With

Jonathan Friedman

Co-founder and CEO at Demostack

Jonathan Friedman is Co-Founder and CEO at Demostack, a platform that helps SaaS companies accelerate growth with better demos. Previously, Jonathan was Head of Product at TripActions, a $5B corporate travel platform, where he led TripActions Liquid from an idea to a full blown strategic business unit in 12 months. Before TripActions, Jonathan successfully brought multiple technology products to market with two exits. He’s passionate about building and scaling products at the cutting edge of technology and business.

1

What makes your founding team ideal?

Our founding team is very potent. We have a long history of working in the trenches together, and all three of us are experts in our respective fields.  

There is only a 10% overlap of what we do in terms of our day-to-day roles, so we each have our focus areas, which makes us highly productive and grants us a diverse set of specialties. 

Yet, since we’ve known each other so long we are natural teammates, trust one another, and collaborate incredibly well… It’s all heart and no ego.

2

What practice helps you become comfortable with the unknown?

Being an entrepreneur certainly requires a lot of risk-taking. I like to look at a lesson that I learned from Stoicism, which recommends that you envision the worst-case scenario and get comfortable with that. Then, when you’re comfortable with the worst actually happening, anything is better than that, so it’s actually an uphill battle wherever everything gets easier. With that mindset, it is much easier to dive headfirst into the unknown.

3

What is one habit or activity you adapted that makes you a better entrepreneur?

I think one of the most overlooked things for founders and entrepreneurs is physical exercise. It’s so important that I actually think VC’s should mandate it for founders at least twice per week. It gives you the energy you need, lowers stress levels, and makes sure you have time to disconnect and take care of your body. It’s essential to prevent burnout and gives you the stamina to keep fighting the good fight as an entrepreneur.

Then, when you’re comfortable with the worst actually happening, anything is better than that, so it’s actually an uphill battle wherever everything gets easier.

4

What book\ podcast\ resource every entrepreneur should read or listen to?

I’ve got two.  The First one is The Hard Things About Hard Things by Ben Horowitz. Ben gives a great account of the things that can happen along the way, how to overcome them, and what it takes to be successful in an entrepreneurial journey. 

The other is actually a YouTube video of Elon Musk giving a tour of the Starbase. He talks through one of the most complex operations on the planet and boils it down to something simple and understandable. It helps you think about your own work in a simple way.

5

What’s the Best Advice You’ve Ever Received?

As hard as it may be, when you get a compliment, just smile, say thank you, and shut up.

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