Who Will Actually Do the Work?
Ask who will lead the matter, who will handle day-to-day questions, how work is staffed, and whether the senior lawyer you meet will remain directly involved.
Choosing Counsel
How to Compare Westchester Startup Counsel
If you are considering a Westchester lawyer or law firm for startup, venture capital, corporate transaction, or outside general counsel work, the useful question is not which firm has the longest service list. It is which lawyer and working model best fit the company, transaction, and decisions in front of you.
Jason Gershenson advises founders, startups, venture-backed companies, investors, and funds on financings, commercial contracts, governance, equity matters, M&A, investor and fund matters, and recurring outside general counsel work. His practice is built around senior-level involvement, practical judgment, and the pace of startup and growth-company matters.
What to Compare Before Choosing Counsel
Does Counsel Understand Venture Mechanics?
Startup work is not just general corporate work. SAFEs, preferred stock rounds, side letters, pro rata rights, cap tables, investor dynamics, and financing process management require specialized judgment.
Can Counsel Operate as an Outside GC?
The right fit may need to cover contracts, governance, equity, hiring, investor requests, financing, diligence, and strategic decisions without treating every question as an isolated project.
Will Advice Match the Company's Pace?
Founders need careful legal work, but they also need clear priorities, practical risk assessment, responsiveness, and an understanding of what the business is trying to accomplish.
Is the Staffing and Fee Model a Fit?
Compare billing structure, staffing leverage, expected turnaround, communication style, and whether the proposed team makes economic sense for the company's stage and needs.
Why Founders and Investors Talk to Jason
- More than a decade advising venture capital funds, startups, and high-growth companies.
- Company-side and investor-side experience in multimillion-dollar venture financings.
- Outside general counsel work across contracts, governance, equity, financings, investor matters, and strategic transactions.
- Founder and operator experience from building and exiting a venture-backed technology company.
- A transaction-focused practice serving clients across the U.S. and internationally.
When the Choice Usually Matters Most
Fit becomes especially important when a financing is moving, the cap table or governance record needs cleanup, a customer contract carries real operating risk, an investor request affects leverage, or the company needs a regular legal point person but is not ready to hire a full-time general counsel.
Those matters call for more than document production. They require someone who can identify the actual decision, explain the tradeoffs, manage the process, and keep the legal work aligned with the business objective.
FAQ
What should a founder compare when choosing startup counsel?
Compare who will actually lead the work, relevant startup and venture experience, responsiveness, staffing, fee structure, communication style, and whether counsel understands both the legal documents and the business decision.
Why does direct senior-lawyer involvement matter?
Direct involvement can reduce handoffs, keep advice consistent, and help counsel understand how contracts, governance, financings, equity, and investor matters fit together across the business.
What kinds of startup matters does Jason handle?
Common matters include formation, founder and equity arrangements, venture financings, commercial contracts, governance, investor communications, cap table cleanup, M&A preparation, and recurring outside general counsel support.
Does Jason work only with Westchester companies?
No. Jason is based in New York and works with founders, companies, investors, and funds across the U.S. and internationally.
Contact
See whether the fit makes sense.
For potential matters, referral conversations, or professional questions, email Jason or schedule an intro.
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