Alessandro Chesser

1.1K posts

Alessandro Chesser

Alessandro Chesser

@SandroChess

Helping founders get more QSBS @getdynasty_com | former vp sales at Carta (0-$300m arr)

San Francisco, CA Katılım Temmuz 2019
1.4K Takip Edilen714 Takipçiler
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Alessandro Chesser
Alessandro Chesser@SandroChess·
We spent 3 years working on this. What used to cost $100k+ and take months… now costs $1,500 and can be done in less than 24 hours. My cofounders and I all met at Carta in 2014. Kyle was the 1st engineer, I was the 1st sales hire, and Edison the 1st PM. We saw 1st hand that the richest people put their startup shares into trusts for family/friends and assumed they did it because they were just being generous. Well that might be the case, but we also found out that each trust was saving them millions in taxes. The richest people were paying zero taxes and the rest of us giving up nearly half our earnings. The system is completely broken - so we fixed it. Starting today, the earliest stage founders can set up the exact same trusts billionaires use, from day one of incorporation. Day 1 is the best time to put your shares in a trust, because the shares are worth zero on day 1. The less your shares are worth, the more taxes you can save. Check us out! @getdynasty_com And help us keep more hard earned money in the hands of founders and early employees.
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Jason ✨👾SaaStr.Ai✨ Lemkin
Let me summarize a few convos with founders from past 2 weeks: Personally, I won’t invest in an agentic “SaaS” / B2B company anymore no matter how good your AI and agent is … Unless it unlocks materially more budget than just traditional software budget. This may sounds obvious but I think a lot of folks get confused by it. It’s not enough today to use AI to make your B2B product 10x better than the old guys. That’s great and it WILL win you customers. The problem? That alone won’t win you incremental budget. You can steal Salesforce’s budget, or Workday’s, or whatever, but all the incremental budget is going to AI that either has radical ROI (gets you customers) or radical cost savings (don’t need half support team) or radical insights (100x better analytics -> insights -> ROI). Agentic ROI. Stealing budget just from other software is no longer enough. -> You have to have Agentic ROI, and where that shows up is much larger deal sizes than usual in your category. If deals are usually $20k in your category, but you can get $60k-$200k with AI, look, that’s the sign. If deals are usually $20k and you can get $20k but you can be incumbents with AI, that’s great. But it’s not enough. If your deal size isn’t at least 2x what your pre-AI competitors have, you don’t have Agentic Revenue, and you won’t scale to be bigger than them, and you may end up in … a 2x ARR trap at scale. No one wants that.
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Alessandro Chesser retweetledi
Vivek Sen
Vivek Sen@Vivek4real_·
PALANTIR CTO: “FOR $10 BILLION, ELON MUSK PUT 300 ROCKETS IN ORBIT.” “FOR $11 BILLION, THE STATE OF CALIFORNIA HAS BUILT 1,600 FEET OF ELEVATED RAIL... WITH NO RAIL.”
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Alessandro Chesser
Alessandro Chesser@SandroChess·
I was featured in the @WSJ this week. They asked me about abusive qsbs stacking strategies. Most people think qsbs stacking is a tax loophole. It’s not. Hard coded tax law makes it possible. These are the 3 qsbs stacking strategies the IRS will most likely view as abusive: 1. Creating multiple trusts for the same person and claiming multiple exemptions for them. One person is only supposed to get one QSBS exemption. You shouldn’t be able to get multiple exemptions for the same person just because you create multiple trusts for them. 2. Creating trusts for yourself. QSBS stacking exists so you can give shares away to others. Not so you can give shares to yourself in a trust and claim additional exemptions for them. 3. Creating trusts too close to an exit. I see this every single day. Acquisition conversations heat up and then founders race to create trusts. This is a red flag. You should be creating trusts early, far ahead of exit conversations. The above strategies are loopholes. QSBS stacking by itself, when done correctly, is not. Link to article in comments.
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Howard Lindzon
Howard Lindzon@howardlindzon·
The outside of my cut off finger looks better than the xray …
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GEOFF 🧠💸
GEOFF 🧠💸@geoffwoo·
i remember this trip. i had a call with scott and zach to invest in the @cognition series A @ $2b while they were en route to visit this kid’s parents. @ScottWu46 is a savage and a winner. hard to compete against or bet against someone who goes this hard
