The Wall Street Journal 'Top 50 Startup' With The $43m Funding Round

MaryAnn was a publishing executive before becoming an entrepreneurMaryAnn Bekkedahl is the co-founder and president of New York-based Keep Holdings, a Wall Street Journal Top 50 startup that has raised $43 million in Series A funding. Keep Holdings operates three web services focusing on email management, ecommerce, and advertising.

Formerly, as the EVP, Group Publisher of Rodale, MaryAnn ran advertising sales for all media at Rodale Inc., the leading global magazine and website publisher in health and fitness content. MaryAnn was named Adweek Media’s “Publishing Executive of the Year” in 2009. She has earned spots for her brands on the prestigious and highly coveted trade lists including AdWeek’s Hot List, and Advertising Age’s A-List.

min magazine named MaryAnn one of the “Most Intriguing People” of 2004, Gotham magazine named her one of its “40 Under 40” in 2003, and Advertising Age named her a “Woman to Watch” in 2003. 

We spoke to MaryAnn about the lessons she learned during the fundraising process; the growth of m-commerce in the US; and why she doesn’t believe that women should assume male characteristics to succeed in business.

TNW: Tell us about your $43m fundraising round. What were the key lessons you learned from the fundraising process?


VCs bet on the jockey, not the horse. The 'jockey,’ of course, is the founder and leadership team. The ‘horse’ is the idea they’re building towards.

History shows that original ideas change time and again (pivot) at start-ups; it’s most important to know that the leader(s) can manage that change well and build value for the investors. It’s just as important to showcase the leadership team’s strengths and experiences in investor presentations, as it is to detail the product vision and its eventual grand success.

TNW: With the US leading the way in terms of mobile usage and over a third of people buying things from their phones, what impact do you think the growth of mCommerce will have on eCommerce in the States -  and the rest of the world - in the coming years?


Mobile commerce will have a huge impact on eCommerce, and of course, on brick-and-mortar offline commerce, as well. 

The convenience of shopping anywhere/anytime is simply too irresistible to deny. Today, most consumers browse on mobile, and then execute the purchase on their desktop/laptop, but I see that evolving to even more purchasing on mobile as retailers and payment systems adapt to catch up with consumers’ enthusiasm for shopping from the palm of their hand. 

TNW: What is your business model?

MB: TheSwizzle is a free inbox organizer designed to help consumers manage the commercial communications with brands in their lives. Users can easily unsubscribe from no-longer-wanted email subscriptions, and roll up the subscriptions they do want into a simple daily digest. They can also browse our Gallery of 1,200+ retail newsletter subscriptions to see current deals and product news, and easily add brands of interest into their daily digest. Our business model is an affiliate sales one. When a user clicks through an email from our Gallery, we earn a commission on the products they buy.

TNW: What do you think could be done to increase the number of women entrepreneurs?

MB: I think it’s important for entrepreneurs on the Internet to have a basic level of technical knowledge so that they can broadly scope the feasibility of their ideas, work knowledgeably with their technical peers towards execution, and attract talent that respects their technical chops as well as their leadership and strategic capabilities. Thereore, I think encouraging women to take technical courses in college (or high school) is a great first step towards increasing the number of women entrepreneurs. I also believe that catching women while young – and therefore not yet saddled with financial responsibilities – is a way to increase the number of women in the entrepreneurial world. 

Women are practical. Once they have mortgages to pay and mouths to feed, they’re likely to lean towards more traditional, secure positions. Catch them early!

TNW: What are the advantages of gender diversity in a start-up? Are there any disadvantages?


I think a start-up with a product that intends to serve and delight any audience, needs to have that audience on its team. 

If you’re building a communications platform for teens, you better have some teens nearby to give input and poke holes in your plans. And most consumer products have women in their target demographic, so having women on the team provides a first-hand “gut check” and market research to help guide the product development and marketing. Especially since most developers are men – it’s careless to build a female-oriented product without close contact with women who’ll help guide them through the user experience. I can’t think of any disadvantages to gender diversity!

