Awesome People List - Ep 24

Hot negotiation tips, operators, product fun

Hi founders and fellow VC Friends!

Each week we deliver one awesome person to your inbox. These are the people you need to know—the marketers, sales gurus, engineers, ops wizzes— who give your startup superpowers 🚀. The best part is, everyone is hireable on an interim basis. With no further ado, today we’ve got: 

  1. Person of the Week (and lots of negotiation tips!) 

  2. FT Gem 

  3. PS. Product Goodies 

Please meet Craig, Your Negotiation Consultant

I met Craig a few years ago via Tommy Leep, a fellow investor and climate advocate. Craig is a startup negotiation consultant. Did you know this was a thing?! I def didn’t 😎. Turns out that any time you have an important deal — think hiring, partnerships, acquisitions, fundraising, co-founder agreements — you can hire Craig to help. 

Recently he helped a co-founder negotiate a life-changing exit from their own startup and another founder get a 280% increase on an 8-figure acquisition offer 📈. Pretty impressive!

Over the course of his career, he’s worked with professors at Duke and Wharton. He’s a trained mediator and spent the last 18 months working the Suicide Hotline in SF.  Talk about high-pressure negotiation 🙏. One little known fact about Craig - he’s also a singer-songwriter and occasionally performs at small venues around SF 🙌. 

He's trusted by clients at Airbnb, Youtube, Facebook, Stripe, Cloudflare, Lyft, and many more startups and venture firms. Last year he started negotiation workshops for women and minority groups at Airbnb, Plaid and Zenefits 💜.

You can hire him to help negotiate:

  • Comp packages for high-value employees

  • Relationships between founders and investors

  • Partnerships deals 

  • Co-founder agreements and “tough situations” 

In addition to the nitty-gritty, he can also create a framework for negotiation for your HR team and host negotiation workshops.

Let me know if you want an intro!

He graciously shared 4 negotiation tips with us here (I’m taking notes!).  

“If I say X, they’ll likely say Y. And then we’ll probably end up at Z.” 

This isn’t strategic. When you push a little harder you often do better, but sometimes at the cost of the relationship. 

Instead, try to understand what makes your counterpart tick. A number of years ago I worked with Dan Ariely, the author of Predictably Irrational and a professor of behavioral economics at Duke. His research found that we make decisions emotionally and then rationalize them later to make them feel like a conscious choice. 

For example: When faced with a picture and story of one starving child in Africa, we happily donate. With two children, we donate less, and if it’s a broad statistic, hardly at all. That’s because a single child alone is the saddest. People will say that they donated based on the cause. But their stated reason (the cause) and their actual reason (pulled heartstrings) are different. 

When you're negotiating, focus on the emotional part of your counterpart’s brain, which acts unconsciously. Find ways to empathize with them, make them feel good and keep them talking. It’s a strategy we use on the suicide and crisis hotlines, it works in hostage negotiation, and it works in business.

Don’t try to argue solely with data 

Most people prepare for a negotiation (if they prepare at all) by thinking about what they want and the reasons they should get it. Many prepare solely by gathering data and getting advice. 

While data can inform you, trying to argue with it is almost always a mistake. We know from our current political scene that people can take the exact same data and come up with wildly different perspectives. When I worked with Stuart Diamond, a professor of negotiation at Wharton, he used to say “If you argue with logic, you’ll be right more than you’ll be effective.” Again, it all comes back to the emotional state of your counterpart. 

Your secret weapon: the right questions

Asking questions is a critical way to gather information, which can then be used to better empathize with your counterpart. People don’t like being interrogated, so ask questions that make them feel good, rather than digging holes in their reasoning. Here are some quick tips: 

  1. Ask open-ended questions. These give you the chance to gather more info and they come across as less threatening. Not all open-ended questions are equal, use 'how' and 'what' questions. Avoid 'why', which makes people defensive.

  2. Let them have the power. Ask for advice. I like the phrases "Help me understand..." or "What would your advice be on..." This allows you to gain information while making them feel in control. 

  3. End your thoughts with a question. Plan how to end your thoughts. If you don’t, you’ll run on and leak information. Use endpoints like "is that in line with your thinking?" or "how does that sound?" to hand the reins back to your counterpart. 

Try to get to ‘No.’

We inherently think we want to hear the other side say ‘Yes,’ but the art of negotiation is about hearing ‘No.’

For example, if I make a proposal for a partnership with a setup fee of $50K and you immediately agree to it…. What did I learn? Nothing.  Instead, I want to ask enough questions and get enough rapport going that I can lob over a soft proposal of $85K, which you’ll likely say ‘no,’ to and then I can start to figure out what your limits are. 

The key is to handle ‘no’ gracefully, without fracturing the relationship. This type of approach is a human-centered one. Testing for boundaries is a lot harder to do over email and text, than over the phone. People get attached to what is written down. Stick to logistics over email and prepare. Then get on the phone to talk over proposals and see how the other side reacts. 

Let me know if you want an intro to Craig and I’ll connect you via email!  

FT Gem - Chief of Staff or Venture Associate 

Josh and I met through an initiative he runs to connect female fund managers with people who invest in funds. I was immediately impressed with his hustle, go-getter attitude, and ability to run with things. He’s considering his next move and is interested in a Chief of Staff or ops role at a seed-series A company, or an associate or principal role at a VC.

That’s a wrap! Let me know if you want an intro to Craig or Josh and I’ll make it happen. Also, feel free to share musings on the product finds below ✨.

Stay awesome, 

Julia Lipton

Founder of Awesome People List

Founder of Awesome People Ventures

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PS Goodies

Looking to run better remote teams? Story of my life… Here are a couple of tools that I’ve been playing with. If you like to geek out on products, I’d love to hear your thoughts — what you like, what you don’t 🙏.

Standups is great for remote async standups and team updates. They make it easy to leave video and audio notes for your team. The mobile app is the real MVP. Def did a standup from bed, not even going to lie… 😂


Remotion helps you feel more connected to your team remotely. You can see who’s working on what, who’s available to chat, and quickly jump into video chats. Still in beta, but pretty cool!


Icebreaker is an awesome way to host all-hands, meaningfully one-on-ones, and recreate the office happy hour online. Be sure to check out the templates. Their customer demos are legit fun.

I hope you enjoy these extra goodies and have an awesome week (pun intended) 🎉.