Email best practices


I’ve been using email since 1980. At the time I was taught two things about using email: one, don’t put anything in email that you wouldn’t want to see on the front page of The New York Times (unfortunately innumerable people haven’t followed this best practice), and two, respond in no more than 24 hours – if only to acknowledge that you received the email.

I’ve tried to pass these best practices, and a few others, such as how to title email attachments, to my teams.

So I was pleased to see that I’m not only executive who believes in being responsive to emails. Here’s the snippet from The Wall Street Journal article How Take-Two’s CEO Powered Up, sub-titled Strauss Zelnick sought advice from a series of high-profile mentors in his quest to conquer the worlds of media, entertainment and videogames.

Mr. Zelnick says he has adopted a number of best practices from Barry Diller, Chairman of IAC/InterActiveOne example: “Respond to everyone, always within 24 hours,” Mr. Zelnick says. “It’s courteous and you never know where opportunities are going to come from.”

Mr. Diller was probably speaking not just of email, but of phone calls, faxes (!), and other forms of business communications as well.

A ringside seat at company naming trends


Crunchbase is a very valuable database of new companies and the people behind them. As such it has a ringside seat at trends in naming startups. I’m not the only person fascinated by the process of naming new companies. Sherwin Greenblatt, President of the MIT Venture Mentoring Service, presents a list of VMS companies who have changed their names at every monthly mentors meeting. And he admits it’s one of his favorite part of the meeting.

While you won’t find an entire category on my Mentorphile blog devoted to posts about company names you’ll find a few posts, including what I consider the best article on how to name a company that I’ve yet seen. But company names, like many elements in the startup ecosystem, are always changing, so the article by Joanna Glasner on Crunchbase News, Startup Names May Have Passed Peak Weirdness, is well worth reading if you are in the process of naming, or renaming your startup.

I remember being very puzzled as a kid by product names like Kleenex and Trix – these words weren’t spelled right! Only years later did I learn that the best way to trademark a product was by making up a word, like Kleenex, or changing the spelling of an existing English word, like tricks.

An then years later, with the advent of the world wide web and the gold rush for .com domains, did I see a tsunami of new company names.

Ms. Glasner’s article does a good job of listing the major ways that companies generate their names, and what’ going on within each category.

According to Athol Foden, president of Brighter Naming, a naming consultancy, founders are getting less comfortable with weird names.

Crunchbase News does an annual survey of startup naming trends. The latest trend is for startups to choose simple words to describe their businesses including companies like Hitch, an app for long-distance car rides, Duffel, a trip-booking startup named after the popular travel bag, and Coder, a software development platform. However, there’s a problem with having an overly descriptive name for your company – what happens when you pivot? This can happen to even large established companies. Apple Computer, Inc. had to drop the “Computer” when computers became a small portion of their product line compared to the iPhone. And iTunes has become a catchall for music, movies, TV, and software used to sync your iPhone with your Mac. What I like are names that are evocative, like Amazon – the largest river in the world, not descriptive. With descriptive names, one pivot and all that brand equity can disappear as your descriptive name becomes obsolete. When “fried” became a bad ting for you diet Kentucky Friend Chicken was forced to change their name to KFC.

Creative Misspellings

One of the most wide-spread, and frankly easiest way to create a unique name is to purposefully misspell a common word, like Flickr, the early photo-sharing site.

However, creative misspellings are getting less popular, Foden said. Early-stage founders are turned off by the prospect of having to spell out their names to people unfamiliar with the brand (which for seed-stage companies includes pretty much everyone).


It seems like only a few companies with pun names have gone public or been acquired, according to CrunchBase. Both Foden and Glasner are in favor of seeing more Internet startups with pub-based names. I’m afraid I can’t agree, as I find that often people just don’t get puns. And then when they do, they can be irritated at the cuteness of the pun. My original name for the company that became Course Technology, Inc. was Of Course, Inc. But the straitlaced VCs at Greylock hated that name and told me in no uncertain terms that “No company with a cute name would ever go public.: Of course, that was before the days of Yahoo, Google, et al!

