Just Figuring It Out

Ever feel like you're the only person who can do things right in your business?

You've hired people, handed off responsibilities, and maybe even gotten burned a few times. So now, instead of delegating, you find yourself taking everything back on.

But what if the biggest thing holding your business back isn't your team, your systems, or your finances? What if it's your struggle to let go?

In this episode of Just Figuring It Out, Will, Alex, and Ian get into the messy reality of business ownership, from tax frustrations and past hiring mistakes to the emotional side of trusting others with something you've worked so hard to build.

They discuss:

Why business owners struggle to delegate, even when they're overwhelmed

How bad hiring experiences can make it harder to trust again

The difference between taking ownership and trying to control everything

Why understanding a responsibility matters before handing it off

How to stop feeling like everything depends on you

Why letting go can create room for your business and team to grow

How curiosity can help you handle the difficult parts of entrepreneurship

Plus, they share their own experiences with AI, taxes, hiring, and learning that someone else might actually do the job better.

The big takeaway? Growing a business doesn't mean figuring out how to do everything yourself. Sometimes, it means learning what you no longer need to carry.

If you're a business owner who's struggling to delegate, trust your team, or step away from day-to-day responsibilities, this conversation is for you.

Subscribe to Just Figuring It Out for real conversations about business ownership, leadership, finances, and everything we're still figuring out along the way.

Everyone is talking about AI.

But are you actually using it to get work done?

In this episode of Just Figuring It Out, Alex, Ian, and the team break down what it really looks like to use AI as more than a chatbot, writing assistant, or brainstorming partner.

The conversation focuses on a simple question:

What if you could hand AI real work that someone on your team is already doing?

From automating repetitive computer tasks to analyzing calls, managing follow-ups, reviewing financial information, creating SOPs, and even building systems that can interact with your email, calendar, files, and other business tools, we explore where AI is becoming genuinely useful for business owners.

You'll learn:

• Why AI needs more than just a good prompt to do useful work
• The 6 things AI needs to complete real work: a goal, context, process, eyes, hands, and verification
• Why AI should be treated like a “superhuman toddler”—powerful, capable, but still requiring oversight
• How to avoid blindly outsourcing your critical thinking, creativity, and understanding
• How to identify repetitive tasks in your business that AI could take off your plate
• How business owners are using AI for call reviews, follow-ups, SOPs, financial modeling, scheduling, customer interactions, and more
• Why starting small and testing AI on low-risk tasks can help you build trust in what it can actually do
• How AI can become an expertise amplifier when you already understand what good work looks like

One of the biggest ideas from the episode is that you don't need to become an AI expert or “catch up” with every new tool.

Instead, find one annoying, repetitive process in your business and ask:

“Could a computer do this for me?”

Then start experimenting.

This is a practical conversation about using AI to save time, reduce cognitive load, improve processes, and make running a business a little more enjoyable without handing over your brain to a machine.

🎙️ Just Figuring It Out is a podcast about business, money, leadership, technology, and the messy process of figuring things out as you go.

Subscribe for new episodes every Wednesday.

Why does every decision still seem to land on your desk? Why do team members wait for you to solve problems, make decisions, or tell them exactly what to do?

In this episode of Just Figuring It Out, Will, Alex, and Ian dig into one of the hardest parts of running a business: learning how to actually lead your team instead of constantly rescuing, fixing, and managing everything yourself.

They talk about why so many performance problems are really clarity problems, how to make better requests, create a culture where people feel safe asking for help, and what happens when leaders unintentionally shut down new ideas or make their team afraid to bring problems to them.

They also dive into practical ways AI can help business owners from call reviews and team training to automating repetitive tasks and analyzing what's actually happening inside the business.

If you're trying to build a team that can think, solve problems, and operate without everything running through you, this conversation is for you.

Why is it so hard for business owners to slow down?

Even when things are going well, there’s this constant pressure to push harder, hit the next revenue goal, grow faster, and “finish the year strong.”

In this episode of Just Figuring It Out, Will, Alex, and Ian talk about what happens when the pace finally starts to slow down and why that can actually feel uncomfortable.

