Category

Startup CEO

Open All-Hands Meetings

I love stealing/borrowing other people’s good ideas for management and leadership when they’re made public, and I always encourage others to do so from me. I call it “plagiarizing with pride.” So I was intrigued when I saw a new way of doing all-hands meetings published by my friend Daniel Odio (DROdio) on his founder community called FounderCulture. You can see the original post here. We’ve experimented with different formats and cadences for all-hands meetings over the years. They tend to vary with the size of the company and complexity of the material to cover. Larger companies usually fall into the rhythm of doing quarterly all-hands meetings sometime after the end of the quarter, usually around a Board meeting, with…

Book Short: New to the Canon of Great CEO Books

Please go put Decide and Conquer: 44 Decisions that will Make or Break All Leaders by David Siegel on your reading list, or buy it. David’s book is up there on my list with Ben Horowitz’s The Hard Thing About Hard Things. It’s a totally different kind of book than Startup CEO, and in some ways a much better one in that there’s a great through-line or storyline, as David shares his leadership framework in the context of his journey of getting hired to replace founder Scott Heiferman as Meetup’s CEO after its acquisition by WeWork, including some juicy interactions with Adam Neumann, through the trials and tribulations of WeWork as a parent company, through COVID and its impact on…

Signs Your CFO Isn’t Scaling

Post 4 of 4 in the series on Scaling CFOs – other posts are How to Engage with Your CFO, When it is Time to Hire Your First Chief Financial Officer, and What Does “Great” Look Like in a CFO?) While all the functions of a team are needed, perhaps the most critical function to make sure your company is able to scale is the CFO. Cash flow, investments into the business, compensation, budgets—nearly everything that happens in a company flows through the CFO—and it should. So, getting this role right is one of the most important tasks of any startup team. But how do you know if your CFO is up to the task of scaling? For CEOs, one…

What Does “Great” Look Like in a CFO?

Post 3 of 4 in the series on Scaling CFOs – other posts are How to Engage with Your CFO and When it is Time to Hire Your First Chief Financial Officer.)  A lot of startups have a bookkeeper, accountant, or even a spouse of a founder or employee handle the finances when they first start out, and that’s fine. But at some point you’ll want to hire a CFO and if you’re dealing with a lot of chaos it’s easy to think, “well, anybody is better than what we have now.” But I would hold off on that thinking because the CFO, a great one, will do a lot more than just manage the finances, AP, and AR. A…

How to Get Credit for Non-Salary Benefits: The Total Rewards Statement

A couple weeks ago, I blogged about some innovations we’d made in People practices around basic benefits. But that post raised questions for me like “Why do you spend money on things like that when all people care about is their salary? When they get poached by another company, all they think of it the headline number of their base compensation, unless they’re in sales and think about their OTE.” While that is hard to entirely argue against, one thing you can do as you layer in more and more benefits on top of base salary, you can, without too much trouble, produce annual “Total Rewards Statements” for everyone on your team. We did this at Return Path for several…

Open Expense Policy

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…

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…

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…

Top 3 Mistakes Later Stage Founders Make

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…

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…