Your Startup Board: How to Make it a Game Changer

00:01
Welcome to Startup Success, the podcast for startup founders and investors. Here you’ll find stories of success from others in the trenches as they work to scale some of the fastest growing startups in the world, stories that will help you in your own journey. Startup Success starts now.

Kate 00:18
Welcome to Startup Success today. We have two guests in studio. We have Matt Blumberg, who is currently the CEO of Acrolinx. They solve content challenges of large organizations through their AI powered software. And Matt is also the chairman of bolster, an executive recruiting firm, which has an intelligent sourcing platform behind it. He’s joined by Mahendra RAM Singa, who is the managing director of secure octane investments. They have invested in over 50 leading cybersecurity startups in the United States, and he is also the co-founder of cyber seed, which is a virtual forum for founders and CEOs of cyber security startups. But this isn’t what we’re discussing, because they also joined Brad Feld to write a book titled startup boards, a field guide to building and leading an effective board of directors. This is a widely referenced and sought after book in the industry, because it tackles the importance of the board of directors for a startup, and this is a subject we have never discussed on startup success, why the board of directors is so important, how you can maximize your board and some things you should look at. So I’m excited to speak with our guests today. Well, thank you again for being here. Let’s just start at the top, the purpose of the board of directors for startups. I don’t know who wants to go first.

Matt B 02:01
We can both go on everything. You’ll get different perspectives from the investor and from the operator. So Mahendra, you should kick us off.

Kate 02:08
Yeah, Mahendra, as we mentioned, is the investor, Matt on the operator, but yes, both of your perspectives on just that purpose.

Mahendra 02:16
You know, such a kind person that Matt is. Let me put it this way, a good board is in service of a great entrepreneur, such as Matt is and so that’s the simplest way I can think of the purpose of a board.

Kate 02:31
Wow, that’s really nicely said. Do you think most investors agree with you on that, that it’s the service you can see this is a love best Yes, because I’ve interviewed VCs who feel differently.

Matt B 02:48
But yes, anyway, so let me build on that, and I’ll say, What do I think in service of the board or the entrepreneur? Means? Here are a handful of things that I have gotten out of great investors over the years. The first one, quite frankly, is great investors are are great at challenging you and on stretching you as a leader, and on helping you figure out that you can do things you didn’t think you could do, you know, and just being good strategic thought partners so that you know that encompasses a lot, but that, I think is, is something that the best board members do, or through the best roles that boards play. But I’ll give you a couple other things too, that I’ve come to really appreciate over the years. One is that the board helps you as a CEO by being a forcing function or a backstop. So there are things that you want to push your team on periodically. And sometimes the answer is to why? Is because I said so. And sometimes that can be a little unsatisfying to the team. But when you can say, hey, we committed this to the board at our last meeting that this will be done by March 31 it just helps you. It’s good backstop. So that’s another thing. That’s a good point. You know, great boards are helpful with pattern matching, right? They have, tend to have a wider range, a wider aperture, of companies that they’re engaged with, than you are. They help you see the forest and the trees, like, what’s the big stuff? What’s the little stuff? And, you know, those two are kind of related to my first point about challenging you and making you better and being good strategic advisors. And then I guess the last thing I would say, which is sort of also wrapped up in that same thing, is the best board members are the ones that really the polite way of saying it is drive intellectually honest discussion and debate, and the less polite way of saying it is to call you out on your own bullshit. And all entrepreneurs, 100% of entrepreneurs, whether they’re in founder mode or not in founder mode, have narratives they spin. You’re constantly in sell mode, and sometimes you’re selling yourself on things, not just selling someone else. And a good board will bring it down to earth.

Kate 05:00
Well, I like how you phrase that. I don’t know if the founder, CEO always sees it that way, right, but that’s a really important role. They kind of give you that reality check. And I like how you phrased too, with the strategic thought partner. I’ve never heard it you described that way, but it is a strategic part thought partner.

Matt B 05:18
My current board, a couple of them actually call it a sparring partner, which I sort of, I get what they said, what they mean when they say that, but I sort of prefer a strategic thought partner.

Kate 05:27
Yes, I prefer that as well, but I can see where it can go in that direction, but that means it’s working, right? Yes, if there’s some sparring going on, yeah, that’s right. I like that. So I think you’ve framed the purpose really well. We’re going to go into some details here, but let’s start with the selection of the board, the board members.

