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Anita Brearton: “Companies never go from A to Z as they planned”

Companies never go from A to Z as they planned. This has been my co-founder’s mantra as long as I’ve known her and it’s definitely true. The start-up journey is very much like the game Snakes & Ladders, progress followed by unforeseen setbacks. You just have to learn to roll with it and have a […]

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Companies never go from A to Z as they planned. This has been my co-founder’s mantra as long as I’ve known her and it’s definitely true. The start-up journey is very much like the game Snakes & Ladders, progress followed by unforeseen setbacks. You just have to learn to roll with it and have a good sense of humor. Our core mission hasn’t changed since we started the company but the product we imagined and what we are selling today are very different. The key to success is in being able to quickly course correct and respond to challenges without wallowing in negative emotion. In the few short years of our company’s life, we’ve had to replace development teams, adjust product strategy, recraft pricing, eliminate partnerships that weren’t working, hire and fire employees and move offices four times. It’s all part of the start-up journey. When you found a company there’s no blueprint to follow. You have to plot your own course and sometimes that means a change in direction.


As a part of our series about strong women leaders, I had the pleasure of interviewing Anita Brearton, Founder/CEO of CabinetM, a marketing technology management platform that helps marketing teams manage the technology they use to acquire and engage customers. A long-time technology marketer, Anita has led marketing teams from company inception to IPO and acquisition. She is the author of the Attack Your Stack and Merge Your Stacks workbooks that have been written to assist marketing teams in building and managing their technology stacks, a monthly columnist for CMS Wire, speaks frequently about marketing technology, and has been recognized as one of 50 Women You Need to Know in MarTech.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

My entire career has been spent working for or with technology start-ups, predominantly in a marketing role. I’ve worked for companies from inception to IPO and beyond. I love just about everything about the start-up experience. Prior to starting CabinetM I was asked to be an interim CEO for an e-commerce company. While I was there, I saw how difficult it was for the marketing team to find the new technology they needed to acquire and engage prospective customers — that problem stayed with me and became the spark for CabinetM.

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

When we started the company, our goal was to make it easy for marketing teams to find the technology they needed to acquire and engage customers. At the time, common wisdom suggested that there were about 500 different technology products in that category so we thought that we’d quickly catalog them and then build a marketplace around that catalog. Fast forward to present day, we now have more than 15,000 products in our database and are still adding more every day; the technology landscape is far bigger than we ever anticipated. It also turned out that finding technology is not the biggest problem marketing teams have. As we did our market validation work, we heard over and over again how marketing teams were struggling to manage the technology they already had. We learned that companies were using 100+ different pieces of technology at any one time to acquire, engage and retain customers. Furthermore, much of this technology was integrated with other pieces of technology creating a very complex technology architecture. We quickly shifted our focus to technology management and as we did that, we continued on with our market validation to ensure we were on the right track. During this time the most interesting meeting we had was with one of the largest digital marketing agencies in the world in order to understand their role in assisting their clients with this problem. We met with a senior VP who quickly confirmed that their client companies were really struggling with their technology management and strategy. When we asked whether they were stepping up to assist in this area the response was “they don’t pay me enough to deal with that.” I can honestly say it has been the only time in our company history that my co-founder and I were both speechless. We walked away from that meeting convinced we were doing the right thing, and as they say the rest is history.

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?

There’s the funny and then there’s the mistake. The funny for us was our complete inability to name our company. We’re two marketers and just couldn’t come up with a name. As a B2B marketer I know that all you need is a name that someone can spell and pronounce but even with that in mind we couldn’t do it. Eventually, I was sitting in a movie theater waiting for the previews to start when “CabinetM” popped into my mind — Cabinet being a reference to where you store things and also to a trusted set of advisors, and M for marketing. I became that annoying person in the movie theater furiously texting my co-founder with the idea. The big mistake I made early on was complicating the business model. Before we’d built the first iteration of the product, I created a model that was so complex that our finance resource had to spend a day reacquainting himself with it every time I wanted to make a modification. The big lesson from that was to keep it simple so that it is easy to iterate. I think that lesson works for a lot of things in a start-up.

