Monkey Masters: Cotter Cunningham



For my first interview of Monkey Masters, I am thrilled to interview Cotter Cunningham.   It is hard to imagine a better entrepreneur to interview for my inaugural Monkey Master’s blog series than the one and only Cotter Cunningham (full bio at the end of the interview).

Cotter is a larger-than-life character whose career is nothing short of spectacular.  Cotter is the rare example of an entrepreneur who can start with an idea and turn into a billion-dollar public company.  Cotter did just that with Austin-based RetailmeNot – an amazing entrepreneurial story and journey.  Now he spends time helping other entrepreneurs as an investor and advisor – and notably serves on the Entrepreneur’s Council for my firm, Next Coast Ventures.

Cotter is also one of the nicest humans in the world.  I hope you enjoy the first version of Monkey Masters!

I am excited to share his interview with you! 

Why did you decide to become an entrepreneur?  What 1-2 things from your life, your upbringing or professional experience drove you to eventually take the plunge into the great unknown?

So I was a reluctant entrepreneur. I had previously considered “the leap” but had always backed out of doing something – mostly around fear of failing and not having enough savings to fall back on.  Eventually, I just decided that I had enough in the bank that my family could make it for a while. And I truly hated my job at the time. So I think the combination of having a safety net combined with the push of not liking what I was doing was enough.  

I was also lucky in that I had some great role models. My Dad was a small businessperson, my mom owned a tiny business, my inlaws were both successful self-made business people. I knew what I was getting into.

What mental hurdles held you back and how did that manifest itself in your leadership/decision-making/personal well-being? 

I put myself through grad school and I had a lot of debt coming out, so I opted for the safety of a salary. At the time I didn’t realize that there’s no real safety in working for someone else. Over time we had a family, bought a home, etc. We grew dependent on my income.

I admire any entrepreneur (period!), but I especially admire people that choose to do something at a point in their life when they have a lot to lose. I had three kids and a mortgage – I had to make it work. And I was terrified that it wouldn’t. Fear can be a good motivator, but it can also be bad – both from a physical standpoint and also for decision making. Part of being entrepreneurial is risk-taking. If you are worried too much, it can make you too cautious – which is the worst! 

What one piece of advice would you give to your previous self when you were first starting out?

 Trust yourself! One example: I wanted to make a particular acquisition and I let a few colleagues talk me out of it. Huge mistake! It would have been an amazing combined company. I think too often I worried about building a consensus vs leading. You are the CEO. Lead. 

What was the biggest surprise for you about being an entrepreneur?  What do you know now that you wished you then?

I believe that the first 5 employees you hire in your startup will set the culture for the next ten years. Pick well! 

Who are your entrepreneurial (or life) heroes?

My Dad has dedicated his life to making the little town I grew up in, Helena Arkansas a better place. I think he has easily spent 30-40,000 hours working on initiatives involving political and business improvements for eastern Arkansas. 

I have a voice in my head that fills me with fear, uncertainty and doubt. I call him Mr. Monkey.  Do you have a voice like him? How does he try and screw with you? How do you quiet him (or her or it) down?

I haven’t named it (yet!) but I definitely have self-doubt. One thing I learned the hard way is you need to believe in yourself and you need to have people around you that believe in you too. I had a boss earlier in my career who said all the right things to my face but his actions clearly indicated the opposite. I waited around too long trying to swing him to my side. Life is too short to work for someone who doesn’t believe in you.

A huge thank you to Cotter for participating in Monkey Masters! Be sure to be on the lookout for my next interview and all future blogs here

AND if you haven’t yet… be sure to take The Entrepreneur Survival Test and test your skills. 

Cotter Cunningham full bio (linked in here)

Cotter is currently serving as an Entrepreneur-in-Residence with Next Coast Ventures. Prior to this, he was the founder, Chairman and CEO of RetailMeNot, Inc., a leading savings destination that enables brands to engage active shoppers and influence purchase decisions. Cotter founded the company in 2009, made more than 15 acquisitions, and raised more than $275 million from investors that included Austin Ventures, Norwest Venture Partners, GV, IVP and JP Morgan before leading the organization to an IPO in July 2013. In 2017, RetailMeNot was acquired by MacAndrews and Forbes. Through these efforts, Cotter has made a significant impact on the technology business environment in Austin, Texas and has saved millions of consumers billions of dollars across the U.S. and beyond. On Glassdoor, one of the world’s largest job and recruiting sites, Cunningham achieved an approval rating of 91% based on employee feedback, making him one of the top-rated CEOs in the U.S. Giving back to the community was foundational to RetailMeNot’s culture. The company supported a variety of organizations including ADL, Literacy First, Boys & Girls Clubs, KIPP, Andy Roddick Foundation, Blue Santa, Ballet Austin and Central Texas Food Bank. 

Before RetailMeNot, Cotter was a CEO-in-Residence for Austin Ventures. He also previously served as the Senior Vice President and Chief Operating Officer of Bankrate for seven years, taking the company public in 1999. He wrote the book “Your Financial Action Plan: 12 Simple Steps to Achieve Money Success.” 

Cotter holds an MBA from Vanderbilt University and serves on the board of directors for Waterloo Greenway, the President’s Austin Innovation Board at the University of Texas as well as several private companies. 

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