Good Morning!

1. Feature: ChatGPT 5 vs Grok vs Perplexity for Small Business Use (4 min)

2. From the Archive:

   • How to Get an SBA Loan in 2025—Even With Tougher Rules

   • Side Hustle to Scalable SMB: Keep It Lean or Ramp It Up?

3. Dear TCoL: Perhaps the Greatest Tax Loophole for SMBs has Exclusions

Use today to clear the clutter and start your week with purpose.

-TCoL

Missed our last feature article? Working Through the Never-Ending To-Do List of an SMB Owner

AI tools have come a long way in the past year. What once felt experimental now powers real work in small businesses. The question isn’t whether to use AI anymore. It’s which one will actually help your team.

Below is a plainspoken guide to three leading tools: ChatGPT 5, Grok, and Perplexity. You’ll see what each does best, where each struggles, how much they cost, and which kinds of businesses benefit most.

What each one is

ChatGPT 5
OpenAI released GPT-5 on August 7, 2025, as the new default model in ChatGPT. It shows major gains in reasoning and accuracy and includes a “thinking mode” that helps it explain its steps more clearly. ChatGPT is available in several plans, from free to enterprise. OpenAI reports almost seven hundred million weekly users worldwide, which makes it the most widely adopted AI assistant today.

Grok
Grok is built by xAI and connects directly with X, formerly Twitter. Grok 4 launched in July 2025, followed by Grok 4 Fast in September. Both versions focus on speed, accuracy, and real-time awareness. Anyone with an X account can now use Grok with usage caps. It’s also available through paid tiers like SuperGrok, a public API, and business options including Microsoft Azure AI Foundry.

Perplexity
Perplexity is a search-driven assistant that always cites its sources. It combines conversational answers with direct links to where information came from. Its Comet browser, released to all users in October 2025, builds this capability directly into web searches. Perplexity offers free access plus two enterprise tiers called Pro and Max.

Strengths

ChatGPT 5
It is the most versatile of the three. You can draft emails, summarize reports, edit contracts, plan marketing campaigns, and analyze spreadsheets all in one place. Its built-in features such as Projects, Tasks, and file tools make it useful for daily business work without extra setup.

Grok
It focuses on real-time answers. If you ask about breaking news, current prices, or recent events, Grok checks live information. Its Fast version aims to deliver the same quality as larger models but at lower cost per use. For developers and enterprise users, Grok integrates with systems like Azure and includes strong security features such as single sign-on and SOC 2 compliance.

Perplexity
It excels at research. Every answer includes links and citations, which helps you confirm facts quickly. For small teams doing competitive analysis or content research, that transparency saves time. Enterprise Max adds unlimited “Labs” experiments, priority support, and even short video generation each month. The free Comet browser lets anyone use its core features without paying.

Weaknesses

ChatGPT 5
Its web access is optional, not automatic. If you want sources and citations, you must ask for them. Some of its strongest features, like Projects and custom GPTs, only work within OpenAI’s system, so switching later can take effort.

Grok
Its setup is less straightforward. Consumer access depends on X subscription levels, while business and API plans are separate. Pricing information for those options is still maturing. Documentation is improving but newer than what OpenAI or Perplexity offer.

Perplexity
It’s designed mainly for finding and confirming information, not for running projects or automating workflows. If you want a single place to manage tasks or files, you’ll need to pair it with another tool. Its most advanced features sit behind the higher-priced Max plan.

What it costs

ChatGPT
Free users can access a limited GPT-5 model. The Plus plan costs $20 per user per month. Pro costs $200 per month. Business plans start at $25 per seat per month if paid annually, or $30 monthly. Enterprise pricing is custom.

Grok
Free users can now try the latest model with usage limits. X Premium Plus includes Grok access for about $40 per month. The SuperGrok Heavy plan is around $300 per month for serious users. Developers can buy API access at about three dollars per one million input tokens and fifteen dollars per one million output tokens. Business deployments can use Azure’s marketplace.

Perplexity
Pro costs $20 per user per month. Enterprise Pro is $40 per month or $400 per year. Enterprise Max is $325 per month or $3,250 per year and includes unlimited Labs use, fifteen monthly videos, and premium support. The Comet browser is free.

Which fits your business

Professional services
If you run a law firm, accounting practice, or consulting agency, start with ChatGPT 5. It handles drafting, summarizing, and analysis efficiently. Add Perplexity for quick fact-checked research; use Grok if you need current-event insights for clients.

Ecommerce and retail
Your main need is speed — product descriptions, customer replies, and ad ideas. ChatGPT 5 covers all three. Use Perplexity to monitor competitors and find new suppliers. If your brand interacts heavily on X, Grok helps track trends and respond in real time.

