In this Entrepreneurial Strategy Series event we explored the key financial and structural decisions founders face when starting and growing a business. Experts discussed entity selection, fundraising strategies, tax implications, and how to position a company for investors and long-term success. Attendees walked away with practical insights on building the right foundation for scaling a business.

Presented by the Entrepreneurial Strategy Series and Gearhart Law on February 26, 2026.

Key Takeaways:

• Choose the right entity: LLCs and S Corps work well for small or owner-operated businesses, while C Corps are preferred by investors.

• C Corps attract funding: Venture capital and institutional investors typically require a C Corp structure.

• Understand tax differences: LLCs and S Corps pass profits/losses to owners; C Corps pay corporate taxes at the entity level.

• File taxes even with losses: Losses can provide future tax benefits and should always be documented.

• Separate business finances: Maintain a business bank account and proper accounting from day one.

• Delaware is common for startups: It offers flexibility and familiarity for investors, though not always required.

• International business adds complexity: Operating abroad requires careful legal and tax planning.

• Operate professionally: Strong financial discipline and good advisors help build credibility with investors.

Our Speakers:

• Mitchell Fillet, Chairman & CEO of Fillet Capital Corp, Educator & Senior Executive: https://www.linkedin.com/in/professormitch-8735b9113/
• Robert Pesce, Managing Director in the Tax & Business Services division at CBIZ: https://www.linkedin.com/in/robert-pesce-cpa-413a57/
• David D. Postolski, Esq: event moderator, is a senior partner at Gearhart Law: https://gearhartlaw.com/team/david-postolski-esq/

This event is sponsored by Kickoff: The faster way to build credit. No credit checks, hidden fees, or interest. Helping credit builders score. Plans from $5/month. Visit https://plus.kikoff.com/

The Entrepreneurial Strategy Series is sponsored by Gearhart Law, a full service Intellectual Property firm specializing in Patent, Trademark and Copyright Law domestically and globally. Call us for a free consultation at 908-273-0700 or contact us through: https://gearhartlaw.com/

Chapters

• (00:00:00) - Entrepreneurial Strategy
• (00:01:07) - Two Experts on Startup Finance and Taxes
• (00:02:31) - Mitch McConnell on His Journey From Wall Street
• (00:04:16) - What's the Right Way to Start a Business? Sole proprietors
• (00:06:58) - What is a C-Corner?
• (00:08:07) - Are C-Corals Necessary for Starting a Business?
• (00:10:02) - What constitutes a Big Pile of Money?
• (00:11:29) - Can an Investor Invest in an LLC vs. a C Corp?
• (00:13:53) - Should You Consider a C Corp or an LLC?
• (00:17:01) - Do Delaware C Corporations Need to Be Delaware-based?
• (00:20:06) - Do US Businesses Need to Do Business in Another Country?
• (00:23:36) - Do American Citizens Need a US Citizenship to Do Business in the United
• (00:26:37) - Foreign Based Companies Trying to Do Business in the United States
• (00:29:20) - US C Corp vs. Foreign Business: Do They Matter?
• (00:32:36) - S corporation vs. C Corp
• (00:34:02) - C Corp vs S Corp
• (00:38:01) - Mitch McConnell: Startup Valuation
• (00:41:16) - Don't Go Down the Crazies in the Dot Com Boom
• (00:44:48) - $500,000 Investment
• (00:47:23) - Best Practices for Entrepreneurs in Financially
• (00:49:53) - Starting a Business: Best Practices for Taxation
• (00:50:57) - Best Practices for Business Starting in 2020
• (00:53:14) - Q & A
• (00:53:50) - Does SBIR Money Need to Be Paid?
• (00:54:57) - The Best Tax Structure for a Social Entrepreneurial Organization
• (00:56:44) - When to register a company in the United States?
• (01:00:15) - Financial Accounting Software for Small Businesses
• (01:02:38) - S Corp vs. C Corp: Best Place to Start a Business
• (01:08:28) - The Entrepreneurial Strategy Conference