Episode 10: What to Expect When Your Bookkeeping Business is on Track to Hit $1 Million with Jolene Fleming

Written By Alyssa Lang

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In this episode, I interview Jolene Fleming, CEO of Upper Left Accounting, incredible business owner and mother. We talk about her experience with buying a book of business, how she implemented systems and processes that transformed her business and how she's on track to hitting $1 million dollars.

In this episode you’ll hear:

  • What it was like for Jolene to purchase a book of business from another firm owner

  • The process of a buy out and what that looks like

  • How much she bought the business for

  • How she implemented efficiencies, SOPs, processes, etc. in growing the business

  • How she implemented Kickoff with Asana for Bookkeepers & Accountants in 4 days

  • How she implemented Breakthrough for Bookkeepers & Accountants and how it changed her firm

  • Her experience taking vacation and time away from the business

Resources mentioned in this episode:

⚙️ Loom (screen recording software)

⚙️ Miro (virtual white boarding and process mapping tool)

🔨 Whiteboard Wallpaper

⚙️ Jasper.ai

💻 Breakthrough for Bookkeepers & Accountants

💻 Kickoff with Asana for Bookkeepers & Accountants


Listen to the Full Episode here 👇🏼

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In this episode, I interview Jolene Fleming, CEO of Upper Left Accounting, an incredible business owner, bookkeeping expert, and mother. We chat about her experience with buying a bookkeeping business, how she implemented systems and processes that transformed her business, and how she's on track to hit $1 million dollars.

In this episode, you’ll discover:

Okay, let’s GROW!

The Ins and Outs of Buying a Bookkeeping Firm

This is actually Jolene’s first podcast interview, which is pretty amazing because how she hasn’t been snagged up by a million people I will never know. She has SO MUCH to share, and you’re going to learn all the things!

When I first met Jolene, her systems were kind of a hot mess. And now her team has the things in place they need to be on track to make a million bucks!

She recently bought a business, which is daunting and interesting to so many in this audience. She had previously worked for this company as an employee, took a short but sweet stint as a stay-at-home mom, and went back to work for them again.

She worked part-time from home doing the mom and the work things (shout out to those moms, because y’all are incredible!). She quickly helped the business grow, went full-time, and hired two more employees!

That turned into a conversation about what everyone deeply wanted, and it turned out that the owner was ready to sell, and Jolene was ready to break out on her own. They both hired a lawyer (highly recommend), and they completed an asset sale.

Jolene comes from a longgg line of business owners (her great-great-grandfather invented the sleeping bag. Whaaaa!). And because she was immersed in it, she knew business ownership was her jam. Which is why she decided to dive head first into launching her own bookkeeping and tax firm!

Buying a business and/or a client list is a lot of work. I know because I also bought out my business partner last year, which is a mission. And I want to sell in the next few years, because I have a goal to retire by 35. But that means I need to grow it big, quickly.

So where do you start, and what does it cost? Client base and revenue from the business evaluator will be what determines the price point. For Jolene, she had 70 clients and bought it for $250,000. The previous owner did the payout through the company— through a five-year buyout. She carried the note, and the transition was super smooth.

Keep in mind: You may lose clients. Jolene had connections with clients. But if you are buying from a marketplace, clients might not be comfortable with someone new taking care of their books.

Cross your Ts. Dot your Is. Especially if you're the face of your company, work to make or maintain a personal connection with your clients so you don’t see too much turnover!

Transitioning Processes From One Owner To The Next

In the first year, Jolene’s firm doubled in revenue. Amazing. But a LOT. While she was managing the day-to-day operations, she learned she isn't the best at everything. And that’s where the SOPs, processes, and systems come into play.

A lot of processes do continue to grow with a firm, and there can be a lot that needs to change if there are not enough or the correct processes or policies in place. So focus on what your needs really are. Is growth your real need, or do you need to settle in the cracks of your foundation so you can prepare yourself to scale?