Matt B 05:50
Well, let’s, let’s start with a couple definitions. So in if we’re really, if we’re talking about private, venture backed companies and public isn’t all that different. There are three kinds of board members, management, investors and independents. So selection actually hits all three of them. And you know, the first one, I would say, on management, there’s always a temptation, if you have multiple founders, and most companies have multiple founders now to, let’s say, like everyone gets a board seat. My view of that, which is a little bit maybe unorthodox and definitely irritates some people is, don’t do that. Have one like the CEO. The CEO should be on the board. The Board, the reality of the board is, you want to keep it small and like, if this is your kitchen cabinet, if this is the group challenging you, your co founders might or might not challenge you, but it’s not additive to the organization, to give them that a second role, make them observers, give them whatever rights you need to give them as shareholders. And look, when you control the company, you can determine what the board does and what shareholders do, but I would only have one person on the board, which is the CEO. Great when it comes to investors and investor board members, that obviously is negotiated, and it comes with a financing, right? And, you know, a CEO’s objective there is to keep that not to a minimum, but keep it to a reasonable number. So you don’t want to end up in a position when you’re, you know, negotiating your series D, where now you’re adding your fourth VC to the board, like, that’s just not it’s just not healthy. So you want to roll early investors off as newer investors. Come on. But again, that’s negotiated.

Kate 07:25
Okay, so that’s what I wanted to ask. I think some people fail to do that, right?

Matt B 07:30
Well, yes, and ideally you’re putting it in documents, but if not, you should be doing the same thing you’re doing with your co founders, which is, when you start the company, you say to your co founders, hey, no offense, but let’s make decisions together about who to put on the board and not have all of us on the board. And it’s the same thing with investors. When you’re taking your seed round and someone negotiates a board seat, you can say them, I am very excited to have you on the board, but let’s talk now about how long that’s going to make sense, and if you can contract it, contract it, contract it, if not, at least start the

Kate 08:02
conversation early. That’s important to highlight, I think, because I don’t think people do that enough.

Matt B 08:07
I don’t think they do it often at all. No. So before I get to independent directors, I want to I’ve been talking a lot here. Mahendra any…

Mahendra 08:16
Absolutely. I couldn’t agree more. You know what Matt said, Kate is, if there’s a single pattern that I have seen that invest in over 100 companies, is that when it comes time for the round to come together, the founders are so heavily fixated on the financial terms. Yes, that’s this is completely an after site like, Okay, now the money is wired. Who’s going to be on the board at that point? It is really too late to try and get into those conversations, right? And so, in fact, in the first chapter of our book that Matt bradfeld, who was our third co author, who’s not with us today, in this on this call, the first chapter itself, emphasized the importance of pick the people first, the money, the terms are secondary, because, you know, all dollars agree. Let’s face it, right, but the quality of the person that will stand by you, that will, you know, challenge you in an intellectually honest way. As Matt said, those types of people are rare, and how you build your confidence, how you build your trust with them? How do you open up with them? That’s a process that doesn’t happen in a snap overnight, right? Like a relationship building process, right?

Kate 09:27
I think that’s such a good call out, because so many founders are focused on those that money. Let me ask you, as an investor, are you an early stage investor? Are you offended when the founder says and then I want to put some something in place for when it’s time to roll off for the other stages. Does that offend you or, you know, to Matt’s point…

Mahendra 09:48
No. In fact, I feel immense sense of pride, because they have now built the awareness, the conviction, to have the conversation with me. You know what offends me the most? The fact that they don’t have any conversation with me about how I can serve them to me, that tells me that the average entrepreneur has not done enough homework, homework. Or doesn’t care enough about the value I mean, we pride ourselves on quote, unquote, value add. Now there are enough memes these days about VC value add. In fact, there is somebody who actually made one of those funny bracelets, which says, “let me know how it can be helpful.” VCs can wear those bracelets and just wave them at each other. So those are ways where investors are trying to bring their experiences to the table. Now, of course, there’s a fine line. Sometimes it’s gonna become very overbearing quickly. But when entrepreneur does not talk about any of that at all, that becomes somewhat, I should say, disappointing.