Made-Up Words That Sound Real

If you are clever enough to pull this off it can be a real win, as not only will you be able to snag a valued .com domain, but you will also be able to trademark your name. Names like Invocable and  Locomation are good examples.

Normal-Sounding Names

In the industrial age companies had boring and obvious names like Standard Oil, U.S. Steel, General Electric and International Business Machines.  But the problem with the latter two, and many others, is that their names quickly became shortened to just their initials: GE and IBM, not to speak of AT and T. Know what that stands for?

Compound Names

There’s a major category that Ms. Glassner leaves out of her article, the category that probably works best now that virtually every word in the English language has either ben taken by a startup or by a domain squatter. That category is the compound name. Two of the best known examples being Facebook and Microsoft . The approach is to concatenate two short words, like Bitpipe. I’m sure any good coder could whip a program to auto-generate compound names. In fact domain squatters probably have. But even so, this is a proven way to generate an easy to spell, easy to pronounce company name.

Gud lukk!

The name game – naming is changing

Midsection Of Woman Holding Name Tag With Text

One of the biggest challenges for startups has been and still is coming up with a name for the venture. Decades ago, when I began my startup ventures with Real Time Audio, which I thought was a great name for a sound reinforcement company, one didn’t have to worry about urls. In fact I was so naive at the time I didn’t even worry about trademarks!

But today’s founders have a lot to worry about when it comes to naming and I have several posts on Mentorphile on the subject.

Sherwin Greenblatt, the head of MIT’s Venture Mentoring Service, always enjoys the monthly meeting time slot when he announces the name changes of VMS ventures. It’s a favorite of mine as well. Sometimes the changes are for the better, other times we collectively scratch are heads and wonder if the new name is actually worse! There’s always a few laughs mixed with groans at the oddball names.

The good news is that according to Joanna Glasner‘s article on TechCrunch Startup names may have passed peak weirdness. She quotes Athol Foden,  president of Brighter Naming, a naming consultancy: “As we reach the edge of strangeness… they’re saying: ‘It’s too weird. I’m uncomfortable.”

Crunch News does an annual survey of startup naming trends (news to me!) and the trend is that startups are choosing simple words that describe their business, including companies like Hitch, an app for long-distance car rides; Duffel, a trip-booking startup named after the popular travel bag; and Coder, a software development platform.

Joanna Glassner lists the common ways founders generate unique names:

  • Creative misspellings
  • Puns
  • Made-up words that sound real
  • Normal-sounding names

For some time now my advice to startups is that if they have some capital to invest they should simply buy a name that meets the common naming rules, that will save them much time, effort, and anguish. And domain squatters have plenty of names to sell. If you can’t afford to buy a name, one method that works for many companies is compounding two simple words; the best example being “face” and “book.”

While it’s true that your name is your brand and .com is the most highly valued domain, both are shifting. Companies change their names or create new parent companies like Snap for SnapChat or Alphabet for Google and other ventures. And even Alphabet eschews the .com domain, Alphabet’s url is

One of my current mentees is in the midst of name change – I’m looking on, hoping they can improve on their current name, which doesn’t seem hard to do, but it is!


The value of diagrams

data flow

I’ve posted previously about the value of diagrams in presenting your business. In fact by creating some of these diagrams you will also better understand your business.

In discussing the value of diagrams for founders with MIT VMS mentor Beth Kahn she mentioned that she had a number of types of diagrams she would share with me and the mentee. Thanks to her for providing a full deck of diagrams, of which I’m just going to present a few.

Process diagrams are useful in three ways:

  • Information: how decisions get made
  • Activities: who takes action
  • Products: how the product is delivered
  • Money: the flow of funds

There are three types of process maps:

  • Ecosystem: who are the stakeholders
  • Workflow: how your product is built or your service is delivered
  • Value chain: how value is added during the product lifecycle

I generally ask founders to first map their ecosystem: who are the suppliers? competitors? sales channels? value-added resellers? service providers? substitutes for your product? analysts who track your market segment?

Here’s an example of the ecosystem of the stakeholders in a company called LimeFinder.


