Jul 21, 2022

Get Inside The Mind of a Scaling CEO


Adapted from a post originally published on StartupCEO.com, July 14, 2022. 

Serial entrepreneur and CEO of Bolster Matt Blumberg, wrote the book on being a Startup CEO - and I don’t mean figuratively.

He wrote a summary about his experience of being a multi-time founder in this post where he talks about the value of things like a hand-picked team, hand-picked cap table, experience that drives efficient execution, and starting with a clean slate. The second lap around the track (and third, and fourth) is really different from the first lap.

Based on what Bolster does (helping companies scale CEOs, Executive Teams, and Boards), and his current role as Founder and CEO, Matt spends a lot of time meeting with top CEOs from companies of all different shapes, sizes, and sectors.  

Lately, he’s noticed a distinct set of behaviors and desires among CEOs who have founded multiple companies that is different from those same things in first-time founders. 

Not every multi-time founder has every single one of these traits, but they do have a majority of them and form a common pattern. He’s noticed this with both non-profit founders and leaders as well as for-profit ones.

  • They have an Easier Time Recruiting team members and investors. 

This may sound obvious, but there is inherent risk to joining an early stage company and having a CEO that can recruit the right talent and investors to buy into the vision is mission critical for a successful startup.

  • They also tend to have Much Cleaner Cap Tables.

This is because they lived the horrors of a messy cap table when they exited their last company without thinking about that topic ahead of time!

  • They have a Big Vision

Once you’ve had an exit, whether successful or not (or somewhere in between), you don’t want to focus on something niche. You want to go all-in on a big problem.

  • They are interested in creating Portfolio Effect. 

A number of repeat founders want to start multiple businesses at the same time, are actually doing it, or are creating some kind of studio model that creates multiple businesses. Once you have a big team, a track record with investors, and a field of deep expertise, it’s interesting to think about creating multiple related paths (and hedges) to success.

  • They are driving to be Efficient in Execution and Find Leverage wherever they can

"One multi-time founder I talked to a few weeks ago was bragging to me about how few people he has in his finance team," Matt says. "At Bolster, our objective is to build a big business on a small team, looking for opportunities to use our own network of fractional and project-based team members wherever possible."

  • They are Impatient for Progress

While being mindful that good software takes time to build no matter how many engineers you hire, repeat founders tend to have fleshed out their vision a couple layers deep and are always eager to be 6 months ahead of where they are in terms of execution, which leads me to the next point, that…

  • They are equally Impatient for Success (or Failure)

More than just wanting to be 6 months ahead of where they are in seeing their vision come to life, they want to get to “an answer” as soon as possible. No one likes wasting time, but when you’re on your second or third company, you value your time differently. As a friend of Matt’s says in a sales context, “The best answer you can get from a prospect is ‘yes’ – the second best answer you can get is a fast ‘no’.” The same logic applies to success in your nth startup. Succeed or Fail – you want to find out fast.

  • They are Calm and Comfortable in Their Own Skin

At this stage in the game, repeat founders are more relaxed. They know their strengths and weaknesses and have no problem bringing in people to shore those things up. They know that if things don’t work out with this one, there’s more to life.

  • They are stronger at Self Management. 

They are more efficient. They exercise more. They sleep more. They spend more time with family and friends. They work fewer hours.

Anyone else ever notice these characteristics, or others, in repeat founders? 

These traits alone don't guarantee success, but the experience repeat founders carry with them is valuable. They can be steadier, more aware of existing challenges and how to overcome them, or more driven to accomplish their continued purpose. First time founders have their own unique fire—but if you’re working with someone who brings experience (or if you’re taking another “lap around the track”), watch for these encouraging signs.  

Interested in learning more?
Join to receive Venture Capital research, guides, models, career tips, and many other great insights delivered straight to your inbox.

Interested in the full research paper?

Click here to sign up below for free access to the full research library report.
Download the Full Research Report!