They dive into:

• Why business owners struggle with quiet seasons
• The pressure to constantly grow and hit bigger revenue goals
• Learning when it’s time to push and when it’s time to recover
• Why “doing more” can sometimes be a way to avoid dealing with what’s actually going on
• How business owners can create seasons of recovery without feeling guilty
• The difference between scarcity-driven growth and building a business that gives you more time and peace
• Why having more time, energy, and money can be surprisingly difficult to handle
• How trusting yourself, your team, and your business changes the way you think about the future

Maybe the goal isn’t always to grow faster.

Maybe it’s to build a business you actually enjoy owning.

Why is it so hard to let go of the things you’ve been doing yourself?

In this episode of Just Figuring It Out, Will, Alex, and Ian dive into one of the biggest challenges business owners face as they grow: delegation.

It sounds simple—hire someone, hand off the work, and buy back your time. But in reality, letting go can be incredibly difficult. You might not trust someone to do it as well as you, you might be afraid of making the wrong hire, or you might secretly feel like being busy is part of what makes you valuable as an owner.

The team talks honestly about their own experiences with delegation, hiring, building processes, trusting team members, and learning to accept that someone else's version of "good enough" doesn't have to look exactly like yours.

They also tackle a question every growing business owner eventually faces:

Should I learn this myself, or should I just hire someone who already knows how to do it?

And with AI making it easier than ever to build systems and automate work, they explore whether technology is actually helping us buy back our time or sometimes just giving us another way to avoid the harder work of leading and trusting people.

In this episode, we cover:

• Why business owners struggle to delegate
• How to know when it's time to hire vs. learn a skill yourself
• Why hiring someone doesn't mean you can completely walk away
• How to define what a "good job" actually looks like
• The importance of patience when training and delegating
• Why your identity can become tied to doing everything yourself
• How to build a business that doesn't depend on the owner
• Delegation, leadership, and learning to trust your team
• When AI helps and when it can become another distraction
• How buying back your time can change your business and your life

If you're constantly thinking "It's just easier if I do it myself," this episode is for you.

How many bookkeepers have you gone through?

If you're on your fourth, fifth, or even sixth bookkeeper and you're still frustrated, the problem might not be as simple as finding a better bookkeeper.

In this episode of Just Figuring It Out, Will, Alex, and Ian break down one of the most common problems they see with business owners: the constant cycle of hiring and firing bookkeepers without ever getting the relationship to work.

They talk about what a bookkeeper is actually responsible for, what they shouldn't be expected to do, and why so many business owners accidentally expect their bookkeeper to function like a CFO, controller, or financial advisor.

They also dive into the owner's side of the equation—communication, setting expectations, reviewing the books, communicating changes, understanding your financial reports, and taking ownership of the numbers instead of completely handing them off.

In this episode, we cover:

• Why business owners keep going through multiple bookkeepers
• What a bookkeeper actually should—and shouldn't—do
• Bookkeeper vs. controller vs. CFO
• Why cheap bookkeeping can come with hidden costs
• What you should expect from a good bookkeeper
• What your bookkeeper needs from YOU
• How often your books should be completed
• Why business owners need to understand their own numbers
• When it's time to take responsibility instead of blaming the bookkeeper
• How to build a better relationship with your financial team

If you've ever thought, "I just need to find the right bookkeeper and then everything will be fixed," this conversation might change the way you look at the problem.

Should you really be comparing your business to industry benchmarks?

In this episode of Just Figuring It Out, Will, Alex, and Ian take a deep dive into where industry benchmarks actually come from and whether business owners should trust them when making important decisions.

They unpack how benchmark data is collected, who contributes it, why the numbers can be heavily skewed, and what major factors often get left out including owner compensation, geography, debt, business structure, and the actual goals of the business owner.

The conversation gets especially interesting when they ask a bigger question: What does “successful” even mean?

Instead of blindly chasing a 40% margin, a certain ROAS, or whatever number someone says your industry “should” hit, the team explores why your own goals and definition of success may be a much better benchmark.

