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Trying to Hack It

Two Months of the Struggle: Prelaunch, Unfunded and Hungry

I wrote my first post when I still had a glimmer of hope that the “cavalry” (whether in the form of angels or VCs, an incubator or some amazing beta customers) would come. 

I now realize how naive that was. 75 days later, I have made virtually 0 progress with the aforementioned “cavalry”. That said, here’s a recap:

The Ugly: fundraising sucked. Despite going through over a dozen meetings, I didn’t get anywhere, and my personal experience is that even angels aren’t funding anything that doesn’t have real traction: by that I mean real users and/or paying customers. Caveat: depending on your background (for example, if you are an ex-FB or Google engineer), your experience may differ. 

The Uglier: about 50% of the potential investors I talked to were polite, but ultimately unenthusiastic given that I don’t have any real traction – at the very least, they tried to offer constructive criticism. which I appreciated as best I could. About 25% of the remainder were “on the surface” also polite, but let’s be honest, they were more interested in checking their email on their phones while I was desperately trying to convey the details of my life’s work in 15 minutes. The remaining 25% were just critical and did their best to persuade me why my idea was terrible, often making directly contradictory arguments in the process (for example, trying to convince me that there is both too much competition, but no market for what I’m doing). I usually walked out of those meetings dejected (and a little angry).

The Good: despite the fact that I have no funding, no team and no traction, the good part about this whole process is that I’ve put in 60 days of hard work. I’ve coded every single day (over 10K LOC during this time). I’ve made a few solid connections. I still have money in the bank, and despite getting to the brink half a dozen times, I’m too stubborn to quit. At least not yet.

Key takeaways:

Traction trumps everything. I always knew that, but held out naive hope that I might be able to convince someone to take a chance on my startup (pre-launch) because I’m special. Nope.

Just launch: I should have launched a month ago. Instead I built a lot of cool, but unnecessary features and still have 0 users. Whoops.

Rome wasn’t built in a day: when I read about startups getting funded in TechCrunch, I envy them. But most of the time, I also notice that they appear to have gone through a struggle (ie. for example, I see on CrunchBase that that Company X was founded in Dec 2012, and didn’t raise a seed until mid 2013). Like fireworks, the media likes to display winners as they rise to glory, but also like fireworks, the ratio of preparation time to “glory time” is something like 100 to 1. 


March 1, 2014

I was a $200K VC. Now I’m a $0 Entrepreneur. First thoughts.

This is my first post. 

I’m writing this because there’s a lot of widely read blogs from people who have had amazing success, but very few from people like myself, who are starting from the bottom. 

My background: I used to have a cushy, well-paid VC job at a nice office, an assistant (not mine, but the office’s), an expense budget and nice looking business cards.

Now, I work out of coffee shops, and it feels awkward when they recognize me, because I’m there like EVERYDAY. I know where all the free wifi spots in the city are. I also know exactly how long my bank account will be greater than $0, unless I get funding. When I go to parties and people ask me what I’m doing, I put on a brave face and smile and tell them about my startup, and wonder if they can tell that I feel VERY uncomfortable about not being the [insert respectable job title at respectable company here], and now am a pre-funded entrepreneur.

I’ve thought about a lot of ways to describe my situation: it was the best of times, it was the worst of times. Coldplay’s Viva La Vida (I used to ruleeee… these streetsssss…).

I want to keep these posts short and sweet. TLDR: being a pre-funded entrepreneur SUCKS in a lot of ways, but I’m pretty sure if I ever “make it”, I’ll look back on these days with fondness as the best time I ever had, and a big reason I’m writing this blog is to capture these moments. 

If anyone out there is in a similar situation, I want to share a few things I found very inspirational:

I hope you enjoy these as much as I did. Thanks for reading! More to come. 

Simon R.

About Me

I was formerly an investment professional at several SF and NY-based venture capital firms (short stint in Austin), but now I live on the cross streets of Pre-Seed Avenue and Too Early Blvd. This blog is to document my journey from where I either start a successful enterprise, or fizzle out into anonymity. Note: I write semi-anonymously so that I can be as open and honest as possible. 

Want to drop me a line? Contact me at

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