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AdTech Reboot

10 Apologies I Will Never Again Make as a Startup CEO

Picture of Judy Shapiro

Judy Shapiro

Editor-in-Chief at The Trust Web Times
Picture of Judy Shapiro

Judy Shapiro

Editor-in-Chief at The Trust Web Times

As published in Entrepreneur

My unlikely journey of launching an ad-tech startup is almost a Dickensian tale, with false starts, misfires and more disasters than most ventures can be expected to survive. It’s been a long journey from initial inspiration to the successful creation of a live system and beyond.

Probably one of my biggest mistakes was a misguided attempt to follow in the typical path of tech startups: hanging out at meetups, applying to every incubator and funding platform I could find and flying to San Francisco so often that my frequent-flier miles qualify me for a trip to anywhere. 

Truth be told, I failed to gain traction in Silicon Valley. I don’t fit the West Coast tech-entrepreneur mold because I am not a programmer but (gasp!) a marketer. When I pitched investors, I consistently saw a puzzled look on their faces. My online venture, engageSimply didn’t fit in easily anywhere. It was the proverbial round peg trying to fit into square cubbyholes — clearly marked either media, ecommerce or mobile — that I imagine venture capitalists use to organize startups. 

My company offers an online engagement network that is a collection of high-interest, topic-based community websites where companies can advertise to consumers who are actively interested in their products or services. 

Those initial California meetings proved excruciating and frustrating for me and the potential investors. My company wasn’t a “scale” venture like they were used to and to add insult to injury, it focused on evolving marketing not disrupting it. As I tried to conform to investor expectations, my pitches became laced with explanations or “apologies” about what my company was not or why it did not. 

I carried on, sustained by a few true mensches, who supported the venture despite every likelihood of failure. My company received enough angel funding to create our vision with a beta launch and paying customers. Each milestone hard won. 

This stands in contrast to the “normal” track, whereby an entrepreneur receives enough angel funding to create a minimum viable product as a demo so as to seek a large Series A fund round of, say, $2 million to $5 million (to then figure out how to evolve that product further to earn real revenue).

Now my company is at a new stage, having earned enough revenue to be able to add staff and grow further. It is sweet to be here.

So in the spirit of the moment, I will finally let go of the burdensome list of apologies I have made these past months to explain why my venture is different. I will never again apologize for the following: 

1. Being a woman in a decidedly male-dominated tech world.

2. Starting a venture as an older woman yet not being a serial entrepreneur.

3. Being a marketer starting a venture who doesn’t code or hack or even care what a growth hacker is. 

4. Being deeply concerned with creating value for all stakeholders involved with marketing technology: the advertisers, the ad agencies and “Judy Consumers” — and not one group at the expense of another.

5. Being willing to operate using ad agencies even though it takes longer and is eminently more complicated. While tech companies (and their venture capitalists) prefer selling to advertisers directly to make sales go faster, this adds more fragmentation to an already fragmented marketing landscape. My company’s use of agencies may take a little longer but ultimately it serves clients better as agencies can operate efficiently as a strategic “mission control center” for their advertisers.  

6. Being totally transparent with advertisers and agencies about how my company makes money and which technology is used (no white labeling here).   

7. Not offering a “disruptive” technology. (My company offers a marketing system meant to help companies solve business problems. Being “cool” is not the point.)

8. Not being dazzled by mysterious digital impressions but working to deliver to companies real consumers whose real behaviors can be interpreted as real intent (to purchase).

9. Not having a presentation that can be explained in 10 slides. (Sorry, new marketing models are not that complicated but they do require more explanation to fully appreciate.)

10. Not being what investors expect me to be but remaining true to who I am. 

In the end, my not “fitting in” was probably the best thing to happen to my new venture. I didn’t give away the farm to raise money — and because the company is composed of marketers, we all know how to make $1 look like $10.

Most important, though, being an outlier freed me from the tyranny of typical tech-venture thinking so my company could create something as expansive as my vision. And it has taken me far without the my ownership stake in the company being diluted. 

I don’t know how this journey will end but one thing is certain: I will never, ever again have to apologize for who I am.