Here’s the value chain for an electric car:

value chain electric cars

Here’s the work flow diagram for LifeFinder:

workflow Limefinder

There is one other diagram I will share with you that outlines the customer discovery process, which should be the starting point for founders:

customer discover

Once you actually have a product and are selling it you need to understand who are the players in the sales process:

  • Decision maker – makes the final decision to purchase
  • Influencer – can sway the decision maker but is not the decision maker
  • Economic buyer – issues the PO or signs the check – not necessarily a user of the product
  • End user – the actual end user of your product or service
  • Early evangelist or product champion – an early adopter who advocates for your offering
  • Saboteur – someone who seeks to undermine the adoption of your product due to real or perceived negative impact of your offering – you may be seen as a competitor

These are the major types of diagrams that are useful for both learning about your processes and presenting them to interested parties, such as investors or candidates for hire.

If a picture is worth a thousand words, in business I would say a diagram is worth ten thousand words. Yes, they are a lot more work that just snapping a photo with your smart phone, but the work that goes into them with have real value in proportion to the time you invest in developing and modifying these diagrams for your business.

What’s the highest bandwidth communication medium?

nyt reporter

My introduction to email came in 1980 when I joined Software Arts, the inventors of VisiCalc, the first electronic spreadsheet. We all had VT100 terminals on our desks that were tied into a Prime minicomputer. The Prime was used for software development as well as for our internal email system. I quickly became a heavy user of email, as was everyone else in the company. We had a connection to the ArpaNet, the precursor to the Internet, and I could have sent email to scientists and researchers around the country, who were the only users of ArpaNet, but I didn’t know any of them!

Email has a lot of advantages, but for me it had several specific ones:

  • It enabled me to communicate asynchronously with everyone in our company as well as with our distributor Personal Software, located two time zones away. Trying to get people together for a meeting wasn’t easy and often was totally unnecessary. Email worked well as a one-to-one and one-to-many communications medium.
  • I hate making phone calls. People’s voices didn’t sound quite right, as the phone company restricts the bandwidth of the telecom system in order to increase capacity. And you never know if someone is paying attention or not while talking to you. I could go on but everyone is familiar with the hassles of phone tag and the annoyance of voicemail
  • It served as a record of my work and a to do list. Email wasn’t designed to do either, but by putting most work related communications into a written form I could keep track of what people “owed” me and vice versa.
  • It allowed me to work from home and feed my work addiction by enabling me to send and read emails every hour of the day or night.

Even today with Facebook Messenger, WhatsApp, Signal, and dozens of competitors to plain old email, I’m still a heavy user. But neither email, nor phone calls, is a high bandwidth communications channel. Face-to-face or F2F is by far the highest bandwidth channel. I was reminded of this today when reading the New York Times article Digital Privacy Is a Big Concern in Europe. For This Reporter, Too, subtitled When the investigative journalist Matt Apuzzo moved from Washington to Brussels, he noticed that distrust had a different focus. And he adjusted some of his own tech tools. This story is part of a series that The New York Times runs about how journalists use technology in their jobs and in their personal lives. I read three newspapers every day: The Times, The Wall Street Journal, and The Boston Globe. I have great respect and admiration for journalists. But beyond that I believe that mentors need to act like investigative journalists themselves. We need to find out what’s the story behind a founder’s presentation. Asking the right questions at the right time is one of the core skills of both journalists and mentors. And, of course, communicating with our mentees outside of our F2F meetings is important.

What are the most important tech tools for you as an investigative journalist?

Tech is great, but there’s no substitute for personal relationships. I prefer face-to-face conversations whenever possible, and I almost never record them. I use small, discreet notebooks like the Moleskine pocket journal. A lot of my interviews are over coffee, drinks or meals, and I want something as unobtrusive as possible at the table. I love the feel of the Rhodia pocket webnotebook, but let’s be honest: I’m not picky. Some of the best, most surprising nuggets of information have been scribbled on napkins or the backs of envelopes or tapped in text messages to myself.

