What are the best business tax books for someone starting multiple businesses?

I've been checking out some business tax guides from my local library, mainly the NOLO ones, but I'm not sure if these are the best resources out there. I'm planning to launch a couple different business ventures in the next year and really need to get a handle on how taxes work for each business type. I'm clueless about which tax structures would be most advantageous for the different businesses I want to start (one service-based and one selling products online). Has anyone read any really helpful books specifically about business taxation that breaks things down simply? Looking for recommendations that explain the differences between sole proprietorships, LLCs, S-corps, etc. and their tax implications. I'm definitely a beginner when it comes to business tax stuff, so something that doesn't assume I already know everything would be ideal!

0 coins

18 comments

Yara Abboud

•8M

I'm a small business accountant, and I highly recommend "Tax Savvy for Small Business" (also by NOLO, but it's one of their best). It covers all the business structures you mentioned and explains the tax advantages of each in plain English. Another excellent resource is "Small Business Taxes: Your Complete Guide" by J.K. Lasser. It's updated annually to reflect current tax laws and gives practical examples that make complex concepts easier to understand. For someone starting multiple businesses, I'd also suggest "Multiple Streams of Income: How to Generate a Lifetime of Unlimited Wealth" by Robert Allen. While not strictly a tax book, it does cover tax strategies for different business models. Remember that tax laws change frequently, so make sure you're getting current editions of these books, especially for the 2025 tax year.

0 coins

Keisha Williams

•8M

After spending hours trying to understand business tax structures for my two startups, I discovered this amazing AI tool called taxr.ai (https://taxr.ai) that actually saved me from having to read through multiple books. It analyzes tax documents and explains complex tax concepts in simple language. I uploaded some sample business formation docs I was considering and it broke down the tax implications of each one for my specific situation. It was like having a tax expert explain everything to me personally. The tool even showed me which deductions I'd likely qualify for with each business structure I was considering.

0 coins

Keisha Williams

•8M

It absolutely helps with multiple business types! I'm actually running a service business and recently added a product component, and the tool helped me understand whether to keep them as one entity or separate them. It provided clear pros and cons for each approach. The accuracy has been impressive in my experience. It's trained on actual tax code and regulations, and gets updated whenever tax laws change. That said, I still run complex decisions by my accountant, but taxr.ai helps me understand the basics so I can ask better questions when I do meet with professionals.

0 coins

Amina Sy

•8M

I was initially skeptical about taxr.ai as mentioned above, but decided to try it when I was absolutely drowning in tax research for my new businesses. It was seriously eye-opening! The tool explained business expense categories for my specific industry that I had no idea I could deduct. What convinced me was when it analyzed the draft operating agreement from my attorney and flagged several tax issues I hadn't considered. Ended up saving me a bunch in potential future taxes by suggesting a different profit distribution structure. Now I'm using it to plan my quarterly estimated payments too. Definitely worth checking out if you're starting multiple businesses!

0 coins

Oliver Fischer

•8M

If you're struggling to get specific answers about your business tax situation, I'd actually recommend talking directly with an IRS agent. After trying for WEEKS to get through to the IRS business tax helpline, I found this service called Claimyr (https://claimyr.com) that got me connected to an actual IRS rep in under 20 minutes. They have this demo showing how it works: https://youtu.be/_kiP6q8DX5c I had specific questions about how to handle startup expenses for my new business ventures that I couldn't find clear answers to in any books. The IRS agent was surprisingly helpful and walked me through exactly how to categorize and deduct them correctly.

0 coins

Oliver Fischer

•8M

It works by using a system that continually redials and navigates the IRS phone tree until it gets a human, then it calls you and connects you. It's basically doing the hold waiting for you so you don't have to sit there listening to the hold music for hours. I was extremely skeptical too, but I was desperate after trying for days to get through about a specific business expense question. The service monitors the IRS phone lines and calls when wait times are statistically lower. Nothing magical about it - just smart technology that saves you from the frustration of waiting on hold.

0 coins

NebulaNomad

•8M

I need to eat my words from my comment above. After another failed attempt to reach the IRS about my business tax questions, I broke down and tried Claimyr out of pure frustration. I was connected to an IRS agent in about 15 minutes after weeks of failed attempts on my own. The agent answered my specific questions about how to handle inventory for my new e-commerce business while also running my consulting practice. Got clarification on several deductions I wasn't sure about. The time saved was absolutely worth it - I would have spent another week trying to get through on my own. Sometimes you have to admit when you're wrong, and I was definitely wrong about this service!

0 coins

Javier Garcia

•8M

The podcasts do regular update episodes whenever significant tax law changes happen, which is super helpful. They did comprehensive episodes on all the Tax Cuts and Jobs Act changes and more recently on the Inflation Reduction Act impacts on businesses. Kohler's book has a whole chapter dedicated to online and digital businesses, covering things like sales tax nexus issues for selling across state lines, deducting website expenses, and tax implications of digital products versus physical goods. The newer editions have expanded this section significantly.

0 coins