Xoogler.co: Fireside Chat with Jonathan Sadow

Jon’s Background

Xoogler Jonathan (Jon) Sadow is a co-founder and the current Chief Growth Officer (GCO) of Scoop, a mobile application for commuters looking to save money by carpooling. Jon co-founded the company with his brother Rob Sadow after the two developed a survey to ask what were the biggest frustrations in people’s personal lives and professional lives; Traffic was the answer to both. The two decided to tackle this problem together by founding Scoop. They both agreed Rob was more operational, so he would fit the CEO position well, and Jon would focus on growth and marketing.

Setting the Scene

Xoogler Paul McDonald introduced Jon for the fireside chat and moderated questions from other Xooglers in the crowd. The two worked together at Google, and Paul helped Jon transition from ad sales into product management. Their friendly relationship set a comfortable tone for the conversation, on top of the fact that Jon was taking the call from his children’s playroom, the only place where he could find a quiet place to give the talk.

Both Jon and Paul have since left Google, and both are co-founders of their own successful start-ups. Jon described the career change with this: “I finally got an idea good enough that I felt comfortable to leave Google”. He finally ran a pilot that investors could get on board with, and that was when he knew Scoop would work. Jon was also happy to tell stories of the early days of Scoop, the realities of fundraising for a start-up, and how healthy company culture is key to surviving the pandemic as a transportation company.

The Early Days at Scoop: Brotherly Love and Fundraising

The relationship between Jon and Rob, his brother and co-founder, was obviously a big influence on the company culture from the beginning. Jon was able to laugh about learning the hard way that when you go into business with family members you need to separate professional conversations from other personal matters. The trick to having a healthy relationship with any co-founder you also have a personal relationship with, Jon says, is clearly agreeing on roles and responsibilities and continuously and publicly respecting the authority of the CEO. Jon continued by reminding us that co-founder isn’t a job title. It took some time, but he learned which conversations in which to remain involved, and which roles he can trust to manage themselves.

For anyone in the start-up space, you understand the importance of fundraising. Here are some tips Jon shared from his personal experience raising funds for Scoop:

• Fundraising is a science, not an art: there is a right and a wrong way to fundraise, so you better do your research beforehand.
• Feedback: pitch your idea to as many people and as early as possible. Most ideas don’t get far for a reason, so listen to all feedback to reflect on your idea honestly.
• Create a narrative: numbers without context are meaningless. Your pitch to VC firms and other outside investors needs to be a balancing act between displaying data and showing passion. Stay true to your vision, and make sure it is clear and specific. Effectively weaving the two into an engaging story will often be the deciding factor.
• Pitch the lines: Progress, Traction, Accomplishments, Goals.
• Read the room: Don’t waste your time pitching to VCs with different worldviews. It’s a waste of time, and after some practice you can usually sense whether or not a potential investor is interested early on in the discussion. Cut your losses, and find a new VC to pitch to.
• How can you tell if a successful pitch is going to result in investment? Well, for the most part, you can’t. Oftentimes the pitch may go well, but you cannot control how your company is re-communicated to other decision-makers in the organization. An engaging narrative has a better chance of being re-communicated in the way originally presented.
• You’ll know if you have a good idea sooner or later: if your peers continue to insist on introducing you to a VC firm, you probably have something.

With secured funding, Scoop grew into what it is today: a trailblazer in the transportation industry.

Creating a Lasting Culture

Paul began to shift the conversation into talking about the company culture, and how it has persisted during the difficult years like this one. Jon reminded us that though good culture is not a requirement for a successful business, it has always been highly valuable to him and his brother. Their philosophy is to take bets on the people they hire, and reward aggressively. The strengths and weaknesses of the culture are reflected in the company. It’s hard to hide a toxic culture.

Jon reminded everyone that putting the company values on the wall lives up to the cliche. Values are created by what we say, how we act, and how we respectfully encourage each other. The wall reads:

Give a good push

“We put them on the wall because we live these values and believe in them, not because we think putting them on the wall will make people believe them”.

Jon continued by talking about how he tackled the business challenges of the pandemic, along with some general advice for successfully running a company during turbulent times. One lesson is to always have cash in the bank and plan to use it wisely, but the reality is a lot of what can happen is based on luck. There is always risk and you can’t plan for everything. Success comes from the ability to pivot, rotate, and be prepared to change.

The question quickly became: “How long do we work on a product that won’t really generate value until people can physically go back to the office?” This pivot in the fundamental business plan shifted focus from carpooling to safety considerations and other backup solutions to help customers feel comfortable while traveling.

Thank you Xooglers

Thank you Jon for taking the time to speak today! As always, the Xoogler community loves hearing from you and everyone was able to learn something new from this incredible discussion. And thank you to all of the Xooglers who were able to make it Jon’s fireside chat about the start-up world and adapting to changing times. Jon continues to lead Scoop down the path of success, and we are super excited to support him and his business as the Xoogler community!