Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?

I grew up in Memphis where my dad was an entrepreneur. He owned an antique store and did estate sales, so while he was essential to the business, he also had a very flexible schedule. I remember how meaningful it was to have my dad at all my sporting events and to pick me up from school, so part of my desire to start a business was to have a similar opportunity with my son. I still take every Wednesday off just to hang out with him.

What is something you wish you would’ve realized earlier in your life?

Business ideas don’t have to be novel. In fact, the best ones are usually just a spin on an existing idea. I wasted a lot of time trying to come up with the perfect idea, but once I stopped worrying about it and instead focused on talking to potential customers about what they needed, it got easy.

What are bad recommendations you hear in your profession or area of expertise?

A lot of people think that success is all about working long hours, but I find the opposite from a lot of successful people; it’s really about balance. I remember hearing an interview with Martin Short, where he talked about how he self-assessed his own success using nine categories, and that really struck me. This guy has had a long, successful career in acting and he credits his success to the fact that he maintains balance in his personal life as well as his career.

Tell me about one of the darker periods you’ve experienced in life. How you came out of it and what you learned from it?

The first year of starting my business was hard. Even though we were growing and it was going well from the outside, the anxiety of having peoples’ paychecks depend on me, the pressure I put on myself to please clients, and being in the depth of the pandemic really wore me down. I had stretches where I woke up in the middle of the night, unable to stop worrying about it.

A few things helped me rise above the worry though. First, I joined a couple of peer groups (including Entrepreneur’s Organization). This helped me start building relationships with other entrepreneurs who were going through similar challenges. Next, I started working with a coach who has helped me deal with my own mental blocks and anxiety. Finally, I started letting go of more and trusting my team. I hired people who could deal with annoying clients; brought on managers to help me hire; got a salesperson to help lower my meeting burden. Having a support network has been huge for me.

What is one thing that you do that you feel has been the biggest contributor to your success so far?

• Talent stacking. I am not an expert in any one thing, but I have a weird mix of skills that uniquely positioned me to start Draft.dev: software engineering, writing, business management, and marketing.
• There are lots of people with software engineering skills (and I’ve never been that good of an engineer anyway), but very few of them also like to write. Even fewer have strong business and management experience, and even fewer understand the fundamentals of online marketing. Stacking this combination of skills allowed me to do a little bit of everything when the business was just getting off the ground, meaning I didn’t have to raise funding, find co-founders, or take a long time to get it started.

What is your morning routine?

• Up at 5:15 to work out for 30-60 minutes and walk the dog. Have a protein shake and get my son up and ready for school.
• I take him to school at about 8 and then triage emails from 8:30 to 9.
• At 9 am, meetings start, but I try to have at least 1 walking or eating meeting to break for lunch and move a bit.
• Two days per week, I will block 1-4 hours to focus on business development projects or writing, but I stay out of the critical path for client work.
• Typically, I’m in meetings back-to-back until 4 pm when I pick up my son and make dinner.
• I do family time until 8 pm, put my son to bed and then wind down around 8:45 or 9, usually reading a book for a few minutes before I go to sleep.

What habit or behavior that you have pursued for a few years has most improved your life?

Writing has brought me a ton of opportunities. My personal blog has gotten me job offers, my company blog brings us clients, and the guest posts I write help build awareness for the projects I’m working on. While I’m not the best writer, I’ve probably written something publicly every week for the past 12 years, so it adds up over time.

What are your strategies for being productive and using your time most efficiently?

• I track my time so I know how to hire and delegate work. Once I’m doing a task for more than 5-10 hours per week, it’s time to hire someone.
• I don’t have notifications on any device and I only check email 1-3 times per day.
• I set aside time each week to plan with my spouse. This ensures we’re on the same page as far as childcare, social plans, and chores.
• I wrote more about some of the strategies I use here in case it helps.

What book(s) have influenced your life the most? Why?

• How to Win Friends & Influence People by Dale Carnegie – I read this back in my early 20s and it helped me understand the power of persuasion and building a genuine connection with people. Your network is one of your most valuable assets, and this book taught me that you have to invest in it.
• The E-Myth Revisited by Michael E. Gerber – My dad was an entrepreneur, but he was also a critical cog in his business. Without him, the thing didn’t run. Reading the E-Myth helped me see that there is another way to start and build a business and that your company doesn’t have to rely on you.
• Big Magic by Elizabeth Gilbert – So many people assumes that creative pursuits are either all about getting lucky or having talent. In Big Magic, Elizabeth Gilbert shares her long, circuitous journey to finally write one big hit book. The point I took away is that discipline and grinding out the work are often necessary if you want to succeed in any creative endeavor.