Managing Effective Boards as a CEO with Mahendra Ramsinghani

INTRODUCTION: Welcome to the Daily Bolster. Each day we welcome transformational executives to share their real- world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with Mahendra Ramsinghani. Mahendra is a seed- stage investor. His firm is called Secure Octane. He is the author of a book called The Business of Venture Capital, which is a great book that explains how VC firms work. Every founder should understand that. He is the author of a new book that I have not read, but I'm very excited about reading, called The Resilient Founder, and he is also a co- author along with me and Brad Feld of Startup Boards. Mahendra, excited to have you here today.

Mahendra Ramsinghani: Thank you for this opportunity, Matt. Thank you.

Matt Blumberg: Yeah, so it feels like you and I must talk about boards in some way or another based on our joint project and startup boards. And you've sat on a huge number of boards far more than I have, and I would love to just hear from you what your top three tips are for CEOs in how to manage effective boards.

Mahendra Ramsinghani: Thank you, Matt. First of all, thank you for the opportunity and both you and I are passionate about helping founders achieve their highest potential, whether that's financial, whether that's intellectual, and as we worked on startup boards, it was a realization that you brought the founder's perspective to the table. Brad and I, as co- authors, always had the investor perspective, and very grateful that you infused the book with new energy and new life. The top three areas where I feel like founders and boards could work well together are, number one, we're human beings. This is something that we often lose as we kind of get into posturing, get into titles or CAP tables and blah, blah, blah. We forget the fact that there is behind all of this, there is a human being. As Brad correctly said at the NBCA event, we're all humans with emotions and desires and fears and aspirations. So we have to always keep reminding that there's a human being across the table. Okay? The second is that I often find the relationship is not always treated as that of equals. We're two wheels of the same cart. An entrepreneurial energy combined with financial capital yields societal progress. But many times there's either subservience, there are power plays. Investors also are equally responsible or guilty of this. So founders and investors need to work together to say, " This is not a game of thrones. This is a team of equals. We have agreed to solve some problems jointly, and you bring your resources, I'll bring mine. We'll have some fun." So, the second part is-

Matt Blumberg: That's such a good point. There are a lot of founders that are afraid of their board. They don't know what to make of a board. And my advice to them is always just think of it as a high performance team.

Mahendra Ramsinghani: Yeah. And you did this very well, Matt. I didn't have the chance to spend time with you, but Brad spoke so highly of you for the period that you had Fred Wilson, you had Brad, you had a board that was clearly high- performing, if not the best in class in the business. And the comfort with which you approach them, the sense of confidence that you have to have done your homework, but you have sense of confidence the way you engage with them. That is an area where I feel like a lot of founders need to work on, which is to say, these are my equals, these are my peers. Now on the flip side, our investors often are guilty of making demands or treating founders as not necessarily as equal. So there's a lot of work to be done on both sides. Rick Hidesman, who's from Firstmark Capital based out of New York, shared a very interesting quote where he said, " And I've had board members tell CEOs, let's model out what happens if, something arbitrary, if an asteroid hits the earth." You can spend six months doing some very arbitrary exercise and it's not going to be productive. So I think it's something that both sides need to work on. And third, and the final sort of aspect of this dynamic is this is a marathon. Brad and I ran a marathon. You worked with Brad for a long period.

Matt Blumberg: Brad and I ran a marathon.

Mahendra Ramsinghani: Oh wow. There you go. So now you've done... You can do separate exercises with your board member where you're constantly redefining what does success look like in the next phase? Success in the first mile looks like, " Let's just get started. Let's make sure we don't stumble and fallen off my face. But at mile 17, gosh, I remember, we would come across these benches along the marathon track, and Brad would jokingly point at the bench and say, " Do you want to sit down?" I'm like, " Brad, let's go for the next bench." So we kept redefining what does success mean at the next mile and the next mile? And this is something that is very important. I just had a conversation with one of my CEOs where he goes around and kind of failed to inform half of his investors who are very mad now. Like, " How did this happen? We didn't get a chance to participate. We weren't even aware." I'm like, " Okay, let's reset. Let's communicate well. Let's redefine success." So it's an ongoing journey where both sides need to learn how to create a safe and environment, create trust, and just work well as team members.

Matt Blumberg: Mahendra, great advice. I would love to be on a board with you someday. Fantastic director.

Mahendra Ramsinghani: Or run a marathon. It'll be fun.

Matt Blumberg: Thanks for joining me here.

Mahendra Ramsinghani: Thank you. Thank you so much.