Ross Kimbarovsky - Founder and CEO at crowdSPRING and Startup Foundry

Don’t put off being happy. Focus your energies on the things that make you happy every day of your life.

Ross Kimbarovsky is founder and CEO at crowdSPRING and Startup Foundry.

In 2007, Ross left a successful 13-year career as a trial lawyer to pursue his dream of founding a technology company (in part so that he could wear shorts and sandals to work every day) by founding crowdSPRING – one of the world’s leading marketplaces for crowdsourced logo design, web design, graphic design, product design, naming and writing services. crowdSPRING is helping to re-shape advertising and marketing around the world by giving clients of all size access to 200,000 talented designers and writers. Clients who need a logo, website, custom graphic design, industrial design, a new company name or written content post what they need, when they need it and how much they’ll pay. Once posted, creatives from around the world submit actual work. Buyers select from among actual work (an average of 100+ per project), not bids or proposals. crowdSPRING has received numerous national and international awards and has helped tens of thousands of Buyers from 100 countries (including entrepreneurs, startups, small businesses and the world’s best Brands, agencies and marketers) meet their creative needs.

In 2014, Ross founded Startup Foundry. Startup Foundry is a team of engineers, marketers, and entrepreneurs building innovative and sustainable startups. Startup Foundry’s launched projects include Quickly Legal (helping entrepreneurs and businesses create, sign and manage smart, simple business contracts on any device), Respect (reimagining in-home care for the elderly), and Curio (helping marketers save time, build their audience and manage all social media efforts using Artificial Intelligence to discover, schedule, share and analyze the best content).

Ross mentors entrepreneurs through TechStars and Founder Institute is a member of the Executive Advisory Board for TechWeek and was honored as one of Techweek100′s top technology leaders and business visionaries. Ross frequently speaks to entrepreneurs, small business owners and marketers about crowdsourcing, marketing, and entrepreneurship. Ross wears shorts and sandals to work on most days.

Where did the idea for crowdspring.com come from?

In 2006, I was a trial attorney at a mid-size Chicago firm. Among other responsibilities, I led a project to redesign the firm’s website. It 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 six hours researching.

I was convinced that there was a better way to buy design services and I was intent on finding it. I stumbled on a group of graphic design students in Malaysia who were holding a fun 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 have 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.

Early in the morning, I called a friend who at the time was considering buying a small video post-production company in Chicago and outsource 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).

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

I run two companies – crowdSPRING and Startup Foundry. It’s rare for days to be typical, but generally, I set three priorities for each day. Some years ago, I recorded a short video explaining how/why I do this. This means that I typically break the day into three periods (of roughly three hours each).

I get up between 7 and 7:15 am and join my teams via Slack. Breakfast is quick and easy – I drink Soylent. Both crowdSPRING and Startup Foundry have distributed teams (half the people work out of our combined Chicago office and half are all over the U.S. and the world, including Brazil, Belgium, and Poland). We used to do daily engineering team scrums via Google hangout (with both teams) but have shifted to daily written reports to conserve time and preserve focus.

The first three hours of the day are about tackling my highest priority goal for the day. I work at home and try to avoid interruptions. But that’s not always possible. For example, It’s not uncommon for me to have three or four quick hangouts with team leads in the morning.

I’m not a fan of meetings and for years, have experimented with different ways to manage them. For a while, I’ve asked my teams, when scheduling a meeting, to always include an agenda with a specific list of actionable items. Most of the time, anything that needs to be reported is done in writing before the meeting. That pushes us to resolve issues without meetings and more efficiently.

One small productivity tip: schedule meetings in 10-minute increments. Something that needs less than 10 minutes shouldn’t need a scheduled time. Nor do you need to force a meeting into 30 minutes. If the meeting needs only 15 minutes, schedule it for 15. I cheat a little by scheduling 30-minute meetings for 20 minutes. This pushes us to focus on the issues and saves a lot of time during the week.

At around 10:30 am every morning, I shower and head to the office. I have a 30-minute commute (by car), and I either listen to podcasts or have a call with an entrepreneur looking for some advice. I was very fortunate to have had great mentors when I founded crowdSPRING and helping younger entrepreneurs is a small way to express my gratitude.

When I get to the office, I often catch-up with my product designers. Once per week, I have 1on1’s with my marketing leads. Rather than sit at a table, all 1on1s are walking. We walk around the West Loop area in Chicago and talk for 20 to 30 minutes. It’s a healthy way to have a conversation. Before each 1on1, each lead answers some questions about their top accomplishments from the prior week, top goals for the coming week, blockers, and how I can help them. I read their answers in advance, and our conversation focuses on strategy and insights. Afterward, I typically have lunch with the entire team (part of our culture is eating together – we’ve had some fun conversations at lunch and enjoy each other’s company).

After lunch, I often catch-up with my engineering team leads in quick hangouts and focus on email.

At around 3 pm each day, I focus on my second priority goal for the day. I do my best to create uninterrupted work time for that period (often working with headphones).

I leave the office around 6:45 pm each day for my 30-minute commute home and dinner with my family. I spend evenings with my family (three kids – one started college this year). It’s rare that I work at home in the evenings while my family is awake.

