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The more your business grows, the more complicated it gets to manage your money.

Think taxes, structure, payroll – and a whole set of decisions no one teaches you how to make.

But Lorie Jones, founder of Fearless Financial Advisors, has built her career helping founders manage what comes next financially.

In this conversation, we go deep into the three stages every founder goes through – and how to navigate each one.

I think there are three financial stages that a business goes through. Can you walk us through what those are?

Lorie: I love this framework because it really reflects what happens in real life – because I’ve noticed that the questions people ask change as the business grows.

Stage one is getting set up. You’re just trying to get the business off the ground and build enough momentum to keep going. You’re figuring out the basics, like how to structure the business, how to get paid, and how to separate things out. It’s very foundational.

Stage two is making money and growing. You’re getting more consistent revenue, maybe even feeling like this could be a long-term thing. That’s when decisions get more complex.

You start thinking about taxes, how you’re paying yourself, and whether you’re actually setting yourself up well financially.

Stage three is optimizing and protecting income. It’s when the business is doing well, and now you’re dealing with the complexity that comes with that.

You’re in higher tax brackets. You have greater exposure. At this point, it’s not just about earning money anymore. It’s about protecting it and being smart about how you’re managing it.

What worked in stage one is not going to work in stage three, and that’s where people get tripped up.

How should founders think about which stage they’re in? Is it based on how long you’ve been in business, or is there another way to look at it?

Lorie: It’s definitely not about time. It’s really about income and stability.

In stage one, you’re usually either not making much money yet or it’s inconsistent. You’re still figuring things out, and you’re probably putting everything you have – time, energy, even money – back into the business just to get it going.

Stage two is when you’re making enough to support yourself and feel some momentum. I usually think of that as around the $100,000 mark, give or take.

You’ve either left your day job or you’re seriously considering it, and you’re starting to feel like, “Okay, this is working.” It’s a really exciting stage, but it’s also where you need to start being more intentional.

Then stage three is when you’re making strong income, and taxes become a real issue. You’re in higher tax brackets. You have more exposure. And the decisions you make start to have bigger consequences. This is where complexity really shows up.

It’s less about how long you’ve been in business and more about what your financial picture looks like.

How much are you making? How consistent is it? And how much are you at risk of losing if something goes wrong?

What’s the most important advice you have for founders at each of these stages?

Lorie: The advice depends on where you are. In stage one, the most important thing is protection. You need to set up your LLC – no question about that. Having an LLC creates a barrier between your business and your personal life. Without it, you’re exposed. Your home, your savings, everything could be at risk in a lawsuit.

And it’s not just setting it up; you have to treat it like a real business.

Separate bank accounts mean separate expenses. It’s actually really easy to do, but people overcomplicate it or put it off. This is one of those things where you just need to get it done. You don’t have to be perfect. You don’t have to have everything figured out. But you do have to protect yourself.

In stage two, the focus shifts to being more intentional about your money. This is where things like electing S-Corp status start to matter, because now you’re making enough that tax strategy can actually save you money.

It’s also the stage where I really encourage people to start thinking about their future. A lot of founders spend stage one just trying to survive, and they put off saving for retirement or building long-term wealth. But you didn’t start your business just to work for nothing. You started it to create something better for yourself.

So this is where you start looking at things like a solo 401(k), maybe a Roth option, and then actually putting money aside. Not everything should go back into the business anymore.

Then in stage three, the mindset shifts again – now it’s about optimization and protection. You’re making good money, so the question becomes: how do you keep more of it?

This is where more advanced strategies come in – profit sharing plans, more sophisticated retirement structures, and reducing your tax burden over time. You might also be thinking about employees at this stage and how to support them with benefits like a 401(k).

At this point, your job isn’t just to earn. It’s to protect what you’ve earned and make sure it’s working for you long-term.

And across all of this, I would say these are just guidelines.

Everyone’s situation is different. Having someone who understands your specific situation and can help you navigate these decisions is incredibly valuable, because complexity grows as your business does.

What We Can Learn from Lorie Jones:

The average fractional serves 2-6 clients at once, working 10-15 hours per month per client.

That sounds manageable on paper. Hard, but not impossible.

But in reality, it’s a high-wire act.

Managing multiple clients simultaneously is a completely different skill set than being good at your job.

I’ve worked and talked to fractional leaders across multiple industries over 25 years. From them, I learned four best practices to avoid burning out quickly:

Let’s dive deep into each of them.

One of the biggest mistakes that a fractional can make is treating their calendar like a task manager.

They book “attend strategy meetings,” “review financial reports,” “draft presentations” across multiple clients in a single day. By 3:00 PM, their brain is mush from constant context-switching.

What works for many fractionals instead: dedicate entire blocks of time to single clients.

It could be a whole day for Client A and the next day for Client B – or if work is less demanding, Client A in the morning and Client B in the afternoon.

During each client’s time block, you do everything for them.

Emails, calls, strategic work, and tactical execution, if the scope applies. Be fully immersed in their world, challenges, and language.

Then, close that mental tab completely and move on to the next client.

This approach is great because it allows fractionals to stay sharp and do deep work for each client.

Once your calendar is set, fractionals also need to face another uncomfortable truth:

Juggling several clients might lead to conflicting priorities, accidental information leaks, and trust issues.

You need a system to protect both the clients and yourself.

Here’s how I recommend you do it:

Individual tactics are great, but the key is having a strong underlying system. Fractionals that thrive have defined operational methods that run on autopilot.

An effective operating system includes:

This structure keeps fractionals proactive instead of reactive.

With the demand growing, so does the temptation to say yes to every project.

Nearly half of fractional execs report excitement about increasing opportunities, and 62% of them express satisfaction with their fractional business.

But satisfaction doesn’t mean easy.

Every fractional who thrives stays disciplined in their work. They show up when needed, but don’t try to be everywhere all the time.

We’re all used to over functioning all the time, so it’s difficult for us to set boundaries and be honest about our capacity.

But stretching ourselves too thin only causes our work (and reputation) to suffer.

Better serve two clients exceptionally than five clients poorly.

(We have a great article on setting boundaries here, so make sure to check it out.)

The industry experiences high churn since most clients drop off within two years.

The very nature of our work is about serving our clients until they don’t need us, and this usually happens at the 12-month mark.

The best fractionals actively work themselves out of a job. This means mentoring internal team members, documenting processes, and transferring knowledge continuously.

But there’s a beauty to this approach: you create advocates who can hire you or refer you to their network.

This keeps the pipeline fresh with new challenges instead of maintenance work.

Managing multiple clients simultaneously is a skill that fractionals develop over time.

You’ll make mistakes. You’ll overcommit. You’ll learn what works for specific situations.

But it’s best to start with clear systems and stay disciplined.

My challenge to you: take a hard look at your calendar this week.

Does it reflect your priorities? Are you showing up where you’re most needed?

If not, it’s time to adjust.