No Email please, we’re collaborating.

Startups rely on constant, open sharing of information across all functions in order to have a shot at becoming a company. However, the most common tool for communications – Email, like cubicles in office layouts, encourages silos of information rather than easy, frictionless, and continual sharing.

I believe collaboration only happens when it happens all the time. It is not an activity that can be scheduled in meetings or forced via specific/distinct applications foisted on employees. I  think it needs to be a central part of a primary nervous system used in a startup.

While multiple attempts have been made to ‘fix email’ (ShortMail, MinBox,…), I think a bolder new approach may be required – no email. Instead, replace email with a simpler communication system that enables open participation across all employees in a startup.

The idea is quite simple – all employees ‘publish’ everything they do, and others ‘subscribe’ to whoever they need to subscribe to – in order to do their work. I call it NAIL, a portmanteau of NoEmail.

There are three canonical streams of communications that need to flow in such a system:

Work/Activity: Everything an employee does is published here. Code/dev/test/get/push/A-B/Customer-prezo/Company Ops updates/HR/Admin
Collaborate: Anything that requires two or more people to work together. Includes click-to-video, click-to-talk
Educate: Everyone’s capture of what you learnt + what you want others to learn. resources, configurations, external-resources, blogs, faqs,…

Streams in the flow

The information flowing in this communications system can be presented in a simple way using a (Dave Winer’s) reverse chronological streams of the three categories. In the interest of fast browsing, snippets can be limited to 2 lines of text+links or even 140 chrs in a nod to the popularly accepted tweet limit.

Underlying these three flows are a robust message bus, calendar system, and other Voice/Video-over-IP support. (Think UDP-fast).

A minimum feature set for such a system is:

  • Allow anyone to subscribe to anyone else.
  • Accounts for people, groups, and systems (let the db NAIL its pain)
  • @reply, @group-reply, @DM, @Group-DM
  • Archive everything. Make it all searchable.
  • Click-to-multiparty Video Call, Single click-to-multiparty Voice call built in.
  • Recommendations section of suggested people + content to follow for new employees and all users. Min-list by function, then suggest by interests, activities.
  • Must be Mobile from day-1.
  • Encourage Photos/other-media capture (especially in collaborate stream)

For communications external to the startup, use email as a connector to/from the primary communications system. For incoming emails to a user, map it as @user in to their “Collaborate” stream.mapping email to message

For outgoing email messages, map the message and attachments to standard email and also publish to ‘Work’ stream. Private outgoing messages can be DM’ed which suppress publish. mapping message to email

I have no idea if something like this scales well to large organizations or large groups but for small (<10?) work groups, I think this just might work better than email. Of course, in true startup spirit, if you can hack together NAIL on top of Twitter, even better…



my values as an investor: an open letter to founders

dear founders,

over the past few years, i have invested small amounts of money where the founders have given me an opportunity to do so. for each such opportunity to share in their quest, i have learnt something – and i am thankful.

as i talk to the founder(s) and the team, i find that some teams are naturally curious and want to know why i’d invest and what my relationship to that startup would be. one word that rarely gets used in these conversations and questions is ‘values’. i have written previously about startup values and as an investor, want to make sure that founders talking to me about angel/seed investments understand my values.
my values are expressions of some simple viewpoints and actions i strive to live by and bring to the table as an investor. these are:

  • are you taking enough risk?
  • optimize for the long term – always.
  • do I identify with, understand, and agree with your mission, not just your idea, technology, products, and startups.
  • the small amount of money ($5K to $50K) i invest carries with it the ability to turn to zero or be padded with zeroes. if it enabled you to make an effort you couldn’t otherwise make, it will be well spent.
  • while i will make an effort to help whichever way I can, you should understand that:
    • i am not your product manager
    • i am not your rolodex. access without context means nothing.
    • i am not a visionary. i am investing in your vision which is tuned constantly, by every day interaction with your users, technologies, products, and your peers. chase what you see, not what i or others ask you to chase.
  • i have failed many times at many things. i have learnt from failures. successes taught me more, but failures caused me to learn more.
  • while you focus on user growth and customer associated metrics, don’t lose sight of personal growth metrics.  i pay particular attention to personal and inter-personal growth within your startup.

and finally, the most important metric for me – your success as a founder isn’t measured in dollars raised or valuation or money earned for investors, it is measured in how many other people did you make successful. this is my yardstick for a founder.


The best question VCs can ask you and you can ask VCs.

When founders and startups meet with Venture Capitalists, Angel investors, or potential advisors, most of the time is spent talking about the founder’s insights, technology, product, or the market they intend to innovate, disrupt, or create. In my experience across both sides of the money-table as a VC and as a founder, the hardest and the most insightful question is often not about the knowledge founders or startups have, but rather, what have they learnt. This concise question embodies just about everything the VCs want to know about you as well as your company.

What you “know” is the platform that you stand upon and the framework for building your product. What you “learnt” is the  valuable part that allows you to create something of value, hopefully – a lot of value – for your customers. This is where you have the opportunity to figure out something that others have not understood yet. Thus, ‘learning’ is your unfair edge in an otherwise irrational pursuit where the odds are against you most of the time till you trump them with your learning, not knowledge.

