Just Figuring It Out

Will Boyd, Alex Engar, & Ian Hogan
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  • Entrepreneurship

Just Figuring It Out is a show for small business owners who are in it and navigating the messy, rewarding, confusing reality of building something that actually works. Will Boyd, Alex Engar, and Ian Hogan are three business partners who help owners get clear on their finances, their teams, and what they actually want out of their business. Each week they bring real conversations, hard won lessons, and zero pretense. We talk money, people, growth, and the thing behind the thing, because the real question is never just "how do I hit my revenue goal." It's what do you actually want, and are you building toward it? If you're tired of advice that sounds good but doesn't fit your life, pull up a chair.

Episodes

  1. 17h ago

    Where Did All the Money Go? The 4 Financial Leaks Costing Business Owners Thousands

    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: 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.The job isn't done until the money lands — How $90,000 in earned revenue got stuck in accounts receivable.You can't price what you haven't measured — Why businesses can think they're making a 20% margin while actually making 5%.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.

  2. Aug 12

    The Shiny Object Trap: When “More” Is Actually Hurting Your Business

    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.

  3. Aug 5

    Would We Actually Buy This Business? Our Honest Take on 6 Industries

    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 paymentsSystems that improve cash flowThe psychology behind asking to get paidThe businesses they'd invest in and the ones they'd avoidWhat separates a good business from a great investment

  4. Jul 29

    Why More Revenue Won't Fix Your Cash Problem

    You're doing more revenue than you ever have. The P&L says you're profitable. And yet payroll week makes your stomach drop, tax season blindsides you, and you've quietly started stretching vendor terms from net 15 to net 45 to net 90. In episode two of Just Figuring It Out, Will, Alex, and Ian dig into one of the most common and least talked about problems in small business: being profitable on paper and broke in the bank. They cover: The three moments this problem usually surfaces (and why it's almost never on a random Tuesday)How cheap debt, EIDL money, and "easy" MCA offers act as a band-aid that hides the real issue for yearsWhy percentages matter more than dollar amounts as you scaleThe "profit valley" — the stage where you've outgrown a lean team but haven't grown big enough to cover the overheadThe hunter archetype: solving every financial problem with more activityWhat happens when your identity gets tied to year-over-year growthIan's "and then what?" exercise for anyone who feels compelled to take action immediately Plus, the guys pull back the curtain on their own scaling mistakes — including the decision to nearly triple ad spend, the hires they made because "the opportunity cost of not hiring was too high," and why they're grateful it didn't work out. This one leans more philosophical than technical. If you want the mechanics of why your P&L and your bank account disagree, that's a future episode. Want to go deeper? We host workshops most months. Join the email list at ceofinanceacademy.com and we'll let you know when the next one is.

  5. Jun 24

    Cash Flow Issues & Attracting Top Talent

    The podcast episode features a discussion among the founders of CEO Finance Academy, focusing on their journey, the challenges faced by small business owners, and the evolving landscape of talent acquisition and retention. The conversation delves into the importance of financial coaching, leadership, and the impact of personnel issues on businesses. The conversation covers the transition of a business coach to an owner, the importance of play budgets, the significance of understanding what you truly want in business, and the challenges of hiring and scaling a business. It also delves into the complexities of AI models and the need for practical usefulness. Takeaways Small business owners need support in navigating their finances and leadership challenges.The changing priorities of employees, including flexibility, learning opportunities, and meaningful work, are shaping the talent acquisition landscape. Transitioning from a business coach to an owner involves navigating partner buy-in and facilitating play budgets for creative employees.Understanding what you truly want in business is crucial, and it's important to avoid chasing unprofitable jobs for the sake of growth.The challenges of hiring and scaling a business involve considerations of cash flow, capacity, and reserves, as well as the need for practical usefulness in AI models. Chapters 00:00 Introduction and Podcast Overview06:47 Challenges in Talent Acquisition and Retention26:23 Challenges of Hiring and Scaling a Business38:32 Exploring AI Models and Practical Usefulness

  • 5 Episodes

About

Just Figuring It Out is a show for small business owners who are in it and navigating the messy, rewarding, confusing reality of building something that actually works. Will Boyd, Alex Engar, and Ian Hogan are three business partners who help owners get clear on their finances, their teams, and what they actually want out of their business. Each week they bring real conversations, hard won lessons, and zero pretense. We talk money, people, growth, and the thing behind the thing, because the real question is never just "how do I hit my revenue goal." It's what do you actually want, and are you building toward it? If you're tired of advice that sounds good but doesn't fit your life, pull up a chair.

Information

  • Creator
    Will Boyd, Alex Engar, & Ian Hogan
  • Years Active
    2026
  • Episodes
    5
  • Rating
    Clean
  • Copyright
    © 2026 Will Boyd, Alex Engar, & Ian Hogan
  • Show Website
    Just Figuring It Out