Last week, I blogged a podcast riff I did about the biggest mistakes early stage founders make and what to do about them. Here’s a summary of part 2 of what I said about later stage founders. Misreading Product/Market Fit or a lack of Product/Market Fit. Misread it high, and founders end up dumping money into sales and marketing too soon. Misread it too low, and you can fire a good sales or marketing team when it’s not their fault! On the high side, Product/Market Fit isn’t just coming from a healthy CAC/LTV ratio or by good early adoption. Early adoption can come from a small group of Visionaries (here I’m channeling Geoffrey Moore’s Technology Adoption Lifecycle curve from Crossing…
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Startup CEO
Top 3 Mistakes Early Stage Founders Make
I just did a podcast recording the other day for someone who asked me the biggest mistakes founders make and what to do about them. I divided my response into “early stage” and “later stage” founders. Here’s a summary of what I said about early stage founders. They cling to a “good enough person” or someone who is a good performer but a weak cultural fit because they either feel beholden to that person for their output, or worse, they’re actually afraid of losing them because they’ll miss a milestone or maybe trigger some other departure. The “what to do” of course is to have courage and make the change! I wrote an essay years ago in Brad Feld and…
Offsites in the age of COVID
I attended two offsites in the last two weeks – both great in terms of seeing people in person. Interesting how differently they handled COVID protocols, although they were different groups with different vibes. One was a CEO conference for one of my VC’s portfolios. There was a huge emphasis in all the pre-conference comms about COVID. And lots of testing. We all got mailed a very sophisticated in-house PCR test ahead of time to take and photograph/upload, complete with chemical reagents and some kind of centrifuge. Then those of us who flew in for the event had to do an on-site rapid test before entering the opening reception and even had a side room to sit in for 15…
I’m Having a Blast at Bolster — Here’s Why
Someone asked me the other day how things are going at Bolster, the new company I started along with a bunch of long-time colleagues from Return Path last year. My visceral answer was “I’m having a blast!” I thought about it more after and came up with five reasons why. First, I am working with a hand-picked group of people. My co-founders, I’ve worked with for an average of 15 years – we know and trust each other tremendously. And for the most part, the same is true about our cap table. Almost everyone else at the company is also someone multiple of us have known or worked with for years. That may not last forever, but it makes things…
Startup CXO: the Sequel to Startup CEO
As I finished up my work on the Second Edition of Startup CEO: A Field Guide to Scaling Up Your Business and started working on a new startup, my colleagues and I started envisioning a new book as a sequel or companion to Startup CEO that is going to be published on June 9 with our same publisher, Wiley & Sons. The book is called Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams. Simply put, the first book left me with the nagging feeling that it wasn’t enough to only help CEOs excel, because starting and scaling a business is a collective effort. What about the other critical leadership functions that are needed to…
The Tension That Will Come With the Future of Work
The Tension That Will Come With the Future of Work A lot has been written about the Work From Anywhere life that knowledge workers are leading right now due to the pandemic, and what will come next. Fred has a great post on it, and I’m curious to see how his and Joanne’s “Home Office Away From Home” space called FrameWork does when it opens. In that post, he references a few other posts and articles worth reading: Imagine Your Flexible Office Work Future – Anne Helen Petersen We’re Never Going Back – Packy McCormick The Future of Offices When Workers Have Choice – Dror Poleg Instead of entering the debate about what the future will look like, which no…
Soliciting Feedback on Your Own Performance as CEO
(Excerpted from Chapter 12 of Startup CEO) As a CEO, one of the most important things you can do is solicit feedback about your own performance. Of course, this will work only if you’re ready to receive that feedback! What does that mean? It means you need to be really, really good at doing four things: Asking for feedback Accepting feedback gracefully Acting on feedback Asking for follow‐up feedback on the same topic to see how you did In some respects, asking for it is the easy part, although it may be unnatural. You’re the boss, right? Why do you need feedback? The reality is that all of us can always benefit from feedback. That’s particularly true if you’re a…
Second Verse, Same as the First…Except Way Better
Almost a year into my second journey as a startup CEO at Bolster, and I’m getting more and more questions from other CEOs about what it’s like doing a second startup after almost 20 years at the first one…and achieving pretty good scale by the end. The short answer is, it’s the same, only it’s way better. Here’s why. I’m more confident. So is our whole founding team. When Jack and I started Return Path, we were 29. This time, we were 49 — and the average age of the founders was probably 46 or 47. The bottom line is that we don’t know everything about the business we’re building, but we know what we’re doing in terms of building…
StartupCEO.com: A New Name for OnlyOnce
Welcome to the new StartupCEO.com! I started writing this blog in May of 2004 with an objective of writing about the experience of being a first-time entrepreneur — a startup CEO — inspired by a blog post written by my friend, long-time Board member and mentor Fred Wilson entitled “You’re only a first time CEO once.” The blog and the receptivity I got along the way from fellow startup CEOs encouraged me to write a book called Startup CEO: A Field Guide to Scaling Up Your Business, which was originally published in 2013 and then again as a second edition last year in 2020. Today I am relaunching the blog as StartupCEO.com both to reflect that relevance of that brand…
Startup CEO Second Edition Teaser: Thinking about Your Next Step
As part of the new section on Exits in the Second Edition of the book (order here), there’s a final chapter around you as CEO and thinking about what you do next. I’ll start this post by saying, while am really happy with where I am now (more to come on that!), I am not happy with the way I handled my own “next steps” after the Return Path exit. I did follow some of my own advice, but not enough of it. I jumped back into the fray way too quickly. Some exits leave CEOs in a position of never having to work again – those are good in that they give you more time to think about what’s…
Startup CEO Second Edition Teaser: Transition and Integration
As part of the new section on Exits in the Second Edition of the book (order here), there’s a specific chapter around handling the post-sale transition and integration process. No two transitions are exactly the same. If the buyer is a financial sponsor, you may have the same job the day after the deal closes that you had the day before, just with a new owner and new rules for you. Sometimes you’ll stay on with a strategic buyer as the head of a division, or the head of your product. Sometimes you leave on Day 1. Sometimes you leave later. But the most important thing you can do is remember that once the deal is over, it’s over. That’s…