After everyone goes to bed, I tend to write (blog posts, articles, etc.) and focus on my third goal for the day. That’s a good, uninterrupted, quiet time for me to focus. Typically, around 11 pm on weekdays, I do a 90 minute, 35-mile bike ride on a recumbent bike at home. I’ll often catch up with Netflix or read during that ride. After my ride and a quick sauna and shower, I often Facetime with my daughter (at Boston University) and then read for about 1-2 hours (sometimes, I catch-up with Twitter and Facebook at that time) and go to sleep. I know it’s a long day, but I’m fortunate not to need a ton of sleep.

Weekends are for family, reading and relaxing. I rarely structure weekends. On a typical weekend day, I might hang out with my wife and kids, go hiking with them, read a book (my goal is to read one book every week) or do a 75-mile bike ride outdoors. Every weekend is different.

How do you bring ideas to life?

I find phenomenally smart, driven people who share my vision, give them lots of autonomy and get out of their way.

What’s one trend that excites you?

Lately, I’ve been fascinated by voice interfaces. I recently started playing with an Amazon Echo Dot and am learning different ways to control music, lights, fans, etc. I believe that voice control is the future and am pretty excited about what can already be done using your voice.

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

I talked about my three goals for each day. That’s a good way for me to stay productive. For others, it might be creating to-do lists, but I’ve personally found those to be inefficient because to-do lists are rarely prioritized and often demoralizing when you can’t do many of the items on your list. I carry this idea to weekends too, but the goals there are a bit less structured and focus on family and rest.

What advice would you give your younger self?

Don’t put off being happy. Focus your energies on the things that make you happy every day of your life.

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

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, but hard work rarely scales. As a trial attorney, I was used to 80 and sometimes 100 hour weeks. It’s impossible to keep focus 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.

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

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. Many people focus on the strategy of finding such a balance but forget to create this balance in their lives. 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.

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

The answer is the same to the question about how I bring ideas to life. I find phenomenally smart, driven people who share my vision, give them lots of autonomy and get out of their way. I’m serious. Too many people fear to hire smart people. Such fears often lead to failure.

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

In 2009, as we started to see more traffic, we hit a technical wall, and our site nearly collapsed under the load. I wrote extensively about the problem and the lessons we learned. I was humbled by the response from our community. It was a tough year, but we came out of it stronger than ever (but with some gray hair – or in my case, still a bald head).

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

Two-sided marketplaces are exceptionally difficult to build. But as Airbnb, Etsy, Uber, and others show, they can be very successful. There’s an opportunity to do something in health care to make pricing more transparent. It’s a challenging area, but innovation in pricing and transparency could transform the whole industry.

What is the best $100 you recently spent? What and why?

While I appreciate gadgets, I find that experiences are much more lasting. This summer, I spent seven weeks traveling around Europe with my family (we visited four countries, including Russia, Ukraine, Spain and France). I can pick just about any activity on any day during our trip as an answer to that question, but one of the highlights was a paella dinner on the beach in Barcelona, Spain.

Incidentally, I time-shifted and worked six of the seven weeks we were away. As I mentioned above, we have a distributed team. I often experiment to see how they feel when working remote to find ways I can improve how we work with distributed teams. This was a great learning experience.

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

I love Google Hangouts. Years ago, I used to rely on Skype for video calls, but the quality became much worse, and I discovered Hangouts.

One small productivity tip: to avoid having to figure out how to meet via Hangout, we’ve created special rooms for each team (crowdSPRING’s are based on cities and Startup Foundry’s are based on space themes). We then created link shorteners for each and now, whenever someone wants to meet, we just mention where and everyone knows the URL without us having to share it every time. It’s a pretty cool way to quickly get into a hangout without having to share links. Plus, I get to say to someone … “let’s meet in Tokyo.”

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

Many years ago, I read “Tribal Leadership, “ and it changed my perspective on how to build great. At the time, I bought copies for everyone on my team and asked them to read it. I wrote a blog post explaining why I found that book to be transformational for me and I’d encourage everyone looking to build great teams to read that book.

What is your favorite quote?

“You never fail until you stop trying.” Albert Einstein.

Connect:

https://www.crowdspring.com/
https://www.startupfoundry.com/
Ross Kimbarovsky on Twitter: @rosskimbarovsky
Ross Kimbarovsky on Linkedin: https://www.linkedin.com/in/rosskimbarovsky

Lessons Learned

(Blurbs and ideas summarized and sometimes just cut and pasted by the IdeaMensch crew.)

  • Set priorities for each day. Then break each day into three periods (roughly three hours each). The first three hours of the day are about tackling the highest priority goal for the day.
  • The second three-hour period of each day is for meetings and 1:1s.   One small productivity tip: schedule meetings in 10-minute increments. Something that needs less than 10 minutes shouldn’t need a scheduled time. Nor do you need to force a meeting into 30 minutes. If the meeting needs only 15 minutes, schedule it for 15. Ross cheats a little by scheduling 30-minute meetings for 20 minutes. This pushes his team to focus on the issues and saves a lot of time during the week.
  • At around 3 pm each day,  focus on your second priority goal for the day. This is the time to create uninterrupted work, so make sure you have the physical and mental space. Ross often works with headphones during this time.
  • Ross accomplishes his third priority of the day after his family goes to bed. That allows him to spend some quality time with them every day. He takes the weekends off work as well and allows for lots of high-quality family time.
  • Don’t put off being happy. Focus your energies on the things that make you happy every day of your life.
  • 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, but hard work rarely scales.

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