I need to make a very important hire.

We only have one sales rep right now. And he’s doing over $100k /month in sales…

WITH only 4 months of sales experience.

So now we are going to hire our 2nd sales rep… and this person will have the opportunity to be a massive difference maker.

We have more inbound leads than we can handle. You won’t need to do any outbound. We just need a hard closer.

Must be based in SF

Must be high iq and eq

Must be able to earn trust with founders and VCs who have $100m+ in net worth

I’ve hired hundreds of sales reps in my career. If you’ve worked for me and are interested, please send me a Dm

Or if you have someone in mind please tag them in the comments 🙏

Alessandro Chesser

Stacking QSBS @ GetDynasty.com | ex Carta

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The richest founders I met at Carta  had one thing in common.

They set up trusts on Day 1. Before their shares were worth anything.

I saw thousands of cap tables over 8 years. Some founders were splitting their shares into trusts immediately when they incorporated, but I didn't understand why until I read a WSJ article about a famous founder who used trusts to get $120M in tax-free gains.

That was my aha moment.

Here's the trick: You have a $15M lifetime gift exemption. Meaning you can only give away $15M without paying gift taxes. Everything you gift over $15M is taxed at 40%. If you wait until your shares are valuable, you're going to burn your entire $15M gift exemption and it's much less likely you can get $100M+ in tax-free gains.

But if you do it Day 1 when your shares are worth nothing? You can gift millions of shares that later grow to $120M+, without touching your gift exemption.

I've had founders come to me days before their acquisition closed. Too late. They lost millions in taxes that could have been avoided.

Why isn't this taught as standard Day 1 advice? Because it used to cost 6 figures to set up and administer these kind of trusts. Lawyers charged $20K+ per trust and trust administrators charged $10k+ per year. Now Dynasty does it all for $1,500.

Did you set up trusts before or after your first fundraise? Drop your lawyer/adviser recs who actually educate founders on this.

Y Combinator teaches you how to get to $10M ARR. Nobody teaches you how to keep your $10M exit.

There are 10,000 blogs about growth hacking, CAC optimization, and sales playbooks.

Maybe 10 about founder tax optimization.

The ratio is literally 100 to 1.

Founders can tell you their CAC down to the penny. They optimize pipeline conversion rates. They A/B test landing pages obsessively.

Then they sell their company and lose 40% to taxes because nobody told them about QSBS stacking.

Here's the thing: VCs don't teach this because it's not relevant to them. After returning capital to LPs and splitting carry with other GPs, they rarely make more than $10M personally from a single investment.

So the basic QSBS exemption covers them. They don't need trust stacking.

But you as a founder? You can easily blow past $10M on an exit.

Owning 10% with proper QSBS stacking is economically similar to owning 15-16% without it in a high-tax state.

Same company. Same exit. Massively different outcome because of tax structure.

Yet nobody talks about it.

taplio

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