Working the Wait: Making the Most of a Delayed IPO

When you’re waiting for a liquidity event — whether an IPO, merger or tender offer — time can feel like it’s standing still. Stock options sit on paper, plans stay paused and every market headline hits differently.

We get it. We work with many people navigating that same uncertain in-between. One moment you’re hopeful, then you’re anxious about what comes next. And as we shared in our recent Aspiriant webinar, “Planning for Delayed Liquidity Events,” an IPO delay doesn’t have to derail your progress.

In fact, it can open the door to powerful planning opportunities that may strengthen your financial foundation when the event finally arrives. If you’re preparing for your company’s public offering, explore our Aspiriant IPO Planning Guide for a deeper look at how to approach liquidity events from start to finish.

How to use an IPO delay to your advantage

Clarify your cash flow and near-term goals

The first step in any liquidity event planning process is clarity. When the timing of a liquidity event shifts, take time to revisit your near-term cash needs.

This helps answer questions like:

• How much liquidity do you really need right now?
• Which goals can wait until after your IPO or secondary sale?
• Would participating in a tender offer or a short-term lending arrangement make sense — what might you be giving up in terms of share appreciation by not waiting and/or are you adding unnecessary risk?

If the goal is, say, a near-term home purchase, a tender offer might make sense. But for other goals, patience may prove more valuable. The right path depends on your priorities, time horizon and company policies. It is important to look at these decisions in the full context of your life and financial plans. This kind of pre-IPO wealth planning helps align short-term needs with long-term goals — keeping your liquidity decisions grounded in strategy, not timing.

Explore tax and equity compensation strategies that require time

When liquidity is delayed, the silver lining is time — time to plan, document and optimize your tax position.

Qualified Small Business Stock (QSBS) is one of the most underutilized tax benefits we see. If your company qualifies, you may be able to exclude up to $10–15 million in capital gains when you eventually sell your shares, depending on current law. But eligibility requires meeting strict criteria, which can only be confirmed before the event.

This waiting period is the perfect moment to:

• Verify QSBS status with your wealth manager and CPA.
• Review share documentation to confirm eligibility.
• Avoid actions — like certain transfers or restructurings — that could jeopardize your exclusion.

For those who don’t qualify for QSBS, the delay may still allow time to implement tax-loss harvesting or diversification strategies for concentrated positions. These techniques form part of a broader equity compensation strategy that can help optimize tax outcomes before your liquidity event.

What should I do if my company’s IPO is delayed?

Use this waiting period to reassess goals, confirm QSBS eligibility and prepare a tax-efficient liquidity plan. Small adjustments now can make a significant impact later.

Refresh your estate plan before valuations spike

Pre-IPO valuations tend to be more stable — and often lower — than post-IPO prices. That’s why you could use a delay to revisit estate planning.

If your liquidity event happens in a year or two, this can be an ideal time to:

• Update your estate documents and beneficiary designations.
• Consider gifting private shares to a trust or charitable foundation before valuations climb.
• Explore strategies to move future appreciation out of your taxable estate.

When markets are volatile and IPO valuations fluctuate, planning early gives you flexibility later.

Planning for the big day: When your IPO finally happens

Avoid emotional pitfalls

When the IPO finally happens, the focus shifts from waiting to deciding. This transition can be emotional and expensive if handled impulsively.

Two of the most common pitfalls we see are anchoring and paralysis:

• Anchoring happens when you fixate on a peak stock price and hesitate to sell below it.
• Paralysis sets in when a sudden influx of cash feels overwhelming.

Build a disciplined post-IPO selling plan

A pre-set selling strategy can help you stay objective — and protect against the emotional pitfalls we mentioned above. By planning ahead, you reduce the risk of anchoring to a single stock price or feeling paralyzed once shares become liquid.

Work with your advisor to determine:

• What portion of shares to sell at vesting, lockup expiration and over time. (Helps prevent anchoring.) Setting up a structured stock-sale schedule can take the emotion out of the decision and keep you from fixating on short-term price peaks.
• How to allocate proceeds across diversified investments. (Addresses paralysis.) Having a clear plan for where your proceeds will go helps you act with confidence instead of hesitating once the funds arrive.
• When and how to set aside funds for tax obligations and future goals. (Reduces both anchoring and paralysis.) Mapping this out early gives you clarity and control, so tax or cash-flow surprises don’t cloud your judgment.

This kind of planning transforms a liquidity event from a reactive moment into a proactive milestone — one guided by your long-term goals rather than short-term market noise.

Turning IPO waiting time into planning time

An IPO delay doesn’t mean you’ve lost momentum. It means you have an opportunity to refine your plan.

Here’s what we recommend using this time for:

1. Reassess your short-term goals and liquidity needs.
2. Verify QSBS eligibility and other tax-efficient opportunities.
3. Diversify concentrated stock where possible.
4. Update estate planning documents and gifting strategies.
5. Build a post-IPO selling plan that reflects your goals and risk tolerance.

These pre-IPO planning steps can help you enter your liquidity event with greater clarity, confidence and control — key markers of successful IPO planning.

Further exploration: webinars and related resources

If you’re navigating a delayed IPO or preparing for a liquidity event, these additional Aspiriant resources expand on many of the ideas we discussed here:

• 5 Expensive Mistakes to Avoid Before and After an IPO — In this video webinar, our team highlights common errors around IPO timing, taxes and lockup decisions that can cost shareholders dearly.
• 5 Expensive Mistakes to Avoid Before and After a Liquidity Event — A companion fathom blog that explores similar themes for mergers, acquisition, and tender offers.

Both pair well with our IPO Planning Guide and Equity Compensation Guide for a fuller picture of what to expect — and how to plan — before, during and after a major financial event.

Continue your IPO planning journey

A liquidity event is one of the biggest financial milestones you’ll ever experience — and the waiting period can be one of the most powerful times to plan.

If you’re unsure how to navigate your company’s delayed IPO or want to refine your pre-IPO wealth planning, Aspiriant’s advisors can help you turn uncertainty into opportunity. Our team partners with executives and employees to design customized strategies for equity compensation, liquidity events and long-term wealth planning. If you’re looking for guidance, talk with us.

Explore our guides to take the next step:

Aspiriant IPO Planning Guide — A comprehensive overview of what to expect before, during and after an IPO.

Equity Compensation Guide — Understand how your stock options, Restricted Stock Units (RSUs) and ownership fit into your broader financial strategy.