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Austin Hughes
Austin Hughes@austinh___·
We built Claude for outbound sellers. AEs & SDRs can harness GTM engineering through chat across 40+ data sources, no technical skills required. We’ve had 57,548 queries in our first few weeks of beta, growing 45% w/w. The teams winning outbound in 2026 are already on it. Self-serve now live here: app.unifygtm.com/?screen_hint=s…
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Alessandro Chesser
Alessandro Chesser@SandroChess·
Founder who stacked 4 qsbs trusts before getting a term sheet
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Alessandro Chesser
Alessandro Chesser@SandroChess·
@kelvinbuildss most founders will lose 37% of their exit to state and federal capital gains tax. that's 37% they could keep if they knew the hacks that the ultra-wealthy have been using for decades. we're making those strategies available to everyone. getdynasty.com
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Kelvin Celso
Kelvin Celso@kelvinbuildss·
Founders/builders: what problem does your startup solve?
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Mark Lou
Mark Lou@markproduct·
Hey founders, Looking to connect with people building in: - Saas - Tech - Automation - Ai tools - Web apps - Developer tools Drop what you're working on below 👇
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Santosh
Santosh@santoshstack·
Founders, Which metric matters most to you? • MRR • Profit • Active users • Retention • Growth rate
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Alessandro Chesser
Alessandro Chesser@SandroChess·
@boardyai we multiply founders' QSBS exemptions to save them millions on their exit... probably should be talking to everyone here
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Boardy
Boardy@boardyai·
Founders, tell me what you do. I'll tell you who you should be talking to.
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Rashka
Rashka@rdbuilds7·
It’s Time to promote your startup founders Drop your project URL 👇
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Alessandro Chesser
Alessandro Chesser@SandroChess·
@DanielSmidstrup we multiply founders' QSBS exemption using trusts to minimize capital gains tax when they exit. its the same strategy the Roblox CEO used to exit $120m tax free. we productized it for founders so we do it at scale.
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Daniel Smidstrup
Daniel Smidstrup@DanielSmidstrup·
sell me your startup in two words max.
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Alessandro Chesser
Alessandro Chesser@SandroChess·
@athcanft the amount of solo founders that we have signed on is insane! if they're signing up with us, they're projecting significant exits, its inspiring to see
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Will
Will@athcanft·
solo founder + personal brand is the new meta anyone can build anything with AI now you don’t need a dev, a lawyer or an accountant anymore we have claude look at levelsio, marclou, jackfriks, maubauron, ernesto lopez, alexcooldev… the list goes on they live their lives on their own terms, no VCs, no one stressing them with deadlines or quarterly projections they wake up, work on what they want, and stack serious $$$ if they can do it, you can do it
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Henrick Johansson
Henrick Johansson@compliantvc·
Euro founder after raising €15k in a Series A and securing a 4-figure contract with SAP
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Alessandro Chesser
Alessandro Chesser@SandroChess·
@inferredbylisa it's true that most startups fail, but you have to bet on yourself. those who believe they will fail and those who believe they will succeed are both usually right. we help founders who believe they will succeed.
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Lisa
Lisa@inferredbylisa·
Whenever I meet engineers out in the wild, I always ask if they ever thought about starting something of their own. Last night this guy told me that he had no desire to be a startup founder because his dad had been an entrepreneur all his life and he never “made it” he just failed over and over again and they really struggled. You don’t hear these stories going viral on twitter.
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Wiki Milczyńska, MD
Wiki Milczyńska, MD@w_milczynska·
I've now seen 50 screenshots of the Cursor founder in people's DMs and I'm convinced the real product was the outbound. man ran a one-man SDR team against the entire tech industry and closed it at $60B
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