From Welfare to Millionaire

I’m sitting on my flight back to Seattle and rather than getting in some much needed shut-eye, my wheels are turning again.

I’ve decided to stop trying to fundraise from accelerators, Angels, and VC’s. Sure, I’ve only applied to a handful of things so this may seem premature, but the experience itself has proven not to be for me and after yet another rejection email this morning, I feel free enough to make a shift.

Over the last several months, I’ve gone from experiencing the joy of seeing my real-life fairytale of a company come to fruition, to feeling like a broken down, used up .

The thrill of being able to finally and legitimately use the phrases “raising a round,” “fundraising,” “pitching to investors,” “talking to VC’s” was like seeing a breathtaking horizon that led me into a zombie-like trance in their general direction.

But rather than coming out enlightened, directed, and connected, I am realizing the fatal flaw of early, pre-product-market-fit fundraising – you stop working on what you are good at and what you know, and become more like a prostitute on a crowded and desperate street corner.

Though I’ve never been a “real” prostitute (and truthfully have nothing against someone consensually participating in the field), I had one bizarre close encounter.

At 14 years old, I desperately wanted to fit in. I had been overweight my entire life and due to going through puberty at age 6 1/2, I had a face full of pimples at 7 and a host of other bodily changes that readily allowed my peers to ridicule every aspect of my being.

So I started hanging out with the “wrong” crowd. After all, they were misfits as well and we were collectively disillusioned by our lack of self-worth. One evening, I found myself hanging out with a group of my young teenage friends and some 20-something-year-old guys.

I didn’t have much experience with drugs or alcohol and so when one guy asked me if I wanted to smoke pot, I thought “sure, why not.” That led to an insatiable thirst called cotton mouth and so the kind gentleman very graciously handed me something to drink and told me it was iced tea.

It was iced tea alright – Long Island iced tea. And after chugging that down, completely unaware that there was alcohol in it, I was quite drunk and at their disposal.

The details are fuzzy, but I found myself standing outside at one point in the beach flats of Santa Cruz with my young friend and some older guy. He was trying to convince us to go along with the story he was about to tell to the middle-aged man standing in front of a motel who barely seemed to speak a word of English.

After trying really hard to regain some level of cognitive understanding, I began to realize what was really going on. The 20+ year old guy was trying to sell my friend and I as prostitutes to the Spanish-speaking man in exchange for cocaine. He kept trying to “reassure” us that we weren’t really going to be prostitutes because his grand plan was to stab the man after getting the cocaine and then we would all go off to have fun and party.

Uh…WHAT?!? It was that explanation that shot one potentially life-saving lucid moment through my head: get the fuck out of there. Any way you can. Just get the fuck out.

And so I made an excuse that I was going to barf and just needed to go to the bathroom real quick. It was there that I discovered another young best friend of mine had shown up and after telling her what was happening, we huddled together on the floor hidden by the bed until we found an opportune time to escape.

Now I know you may be thinking that my story has unraveled into a nightmare that has nothing to do with fundraising for a startup. And yes, to some degree, you are correct. But in my case, my life has shown me again and again, that when I try and fit who I am into a box that others will laud, like, and respect, I have lost sight of my unique contribution to this world: me.

Over the last several months as I dabbled in fundraising, I discovered that many many people do not get what I do or what I am trying to build. They do not understand my vision and admittedly, I struggle with trying to clearly explain it. So I tried pairing it down, I tried likening it to other companies, I even tried downright changing what we do and how we do it.

But those were not me, and I will not serve anyone – not even the investors – if I am accepted for what I am really not. I must press on as myself. I did not spend the last nine years building a ship only to steer it to someone else’s promise land.

Most investors – most people – do not have the unique life experiences I have had. They do not know the true joy of a welfare Christmas, the relief of getting “adopted” for a holiday so you can manage to hand your kids a gift, the Thanksgiving dinners in an AA hall because you needed the food and they needed to not drink.

And so they will never see what my vision is – to destroy a corrupt social services system that does not serve the poor but instead punishes them for experimenting with self-sufficiency and calls connecting people with welfare-to-work, Bill Clinton era, poverty-wage jobs “success.”

And that’s okay. And I do not judge them. And I do not envy them.

It has been said many a time that choosing an investor is like getting married. And I want a happy marriage. Someone who gets me. Who sees something deep and powerful behind my often sad and heavy eyes. And until I find that person, that investor-soul-mate, or even if I never ever do, I shall remain happily single and content with being a very mangled shape in a square and circle world.