Resources for insight and
inspiration
Guides
Insights
Startup Compensation Strategy: Best Practices and Pitfalls for Founders
When your startup is strapped for cash and focused on growth, compensation can feel like a puzzle. But how you pay yourself and your team sends a signal - to investors, regulators, and employees. Done wrong, it can cause legal headaches, tax issues, and cultural tension. Here's how to navigate early-stage compensation the smart way.
Legal Essentials: Employment Law Fundamentals for Startup Founders
When you’re building a startup, employment law may not be your first priority - but it should be close to the top of your list. Mistakes in hiring, classifying, compensating, or terminating employees can trigger lawsuits, fines, and reputational damage. Here’s a practical guide to the employment law issues every founder should get right from day one.
Terms of Service: Why Your Startup Needs Them—Now
If you run a website, app, or platform, your Terms of Service (TOS) are more than just boilerplate - they’re your shield. They limit your liability, set ground rules for users, and give you power to enforce your policies. Skip this, and you open the door to chaos.
FAQs
Open allWhat is a typical discount rate on a convertible note?
Discounts usually range from 15% to 25%, rewarding early investors with more favorable share pricing in the next round.
Do convertible notes always convert into equity?
Most notes are designed to convert, but if no qualifying financing occurs by maturity, the company may need to repay the note or negotiate an extension.
What is the difference between a convertible note and a SAFE?
A convertible note is debt that converts into equity with interest and maturity terms. A SAFE (Simple Agreement for Future Equity) is not debt and has no maturity or interest, making it simpler but sometimes less investor-friendly.
Can a startup recover from a down round?
Yes. Many high-profile companies rebounded from down rounds to reach IPO or successful exits. The determining factor is how effectively leadership uses the new capital to achieve sustainable growth milestones.
How should founders communicate a down round to stakeholders?
Transparency is key. Frame the round as a strategic move to secure runway and strengthen the company, rather than a setback. Clear messaging helps maintain confidence among employees, customers, and partners.
What protections do investors have in a down round?
Most prior investors have anti-dilution protections in their agreements. Depending on whether it’s a full ratchet or weighted average clause, existing investors may be shielded from dilution, which can further reduce founder and employee equity.
How does a down round affect founders and employees?
The primary impact is equity dilution - shares may lose paper value, and employee options can go “underwater.” To counter this, companies often implement option pool refreshes or repricing programs to maintain team motivation and retention.
Does a down round mean my startup is failing?
Not necessarily. A down round often reflects market conditions or a recalibration of expectations, rather than a death sentence. Many companies use down rounds to reset and build stronger fundamentals.
How common are down rounds in startups?
They are more common than many founders realize, especially during market downturns or periods when investor sentiment shifts from growth to profitability. Even well-known unicorns have gone through down rounds before achieving long-term success.
Should I hire outside advisors for due diligence preparation?
Yes, in most cases. Securities counsel, accountants, and IP attorneys can help you spot and fix issues before investors do. It’s often less costly to prepare in advance than to renegotiate under pressure later.
Do all investors perform the same level of due diligence?
No. Angels often conduct lighter checks, focusing on the team and vision, while VCs and strategic acquirers require comprehensive financial, legal, and technical verification. The later the stage, the more rigorous the process.
What’s the most common reason startups stumble during due diligence?
The biggest issues are disorganized records (messy cap tables, missing contracts) and unresolved legal/IP questions. These red flags create delays, valuation pressure, or even deal collapse.
How long does the due diligence process usually take?
For early-stage rounds, due diligence can take 2–4 weeks if your documentation is organized. Later-stage or acquisition-level diligence may take 2–3 months due to deeper financial, technical, and legal reviews.
How much can an individual non-accredited investor put in?
Limits depend on income/net worth: typically a few thousand dollars annually under Reg CF.
Will raising from non-accredited investors hurt my chances with VCs later?
It depends. If managed well, it can signal traction and community buy-in. Poorly structured rounds, however, may complicate future fundraising.