Jacob Bailey

Jacob is the CEO of Summit Maids, a rapidly growing people-first commercial and residential cleaning business based in Cleveland, Ohio. Previously, Jacob has led growth efforts at several venture-backed tech startups, co-founded a travel media business, and served as Vice Consul to the United Kingdom where he helped UK-based tech companies raise more than $100MM in venture capital. Jacob is on a mission to build up the community around him by providing good jobs to great people and partnering with local charities.

Where did the idea for Summit Maids come from?

I saw a need in the community for a cleaning company that actually put the client first. So many of the existing companies had this ‘turn and burn’ model of jamming three or four cleaners into a house for 30 minutes and then moving on to the next – sometimes six or seven times a day. You aren’t going to get a great experience with that as the client. Talk about disruptive! So we came in and looked at every single complaint that all the other companies had and turned those into our guarantees, for example: The number one complaints are either a cleaner not showing up at all, or not doing a very good job. So we instituted the No Call, No Show Guarantee and our 200% Guarantee. Both effectively say that we’re going to show up and to the job right, or else we’ll make it right on our own dime. For our commercial clients, we even go so far as to say that we’ll pay their salary overhead to find another company if it doesn’t work out with us. Everything we do, we do with our clients in mind.

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

A typical day will start with a team check in on Slack and some ‘wake up’ music – an idea that we stole from NASA to get the team hyped up for the day. After that we’ll check in on any overnight email or support tickets that came in and address those. From there, most of the day will be spent working on growth initiatives or on community outreach. Since giving back to the community is one of our core values, we are always looking for opportunities to partner with local nonprofits or other organizations to help raise up the people around us.

How do you bring ideas to life?

Momentum is key to creation. Once we have an idea that we decide to execute on, getting something – anything – moving is the absolute key. The longer you sit and think about something, the less likely you are to actually take action on it. A great example of this was when we decided to partner up with a local foster home network to host a toy drive for Christmas. We went from idea to having identified a partner and setting up a landing page in just a few days. If we’d sat around planning and thinking about it we never would have succeeded in bringing holiday toys to more than 500 children in our community.

What’s one trend that excites you?

I love that more people are starting to think about having side businesses along side their normal jobs. Some employers discourage this, but I think that it is a fantastic way for more people to start thinking like an owner and exercise creativity in ways that they likely don’t get in their 9-5. Plus it’s a fantastic form of expression that lets so many people create something new and add to the world in ways that they wouldn’t have been able to otherwise.

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

Meditation. Hands down. I started meditating daily after reading the book ‘10% Happier’ by Dan Harris and I can honestly say that it has changed my life. I was naturally prone to anger and learning about meditation has helped me take that extra moment between stimuli and response to evaluate how I really want to respond. That’s not to say that it’s a magic bullet, or that I don’t ever get angry – I am still human after all! But meditation gives me another tool to be the best version of myself that I can be and that translates into being more productive and being a better leader.

What advice would you give your younger self?

Stop caring what others think. This includes worrying about getting the best grades in school. Social skills are way more important than whether you have a perfect GPA in real life. I worried so much about my grades and what others thought of me that I seriously neglected my social life. As most of us learn as we grow up, your network is your net worth and just about everything in the real world gets done through relationships. So maybe a ‘B’ or a ‘C’ is good enough, and then use the rest of that time building up friendships that will last a lifetime. (Unless you want to be a doctor or a lawyer, then grades matter!)

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

Capitalism is the best way to affect change in your community. Let’s face it, unless you are a politician, then money rules the world. So rather than trying to change the system, learn to operate within it and use it to change the world. In my case, I want to provide more good jobs to help alleviate poverty. I can’t do that without building a strong, profitable, business. Likewise, I want to help children get more opportunities in life, so I choose to donate to and partner with local nonprofits who focus on helping children in my city. I wouldn’t be able to support those organizations without having a profitable business. For me, affecting the most change in this world comes from operating in a capitalist society.

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

Well, I already talked about meditating, so I’ll say taking time out of your day to read on a regular basis. This is time that you get to spend learning from some of the best in the world, or escaping into a fictional world and getting away from the stresses of everyday life. This is time for you. Having that time will help you to rest and recover, and to learn about new things to be a better leader.

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

Building a business that focuses on our clients. Literally everything that we do, we keep our clients in mind – from thinking about new services to roll out to who we choose to hire. Doing this and constantly asking ourselves, “How will this benefit the clients?”, has allowed us to build a business that was recently named one of Newsweek’s Most Loved Workplaces and is one of the fastest growing cleaning companies in Cleveland.

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

Last year we decided to try expanding to a new city and it was a miserable failure. We seriously wasted so much time and money trying to get this location off the ground, only to have to pack it all up and refocus on our core business location. What we realized in the post-mortem was that we hadn’t accurately done our market research ahead of time. We thought that we could just copy/paste our model into another market and it would work the same way. As it turned out there were several other factors at work that we hadn’t thought about related to the local market that we didn’t have in our home market. It was a painful lesson, to be sure, but we definitely learned our lesson about doing the work ahead of time to fully understand other markets before we dive in.

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

I’ve always thought that someone could build a really fun wine brand called “Basic Wines” and really lean into the idea of a canned wine that isn’t intimidating. You could call the different varietals “Basic Red” and “Basic White”, etc. Make it canned for portability. There could be some really fun marketing campaigns around it leaning into the ‘basic’ concept. Basically the Starbucks of wine.

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

I don’t tend to buy a lot for myself, but I recently got a pair of noise canceling headphones for when I’m doing deep work or while I’m on planes and they have been fantastic. Aside from that, we just recently made a donation to the local animal shelter which is a cause that my wife and I care a lot about and always is a fantastic feeling.

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

Notion is probably the one that I go to most of all. It’s my central hub for all the SOPs in the business and all our training materials. Any time we want to document a new process or procedure, it goes in there. That way, when we bring on a new team member we can just get them set up in Notion and they have access to all the training materials that they may need to get completely up to speed.

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

The Obstacle is the Way by Ryan Holiday is probably one of my favorites. Any time I’m having a rough day or just feeling defeated I can grab that book and flip to any random page and it will help get my head back on straight so that I can work through the problem at hand.

What is your favorite quote?

“The brave, they may not live forever, but the cautious do not live at all.” – Richard Branson. I had the fabulous fortune to meet Richard some time ago and he has always been one of my business idols. This quote is one that really hit me and has stuck with me ever since I first heard it. I have a tendency to be a very cautious person naturally, so this quote helps me to remember to actually live an interesting life.

Key Learnings:

• Live boldly or else risk not living at all.
• Do your market research before jumping into a new market area – don’t just assume that your learnings will transfer from one market to the next.
• Make time to read. It will either teach you something new or help you escape into another world. Either way, this is time just for you to escape the day.
• Have a mission that you adhere to religiously. It isn’t enough to be an ‘also ran’ in todays’ business world, have something that you stand for and build a business around that.