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The Vanguard

As a startup CEO, you’re probably looking forward to your next board meeting with a similar level of anticipation that is often reserved for dentist appointments. Who doesn’t like getting naked in front of a committee whose sole power is firing you, and spending 2 hours in what is basically an audit followed by a session of unsolicited advice? And while the former is almost exactly true (read your bylaws) and the latter is too often the case, board meetings are an opportunity to get into the habit of keeping your company in order. But doing them right requires:

  • Understanding…

…Dedicated to the memory of the late David Ladd, my best and favorite board-member ever.

“Today is a great day. I am going to a startup board meeting”… said no one ever.

And yet if you are an investor or a founder, this is part of your life, and a key way you make an impact on companies you’re involved with. Let’s spend five minutes discussing what this means and how to do it properly.

This post is the first one in a series about startup board meetings,

The Basics — That Almost Everyone Gets Wrong

You may have been appointed to the board to represent your VC…

Last week, we had the good fortune of having two Masters of Sales join our meeting to shed some light on best practices in Sales:

  • Pete Kazanjy, Founder & CEO of sales performance analytics co. Atrium, and the author of Founding Sales the startup sales handbook.
  • Alon Zaibert, Founder of Emotional Relevance and the travel industry’s leading sales coach.

Our beloved lead-generator-in-chief Shani Shoham, Founder and CEO of 21 Labs and advisor to moderated.

This post will attempt to summarize the main points from the event…

Initial sales in a startup should be done by a founder.

There’s so many reasons why that’s true. For a detailed “why” and “how-to”…

You are a smart, scrappy entrepreneur. You are hustling, trying to get in front of customers, partners, investors. You are closing your first pilots, your first seed investments, your first distribution partnership. And you are staying organized, right? You probably have a spreadsheet somewhere, or a beautiful Coda shared doc. CRM? That’s for when you have salespeople, lots of them. Right? After all that’s how it worked in your previous company — the salespeople used Salesforce, the creators used Jira (or whatever). And you, as a founder, are a creator.

No you’re not. You’re a business leader. …

Follow the path on the left

If you read The 7 Pilots That Will Crash Your Startup, you know all about the pitfalls of a pilot-driven sales / business development process, and you’ve seen a list of tell-tale signals that a proposed pilot stinks. Of course, the bigger question is how to do it right — what is a strategy for successfully navigating B2B business relationships that ends in profitable, win-win customer relationships.

It’s About Alignment

What you want to get out of a given pilot depends on where you are in your product life-cycle. If you’re at an early stage of product development, you want an environment to…

You are a brilliant engineer and/or product manager. You saw an opportunity in a market, teamed up with your favorite co-founder(s) and hacked together an MVP. Through personal relationships, endless cold-calling or some elevator pitch at an industry event you managed to land your first customer.

Early success led to the second and third. You raised funding and turned the company into a business. You even hired business development or sales people. You have a great pipeline, the trend-line is up and to the right. Marketing? You have a website, you have beautiful PDFs you send customers. Your business development…

A quantitative assessment of market conditions.

If you run a startup these days, there are some truisms you keep hearing — “the party’s over”, “conserve cash”, “extend the runway” and so forth. Most investors are basically saying “Expect less money from us and our colleagues”, and “we’re in a recession, so things will slow down”.

James Reynolds’ “Waiting It Out”

While these statements are obviously true on the macro level, your day-to-day is on the micro level:

  • Do I lay people off? How many? Which part of the organization? Engineering? Sales? Business Development?
  • Do I try to engage my customers or are they all sheltering in place with pillows over their…

So you’ve been doing this for awhile now. Maybe you’ve gone through the initial excitement of idea / team / frenzied MVP development / seed funding. Maybe you’re even further along — reached some level of product-market fit, raised an A or B round, and are trying to grow the company and the metrics.

Here are some things you’ve most definitely noticed already:

No One Prepared You For This Job.

Unless you’ve been through the wringer successfully multiple times, sooner (usually) or later you’re going to be doing things and finding yourself in situations you’ve never been in before. Maybe it’s going to investor meeting after investor…

If you haven’t been living under a rock for the last couple of years, then you know that AI is now all the rage and personal assistants– like Alexa, Google Assistant and Siri are having their moment in the sun. If you’re working in or around tech, maybe you’re wondering “how can my company build its own personal assistant / bot / voice interface”. Look no further — as in the next few minutes I will explain the basics of the natural-language-interaction stack, and also where to get it!

Note: While this is a review of voice assistant tech —…

…this post was first published on

Having founded WorldMate and Desti (which also swallowed, not a week goes by without me being approached by an entrepreneur who has started / is starting / is contemplating a travel startup. The vast majority of these follow the following pattern:

  • The pitch will start with “online travel planning for X is so hard…” where X is any of a dozen classes of trips / travelers — from garden-variety leisure travelers to vegan millennial honeymooners who want to do all their planning on their iPhone
  • The solution is an app / site…

The Vanguard

Technology, Startups and Strategy

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