I recently went one on one with Matt Blumberg. Matt is the co-founder and CEO of Bolster and author of Startup CEO and Startup CXO. Matt also founded Return Path, which he helped grow to $100M in revenues and a successful exit.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth?

Matt:  I’ve generally had a really happy and fortunate life with a number of positive role models and experiences that have driven my growth. Out of all those experiences, I can point to two poignant stories that stick with me to this day. One was my first semester at college. I went to Princeton and I was feeling pretty good about myself for getting into a top school...until I got there and realized that I was thoroughly average. I got a C on the first paper I ever turned in, despite thinking I was a great writer.  When I went to my professor’s office hours for feedback he reminded me of the following, “Everyone here was #1 or #2 in their high school class, this paper is nothing special, and I think you can do better. Sometimes, Matt, you just need a 2x4 between the eyes.”  And you know what?  He was right. I could do better. At every step in my professional journey, I’ve tried to be really intentional about “leveling up” and not pretending that what got me to that level was going to work to get me to the next one.  

The second experience I can share was running my first marathon. I am not a particularly athletic person. I played some youth and high school sports but I wasn’t that good at anything. In my 20s, I discovered running and got in shape and set out a goal of training and completing a marathon. I ran and trained almost every day for the better part of a year and even there I wasn’t sure I could complete the race. It was really “grind it out” kind of training - 5-10-15 mile runs in the freezing cold of a New York City winter.  Even after I completed my first 20 mile run, I looked at my roommate and training partner Karl and said “there is absolutely no way I can run for another hour right now.”  But I knew when I started the actual race that I’d be able to finish it, and the moment I crossed the finish line, I was pretty sure I could do anything in the world that I really set my mind to.

Adam: What do you hope readers take away from your new book? What are the key lessons?

Matt:  Startup CXO is really a book of books and is not necessarily designed to be read front to back, although it certainly works that way.  It’s a how-to manual for people who lead executive functions at startups including CFO, CT, CRO, CMO, and more. There are a ton of takeaways in the weeds about how to execute different leadership jobs in a startup.  

The key lesson for CEOs is you don’t have to know everything about an executive’s job on your team to be an effective manager and leader—and you certainly don’t have to be able to do that person’s job. You just have to know enough about what they’re supposed to be doing to help them stay focused on both strategy and execution, and to ensure that they are continuing to develop in some of the underlying functional competencies for their role.  

The key lesson for CXOs is that you not only have to master the entirety of your role in order to excel at it, but you also have to deeply understand your “neighbor function” roles as well, since you are on top of all the connection points and perspectives.  So if you run Sales, you’d better understand Marketing and Customer Success and Business Development pretty thoroughly.  If you’re in Marketing, you need a tight grip on what Sales is doing, but also Product. 

The key lesson for aspiring CXOs is that “your” section of the book gives you a career development roadmap.  If you really want to run your department over time, don’t just be great at the job you have today.  Learn and ideally do some of the adjacent jobs within the same department to round yourself out.

Adam: In your experience, what are the key steps to growing and scaling your business?

Matt:  These three things will hold you in good stead no matter what kind of business you run.

First, always listen to your customers. Ask them what’s working about your product. Ask them what’s not working. Ask them what other vendors they work with and what else they’d like to buy from you if only you offered it. Spend a half day with them and observe what they do and think about how you could make their lives better.  

Second, be intentional about who you have inside your organization, and treat those people really, really well. Hire slow. Take the time to get a new hire right by widening the funnel and interviewing thoroughly, even if you urgently need the position filled. Then, grow your talent.  Every dollar you invest in training your people, in creating a more engaging culture, or in high quality management and leadership is a dollar that returns a multiple in terms of longer high performing tenure.  Finally, fire fast. If someone isn’t working out, whether it’s for performance reasons or cultural reasons, whether it’s a new hire or a long-tenured person who no longer meets your needs and isn’t coachable or transferable into another role that’s a better fit, it doesn’t do anyone any good to keep a problematic employee around.

Third, invest in yourself.  It doesn’t do your organization any good if you’re tired, run down, burned out, or stagnant.  Come up with an Operating System that works for you to keep you at the top of your game at all times, including taking as much time off every year as you possibly can. A high-wattage leader will create a high-wattage organization.

Adam: What do you believe are the defining qualities of an effective leader?

Matt:  Effective leaders must be authentic. They must be themselves.  They must speak in plain English, even if they are working off a script.  They must be able to work off a script at all times. They must bring their whole selves to work - even if that means sharing tidbits from their personal lives or being vulnerable around their team members.  

