A fellow CEO with whom I’m friendly was venting to me the other day about one of their Board members. They were stunned that the lived experience they have day in, day out running the business wasn’t something the director internalized at all — and this is a good, well known, high quality VC director. I pointed out that VCs are on lots of boards and can’t get in the headspace of all their CEOs all the time, although the good ones don’t just swoop in and swoop out but do take the time to track all the significant things and the nuances with all their portfolio companies. My friend, the CEO, had a brilliant comeback line that is worth…
Category
Venture Capital
The quest for diversity in Tech leadership is stalling. Here’s why.
There’s been a growing cry for tech companies to add diversity to their leadership teams and boards, and for good reason. Those two groups are the most influential decision making bodies inside companies, and it’s been well documented that diverse teams, however you define diversity — diversity of demographics, thoughts, professional experience, lived experience — make better decisions. Gender, racial, and ethnic representation in executive teams and in board rooms are not new topics. There’s been a steady drumbeat of them over the last decade, punctuated by some big newsworthy moments like the revelations about Harvey Weinstein and the tragic murder of George Floyd. It’s also true that in people-focused organizations, and most tech companies claim to be just that,…
Startup Boards: VCs and CEOs need to do their jobs!
Was anyone else as appalled as I am by the contents of Connie Loizos’s recent article, Coming out of COVID, investors lose their taste for board meetings? The stories and quotes in the article about VCs reducing their interest and participation in Board meetings, not showing up, sending the junior associate to cover, etc. are eye opening and alarming if widespread. The reasons cited in the article are logical—overextended VCs, Zoom fatigue, and newbie directors. Connie’s note that “privately, VCs admit they don’t add a lot of value to boards” is pretty funny to read as a CEO who has heard a ton of VCs talk about how much value they add to boards (although the good ones DO add a…
Introducing Bolster Prime and Bolster Ventures (and their back story)
This is another big week for us at Bolster. On the heels of the announcement we made last month about our Series B financing, we are now announcing the launch of a new program called Bolster Prime and a new venture capital fund called Bolster Ventures. These are important steps in Bolster’s evolution and in the fulfillment of our mission, what we call internally our “Big Idea,” which is to empower the innovation economy. The roots of Bolster Prime and Bolster Ventures pre-date the founding of Bolster. In our prior lives, the Bolster founders worked together to scale up a business called Return Path and also worked as advisors and mentors to numerous early stage founders and startups. One of…
The Blackjack Table
I lived one of my favorite metaphors last week as we announced the closing of Bolster’s Series B financing and had our first post-round Board meeting, and I realized I’ve never blogged about it before: that raising rounds of financing is like having a good night at the blackjack table. When I go to Vegas or AC — and admittedly I haven’t done that in several years — I usually start playing Blackjack at the $5 table. It’s lightweight entertainment, low stakes, good way to warm up and remind myself how to play. If I start winning and accumulating a bigger pile of chips, I move to the $10 table. Rinse and repeat, to the $25 table and the $50…
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…
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…
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…
Breaking New Ground on Transparency
Breaking New Ground on Transparency I’ve written a lot over time about our Live 360 process for senior leaders in the business. (This post is a good one, and it links to a couple earlier ones that are good, as well.) We take a lot of pride in feedback and in transparency at Return Path, and after 15 years, even for an innovative business, it’s unusual that we do something big for the first time around people. But we did today. This image is of something never seen before at our company. It’s my own handwritten notes about my own Live 360. It’s never been seen before, because no one has ever been physically present for his or her own…
Getting the Most out of Your Investors
Getting the Most out of Your Investors Fred Wilson has been a venture investor and director in Return Path since 2000, first with Flatiron Partners and then with Union Square Ventures. We’ve been through a lot of wars together. In a couple of weeks, he and I are team-teaching a class in Entrepreneurship at Princeton, and the professor gave us the assignment of writing two pairs of blog posts to tee up discussion with the class. The first two posts were mine on selecting investors and Fred’s on selecting investments. This is my second one…and Fred’s post on the other side of the topic is here. Once you’ve done a venture financing and the smoke clears, you have to transition…
Selecting Your Investors
Selecting Your Investors Fred Wilson has been a venture investor and director in Return Path since 2000, first with Flatiron Partners and then with Union Square Ventures. We’ve been through a lot of wars together. In a couple of weeks, he and I are team-teaching a class in Entrepreneurship at Princeton, and the professor gave us the assignment of writing two pairs of blog posts to tee up discussion with the class. This is the first one…and Fred’s post on the other side of the topic is here. Next week, we’ll address the topic of building a successful CEO-VC partnership once it’s established. If you’re fortunate enough to have built a really strong early stage company, you will find yourself…