TNW: What is your top tip for balancing motherhood with a career?


Get over the guilt. Most women in the world work. 

Just because perhaps you don’t “have” to for financial reasons like the gas attendant’s wife, doesn’t mean you don’t have to for fulfilment of your own. I’ve never understood the mothers who sacrifice the challenges and thrill of a career so that (in their minds) their kids can have a better shot than them at achieving the same. Why should that privilege skip the mother?

And tip two – share everything about your job with your kids! What your company’s goals are, how you did each day, what happened at the office, what milestones have been achieved. They’ll love being a part of something that’s so important to you.

TNW: Do you lie awake at night sometimes thinking about the company? What aspects of it specifically keep you awake?

MB: I lie awake every night of my life thinking about my company. I did so less when I worked at a traditional corporation, but even then, I was 100% committed, and “always on.”

As an entrepreneur, your company is so fully intertwined with your life. You own it. You have limited resources, limited time to succeed. 

Every minute of thinking, planning and executing is valuable. Specifically for TheSwizzle, I spend most of my time thinking about how to acquire new customers at scale without massive marketing spend, which I cannot justify.

TNW: What has been your biggest challenge throughout the history of your company, from planning to funding and execution, and how could others learn from it?

MB: Perhaps others at my company would answer this differently, as I’m sure we all feel challenged in different ways at different times. For me, the biggest challenge has been the long stretches of time (weeks) between major feature builds or consumer acquisition spikes. Innovating takes time, and the valleys where nothing SEEMS to be happening (while the developers are heads-down building, for example) can be very difficult. Then again, I’m a bit of a “milestone-junkie,” and need the thrill of success hourly to keep me sane!

TNW: What is one lesson about leadership you learned from a boss or mentor?

MB: In my traditional career prior to becoming an entrepreneur, I was a typical “top-down” type leader who set the vision, laid out the strategies, and delegated execution to team leaders and their subordinates. The culture where I worked very much emphasized the value of experience and seniority, and leaders made big decisions, and then oversaw their progress. 

My mentor at Keep Holdings, Scott Kurnit, has a completely different leadership style that I try to adopt as often as possible:  

Hire excellent people, empower them with full accountability and then let them make all the decisions independently, encouraging them to seek input from those around them as they go. 

This style certainly gives people a strong sense of ownership of their work – which ALWAYS motivates their best work, often derived from long hours, sleepless nights and incredibly passionate output. The drawback I see to this leadership style is this: because the more junior person doesn’t always have experience in what they’re doing (most start-ups are inventing, after all!) they can take much longer when working independently and without experienced guidance. And their final result – while passionately developed and delivered with pride – is not always good enough. Leading them from their best work to the best product for the company requires delicate management, and more time.

TNW: Do you believe it is better to find customers then funding or vice versa?

MB: Customers. Without doubt. 

No amount of investment can buy customers if your product itself can’t earn them. And with customers, funding follows easily.

TNW: What is one lesson you would like to pass on to other women leaders?

MB: I believe that everyone should use their natural powers of persuasion, their passion, and their unique personalities to their best professional advantage. I am not in that camp that says women should act like men to succeed in a man’s world. At all. 

I see a lot of women put themselves into a disadvantageous situation by demonstrating culturally “female” linguistic styles at work that in my opinion, get better results outside the office. 

What do I mean? The valley-girl question mark at the end of each sentence – it may be cute at the bar, but it screams of uncertainty at the office. The flirty interactions with men which can be fun, of course, but I’ve yet to see them generate respect from those men, or the observers around them. Opening each presentation with a joke or self-deprecating anecdote – why, again? Lead with your smarts.  

I am so impressed when women command a conference room, a conference call, a board room or a packed auditorium with their straightforward, educated, and knowledgeable presentations.  

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