Realizing they needed some systems help— Jolene joined my course Kickoff with Asana Bookkeepers & Accountants. And in 4 days— she had systems in place that not only helped the foundation of her business, but she also grew in year two! Even though that wasn’t the goal.

The main lesson? Ask for help in areas that aren’t your strength. Maybe the previous owner had a different system than one that doesn’t work for you. I’m so competitive that it really bothers me when I am not great at something. I hate not knowing how to do things!

But it’s so much better to be a master of one trade than a jack of all. It’s ok to reach out to others and let them step in in areas where you’re not as strong.

Breakthrough for Bookkeepers & Accountants has supported growth for Jolene by getting her house in order. Nothing is built on a shaky foundation for her. She’s also delegating more, which is a MUST when you’re trying to grow.

Sometimes business ownership sucks and you’re ready just to burn it all down. But hearing the things that Breakthrough for Bookkeepers & Accountants has done to help her business is SO inspiring!

Taking Time Off (Or Away) As A Business Owner

Jolene’s trying to get to the point where she’s doing more speaking events. (Can I hire her to be the face of the events so I don’t have to speak???) So because she wants to create more time to present and educate— how does she set up her business to be able to step away?

Implementing tech, automations, and SOPs! It helps tremendously. Put all of your client information in one place so that if you take a trip and someone needs to step in they can just take a peek at the client and their needs.

Take time as a team to break down the tasks you use for each client so you don’t become the company's bottleneck. Have this intensive day, even if you’re a business of one. Then start implementing! You can’t automate if you don’t have a map for your team.

Another tip: Use Loom! Do the thing. Record yourself doing it. Boom. You’re building an SOP. Don’t make it this giant thing that has to be written out.  And processes may need to be re-recorded or updated. Use these videos as reminders of things that’ve changed. You don’t have to do this alone, and you don’t have to be the bottleneck forever.

(If you throw that transcript into CHAT GPT or Jasper.ai, you could even generate a task list. How’s that for a time saver?!)

So if you’re on the fence about how to confidently move forward in your business or you’re thinking of buying a business— I HAVE to suggest Breakthrough for Bookkeepers & Accountants!

Don’t know if it’s right for you? Look for your biggest bottleneck and pain point. What are you searching for? I’m willing to bet you’ll  find a solution in this program. Jolene says she loves that you can just jump into the module of your pain point to address your biggest issues first.

She feels like Breakthrough allowed her to go to Hawaii and be present with her family because of the systems, processes, and team management she learned from the program’s content!

The biggest added value? The community. It’s my favorite part. Find people to bounce ideas off of, get support from, and connect with some of the BEST humans in our industry!


About our guest:

Jolene Fleming is the CEO of Upper Left Accounting and she’s a profit and growth strategist, opportunity detector and someone who’s never met a puzzle she didn’t like. Jolene wants to win for her clients. Unapologetically growth-driven, Jolene's financial strategies turn small businesses into not-so-small businesses. She's transparent and unambiguous about it and still bubbles up with joy every time her tactics help someone reach a level of success that exceeds their expectations.

The entrepreneurial spirit is deep-rooted in Jolene’s DNA. She comes from a long line of business owners including her grandfather who was a veterinarian, and her great great grandfather who invented the sleeping bag. When she’s not driving profits up for her client list, you’ll find Jolene riding horses with her sister and mom, or beach loafing with her husband, and three kids!


Connect with Jolene Fleming:

Connect with her on Facebook: facebook.com/upperleftaccounting.com

Connect on Instagram: @upperleftaccounting


Thanks for listening. If this episode inspired you in some way, take a screenshot of you listening on your device and post it to your Instagram stories and tag me, @workflowqueen For more information about the Conquering Workflows & Systems for Bookkeepers & Accountants Podcast or interest in our programs or mentoring visit our resources below:

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Alyssa Lang https://www.workflowqueen.com
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Episode 9: Legal Questions Bookkeepers & Accountants Often Ask (Answered!) with Linsey Levine