Katie Wilson: “You’re going to need other people’s help and advice, so find someone you trust with experience and expertise who can help you learn and avoid many of the mistakes others often make”

It would have been nice if someone had told me how low the lows can really be. There are times when all I want to do is just hide under my bed or times I just cried alone uncontrollably for hours. Now, I’ve read books about Silicon Valley and the low times that come with […]

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It would have been nice if someone had told me how low the lows can really be. There are times when all I want to do is just hide under my bed or times I just cried alone uncontrollably for hours. Now, I’ve read books about Silicon Valley and the low times that come with being a founder, and I wish I would have known just how real it is, and that I could’ve built a community of other people who had experienced these same lows.

As a part of our series about strong female leaders, I had the pleasure of interviewing Katie Wilson. Katie co-founded TapOnIt with her sister Sara Castillo in their home state of Iowa to help bring customers to small businesses while providing them with an easy way to save money. Katie’s passion to serve small businesses inspired her to create TapOnIt to support local communities through simple visual text messages. As the digital landscape evolved, Katie realized how important it was to preserve small-business culture in cities across America, especially as large e-commerce platforms continue to grow taking potential funds out of local communities. Katie was named one of Editor & Publisher’s 25 Under 35 People to Watch, DMN’s 40 under 40 and her digital program was named one of the top ten in the country.

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?

Prior to starting TapOnIt, I worked in the newspaper industry where I had the opportunity to work with all sorts of businesses, everything from mom and pop shops to nonprofits and universities. I was the digital advertising director at a time when digital was emerging beyond the early banners, social media was growing, Google was gaining traffic, Groupon launched and traditional media was changing. It was a confusing time for small businesses — with limited resources and expertise I loved helping them build campaigns that would grow their revenue. Texting was starting to become more mainstream and I saw a huge opportunity in the text messaging space. Texting has been around for 25 years and is now such a routine part of our lives, yet up until recently, there has not been a whole lot of change. The fact that brands were communicating with consumers with just black and white texts with no images, I just couldn’t understand why we weren’t being more creative. Most people are visual, your brain processes images faster than words. Putting creative graphics to those texts that people have agreed to receive just made sense. So it was back in 2015 that I left the newspaper to start TapOnIt, ready to help fix what I saw was broken in the text messaging space.

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

In August of 2017 I received several calls from some female business colleagues of mine. They said I just had to come to our local annual Chamber of Commerce dinner to see the keynote speaker. Busy with our startup adventure, my sister (Co-Founder) and I hadn’t planned on attending that year, but their plea was compelling so we put our black dresses on and went.

From the minute the Keynote speaker took the stage, we felt like he was talking directly to us and understood exactly what we were trying to accomplish. That speaker was Bonin Bough, former Marketing Executive for Mondelz and author of the book Text Me.

After so many people telling me that no one would sign up to be texted pictures of ads, there Bonin was speaking about the importance of messaging and brands reaching consumers in a more personal way. Those colleagues that prodded me to go to the dinner kept saying see Katie — we knew you had to be here tonight. But it was what I did after dinner that changed so much for me personally and the life of our startup. Bonin will say I chased him down like a crazy person, but like any professional, I waited for my turn in the Q&A session, and I asked him if I could get 15 minutes of his time because we are a text messaging company in the Quad Cities doing exactly what he was talking about.

Bonin and I spent the next two hours talking, and ever since then, he has been a massive supporter of TapOnIt. Bonin now includes us in events all over the world that open doors and make connections. He is now a close friend and someone who has a major impact on me personally. It’s crazy to think that if would have stayed home that night and not gone to the Chamber’s dinner, I would have never met him. It taught me a valuable lesson: never be afraid to ask for what you want because the worst someone can say is no.

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?

Well I have learned a ton of lessons and have made a lot of mistakes. Growing up in the Midwest made me a very trusting sole. I hired this guy to sell for us and thought he was going to be great. About two weeks after he started he stopped showing up. Unfortunately I had given him a key to the office and a laptop computer. Finally after a few days of trying to hunt him down, I had to fess up and call our landlord who was also an investor. I explained what had happened and we both agreed we needed to change the locks. What I didn’t realize is that I had given him the master key to all of our landlord’s buildings and offices. We laugh about it now but every single building, every apartment and business he owned had to be re-keyed.

