It’s very difficult question to answer. How do you judge a leader? Is it financial success? The loyalty they engender? Their ability to inspire? There are war-time leaders and peace-time leaders. Leaders may be understated or zealous. I’m not sure we’ll ever be able to say defini … | Continue reading
Imagine you’re a venture investor. You find a great company. You buy 16% of the company for $8m at $50m post-money valuation. Six months later, the company raises $100m at $500m. Things have gone very well.Your 8m has 10xed. Naturally, you ride an imaginary horse around the room, … | Continue reading
There are roughly 27m software developers in the world. Only about 18k of them, or 0.07%, work on crypto or web3 every month.Those 18,000 active engineers have created $2 trillion in market cap across the top 100 projects - $112m of value per person.With such massive potential im … | Continue reading
I’m going to tell you a bit about two startups and I’d like you to guess the name of each company.Both of these businesses are publicly traded. Both startups provide database software to developers to build applications. Both have grown very fast. In fact, their revenue trajector … | Continue reading
I’m going to tell you a bit about two startups and I’d like you to guess the name of each company.Both of these businesses are publicly traded. Both startups provide database software to developers to build applications. Both have grown very fast. In fact, their revenue trajector … | Continue reading
Startups create products. After product-market fit, product teams hew the product roadmap from a panoply of options to the features best aligned with the company’s plans.In much the same way, CEOs architect the organization that builds, markets, sells, and supports the product. W … | Continue reading
Over the last few years, I’ve been lucky to work with founders and management teams to sell about $5b of startups. During that time, I’ve observed a few things about M&A. Here are 10 of my learnings: Most acquirers have built a relationship with the acquisition target. Suitors in … | Continue reading
Suppose you launch a web3 company tomorrow. The business builds software to help other crypto companies grow. Perhaps you’ll sell infrastructure to help other startups scale or software to manage internal operations. After you’ve launched the product, you’ll encounter a new pheno … | Continue reading
How much money flows into crypto each month?There’s the headline figure $1.7T which is the aggregate market cap of crypto. But how about the volumes of US dollars being exchanged into crypto each month? Sometimes this is called fund flows.I’ve learned calculating this figure is t … | Continue reading
The Great Resignation has rippled across headlines and boardrooms as employees' values and priorities evolve. Has the Great Resignation been caused by a silent stagnation in compensation?Let’s compare data from 2010 and 2021 to understand the longitudinal trends in cash and equit … | Continue reading
In the last few weeks, public software company multiples have halved. As have cryptocoins. Solana and Etherum followed Snowflake and Elastic downwards. So much for the Santa Claus rally. Both declines seem to have been catalyzed by the Fed’s intention to hike the Fed Funds rate t … | Continue reading
There’s a simple secret to hiring quickly and building a strong team. Invest in great managers early.Let’s compare the organizational chart of two different startups. On the left, the startup is flat. There is a single leader, with a handful of individual contributors. On the rig … | Continue reading
How does crypto work at the highest level? This is the mental model I’ve been using.There are six key categories of players.Asset acquirers - these include brokerages, custodial and non-custodial wallets, banks, asset managers, hedge funds, market makers, and lenders. They aim to … | Continue reading
If you’re part of a management team, repeating yourself is a key to success.When I worked in online advertising, we measured the performance of marketing campaigns in a particular way called aided and unaided recall.Imagine I send you a survey with two questions: List the names o … | Continue reading
The New Zealand All Blacks are the most successful athletic team perhaps of all time. A rugby outfit whose name originates from the solid black uniforms, they have won 79% of their international matches spanning 68 years. James Kerr followed the All Blacks, interviewed them and d … | Continue reading
It’s very difficult question to answer. How do you judge a leader? Is it financial success? The loyalty they engender? Their ability to inspire? There are war-time leaders and peace-time leaders. Leaders may be understated or zealous. I’m not sure we’ll ever be able to say defini … | Continue reading
GitLab is the first fully remote software company to go public. More than 2000 employees work all over the world and have collaborated to build a massive software business.GitLab provides a suite of DevOps tools that enable engineering teams to build and deploy software, and then … | Continue reading
