Drew Prentice

The $0-$5m CFO looks different than the $5m-$50m CFO. And by "CFO" I refer to whoever is sought out for financial help. Below $5m, unless raising capital, the need is primarily accounting-based. A cash-based system may be adequate with the limited resources. Technical questions are often tax-related. These types of companies do well having a staff accountant + tax firm or outsourcing everything to a CAS firm. Above $5m, there may be more complexity. Accrual basis provides greater insight into business economics. There may be debt covenants to manage. There are also greater resources. This size may add a controller-level leader on a full-time or fractional basis, and even layer on fractional FP&A or CFO resources. The $0-$5m cares about operational efficiency and taxes. The $5-$50m cares about business insights and access to capital. Of course I'm generalizing here. It depends on so much. But in the average this is about right.

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In my opinion, the days of selling Tax Strategies as information or "How to" Tax plans for premium prices are numbered. If you use the following ChatGPT prompt structure, it will generate pretty much what you would pay for. "You are a (insert: type of taxpayer such as RE investor or business owner), what are the top tax strategies to use to minimize my taxes? Please provide a list of tax strategies with how to qualify for each, the documentation needed and pitfalls to look out for." For more detail you can ask about each specific tax strategy that is generated from the above prompt or from the list attached here. "You are a (insert: type of taxpayer such as RE investor or business owner), how do you qualify for the (insert: tax strategy), what documentation do I need and what are things to look out for? Let me know if the results are sufficient or if there are flaws!

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I’m excited to share that Onside Accounting are partnering with Multiplier Holdings. AI is already reshaping our industry and over the next few years I believe it will transform it completely. We want to be leading that transformation, not chasing it. Multiplier is an AI-native professional services company founded by Noah Pepper, who previously sold a business to Twitter and went on to scale Stripe’s Asia business to more than 600 people. His team includes world-class engineers and product leaders from Stripe, Google, Facebook, Dropbox and ScaleAI. They recently closed a Series A, with significant backing from Ribbit Capital and Lightspeed – Two of the best investors in the world. Our goal is to build custom technology designed for Onside. Technology that will surprise and excite our clients, raise quality, deepen trust and elevate our service. Technology that will free our team from repetitive work so they can focus on meaningful work and maintaining a healthy work–life balance. This partnership protects what we’ve built and opens the door to something far bigger than we could achieve alone. I remain CEO of Onside for the very long term, and I have never felt more excited or more challenged than today!

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💭 “𝐈 𝐝𝐢𝐝𝐧’𝐭 𝐧𝐞𝐞𝐝 𝐚 𝐥𝐨𝐚𝐧—𝐮𝐧𝐭𝐢𝐥 𝐈 𝐫𝐞𝐚𝐥𝐢𝐳𝐞𝐝 𝐈 𝐚𝐥𝐫𝐞𝐚𝐝𝐲 𝐡𝐚𝐝 𝐨𝐧𝐞.” Sounds odd? That’s the power (and the trap) of Pre-Approved Overdrafts (ODs). As a CA, I often see business owners celebrate when their bank offers a pre-approved OD. “It’s a safety net.” “It improves working capital flow.” “It’s available instantly.” ✅ Yes, it's flexible. ✅ Yes, interest is charged only on usage. ✅ And yes, it looks good on paper. But here’s what many miss 👇 🔸 Pre-approved doesn’t mean free. That credit line sitting idle? It’s still part of your overall exposure. It impacts your credit report. 🔸 Not planning its use? That’s a red flag. ODs should complement cash flow strategy, not replace it. 🔸 Banks monitor your usage behavior. Too much OD reliance? Risk flags go up when you actually need credit the most. 💡 My Takeaway as a CA: Pre-approved OD is not a financial booster—it’s a discipline test. The smarter you are with when and how you use it, the stronger your financial foundation becomes. Use OD like a spare tire: ✅ Don’t drive on it every day. ✅ Check its pressure often. ✅ Know when to replace it with a more sustainable vehicle—like a structured loan or equity support. If you’re a founder, CFO, or finance manager, treat pre-approved OD as a tool, not a trophy. 🔁 Have you ever used a pre-approved OD facility? Did it help or hurt your finances long-term? Let’s decode it in the comments. #Overdraft #FinanceTips #CAInsights #CashFlowMatters #PreApprovedOD #WorkingCapital #CreditDiscipline #LinkedInFinance

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You’re getting ripped off on tax prep fees. Imagine your S-Corp is ready to branch out, and you want to invest in a new business. → You could just set up another LLC or S-Corp, whichever is right. → But there’s a smarter play: the Q-Sub (Qualified Subchapter S Subsidiary). Here’s why: → 100% ownership, single tax return → When your S-Corp owns 100% of a subsidiary, it can elect Q-Sub status. → The Q-Sub files nothing separately – all income, deductions, and credits flow through to the parent S-Corp’s return, save on tax prep fees & less paperwork. → Just check Question 10 on Schedule B of your 1120-S and include all Q-Sub financials on the parent return. → This will pay off if you are in a Q-Sub friendly state, & you have good books, & you have multiple legit qualifying S-Corps, run through one parent S-Corp filing. But not all states play nice → Some states let you consolidate like the IRS. Others want their piece, requiring separate returns. → Friendly States (no separate Q-Sub tax return): FL, TX, SD, WY, WA, NV, AK, MT. → Not So Friendly States (separate returns required): NY, NJ, CA, IL, MA, MN, TN, WI. So before you jump into a new venture, know your state’s rules – or it could cost you. Because here’s the thing: → Setting up a Q-Sub is just the beginning. → If you really want to layer your tax advantages, protect assets, and create a whole new stream of deductible income, there’s an even smarter move almost no one talks about. → In the next post, I’ll show you how self-renting your own property through a layered entity strategy can unlock powerful deductions and keep your money working for you, & not the IRS. Stay tuned. ♻️ RESHARE this post to help others avoid unnecessary tax traps!

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