Thread by @ryan_caldbeck

1/ My goal here is to share some difficult experiences I’ve had with boards. Not because I have the answers- there may not have been any.

2/ I share because I would feel less alone going through these experiences had I been able to read more about the unsolvable, difficult experiences from others. I will also share how I felt about the experiences below.

3/ Story 1: I remember my first board meeting at CircleUp. I had been an investor, sat on a bunch of boards, and felt like the board meeting would be smooth sailing.

4/ I remember where I was sitting, 5 offices and 7 years ago, when one of our investors said “Ryan this growth isn’t close to good enough.”

That - just that- reduced me to about 3 inches tall. He was 100% right in retrospect.

5/ I probably needed the clarity of that comment. It didn’t change that I felt small. I also felt a bit lost because it didn’t come with a “so what.” It was my job to develop that- but in the moment I still also felt lost and embarrassed

6/ Story 2: We had a former board member that said “one of my investments took out a full page ad in the [Major publication] to take on [Public Competitor X]. You guys should do that in the WSJ and take on KKR.”

7/ It was a distracting and irrelevant comment. He had no logic for why it would be good to poke the KKR bear. KKR isn’t competitive with us in any way. IMO the entrepreneurs we serve wouldn’t care at all about any made up spat we had with another investor.

8/ I remember feeling exhausted and lonely. Exhausted because we were working so hard and our “partner” (this board member) clearly didn’t understand our business. Lonely for the same reason.

9/ Story 3: I was struggling with something and another board member said “I’m not your friend Ryan.” It came across as so cold and needlessly cruel. I didn’t ever tell that person how I felt. I think that made it feel even worse.

10/ In retrospect I felt lonely, offended, hurt, and angry. I’m an adult. I get that we’re not here for rainbows and sunshine. But that comment really hurt.

I also never had a 1:1 conversation with that person again. The person lost a lot of influence with me in that moment.

11/ Story 4: Important strategic decision. Board member X disagrees with Y, but won’t just say it in the meeting. Wants to only say it to the CEO 1:1 after the mtg for fear of upsetting another investor he might have to source a deal from in the future.

12/ It's not only a waste of time, it robs the CEO of the opportunity to have a real strategic discussion. I believe that friction often makes those conversations more productive- and pushes a conversation forward. I want that friction in the room. Friction makes fire.

13/ Last time this happened I remember feeling so frustrated. I said to X “please just say this in the meeting.” He wouldn’t. His refusal also made me feel confused and wonder if he is more committed to that relationship than our Company.

14/ Story 5: Board member stops meeting and says in a loud and angry voice “we’re not focused on the right thing. This company has less than 6 months of burn left.”

15/ We had >24 months. He was doing the math wrong. But it wasn’t funny- it was amazingly representative of my frustrations about a board member that would just detract value.

16/ Honestly on that I felt blah. He had already demonstrated such a lack of understanding of the Company that I wasn’t surprised. Perhaps I felt a little validated as well.

17/ Story 6: Board member says “you guys have never worked with a good consumer company” 5x in a 10 minute stretch. Emotion #1 was defensiveness. At that point we had worked with Halo Top and several others of the most successful consumer brands of the past 10 years.

18/ I knew he was wrong intellectually. But I felt so upset I could hardly breath. I stopped the board meeting for 10 minutes to gather my thoughts-only time I’ve ever done that.

19/ It hurt so much - **so much** - to hear what felt like such a needlessly personal and unproductive criticism. Again, I didn’t ever tell him how I really felt - how personal it felt, how inadequate I felt. Maybe I will next time.

[We removed him from the board.]

20/ Story 7: Board members that are frequently checking phones and can’t just have the mental discipline to leave their phone in their bags.

21/ When that happens- and it has happened far more times than I would like to admit, I feel irrationally offended. I feel disrespected. I feel worried that other team members will worry the board doesn’t care about us.

22/ Story 8: Had a board member at a board dinner the night before mtg complain we weren’t going into enough detail on a certain topic. He rarely read materials in advance and this time didn’t even take the time to look if the topic was being covered.

23/ At dinner I pulled up a @DocSend report to show him that not only was the topic covered in depth but that he hadn’t bothered to get past pg3 of the deck to see what was in there. I decided to do it in front of the entire board to hopefully encourage him to have better hygiene

24/ I felt so frustrated that we put so much work in to try and make the meeting productive, and he just couldn’t be bothered to read up in advance. I wanted to be met halfway. It felt like we weren’t met at all. I candidly also felt proud that we were prepared.

25/ Story 9: Board member [same former member] gets backdoor reference call on us from great candidate that already agreed to join us. Not sure what he says but candidate backs out an hour later.

26/ We call candidate and hear that board member suggested an idea of working with his VC firm instead of us. I didn’t know what to do. There wasn’t a playbook. I felt lost and helpless and just furious. I felt betrayed.

27/ Story 10: Board member with no UI/UX (or candidly product) experience gives detailed notes on our product in board mtg. How do I tell someone simultaneously “we want you to lean in” and “don’t opine on things where you don’t have experience when we have a bigger agenda”?

28/ I like that board member wanted to lean in on us. I didn’t like that he wouldn’t move on or let us stay on track w/ our agenda, or that he assumed he knew what target user wanted w/o asking. It ended up distracting the meeting a lot.

29/ Being a board member is a hard job. I’ve made some of the mistakes above as a board member of several companies (and I’m sure I’ve made many more mistakes than those listed here).

30/ I just wanted to talk about some of my experiences -and resulting feelings- in case it helped other founders. An added bonus is if it helps board members know how some of their actions land with a founder/CEO.