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’m not sure I was ever attracted to the idea of being a CEO, or an executive. That wasn’t the mindset that got me to where I am right now, it was that I had an idea and that I wanted to start a company. I wanted to be a founder and to build a successful company, and the position of CEO is what allowed me to do that. I love that it gives me an opportunity to be involved in all aspects of the business — from development to sales. I love that I got to build out the initial vision for TapOnIt and have an impact on driving people into local businesses. Recently we pushed out an offer for a pizza chain in Oklahoma City and over 1,000 people texted it to their family and friends. It is great to see how what we have built be the reason consumers shop in their community or try a restaurant — I love how instantly we can see the results for local businesses. Watching what you have built is so exciting, but we have so much more we want to accomplish.

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

A CEO of a startup tech company does everything — it is much different than a CEO of a company that has been around for years. My CEO role changes as we grow — initially when we were proving out the model I did a little of everything — selling, designing ads, collecting money, payroll — anything we keep the company moving forward. Now that I have a leaders on my team, I can step back and focus on advancing our technology, meeting with investors and national brands and building the framework for our future.

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

I love watching my company grow. In the beginning, there were only three of us, and now we have over 20! It makes me so proud to know that we’ve created jobs that help support our employees families. Nothing is more rewarding than seeing the company change, grow, and impact lives. It can be scary and hard at times, but I am so proud of the team that we’ve built that I am willing to work the long hours and go through the hard times just to keep growing this company.

What are the downsides of being an executive?

You are responsible for everyone else. It’s the opposite side of what I enjoy most. Sometimes it’s scary; you don’t know what will happen next and your job is to make sure that things keep running smoothly. It’s an executive’s job to make sure there’s money for the company and that your employees get paid, so they can put food on their table. There’s a lot of responsibility and lots of people’s families are depending on you.

There can also be a lot of hard conversations. Being a leader means learning and taking constructive criticism and constantly trying to improve. Sometimes that criticism is hard to hear or can be upsetting. I try to remember that at the end of the day my goal as a CEO is to learn to a better leader and executive. It helps me put the criticism into perspective and use it to better myself.

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

That traveling all the time is fun. Sometimes it is, and I don’t want to complain because I do get to do awesome things. But the goal right now is to grow the company, and that means I am not at home with my kids (and my dog) all the time. It can be stressful, exhausting, and hard on your body, but in order to keep things moving in the company, it’s necessary. Especially being based in Iowa. People think that founders and executives get to go cool places all the time and it’s always fun, but most of the time being on the road is just exhausting.

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

When I first started TapOnIt, I had people tell me that it was a “cute idea” or that “it’s impressive that you’ve made it this far.” I’ve had people say that there’s no way that a female-founded tech company from Iowa is going to succeed. When it comes to start-ups and raising money, or having conversations with big brands, men can get away with asking for things while women have to be careful not to come off as “bold-hearted” or a “bitch.” Excuse my language. It’s not as though that’s what we’re trying to be, it’s that women are just as confident and capable to run a company as men.

I dealt with that a lot more in the beginning, but since we raised our first round and stepped on the gas for growth, I’m not experiencing that frustration as much. It makes me happy that as a whole, there are more men in boardrooms standing up for female businesses and helping them to grow. To a certain degree, women struggle in this industry just because they are women, but it’s encouraging to see that things are changing and moving in the right direction.

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

I thought everything would happen so much faster. You build a proforma with all the projections for how your company is going to grow and all the things you need, but everything ends up taking so much longer and costs so much more money than you could ever imagine. When I started this journey five years ago, I thought the growth we’re experiencing now would have happened two years ago.

I also thought I would be doing what I love and am good at all the time. I love a good portion of what I do, but there are also a lot of jobs that I have to be involved with that I’m not good at and don’t particularly enjoy. I’m not going to lie, working on a pro forma and accounting is not my favorite thing to do. But I’ve gotten good at it because I had to, and I learned a ton along the way. As you grow you add people to your team who can take care of the other stuff so you can focus on what you love and are good at. In my case, I love sales and talking to business owners and communities. But in order for me to get to do that, I have to do all the hard stuff too.

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?

Part of being a leader and being an executive is learning to delegate. That’s is really hard to do when you’re used to doing everything yourself or you have the “I can do it myself” mentality. I can tell you from personal experience founding a company, growing a team from small to large, learning to let go to a certain extent can be very hard. So if you are a person who tends to be a perfectionist or be tends to be overly controlling, I truly believe that it’s gonna be harder to build a team that should be helping you to do many of those jobs. If you just try to do it all yourself, your company is never going to grow and the people around you will never learn.