Matt B 10:50
Well, I think, you know, look, to be fair, a lot of first time founders, CEOs, like, there’s no like, there’s no school anywhere for how to build a board, how to run a board, other than the book.

Kate 11:01
I was just gonna say, your book. I mean, I think everyone listening, there you go.

Matt B 11:05
But you know, the reality is, there are a lot of entrepreneurs who sort of view boards as a tax or a burden, right? Don’t view them as a strategic asset, and that’s a mistake. They’re missing out.

Kate 11:17
It’s a pain. I hate to say it, but I hear that word a lot like,

Matt B 11:21
I mean, I always, I advise a lot of CEOs. It’s the it’s the eye roll, right?

Kate 11:26
Right. The board meeting, yes.

Matt B 11:28
But so let’s get to the third kind of director, the independent director. So I have something that I write about in the book called My rule of ones, which is basically add independent directors from day 111, founder, per board, as I mentioned before, and then for every one VC, add one independent. Oh, so for my, my money, the best board construction, early stages, three. What the founder, the founder, the VC, first VC and the first independent. Wow, then it goes five. And so that might mean that your first board is founder and two independents, if there’s no money around the table yet, right? You know, then as you grow, you add your second VC, your second independent, your third VC, your third independent, and that way you end up with a board that has very good balance, yeah, you know, VCs Look, they’re all different humans, and they all have different experiences, but there’s a lot in common across their experience set. And we always, I always, like to encourage entrepreneurs to think about their board as a jigsaw puzzle and think about what piece is missing. And you know, when you think about the kinds of discussions you want to have at the board level, again, you’re sort of inner sanctum, your your strategic advisory group. What’s the voice that’s voice that’s missing? Is it the voice of the customer? Is it the voice of a more seasoned CEO, because you’ve never done the job before? Is it the voice of a more seasoned head of product, or head of sales, or head of BD, or a lawyer or head of HR, you can sort of think about where your company needs the most advice based on what you’re doing. You know, do you care about someone who knows your business model or not? Do you care about someone who’s seen your stage of growth or not? And the you know, the most important thing is to add the independent director that you need today, and for the next 12 to 24 months, a lot of CEOs get so fixated on like, Oh, my God, I need a public company CEO on my board. Yeah, Andrew, you’re laughing, right? And it’s like, No, dude, he’s like, your company has 20,000 a month in ARR, you don’t need a public company CEO on your board. And don’t worry, none of them want to be on your board anyway, right? So, like, what do you need? Do you need help finding product market fit? Are you a DTC company in women’s fashion? Great. Why don’t we find you a product manager or, you know, product leader in DTC women’s fashion? Like, let’s help you get product market fit, then we can worry about what you need next. And the key to making that whole thing work is not just using the board effectively and finding those the right people at the right time, but don’t lock them in with a five year vest or a four year vest. Like early stage companies, two year vest is fine. Late stage companies can go three or four for sure.

Kate 14:21
This is such great advice, because I think you’re right. Everyone tries to get that big name right out of the game.

Matt B 14:27
Yes, yes. I mean. And worse than saying I need a public company CEO is I want the trophy, board member, right? I want a celebrity, yes, athlete. I want you know, and like those, people are just not going to be good board members. They don’t know how to be. They don’t know your life. They don’t know how to run a startup for the most part. I mean, that’s great like but there’s one of her you know or kind of right.

Mahendra 14:53
Take a moment here seeing our our third co author, Brad Feld, praises because he. Is in his first part of his career, he was like Matt, a founder and entrepreneur, okay, and then through a series of angel investments, and then sort of professional venture capital funds that he raised and managed through, found Foundry Group he took on board seats, okay, other nuances of a board member to Matt’s point, when you look at the independent you could find an entrepreneur who has built a company in some adjacent space, or who may be, I would say, two steps further ahead of you. You’re at seed stage. This founder may have been in Series C or D or little further ahead. They can relate to you very well. They understand the pains of an entrepreneur. The empathy level is very high. And the most important part is they can solve some very crisp problems.

