Skot Carruth – CEO and CO-Founder of Philosophie


Spend more time with people and less time studying and working. In business and in life, relationships are at least equally important as work.

Skot Carruth is the CEO and co-founder of Philosophie, a digital innovation firm with offices in San Francisco, Los Angeles, and New York City. Through agile design, rapid prototyping, and software craftsmanship, Philosophie helps organizations solve their most challenging problems and envision how they will operate in the near future.

Alongside his work at Philosophie, Skot co-authored General Assembly’s UX design curriculum and has given talks on design and entrepreneurship at the University of California, Los Angeles Anderson School of Management; the American Institute of Graphic Arts; Galvanize; and Startup UCLA. Skot graduated cum laude from UCLA, where he studied media and business.

Where did the idea for Philosophie come from?

Philosophie is, in practical terms, just like every other professional services business. We trade talent and hard work for money. It’s a simple formula. My co-founder, Emerson, and I realized the value of our skills, so we decided to put them to work in a meaningful way.

On the other, more ideological hand, Philosophie is different. I suppose it’s the “why” behind the business that inspired, and continues to inspire, us. We believe work shouldn’t be something you do to make money but rather an extension of who you are. It shapes your beliefs and gives meaning to your life. In other words, work is an act of philosophy!

What does your typical day look like, and how do you make it productive?

As CEO, I try to balance order and disorder. Planned working time and meetings are important for business, but so is unstructured time. I’m a pressure cooker of ideas, and being able to explore them is my release valve.

What do I do during those planned hours? I look at metrics and solve problems with colleagues, call clients and job candidates, and chip away at internal or client projects. I try to limit my email and meeting time in favor of making things. If a project requires me to learn a new skill over a few weeks or months, I might spend a few hours per day doing that.

How do you bring ideas to life?

Through the design process, of course! It starts with people. Who will benefit or otherwise be affected by an idea? Talking with them is the only way to understand the problem at an emotional level, which is the key to good design. I try to set aside my assumptions and immerse myself in the problem. Inevitably, a solution will emerge, often before bed or during my commute.

The next step is to put the solution to the test. I always assume my first idea is wrong, so I test early and often to avoid wasting resources.

For example, I was recently working to improve our recruiting process and had settled on a third-party applicant tracking software. I purchased a trial subscription and set it up. After getting feedback from the hiring managers, I realized I’d been trying to solve the wrong problem! The issue was our workflow, not our tools.

What happens when a test goes well? I view the solution as a starting point. Can I refine it, making it simpler or more cost-effective? Sometimes, the distance from “test” to “live” is negligible, but other times, they’re galaxies apart.

I might, for instance, want to change our pricing. On the surface, that’s as simple as announcing the adjustment. But behind the scenes, I need our attorney to review client contracts, our accountant to update our invoices, our marketers to revise the website, and our relationship leads to communicate the change to clients. We’re fortunately an agile company, so I might be able to accomplish everything within a few days. For some of our clients, something like this could take months.

What’s one trend that really excites you?

We’re in the midst of a paradigmatic economic shift. Think about it. Today, companies are polarized by size. More so than ever before, America works at either tiny startups or massive corporations. Startups are usually able to innovate, but giant companies control the resources. The few corporations that are making the most of AI and big data seem, frankly, pretty unstoppable.

On the consumer side, things are changing equally quickly. Brand loyalty is all but gone, as is consumers’ susceptibility to advertising. People want to work for and buy from companies whose values match their own, and they’re distrustful of virtually all others. While this is fueling the “maker” movement, it’s also creating something of a Millennial management crisis for old-school leaders.

What does today’s economy portend for tomorrow’s? AI will likely accelerate these trends, replacing jobs and consolidating power in the hands of a few rich companies and the technical elite. What happens to everyone else? It’s easy to imagine both dystopian and utopian outcomes. Will we be free to pursue our individual interests in a plentiful world, or will the economic disparity widen further? It boggles the mind.

