Post Series A Life: Reflecting on Our First Board Meeting and What It’s Like Working with Brad

On Christmas Eve we officially welcomed Brad Feld to the team at Mattermark, as part of leading our Series A round for Foundry Group he has joined me on our Board of Directors. For now it’s just the two of us and I am starting to think through what I want from our 3rd independent board member — someone we will mutually agree upon, hopefully by the end of Q1.

About where the Series A begins, is where I’ve noticed a lot of the transparency end for early stage companies. Startup founders who felt comfortable sharing before might get a bit more static from their investors, and I thought maybe this would be the case for me, too. Fortunately, Brad’s of a similar mind to me when it comes to being open… so I thought I’d write a quick note about how things are going so far — about 8 weeks after announcing the round.

Closing the Round

We announced our round in December, but it was just this past week that the final wire transfer hit our bank account. With so many investors, managing communications and giving everyone the opportunity to exercise their pro rata rights (because I believe in getting returns for my angel investors) was pretty time consuming. Foundry took $5M of the round, and our existing investors took the rest. I love our investors, and we wouldn’t have survived without them, but founders who are considering raising a “party round” from many small investors should be aware that chasing down yes/no decisions and very small checks (in many cases < $5k) is in your future if you are fortunate enough to raise an equity round later.

So that’s done. Or as I Slacked Brad “DONE! DONE! DONE!”

Slack

We’re already quite busy working together, and adding Brad to the company Slack is the coolest thing on the list so far. I have a 24/7 asynchronous direct connection, and Brad can also chime in on any of our 40+ chat channels.

A lot things I need Brad’s help with are small things, an introduction here, quick feedback on a decision that would normally make it to the board deck but really shouldn’t need to wait that long, sharing little wins, stats, and trading ideas back and forth as they come up. He’s also in Boulder and we’re in San Francisco, so I try to send pictures of cool things that happen at the office or even videos of key meetings to release new features or announcements.

The Board Meeting

We had our first board meeting last week in Boulder, and I brought my cofounders with me and prepped as best I could. Brad has a book called “Startup Boards” which I am ashamed to admit I only fully finished on the plane ride out. Ahead of time I had written a very rough outline of what I wanted to cover, and the book gave me a lot more guidance. Skip straight to the Appendix if you are crunched for time, and use the board meeting preparation checklist — I wish I had found this sooner!

There was no deck, just an outline and links to several supporting Google Docs that we maintain on an ongoing basis to operate the company. We had set aside 6 hours for the first meeting because I wanted to bring Brad fully up to speed on the company over the past 3 years, we weren’t pitching now — we were partners and it was time to stop selling and instead lay out the challenges, vision, goals, and plans for strategic discussion and feedback.

Ah!

I won’t lie, I was pretty stressed about this beforehand. I felt like I should have prepared more, but ultimately I just told Brad, “I’m going to run this meeting like it was my ideal board meeting… and you can tell me what I missed”.

What’s ideal to me:

• I can’t deal with being bored for very long
• I don’t want to get too stuck on the details
• I want to front-load any administrative or other decisions (options grants, budget approval, etc.) to the beginning of the meeting
• I want to have a meaningful conversation about the most important strategic items, ideally 30–45 minutes for 2 or 3 key things
• I’m not going to prepare slides, we can use the spreadsheets and graphs the company uses to manage every day.
• No surprises.

Supporting Documents

Having been a solo board member for nearly 3 years, I didn’t know if there would be some mysterious ritual to board meetings that was dramatically different than how I’d been leading, planning and communicating until now.

At Mattermark, and at Referly before that, we’ve worked hard to refine a planning process designed to be just structured enough to make sure everyone knows what they are working on… but flexible enough to handle the ever-changing nature of a startup as we learn new things. We used to plan in 1 week long sprints, then 2 weeks, then a month… now we plan for a full year but break it out by quarters at the strategic level, and month-long sprints with 4–6 key deliverables at the execution level.