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 have been so many people who have gotten me to where I am today. Every founder I’ve worked for or with has had a tremendous impact. But, if I have to pick the most influential with regard to CabinetM, I’d like to call out two. The first, Rudina Seseri, is the managing partner of Glasswing Ventures. It was Rudina who encouraged me to step into a CEO role and then supported me as I navigated the challenges of taking on a company that I hadn’t founded, and that was in need of a new strategic path. It was undoubtedly the most stressful two years of my career, but an incredible experience. The second is my co-founder, Sheryl Schultz. Sheryl and I both grew up in the telecoms infrastructure industry working in marketing roles for start-ups — me inside companies and Sheryl as a consultant. We knew of each other by reputation but didn’t really get to know one another until companies started to bring us together on advisory boards. We each exited our “corporate careers” at the same time and ended up joining the same Angel Investment firm, Golden Seeds. After two years of being members we were asked to consider leading the Boston chapter. At that point, we were itching to get back to the other side of the table. We thought that we might want to do something together but weren’t sure how well we would work together. Sheryl and I are as different personality-wise as you can get — I’m super pragmatic and analytical, Sheryl is super intuitive and creative. We decided to run Golden Seeds Boston for two years to test whether we could work together. The experiment was a success but not without bumps in the road. We had to learn to really listen to one another and to argue our different points of view to the ground without it getting personal. It was the best preparation for starting a company we could have had.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

I’m surprised that the number is that high given that women typically receive only 2–3% of available venture capital. The issue is less about women starting companies (40% of US businesses are women-owned) than it is about women receiving venture funding for their companies. Once we change that dynamic, more women will start venture-suitable companies.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

We need a whole mindset change. Any woman that has raised venture capital will have at least one horror story. I have several. There are investors that are overtly gender-biased (those are the ones that tell you start-ups are too hard for girls), and those that are subtly-biased who may or may not realize that they are holding women founders to a different standard than male founders. For example: studies have shown that VCs typically ask males promotional questions about growth and opportunity and females prevention questions about risks and failure. If the discussion is all about risk and the possibility of failure it will never lead to investment. And then, there are the VCs that are not gender-biased and because of that, find it hard to believe that their peers are. And, because of that, they believe that the only reason a woman hasn’t been able to raise money is because of her pitch or business and decline to invest. All of this adds up to little to no money flowing to women-owned businesses.

I often think that venture would be best served by finding a way to receive pitches blind in the same way that orchestras audition musicians behind a curtain to eliminate bias.

Venture-backed companies have an appalling success rate; 99% of venture-backed businesses fail, so it’s not as if the system is working for anyone at the moment. Change has to come from within the venture community.

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

This answer applies to men and women equally — if you have an idea that you are so passionate about that you can’t stop thinking about it, and you have the expertise to execute on that idea, then consider starting your own company. One qualifier — having a great idea is only the beginning. Before jumping in full time, take the time to do your market validation work to ensure that you are solving a real problem with a product that people will actually buy.

For women specifically, one of the key benefits of founding a company is the ability to create the work environment and culture that you want to work in.

The world needs more women founders; women-led businesses frequently outperform those led by men.

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

  1. Having your own company will give you control over your own time. It’s just the opposite, you will spend every waking moment thinking about your business and more hours than you can imagine working on the business.
  2. Being a founder is glamorous. There is nothing glamorous about being a founder. It’s a lot of hard work and there are plenty of days when the work you are doing is way below your paygrade. We still laugh about the day that we were hard at work on our business model and our VP of Engineering sent us a note to let us know that we were out of coffee and we needed to do something about it. You gotta do what you gotta do.
  3. It’s easy to raise money. It doesn’t matter whether you are male or female, raising money is really hard. It’s 10x as hard for women. Expect to have to pitch 40+ times to find an interested investor.
  4. You will have control over every business decision. Once you take in institutional money you are working for your investors and will have a Board that will hold you accountable for your actions.
  5. You will get rich being a founder. 99% of companies fail and very few exit for large multiples. Wanting to get rich is not a good enough reason to found a company.
  6. Being a founder does not equate to success, it’s merely a title. A colleague reminded me that you are not an entrepreneur until you have sold a product, and you don’t have a business until you are profitable. Those are the real goals that you should be focused on.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

Not everyone is cut out to be a founder and that’s okay. To be a founder you need to be:

