#35 Taylor Cone: The Entrepreneurial Coach

published on 02 September 2021

Stanford helped me discover my life’s mission: designing experiences that enable people to see themselves, the world, or the problem they’re trying to solve in new, more empowering ways. 

Screenshot 2021-09-01 at 10.05.22-abevm

Taylor is a born people activator. His voice is smooth as silk but, at the same time, firm and clear. When he talks, it is hard not to smile, as his level of passion and positive energy is beyond contagious. Taylor is the person every team would love to have. He is an engineer and product person by heart, and can pretty much pep talk you to do anything imaginable. Magical!

Taylor was born and grew up in the United States and has always been fascinated with building. He holds a bachelor’s degree in Engineering Physics and a master’s degree in Mechanical Engineering from Stanford University. He has a particular interest in robotics and designing innovative business models and has spent a decade developing products and building innovation teams, in Silicon Valley and around the world. He is now a co-founder of Compa, a startup with the goal of making compensation fair and competitive for everyone. 

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This interview has been edited and condensed for clarity.

What did you dream of when you were a kid?

I dreamed about two things. First, I wanted to be a river guide. I went on a rafting trip every year during my youth, and I still enjoy it today. Second, I wanted to become an inventor. Growing up, I loved playing with Legos. I also had a math and science tutor who inspired me to pursue a rigorous educational path in science.

When I was 8 or 9 years old, I visited a robotics research lab on the Stanford campus. It was such a vibrant and fascinating place. That experience changed my life for good. That day, I told myself: “I want to go to Stanford, I want to study mechanical engineering, and I want to build robots.”

Where does your passion for building things and turning ideas into life come from?

My passion for building began with simple sketches, which was a way for me to bring my ideas into life. I sketched a lot when I was younger, and I recently found one of my best drawings, from maybe 25 years ago: it is a detailed sketch of what, today, we would call a smartwatch. A visionary! (laughs) 

Can you tell us about a project you worked on at Stanford?

This happened between my sophomore and junior years. I was finally building robots. Together with an incredible team, we made a perching miniature UAV robot that could sense a wall and perch on it. It was a wonderful learning experience. The main lesson I took from it was understanding the importance of having an iterative way of thinking. 

What is the biggest takeaway from your time at Stanford? 

Stanford made me fall in love with teaching, coaching and design thinking. Stanford helped me discover my life’s passion: designing experiences that enable people to see themselves, the world, or the problem they’re trying to solve in new, more empowering ways. 

How was it to leave Stanford?

My time at Stanford was one of the most defining periods of my life. It was very hard for me to say farewell after graduating (and, because of my time teaching at the d.school, I didn’t really leave until about three years after graduating). You simply don’t want to leave such an incredible place. But, I am still profoundly connected with the Stanford community. I’m still close with friends and mentors on campus, and I coach the course  “Design for Extreme Affordability” at the d.school (a class I used to attend as a student). 

Launching new products is hard. How do you make a product people love?

What matters is having tight feedback cycles with the people you are building the product for. It is not rocket science, but you will be surprised how many companies are doing it wrong.

The best product development strategies tightly couple short feedback cycles (not just user feedback but also insights from data) with a lean philosophy that enables you to move fast and to change direction when needed. It is crucial to understand what is noise and what isn't. It’s important to spend time designing research that makes sense for your particular customer group. If not, you end up building the wrong product. 

This is the question you should always ask yourself before building a product: what do my users really need? Don’t just make something they want - make something they need.

Why take the leap of faith and create a fast-growing startup?

I’ve always had an entrepreneurial spirit. I founded my own consulting company, Lightshed, three years ago. I ran design thinking workshops and other innovation experiences. Things were going pretty well. But then, the pandemic hit, and my pipeline of clients dried up. 

Soon after the lockdown began last year, I received a call from Charlie. Charlie had an idea for a company, which immediately intrigued me. It didn’t take long before we began formalizing our thinking, reaching out to potential customers, and building our first prototypes. It was a heck of a time! 

