I'm a partner at Redpoint and write daily, data-driven blog posts about key questions facing startups including how to fund raise, startup benchmarks, management best practices and team building. Join thousands of others receiving these blog posts daily by email.

The Nature of Leverage in Fundraising Conversations Has Changed

Leverage. It's the key to negotiating. Classic negotiating books like Getting to Yes define the BATNA, the Best Alternative to Negotiated Agreement. If you were to walk away from a conversation, what's the next best choice? The BATNA singlehandedly creates leverage in negotiating.


With Smart Software, Sell Ironman Not Robocop

When buying machine learning enabled software, it's easier to sell like Ironman than Robocop; a product that complements and augments the user's skills rather than a true replacement. As machine learning continues to become a key differentiator among SaaS products, a secular and positive trend, startups are learning how to sell the promise of the software better and better. These are some of the objections customers raise during those sales pitches.


The 12 Things I Know About You

Here are the first three. You have a great need for other people to like and admire you. You have a tendency to be critical of yourself. You have a great deal of unused capacity which you have not turned to your advantage.


Chained Probabilities in Startup Business Models

In 1983, Lorne Whitehead, a physicist from the University of British Columbia proved he could knock down the Empire State Building with 29 dominos. A domino can knock over an other domino one-and-a-half times its size. Whitehead's theory concretely demonstrates the power of a chain reaction. Like a series of dominos, a startup's success is a chain reaction.


The Question to Ask Before Starting a Company in 2016

The Roman Turtle

My father keeps a copy of Michael Porter's Competitive Strategy on his bookshelf. An imposing dark gray tome, Competitive Strategy is a business classic. I remember reading it sometime in high school, and not understanding very much of it. It was only six years later in a college macroeconomics class, my professor helped me understand the value of the Five Forces. For startups entering a period of increased capital cost, the wisdom of Porter's Five Forces is more important to consider now than they have been in the past few years.


The New UI for SaaS - The Question

Quick. Casual. Human. Chat differs from other forms of communication. Because of these three attributes, chat seems to be reemerging as a potentially disruptive user interface for both consumers and business users.


3 Questions for Startups to Answer for Themselves in a Volatile Fundraising Environment

65% of entrepreneurs believe that fundraising in 2016 will be more difficult than in 2015, according to First Round's survey. The volatility in the stock market, the steady erosion of public multiples, and the broad decline of seed, venture and growth investment in Q4 2015 seem to portend a repricing of the startup market. In light of those changing circumstances, entrepreneurs should prepare a few different analyses for 2016.


When Data Confounds Our Intuition

Suppose you’ve been selected to participate in a game show. The game show host asks you to pick one of three doors. Behind one, the grand prize awaits. Behind the other two are goats. You choose Door 1. Then the hosts opens Door 3, revealing a goat. The host prompts you again, “Would you like to select Door 2?” Should you choose it?


The Metric that Matters for Startups in 2016


2015 is the end of an era, the era of startup growth at any cost. In 2016, the question that will immediately follow, "What is your annual growth rate?" will be "What are your unit economics?" This change in investor mentality is catalyzed by the increasing cost of startup capital.


The Downward Pressure of Public Markets on Startup Valuations

How have public SaaS companies fared in the public markets over the past few years? It's been mixed. Over this three year period, 32 of 50 companies are worth more today than they were either at IPO or at their trading price three years ago. Of the remaining 18, 7 of those companies went public in 2015. It was a tough year for SaaS companies to go public.