We had the good fortune of connecting with Jill James and we’ve shared our conversation below.

Hi Jill, how do you think about risk?
My biggest risk was leaving my small, rural hometown where I had spent my whole life to go to college in Chicago. Once I figured out I could get on the level with kids who had every advantage in life academically and survive on my own in a large city, most job situations seemed less risky. After that, moving to New York to take a job on Wall Street felt like a much smaller leap. And I had the confidence I would be okay in the long run, so going to a start-up after business school didn’t seem like much of a risk.

One of the things I learned as a financial planner was a formal understanding of personal risk tolerance. I’m about as risk-loving as the average man, but as a woman, I’m an off the charts risk taker. That’s been important for me to understand in helping others approach change and hard decisions.

In my company, I challenge the notion that starting a self-funded small business is inherently risky and has a high failure rate. Yes, some business concepts will just not work financially, no matter how thought out your vision is. But I love the challenge of figuring out that puzzle – what IS the version that will work? How do we combine your purpose, your goals, and your vision into a sustainable business with great customers?

If you understand how your unit economics work, you can figure out how to build a business that will meet your goals. You need the vision and your founder story, but also a strong understanding of who you are, what you want, and what the financial story needs to be. The art without the science, or vice versa, is usually the failure point. Once you have both, the way you look at the risk is entirely different.

Especially now that I know how money and tax and business works, I always feel like I’ll find a way financially, so I try to focus on what my purpose and mission are in my work. The big risk to me is not challenging the status quo. I think work can be purposeful and fulfilling on my terms. And I want more people to have that.

What should our readers know about your business?
I started my business in the summer of 2015. I was COO at a venture-backed tech startup here in Los Angeles. I’d been through five or six start-ups by then in different jobs. I had wanted to start my own company for a while, but I never had the big idea that I felt would get venture or be a $1 billion company. But I also realized that start-up life was not going to work with the family life I wanted.

So, after all the hours and years spent on big ideas, I ended up starting out as a consultant. So many of us, especially right now, end up starting companies out of necessity, or because there’s something we make that somebody wants. And by doing that work, you figure out the bigger picture – what it takes to run a company, whether you like it, how to sell, what your vision is for the next version of what you do.

The media narrative is that founders start companies because they have these big, world-changing ideas. At about two years in, I realized that most self-funded founders start companies because they have a vision, an idea, or a customer, not because they want to run and build companies. But I do think starting a business is a world-changing opportunity, one purpose-driven founder at a time. And I like to run and build companies. So I started partnering with founders to fill in the strategy, finance, and operations sides of their businesses.

In the past year, I rebranded the company as The Jill James. What we do is driven by all my experiences, all the levels of jobs I’ve done, and by my formal entrepreneurial education. There is a version of your vision that fulfills your purpose, fits your life, delivers on your goals for financial independence and creating jobs.

So I developed a business design framework called CEO Confidence. It’s centered on founding CEOs, the right customers, and strong foundational economics, which is a huge gap for most self-funded founders. We need the story, the numbers, and the customers. Most founders also need and want elite accountability – that partnership with someone who can elevate their thinking and operations, but respects their vision and growth as the CEO. Beyond the technical knowledge, it takes a lot of empathy and encouragement. It brings me joy to see these founders own their role as CEOs and move beyond what their wildest dreams were when we started.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
As I’m writing this in early July of 2021, I feel new to the city again. Some of my favorite places have closed permanently or reconcepted post-pandemic. So I am embracing my own inner tourist to re-explore LA after 14 years here.

You haven’t visited LA until you have eaten at a nondescript strip mall restaurant and from a truck or plancha in a rando parking lot. I love the slightly burned pad see ew at Sanamluang Cafe in Thai Town. There used to be a guy named Rich who made his own barrel smoker and showed up in the 4100 Bar parking lot on the weekends with amazing wings and hot links. Grab a big pack of baby wipes and let’s sit on the curb and eat some messy delicious food.

I also grew up in a place where people wore their “church jerseys” on Sundays, so I love sports. LA Kings games for sure.

Being outside is a huge part of living here. You have to hike, even if it’s just a little baby walk up the hill to Griffith Observatory near sunset or walking around the Getty. I also love getting on a boat and being in the ocean. Until this year, I’d never gone whale watching. It changes your perspective to see the abundance even just a mile offshore. High on my list this summer is visiting Catalina. Most of my friends have young kids, so getting them to the beach or out on a hike is a priority. I like Descanso Gardens and Huntington Gardens because they can have some freedom to run ahead and explore.

I also love taking people to see Hollywood stuff, like the VIP lot tour at Warner Brothers or Universal Studios. (Why does the Waterworld stunt survive, by the way? Who’s going to that?) Once upon a time, my standard tour was the Le Pain Quotidien or Urth Caffe in West Hollywood, a hike around Runyon Canyon, and a drive to Malibu Country Mart, because it seemed everyone wanted to see someone famous. Now with social media (or perhaps my friends’ maturity) that seems less in demand. Now it’s more of a cabana day at the Beverly Hills Hotel. So much American culture and narrative comes from our backyard, it’s fun to help people connect with it.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
First, I have to thank my parents for making education and community engagement a priority. I’m a product of a small town K-12 public school, so I have to thank all those folks in Wisconsin for paying their property taxes and advocating for equitable access to education and public libraries. I also have to give credit to the University of Chicago and its donors for giving me an amazing life opportunity to access an affordable undergraduate education and radically change the trajectory of my life. I’ve had so many mentors and managers who have encouraged me to think bigger – Sherry Gutman and Steve Klass at the U of C, Joseph Cwietniewicz at AXA Equitable who taught me how to sell and build a relationship-driven practice, the late VC Kathryn Gould who funded my summer scholarship at Booth so I could afford to intern at a start-up. And big thanks to Amber Allen for giving me a nudge to start my company and becoming my first client, despite my waddling into lunch at 7 months pregnant.

Website: thejilljames.com

Instagram: @thejilljames

Linkedin: https://www.linkedin.com/in/jilldjames/

Youtube: https://www.youtube.com/thejilljames

Image Credits
I own all the photos

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