“5 things I wish someone told me before I became a CEO” with Madison Mikhail Bush, CEO of POINT

The pit in your stomach means you’re making moves. The pit in your stomach is here to stay. It means you’re uncomfortable and most likely pushing yourself to keep the pace you know you need to. As a leader, you might naturally believe nothing is ever finished, and your brain is years ahead. You’ll constantly be thinking through a million things to do and directions you could take. I sometimes view my brain as a racket ball court that has 75 balls at play bouncing off the walls at all times. Between the chaotic pace of my mind and the pit in my stomach, it’s enough to keep you in bed forever or push you to wake up early and take on the day. You have to decide what it’s going to be. General tips to calming both your stomach and brain: take nothing personally, define (at least) one accomplishment of the day that will help you fall asleep in a good frame of mind, get some sunshine, sweat it out, know the smarter you work — the better you feel, and do something before bed that has nothing to do with work.

As a part of our series about powerful women, I had the pleasure of interviewing Madison Mikhail Bush. Madison is the Founder and CEO of POINT — the easiest way to volunteer, ever. Madison was named one of the Top 10 Entrepreneurs in Columbus for 2018 and she lives between Columbus and NYC with her two giant tortoises.

Thank you so much for doing this with us! Can you tell us a bit about your “backstory”? What led you to this particular career path?

I never really thought of myself as an entrepreneur, and when someone told me I was a social entrepreneur, I had to go to the bathroom and google what that meant. But I’ve always had a knack for seeing something that needed to be fixed and doing something about it. I blame my parents. My dad made me knock on my neighbor’s doors and offer my “lawn mulching skills” at 9 years old. That gave me the confidence to start programs, businesses, or nonprofits whenever I realized there was an opportunity to make something happen to have a positive impact on my community.

While I was in college, I came to the realization that it was easier for me to order ramen at 11 p.m. from my bed than it was to do something good in my own neighborhood. Technology has made it easier to do pretty much everything, but nonprofits are left in the tech stone age. If you have something you care about and you want to help, it’s hard to know where to start. You have to do a ton of googling to find a reliable nonprofit, then call them and coordinate open times just to sign up for a volunteer experience. I wanted to make nonprofit engagement and volunteering easy. That’s why we built an app for people to use as the starting POINT, making it as easy to do good as it is to order an Uber.

Can you share the most interesting story that happened to you since you began leading your company?

I full-on slammed into the Founder and CEO of Twitter and Square *facepalm*. We had an advisor who worked at Twitter, and as I was walking back to the headquarters from grabbing lunch, I accidentally ran into (read: body checked) another person. I looked up, embarrassed, and it was Jack freaking Dorsey. He dropped a bunch of things, and instead of apologizing and helping, or offering to buy him a coffee and get some advice, I just froze and stared at him then speed walked away.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

My CTO, Alex, and I were working on push notifications for POINT. Writing isn’t either of our strong suit, but our Director of Communications wasn’t available so we wrote the notification ourselves. Turns out we pushed a notification with several grammatical errors to thousands of people — including “there’re” which isn’t a word. Almost immediately our users started DM’ing us, and I fell on the ground laughing. We sent out a second push notification asking for people to come teach us grammar. It ended up being a good laugh for everyone, but now we know to never publish anything without having someone else look it over.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. What is it about the position of CEO or executive that most attracted you to it?

I think most people become an entrepreneur or a CEO for the title or freedom, but that isn’t why I started POINT. I started POINT because I wanted to see a better solution to finding a way to volunteer and do more good. But growing up, I was always one of those “bossy” young girls (AKA a leader) so running a company is a natural fit for me. Being a CEO allows me to work full steam ahead, without the hierarchy of working in a corporate system or for another person. If I see a need or an opportunity, I can create something to fill it, mobilizing my company’s resources and people to drive impact in our community.

Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

When people think CEO they think of a Captain — someone who’s steering the ship, deciding where to go, and is willing to go down with it. But I think a more accurate word for CEO could be “fireman” (or woman), because you are constantly trying to prevent and put out fires when things don’t go as planned. Sometimes executives can be seen as a person who barks orders and expects others to carry out tasks, but a good CEO teaches people what to do and empowers them to not only solve problems as they come, but prevent them from happening in the first place.

