Who Takes Crazy Risks in Their Dreams?!
There’s this in-between state of consciousness during sleep where you can sometimes recall parts of the dream right before you wake up. I experienced that several weeks ago where I remember wading about chest high in a large infinity swimming pool, set high in a bright and sunny tropical mountainous backdrop, maybe somewhere in the Caribbean. I noticed in my periphery that there were a number of bold multi-colored beach umbrellas contrasting the white sand spread along the pool.
The pool I started out in overflowed on one side like a waterfall into another large body of water about a hundred feet below. Knowing there was water below, I gave into to the current and free-fell down with the cascading water, remembering the feeling of the adrenaline rushing during the free-fall. I did this two times in two different pools in the dream. The third time, I specifically recall not checking to see if there was another body of water below the top pool I was in. By the time I free-fell out of the pool above to what I thought was water below, I found out too late that I was falling towards dry land a hundred feet below!
It was too late to do anything and I felt absolute fear as I was about to hit the dry land below. The moment I was about to hit, I suddenly woke up, trying to figure out in that first split second on whether or not the dream was real and if I was paralyzed.
Despite almost having a heart attack as I woke up, I couldn’t help think about how vivid and real that dream was for the next couple of days. I couldn’t shake the fact that I didn’t even check to see if there was another pool or body of water below the last one. That really bothered me and I started reexamining my risk tendencies about life and entrepreneurship.
The dream made me think how I approach risk-taking in my startup journey. Have I been jumping off into the deep end over and over again without any regard to the amount of risk I’ve been taking? In many ways, it certainly feels like that. As a first time founder, this metaphor and the “drinking from a firehose” metaphor are often how I feel.
However, I do question if the risk I’m shouldering for my startup (as well as my family), is too much. As I’m currently in the midst of raising my first round of funding, what’s been at the forefront of my mind as I go into my pitches is, “how can I mitigate as much risk as possible for my potential investors?”
This is the reason why I’ve waited as long as I possibly could before asking for investment from others. I’ve bootstrapped this endeavor until I simply couldn’t continue shouldering all the needs of the business alone. I’ve tried to make as much progress as possible until it was clear that I needed to start bring in others.
As I go through this fundraising journey, it’s absolutely essential that those who I ask to invest into my startup is that they trust me and believe in me. If they didn’t, they would have never committed to investing. I also trust them, which is why I initiated those meetings (preferably in person and over coffee) in the first place. I trust that they will have my back but also challenge me with where I’m taking the business. They have skin in the game and will keep me in check because their dollars are on the line. Ultimately, this community makes the journey more viable, enjoyable, and accountable.
That means no more free-falling with cascading water until I check and am certain there is water below.
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