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  • Writer's pictureMalcolm De Leo

Hey Founder: Are you worried your muscles are strong enough?




When I became a founder I was amazed at how many times I heard the question from other founders, "You're taking the leap, huh?" The first time I heard it I thought it was funny. But after the 10th time in less than two weeks, it was a bit creepy and downright eerie. I thought to myself, what the hell am I doing? Am I crazy? How on god's green Earth could I start something from scratch like this?


But bookended by every time I heard that, I was also met with some interesting encouragement. Many VCs I talked to were encouraging because they appreciated my years of experience. They loved that I knew my co-founder for over 15 years. My friends and family were especially encouraged because they said I could do it (but that is their job). In general, people admired "taking the leap". I appreciated that because it's scary as shit to do this.


Listen, I don't care who you are. Starting something new whether it's a software company or an air conditioning business requires you to be okay with questioning yourself. If you don't then you have already failed. Why? Anyone showing total confidence in themselves, their idea, and their abilities is lying to you. Either that or they aren't human and you are talking to the first AI BOT founder.


The central question for all founders should be this, "What muscles are strongest, and which ones are weak?" Being willing to bring this level of personal and introspective honesty to your quest to build something new is healthy and necessary. If we don't take regular and repeated inventory of our skills and abilities. to make sure we are clear where we will personally fail then we cannot succeed.


As a founder, it is your job to do many operational tasks. You need to figure out how to build the product, check product-market fit, interact with customers, sell to customers, operate the business and the list goes on. All these "ingredients" are what you need to build your business, but at the center of getting these things done is you and only you. Sure you may have partners, but your job as a founder is to be honest with yourself.


So as a first-time founder what exercises might I recommend to help make those muscles strong?


Thought 1: You are a founder...who cares?


I have been an executive at big companies, I have been an executive at startups and I have both advised and coached founders, the reality is this; who cares that you founded a company, it doesn't make you special. And if you think it does make you special then you are already ignoring which muscles might be weak before you even begin. I have seen many people in love with being CEO, a founder, or an executive. This type of hubris, in my opinion, is useless and vain. Sure there are leaders who "make the tough decisions" or "have the guts to do what it takes" but in reality, great leaders are servant leaders. I am sure many will disagree with what I am saying because the robber barons of business exude a level of confidence, ego, and bravado, but in a changing world where generations collide in new and wonderful ways, being a humble leader seems to be trending upward. So be proud of what you have created, and be thrilled at your desire to take the risk, but leave your ego at the door if you want to challenge yourself to build new muscles that will make you honest and successful.


Thought 2: Know what you suck at...


I have been interviewing people for years in every job I have worked in. Sadly, this process has devolved into a series of formulaic questions destroyed by some idiot in HR science who seems to think that structured interviews give an even and rounded result to hiring. While there is merit in this idea (I do think that structure to hire is quite important), I would argue that there is one simple question that people must answer for you to get to the heart of who they are. Can they honestly tell you what they suck at? The lame way to ask this question is this; what are your opportunity areas? When you ask it this way, you are giving people the ability to say something bullshitty like, "I just am so committed I can't stop working hard to achieve goals". This is a cop-out. By asking people what they suck at, you force them to answer. And when people can tell you this then they are willing to work hard on what they can't do OR they are willing to complement themselves with people who can help them thrive. Why talk about this? Because a founder who knows what they suck at is a founder who is going to find people not like them to ensure they can build a better business that is greater than the sum of its parts. Knowing where your muscles are weakest is a great way to be a servant leader who respects and supports the important people who they need around them to grow the business.


Thought 3: Profile the shit out of yourself


We have all taken tons of different personal assessments, but do you ever use them? Too many times I have seen people take those assessments and use them wrong. They tend to get tested, use their profile as a badge of honor, and more sadly as a weapon for why their profile makes them superior or ideal for whatever job they are doing. Building on Point 2, these profiles are a great way to understand how you need to do a better job of interacting with those around you who are different than you, not the other way around. Founders need to quantify themselves so they can recognize their trouble spots in a variety of situations so they can be prepared, know their demons will strike, and how to work to improve those weak muscles. This only comes from being on a quest to exercise your founder muscles. Profiling is a great way to quickly quantify yourself into bits and pieces so you can do a better job of analyzing your founder's fitness.


Thought 4: Be willing to carry a shovel, but never be too proud to ask for help


At our company, this is our first cultural tenet; Everyone grabs a shovel but isn't too proud to ask for help. My co-founder and I are adamant about this one. Shoveling makes you strong. It shows you are willing to take on any task to get things done. As a founder, showing those around you that you aren't too important for any task that needs doing (even if you suck at it) is a great way to not only set an example but to build up your weaker muscles. And while picking up a shovel is about getting things done, it also doesn't mean anyone must go it alone. Sometimes people willing to do whatever task needs to be done may choose to take something on that isn't what they are best at. In these moments, people also need to be able to seek help from others when they determine others have a bigger shovel who can either dig faster or guide them on how to dig better.


Thought 5: Be a life learner and realize it is a two-way street


Becoming a founder wasn't first and foremost about making a lot of money (of course that would be an awesome outcome) for me, it was about learning new stuff. Having successfully advised, mentored, and supported executives and founders for years, I always knew something was missing. Getting to sit in the captain's chair is way different from helping people who sit in it. As I said, sitting in it...who cares? For me, I became a founder because I wanted to learn about being one. I wanted to see what I could get better at, what demons I could exercise along the way to trying to build a successful business, and most importantly how to widen my purview of the world. Bringing a life-learner lens to being a founder is a great way to build new muscles and even strengthen the strong ones. To be a life learner as a founder, you need to remember that for every person you coach, you get the opportunity to be coached back. This means constantly looking for how those around you can teach you while you are teaching them. Remember this two-way street and you can exponentially accelerate your success as a founder.


Thought 6: Embrace the demons...run into the fire


We all have demons. We all have fears. For me, being a founder was definitely about facing some demons that have held me back for years. When it is your business you can't hide. You can't run. You can only beat the demons or let them make you fail. Choose victory over your demons and you will come out on top. And even, if you don't come out on top you will still have killed some along the way. Demons affect your founder's muscle health. Facing the demons rids you of fear toxins that keep you from getting stronger. Being willing to do this every day and you will see them disappear over time.


My surprising learning as a founder


I am very early in my journey as a founder, but I continue to be surprised each day at how many demons are dying around me. I ran headfirst into the fire by owning the books, HR, and managing the money among other operational tasks that frankly I suck at...big time. I am the last person on Earth who should do these things, but I grabbed a shovel because in a world of little to no resources someone needs to do it. I feel myself getting stronger each day. In fact, as a divergent visionary idea machine, I am shocked how one of my demons is helping me be more operational than I ever thought I could. I continue to see myself behaving in ways I didn't think I had in me. So while I wrote a lot of stuff above...I do eat my dog food. And probably my most proud moment as a founder happened when one of my former colleagues asked me how it was going and how was I managing with all the pressure.


I looked back at them and calmly told them, "Every day I am exercising my muscles but I was surprised that some of my muscles are stronger than I ever realized."


I reflect on this moment often, because it reminds me never to be complacent. Only by exercising can we make our bodies healthy. As a founder, these "emotional exercises" are critical to winning as a leader, as a business, and in the marketplace.

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