Before becoming a partner at Stride I was the co-founder and CEO of a healthcare technology business for six years and before that I was the co-founder and CEO of a healthcare services businesses. I have been there when we were two guys and a desk and two cellphones. I have been there through venture financings and growth. I have also been there through layoffs and exits. Yes, the roller coaster that we all go through.
One of my greatest learnings is that entrepreneurial courage is not always rolling up my sleeves and getting it done myself. Courage is having the confidence to have someone else take on certain roles even though I could do it myself.
For me, the area was finance and accounting (why I am a Partner at Stride now will make so much more sense). I knew how to do it. I had an accounting degree. I worked in investment banking on Wall Street for many years. I could build models, run variance reports, build financial board decks, even do journal entries. And I did a lot of that.  But that wasn’t why my investors invested in me. What I should have done was acknowledge that while I could do the work, my highest and best use would have been to have someone smarter and faster than me do it. That would have been courage. Instead, it was easy to retreat to the place where I was most comfortable (and in control) but that wouldn’t move the business forward in a material way.
Do you want to have the courage?
Here Are My Top 5 Recommendations to Self Reflect on Your Own Business
1. Communicate Your Role Clearly to the Organization
The owner of a business needs to make sure the company doesn’t run out of money and has a great team to execute. There should be no ambiguity there. That work may show up in sales, capital raising, recruiting and networking. Tell your team what to expect from you and then stay in your lane.
2. Pretend That You Don’t Have That Skill
It was so easy for me to hire developers to code our application or hire doctors to see patients. I never even imagined I could take that on. I wanted to hire the best. But when it came to the thing I was pretty good at, I didn’t feel that same urge. Imagine you didn’t have the skill and take action.
3. Hire Someone That Is Smarter Than You
When you have a practical skill that you’re good at, it’s hard to find someone better than you. You have a bias and filter that doesn’t exist when hiring someone outside of your experience domain. Create a clear job description of the qualities or characteristics you are looking for and then stick to it in the interview process.
4. Put a Value on Your Time
Your investment dollars are not being put to good use if you are doing work that someone could do at a fraction of the cost. If you have outside investors, that would probably be pretty disappointing to them.  Every dollar of revenue and profit has a multiple of value applied to it and your job is typically to drive revenue. Stay in that swim lane.
5. Lay out Your Organization’s Roles and Responsibilities
There are relatively few things that a CEO needs to do right but those things have a big impact. They are also uniquely his/hers to execute. These are things like hiring senior talent, strategy, and capitalization. When you map out the roles required for you to deliver on your business model you will see where the gaps exist and your mandate is to have a plan to fill them (with people other than you).
Courage in Business
Courage is about making investments so that you can get leverage in your business and scale. There are only so many hours in the day and highest and best use must be applied to those areas that only a founder/CEO/owner can perform.
