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Your First Startup Mistake Happens at Formation
The 5-step playbook investors wish every founder read.
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Setting up a tech company is already a high-voltage roller-coaster—no need to add self-inflicted loops. Nail these five early-stage moves and you’ll spare yourself (and your investors) expensive clean-up work later.
1. Start as a C-Corporation—Not Later, Now
Venture investors assume you’re a Delaware C-Corp because it lets them hold preferred shares, grants you unlimited shareholders, and—crucially—keeps you eligible for the 100 % QSBS capital-gains exclusion (up to the greater of $10 million or 10× basis). Converting from an LLC or S-Corp after you raise is messy and may reset that QSBS clock.
Pro tip: Congress is debating tweaks to QSBS in 2025, but the benefit is still alive and well. Lock it in while you can.
At incorporation, purchase your stock directly from the corporation—usually at $0.0001–$0.001 per share. That single invoice timestamps your holding period for QSBS and 83(b) purposes and proves you paid for the equity. Future diligence teams will thank you.
Even if the founding team is just you and your best friend, impose vesting (standard: four years with a one-year cliff). Should a co-founder leave in month nine, the company can repurchase the unvested stock instead of lugging around dead weight on the cap table. Investors view this as non-negotiable.
4. File Your 83(b) Election—30-Day Shot Clock
The IRS gives you exactly 30 days from the stock-purchase date to file. Do it, and you’re taxed on today’s near-zero value; skip it, and you’ll owe ordinary income tax as each tranche vests at future (hopefully sky-high) prices. There are no mulligans.
5. Separate Business & Personal Money on Day One
Open a dedicated business bank account and run every company dollar through it—no Venmoing yourself for “random supplies.” If you cover expenses personally, record them as a short-term loan at a reasonable interest rate and pay it back when you close your first round. Clean books speed up fundraising and keep the IRS happy.
Quick-Glance Checklist
Move | Why It Matters | When To Do It |
---|---|---|
Incorporate as C-Corp | QSBS + investor-friendly structure | Before you raise a dime |
Buy founder shares | Starts QSBS clock, proof of ownership | At formation |
Set vesting (4 yrs/1-yr cliff) | Protects cap table, aligns incentives | At formation or before first round |
File 83(b) election | Avoid future tax spikes | Within 30 days of share grant |
Separate finances | Audit-ready books, legal hygiene | Immediately |
Up Next
We’re unpacking QSBS, 409A valuations, and early-stage tax hacks in depth during our Personal Finance for Startup Founders live session.
Subscribers get first dibs on the live session and the replay. đź‘€
Stay tuned, and in the meantime, forward this checklist to the co-founder who still hasn’t opened the business checking account.
Building a company is hard but your paperwork shouldn’t be.
What’s Happening at Carry Lab?
Here’s what you can expect in the coming weeks
See the full list of events here. ⏰
How to Maximize Your Earnings on Cash
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​In this 30-minute lightning session you’ll learn how to squeeze the highest after‑tax yield out of uninvested cash:
​- Money‑Market Funds 101 – what they are, how they stay liquid, and why yields keep rising.
​- Tax‑Smart Variants – funds that can sidestep state or federal taxes.
​- Tax‑Equivalent Yield – the quick formula to compare apples to apples.
​- Picking the Winner – a simple filter for the fund that leaves you with the most money in your pocket.
​- One‑Click on Carry – see how our platform automates the whole play for you.
Personal Finance for Startup Founders
We'll cover:
​​​How startup founders should think about their personal money matters - how much to pay themselves, should they raise capital for their business etc.
​​​How to compensate and hire their early team
​​​Strategies to complete their first round of fundraising
​​​How to understand QSBS - the biggest tax break for startup founders and how to prepare the company for it
​​​Founder liquidity - secondaries and exiting the business
​​​Plus, a live Q&A with Ankur and the team
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If you want more resources on building wealth as a solopreneur/entrepreneur, check these out:
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