  • Comfortable with uncertainty, risk, rejection and navigating lean periods.
  • Ready to work ridiculous hours — not all the time but the days are generally long for a founder.
  • Willing and able to learn new job functions: one day you’ll be dealing with financials and business models, the next day you’ll be managing technology development and marketing. Founders don’t have the luxury of staying in one lane.
  • Willingness to do the grunt work and well as the intellectually challenging work.
  • Prepared to fundraise. This is not a job that can be delegated. Investors expect to see, and work with, the founder. You don’t have to have fundraising experience, but you do need to be willing to learn the process and lead the charge for your company.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Take charge of your board and the board meeting. In my first CEO role, the board kept asking for things to be added to the board deck which I dutifully did until the deck was averaging 70 pages, the board meetings were four hours long, and it was taking a week of everyone’s time to prepare for the board meeting. I finally went to the most senior VC on the board and asked him what his other portfolio companies did and he gave me the best advice: When you build your deck only include slides that are going to be helpful to you in running the business. From then on, my slide deck was between 10 and 20 pages and our board meetings became far more productive.
  2. Don’t over-communicate with your investors. I walked into a situation where the former CEO had been sending a weekly update to all investors. I followed suit and spent Sundays writing the update and Mondays answering questions about the update, which made for an unproductive start to the week. My solution was to acquire technology that created a dashboard that investors could access showing the key metrics for the business. The funny thing was that the investors were perfectly happy with that solution but never actually looked at the dashboard. In my current company we send out an investor update every quarter — it is a factual, not promotional, report that covers accomplishments and challenges. It’s a great way to build trust with your investor community which is critical because you are going to need their help and support in hard times.
  3. Don’t raise money too early. We were talked into pitching an investor group really early. We knew intuitively that it was too early, but the group knew us well and pressured us into coming in. The pitch went well but we crashed and burned in diligence because we just weren’t far enough along to deliver the proof points they were looking for in an investment. And though this group did eventually invest with us when we came back six months later, it was not at the level we wanted; we were definitely tarnished by our first interaction with the group.
  4. Everyone has a hard time raising money. When you’ve pitched 30 times and every meeting ends with rejection it’s easy to start thinking that it’s just you and your business. It’s a blow to your ego and your confidence. It’s so much easier to cope with the frustration and rejection when you internalize that most companies are having the same experience. One of our investors, Glasswing Ventures, has worked really hard to make sure that all the CEOs of their portfolio companies know each other and have an opportunity to communicate on a regular basis. Sharing experiences and supporting one another makes it much easier to accept a rejection and move on.
  5. Companies never go from A to Z as they planned. This has been my co-founder’s mantra as long as I’ve known her and it’s definitely true. The start-up journey is very much like the game Snakes & Ladders, progress followed by unforeseen setbacks. You just have to learn to roll with it and have a good sense of humor. Our core mission hasn’t changed since we started the company but the product we imagined and what we are selling today are very different. The key to success is in being able to quickly course correct and respond to challenges without wallowing in negative emotion. In the few short years of our company’s life, we’ve had to replace development teams, adjust product strategy, recraft pricing, eliminate partnerships that weren’t working, hire and fire employees and move offices four times. It’s all part of the start-up journey. When you found a company there’s no blueprint to follow. You have to plot your own course and sometimes that means a change in direction.

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

My personal focus has been on supporting women in business and particularly women founders. I joined and ultimately ran the Boston Chapter of Golden Seeds, an angel investment group that invests in women-led businesses, started the Boston Women’s Entrepreneurial Council, served as an Executive in Residence in the Simmons College MBA program. I have, and continue to, mentor and support a number of women founders.

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.

It would be around educating and training people for the next wave of jobs in a technology dominant world. I don’t know what that would look like, but it’s area I’m really interested in. We have far too many people without skills that are living below the poverty line that could be helped with the right job training programs.

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.

Without question it would be Ben Horowitz of Andreessen Horowitz. In my first CEO role when I was dealing with some enormous challenges and feeling overwhelmed, I read an interview in Fortune Magazine between Ben and Jack Dorsey of Twitter about being a CEO. It was the perfect article at the right time and completely changed my mindset. I then went on to read Ben’s book, The Hard Thing About Hard Things, which was an honest accounting of the entrepreneurial journey. It’s a book I think every founder should read.

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


This series was inspired by Female Founders First, a program by Barclays and Techstars designed to provide female founders with resources to grow, scale and advance their businesses.

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