# Financial Advisor Tech Founders Connecticut > ISO/NSO planning, equity concentration, and liquidity event financial planning for Connecticut tech founders and executives. # Wealth Planning for Connecticut Tech Founders Building a Financial Plan Around Equity [Schedule a Conversation](https://westportwealthpartners.com/contact/) ## You Have Been Building the Company. Now Build a Plan for the Wealth Inside It. You have been heads down building. The company has been the financial plan: the equity stake, the upside, the reason the long hours made sense. And that has worked. You've gotten to a point where the equity is real and significant. But you've never had time to build a personal financial plan around it. That changes when a liquidity event approaches, or arrives, or when you look at the concentration of your personal balance sheet and realize that almost everything you own is correlated to a single company's performance. Nicholas DiFalco, APMA® CEPA® and Matthew T. Streif, CEPA® at Westport Wealth Partners work with Connecticut tech founders and executives who are at exactly this inflection point. The planning challenge is specific: your largest asset is equity. It may be illiquid. It has complex tax treatment. And it needs to become the foundation of a personal financial plan, not remain the entirety of one. ## Talk to an Advisor Who Can Translate Your Equity Into a Real Financial Plan No obligation. One conversation. We start with the full picture: equity, tax, estate, and what you actually need. [Schedule a Conversation](https://westportwealthpartners.com/contact/) ## Managing Equity Concentration Your Biggest Financial Risk Most tech founders and startup executives have their most significant asset in a single company. If you are a co-founder with a meaningful ownership stake, or a senior executive who has accumulated equity through years of vesting, your personal balance sheet likely looks like a highly concentrated single-stock position. Concentration risk having too much of your net worth correlated to a single company, is one of the highest-risk financial situations a person can be in. The upside is clear. The downside is that if the company's value declines, your personal financial security can decline with it in a way that a diversified investor would never experience. Nicholas DiFalco's personal balance sheet framework addresses this directly. It starts by mapping every asset (vested equity, unvested equity, liquid investments, real estate, retirement accounts) against your income needs, timeline, and actual risk tolerance. Not the risk tolerance you described on a questionnaire. The one that holds when you are watching a company you helped build lose half its value in a correction. For public company executives, a systematic sell-and-diversify plan, potentially implemented through a 10b5-1 trading plan that allows you to sell on a predetermined schedule during blackout periods, is often the appropriate approach. For pre-liquidity founders, the plan involves building a liquid portfolio incrementally as secondary transactions or partial liquidity events occur. ## Stock Option Planning ISO vs. NSO and Why the Timing Matters If you have stock options, ISOs (Incentive Stock Options) or NSOs (Non-Qualified Stock Options), the timing and structure of your exercises has significant tax implications. This is one of the highest-impact planning areas for tech founders and executives, and one of the most commonly deferred. ISOs (Incentive Stock Options) NSOs (Non-Qualified Stock Options) 83(b) Elections ISOs (Incentive Stock Options) ISOs receive favorable tax treatment, gains are taxed at long-term capital gains rates if the shares are held for the required period, but ISO exercises can trigger Alternative Minimum Tax (AMT). The AMT implications of exercising a large ISO position can be substantial in certain situations. Coordinate with a CPA who has ISO/AMT experience well before exercising. NSOs (Non-Qualified Stock Options) NSO exercises create ordinary income equal to the spread between the exercise price and the fair market value at exercise. This income is subject to payroll taxes and ordinary income tax rates. Timing NSO exercises to years of lower ordinary income can reduce the tax burden, coordinate with your CPA. 83(b) Elections Founders with unvested founder shares or early employees who exercise options before vesting have the option to file an 83(b) election within 30 days of acquiring the shares. This election starts the capital gains holding period earlier. Missing the 30-day window is an irrevocable mistake, there are no extensions. Raymond James does not provide tax or legal services. All stock option decisions require coordination with a CPA with specific experience in equity compensation tax planning. ## When the Liquidity Event Happens Building Your Financial Plan from the Proceeds You've worked for years toward a liquidity event: an acquisition, an IPO, or a large secondary transaction. When it arrives, the financial planning challenge is real: you have a large amount of capital that needs a plan, and the plan needs to be built quickly because the tax clock is already running. The sequence matters: Before the Event Immediately After Building the Long-term Portfolio Before the Event The financial plan should already be drafted. Understanding the expected after-tax proceeds, building the income plan, coordinating with the CPA on deal structure decisions that affect tax treatment, these