Face to face communications is considered so important by the MIT Venture Mentoring Service that VMS does not support remote mentoring of any kind.  Aside from occasionally accommodating mentors who may be traveling or otherwise not able to come in to MIT by using a speaker phone, the emphasis is always in meeting founders F2F and in teams of mentors. Why is face to face so powerful in this technology mediated age? For one thing we all have grown up talking to those around us. We had to learn how to use the telephone and then the computer and smartphone. But F2F also provides a much broader field of view than typical video conferencing tools. Facebooks’ new Portal uses AI to move it’s camera to follow the person talking. While I haven’t tried this, I’m sure it’s an improvement on Skype or Zoom. But sometimes when meeting with a team of founders I like to look at the members of the team who aren’t speaking. As a mentor you can learn a lot about team dynamics by watching the team while one of them is talking. Are they paying attention? Are they leaning in, which demonstrates interest, or leaning back which demonstrates disengagement or even boredom? Do they have their arms crossed, which often signals anger or disagreement? Are they looking at their phone rather than at the people in the meeting? These are important questions which are impossible or hard to answer during a phone call or video conference.

Humor is important in all human relations, but even more so for founders, who are often very stressed out by the rigors of startup life. I find it’s a lot easier to crack a joke during an inn-person meeting than over the phone. And most of us know that email is the worst medium for humor. Without the nuances of vocal tone and inflection and non-verbal communications, humor often falls flat, or worse yet, can be misinterpreted and even come across as offensive.

I also find it’s a lot easier to start off a meeting with non-business chat, which helps build personal relationships amongst mentor teams and with founders, than using a video call. Perhaps it’s because none of us have grown up with video calling, but we seem to see it as a more formal and constrained medium. Perhaps millennials and Generation Z  don’t have this issue.

For me the goal of a mentor meeting is conversation, not presentation. So I don’t encourage founders to start off meetings with their decks. Conversations help build trust, which is vital in a mentor-mentee relationship. And I often coach founders to treat sales calls as conversations, dialogs, not monologs nor presentations. We learn a lot by listening; we learn little while talking.

Of course there are drawback to any medium and F2F is no exception. People can talk over each other, they can mumble, they can pontificate, they can wander off the subject. Having an agenda, objectives, and structuring the meeting can help avoid these problems.

And speaking of problems, I learned the hard way that problems need to be solved face to face. While it’s far easier and faster to send an email doing so can make a problem worse, not better. If the person you need to communicate with is out of town then pick up the phone, even if making phone calls seems foreign to you. Problem solving needs real time communications, and though text messaging is real time it is a sparse medium unlike the rich medium of face to face meetings.

So when you need to communicate, choose your channel wisely. But keep in mind Times reporter Matt Apuzzo’s words: Tech is great, but there’s no substitute  for personal relationships.


“Mentor” now chasing “Innovative” as most used and misused business term



I was dismayed by the use of the word “mentor”  in the Business Insider article by Rosalie Chan Larry Ellison says that Oracle was once a week away from not being able to pay employees — here’s the lesson he learned from the experience.

Ellison hosts a cocktail reception to mentor startup founders each year. Last week, he hosted the founders of 22 startups at his San Francisco home — and eWeek was in attendance to report on the advice he gave.

First of all it is impossible to mentor 22 people at once! Second and perhaps less obviously, mentoring is not a one-time thing, it’s relationship between the founder and the mentor that can last months or even years. Larry may well be advising 22 startup founders and perhaps he mentors a handful of them – the article doesn’t say. But mentor is starting to get overused just as the words innovate and innovation have before it. This blog devotes an entire category to mentoring.

However, the article does include two good lessons learned by Larry Ellison when Oracle was a startup, not the behemoth it is today, 40 years later.

First, is to balance doing whatever it takes to pay the bills with whatever it is that you actually want to do. One of my newest mentees is struggling over earning money from a first client, but a client that’s a real outlier on the distribution of target clients. The number one need in all startup is cash. Even if you are sharing an apartment with six other engineers and living on ramen noodles you still need cash. So I totally agree with Larry’s advice – do whatever you need to do to earn cash even if it’s NRE – non-recurring engineering. 