Are we more productive at the office or at home? Researchers from the University of Chicago published data on the productivity trends across 150,000 employees of a large IT services company to answer that question. It’s the first time I’ve seen analysis on the same business throu … | Continue reading
Are we more productive at the office or at home? Researchers from the University of Chicago published data on the productivity trends across 150,000 employees of a large IT services company to answer that question. It’s the first time I’ve seen analysis on the same business throu … | Continue reading
Over the last ten years, the 75th percentile post-money valuation of a cloud software or infrastructure company has grown 11% annually. In 2021, the post-money valuation has spiked 60% from $48.1m to $77.0m. While not as hyperbolic an inflation rate as copper or lumber, the price … | Continue reading
I’ve playing with a new mental model for early-stage startups: a pendulum. This pendulum oscillates between the limiting factors of the business at different stages. There are only two limiting factors in this mental model: product and go to market.At the moment a startup is foun … | Continue reading
Recently, Jim Benton joined us for Redpoint Office Hours to share insights from his vantage point as CEO of Chorus.ai on how sales has changed during the COVID era.Jim shared many data points that opened up my eyes to some of the challenges and the opportunities before modern sal … | Continue reading
About a year ago, I wrote a post on the hub and spoke data model. The idea is that in the future SaaS applications would be built on a single database, instead of each SaaS application writing to its own proprietary database.I was wrong about the catalyst for this hub-and-spoke m … | Continue reading
So you’re looking to start a company. What do you call it? Once you’ve figured that out, which domain suffix do you choose? .com, .net, .biz, .monster, .duck, .theworldisyouroyster? Given the explosion in domain suffix permutations I wondered if startups' behavior had changed ove … | Continue reading
From time to time, I chart the fastest growing categories of startup investment in the US for seed through Series C. Here are 2015, 2017, This year, I was certain the categories would have been influenced by COVID19.I analyzed Crunchbase data and looked for the startup categories … | Continue reading
Every year, I make a list of predictions and score last year’s predictions. 2020 is a year that defines the long tail events, twelve months in which black swan after black swan event seemed to hit the press. Each morning I held my breath as I checked the news wondering what headl … | Continue reading
I remember sitting in the second floor of the engineering building late into the night in front of an SGI Indigo workstation during grad school. The machine was a deep purple, and the keyboard was gray, and the screen showed a terminal with a little blinking green box. I spent ma … | Continue reading
“It’s the Finals. It’s hard. It’s supposed to be hard.” After Game 2 of the NBA Finals said them to Steph Curry as they walked through the tunnel to the locker room after a loss.What’s true for basketball is also true for startups - at least in this case.With all the news of unic … | Continue reading
With the analytics tools today, it’s easy to measure hundreds if not thousands of different metrics for your business. Cutting through all the chaff to determine the most important or insightful metrics can be quite a challenge. Below are the ten metrics I’ve found to be most use … | Continue reading
I’ve been steadily progressing through the excellent books in the Stripe Press catalog. First, I read High Growth Handbook. Most recently, I read An Elegant Puzzle: Systems of Engineering Management by Will Larson. It’s the best book I’ve read on engineering management.Will has w … | Continue reading
How do you tell if your sales team and marketing team are working well together? There’s a simple diagnostic that I’ve come to use. Compare the slopes of marketing’s lead generation efforts to sales’ bookings trajectory.The marketing pipeline trend should be the pipeline for this … | Continue reading
Asana filed their S-1 this week. Asana builds productivity and task management solutions. When they launched, their vision of eliminating email through task management made big waves in the market. Today, the company is a massively successful SaaS business and another example of … | Continue reading
Constrained by a limited budget while seeking to grow as quickly as possible, startup founders must decide how to balance growing their engineering teams with their sales & marketing teams. To help inform those decisions, I’ve benchmarked the relative sizes of the sales and engin … | Continue reading
In this era, virtual events have replaced IRL events. Virtual events have many obvious benefits. No hotels, no event venues, no catering, no ensuring guests are in the right city at the right time. But there are unanticipated benefits that are only now coming to light.Many of our … | Continue reading
In this era, virtual events have replaced IRL events. Virtual events have many obvious benefits. No hotels, no event venues, no catering, no ensuring guests are in the right city at the right time. But there are unanticipated benefits that are only now coming to light.Many of our … | Continue reading