Lessons Learned as a Multi-Time CEO with Scott Petry

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This is a podcast episode titled, Lessons Learned as a Multi-Time CEO with Scott Petry. The summary for this episode is: <p>Today on The Daily Bolster, Matt welcomes Scott Petry, and they discuss what it’s like to be a multi-time CEO. Scott talks about how his first experience as CEO differed from his second time around, and he shares what was easier, along with the lessons he learned and carried forward in his career.&nbsp;</p>
🥊 Market pull versus pushing to the customer
02:05 MIN
⌚️ Live in the now
01:00 MIN
🧘 Bring a zen approach to tough situations
01:30 MIN
🤔 Take time to understand how employees engage with the company differently
01:23 MIN

Speaker 1: 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 my good friend Scott Petry. Scott is a multiple time CEO. He was CEO and founder of Postini in the email security space. Worked at Google for a while now, and I think executive chairman?

Scott Petry: That's correct. Formerly CEO. Now executive chairman.

Matt Blumberg: Of Authenticate also in the security space. Scott served on the Return Path Board as an independent director for seven, eight, nine years and is overall one of my favorite humans. Scott, the thing that I wanted to talk to you about today is, like me, you're a multi- time CEO. And the question is your second time, second lap around the track, what was different, what was easier.

Scott Petry: Before I dive in, Matt, you're one of my favorites too, and I feel like I'm smarter every time I leave a conversation with you. So thanks for having me and great to be with you again. Before I say what's been easier, I just want to lay in a bit of context. It's something that should have been obvious to me the first go round, but it was a lesson that was learned later in the development of this company, and that's basically the difference between a market pull versus the need to continually push to the customer. In Postini, we were there at the dawn of the email security space. There were other security vendors that were doing things that might be tangentially focused on email, but email was never a primary focus. And our trajectory sort of coincided with the rapid acceleration of email as a primary communications medium in business. And we struggled for a while selling against the traditional vendors. And then there was a tipping point where the volume of malicious or threatening email outpaced the growth of regular email and it put companies in a position where they had to do something about the problem and the traditional vendors weren't able to keep up. Now, the forces that drove that transition were totally outside of our control, but having been in the execution mode and being really proud of what we were doing, it was easy to fall into the trap of believing that it was based completely on our execution.

Matt Blumberg: Of your own brilliance.

Scott Petry: Of our own brilliance. And you take that thing that we as entrepreneurs, were all raised with, build a better mouse trap in the world will beat a path to your door. It was the second time around that I learned that that's a fallacious statement. It's really not true. The idea of being bought versus selling in an engagement with the customer is really, it's a nuanced point, but I think it's a profound point.

Matt Blumberg: Yeah, it sure is. All right, so what's easier second time around?

Scott Petry: So at this time, I feel like I have a better understanding and appreciation for the time needed for things to develop. It's not a lack of urgency, but Postini was, as we said, an eight year overnight success. There was a lot of sort of buildup to it, but that last four years or so clouds your memory of the prior four years. And so this time around, I feel like there's been a closer understanding on my part that there's a process to iterate, to try different product approaches, a time needed for the market to catch up as you experiment and try different things. And it requires you to basically be cognizant of that sort of trial and error process to find what sticks. You never make it on the first shot.

Matt Blumberg: I'm living that right now. So that totally resonates.

Scott Petry: It seems obvious, right?

Matt Blumberg: Yeah, yeah. All right, so patience is number one. What's number two?

Scott Petry: Patience. Okay. Yeah, you're always more succinct than I am. Context around macro and micro changes. And I could revert back to the sort of buy versus be bought or sell versus be bought thing. But I think in this one, we had a pretty major competitor that was acquired by Microsoft about two thirds of the way through our history of our company. And at the point of the acquisition when it was announced, it felt like an existential issue for our company. A lot of churn, a lot of turmoil felt like, well, what did we do wrong? What should we have done better is our life over, et cetera. But the macro changes slowly and our market did not disappear for us. In fact, having a big vendor buy one of your competitors helped legitimize the market that we were helping create, and it gave us a proof point of the need for other companies to do what we were offering. And so I have a newfound appreciation that there are going to be things outside of my control, but I need to contextualize them and adapt to them rather than feel like, oh, shit. Shows over.

Matt Blumberg: Yeah. All right. So how can we characterize that? Better absorption of the world around you.

Scott Petry: What is it? The zen, right?

Matt Blumberg: Yeah. Well, and look, it's related to your first point, right?

Scott Petry: It is.

Matt Blumberg: It's a more calm approach. So what's number three?

Scott Petry: A deeper understanding that each employee engages with the company for different reasons. In the first company, it was the post- 2000 era, it was hustlebustle. com, euphoria, and I assumed that all of the employees were in it with the same sort of founder's mentality that I had. We pushed through and the company grew, et cetera. But I think with personal maturity and with that, I mean raising the family and understanding a broader set of life pressures, as well as more empirical data about employees working at the company engaging in different ways, I understand now that there are external priorities that people have that can have an impact on their level of emotional investment or engagement that employees have with signing up for our mission. And I think it's important to, I think you probably said it to me once, you never want to have a team with all Michael Jordans on it. It's really come true to me that you want to build a portfolio of people that are all competent in their job and they're all doing their job, but their motivations or their priorities might not all be centered around the same corporate initiative or the same level of urgency.

Matt Blumberg: That's so true. And you have to meet them where they are.

Scott Petry: Yeah, absolutely. Absolutely. Yeah.

Matt Blumberg: Great, great advice. Great talking to you Scott. Thank you for being here.

Scott Petry: Matt, great to be with you as usual. Thank you.


Today on The Daily Bolster, Matt welcomes Scott Petry, and they discuss what it’s like to be a multi-time CEO. Scott talks about how his first experience as CEO differed from his second time around, and he shares what was easier, along with the lessons he learned and carried forward in his career.