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Jacob W. Bailey, Owner, Summit Maids


Jacob W. Bailey is the owner and founder of Summit Maids, a commercial and residential cleaning company in Cleveland, Ohio.


For those who don't know anything about you or your work, can you provide a bit of background?

My story has been a long and winding one that has taken me from being a stable boy in the country to startups that made the HBO Silicon Valley show look like a documentary, to working for the UK government as a professional networker in the diplomatic corps. At some point along there I got the entrepreneurial bug and decided that I would take my future into my own hands. Eventually I decided to start doing little experiments to see if anything would catch on and I honed in on the offline SMB world as the playground where I wanted to stretch my founder muscles. I liked that it was predominantly a pen-and-paper industry where my tech background could help me to build something that would really stand out.


Was any one person who was instrumental in helping you get from where you started out, to where you are now?

Absolutely! No one gets anywhere alone. I think that one person who really stands out in my mind was the owner of a commercial Christmas lighting business that I worked for one season during college. He really took me under his wing and showed me what it looked like to be a good owner who actually cared for his team. He regularly took the crews out for lunch and did little things here and there to make everyone feel really cared for. Here we are, many years later, and that experience has stuck with me. Ever since then I wanted to build a business where I could take care of my team in the way that that person did for me. With Summit Maids, I'm glad to say that we have been successful - we have helped at least three cleaners get out of domestic violence situations, got one team member's car out of impound when it was towed, helped two team members buy their first homes, and have helped numerous members of the community.


Is there a particular piece of advice you were given in the early days of your business journey that you still benefit from today?

Take care of your team. It's really that simple. Sure, you can be more profitable in the short term by riding them hard, but that will cause burn out and turnover. Just remembering that your team are people and doing whatever you can to help them in their lives will go so far to creating a culture of trust and loyalty which will, in turn, help you grow your business.



What is the most important lesson you've learned about leadership in your business journey so far?

I used to think that the boss rolling up his or her sleeves and being on the front lines meant that they were more down to earth and humble until one day one of my team members told me that I needed to get back in the office because every day I was out in the field was one less day that I'm at the helm of the ship steering us toward success. That really hit me and changed how I thought about leadership. Now I focus on being visible in other ways than being front and center in the field.



What are the top three things you wish you'd known when you were just starting out?

  1. Don't overthink it. If you're like me, you probably love strategizing and want everything to be perfect before getting started. Get out of your head and just get going. It's ok if things aren't perfect. I promise that most people will never know!

  2. Get Moving. Time in market is more important for success than waiting for everything to be perfect. Just go ahead and get started!

  3. It's not life or death. In 99% of the businesses that you might be working on, messing something up won't cause loss of life. That takes the pressure off and means you can probably correct anything that doesn't go right. So don't worry about things breaking - that's a given. Just focus on creating plans for how to fix it when it all goes south.

In your experience, what is the most effective way to build a strong network of mentors and advisors to guide you in your business endeavors?

I think that one of the best things any new business owner can do is to join a membership organization of other like-minded people. Simply being around other business owners will help you to not feel so isolated when you have bad days and will give you a network of people that you can lean on to help you figure things out. Personally, I'm a huge fan of the Entrepreneur's Organization (EO), but if you can't afford that or don't qualify then you can build your own group by just reaching out to other business owners in your area and starting a regular meeting to build those connections.


How do you determine when it's time to pivot, and what factors should you consider in making that decision?

When the pain of NOT making a change becomes greater than the pain of making the change, that is definitely when it's time to pivot. Sometimes this is due to an opportunity cost, other times it's due to your own happiness. It's a difficult decision, but really one that only you can make. Personally, I have a list of questions that I ask myself when deciding on an opportunity or a project that help me to determine what I should do. Develop your own list based on what is important to you and use it!



How do you stay motivated and inspired during the business cycle of ups and downs?

It's hard! For me, having a group of other entrepreneurs and business owners who are going through the same trials and tribulations that I can lean on and get feedback from is probably the most valuable way to stay motivated and work through problems. Seriously - Find your Tribe!



Looking back, what one thing would you do differently if you could start your journey over again?

I would take a lot more little risks everywhere along the way. Compounding is real. The more little bets you make, the more likelihood that one of them will land and have time to grow. There is very little that will permanently go wrong by taking chances, so just get out there and take your shot!



Where should people follow you to find out more about your work?

Twitter at @JacobWBailey





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