Here are some working documents I find super helpful:

• Spending Budget & Revenue Projection (we assume a reasonable MRR growth rate of 8%, set a maximum monthly burn rate of $400K)
• Hiring & Compensation plan (including stock options budget)
• Company Strategy Deck (why are we here? what is the mission?)
• Product Roadmap Deck (what are we building to achieve the mission?)
• Technology Plan & Schedule (how to deliver the roadmap)
• Detailed Customer Acquisition Metrics (CAC, LTV, MRR, ACV, etc. — we use Baremetrics for this now, I used to track all of it by hand)
• Org Chart (Zenefits has a nice dynamic one)

Nothing here was made from scratch for this board meeting, we were already using these core living documents to organize and guide our thinking before we ever began raising our Series A. They are shared broadly internally, and help us track the way our thinking changes as we learn more about the business.

Even if you don’t have a board yet, you might consider creating these if you feel like communication of your mission and plan could be crisper. Some might say, “Ewwwww this sounds a lot like a business plan” and I guess you could call it that, but for me it’s been a huge help as a framework for decision-making, prioritization and keeping the senior leadership team on the same page.

Running the Board Meeting

The most important things I took away from Brad’s book are that I needed to run the meeting, but also make sure to draw from everyone in the room. My job was to create a good structure for conversation and then let it happen, and keep things moving if they lagged.

Being considerate of things like food preferences (thank you to Brad’s assistant Mary for taking care of this!), setting ground rules (we were fine with laptops and phones out… but I’m not sure if everyone would be) and generally creating a good environment is important.

My cofounder Andy took the meeting notes, simply annotating the Google Docs outline we had started with as we went. This also gave us a living document to review after the meeting, and continue to comment on. I still have plenty of action items left to complete coming out of this quarter’s meeting, and I threw all of them into an Asana list as I re-read our notes later that evening.

Just Hanging Out

I’m pretty sure my favorite part of our board meetings will always be hanging out afterward, when the formal part is done and we can just enjoy some great food and drinks and a broad ranging conversation about technology, politics, books, whatever. Boulder is awesome for this, and we’ve already started getting to know many of our Foundry Group cousins.

I’ve had a few founders ask me, “how are you going to to go about getting to know your new investor?”

Building new relationships as adults is harder, it’s like we don’t have the muscle memory from doing it each new school year when we were kids. I’m no expert either, but I’ve noticed a direct connection between spending time talking about things someone cares about and building trust and understanding. So that’s my plan, to spend time talking with Brad about things he cares about and sharing things I care about. Like running a marathon, it’s pretty simple if you just put one foot in front of the other. So the key is to keep doing that, and keep investing, beyond the early excitement of having him on the team or “honeymoon period”.

The Overall Vibe

My cofounders and I see Brad like a late cofounder, and less like an investor (whatever that is supposed to mean). He’s sitting at the table, offering ideas and connections and constructive wisdom to make us better every day. To be clear, we’re not perfect. Creating this startup will continue to be a messy non-linear process for some time to come, but I’m happy to have added someone to the team who doesn’t need me to put on “The Show”.

The rest of the company is still figuring out how to react and some people are engaging more on Slack and Twitter than others. I’m looking forward to taking the senior leadership team with me for our next board meeting in Boulder in April, and generally finding more opportunities for Brad to work with our functional groups on different things. He has a lot of product and data feedback, which is awesome. This sometimes comes in floods that can be overwhelming to some people — so we’ve encouraged the team to view him as a customer with access to some internal email addresses. We file his bugs and prioritize his feature requests along with everything else, and are careful to avoid any “because Brad says” or “because The Board says” reasoning for what we decide to do or not do.

That’s it, my experience having a Series A investor and running a board meeting for the first time. Tweet to me at @DanielleMorrill with your thoughts, and let me know what has worked well for you managing relationships with your new investors and building a startup board.