Effective leaders must also be really good at something important - better than anyone else in the organization.  That could be a functional competency like finance or marketing. They could be the fastest person at reading and processing information, or the best writer or speaker. Or even something small, like they could be the best at remembering people’s names and faces.  

Effective leaders must lead by example.  I’ve worked for bosses who were absolutely dreadful on this front, and it poisoned the entire organization. If you have a frugal culture and talk about the value of every penny, don’t go out and spend a huge amount of money on your own T&E.  If you value humility, don’t brag to people about how much money you make.  If you want to inspire people to work hard, you need to work hard first, and probably harder than anyone.

Adam: How can leaders and aspiring leaders take their leadership skills to the next level?

Matt:  Every leader needs a coach and a mentor. Sometimes those two roles come in the same person, but more often than not, they don’t. The world’s greatest athletes, the ones who get paid zillions of dollars because they are the best in the world at something, use multiple coaches daily to perfect their craft and keep them focused.  Why should Rafael Nadal or Serena Williams have a trainer and a coach, but not a business leader?

Mentorship almost certainly requires someone to have done the job you’re doing, preferably multiple times, or for a long period of time, or through multiple stages of company growth, or two or three of those qualifiers.  This is the kind of person who can literally teach you how to do your job.  These people are super busy, they won’t have open ended amounts of time for you, but you should expect sage wisdom and answers when you need them.  And you can have more than one of them at a time, or change them out as your company evolves and your needs change.

Coaching is different and is a profession in and of itself.  Great coaches might have had a significant career in business before becoming a coach. They probably have some kind of academic grounding, like a Master’s degree in Organizational Development or Industrial Psychology, or a Certificate in Coaching. This is the kind of person who can do things for you and your team like facilitate meetings, run assessments like Myers-Briggs or DISC, and coach other leaders on your team.  This person is dedicated to helping you be the best leader and professional that you can be and must be both empathetic and comfortable pushing you hard.

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?

Matt:  Develop a strong vision that you can clearly communicate to others. Then recognize that even if you’re tired of hearing your vision, everyone else around you - all your team members, customers, and other stakeholders - need to hear it regularly, and you need to be just as enthusiastic about sharing it the fifth time in a day as the first.

Get your hands dirty.  No one loves a leader who barks commands out from the corner office, or on email or Slack, and then lets others do all the work.  This is more obvious when you’re in a small organization, but it applies universally.  Even the President of the United States writes his own speeches once in a while or goes out into the field to talk to citizens directly and collect primary data instead of only relying on staffers and pollsters.  

Master the art of feedback, whether facilitating business retrospectives or working on your own performance management or development plan.  My four-step feedback process is simple:  (1) ask for feedback, (2) accept feedback gracefully - no arms crossed, no denials, debates or excuses, at most some clarifying questions, (3) act on the feedback you receive, and (4) ask again to see how you did.

Adam: What is your best advice on building, leading and managing teams?

Matt:  There’s a team development framework that most people use, and most people get wrong, which is the notion that a team follows a fixed path of developmental stages called Forming, Storming, Norming, and Performing.  There’s nothing wrong with the framework, but what most leaders don’t realize is that every time you add or subtract a member from the team, it’s a new team.  If you swap out one person on the team, you may not have to spend a long time back at Forming or Storming, but even the highest performing team has to take the time out when it gets a new member to run through those phases again and then spend some time back in Norming before resuming your Performing status. Every change to a team brings a loss of capabilities or a gain in capabilities that changes the equilibrium of the team or personal relationships in material ways. 

Adam: What are your best tips on the topics of sales, marketing and branding?

Matt:  The best marketing books I ever read are the Trout & Ries books - the one simply called Positioning is my favorite. It will really push you to think differently about your value proposition and competitive differentiation. Most memorably, the book correctly points out that consumers have slots in their mind for categories and then a runged ladder of brands on each ladder. So choose your slot carefully, especially if you’re creating a new slot, and have a clear understanding of which rung you occupy, why, and what you can do to step up a bit. 

When it comes to selling, I always try to tell stories and ask questions and ultimately to get the customer to do the selling for me.  Start with your product, then back up to the needs it fulfills, then tell empathetic stories and ask pointed questions to get prospects to identify those needs themselves.  It’s not just “leading a horse to water so they can take a drink,” it’s “getting the horse to walk straight to the trough.”

Adam: What is the single best piece of advice you have ever received?

Matt:  It’s about always being in listen and learn mode.  My Grandpa Bill always used to ask a lot of questions of other people and spend a lot of time paying attention to their answers.  When I asked him once why he was so quiet in some conversation, he replied, “I know what I have to say...what I don’t know is what the other guy has to say.”


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

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