In this episode of the Sales Hacker Podcast, we have Jonathan Friedman, CEO & Co Founder at Demostack. Join us for a conversation about how Jonathan’s company is helping reps tell the story of their companies more effectively and productively — Freeing up time to spend in more engaging conversations with their customers and prospects.
If you missed episode #196, check it out here: Cracking the Code to Ultra Large Deals with Jamal Reimer
What You’ll Learn
- The origin story that comes from a deep affinity w/ a specific problem
- Building Demostack in response to a lack of correct information
- The concept of a team, not a family
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Show Agenda and Timestamps
- About Jonathan Friedman & Demostack [1:51]
- From young entrepreneur to professional background [4:38]
- Key strategies to getting a company off the ground [11:25]
- How quickly categories can spring into existence [16:58]
- Building the right kind of culture [20:22]
- Why the demo is so messed up [25:00]
- Paying it forward [29:55]
About Jonathan Friedman & Demostack [1:51]
Sam Jacobs: Welcome to the Sales Hacker Podcast. Today we’ve got Jonathan Friedman, co-founder and CEO of Demodesk. They’re focused on helping reps tell the story of their companies more effectively, and spend time with their customers.
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We’re excited to have Jonathan Friedman on the show, he’s the co-founder/ CEO at Demostack, a platform that helps SaaS companies accelerate growth.
Previously, Jonathan was Head of Product at TripActions, a $7.25 billion corporate travel platform he led from an idea to a full-blown strategic business in 12 months. He’s passionate about building and scaling products at the cutting edge of technology and business. Jonathan, welcome to the show.
Jonathan Friedman: Thank you for having me.
Sam Jacobs: We like to start with is your baseball card, and help you pitch Demostack. Tell us about the company, how you started it, and what you do.
Jonathan Friedman: Demostack helps you win more deals by telling the story of your product and making it personalizable. It’s staging for software, not a clunky demo environment, but a platform built for showcasing. I saw how hard demoing is, became obsessed with it, and had to solve it for myself.
Sam Jacobs: Tell us where you are in your growth journey.
Jonathan Friedman: We’re 15 months old. We raised roughly $20 million overall in two rounds. I can remember when we were just two or three people trying to figure this out. We have our offices in R&D in Israel and Serbia. Our go-to-market is in the US. A fairly young company, but I feel like we’ve done a lot. In startup years, every year counts as seven.
From young entrepreneur to professional background [4:38]
Sam Jacobs: Tell us about the companies you built and your previous experience.
Jonathan Friedman: I’ve always been an entrepreneur, from the age of 14 or 15. I realized that I can determine my own fate.
I’m from Israel originally and army service is mandatory. I was a special investigator, a criminal investigator. After army service, I went to study in Holland. I did my bachelor’s, my master’s there. I started to open more digital businesses.
Entrepreneurship was always my passion, but I want to do high-tech entrepreneurship. I went back to Israel and started Reactful, which was in the conversion optimization space.
I’m technical in terms of how I think about the world, but I’m not an engineer. My skill set is being able to think, imagine, envision a concept. It’s about bringing energy to make it go live, bring it into market, think about it, strategically inform it.
I traveled in India, Nepal, Cambodia, to remember there’s a world outside Silicon Valley. I met the founders of TripActions and they asked me if I wanted to startup expense management. I came up with a pitch, which became TripActions Liquid.
Liquid is the E in T&E. It replaces expense management by letting you use virtual and physical cards to pay for anything you need and it’s automatically reconciled. It helps finance teams control and manage spend in a scalable way.
I left TripActions because I became obsessed with demoing. I saw the sales demo pain and realized this is a big thing. I left to build the Demostack. I enjoyed Liquid and it was my baby.
Key strategies to getting a company off the ground [11:25]
Sam Jacobs: What are the keys to being successful, when you’re getting a company off the ground?
Jonathan Friedman: The most important lesson is you’re looking for a huge signal. There are a million ideas out there and a lot of them are okay. But you’re looking for a pull from the market that’s crazy. When we started, we put a message out, does anyone have demo problems? We had so many replies and people wanting to talk to us. We had people already wanting to sign up
Those are the signals that you’re looking for. People excited, booking their next meeting with you, asking to email you about it. You’re looking for a big signal because startups are hard and you need perseverance. You don’t want to work where the signal is small. You want demand that’s on the surface where you bore a hole, and it explodes.
Once you find that, it’s all perseverance. Make sure your mental health is in check, as a founder, that’s a huge thing that is not enough addressed. Stay in the game. If you start with a strong signal and stay in the game, you will succeed.
