If you look hungry, you'll starve

We were months into a fairly small raise. We had an accelerator-backed startup in a brand new industry focused on a tech that was about to blow up. We had co-founders who worked at Kodak, Deutsche Bank, and HP. We had a crack developer who could turn spaghetti code into something usable on a budget.

We’d walk into the Sand Hill Road offices (I was John Biggs from TechCrunch so we’d always get meetings) and we’d show our product. Two parts of it weren’t connected so we had a great front end and a great back end. We had everything they say you should have.

But we were hungry.

My co-founder wasn’t working. I was supporting three kids on a few thousand a month. My wife wasn’t working. Our technical co-founder, our CTO, hadn’t quit his cushy banking job and he wasn’t planning on it. On paper we were gold. In-person we were trash.

We didn’t raise.

We didn’t raise for a few reasons. We were too early — crypto wouldn’t take off for four years — and we didn’t talk the talk. I didn’t understand what the product had morphed into over time, a common situation when the team isn’t on the same page. And we were hungry.

We walked in expecting a handout. We walked in not asking for a deal but a lifeline. We were looking for someone to save us.

Now the concepts behind this sentiment are deeply sociopathic. The entire idea suggests that in order to make money you have to lie. But, and this is sad, it’s absolutely true.

The best fundraisers are folks who spin gold out of straw. Who raised the most money in recent memory? Noted fabulist Adam Neumann of WeWork. Who is winning in crypto? The folks who can convince a million poor people to invest in shitcoins. Who is going to raise a $5 million seed round? The hustler who comes in asking for $2.5 million but could oversubscribe the round just a little bit for the VC sitting in front of her, just this once.

In other words, you need to create a sense of urgency, a sense of FOMO, real and palpable fear in the necrotic heart of the compulsive gambler. You need to look like the next million-dollar gain not the next $25,000 loss.


Need dev help? I work with VisibleMagic.com. Check them out.


How do you do this? You know your pitch inside and out. You can spill it out like hot soup into their bowls. You pick up the tab, you soft sell to appeal to the crocodile brain sitting in front of you whose only reaction to being asked for money is fight or flight. You’re not Joanna Smith, late of Canton, Ohio, with a BA in English and half a product. You’re Joanna Smith, superhero, future millionaire, who knows her market better than some 80-year-old fool at some dumb bank.

You look the part: you have cool shoes, cool jeans, cool t-shirt. Put on your friend’s Rolex. Look like you’re a secret millionaire.

Further, don’t raise at all. Go as far as you can without talking to VC swine. Bootstrap, build your own product and sell it. See if it works. When you need marketing cash, go in and tell the VC “Hey, Patagonia, this thing works. It’s making $10,000 a month. For a $50,000 investment, we can up that to $100,000 a month. Make it $1 million and we’ll haul in even more. The sky’s the limit.”

If you look hungry, you’ll starve.

This is awful advice in life and it deadens the soul. But you signed up for this world, didn’t you? You wanted this.

If you look hungry, you’ll starve.

In retrospect, it’s all so obvious. Don’t make the same mistakes we all did. Look fat and sassy and wait for the vultures to come in for the scraps of your success.


In this newsletter, I write about startups so I’ll need your help. If you’d like to be featured in the newsletter, please fill out this form. I’ll contact you with my standard set of questions and I’ll write you up and send your info out to all my subscribers. This service is free. 

Photo by Joshua Wilking on Unsplash

Loading more posts…