As the executive of a startup, I have to inspire and lead people towards a common goal, but I also manage and am responsible for finances, growth, and how the company interacts with our community. You can’t wear the hat of just an executive — you have to wear the marketing, development, accounting, outreach, etc. hats at some point, too (and usually multiple at the same time).

What is the one thing that you enjoy most about being an executive?

Seeing the big picture. I thrive when I can create a clear future vision that I can bring to life. To see the big picture to me isn’t just seeing all of the possibilities of this moment, but where something can go at it’s best, 5 or 10 years down the road. Where could we be? How can we get there? What can we make possible? How can we have a bigger, more positive impact on the community?

But on a day to day basis, I love solving problems for our charity partners and making what they do easier. To me, that’s the whole point.

What are the downsides of being an executive?

The pressure. I think it’s easier and more socially acceptable for men to talk about the pressure they face at work, and when women talk about it they can be seen as weak. But recognizing that you are under an immense amount of pressure isn’t a weakness, and if you can thrive in that environment, you are strong as heck. Throughout the years, I’ve found is that there is just as much pressure when your company is succeeding as when it’s failing. There are times when I get a pit in my stomach knowing that I have people and families relying on me for income, and it seems like there is a never-ending list of fires to put out to make that happen. However, that pressure is a plus because it energizes me and makes me shoot out of bed in the morning to tackle all I can that day.

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

Even I sometimes think that CEOs should be these extroverted/networking-pros/people, but I am definitely an introvert. It might be my best-kept secret. Before I walk into a room I have to psych myself up to put myself out there and talk to new people, but it’s part of what you have to do to build a community. Don’t get me wrong, I do love talking to people, but that doesn’t mean it’s easy for me to walk into a crowded room.

I think that most people have this vision in their heads that CEOs are workaholics (true) who neglect their families. But I make it a priority to spend time with my family. I make it nonnegotiable to visit or call my grandpa once a week. I also have 3 little sisters that I try to keep up with, even though they will say I’m always behind on the sibling snapchat group. There are people that need to remain a priority and I never let myself be too busy for them — my grandpa is at the top of that list.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

While it is difficult to be taken seriously when you’ve got a squeaky high-pitched voice, I’ve found that the biggest challenges I face come from being young. People have asked me, “When is your boss coming?” prior to introductions. Being seen as an equal player in the Midwest business market is hard, especially when it seems that years of experience often outweigh new ideas and solutions to challenges our community has faced for years that have gone unaddressed.

What is the most striking difference between your actual job and how you thought the job would be?

I didn’t understand maintaining success takes just as much work as starting from scratch. We’re still grinding. Once you get the feeling that you’re coasting, you realize it’s because you’re not growing. Then you’ve got to go back to the grind.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive?

I think persistence is the only thing that matters. If you give up at the first sign of difficulty, or at the first failure you encounter (believe me, there will be more) then this probably isn’t for you. Your options are to tap out or work like mad.

What advice would you give to other female leaders to help their team to thrive?

You need to find the balance between being direct with what you need, and trusting people to do what you expect of them. But there will be times when people let you down, or (try to) walk all over you. In those moments, you need to summon your strength and quiet the voice that says “they’ll think you’re mean,” so that you can be direct about how the person’s shortcomings affected the company and remind them of your expectations. You don’t want to make your employees feel small, but you can’t let yourself feel small either.

Additionally, most of us need to work on being more assertive when we are the expert in the room. There are so many instances where I have seen women who know their stuff get talked over, or shrink back when they should be the only expert voice in the room. I’ve been one of them. It’s hard to speak up, but we can all work on being more confident in our work, knowledge, and abilities.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There are not many people that are willing to go out on a limb for you and introduce you to every single person they know. That’s not the case with Regan Olvey; she’s a consultant at Columbus Business First and, in general, a superhuman. After I first met Regan, she fired off lists and lists of people she wanted me to meet to help me grow my network. To this day, I’ve never seen anyone write so many intro emails, and I know it would have taken me months of effort to do what she did in days. I’ll always be thankful that she put all her relationships on the line for me and a just-launched POINT.

How have you used your success to make the world a better place?