Sam Jacobs: Are there words of wisdom you give people that are feeling that FOMO, they’re trying to turn something into a big signal when it’s clear that it is?
Jonathan Friedman: I believe entrepreneurship is a calling. You have little ability to resist and words of wisdom will not dissuade you.
Keep digging, keep talking, look for a big signal that surprises you. I understand restlessness. You want to open a business, but you’re going to be in this for the long haul.
You need to spend your time where it makes sense. Dig deeper for that signal. Talk to naysayers and hear what they have to say. Don’t always accept it, but hear them out with an open heart.
How quickly categories can spring into existence [16:58]
Sam Jacobs: The existence of competitors is confirmation that there’s a big opportunity. How do you view that?
Jonathan Friedman: Markets are always in a state of flux. When the time is ripe, it will happen. It’ll feel magical because it’s sudden. A market big enough, a signal big enough will attract enough Batmans to respond to it. There’s room for people to take different takes on it. It’s a long game.
Focus on what matters, focus on shipping good product, focus on getting customers in and making them happy. If you do that, you have a business. Don’t get caught up in all that Silicon Valley noise of crushing competition, all that stuff. It’s not the way you should think about the world. It’s about building something beautiful. Companies are hard to build. Build something that’s special.
Understand what competitors are doing, the marketing dynamics, what customers want, and deal with competition. Build the most unique company and have a vision that’s unique. Building a good company will get you to a good place.
Building the right kind of culture [20:22]
Sam Jacobs: Talk about building culture and the concept of being on a team versus being on a family.
Jonathan Friedman: In a company, you can fire someone. I don’t know how many family members you fired in your life, but you can not want to work with someone because they’re not a good fit for what you’re trying to build. If you come with a family mindset and you’re not being honest with employees and what you’re trying to do, you need to get there fast.
In terms of culture, there’s people that bring energy, they’re problem solvers. They see problems and they break them down even when it looks insane or improbable. You want people that can look a problem in the eye, engage, and think differently. You want the best people.
I always tell them, I work for you. If I hired you, I believe that you are the best at what you’re doing. I want you to execute it. If there are blockers, come to me, we’ll figure it out.
Why the demo is so messed up [25:00]
Sam Jacobs: Talk about why you can use Demostack to create intimate moments.
Jonathan Friedman: Digital products are complex. In order to showcase a product, you need to deal with that, and the only people that can are R&D.
Demos are just hard to do because your product is not built for showcasing. You can’t show production because you have data in there. You can’t give everyone access. The analytics go haywire and the finance team hates it.
I found myself building two products. This other product is built for showcasing, not expense management. It’s built for a different user. My go-to-market people, not my customers.
Showcasing is a different use case. It requires a different product. You could actually showcase the best version, celebrate the product you’re building.
Everyone was building a demo environment on the side, trying to hustle something. How would that accelerate go-to-market if you had something that was specialized in showcasing your product? That’s what we built.
Paying it forward [29:55]
Sam Jacobs: I love what you said about two different products, one’s the production product, one’s the showcasing product.
We like to pay it forward. What are the ideas, the authors, investors, mentors, books that inspire you and the people that created them?
Jonathan Friedman: On the entrepreneurship side, I listen to Elon Musk. He’s the best operator on the planet.
On a personal front or mental health, a good life coach or mentor is Sam Harris. I love his Waking Up app, which has also philosophy about life, moments, mindfulness. It’s built for people that want the deep essence but without disengaging your logical brain. You find a lot of value in the talks, the meditations, the moments he has there. He’s brought a lot of light into my life.
Write me at j@demostack.com. I think that’s the best way. Emails are things I read the most. So just j@demostack.com. Easy.
Sam’s Corner [33:30]
Sam Jacobs: Hey, everybody. Sam’s Corner. Love that conversation with Jonathan Friedman. Love an origin story that really comes from somebody’s deep affinity with a specific problem.
That’s why he ended up building Demostack, a post on a bulletin board that got flooded with responses and demands. New technologies tend to sprout up all over, roughly at the same time, as if something’s in the air, something bigger is at work, some broader universal energy. Demodesk is one of a few companies that are helping account reps tell their story more effectively.
We talked about this concept of a team, not a family. I understand the broad point, that employment is not unconditional. We’re trying to win. We want the best people, working hard to retain their place on the team.
Thank you for listening. If you want to get in touch with me, you can, sam@joinpavilion.com. Talk to you next time.