I was (and am) thrilled to work with Charlie; he has a decade of experience in the industry and is a fantastic leader. We are trying to solve a clear problem that has been highly underserved. It’s extremely rewarding to be working on something so specific, so well-defined, and so clearly needed.

Can you give us the aha moment and the vision for Compa?

We basically have an aha moment every day (laughs). More seriously, it really hit us when we realized that our target users still – in 2021 – routinely scribble using pen and paper and use homegrown spreadsheets with unreliable data when making pay decisions. That was crazy!

Always look for the duct tape in the room. If someone is applying duct tape, it means that there is an evident problem to solve. 

Compa is a compensation software company helping recruiters design competitive and fair offers and avoid potential pay bias. The vision is to help create a tool that will allow every employee/employer relationship to start from a place of trust and transparency. Unfortunately, that is often the opposite of how it is today. We want to change that!

What’s your superpower?

My superpower is identifying, and, when necessary, executing, the highest value activity a team can do to move forward. I thrive as the one who propels teams forward.

You are a river guide. What makes navigating rivers special to you?

It makes me feel alive. During every trip, we do rock jumping. I love to motivate people to jump (especially if they are a bit scared). In every case, they come out of the water with an incredible smile on their face. They usually want to jump again, and as a guide, it’s incredibly rewarding to see.

Rafting on the Rogue River in Oregon
Rafting on the Rogue River in Oregon

I love when people discover that they can do something they thought they couldn’t. These moments fire me up and remind me of my big why in life. 

You recently moved from San Francisco to Boston. Any reasons for this change?

Like many decisions in life, it was love. My girlfriend lives in Boston, and we have been in a long-distance relationship for about a year and a half. We decided it was finally time to figure out a way to be together. With COVID upending numerous aspects of life, I felt ready to make a big change. I am thrilled to be writing my next chapter here in Boston. 

Taylor hiking in Yosemite, California.
Taylor hiking in Yosemite, California.

If you could change one thing in your journey, what would it be?

I don't know (laughs). I recently watched a video of Anthony Hopkins where he said: “I don’t want to be anything other than what I am. I can say that with passion. No regrets”.

Honestly, that resonates with me. I have learned a ton from my mistakes, and I wouldn't change anything. It might be the cliche answer, but it’s how I feel. 

When was the time you felt the most vulnerable?

It was when I launched my consulting business, Lighshed. I had to put my whole self on the line. I was the company's product, and I felt very vulnerable as everything I did was an extension of myself. It was very challenging, the pressure to perform was always there. However, this level of vulnerability made me more resilient and ready to tackle whatever big leaps were next – like co-founding another startup (Compa) in the midst of a pandemic! (laughs).  

What would you do if you only had 30 days to live?

My usual answer would be to travel all over the world. What’s most important to me now is spending time with the people I love the most. I enjoy simple things in life, like driving to the ocean or going for walks in the woods. I lost my grandparents a couple of years ago, and it reminded me of what matters in life. 

Taylor on a snowy beach in Tahoe with his girlfriend, Morgan
Taylor on a snowy beach in Tahoe with his girlfriend, Morgan

Do you have an inspiring figure?

My brother, Micheal. He has taught me a lot about what it means to live a good life and exhibit excellence in everything you do. 

One book?

Sprint by Jake Knapp 

YouTube channel?

Smarter Everyday


Where should we begin? With Esther Perel.

If you were to start a company today, what would be your one-billion dollars idea?

I want to challenge this question and ask how you could measure success beyond a monetary unit. It is more important to ask ourselves how to help a billion people live 10% better. That’s what really excites me. 

Our Main Takeaways

  • Having tight feedback cycles with your customers is not rocket science, but is extremely important if you want to build a product people love. 
  • Going outside of your comfort zone makes you feel alive. Don’t underestimate the energy you can get from stepping into the unknown. 
  • Aiming for monetary value can be motivating, but measuring success beyond that is exciting.

Inspiring story Taylor, thank you very much.

Taylor (right) at a fruit stand in Costa Rica with two of his dearest friends
Taylor (right) at a fruit stand in Costa Rica with two of his dearest friends

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