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

Believe in yourself and ask for what you want. I would also encourage women to support other women. I have a very strong network of women that want to see me succeed. Build a team that you trust, so that when things do get difficult, you can break through it together and reach your goals.

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?

Obviously my mom, and I’m sure that almost everyone says that. My mom has always been resilient. She’s always been strong and has always been there for me and my sister. She took care of my kids when I couldn’t, cooked when I had too much work and was by my side through every challenge I faced. Without her help and support, TapOnIt wouldn’t be here today.

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

I don’t think I’ve done anything world-changing yet, but right now I’m at the community level trying to make things a better place. And not just my community, but dozens of different communities. It is so important for America to keep local businesses open and thriving. Local businesses are what make our cities special and unique. I love Amazon and the rest of the internet, it’s easy and convenient and can bring me whatever I may need. But any money not spent locally is money that doesn’t go back into your community.

It doesn’t matter if you’re eating at a local restaurant or grocery shopping at Walmart or Target, they all bring money back into your community in the form of taxes and jobs. The people that these local businesses employ also put money right back into the community. It is just so important to focus some energy off the internet and convenience. We need life experiences! We need to interact and meet people! I have worked hard to support local economies and make sure my children grow up in a world where they can shop at local boutiques and have lunch at the local sandwich place. All of that is incredibly important to me, and it has a huge impact starting at a small scale.

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

  1. I wish someone had really made me understand that things take way longer and cost much more money than you imagined, it would have made the first few years running the company way easier. I built a proforma and raised money, but in reality, it all took much more time and effort than I imagined. You quickly realize it’s impossible to operate in normal nine-to-five schedule when you’re running a business! It would have been incredibly helpful if someone had warned me how hard I would end up working on this company, more than anything else I had ever done.
  2. It would have been nice if someone had told me how low the lows can really be. There are times when all I want to do is just hide under my bed or times I just cried alone uncontrollably for hours. Now, I’ve read books about Silicon Valley and the low times that come with being a founder, and I wish I would have known just how real it is, and that I could’ve built a community of other people who had experienced these same lows.
  3. I wish I had known how important it was to build a community of founders who have experienced the same things. There are hard times, and there are good times, and you will want to be around similar people who know what it’s like to experience those moments with. It helps fight the loneliness that comes with being at the top.
  4. People should understand that while the lows are really low, the highs are amazing. Building something that helps other people, watching your ideas grow and have people support it, is incredible. Yes, there will be terrible lows, but those highs are so high that you just have to keep them in mind when you’re struggling. You have to remember that something bad happening in a day doesn’t have to ruin your attitude moving forward. As long as you celebrate those wins so much larger than you contemplate those losses, you’ll be doing good.
  5. You’re going to need other people’s help and advice, so find someone you trust with experience and expertise who can help you learn and avoid many of the mistakes others often make. I know that I made a lot of mistakes in the beginning, down to how we were using Quickbooks. If someone had made suggestions based on their experience it would have saved us a ton of money and a ton of time. Find the right people to work with, it’ll prevent you from extra work and save you a lot of extra money later.

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.

We are already trying to inspire a movement. It may not be stated that way, but we are trying to inspire people to spend money in their communities and focus on local businesses. I know there are a lot of other companies that do this, like American Express and their shop local campaign, but it’s something that needs to happen all the time, not just around the holidays. Spending money in your communities is what creates jobs, and those people getting paid is what helps to feed the economy, and the taxes collected get put right back into the community. Shopping local is what keeps the whole ecosystem moving, and it would be devastating to lose such an important part of the American economy.

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

My favorite life lesson quote comes from Dolly Parton, who said that, “If your actions can create a legacy that inspires others to dream more, learn more, do more, and become more, than you are an excellent leader.” I’ve had great leaders in my life who have pushed and inspired me to become the best version of myself, so I know how true this quote is. They helped me take the leap and start my own company and realized that I could be a great single mom to my kids. I try to keep this quote in mind every day, because I want to be like the many leaders in my life who influenced me. It’s a daily reminder to aspire to be your best self, and push others to find their best selves

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

I would love to have a conversation with Ashton Kutcher, mainly because he’s from Iowa and has a lot of influence in the tech world. As a female-founded tech company in his home state, I think that he’d see us as the type of company he’d want to invest in after he sees what we’re doing. Go Hawks!

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

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