I wrote a post the other day about innovating employee benefits practices, and I realized I’d never documented a couple other ways in which we have always tried to innovate People practices. Here’s one of them: the Open Expense Policy, which I wrote about in the second edition of Startup CEO in a new chapter on Authentic Leadership when talking about the problem of the “Say-Do” gap. Here’s what I wrote: I’ll give you an example that just drove me nuts early in my career here, though there are others in the book. I worked for a company that had an expense policy – one of those old school policies that included things like “you can spend up to $10 on a…
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Bolster
7 Habits of Highly Effective Boards
(This blog post was first published as an article in Entrepreneur Magazine on April 15.) Creating strong boards can help propel a board forward. Weak and ineffective boards hold a company back. As a CEO, one of the most important (yet overlooked) tools in the playbook is building and leading a board of directors. Throughout my 20+ years of entrepreneurship, I’ve led four companies (including Bolster, where I’m a co-founder and CEO today) and served on eight boards. I’ve learned that strong boards can help propel a company forward and I’ve also witnessed how weak and ineffective boards can hold companies back. Mediocre or mismanaged advice, plus lack of accountability, can do long-term damage to a business as well. Drawing from personal experience and anecdotes from…
Innovating People Practices Through Benefits
Sometimes the work we do as CEOs, leaders, management teams is glamorous, and sometimes it’s not. But it all matters. One thing we tried to do at Bolster this past year is to really amp up employee benefits. The war for talent is real. The Great Resignation is real. Sometimes startups like ours have natural advantages in terms of attracting and retaining talent such as being made up of letting people in on the ground floor of something, having small teams so individual impact is easy to see, being mission-driven and full of creativity and purpose, and having equity to give that could be very valuable over time. But sometimes startups like ours have natural disadvantages around recruiting like having…
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…
When it is Time to Hire Your First Chief Financial Officer
(This is the second post in the series…the first one on How to Engage with Your CFO is here.) What comes before a full-fledged CFO? Lots of startups have nothing more than an outsourced bookkeeper or one junior staff accountant. Sometimes a founder or a founder’s spouse even steps in on this front. As startups scale, they are likely to hire a more senior accountant, maybe an AR/AP/Collections staff member, or even a Controller or VP Finance. Depending on the complexity of your business you might be able to hold off on hiring a full-time CFO, but if you have any of these signs then it’s time to start thinking about bringing someone on board. One sign is intuitive, 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…
Why the Startup Sales Function Starts With Whiteboards
(This post was inspired by Startup CXO and was originally published by Techstars on The Line.) In most startups, one of the founders is the first salesperson — often out of necessity as much as passion. But as startups scale they add sales reps or maybe some form of a Sales Manager once there are more than a couple of reps. But how do you know when to bring on a senior sales leader? Too soon and you have a very expensive employee, too late and your sales reps are creating their own processes and approaches. As a CEO there are several telltale signs that you need to hire a CRO, for example: You wake up in the middle of…
Five Misperceptions of the CCO Role
This post was inspired by Startup CXO and was originally published by Techstars on The Line. If you’re new to the Chief Customer Officer role, we’d like to share some advice we wish we had learned earlier in our careers. There are a few common misconceptions about customers and the service organization. If you don’t realize these as misperceptions, you can spend a lot of time dealing with issues that are not real, but perceived. We have identified five of these common misperceptions, although we are sure there are more. Misperception #1: The service organization fully controls churn (customer attrition) In a lot of organizations you’ll see the service organization be measured solely on customer churn. If you really think about…
Startup Boards eBook: How to Succeed in Your First Board Role
In addition to our work on helping CEOs understand board-building best practices, which I posted about last week, I’ve spent the past several months publishing a second series of blog posts to help current and aspiring directors (really, any senior executive!) understand the behind-the-scenes details of private company board service. This second series is also now an eBook and its content will also feature in the upcoming second edition of Startup Boards that I’m collaborating on with Brad Feld and Mahendra Ramsinghani. When Bolster published the findings of our Board Benchmarking study, we revealed that 4 out of 5 seats on private company boards today are held by individuals who are white, and 86% of director seats are held by…