Real estate and local services
Start with Perplexity. Its search-driven answers help you build local market briefs, find zoning data, and prepare outreach lists. Use ChatGPT 5 for templates and polished messages. Try Grok for live updates and local news that affects listings.

Media and content businesses
Writers, editors, and podcasters can rely on ChatGPT 5 for drafting and revision. Use Perplexity for background facts and cited sources. Use Grok for trend spotting and quick coverage ideas.

Software startups
Developers will appreciate ChatGPT 5 for coding help and documentation. Add Perplexity for technical research that needs links to official references. Use Grok when speed and low cost per query matter, especially with the Fast models or API.

Security and data control

ChatGPT Business and Enterprise include SSO, admin controls, SOC 2 Type II, ISO certifications, and an option to keep your data out of OpenAI’s training sets.

Grok for Business provides SOC 2, single sign-on, SCIM, role-based access, and audit tools, with deployment through Azure AI Foundry for enterprise needs.

Perplexity Enterprise offers SOC 2 Type II, organization-level file controls, and a promise not to train on customer data.

Whichever tool you choose, confirm your company’s data retention and privacy settings before rolling it out to staff.

How to decide

If your team creates content, analyzes data, and wants one general-purpose AI that does almost everything, start with ChatGPT 5. Upgrade to Pro or Business if you hit daily limits or need performance guarantees.

If your team spends hours researching and needs every answer backed by sources, choose Perplexity Enterprise Pro. Move up to Max if you use it heavily or need its video and Labs features.

If your team lives on X or wants to test an AI with lower cost per use, try Grok. The free plan is enough to get a feel for its speed and tone. Businesses with developers can explore the API or Azure integration.

The bottom line

All three tools can help a small business. The best one depends on what you do every day.

ChatGPT 5 is the strongest all-around assistant for writing, analysis, and internal workflows.
Perplexity is the best choice for research and verification, especially now that Comet is free.
Grok is the best for real-time work and cost-efficient queries when your team needs live information.

The smartest move is to test each tool for thirty days. Give your team three specific tasks each week and measure the results: time saved, quality of output, and cost per use. The data will tell you which one truly fits your business.

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Dear TCoL: Perhaps the Greatest Tax Loophole for SMBs has Exclusions

Question: I am trying to decide between an LLC or a C corp for my new business. I want to use the small business tax exemption under section 1202. I’ve read about a number of exclusions. I have a software company. Would my business qualify?

Answer: Not sure without additional information because IRS Code Section 1202 is complex and fact-specific, but it can be extraordinarily rewarding if your small business qualifies. To dive deeper, read our recent article: What Businesses Should Consider Using a C Corp Instead of an LLC?

We did, however, find an IRS Private Letter Ruling that might help. First, for everyone’s benefit, if your new C corp qualifies under 1202, here is a summary of the benefits:

Under 1202, non-corporate holders of qualified small business stock (QSBS) may exclude a portion of their gain on sale from gross income, subject to strict requirements. For QSBS acquired after September 27, 2010, and held more than five years, the exclusion is 100% — the entire gain, up to certain limits — and that gain is also excluded from alternative minimum tax calculations.

Under the new One Big Beautiful Bill, QSBS issued after July 4, 2025, enjoys a raised per-issuer cap of $15 million (or 10× basis). It also introduces stepped exclusions: 50% after 3 years, 75% after 4 years, and 100% after 5 years. The issuing company must be a domestic C corporation whose gross assets do not exceed the threshold at issuance and that uses at least 80% of its assets in an active qualified business for substantially all of the holder’s ownership period.

However, not all C corps and their owners are allowed to take advantage of 1202. The exceptions are found under subsection (e) of 1202:

Section 1202(e) excludes certain trades or businesses from qualifying as a “qualified trade or business.” These include service-based fields such as health, law, engineering, architecture, accounting, actuarial science, performing arts, consulting, athletics, financial services, brokerage, or any activity where success depends mainly on individual reputation or skill.

Also excluded are banking, insurance, financing, leasing, investing, and similar enterprises; farming (including timber operations); businesses eligible for percentage-depletion deductions such as oil, gas, and mining; and hotel, restaurant, or hospitality operations.

A recent IRS private letter rulings adds clarity and might help you. In PLR 202319013 (https://www.irs.gov/pub/irs-wd/202319013.pdf), the IRS found that an enterprise software company qualified because its core value came from intellectual property, not personal service. While private rulings apply only to the requester, they show how the IRS interprets the line between qualified and excluded activities.

Our suggestion would be to consult an attorney or CPA with 1202 experience and let them carefully determine if your business qualifies. If it does, congratulations; the tax benefits are remarkable.

Have an interesting business question and need a free bit of advice? Send your question to [email protected]. No confidential info, please!