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by Derek Loosvelt | February 17, 2020


Ross Kimbarovsky is the founder and CEO of the gig economy business crowdspring, a marketplace for design professionals whose community of more than 220,000 freelancers provides creative services to agencies, small businesses, entrepreneurs, and nonprofits in 195 countries. Ross is also a mentor to entrepreneurs through startup accelerator TechStars, and has been named one of Techweek100′s top technology leaders and business visionaries. Before starting crowdspring, Ross worked as a trial attorney for 13 years. Now, on most days, Ross wears sandals and shorts to the office.

Recently, Vault spoke with Ross about his career trajectory, his company, the state of the gig economy, and the startup advice he has for entrepreneurs. Below is an excerpt of that conversation.

Vault: Where did you grow up and go to school? And what was your first job out of school?

Ross: I was born and grew up in Kiev, Ukraine. When I was nine, my family emigrated to Chicago. I graduated from Northwestern University with dual degrees in political science and philosophy. I received my law degree from the University of Illinois College of Law and had a successful trial law practice for 13 years. I was a partner at two Chicago law firms, counseling and representing clients from small internet startups to Fortune 100 companies.

Vault: How did you transition from attorney to startup founder?

Ross: I was always entrepreneurial, even while practicing law. I founded and led several new practice areas at both law firms I worked for. And I started working with internet startups in 1995, right when the internet was first commercialized. Also in 1995, I designed and coded one of the first law firm websites ever (for the first firm I worked for). Everything was hand-coded in 1995, and it was a painful process. But coding the site was a passion project for me. 

In 2006, I led a project to redesign the website of the second law firm I worked for. This redesign was a typical RFP (request for proposal) project. We solicited proposals, interviewed design firms, and hired the best one. I hope I never have to manage another RFP process. It’s painful, frustrating, and often disappointing. We spent a lot of money, but I was very unhappy with the results when the design firm presented their work. Frustrated, I went home and spent hours researching.

I was convinced there was a better way to buy design services and was intent on finding it. I stumbled upon a group of graphic design students in Malaysia who were holding a competition to see who could design the best product print ad. They were doing this just for fun, and I was impressed with the quality of their work. I've always been a fan of creative advertising and know the cost of buying high-quality graphic design. I wondered whether it was possible to design logos, websites, and other things by leveraging the crowd.

One morning, I called a friend who was considering buying a small video post-production company in Chicago and outsourcing the work to India. I wasn’t yet sure how to connect the dots, but our conversations and research over the next six months led us to the idea that became crowdspring in 2007 (we launched publicly in 2008 after developing and designing the product/site).

I left my law practice at the end of 2007 to focus on crowd spring full-time. There’s a rumor that I left law so that I could wear shorts to work. The rumor is true.

Vault: Could you talk a little about what crowdspring does?

Ross: Crowdspring is one of the world’s leading marketplaces for design and naming services. Importantly, crowdspring offers business owners an affordable and proven platform for custom design and naming at a fraction of the price they traditionally paid. Although our typical customer is a startup or small business, we’ve worked with the world’s best brands, including Amazon, LG, Starbucks, Microsoft, Barilla, and Philips, and also with many of the world’s best agencies.

Instead of paying thousands or tens of thousands of dollars to agencies or freelancers, projects on crowdspring start at $299 (including all fees) and there’s a 100 percent money-back guarantee. You can find more on how crowdspring works here.

Vault: What sets crowd spring apart from its competitors?

Ross: For entrepreneurs, small businesses, and agencies, our unique model and award-winning process eliminates most of the concerns encountered when buying design and naming services. We take a lot of the work and stress out of the equation for you: you won't need to get quotes in advance for the work, or interview freelancer after freelancer. You set the price for your project, and freelancers from around the world will post their actual custom designs (or names) for you to review. When your project ends, you choose the entry you like the best. It’s that easy!

Plus you get a free, customized legal contract transferring full intellectual property rights to you, and the peace of mind that our platform helps you to focus on the work and avoid stressing about ways you need to communicate with freelancers, transfer large files, or protect your purchase.

Vault: What does the future look like for crowdspring and the gig economy in general?

The nature of work is in flux. The number of people engaged in gig work has continued to increase, and that growth is unlikely to stop, barring significant government regulation.

Online platforms have made new types of work possible, as crowdspring and other design platforms have transformed the way people and businesses buy design, logo, and naming services. Uber, Lyft, and others transformed the way people buy local transportation services. Airbnb and others transformed the way people travel. We’re seeing similar changes all over the world, across many industries.

Now, more than a third of all U.S. employees are engaged in gig work full-time or part-time. Companies are increasingly relaxing rules that require employees to work out of an office, and this has led to more flexible hiring rules and more opportunities for people to moonlight. In fact, one in six enterprise workers are actually gig workers. That’s a remarkable statistic.

The reason for this shift has to do with many factors, including increasing demand for skilled workers. Companies are increasingly willing to hire skilled workers and retirees on a gig-basis to meet a growing demand and reduce their costs. We regularly see this on crowdspring. Experienced designers who work at agencies often moonlight on crowdspring. It’s a big win for clients and extra income for designers.

Vault: What do you recommend to future entrepreneurs/startup founders in the tech space?

Ross: Having talked with and helped thousands of entrepreneurs and small business owners over the years, there are two important things every person starting a new business should understand. First, find a work-life balance that makes sense for you. I know there’s much debate on this subject, with some people arguing either that it’s impossible to create that balance, or that balance is created when you focus on work when necessary and life when necessary. But life doesn’t stop while you focus on work.

For me, balance is important because it ensures I spend time with my family, focus on my personal health and emotional well-being, continue learning, and do great work. I highly recommend that every person, and especially every entrepreneur, find a balance that works for them.

The truth is that hard work doesn’t scale. There’s a dominant culture, especially among technology startups, that you must work hard to succeed. This can be true, and some companies appear to persevere even when their culture demands 80-hour weeks. But those are exceptions—hard work rarely scales. It’s impossible to keep focus and be creative when you work that hard for a long time. And, of course, you can’t have a family or life balance. Far too many people in the startup community fall prey to this trap.

Second, make sure you understand the importance of building a strong brand when you start your company. Ideas are a dime-a-dozen. Execution is the difference between success and failure. Most inexperienced entrepreneurs don’t understand that a business’s brand identity (everything visual about a brand) is an important competitive advantage—if executed well. Unfortunately, too many business owners lack the skills to build their own brand identity. 

Good design is good business. Conversely, poor design frustrates customers and prospective customers and pushes them to your competitors. Outsourcing graphic and web design to a company like crowdspring gives business owners the freedom to focus their energy on the things they’re uniquely able to do best—and to focus on the success of their business. 

Every business owner should strive to work on their business, rather than in their business. The more a business owner can outsource and delegate, the more they can focus on strategy and the bigger picture. 

I talk about all these things and more in a new e-book on how to start a business. You can get your free copy here