If knowledge is velocity, what you have learnt determines your acceleration, i.e. the second derivative.

(Thanks @jessefarmer)

This seemingly simple question is in fact quite complex. When a VC asks you this question, they are judging multiple things at the same time:

what does it tell them about your learning style and pace of learning
what does it say about your willingness to learn
what does it say about your willingness to fail while learning
how does it educate them about your market, your technology area, your competitors

And when VCs ask this question of their portfolio companies, they are keenly focused on the acceleration (or deceleration) of your company, not the somewhat static ‘knowledge’ you started off with when they invested.

I also think this is also the question founders should ask potential investors. Rather than talk about fund size, investing philosophy, market-trends,.. (all things you must know before meeting them), ask them the following two questions:

1. What have they learnt in the past 2 years.
2. What new behavior, investments, or market developments do they expect to occur given that learning.

If you hear answers that are rambling, unfocused, or evasive, it will tell you more than their past record or their current investing ‘thesis’.

When you hear clueful answers, it should signal to you that the VC asking this question is more likely to be thinking ‘long-term’ vs. ‘flavor of the day’. VCs that can discuss what they have learnt and how they see it influencing the next few years are rare and good for early stage startups.

p.s. The words ‘learnt‘ and ‘learned‘ are interchangeable here. i have a preference for using ‘learnt’, having learnt my english language skills reading newspapers and listening to the BBC in India and later during graduate studies in Canada. “learned” is the more commonly used form of the word in U.S.A.



Picking Advisors for Your Startup

Somewhere in the entrepreneurial journey from an idea to a startup, founders will often meet friends and colleagues to brainstorm and develop their ideas. In some of these conversations “Oh I think you should meet XYZ person who’d be great for feedback” event happens multiple times. Some of these people are potential advisors for your startup. Here are some thoughts on how to think about advisors at various stages of the idea-to-company odyssey.

Remember your Advisor’s job is to help you make non-obvious choices in the face of imperfect and sometimes non-existent data. Recruit accordingly.

The Six Cardinal Directions of Effective Advisors

1. The most important skill an advisor can bring to you and your idea is a way to improve your idea by asking you the right and often ‘hard’ questions. People who want to replicate the success they had even if in the same area as your startup by repeating the same approach/execution/recipe are not the right ones for you. Beyond the usual “Oh Its nice” or “Its great” responses, listen for something that signals that your idea made them think. If they then come back with questions you haven’t yet asked yourself, they may be a good match as an advisor.

2. Don’t confuse mentor with advisor. Mentors are a rare breed of individuals. They are good at asking questions and making you learn regardless of what they or you are working on. Conflating the two may not necessarily be good for you or your  startup.

3. How do they talk about failure and what they’ve learnt from the failure matters as much as what they’re successful at. Ask them what they have learnt in the last three years as a result of a failure that has now changed their thinking or behavior in a meaningful way.

4. Make sure you ask them if they have played the role (paid in equity usually) with at least one other startup. You want to ensure that they are not going to play ‘Product Manager’ for you with good intentions and potentially disastrous results. Advisors are not going to invent your product or your market or your product-features. They can be invaluable in pointing out the voids in your product strategy or feature-list or competitive dynamics. Advisors who are good at pointing out what doesn’t exist are often far more helpful than the ones who suggest a specific feature or two.

5. Ask them for a specific commitment of time, effort, and introductions you expect from them over the first year of your collaboration. Introduce them to your other advisors and create some opportunities for them to collaborate – enabling them to think beyond their usual domain is effectively delightful compensation for them beyond the equity you will give them.

6. Your advisors are not your investors. Keep these two roles separate. While there may be some overlap, they have distinct responsibilities for you and your startup.

The Entourage Approach

For certain startups and founders, an ‘entourage’ may be more appropriate which functions as early adopters and influencers in your marketplace. Perhaps the best example of this approach was where @tonysphere and other founders were well connected and signed up 26 advisors to help them push to a million users within a year and an acquisition by AOL. If you’re not as well connected as the fine folks at, this may not be the way to go. A weak entourage is baggage, not balloons.

Advisor Compensation

I will write about Advisor compensation in a future post but here are some guidelines for silicon valley startups:
for early stage (between idea stage and funding) formal advisors, expect to share about 1% equity which goes down to approx 0.25% for seed-funded startups and often between 0.1 and 0.25% for developing stage startups. Typically the equity vests monthly over a year without any cliff and there is no other compensation (e.g. cash).

On Startup Values

In Silicon Valley, ‘startup’ is one of the most common and the most valuable word one hears about town. Freely bandied about by those who were once in a startup, are currently in a startup or want to start one, the word is a badge of pride for those who have experienced it.

Less understood is what goes in to creating, sustaining, and growing a startup.  Founders, money, employees, investors, technology and products are necessary but not sufficient ingredients for startup success. One of the crucial ingredients one rarely hears about and is usually not understood by most is Startup Values.

