Surviving a Startup: Best Practices from Chris Stewart, CEO of Raise the Money

by Innovate Arkansas April 28, 2020 Clients, Resources

We asked Chris Stewart to tell us about his experience building and launching Raise the Money and some of the key learnings from his years as a startup founder.

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When I started my company, Raise the Money, I had no idea what I was doing! I was an attorney with my own legal practice and had two young kids at home. I didn’t have an MBA. I had never even heard of a cap table. I just started buying books and tried to figure it all out. It was an incredibly stressful time — running my law practice, building Raise the Money on the side, and maintaining relationships at home while spending quality time with my family. Ultimately, the pressure was enough to drive me to find a way to manage it all in a more healthy way spiritually, mentally, and physically. Through my efforts to find this balance, I developed a practice called TRAIN that serves as a checklist to follow to prevent stress and overwhelm. TRAIN stands for Transparency, Rest, Active, Intentional, and “No.” 


Transparency means finding someone you can talk to openly and honestly. It is important to share what you are going through to get it off your chest and to get feedback and advice. For me, the CEO Forum has been a great outlet for transparency. We are a group of startup founders who have similar issues and can share confidentially with each other. As a founder, there are things that you are struggling with that you keep to yourself and you feel like you don’t have control of, but with this group, you can be open up about those struggles and hear from those who have faced similar challenges. 


Downtime is important for your body and mind to recover from the rigors of running a business. Jesus, for example, would be found alone on a mountain to rest after the big things, good and bad, that happened in his life. Whether you relax with a book or through journaling, or by going fly fishing or with meditation, taking time for rest is imperative to overall health. I personally read a lot. Last year I read 26 books and I like to vary the genres from fiction to business, and history to self-improvement, many times reading several books at once. I also spend time journaling every single day in an effort to write out all the things I need to do and have a plan to execute against. I have found that if I write it down, I will do it.  


If you are a startup entrepreneur, then you are not risk-averse! I fall squarely into the “risk-taker” category and I needed to find something physical as an outlet for my energy as the company started gaining traction. I landed on mountaineering as a strenuous hobby that could take my mind off of the business, but still give me the thrill of the risk. John Muir has said, “Keep close to nature’s heart...and break clear away, once in a while, and climb a mountain or spend a week in the woods. Wash your Spirit clean.” When it comes to climbing mountains, you could die if you do it wrong. I knew that I would have to train hard and focus. It gave me something other than my business to work towards every day and an outlet to survive. You have to get away from your business occasionally.


Family, friends, and employees are important, but take time and energy that you don’t always have to give when you are starting a business from the ground up. A founder must be intentional about taking time to themselves. You need time by yourself and you need to not feel any guilt about taking the time that you need. I have been known to check into a hotel room for a weekend just to have that time. I now leave my office by 4 PM every day and go to the gym to have daily time to myself. It has been invaluable to my mind, body, and spirit. 


This category is all about saying “no” to some things. You must recognize that you can’t do it all and that you are not obligated to say yes to everything asked of you. Stop over-committing and be judicious in the things you do say “yes” to going forward.

As a result of this TRAIN practice, I have found that nothing ruffles my feathers or intimidates me anymore. I am able to keep my mind clear and focused on the things that matter when I am taking care of myself. 

Copyright © 2020 by Chris Stewart. All Rights Reserved.

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