What is one habit of yours that makes you more productive as an entrepreneur?

Taking clarity breaks. When Philosophie reached a certain size, I found myself getting wrapped up in projects to satisfy external needs, not necessarily for internal gratification.

Whenever I sense myself losing that intrinsic drive, I create space in which to find it again. In the short run, that may mean taking a day off. Over the longer term, it might mean leaving my everyday life behind for a few months to try something totally new.

What advice would you give your younger self?

Spend more time with people and less time studying and working. In business and in life, relationships are at least equally important as work.

Tell us something that’s true that almost nobody agrees with you on?

I can’t prove it, but experience leads me to believe that most professional programmers are not very good at programming. Same goes for designers.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

In business, analysis and instinct should complement each other, as should big-picture and detail-oriented thinking. Great entrepreneurs know when to apply each.

Also, don’t underestimate the power of empathy. Your investors, customers, managers, staff, and job applicants each see your business differently than you do. View it through each of those lenses to root out improvements.

What is one strategy that has helped you grow your business?

I wouldn’t call it a strategy, but I think the most important things are humility and honest work.

What is one failure you had as an entrepreneur, and how did you overcome it?

It might sound haughty, but I’ve failed by failing to fail.

I’m a cautious person by nature, and I always hedge my bets. I’ve had many tiny, easily fixable failures, but none so spectacular that they spurred real, spontaneous growth. When you only take small risks, you only get small rewards.

To fight my aversion to failure, I’m making bigger bets and recommending that my clients do the same. Failures are the seeds of innovation.

What is one business idea that you’re willing to give away to our readers?

I have hundreds of them. How about a service that lets people swap hard-copy books for digital copies? The paper versions could then be donated to libraries and schools.

Where’s the business opportunity? I’m not sure. That’s for another entrepreneur to figure out.

What is the best $100 you recently spent?

I recently asked my assistant to make me a DMV appointment. Apparently it took four hours! I used to be stingy with money and generous with my time. Now that I have more money and less time, it’s easy to see how I had that backward.

What is one piece of software or a web service that helps you be productive?

I can’t choose just one. My favorites are Alfred for Mac, Trello, Zapier, and Google Drive.

Alfred boosts my productivity by launching programs and finding information online. Trello helps me manage business areas like marketing and recruiting, and it integrates with Zapier. When someone applies for a position,Zapier creates a Trello card and assigns team members tasks to move the applicant through the hiring process. Finally, Google Drive houses our spreadsheets, which we use to track and analyze business metrics. It allows us to collaboratively take notes, write copy, and keep all of our project documentation in one place.

What is the one book that you recommend our community should read?

I’ve read most of the literature that appears on the IdeaMensch list of the most influential books for entrepreneurs . One that isn’t on there is “Maverick: The Story Behind the World’s Most Unusual Workplace” .

The autobiography profiles entrepreneur Ricardo Semler, who turns Semco, a stodgy Brazilian company, into a democratically run, worker-owned, and ultimately successful business. Creating an exciting workplace is one of entrepreneurship’s most rewarding — and most challenging — endeavors. I’ve read a lot about nontraditional organizational structures designed to maximize employee engagement and performance. Most of these experiments fail, but Semco managed to get it right.

What is your favorite quote?

“All work is an act of philosophy.” The line is where our name “Philosophie” comes from. It is spoken by Hugh Akston, a minor fictional character in “Atlas Shrugged.” Ayn Rand’s novel, by the way, is featured in IdeaMensch’s suggested reading list.

Key Learnings

  • Spend more time with people and less time studying and working. In business and in life, relationships are at least equally important as work.
  • Don’t underestimate the power of empathy. Your investors, customers, managers, staff, and job applicants each see your business differently than you do. View it through each of those lenses to root out improvements.
  • It might sound haughty, but I’ve failed by failing to fail.


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