Perspectives from a second-time founder
The other day I texted an old friend. His name had come up in conversation, and I wanted him to know I was thinking of him.  His reply came swiftly: “When are you gonna get an iPhone? 🤣” My friend is a gifted communicator. Rather than engage
Like everyone in Silicon Valley, I read Founder Mode with interest this week. I won’t pretend I have much to offer Brian Chesky or Paul Graham on the subject of running companies with thousands of employees. The largest company I’ve run was about 150 employees, a
Having spent my career in the data and machine learning worlds, I’ve watched Snowflake and Databricks pretty closely. On the surface, they seem like symmetrical competitors. Snowflake’s core business is enterprise data warehousing, and they would very much like to expand into the ML workloads that
The biggest surprise first-time founders experience is the total lack of external validation in their day-to-day professional lives. Working a real job with a boss, if you’re doing a good job, comes with a steady stream of “good jobs” and “attaboys”
In 1995, the year of their IPO, Netscape offered the best web browser for Microsoft Windows for the very reasonable price of $49 per license. Not long after that IPO, they peaked at 80% market share, appropriate for a market leader with the best product.  That same year, observing
It’s common for young entrepreneurs to get excited about famous VC firm brands. Before even starting their companies, they’d heard of Sequoia and Benchmark, so they get starry-eyed about bringing those storied firms onboard. Later on, getting beers and attending dinners with other founders, you
Every Saturday I come to the office, open up VSCode, and engage in single combat with our web application’s codebase. The goal: To add a mere few dozen lines of TypeScript without screwing up anything important. To make our users’ lives just slightly better, myself, with my
In one of the Apple histories, Tim Cook is quoted as saying, “Inventory is fundamentally evil.” Inventory is cost. It will eventually have to be written down (i.e. thrown away) when it stops selling and you move onto new SKUs. Reducing inventory also has the benefit of
As your startup scales from the dozens into the hundreds and more, it starts to grow into a real organizational structure. Before this transition, you probably have some notion of “teams” and “managers” but it’s pretty loose. Everyone sits in a room with the
This year, my two cats were diagnosed with cancer in quick succession. Then I learned, quite suddenly, that I only have one year left til I’m 40. It’s enough to put a guy into a reflective mood. Shortly after my first cat passed away (may he
Startups go through three phases. In VC parlance, these phases are “seed,” “venture” and “growth.” The seed stage is the search for product-market fit. During this phase you might raise money in rounds with names like “angel,” “pre-seed,”
My favorite Silicon Valley truism is: The team you build is the company you build. ( Credit to Vinod Khosla .) Very soon after founding, most of the work at the company will be done by people who are not you. You will succeed or fail based on the quality of their
It’s pretty surprising how often I have calls with founders where the real problem seems to be a simmering mistrust between them and their board members. Typically they’re calling because of an inflection point: Should they take an M&A offer ? Should they try to
For years it’s been fashionable for investors to compete on the basis of being “founder friendly.” This is of course a messaging strategy: Investors succeed by returning lots of money to their LPs, and a subset of investors do so by winning deals on the basis
Business success is mostly about timing. In technology, an underlying innovation drives a decade-long wave of business outcomes built on that innovation. The internet became generally available in 1991 and drove a wave of Internet 1.0 outcomes that accelerated until the 2001 crash. The iPhone launched in 2007