Kate 15:44
For you, I like that. I like how you both framed it around what you need, you know, over the next 12-24, months, and the holes that you can fill, you know, and you gave some really great examples that I don’t think people think of another founder in the space or, you know, an executive who’s would use your product, you know, when you need help with product market fit, or if you’ve got business development challenges, someone with that experience, I’ve never heard it quite phrased that way. It’s always been in Silicon Valley, get the name, get the name. That’s great. I like that. So I think everyone listening should take note of that advice, and then let’s move into the meetings, because that’s an area that, like I said, most founders think of as a pain point.

Matt B 16:27
Most founders think of it as a pain point. And most CEOs run crappy board meetings.

Mahendra 16:34
Except Matt, of course.

Matt B 16:37
I mean, like, there are plenty of CEOs that run good board meetings, but there’s some stuff that you you have to work on really hard to run a good board meeting. One of them, quite frankly, is just a skill, which is meeting facilitation. Not every CEO or founder has like you actually have to have to run a meeting, right? But, you know, there are a lot of things that I can talk about around around having a great board meeting, but maybe Mahendra, you and I can sort of go back and forth on this. So I don’t just talk, talk, talk. I tell you, there are two things that happen before a board meeting that are really important to do in order to have a good board meeting. The first one, well, the second one is to have a great board book, and I’ll talk about that next. But the first one is to make it easy on yourself to produce a great board book. So this gets back to the eye roll and the fact that founders view boards as a tax number of founders I talked to that are like, Oh, I got a board meeting. It’s going to take me and my team a whole week to get ready for it. Yes, that means you’re doing it wrong. No. So okay, you know my so you have to put a little bit of effort into process, but the name of the game is, produce the content once, use it lots of times.

Kate 17:46
I see where you’re going with this.

Matt B 17:50
Yeah, that you should only be producing content for the board that’s useful to you that you need, right? You shouldn’t be doing specials for the board because, like, this person asked for this analysis. That person, I mean, if they’re asking for that analysis, either it’s useful for you, in which case you should do it, or just ask them why they want it and try to, you know, ask the five whys, and sort of get to get to something. But I always have this kind of operating cadence of you get close to the end of the quarter, exact off site. Let’s do a retro in the last quarter. Let’s do our plan for the next quarter. Let’s talk about what we want to use. To use the board for in the upcoming board meeting. And let’s do a QBR like, let’s pull all the materials together. Great. Now when it’s time to do the board book, everything is there, so you do have to do some work to version it and make sure that board consumable, which I get to in a second. But like, make it easy on yourself. And then the other sort of pre game thing is having a great board book. And having a great board book, besides making it easy on yourself to prepare, involves a few things. One is make it easy to consume. So have a little empathy for your board members, and think about how crappy the experience is. I feel like I’m using that word a lot today. Sorry, no, think about how bad the experience is as a board member to get an email with nine attachments. Next, think about how difficult it is for a board member who sees you four times a year to read a book loaded with acronyms and inside text, right, that they don’t understand what it is. Next, think about how hard it is to read a board book that’s 150 pages long. Board books don’t have to be exhaustive, but they do have to be easy to read. And I actually, I have given myself a challenge, which is I try to make board books as short as possible so that it gives the board members the things they need to know, and it lays out really clearly the issues that are on my mind that I want to talk about at the board meeting. And then the last thing about board books is you’ve got to get them to people ahead of time. And ahead of time means, I believe, a minimum of a weekend plus a business day. So most board meetings are not on Mondays. That’s when VCs do their internal meetings. So Tuesday, and no one likes to do Fridays. So Tuesday, Wednesday, Thursday, our board meeting days, get your book out the Friday before and give people enough time to read it. And bonus, if you use a platform like the one I’ve become obsessed with, is a platform called Zach Okay, and Zach dot app, and it has great interactive features. So my last board book, I had like 75 comment threads going back and forth before the meeting. Oh, that’s great. So we got out a lot of stuff before we even sat down together.

Kate 20:31
Wow, that must make it so productive.

Matt B 20:35
So anyway, those are my thoughts on pre, pre meeting. So let me bounce it to Mahindra, and then we can talk about the meeting itself.

