Why Do I Have A Love/Hate Relationship With Most Amazing Start-Ups?

I got introduced to the start-up world very early in my career.  I left my first job with a big wall street firm to go work for one of the early start-ups launched by a guy who is now known as one of the most successful serial entrepreneurs.

It was a wonderful learning experience. And since we were a small company, I took part in many pieces of the business.  Something I’d never get to do at a bigger company so early in my career.

I loved my job, I loved the company and the founder’s vision.  I did everything from B2B marketing to business development and straight-up sales to help us grow.  And grow we did.  We also ultimately failed as a company.  It was an eye opener.  I decided to go work for an established company.

I got a great job working in magazine publishing. I remained in that business and grew from sales to sales management over several years.  One day I got a phone call from the founder of a digital start-up focused on the youth market. It was my focus at that time so I had a lot of experience and expertise.  I figured it was worth a meeting since I knew digital media was growing fast.

I met with him and the rest of the (very small) team there and was completely hooked.  I left my “safe” big company job to try the start-up world again.  By this time I had a husband, though no kids so why not?!

It was a fantastic experience.  The company grew from 20 people to over 200 during my time there. And we grew revenue from zero to over $18 million in 18 months.  I got to pitch VC’s, investment bankers, met and presented to Mary Meeker and participated in putting together our S1.  The founder’s goal was to take the company public.

And then the dot com bubble burst.  Ouch.  The company went from 220 people down to 20 in record time. And ultimately it failed. This one was a heartbreaker.  It honestly felt like a death in the family.

I went back to Corporate America and worked for big companies.  The only twist is that I got to work on some start-ups within these big companies which was an ideal combination of building something new coupled with big company security and resources.

My favorite by far was growing Addicting Games.  AG was part of MTVN’s Atom Entertainment purchase. It was a property that many considered the “dog” of the portfolio.  With the help of a small dedicated and passionate team we grew the brand from 7 million to over 15 million unique visitors.  And we grew from half a million in network revenue to over $25 million in brand direct revenue in 3 years.  It became a very valuable property and brand within the MTVN portfolio.

Two years ago I went to my third VC backed, early stage start-up.  It was the first time I worked in marketing tech/SaaS and I have learned a lot.  I learned about marketing and selling a SaaS product vs. a media product.  I learned about SaaS businesses and metrics, social media, social listening and social selling and so much more.  All good!

I joined because I believe in the founder, the product and the board ( the Chairman of the Board had hired me at another company before this one).  And I’m no longer part of the company.  A week ago they decided to let go of all of senior sales and marketing to focus their resources on necessary product improvement.  Another heartbreaker.

And even though I’m no longer part of the company I really do hope to see them succeed.  I want all the time, effort and hard work (in addition to financial investment) to pay off.  I still believe in the product and the people.

So what’s next?  That’s a great question.  I’m still pondering my choices and what I really want to do.  At it’s very core, what I love about start-ups is the collaboration, developing and growing a business, the change, the lack of bureaucracy, the opportunity to learn and the hope and vision of changing the landscape. Creating something that did not exist before successfully.

So where’s the “hate” part?  I hate when they don’t work out, I hate when I put my heart and soul into a business and don’t get to see it come to fruition.  I hate it, but I love all the rest a lot more which makes it worth it to me (either that or I’m a glutton for punishment).

So is another start-up is in my future? Maybe.  Well probably – if I’m being honest with myself.