(This post was written by my colleague Bethany Crystal and originally published on the Bolster blog yesterday. While I am still trying to figure out what posts to put on this blog vs. Bolster’s blog since the blogs are pretty similar, I will occasionally run something in both places.) At Bolster, we believe that 2021 will mark the rise of the on-demand economy for executives. More than ever before, executives are seeking out roles that distinctly aren’t full-time for a variety of reasons – they’re in between full-time roles and want to stay engaged and meet a wide range of potential employers; they’re retired or semi-retired/post-exit and want to keep working, just not full-time; they’re fully employed but are looking for advisory opportunities to…
Category
Entrepreneurship
Zoomsites
(Written by both my Bolster co-founder Cathy Hawley and me) I’ve attended two remote conferences, which Cathy dubbed “Zoomsites” — one here at Bolster and the Foundry Group CEO Summit. Both hold interesting lessons for how these kinds of events can work well. We founded Bolster two months into the COVID-19 pandemic, and our founding team had not met in person after 6 months of working together. Now, luckily, we’ve all worked together for many years, so we have a lot of trust built up, and have a very strong operating system which includes full team daily standups. Still, nothing beats face-to-face interaction. If you’ve ever founded a startup, you know how impactful it can be to work side by…
What Job is Your Customer Hiring You to Do?
My friend George, one of our co-founders at Return Path (according to him, the best looking of the three), has a wonderful and simple framing question for thinking about product strategy: what job is your customer hiring you to do? No matter what I’m working on, I am finding George’s wisdom as relevant as ever, maybe even more so since I am still learning the new context. Why is this a useful question to ask? It seems really simple – maybe even too simple to drive strategy, doesn’t it? It’s very easy in technology and content businesses (maybe other spaces too) to get caught up in a landslide of features and topics. In a dynamic world of competition and feature…
OnlyOnce, Part XX
I realize I haven’t posted much lately. As you may know, the title of this blog, OnlyOnce, comes from a blog post written by my friend and board member Fred Wilson from Union Square Ventures entitled You Are Only a First-Time CEO Once, which he wrote back in 2003 or 2004. That inspired me to create a blog for entrepreneurs and leaders. I’ve written close to 1,000 posts over the years, and the book became the impetus for a book that another friend and board member Brad Feld from Foundry Group encouraged me to write and helped me get published called Startup CEO: A Field Guide to Scaling Up Your Business back in 2013. Today is a special day in…
Sometimes a Good Loss is Better than a Bad Win
I just said this to a fellow little league coach, and it’s certainly true for baseball. I’ve coached games with sloppy and/or blowout wins in the past. You take the W and move on, but it’s hard to say “good game” at the end of it and feel like you played a good game. And I’ve coached games where we played our hearts out and made amazing plays on offense and defense…and just came up short by a run. You are sad about the L, but at least you left it all out on the field. Is that statement true in business? What’s an example of a “bad” win? Let’s say you close a piece of business with a new…
Feedback Overload and Confusion – a Guide for Commenting on Employee Surveys
We run a massive employee survey every year or so called The Loop, which is powered by Culture Amp. We are big fans of Culture Amp, as they provide not only a great survey tool but benchmarks of relevant peer companies so our results can be placed in external context as well as internal context. The survey is anonymous and only really rolled up to large employee groups (big teams, departments, offices, etc.), and we take the results very seriously. Every year we run it, we create an Organization Development Plan out of the results that steers a lot of the work of our Leadership team and People team for the coming year. I just read every single comment that…
You Don’t Know How to Drive a Car Because You Know How to Read a Map
I was having breakfast with the CEO of another SaaS company the other day, as I often do to network. He was telling me about his experience working with his company’s new Private Equity owner. There are always a mix of pros and cons that come with any particular shareholder, Board member, or owners, of course. In his case, my fellow CEO was bemoaning the 29-year old associate who acted like a know-it-all in every Board meeting. Lots of CEOs have been there. There’s a lot of value you can get from an associate or VP-level person at an investor who is the Master of the Spreadsheet and who has access to a lot of data about your company. And there is…
No One Will Ever Thank You for Keeping Prices Low
I was in a Board meeting last week (not Return Path’s), when one of my fellow directors came out with this gem: “No one will ever thank us for keeping our prices low.” When I first heard this, as is the case with most great quotes, I was drawn to its wit and simplicity. But then I started thinking – is it true? My mind first went to retail. Having a reputation as being a low-cost provider can be in and of itself effective marketing – if that reputation is strong enough and your selection is wide enough, at least in retail-oriented industries, customers may consistently buy from you even if you’re not ALWAYS the low-cost provider. Wal-Mart and Amazon…
Knowing When to Ask for Help in Your Startup
I had a great networking meeting yesterday along with Tami Forman, the CEO of our non-profit affiliate Path Forward, and Joanne Wilson, my board co-chair. It was a meeting that Joanne set up that the three of us had been talking about for over a year. Joanne made a great comment as we were debriefing in the elevator after the meeting that is the foundation of this post. Tami and I shaped her comment into this metaphor: Finding wood to help start a fire is different from pouring gasoline on a fire As an entrepreneur, you need to constantly be asking for help and networking. Those meetings will shape your business in ways that you can never predict. They’ll shape…
How Venture Capital Firms Work, for Entrepreneurs and Startups
A couple of months ago, I was doing an internal lunch & learn for senior managers, and the topic came up as to “how do our VC firms work?” In the spirit of deeply understanding our customers’ businesses in order to better serve them, I thought the same would be true of our investors and Board members – that educating our team on the inner workings and economics of our investors would lead to greater empathy of one of our other key stakeholders. So with no small amount of help from my long-time investor and director Brad Feld and his colleague Jason Mendelson, whose book Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist I contributed to in a very…
Agile Everywhere, Part II
Over the years, I’ve written a lot about the Agile methodology on this blog. For those of you who are regular readers, you may remember a post I wrote about our Agile Everywhere initiative— where all Return Path teams were tasked with implementing agile practices. A little over a year later, I want to update you on our agile journey–where we are now and how we got there. My colleague Cathy Hawley (our head of People) will write a more detailed series of guest posts for those of you who want to get more details of our transformation process. Before we started our Agile Everywhere initiative, only our product and engineering teams were using agile. The rest of the organization…