are things that happen before the close, not after. Immediately After Tax coordination is urgent. How the proceeds are invested, whether any Qualified Opportunity Zone strategy is applicable, whether charitable giving vehicles should be established before the end of the tax year, all require immediate action. Building the Long-term Portfolio Many founders and executives have never had a diversified personal investment portfolio because all of their financial energy has been in the company. Building one from scratch (establishing asset allocation, risk parameters, income planning, and an investment strategy) takes time to do thoughtfully. Westport Wealth Partners builds this plan alongside your CPA and attorney. ## For Tech Executives with RSUs and Equity Compensation Not every tech financial planning client is a founder. Employed executives at technology companies (particularly those with significant RSU vesting schedules, deferred compensation arrangements, and 401(k) balances) face a distinct version of the equity concentration problem. RSU vesting creates a recurring tax event: shares vest, create ordinary income, and need an immediate decision: hold or sell? Accumulating RSUs year after year without a systematic plan builds concentration in the employer's stock. For executives at large public tech companies, this can grow into a multimillion-dollar single-stock position over a career. A systematic equity management plan (coordinating RSU vesting with a diversification schedule, year-end tax planning, and a long-term portfolio construction strategy) is the financial planning response. This plan requires close coordination with your CPA and awareness of any insider trading restrictions or pre-clearance requirements. ## Frequently Asked Questions for Technology Founders and Executives ### Do you work with pre-liquidity founders? Yes. Building a financial plan before a liquidity event is significantly better than building one after. Pre-liquidity planning covers equity modeling, tax scenario analysis for the expected event, building a liquid portfolio alongside the equity, and estate planning with concentrated equity. The earlier this work begins, the more options are available. ### I have ISOs I have not exercised. How do I think about this? ISO exercise decisions are complex and highly dependent on your personal income, AMT position, company stock price, and exit timeline. The tax implications can be substantial, both from AMT and from the potential benefit of starting the long-term capital gains clock. This is one of the highest-impact financial decisions a tech executive can make, and it requires a CPA with ISO/AMT expertise. We coordinate the financial planning piece, including modeling the impact on your overall financial plan, but the tax decision belongs to your CPA. ### I just received proceeds from selling my company. Where do I start? With a full discovery conversation. We need to understand the total picture: the amount, the tax treatment, any installment or earnout arrangements, your current financial plan, income needs, and goals. From there we build a sequenced plan: tax coordination first, then investment strategy, then estate planning update. Many founders find this moment overwhelming precisely because they have never had to make these decisions before. That's exactly the situation we're built for. ### I'm a public company executive with trading restrictions. Can you work within those? Yes. Westport Wealth Partners is familiar with the pre-clearance requirements, blackout periods, and Section 16 insider trading restrictions common at publicly traded technology companies. We can coordinate with your firm's compliance department and help structure a 10b5-1 plan for systematic diversification within the rules. We do not provide securities compliance advice, always follow your employer's compliance policies. ### My equity is almost entirely in one company. How do I diversify without creating a large tax bill? There is no way to diversify a concentrated equity position without some tax cost: but the tax cost can be managed over time through a systematic approach, charitable giving strategies, and coordinated timing. This is a multi-year planning exercise, not a single transaction. Raymond James does not provide tax advice, we coordinate the financial plan with your CPA to build the most efficient path available. ### I have never had time to think about estate planning. Is that a problem? Concentrated equity creates specific estate planning considerations that are different from a diversified portfolio. If the equity is in a private company, valuation for estate purposes, family gifting strategies, and irrevocable trust structures may all be relevant. If the company has IPO'd or been acquired, the planning challenge is different but equally time-sensitive. The earlier estate planning is addressed, the more options are available. ### Do I need to live in Connecticut to work with you? Westport Wealth Partners primarily serves clients in Fairfield County, Connecticut and Westchester County, New York. We also work with clients in other states where our advisors are properly registered. For the right client, we work nationally on business exit and liquidity event planning engagements. ## Talk to an Advisor Who Can Translate Your Equity Into a Real Financial Plan 19 Ludlow Rd, Suite 202, Westport, CT 06880 | 203.298.1834 [Schedule a Conversation](https://westportwealthpartners.com/contact/)