Brett Maloley – Co-founder and CEO of Ladder

I try to work with an understanding that there are certain variables that I can control and others that I can’t. I do my best to take full ownership over the things I can control.

Brett Maloley has had a decade-long career in the fitness industry, both as an executive and as an entrepreneur, having built two successful equipment distribution and consulting companies, a transcendent non-profit geared to combat childhood obesity ( and most recently serving as the chief executive officer for a publicly traded nutritional supplement distribution company. Brett recently embarked on a new endeavor as co-founder and chief executive officer of Boston-based fit-tech startup Ladder, a mobile platform that connects people with local health and wellness professionals, to engage in digital coaching. Additionally, Brett serves as an advisor to, the world’s largest network of Google Chrome extensions. Brett is a passionate student of the health and wellness industry, having grown up in the space, and is committed to using what the industry has taught him to help create forward-moving change.

Where did the idea for Ladder come from?

The idea for Ladder is the culmination of everything my co-founders and I had done previously… working towards a solution that allows people to find happiness through health and wellness. We have a staunch belief that people need; education, a customized plan or process and a way to be held accountable to that plan… unfortunately, the lion’s share of tools that provide such are not financially feasible for the average consumer.

We dream of a world where everyone has access to the tools they need to craft a happy and purposeful life and we believe Ladder provides that solution.

Furthermore, we believe that the bridge between healthcare and health and wellness needs to be crossed, in order to even further reduce the barriers of entry to consumers. When I previously had the opportunity to speak with Mario and Ideamensch, back in 2012; I spoke openly about the future of “preventive medicine” and the lives that will be saved and the fortunes that will be made in perfecting its delivery mechanism… we believe Ladder does just that. While some of the biggest companies in the world are actively working to acquire data, to potentially bridge that gap, directly between the payers and the consumers; we believe the bridge is better crossed through an intermediary of the commercial health and wellness industry; as a space that services the largest pool of potential users and facilitates direct access to the actual service providers.

What does your typical day look like and how do you make it productive?

It’s in my nature (sometimes proving positive and other times not so much…) to be “all in” on whatever I am working on. For me, right now, that is Ladder and getting the business up and running. I usually get into the office, during the week, at around 7 am and stay until around 7-8pm… and then try to work 10 hours or so, on the weekends. Right now, given that we’re pre-launch, the majority of my time is spent fundraising, working through strategy and/or processes and working with my colleagues to make sure the ship is always moving in the right direction. I do my best to allocate my time to whatever bucket needs it most. I’m a very high-level thinker and at times I have difficulty being as granular as I need to be, at this stage in our company… but it’s something I’m cognizant of and work hard at. To me, our office is my sanctuary; right now we’re pre-product and pre-revenue, so just being here allows me to take solace in the fact that I’m doing whatever I can to drive progress and push the business forward.

How do you bring ideas to life?

To me, it’s all about putting the right team in place… an idea is nothing more than an idea if it isn’t acted upon and I’m smart enough to know that I can’t do it on my own. When I bring new people into any organization, the first step is making sure they’re the right people and to assist me in that process I work with an executive consultant/friend/advisor (Jason Kos) and a company called Culture Index. Once I know that they’re the right person (or at least all the information available to me, tells me that they’re the right person,) I work on establishing mutual expectations and what I’m really asking for is: 1) a positive attitude and 2) an unparalleled work ethic. If they’re the right people and they can commit to those two things, then it’s my job to put them in a position to succeed.

What’s one trend that really excites you?

Platform businesses. Creating value by facilitating exchanges between two or more interdependent groups. The concept certainly isn’t new, but technology has changed the way these types of businesses work and I’m very bullish on the overarching business model and see it as the predominant model of the future. The way people buy products or services and/or consume information has changed and is continuing to change. Platform business models drive true utility to consumers and producers. I’m all in on the platform business that we’re creating.

What is one habit of yours that makes you more productive as an entrepreneur?

I try to work with an understanding that there are certain variables that I can control and others that I can’t. I do my best to take full ownership over the things I can control – one of which is my capacity for work and effort.I challenge myself to outwork everyone, every day. That goes for my team and the people around me as well as the people who I’ve never met before. If I can outwork everyone then I’m putting myself in the best possible position to succeed and effort is something that I can control.

What was the worst job you ever had and what did you learn from it?

My last job was the worst job I’ve ever had. It was my fault… but I put myself in a bad position; a position that I could not possibly work my way out of. I put too much stake in my ability to drive change, rather than realizing that certain changes that I intended to make were literally outside of my control. I was naïve and blinded by pure ambition and I set myself up to fail. l will never do that again.

If you were to start again, what would you do differently?