In this episode, we cover:

• Where industry benchmark data actually comes from
• Why benchmark data can be biased or incomplete
• The problem with comparing businesses across different locations and business models
• Why owner compensation can completely change the picture
• How debt and cash flow affect benchmark data
• Why “average” doesn't necessarily mean “successful”
• When industry benchmarks can actually be useful
• How to create your own standards for your business
• Why comparing yourself to other businesses can create unnecessary stress

If you've ever looked at an industry benchmark and thought, “Why am I not hitting that number?”—this episode is for you.

You’re doing more revenue. You’re landing bigger clients. Your business is growing.

So why does it still feel like there’s never enough money left?

In this episode of Just Figuring It Out, we break down one of the biggest problems we see with growing businesses: making money is not the same as keeping it.

You might have a $3M+ business and still have no idea where the cash went. Your Profit & Loss statement might show a healthy profit while your bank account tells a completely different story. And sometimes, the problem isn’t that you need more revenue, it’s that money is quietly leaking out of the business.

We break down real examples from businesses that lost or missed out on $73K, $90K, $150K, $700K and even $900K+ because of problems hiding underneath the surface.

In this episode, we cover the 4 financial doors every business owner needs to understand:

1. A system is not a control — How one business lost at least $73,000 because nobody was checking the money moving through their payroll system.
2. The job isn't done until the money lands — How $90,000 in earned revenue got stuck in accounts receivable.
3. You can't price what you haven't measured — Why businesses can think they're making a 20% margin while actually making 5%.
4. Profit without a destination gets absorbed — Why growing revenue isn't enough and how to give every dollar in your business a job.

You'll also learn why your P&L doesn't tell the whole story, why clean bookkeeping isn't the same as understanding your numbers, and what you should actually be looking at if you're running a 7-figure business.

If you're a business owner doing $500K+ in revenue, especially if you're in a service, construction, contracting, healthcare, or other growing business, this episode will give you several things to check in your own numbers.

The big takeaway: Revenue is a vanity metric if you can't keep the money.

What happens when the next big opportunity looks like the answer to all your problems?

In this episode of Just Figuring It Out, Will, Alex, and Ian unpack one of the biggest traps business owners face: the shiny object.

A new service.
A new product.
A new revenue stream.

A new idea that suddenly feels like the thing that will fix everything.

But sometimes, chasing something new isn't growth. Sometimes it's a reaction to fear, boredom, cash-flow pressure, or frustration with the business you're already running.

The conversation starts with the decision to add bookkeeping services to their business after years of intentionally staying focused on their core offer. From there, the discussion goes much deeper:

• Why focus can be more valuable than adding another revenue stream
• How fear can make a new business idea look more attractive than it really is
• The difference between a band-aid and a blueprint
• Why business owners often try to sell their way out of operational problems
• How chasing new ideas can create unnecessary stress for your team
• Why the wrong hire can cost more than the opportunity you were trying to capture
• How to test a new idea without betting the entire business on it
• Why cash reserves can give owners the breathing room to make better decisions
• When contraction can actually be part of healthy expansion
• Why “more” isn't always better and why a simpler, more profitable business might be exactly what you need

Most importantly, the three of us wrestle with a bigger question:

Are you building the business you actually want or are you constantly chasing the next thing because you've convinced yourself that more means better?

This isn't a conversation from people who have everything figured out.

We're living through these decisions ourselves.

That's the whole point of Just Figuring It Out.

If you're a business owner facing a new opportunity, considering another revenue stream, or simply wondering whether you should keep pushing for more, this episode is for you.

Ever wondered what businesses are actually worth buying?

In this episode of Just Figuring It Out, the team starts by tackling a problem that's keeping a lot of business owners up at night getting paid. They share practical strategies for improving collections, increasing cash flow, and making it easier for customers to pay without damaging relationships.

Then they switch gears for a fun (and surprisingly revealing) exercise: if they had the opportunity, which businesses would they actually buy?

From bookkeeping firms and marketing agencies to med spas, construction companies, physical therapy clinics, and home service businesses, they break down what makes each business attractive or a hard pass.

Whether you're building a business, thinking about buying one, or just curious how experienced operators evaluate opportunities, this episode gives you an inside look at how they think.

In this episode:

• Why so many businesses struggle to collect payments
• Systems that improve cash flow
• The psychology behind asking to get paid
• The businesses they'd invest in and the ones they'd avoid
• What separates a good business from a great investment