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Your First Startup Mistake Happens at Formation

The 5-step playbook investors wish every founder read.

Hey there! Welcome to the Carry Letter 👋 We’ll be exploring the latest financial news and discussing how it affects entrepreneurs like you. Plus, we'll share some awesome wealth creation insights from successful entrepreneurs.

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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.

2. Buy Your Founder Shares from the Company (for Pennies)

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.

3. Put Founder Shares on a Vesting Schedule

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

​Spare cash just sitting there?

​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

Want More?

Still can’t get enough? Well, we’ve got you covered!

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If you want more resources on building wealth as a solopreneur/entrepreneur, check these out:

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