Mahendra 20:40
No, absolutely. Matt, I think the part that you touched on in terms of preparation, in terms of helping yourself to align. I mean, to me, the simplest objective of a board meeting can be split into two separate parts. One is, pause and reflect on what has happened. The second is, now let’s look into the front the next quarter, the next whatever phase, month, year. And now let’s start from this point on, how can we achieve our targets? That’s if I distill it down, those are two things that we try to accomplish. And the more we communicate with intellectual honesty, the more we give ourselves enough data and also the benefit of positive intent, as opposed to doubt. We conduct ourselves as A class team, right? And that’s where I feel like the culture and systems that Matt touched upon, if you have the culture of what we call as the open book or transparency or there is nothing here to hide, there’s no politics, everything is up form assessment by anybody you know. The example that I can quote is this entrepreneur, Doug Song. He built this company, Duo Security that got acquired by Cisco for over $2 billion. His board books were a Google a set of Google Docs that every employee, no matter what level they were hired, they would, one of the first things they would do is read those books. So just go and read this rule that they’re sent to our board, the highest authority in the pecking order of the financial spectrum. This is what we are sharing with them. You have to get up to speed with everything that we’re doing, the challenges the company is facing. I, as a CEO, the metrics, cash flow, blah, blah, everything. And guess what? It turned out to be one of the culturally most powerful companies, one of the most frugally operated companies. It consumed less than $20 million and was a unicorn, sold for two, $2.2 billion.

Kate 22:31
What a great example.

Matt B 22:32
Yeah, I’m a huge fan of publishing the board book internally. Absolutely, sometimes you have to redact a thing or two from it. Usually you don’t, and it’s just so it’s such a great sign of trust between the management team and the company. And, you know, look, companies like ours hire smart people. What do smart people thrive on information? How do smart people make their best decisions when they know what’s going on.

Kate 22:53
And that’s how you get the engagement when you bring the team in on that. Super helpful, great advice. So the actual meeting.

Matt B 23:02
For the actual meeting, if we want to come to the actual meeting, I’ve got three tips for the actual meeting. One of them kind of makes normal sense, and two of them are weird. So we’ll start with the normal one. The normal one is, spend as much time as you can on the future and as little time as you can on the past. So again, this sort of generic, typical board meeting, which is each executive stands up and goes through their slides to say how awesome they were last quarter – that is a nightmare for everybody. Like, it’s literally, it just serves no purpose. And, you know, yeah, you want to send a bunch of stuff in the board book about how last quarter went. And you want to highlight three things that people need to know about last quarter, but you want to spend the time in the meeting with your strategic advisors talking about the future. What are the things that are on your mind? What is keeping you up at night? Where do you need help? Where do you need the benefit of their experience? So 80/20 the book is 80% looking backwards, but the meeting has to be 80% looking forward. So that’s tip one. All right, now we get to the weird ones. Tip two, when you have an in person meeting – I guess this is 2A – when you have an in person meeting, make sure the board members all sit at one end of the table. You have other people in the room, your management teams in the room. You have observers, whatever, put them at the other end of the table, put them in the back bench. Board members should all sit clumped together at one end of the table. So sounds really weird, by the way, it’s a little uncomfortable the first few times you have to move people around. But if you think about it, right, the best conversations that happen are when people feel like they’re in an intimate conversation, right, and they’re looking at each other, and that is really hard to do when you’re at a giant table and they’re like, eight people between you and the next board member, and you gotta lean back and I can’t hear them. Like the other people in the room are important and they can participate, but put that strategic advisory group at one end of the table. Then to be the Zoom version of it is people who are not on the board turn off their video. They turn it on the beginning, they say hi, and then they turn off their video. And then you tell board members to flip the switch in Zoom that says, hide participants not on video. And then when someone on the team needs to answer a question, they turn their video on and they pop up. But the board meeting that has like 16 squares, right, is really hard to have an intimate conversation. The board meeting that has five squares and a bunch of people listening and helping when they can, is a much better conversation.

Kate 25:32
Wow. That’s brilliant advice. As somebody who’s been in these meetings and experienced all the pain points you’re talking about avoiding. Wow!

Matt B 25:39
So here’s quirky tip number three. And I actually think this one may be the most important one. No slides.

Kate 25:46
What? I’m literally preparing slides for a quarterly meeting next week. I love this. Tell us.

