Jill James transforms self-funded companies into high-growth businesses by helping founders design and aligns strategic operations to their ambitious visions.
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 a dairy farming town in central Wisconsin with (real stats) 100 times more cows than people. I lived there my whole life until I left for college in Chicago. My dad was a teacher and sports coach and my mom ran a daycare. That really centered us in the community. My dad’s parents had a general store in another small town. I used to visit them for weeks at a time, stock the candy case, and work the soda fountain. And as much as I didn’t think of it this way at the time, my two grandmothers and my mom all ran businesses that let them be moms. That’s shaped some of my thinking about how business ownership is the key to designing work that also works for you and your life.
What is something you wish you would’ve realized earlier in your life?
Just start. I waited for years to have the billion-dollar business idea while I worked on other people’s ideas. When it came down to it, I started an utterly unscalable services company when I was 7 months pregnant because that was the best option. Start doing the work, learning how to find customers, and selling and delivering things. Your idea will evolve and you’ll have space to learn how to run a company.
What are bad recommendations you hear in your profession or area of expertise?
Bigness. Scale. I hear lots of self-funded founders pushing for scaled revenue growth without unit profitability, direction, or intention. 99% of companies will never get venture capital, but they try to use that playbook. There’s a little slice of the world that gets to blow the GDP of an emirate while playing business and spinning yarns. The rest of us operate in the real economy and create jobs and value. We work with consultants who bring specific skills and solutions. We don’t have to make everyone a W-2 employee to maximize investor return or grow as fast as possible. We do have to operate profitably. Self-funded founders get to decide the best use of profits, and sometimes it’s getting paid or outsourcing a task you hate. Design your company to suit your goals and define success for yourself.
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?
I’m just at the end of an 18-month divorce. Divorce is by its nature destructive and disrupts most of the patterns and relationships you’ve come to count on. Going through a divorce in a global pandemic gave me perspective. The first two people I told were facing even more challenging realities of grave illness and death.
Have gratitude. I have my health, I have a healthy child, we have food and a home. You can have gratitude without papering over your other emotions. I believe in my ability to rebuild other things. Sometimes you need space to feel your feelings and work has to wait. I was honest with my clients about what was going on, which was really scary, but they gave me grace. As entrepreneurs, we have to be especially aware of our mental and physical health, build supportive communities around us, and be vulnerable. Ask for help. Work is not always first. Take of yourself and your people.
What is one thing that you do that you feel has been the biggest contributor to your success so far?
I’m endlessly curious about how things work. I’m first and foremost a student, which is why my collection of clients ranges from hair extensions to cybersecurity software. As much as I’ve built expertise, it keeps me hungry and humble to know how much more I have to learn and how fast we’re now generating new ideas and technologies. I synthesize a lot of ideas from watching and listening.
What is your morning routine?
I’m a bit inconsistent in these because I have custody of my son every other week. On the weeks I’m not ruled by the school schedule, I wake up around 6:30, write a bit, sometimes go for a hike in Griffith Park, or read the news. On weeks with my son, I wake up around 6:30 and spend the next 90 minutes in service of getting everybody fed, clothed, and out the door. I will occasionally get up at 5 AM to work on a project while it’s quiet, but I’ve not been able to join the 5 AM Club consistently.
What habit or behavior that you have pursued for a few years has most improved your life?
My high school guidance counselor once told me that I struggled with “unstructured time.” I’ve learned that unstructured time is where we find breakthroughs. So now I create some purposely unstructured time into my week. I don’t take meetings on Fridays. I pursue personal projects, write, have chatty meandering lunches, or simply sit and think. I used to call it “research” or “creative time” but I no longer put pressure on making it productive. It’s about creating space to invite the unexpected and let ideas go where they want to go.
What are your strategies for being productive and using your time most efficiently?
I’m a lot less concerned about maximizing my time-to-productivity ratio than I used to be. My #1 productivity tip is to shut off all the alerts – desktop, mobile, smartwatch. Most of us are trying to work with our brains at a carnival with flashing lights, yelling, and a steady diet of cotton candy. You cannot think or focus with constant interruption. I’ll go a step further to put my phone on do not disturb and take my smartwatch off when I need to do a couple of hours of deep thinking work. During those times, I delegate timely monitoring to my assistant.
I try to do one thing at a time and am realistic about what’s possible in an executive day. Switching is a productivity killer. I use time blocking and no-meeting zones. If I’m in a meeting, I focus on the meeting. I use a Remarkable tablet so I can take and share notes without the distraction of typing.
What book(s) have influenced your life the most? Why?
Mindset by Dr. Carol Dweck. Learning that skills are not innate, but can be developed through effort and intention, was a game-changer for me. There are all kinds of things I wrote off as being “bad” or “limited” at – when I would never be The Best — that I now enjoy for the experience and comradery.
Do you have any quotes you live by or think of often?
“I use this one so often that I have it framed on the wall of my office: Start where you are, use what you have, do what you can.” – Arthur Ashe