The Red Badge of Courage: Helping Overachievers to Manage and Process Failure
When I lived in France for five years I was often asked to compare it to Silicon Valley in an attempt to explain why — in the land of Descartes, Fourier, and Laplace, in a country where the nation’s top university (École Polytechnique) is a military engineering school that wraps together MIT and West Point, […]
Whose Company Is It Anyway? Differences between Founders and Hired CEOs.
Over the years I’ve noticed how different CEOs take different degrees of ownership and accountability when it comes to the board of directors. For example, once, after a long debate where the board unanimously approved a budget contingent on reducing proposed R&D spending from $12M to $10M, I overhead the founder/CEO telling the head of […]
Good CEO Habits: Proactively Update Your Board at the End of Every Quarter
I am surprised by how many startup CEOs leave the board hanging at the end of the quarter. As a CEO my rule of thumb was that if a board member ever asked me about the quarter then I’d failed in being sufficiently proactive in communications. In tight quarters I’d send a revised forecast about […]
Avoiding the Ten-Year Stock Option Trap (and Other Stock-Option Considerations)
I’ve increasingly spoken to startup employees who find themselves in a difficult trap. Let’s demonstrate it via an example: Say you joined a startup in September 2009 as an early employee and immediately received a stock-option grant of 400,000 shares with a strike price of $0.10 when you joined. The company, while having experienced some […]
What really is “Go-to-Market”?
The single most bastardized, watered-down term in the business of enterprise tech is “Go-to-Market”. Go-to-Market (GTM) gets bandied about as the cure-all to everything from missing 2 sequential quarters to losing critical deals to a single competitor, to seeing a tepid uptick in demand, to my least favorite – a one-time effort to coordinate activities […]
Stopping Inception Churn: The Prospective Customer Success Review
I think for many sales-aggressive enterprise SaaS startups, a fair amount of churn actually happens at inception. For example, back in 2013, shortly after I joined Host Analytics, I discovered that there were a number of deals that sales had signed with customers that our professional services (PS) team had flat refused to implement. (Huh?) […]
Career Decisions: What To Look For In a Software Startup
So, you’re thinking of taking a job at a startup, but are nervous about the risk, perhaps having trouble telling one from another, and unsure about knowing what’s really important in startup success. In this post, I’ll share what I consider to be a great checklist for CXO and VP-level positions, which we’ll try to […]
Appearance on the Twenty Minute VC: Financing Thoughts, The Private Equity Sales Process, and More
Famed venture capital podcaster and now venture capitalist at StrideVC, Harry Stebbings, released a new episode of the Twenty Minute VC podcast with me as his guest. (iTunes version here.) Harry’s interview was broad-ranging, covering a number of topics including: Financing lessons I’ve learned during prior bubble periods and, perhaps more importantly, bubble bursts. The […]
The Market Leader Play: How to Run It, How to Respond
Business-to-business (B2B) high technology markets are all about the market and only less so about the technology. This is primarily driven by corporate buyer conservatism — corporate buyers hate to make mistakes in purchasing technology and, if you’re going to make one, it’s far better to be in the herd with everyone else, collectively fooled, […]
The Two Dimensions of Startup Performance
When it comes to evaluating a startup’s performance, I think there are two key, orthogonal questions that need to be examined: Is the company delivering growth? Is management in control of your business? Growth is the primary driver of value creation in a software startup. I’m not going to quantify what is good vs. bad […]
