Entrepreneur-VC, dad x 3, competitive sailor, invests in US and Israel, passionate about building companies and working with non-assholes

Joined April 2009
11 Photos and videos
Jacques Benkoski retweeted
Real VCs don’t always know SAFEs and they don’t offer adequate protections. I strongly discourage founders from using SAFEs in most case (there are exceptions) and standardize on NVCA standard docs (also available on the web). The middle ground is seriesseed.com docs.

I’m ‘leading’ a deal and using a standard YC Safe. One of the on-the-fence VCs keeps asking me to see the Safe before he decides if his fund will invest. And I keep directing him to the YC website… It’s the standard YC Safe! What do you need to see bro?? 🤷🏼‍♀️
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Jacques Benkoski retweeted
1 Apr 2023
Fascinated by the phenomenon of late stage funds reaching out to early stage managers. We know you only do two things: (1) chase "obvious" late stage deals and (2) ruin early stage companies by coming in too early and breaking everything with too much capital and bad advice.
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Jacques Benkoski retweeted
I spend WAY too much time helping founders to unlearn what they get from "brand name" accelerators who are giving them horrible advice.
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Agreed !
I came to same conclusion 👇
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Jacques Benkoski retweeted
2008 was chaotic…there were new crises, rules, etc nearly daily. I can’t imagine what that would have been like with a juiced-up rumor mill of assholes looking for attention layered on top of it.
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Welcome aboard @mdgarratt ! Proud to call you my partner and to be working with you and your amazing experience and network to invest in great companies.
USVP Doubles Down on Enterprise Franchise with Addition of Matt Garratt ow.ly/zZH550N0AaE
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Pathetic. Such a good game till they played chicken at the end
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Jacques Benkoski retweeted
My professional writing coach while I was a freelance journalist taught me - it’s not your job to stop when there’s nothing left to add. It’s you job to stop when there’s nothing left to remove. Writing short is much harder than writing long. Great guidance for decks too.
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Jacques Benkoski retweeted
This remains one of my favorite investor notes of all time. Thanks @LeadEdgeCapital.
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Jacques Benkoski retweeted
It seems like the solution to this modern information overload hellscape we inhabit is to simple stop caring about as much as possible.
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It was an illusion that momentum chasing was the job. As the tide recedes those businesses that were the product of that motion will prove fragile and/or uneconomical. It was always about investing.
All-in pod nailed a largely unspoken anxiety in vc right now. As we move from *momentum chasing* to *investing*, firms & individuals are realizing the fitness function they optimized for the last decade is massively different than the fitness function they’ll need for the next
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Jacques Benkoski retweeted
Eventually all investors realize that it wasn’t their tweets, or PR mentions, or awards, or popularity that mattered. Just their investments and returns on them. But some take a while to internalize that. Advising a friend early in VC career who is wondering about all this.
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Jacques Benkoski retweeted
Oh man, people are really worked up about a Chinese balloon conducting surveillance over the U.S...wait'll they hear about an app called TikTok.
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Jacques Benkoski retweeted
"So yes I made billions pumping my SPACs, being a storyteller and posting one-pagers for 15 months during the pandemic. Now I talk about how markets were frothy, valuations didn't make sense, and companies need to toughen up on my pod and at conferences."
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As easy capital ends, recent VCs and founders will go back to the basic pillar of startup Darwinism: push through yourself, figure things out, grow from each experience. The VC role is to help you think, plan and analyze, not do in your stead as that actually is fake progress
Founders should not expect their investors to introduce them to customers. It's not their job, and they are usually not very good at it.
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META move is the public equivalent of a recap. You remove shares and the value of the remaining shares goes up. If you look at the multiplier between the size of the buy back and the increase in valuation, it’s nowhere near 200x, more like 5x ?
Meta is up $100B in market cap and interest rates are down today, time to bring back those 200x ARR deals and big founder secondaries - it was all a bad dream
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Jacques Benkoski retweeted
The mind is so powerful that it has the ability to override all your senses when you want to confirm your existing beliefs.
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That 25% slice is almost always a critical piece of the pie to entice new and existing investors as well as people that need to rededicate several years of their lives to have a go at keeping going. If the terms are attractive, early investors are welcome to double down.
2 Feb 2023
2/Wiping out early angel investors & founders is entirely unnecessary, even in the case of recapping a struggling company Carving out 25% of the cap table for previous founders, investors, & employees--even if it's unlikely they will get a win--is the right thing to do, IMO.
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Jacques Benkoski retweeted
The best salespeople I've met are also the best listeners I know.
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