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For many public corporations, employee stock options have subject to tax in Canada in respect of the option benefit; and (v) the employer of the and designing any amendments to equity-based incentive programs which.

Once your company is confident it wants to pursue an IPO, it chooses investment bankers to manage the offering. These bankers will provide financial advice and analysis and introductions to potential buyers of your company's stock. Morgan Stanley and Goldman Sachs often act as lead underwriters for most high profile technology companies. The company's management team gets together with bankers, lawyers, and accountants to draft an initial prospectus, also known as the S This process can take months.

The initial S-1 is filed confidentially with the Securities and Exchange Commission SEC , which responds with comments the company must address. It can take months for the company and SEC to agree on the edits and disclosures that need to be added. Once both sides are in agreement, the "preliminary" registration statement is made public on the SEC's EDGAR database and a "red herring" prospectus is distributed to interested investors.

At this point, the prospectus only contains a potential range for the amount and pricing of the offering. Once the preliminary prospectus is made public, the company is ready to begin its "roadshow," where members of the executive team travel to major cities around the US and potentially even Europe and Asia to meet with potential investors. The roadshow typically takes weeks to build enough demand to create a successful IPO.

These days are jam packed, with management presenting to up to 10 unique investors each day before flying on to the next city. Once the roadshow is complete, there are only two things standing in the way of your company and an IPO: the "pricing" meeting with investment bankers and the SEC's final approval. The final steps happen in rapid succession: With investor feedback in hand, the investment bankers and company management meet to formally price the offering i. Once decided, a final registration statement with the SEC is then filed.

This usually happens the night before shares can officially be traded, so it's a pivotal moment for the company. The next morning, the SEC has to approve the final terms of the offering known as when the registration "goes effective". Once approved a few hours later, shares can be formally offered for sale. And with that, trading commences and your company is officially public. These days, companies are taking much longer to go public than they did in the past.

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That means employees have to wait much longer to recognize liquidity from their hard-earned equity. Softbank's recent secondary purchase of Uber employee shares was perhaps the largest of its kind. While this is a great opportunity for employees, it also poses a dilemma — is it worth selling now, or should you wait for a potential larger upside down the road with an IPO? All things being equal, you should probably hold onto to all of your stock if your employer's growth rate and margins are increasing.

But all things are not equal. If the IPO seems years away or management shows no interest in going public, you should also sell some stock — you might not get another chance. If your company stock represents the vast majority of your net worth, it might also make sense to take a little bit off the table and diversify your portfolio.

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It's also a good idea to cash in some of the equity if you have some expenses coming up or simply want to get further along with some of your other financial goals such as a down payment for a house. If you do sell early, keep in mind that your company's value could continue to grow significantly.

But don't let seller's remorse control your life. Once you make the decision to sell, don't look back. If that seems too difficult for you, determine how much stock you would like to sell upfront, and then commit to a schedule of selling the same amount of stock every quarter in the future. Through software, we automatically put your money to work with passive investing. We'll lower your tax bill with Tax-Loss Harvesting and keep investment costs low. Popular searches: college savings , retirement , tax-loss harvesting Tags: k , Plan , Burt Malkiel , career advice , direct indexing , diversification , employee compensation , ETFs , fees , financial advisors , financial planning , index funds , IPO , passive investing , rebalancing , selling plan , stock options , taxes , Vanguard.

Selling your stock The road to IPO, with all of its twists and turns, can feel very overwhelming. Selling your stock You might find selling to be a more emotional decision than you ever imagined: you're excited to cash in on all your hard work, but feel anxious about selling your shares and want to hold off for just the right moment.

Curious about selling private stock? Deciding when to sell The IPO is a bit of a hurry-up-and-wait, as employees usually can't sell their stock for up to days. Pro tip: Avoid decision paralysis by coming up with a plan ahead of time Post-IPO stock is known to be volatile, and in the heat of the moment you'll likely make a rash decision. Risk Besides the risk associated with holding a concentrated position , it's important to consider what level of risk you can take given your personal financial situation.

Taxes Depending on the type of equity you have, you may be able to make some optimizations to reduce your tax bill. Emotional wellbeing A good selling plan will minimize regret. Some selling plan options The optimal selling plan: Sell your stock swiftly! Have RSUs? Which selling plan is right for you?

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