It’s the time of year in Southern California that we call “May Gray,” which will soon give way to “June Gloom.” I know, I know, our job is beach. Which is why our tourism board doesn't want you to know we’re terrible at it in May and June. 

So this was my cold and cranky mindset going into last week’s book writing session, where we were asked to consider how to present ourselves authentically to our readers. It turns out, I am much more comfortable leaning into my “expert” persona than my personal story. I share the ups and downs with you, but not every week. While sometimes I write about my personal experiences and background, the balance of this newsletter is more “business owner things to know” than “what Jill did and how it felt.” 

I’ve earned my expertise. I worked on Wall Street, got certified to advise individuals and small businesses about money when I was 25, had leadership roles at five start-ups that have been acquired, and got two degrees from one of the world’s most challenging universities. (You may read that as yes, I am twisted.) Of course I have experienced personal and professional adversity. I’m on the fence about how much of that you want to hear from a person who’s helping you manage your big ideas and worldly assets. 

However, if the internet has taught us anything, it’s that you don’t need expertise to give advice. Since true domain experts are scary to most people, many of us defer to someone who’s more comfortable. Perhaps someone telling a personal story instead of an expert one. 

I’m hesitant to exploit my experiences to make you relate to me. And I respect that some stories are not mine to tell. But I do need to get better at storytelling, because that’s how humans create memory. So look out for more personal stuff. 

At the same time, I’ve got to help you be less scared of professionals. Recently, I was talking to a brave soul who brought a few new business ideas to a Strategy Session. I commended her on reaching out so early, as I hear from many people that they’re waiting to make the call until they, direct quote, “have their sh*t together.” 

Here’s the thing: no small business owner with a growing company really has their sh*t together. It’s a moving target. We get pretty good at one thing and move on to a new thing. When you’re building a company from scratch, you borrow expertise to help you quickly learn critical skills, because you can’t possibly become an expert at everything. At the same time, no one should talk down to you or hide behind jargon. 

If you are feeling scared of the professionals you’ll need in your business, like accountants, lawyers, and experienced specialists, find one person to coach you or  lead those conversations until you feel ready. Join a group of peer business owners. Pop into my monthly AMA and listen to what others are asking, or watch the replays. The entire archive is available here.  

Or, just do it scared. If they’re rude to you, feel free to say so and call somebody else. Being an expert doesn’t entitle anyone to be a jerk.

Why not give it a go? Practice with me. Book a 20-minute Strategy Session.

What does it mean? Controller 

Thank you to all the readers who have told me you want to know more about finance and business management but don’t know where to start. (Please, not Tik Tok.) I’m adding a new segment called What Does it Mean? I’ll cover a finance or business term each week. 

Today, let’s talk about controllers. Controller is an accounting role between a bookkeeper and a Chief Financial Officer (CFO). 

A bookkeeper will put your business expenses into tax-related categories and flow your spending through to some basic reports. They may not have formal accounting training, and that’s totally fine. 

Same goes for a CFO. A CFO may or may not have accounting experience. It’s a big picture management role. Their job is to advise you (and potentially a board) on how to use the company’s money for growth, investment, and debt service, informed by financial reports. 

Which brings us to the tweeny job: controller. A controller will transform your financial statements into useful information and elevate your reports into useful management insights. A controller should be able to build forecasts, evaluate labor costs, and assess margins and profitability. They will put systems and processes in place to reduce risks like theft, misappropriation, and errant bill pay. Typically, they have studied accounting, and may be working toward a Certified Public Accountant (CPA) designation. 

When it’s time to level up, many small business owners ask for a CFO, but what they actually want is a controller. 

If you want to know more, check out “Cash Flow Show: Accounting High” hosted by CPA Nikole Mackenzie of Momentum Accounting. A recent episode, 7 Signs You Need a Controller, gives scenarios for when you might need a controller and how to find and hire one. 

What terms and management concepts do you want to know about? Hit reply and tell me!

Media Kit 

The permanent player / coach: It’s just reality: you have day-to-day work responsibilities in your business. I enjoyed this post from a CEO about how to thrive when you lead and manage a company while doing a “day job.” 

Are privacy policies good for small businesses? My LinkedIn is packed with small business owners traveling to Washington to lobby Congress about why a national privacy policy would be terrible for the Royal Us. The arguments are that free ad-supported services help low-income folks with access and small businesses need cookie-based targeting to find niche audiences. Here’s some of the data they’re using. Are nine out of ten of us really buying ads on Facebook? Kinda feels like we’re carrying Billionaire Zuckerberg’s water for K Street.

Health research equity for Black women. The American Cancer Society is recruiting 100,000 Black American women for a 30-year study on cancer development and outcomes. Participants will be polled semi-annually about health data, socioeconomic status, and experiential and environmental stressors. If you’d like to participate, learn more here. 

What I’m watching: Hacks on Max, American Fiction on Prime Video, and WNBA League Pass.

What I’m listening to: The Car by Arctic Monkeys, All Born Screaming By St. Vincent,  and What Now by Brittany Howard.

What I’m reading: The Confidence Game: Why We Fall for It…Every Time by Maria Konnikova. Also McSweeney’s “What your favorite ‘90s band says about the bored suburban mom you are today.” Please send your results, my text threads on this have been side-splitting.