It’s a fact, the life of a solopreneur can be one of isolation & struggle. Both those verbs seem to be an accepted rite of passage rather than a recognized problem worth solving. But what does that solution look like, and how do you keep moving forward in the entrepreneurial mindset to avoid a lonely burnout? With advice from 4 CEO’S, we can gain further insight on how to grow a successful startup.

During Chattanooga’s Startup Week extravaganza, for the first time I saw a glimpse into the solution. As if by fate, I was able to make it across town in record time for the 11AM class hosted by Pass It Down in the very artistic Woople Building at 100 Tremont Street.

Without knowing the history of any of the CEO’s scheduled to pass on well-earned knowledge, I took a chance that there was something special that I could takeaway and apply.

I was not disappointed.

There were about 5 questions asked during the course of the hour, as I took notes on their most insightful advice. In startup mode myself, I was most interested in one question in particular:

How to Grow Your Startup with Advice from 4 CEO’s

  1. Conway. “Make sure all legalities are understood before the contract is signed. Logistics are vital to long term success and can actually cause crippling problems if each section of the contract isn’t properly reviewed to full understanding. Sometimes we can get so excited about a new prospect that has the potential to offer our startup a “big break” that we get romantic about the deal when we should get strategic. Now is not the time to celebrate. When the contract has been thoroughly reviewed and agreed upon by both parties, then you celebrate!”
  2. Debbie Crabtree, Director of the Hamilton County Virtual School. “The relationships you make with customers are one of the most important thing to focus on in business. In my case I went into business with a company that was responsible for 75% of our income during our first 3 years. The relationship didn’t develop like it should have out of fear for needing to address some uncomfortable things that didn’t quite align with my values. I let it go and our relationship suffered for it. I wish I would have been bold enough to address the things I didn’t agree with to uphold my integrity. Trust your gut and address uncomfortable situations with customers, bravely.”
  3. Alex Lavidge, CEO of  Variable Inc.  “Start where you are and build from there using the scientific method. Understand who you are and what you are good at by fully understanding your strengths and weaknesses. In short, become self-aware. Knowing where to start can avoid failure. Perspective is important. We can’t be experts at all things so “get paid to learn” from those who you need to hire to fill the gaps because understanding strengths/weaknesses lets you know what gaps to fill.”
  4. James Cowan, CEO of Docity. “Cut the romance cord. A frothy unicorn mentality around startups is nice, but should be a secondary motivator to selling. Create something that may not be exactly perfect but has the ability to bring in money.”


Another vital topic that was discussed was on the importance of taking care of yourself. Tough to stick it out through the long term if you don’t have physical, emotional or mental strength to carry on. This is what the 4 CEO’s had to say about the importance of self-preservation in the midst of scheduling long workdays.


  1. Conway. Commit to being a morning person. Even on nights when you are up till 4AM. Self-discipline in this area sets the foundation of the whole day. I’ve found if I commit myself to being active in the morning I have a more productive day whether I’ve slept 99 minutes or 9 hours. Be aware that you will have slipups. But brush them off and recommit no matter how many times it takes.
  2. Debbie. Hire a mental health counselor to help implement strategies against becoming a workaholic. Having my daughter in law on staff, a licensed psychologist, allowed me to celebrate achievements, focus on big goals and drop my worries in a box in order to help me let go of all the overwhelming and guilty feelings I’ve experienced from running a company.
  3. Alex. When time doesn’t exist, it’s okay! What’s not okay is the absence of taking care of yourself. If you are not investing in health and wellness it will catch up to you so do what you can now to prevent massive burnout.
  4. James. I workout with my kids. Evening soccer literally plays double duty because they are playing for keeps! Recharging at home with my family is how I take care of myself along with tracking my calorie intake with the LoseIt app. I’ve lost 11 pounds in the last few months and I’m feeling great.

The bonus came from the host CEO, Chris from Pass it Down, which was the idea to create a wall of shame.

“Find a grandiose place to display all your failures. Not as a reminder of how you’ve failed, but to remind you those failures are now past. Sometimes just getting them out of your head will remove them from harming your confidence.”

Overall the growth startup advice that was passed out collectively from all CEO’s present, hovered on  the importance of making real life connections. Whether that be in a volunteer or mentorship setting, or talking with influencers in your space relationships are the foundation of any successful startup so take the time to foster the right ones, with true authenticity.

It was a pleasure getting the chance to hear these industry titans share their valuable insights and I’m looking forward to what next year holds!