I would be a better friend and family member. As I alluded to previously… when I’m in, I’m all in. My ambition and drive have blinded me to some of the things in life that are more important and, unfortunately, I’ve lost a lot of great friendships because I haven’t put into them the requisite amount of time needed to allow them to survive. I’d like to say that I’m getting better, but the reality is that I’m not. I still struggle with creating a work-life balance that allows me to sustain relationships, outside of work and I know it is something I will regret, down the road… It’s something I already regret very much.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Ask for help. Most entrepreneurs don’t have the requisite skill set or furthermore the bandwidth to do it on their own (I know I don’t.) Reaching out to people who can help is something I do more and more of and I think entrepreneurs should ask for help early and often; they’ll find that most people worthy of getting advice from are willing to give it.

What is one strategy that has helped you grow your business? Please explain how.

Tough to say at this point, because we are still in our infancy… but pulling from my previous businesses as well as what has worked for Ladder, thus far; I would say that focused collaboration is incredibly important. Having more intellectual capital on certain ideas is tremendously valuable, as long as there is a process in place that creates efficient idea generation. Not all people can valuably contribute to all strategies or concepts; so finding the right people to help with the right things, is incredibly important.

What is one failure you had as an entrepreneur, and how did you overcome it?

At my previous company, I spent close to 2 years (without pay) working on something that I ended up simply walking away from. I won’t say I wasted 2 years of my life because the relationships I made were forged through a true struggle and Ladder came out of that struggle… but in retrospect, I never should have put myself in the position that I did. The first step was truly detaching myself from the previous situation and taking a step back to see how bad of a fit I was for the company (and vice versa,) I owe a great deal of thanks to my close friend (Rory Walsh) for helping me come to that reality. Once I was able to determine that it was time to move on, I simply needed to reinvigorate myself to start over with something new… that was the hard part. I look at entrepreneurship as a profession and for me, my profession was truly tested. It would have been much easier to “get a job,” which is what seemed logical to friends and family and what I was being told that I should do… but I know me and I knew that wouldn’t have made me happy, it’s just not how I’m wired.

What is one business idea that you’re willing to give away to our readers?

I think there is a huge opportunity in creating a way to aggregate the workflow of a mobile service provider. I mentioned previously, how bullish I am on mobile platforms, as we see so many of them popping up and truly thriving; uber, instacart, doordash, postmates, the list goes on… Now, being a mobile service provider is actually a profession and there is a lot of crossover relative to producers working for multiple platforms. I think an entity that can create a more efficient workflow for those service providers, across multiple platforms, can solve a huge problem; for both the platforms and the producers that allow them to thrive.

Rather than somebody who is an UberX driver, an Instacart shopper, and a DoorDash deliver”er” having to simultaneously manage their workflow on each independent platform; an asset that streamlines all of the jobs allowing for a more efficient way to manage multiple engagements across multiple platforms.

What is the best $100 you recently spent? What and why?

So… my girlfriend Nicole and I have a 10-month-old french bulldog, named Penelope and she is obsessed with toy balls. She pushes them into things with her nose and could literally play with them for hours on end. We did run into a problem, however, as she kept pushing them under our couches and it got a point where we were pushing all of the couches to the edges of our living room so that she would have more space to play. We tried buying bigger balls, but she didn’t really like them…Ultimately, we ended up finding a ball that was small enough for her to still like playing with it, but just big enough to not fit under any of our couches. That was DEFINITELY, the best money I’ve spent recently.

What software and web services do you use? What do you love about them?

I really love Slack… it allows my team and me to communicate in a way that is a lot more efficient and makes it happen in a fun environment. I also love Producteev… we spent a lot of time looking at different task management tools and actually tried a couple prior to landing on Producteev. The result has been a product that does exactly what we need it to do and not a heck of a lot more, its an awesome tool for creating accountability and visibility of our team’s ongoing deliverables.

What is the one book that you recommend our community should read and why?

The Icarus Deception has recently taken over Start with Why as my number one most recommended book. It really gives you hope and at least for me, serves as a constant reminder that anything is possible. I’ve probably read it 20 times (when I say read, I actually mean “listened to” as I’m a big audiobook guy,) and constantly go back to it if I’m ever lacking in confidence. Society and the economy are changing and there is now more and more data on what works and what doesn’t, relative to entrepreneurship. It’s almost like my entrepreneur bible, a book that reminds you that it can be done… you just have to go get it.

What people have influenced your thinking and might be of interest to others?

I have “my team” and then the people I look to, outside my immediate sphere of influence. “My team” is my parents (Gregg and Mary Maloley) who really instilled in me that majority of things that have allowed me to get where I am today… not to mention the countless amount of sacrifices that they made for both my sister and me to put us in the best possible position to succeed. In addition to them, one of my mentors (John Donati) and my college baseball coach (Dusty Rhodes.) Outside of my immediate group… On a macro level, I really like what Ben Horowitz has to say and more recently have gotten into what is now my favorite blog, “Musings of the Big Red Car,” by Jeff Minch. I’m thankful to be working with Jeff as a personal coach, now and he’s been incredibly helpful to me. On more of a macro level… anytime I can read about Steve Jobs or Elon Musk, I do. I’m not in the same ballpark as those guys, by any stretch of the imagination, but they inspire me. It’s not necessarily their intellect that I’m drawn to as much as their resilience and literal unwillingness to fail.


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