Values is not capital you can raise from VCs. Values are reflected by a few critical qualities founders and startup employees must either have or recognize and cultivate. Values are not transplantable a few months or years in to the journey. More than a few (very smart) founders I know dismiss it by saying “We will focus on values once we’re successful”. Wrong! Startup values are like a seed you plant on day one alongside your ideas and it needs the same care and nurture as your technology and products.

integration symbol

I have always felt that the key startup values are:


Honesty in a startup primarily means interpersonal honesty between all the employees. Honesty is also the fabric that links objective measurement of a startup’s progress along chosen metrics and the startup’s stated goals.  In between founders and employees and between multiple founders in the case of cofounders, honesty is the only way to sustain a working relationship.

How to get it right: Communications is a key component of honesty. Founders and CEOs must ensure everyone understands where they are, where they are going, and how they are going to get there. You can never communicate enough and email is perhaps the poorest mode of such communication. In a small team, a 5 minute sync meeting every day or 15 minutes every week should suffice.

How do you know its not working: When you find yourself ‘marketing’ or spinning the truth to your coworkers, you must have the courage to admit you’re not being honest. In a startup context, some typical phrases that should serve as warning signs include “It will be easy to raise money”, “Hockey stick growth is just a couple of features away” or “We can always acquire users through advertising” or “There will be lots of buyers for the company if you get to X number of users”. When employees hear such things from their CEO or founders, ask questions. If startups hear such words from their investors, take a long hard look at their track record and at your balance sheet.


In a startup, you often recruit friends, referrals from friends, and those you respect to the mission at hand. Flexibility doesn’t just apply to founders/CEOs but to everyone. Venturing in to areas adjacent to your area-of-comfort as far as your skills go will be often required. A good startup team at work is like an ongoing game of 3D twister. Flexibility, once it becomes part of your startup’s DNA, makes it better at evolution as well as adapting to challenges.

How to get it right: Be open when CEOs/founders ask you to do something beyond your area of expertise or experience. Voice your fears openly, express your challenges clearly. Ask for help when you need it, offer help when you see someone needing it.

How do you know its not working: When you hear CEOs/founders/employees express “Thats not what I was hired for”, it should serve as an early warning sign. If your startup is not good at handling failure (see below), it will be hard to build a culture of flexibility.


A startup is (most of the time) an irrational pursuit with a high probability of not following its initial trajectory. Creativity, exercised at all levels from infrastructure/technology to design & delivery, is the most powerful value you can have to combat existing products you compete with or to highlight the one thing you excel at versus all others. It is an essential part that improves flexibility and helps a startup to navigate competition that may be better capitalized or entrenched. At a personal level, creativity is an everyday expression of how things get done in a startup with limited resources and money.

How to get it right: If a startup, prior to success (users or revenue) can point to something unique that they do that others do not, it is likely creativity that is at work.

How do you know its not working: If your coworkers, founders or CEOs talk too much about “This is how I did things at company XYZ” when it comes to talking technology, products, or your market, you should fear that your startup lacks creativity. More than any other area, past work is really not a good indicator of the future in startup.

Failure with grace

This is perhaps the most talked about ‘lean‘ (e.g. smart) aspect of a startup’s journey from idea to success and may be the most misunderstood. No one likes to fail even though fail-fast, fail-often, fail-early is an easy set of words to say. I believe failure with grace is not just for complex systems. Seemingly trivial interactions between team members are often predicated on success, not failure and unless everyone in the team in a startup can freely (and honestly) express failure, re-calibrate, and have a chance of re-delivering, each failure will be costly in an interpersonal sense.

How to get it right: All employees must be comfortable in saying “I failed at XYZ and here’s how I am going to get it right”. When there is no interpersonal unease or ‘cost’ to saying/hearing it, you will know your team is on the right path to integrate failure as a navigational mechanism to find the right direction.

How do you know its not working: When someone in the team fails ‘silently’ at a task or two and begins to find excuses vs. ‘claiming the failure’ is a dependable sign of lack of this startup value. Silent failures are deadly in all kinds of systems, and deadlier in a startup.  A failure not owned at the first sign of it is a toxic seed that will threaten startup success.

Measurable heuristics

Every startup is based on a few early ideas about how their world ought to be. Startups must be honest with themselves to figure out the right measurements for their heuristics about how their product will evolve.  Measurement and heuristics are the yin and yang of startup ideas.  One cannot exist without the other or has no meaning without the other.  A right balance between these two is often the hardest value to get right in a startup.  Too much heuristics to guide you may mean unconstrained wander before you find your market while too much measurement will surely constrain good thinking with possible false positives and negatives. Measurement confirms innovation, but rarely initiates it.

How to get it right: Teams must have the discipline to listen to measurements for determining growth and listen to heuristic thinking to set the first vectors for experimentation.

How do you know its not working: Each discussion of a new feature, product, or change must be accompanied by “how will we know its working” discussion. Success is not pornography that you will know it when you see it. If you cannot measure success, it is likely you do not yet know how to go to there.

I hope you found something worth thinking about in this post and I’d love to hear from you (comments below or tweet  @rohit_x_).

In a related future post, I will be writing about working with VCs that share these values and help your startup enhance them.

This work is licensed under a Creative Commons Attribution 3.0 Unported License.