Second, once your startup crosses the chasm and becomes an on-going concern you can’t get complacent. As Ellison says:

The old solution to customers’ problems may no longer be the best solution. When you see that, it’s an opportunity—or a threat,” Ellison said, according to eWeek. “It’s our job as founders and developers to constantly change our companies based on technology available today that wasn’t available yesterday.

And like every other company, Oracle is realizing that AI is not just a science experiment any longer, Oracle has been focusing on its autonomous, AI-powered database and its cloud solution.

As a mentor I hope that the it remains a term of art, unlike innovative, too often used and misused as in “new, innovative” which is redundant, as the very definition of innovate includes the word new.

innovative |ˈinəˌvādiv| adjective(of a product, idea, etc.) featuring new methods; advanced and originalinnovative designs | innovative ways to help unemployed people.(of a person) introducing new ideas; original and creative in thinking: an innovative thinker.

Well I’ve hit my pedantry quota for the day!



What’s your product narrative?


I’ve posted previously how at Amazon developers’ first step in new product development is to write a press release about the product they plan to create. But Scott Belsky in his new book The Messy Middle takes narrative well beyond the press release.

Carmine Gallo, one of my favorite business writers, writes about Belsky’s book in the Forbes article An Early Uber Investor Reveals A Creative Strategy To Build An Irresistible Brand. His key take-away from the book is that founders should build their narrative before they start developing their product.

According to Belsky, “Most entrepreneurs jump in and build a product. They’ll spend months, even years, building an MVP (minimal viable product). Right when they’re about to share it with the world, they realize it doesn’t resonate with consumers. People don’t understand why it helps them and why they should use it instead of something else.” Belsky recommends that entrepreneurs avoid this problem by starting with a story before the product is built—paint a picture of what the world will look like when the product is finished.

Belsy recommends that developers build a private web page for the product that should answer the following questions:

·     What inspired the idea?

·     Why does it need to exist?

·     Why is it relevant?

·     How does it make the future better?

The narrative services not only as the roadmap to how you develop your product but how you will market it as well. All stakeholders, from investors, team, or partners are helped to visualize the future.

Being able to recite a narrative—tell a story—about a future customer and how the product will solve a real-world problem is a powerful exercise that few leaders do in the early stages of the development process. “It’s very powerful and most teams don’t spend a lot of time on it,” says Belsky.

It’s a truism that investor pitches need to tell a story, but Belsky’s concept of the narrative goes beyond that to acting as the lodestar during the entire lifecycle of the product.  I see Belsky’s approach as similar to what I recommend to founders, using the journalists who? what? why? why” where? and how? to tell their products story. But what is different about Belsky’s approach is that it helps everyone envision the future. He gives a great example, how Garrett Camp, co-founder of Uber imagined a future where where everyone could call up a private driver, something only reserved for wealthy elites at the time. He imagined it as a superpower that ordinary people would have at their fingertips, literally. The story evolved into Uber’s first tagline: Uber is everyone’s private driver. Journalists report on the present; you narrative is a report from the future!

This also ties in with how Alan Kay recommends founders develop their products which I wrote about in the blog post How to invent the future. Belsky’s put his money where his book is, he was an early investor in Uber, in addition to founding Behance, an online portfolio company for creatives that he later sold to Adobe for an estimated $150 million. Today, Belsky is Adobe’s chief product officer and a venture capital investor.

He uses as an example Garrett Camp. the cofounder of Uber. (Belsky was an early investor in the company) Before Uber was a product—or a company—Camp was working on the narrative. Camp began to imagine an experience where everyone could call up a private driver, something only reserved for wealthy elites at the time. He imagined it as a superpower that ordinary people would have at their fingertips, literally. The story evolved into Uber’s first tagline: Uber is everyone’s private driver.

To recap, while Jeff Bezos’s practice of writing a press release for a new product that has yet to even begin development acts as a guiding light, a narrative envisions the future how the product will change life for consumers. Both approaches will not only guide developers but help them communicate the nature and value of their product to all stakeholders from investors to users.