Matt B 25:51
No slides in the board room. Yeah, you have to show a visual. Show a visual. You need to do a demo. You do a demo. If there’s a slide, you must point to put the slide up for a few minutes. But again, if your objective is to have a meaningful conversation, what happens when you have a slide on the wall? Where does everyone look? Everyone looks at the slide? Forget about having 100 slides and paging through them. And again, back to the executive dog and pony show that’s kind of nonsense. If you send out your slides ahead of time, people have already read them, what you don’t need to do is have them look at them again and then have the presenter read them, which is what they always do, right? (Yes.) So I abolished slides in the boardroom about 15 years ago, and I had I was never happier, because when there are no slides on the wall, everyone looks at each other, and again, you have really high quality conversations when people, when the board members are sitting together, when they’re looking at each other, and when you’re talking about the strategic issues that matter for the company. And it’s the opposite of most board meetings, which are people are scattered. They’re staring and reading the slides they’ve already read, and then someone’s reading them the slide that they’ve already read, and then all you’re talking about is last quarter like you’re right. You should do an eye roll as the CEO, if that’s what your board meetings are like. But that’s that’s on you. There’s no board member that’s making you do that.

Kate 27:09
Such great advice. I love it. Seriously. I can’t tell you how many those terrible meetings I’ve been a part of. Anything you want to add to the Matt’s comments?

Mahendra 27:21
I’ll take the the perspective of what VCs should do in preparation for meetings. And these are all examples that Matt, Brad and I have quoted in our book. These examples are highlighted in bold boxes because these were such stark examples that we ourselves could not believe it when people were sharing these with us, okay? The first one to be the most appalling one was a board member coming to the meeting without remembering what the company does. Excusable, absolutely inexcusable. That’s like showing up at a dinner table forgetting the name of your child.

Kate 27:59
That is pretty bad.

Mahendra 28:02
So if you cannot remember what the company does, please, please just get off the board. There’s no room for such people here, right? Okay, so this number one. Number two, one of the entrepreneurs defined some of their board members as pigeons, the bird. And so we asked them, like, Okay, what do you mean? Like, what does the pigeon do? They fly in, they make some grunting noises. They eat up all your food, shit all over the place, and fly out. So rule number two: Do not be a pigeon. Do not fly out, fly out, make grunting noises, shit all over the place, eat the food and leave. That’s not what you’re supposed to do. The simplest part, actually, this is not that hard, and this is the reason why there are so many memes, or if you watch HBO Silicon Valley show, you know. It’s not that hard, but it’s not that well practiced in our business, which is why I encourage all my peers to say, in between board meetings, pick up the phone, text, just talk to the CEO for 10 minutes. It could be a Friday afternoon. Find out how he, she, they are doing. Ask them hey the board next board meeting is coming up in three weeks, where can I be of most help to you. Just give me one give me one task. Imagine I’m your executive. Give me one task. Are you looking for a customer, a strategic partner, a key hire? Give me some work to do to help you. That third part somehow is not as well practiced. The first two we do really well. We find what our companies do, and we just come and shit all over the place.

Matt B 29:42
So let me just add one which is really like 1B. So yeah, if you don’t know what company does, go home. So yeah,  but read the board book. And you know not all board members do, and it’s literally the least you can do. (Exactly) Read it, read it thoughtfully, read it with enough time to make notes. I mean, if you open your mouth in a board meeting not having read the board book, there is a 75% chance you’re gonna let everyone know you didn’t read the board book by whatever you ask or you say exactly. And that just makes you look dumb in front of the rest of the board. So just, you know, do your homework. It’s an hour, it’s, it’s part of the job.

Kate 30:26
But it also gets back to what you two started with, for the founders listening, get that board book out in a timely manner. And how you build that board, right? Not with multiple investors and, you know, all these independents that aren’t filling gaps and whatnot. I mean, I can’t believe this, we’re at time, so that’s why I’m bringing us back. But you shared so much, I think, tactical advice around boards that I don’t think many of the listeners have heard. This was incredibly helpful. “Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors” is on Amazon.  So I’m going to encourage everyone listening to get the book, because I’m guessing you have some other tools and advice in there that we didn’t cover today.

Matt B 31:16
Yes, lots. It’s not that long a read, but 30 minutes doesn’t quite do it.

Kate 31:21
And I like today that we’ve got both the investor perspective and the operator perspective. Thank you both for that. You know you played well off each other. I personally learned a ton. So thank you. Thank you both for being here.

Matt B 31:34

Thanks for having us. Kate.

Speaker 1 31:37
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