Ep1: VC by Day, Entrepreneur by Night & Weekend - Learning Hard Things The Hard Way

I’m a venture capital investor attempting to moonlight on nights and weekends as an entrepreneur. It has been a challenging, humbling, rollercoaster experience and I wanted to share the experience with others. If for no other reason then so all of the entrepreneurs I work with can have a good laugh at my expense. You’re welcome.

So here it goes: Five painful learning experiences of this past week.

Lesson #1: You cannot predict how website visitors will navigate your website.

• I designed and built my website thinking it would be really simple. People would land on the front page, read the blurb about what I was doing and then click on the big call to action button. After a couple days, I looked at the analytics and found that people did just about everything else other than click on the call to action button. They went to the gallery to look at pictures, they went to the about page to read about the project, they clicked to the social media accounts but mostly they bounced. I was completely mystified because I was emailing my close friends and sending them to the website with the specific goal of clicking through on a specific call to action. I then watched a few people go through the website flow on their phones and I was amazed that they couldn’t figure out what I was asking them to do. Turns out there were a lot of things obfuscating the call to action (it was below the fold, the button blended in with the background, etc.). So I completely overhauled the website and eliminated every single link on the front page except the call to action (which I made appear in 4 different places). Conversion rate increased significantly (it’s amazing that people will click different links to take the same action) and bounce rate declined. I revised the site again to include some of the other information, but kept the front page very focused on one call to action. If you feel like helping me with constructive comments, the website is www.siliconheroes.com).

Lesson #2: Social marketing is unnecessarily hard. I now have a lot more respect for social media marketers after this past week.

• My project involves crowdfunding a graphic novel. As a result, I’ve got a lot of awesome images that I can share on social media to hopefully increase awareness of the project. Great, I should just be able to select images and then send them out via Buffer, right? Wrong. Every social media platform requires a different size image for EVERYTHING – profile pictures, headers and posts. Why hasn’t someone solved this?
• Instagram doesn’t allow posting via API…so you have to post from your mobile phone (instead of Buffer or Hootsuite). I suppose this makes the Instagram user experience better, but marketers must hate this…
• Driving true engagement via social is seemingly impossible if you aren’t a good looking person taking selfies or have puppies/kittens/food in your picture. Sure, people will like your posts, but they won’t take the action you want them to take (clicking links, sharing or following). My initial Facebook post announcing my project received over 120 likes in the first 12 hours but only one person actually completed the call to action (thanks Jung!). If anyone has advice on how to use social media to drive a crowdfunding project, I’d love to chat.

Lesson #3: PR is even harder.

• This was probably the most humbling. I assumed (incorrectly) that a graphic novel that positions entrepreneurs as role models for kids and promotes diversity in tech would definitely attract attention from bloggers and journalists. I just needed to find the right ones, introduce my project and their coverage would launch my crowdfunding project to success. So, I did exactly what a few PR experts told me to do – I used Google image search to find out which journalists and bloggers had written about successful crowdfunding projects. I then reached out to them with a short, personalized email that introduced my project and asked if they would cover the launch. Twenty emails and one week later and I’m still waiting for the first reply.
• I sat down with a friend of mine that owns a big web publication. He actually pulled out his phone and showed me the “tips@” email inbox for his website. It was full of Kickstarter projects and requests for PR coverage. I realized at that moment that there is no way I can rely on any press coverage. Now I’m staring at a pretty daunting marketing challenge.

Lesson #4: Don’t rely on a single platform.

• I give entrepreneurs this advice all the time. Don’t rely on a single platform because then you are beholden to them. So why did I not see this coming? My crowdfunding project has a charity angle – I plan on crowdfunding my graphic novel and then donating all of the profits (beyond the costs of producing the book) to Girls Who Code and Code.org. Imagine my shock and dismay when I tried to submit the project to Kickstarter and found out that Kickstarter does not accept projects where any of the funds are donated to charity. Whiskey Tango Foxtrot. I had already shot my video (where I mention the words Kickstarter). All of my creative assets say Kickstarter. My silly ThunderClap says Kickstarter (and I had over 100 people already signed up to Tweet out a message that says Kickstarter). I had already told all of my friends and supporters that I was doing a Kickstarter…and just like that…I wasn’t. Of course, none of this is Kickstarter’s fault. They are pretty clear on their website, I just made incorrect assumptions that my project was going to be okay (though seriously, if you are delivering a great product to the community, why should Kickstarter care what you do with the profits?). As a result of my reliance on a single platform, I spent most of Sunday changing my website, marketing materials and video to now show an Indiegogo campaign. Huge waste of time, lots of lessons learned.

Lesson #5: Every setback is an opportunity.

• All of the above 4 lessons learned involve setbacks. Each setback comes with an accompanying emotional hit. The emotional hits are probably worse than the actual setbacks. The big lesson I tried to take away from this past week (and the Kickstarter fail in particular) is that every setback is an opportunity. Struggling with the website forced me to get much smarter about analytics and link tracking. That is going to prove very useful with marketing. Struggling with social media marketing forced me to spend a lot of time sending emails. My response rate with emails has been fantastic – 80%+ on personalized emails and 30%+ on generic emails. I think the response has been so strong because most of my friends are entrepreneurs or techies and they know how hard it is to launch something. Lastly, struggling with PR is forcing me to think about ways to get dirty with some growth marketing strategies.

​So there you have it folks. Hope you all enjoyed the struggles of a VC trying to moonlight as an entrepreneur. Trust me, I’m better at my day job. The Indiegogo launch date for Silicon Heroes is 16 days away so I’m sure this week is going to have even more setbacks, struggles and challenges. Thank goodness I have a supportive wife and really good friends.