The Start-Up CEO Field Guide - with Matthew Blumberg, Founder and CEO Bolster

**Ray Rike** (0:00)
Hello, I'm Ray Wright, Founder and CEO of BenchMarket, and your host of the Metrics That Measure Up podcast. We talked to a wide variety of the top B2B SaaS and Cloud thought leaders, CEOs, executives, investors, and people just like you, to discuss the metrics and benchmarks they use to make metrics informed and benchmark validated decisions. Now, on to today's show.
Welcome to today's episode of the Metrics That Measure Up podcast. Today, I am joined by Matt Blumberg, the founder and CEO of Bolster, formerly the founder and CEO of Return Path, and bestselling author of amazing books for the SaaS startup ecosystem, including Startup CEO, Startup CXO, and Startup Boards. We'll be covering three primary topics with Matt today. First, the top lessons from being a founder and CEO at the same company for almost 20 years.
Second, we'll be talking about the Startup CEO, the second edition and the evolution. And third, we'll be talking about moving beyond storytelling to execution and then selling your company and the stages in between. So with that, Matt, as a background, would you take a moment to give an overview of your journey to becoming a guest here on the Metrics That Measure Up podcast? Absolutely, Ray.

**Matt Blumberg** (1:28)
So thanks for having me. I'm a multi-time tech founder. The role that I had the longest was CEO and founder of a company called Return Path, which was an enterprise SaaS platform for email marketing, analytics, data and security, which we started in 1999 and we scaled up to over a hundred million in ARR and exited in 2019 A bunch of my teammates and I started a new company in 2020 called Bolster, which we run today. Bolster is using data and technology to disrupt the executive search space. So we have a kind of a hybrid approach to executive search where we have great recruiters, but we also give them immensely powerful AI and data tools to be more effective, more efficient. It lets us price and package searches differently. We help founders find executives to do anything from full-time roles to part-time or project roles to board seats to mentors and coaches.
So not a SaaS business, but a ton of our clients are SaaS clients and we're still very much in the ecosystem.
And along the way, I either authored or co-authored three books, as you mentioned, Ray, Start-Up CEO, Start-Up CXO and Start-Up Boards, which are really designed as kind of field guides or instruction manuals for CEOs and founders about how to scale themselves as leaders, how to scale boards and how to scale management teams. I do a podcast called The Daily Bolster. I have a blog called startupceo.com, and that's me.

**Ray Rike** (2:59)
Well, Matt, you could be the startup Sherpa here for the industry, but I'm going to focus on something that when I first met you, and I was doing all my research of the 150 plus episodes with SaaS founders and CEOs we've done here in a Metrics to Measure Up, you hold a record.
And the record is you're the first founder CEO that spent almost 20 years at the same company, that being Return Path. So I have to ask you, is there some fundamental beliefs, maybe two or three that you have about being a Start-Up CXO that only could be informed by having a company that you ran for 20 years?

**Matt Blumberg** (3:40)
Yeah, that may be a little bit of a dubious distinction. There are certainly others out there. I would put you to Mark Benny off as one. But look, I would say there are a few things. The obvious one is that you have to be prepared for the long run. You're running, as they say, you're running a marathon, you're not running a sprint. That does mean that you have to learn how to pace yourself and pace people around you so you don't get burned out. But there are a couple of other things that I've learned too.
The next one is really closely related to that, which is that if you want an organization that is engaged and vibrant, you have to figure out how to make sure that you stay engaged and vibrant.
And 20 years or quite frankly 10 years or five years is a long time to do that. And for me, the key to that has always been learning and growing and perfecting the craft of being a CEO. As I always say, I had the same business card for 20 years, but I had a few different jobs along the way. Running a zero revenue startup is really different than a $10 million startup, is different than a 50 or $100 million startup. And that sort of passion for learning and keeping myself two steps ahead or half a step ahead was very helpful. And, you know, look, I think leaders can scale themselves and you can help them scale much further than you think or much further than they think. And the same is true of you. But learning and growing, constantly learning and growing is really at the top of the list for that. And if I had a third, I might ask for four on this one. If I had a third one to point to, it would be around employees.