby on Rails Tutorial.  Whenever you get stuck, you’ll be able to find solutions to your problems using Google since Ruby has one of the most active communities of any programming language.

For those that elect to go with Django, many tutorials exist.  Python has been popular for longer than Ruby and, as a result, there is a ton of information out there.  Most of the computer science departments at major universities teach Python, so taking an online class like the one currently being offered by Udacity, is a great option.  There are so many online course options available that I’ll post a separate dedicated thread later.


When you want to begin building mobile applications (i.e. for the iPhone), this is easiest with a Mac and can be done using the iOS development tool Xcode.  There’s a great post on this on Udemy, so I won’t go into it here.  To program a native mobile app (as opposed to a web-based mobile website), you’ll have to dabble in Objective-C (Cocoa) or something similar (like RubyMotion).


If you want to be in the startup world, but think of yourself as a business cofounder, you’ll have to know something about programming to command any respect from your engineers.  You’re unlikely to get much traction with the tech community or in finding a technical cofounder if you have no technical knowledge.  The best way to learn to code is to do some of the tutorials suggested above and then create something for yourself.  It’ll be painful, but building yourself a tool will increase your credibility and give you confidence in your ability to understand the technical side of things.

Wanted to share with you an interview of Eric Ries, author of The Lean Startup.  Eric gives advice for all levels and phases of startups, from idea inception and shortening incubation times to managing the inevitable pivots. He talks about creating a minimum viable product (MVP) to figure out whether you have customers for your idea.  Ries says if you have an incredible idea, make a landing page with no product and see if people will sign up for more information.  If they do, you may be on to something.  He also advocates split testing, which is assessing whether customers actually care about update before working on them.  The more continuous your releases are, the more feedback you get.

It’s important to realize that customers aren’t always right, but their feedback can provide useful insights into how other customers might react to your product.  “Asking customers what to do is a total abdication of our responsibilities as founders.  It’s our job to keep the vision of the Company.  Our goal as entrepreneurs is not to ask customers how they think they might behave, but to experiment to discover how they actually behave.  That’s very different from doing focus groups and just asking people what they think.  It’s about trying to construct experiments to say, ‘hey, does this make sense?'”  MVP isn’t about doing the smallest amount possible, it’s about doing the minimum that will be a learning exercise.  Any testing today is much better than the highest quality testing a month from now.  Ries encourages anybody with a great idea to launch as soon as possible to garner feedback.  Telling somebody about an idea isn’t nearly as good as showing them an MVP.

Engines of Growth

There are three different types of startups that have three different categories of important metrics.  The viral engine of growth is followed by companies like Facebook, where the viral coefficient (how many additional people are forced to perform an action because user x performs an action) is a key component of success.  In a viral business, monetization isn’t important early as you can always charge later on.  The second type of business is the sticky / engagement type, which are followed by products like World of Warcraft, where users become addicted and all that matters is how much retention can be achieved.  Engagement businesses would never do anything that would sacrifice addictiveness for monetization.  Paid engine of growth is where you make money from each customer and reinvest it in acquiring new customers.  Growth is easily calculated as the lifetime value of a customer minus the cost to acquire customers.  The larger the number, the faster the company will grow.

Split testing is where 50% of your customers see one version and 50% see the other. It’s critically important to define which engine of growth your business is targeting and see which version in a split test is more successful along the relevant metrics.

One of the interesting anecdotes about Twitter from the video is that when they offered to give investors back their money, they had terrible vanity metrics (only a couple hundred users).  However, when you looked beneath the hood, the customer engagement of those few hundred users was off the charts.  It was an indication that something really interesting was going on here.  If you can prove that the engagement model works on a micro-scale, then you should worry about growing big.  You have to find early adopters before you can go to mainstream customers.  For a product that is network oriented, you have to get the network effect going.  Value of the network is proportional to the square of the number of members.  A single telephone isn’t valuable, but everyone having a phone makes your phone valuable.  Your immediate network is more important to you, so it’s possible to prove a network effect on a small community of early adopters (think Facebook on Harvard’s campus).


There is no formula to determine whether to pivot or whether to persevere.  Current model is to try some stuff and if it work, then great.  If not, then it’s a bummer.  Scheduling the pivot meeting every 8 weeks indefinitely will alleviate any apprehension about it.  What would I want to know 8 weeks from now that would help me to determine whether to pivot?

If a key metric to your success is how many users sign up to be paying customers, increasing that metric should be the goal of the business.  When you start getting diminishing marginal returns on your set goal, it’s time to pivot.  Many business see initial spurts of growth in a given metric and then have the growth taper off to a fraction of what it was before.  Every entrepreneur that successfully gets through a pivot wishes that they pivoted earlier.  The indicators of traction are always visible early if you look in the right place.

Winter is coming

Ries also threw out the proverbial “winter is coming” from Game of Thrones when describing the current startup scene.  He points out that it feels very summery right now; lots of capital out there and more entrepreneurs than at any other time in history.  What will matter when winter comes is whether a company actually creates value for users or is simply getting vanity metrics (like total number of messages sent).  Just like in the dotcom bubble, people are often using certain vanity metrics as a proxy for later success.

Ries says that we should have a new accounting system for startups and should be focused on helping startups that create value thrive so that they survive when winter comes.  He implied that the tremendous access to capital right now is allowing many companies to raise funds and look successful despite their inherent value proposition is flawed.  An accounting revolution could help to determine which companies are succeeding and which are in the land of the living dead.

Zombie Companies

The video also brings up the concept of Zombie Companies, which are startups that never really make it and just meander along.  These are a tremendous waste of people’s time and consumption of the global entrepreneur resource.  People stay with a stalling startup for many reasons; loyalty, the hope that one more product might make the difference, fear of pivoting based on customer feedback, etc.  However, many of the great success stories actually had ~2 years of failures before they hit it big.  Classic examples are Angry Birds, which didn’t make it big until their ~30th iteration, and Twitter, which was doing so badly that they offered investors their money back (some took them up on it, woops).

Reality Distortion Field

Ries says that all good entrepreneurs have a reality distortion field (famously coined to describe Steve Job’s way of convincing others to achieve the impossible).  The most fun time for entrepreneurs is when they’re in stealth mode, working on their alpha product, dreaming about how successful their idea is going to be.  When customers enter the picture, the bubble gets popped and reality starts to seep through.  There is a fine line between being a visionary and being a crazy person.  Sometimes it’s hard to know which type you’re following.


“Ghostbusters is the greatest entrepreneurship movie of all time.  Zuul (the bad guy in Ghost Busters) shows up at the perfect time for the Ghostbusters.  Most entrepreneurs are waiting for Zuul to show up.  In the movies, the key customer shows up when there is one dollar left.  In real life, when you’re down to your last dollar, you generally go down to your zeroeth dollar and then out of business.”

“If anybody is going to make the mistake of going into entrepreneurship to make money, definitely not the best way to make money. Go work at Goldman Sachs.  So much easier.  So much more certain that you will have a payday.”

“If you’re building a product that nobody wants, making it easier to use just makes people realize that they don’t want to use it sooner.”

“The companies that cause the maximum embarrassment are where you do a gigantic launch and then find out it’s a disaster.  Having a small number of customers is such a great asset.  Then you can feel free to experiment and try some really great stuff.”

It’s a great video and there’s a lot more in addition to the above.