Well, that’s what POINT is built to do. People using POINT can easily connect with charities working for things they care about and sign up to volunteer by tapping “go”. Charities use POINT’s dashboard to manage, track, and engage volunteers. Businesses and schools can use POINT to encourage student and employee engagement in the community, and easily report on metrics for annual reviews. Doing more good is the entire point of POINT (pun 1000% intended).

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1. Pace is Everything. If you’re not moving quickly, it means there’s a problem you need to deal with. When I first started POINT, I hired a development team that took 6 months to wire frame the app (for those of you not in the tech world — that should happen in 1–3 days). It’s extremely embarrassing to admit, even though I was one of the first with the concept I was significantly beat to market. I didn’t know how to navigate the tech sphere, I wasn’t firm with what I needed from the people who worked for me, and I had a massive speed issue staring me in the face that I wrote off as “the process”. So before you start (or as you start) get educated about the sector you’re working in, find the right people to join you and get tough because you’re the pace setter. You need to work fast, hire fast, fire fast, sell fast and pivot fast.
2. You’re running a marathon, not a sprint. Be aware you’re about to run a marathon and you need to prepare yourself for it. I naturally am nocturnal, really, but staying up till 4 a.m. or working 48-hour shifts won’t help you in the long run. Last year I worked 17–19 hour days for 4 months, only sitting at a desk. Sometimes you need to do what you need to do, but you also need to see the sunshine. Make sure that you get done what you need to, but that you also take time to sleep, eat a healthy meal, get some exercise, and see your family.
3. Know yourself, really, really well. As an executive you need to know yourself personally and objectively. Once you know your strengths and your weaknesses you can plan around them, leveraging your strengths and hiring to your weaknesses. How do you get an objective view of yourself, though? I’ve found it works best to do anonymous employee survey of your leadership style and characteristics EVERY YEAR. It’s been one of the best tools in my career. Years ago my employees said my main weakness was communication, now, with persistence, it’s a strength.
4. The pit in your stomach means you’re making moves. The pit in your stomach is here to stay. It means you’re uncomfortable and most likely pushing yourself to keep the pace you know you need to. As a leader, you might naturally believe nothing is ever finished, and your brain is years ahead. You’ll constantly be thinking through a million things to do and directions you could take. I sometimes view my brain as a racket ball court that has 75 balls at play bouncing off the walls at all times. Between the chaotic pace of my mind and the pit in my stomach, it’s enough to keep you in bed forever or push you to wake up early and take on the day. You have to decide what it’s going to be.
   General tips to calming both your stomach and brain: take nothing personally, define (at least) one accomplishment of the day that will help you fall asleep in a good frame of mind, get some sunshine, sweat it out, know the smarter you work — the better you feel, and do something before bed that has nothing to do with work.
5. You’re going to do a whole lot of things you don’t like. I think 75% of my time is spent doing things I don’t like. Me? I like product design. Creating, building, making things functional to solve problems. But day in and day out, I spend most of my time doing everything BUT that. But I know all the little things I don’t like to do make it possible to build the things I want, so I do them anyway.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

The whole reason I started POINT was because I was mad that it was easier for me to use my phone to order ramen in bed or book a room in Spain than it was for me to do something good in my local community. Now that we’ve built a volunteer app, POINT, we aim to inspire people to bring POINT to their own cities and so that anyone, anywhere in the US can know where to start when they want to get involved with a cause they care about.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“You’re never too important. ”

I’ve seen my dad start and run his own companies and he always says the phrase, “You’re never too important.” But he doesn’t just say it, he really means it. When things need to be done, you’ll see him changing a light bulb or sitting at the secretary’s desk when other executives felt it would be a blow to their pride to fill in. Basically, don’t do things if they don’t make sense for the good of the company, but when push comes to shove, you need to be willing to do anything.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Whitney Wolf Herd — You out there? Tacos?

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

About the Author

Phil La Duke is a popular speaker & writer with more than 400 works in print. He has contributed to Entrepreneur, Monster, Thrive Global and is published on all inhabited continents. His most recent book is Lone Gunman: Rewriting the Handbook On Workplace Violence Prevention listed as #16 on Pretty Progressive magazine’s list of 49 books that powerful women study in detail. Follow Phil on Twitter @philladuke or read his weekly blog www.philladuke.wordpress.com