It has been almost a year since I left my cushy job at Cisco Systems and embarked on my own “Security Journey” as CEO of my own company. I’m writing this down as much for myself as for anyone who might read it. I’m writing this to remind myself what I’ve learned in the last year, and to chronicle some of the challenges of launching Security Journey.

To quickly catch up on where this story started, read The Day I met John Chambers… and Quit. I wonder if John Chambers ever read that article, or if he’ll read this one?

Here is my list of lessons learned in Year 1 as CEO of Security Journey:

  1. The Sales cycle is long. When people tell you to not expect to have any money coming inbound for 6 months, they are speaking the truth. We were lucky to have a friendly partner bring us in on a project that allowed us to earn a bit of money to sustain life in the early days.
  2. Book knowledge of sales does not equal the ability to sell. The CEO must be the chief salesperson in the beginning, and the lessons I’ve learned about sales have come from the school of hard knocks. Sales is about grinding as much as it’s about skill and finesse. Some days it’s just about reaching out to someone, even though I am sure that they hate me for e-mailing or calling them ONE MORE TIME.
  3. The strength of the sales funnel makes or breaks a product aimed at individuals. A sales funnel is the idea that you take a prospect on a journey between when they learn about your product until they give you some money. The sales funnel connects websites with email and ultimately your product. We’ve experimented with lots of tools, and have landed on Lead Pages and Drip as our tools of choice to engage one-on-one with customers.
  4. Pricing your services involves trial and error. As I look back, I’m embarrassed by one of the first proposals I wrote. I scoped an entire (almost lifetime) engagement between a customer and I. Of course, they balked at the cost. I learned the importance of selling an entry-level engagement and building trust. After they see that we are for real and what we can do, then we can talk long term.
  5. My personal brand developed via the security conference circuit and the Cisco name came up much shorter than I imagined. It didn’t hurt that I had worked to get my name out across the industry and carried the title of Chief Security Advocate at Cisco, but it did not carry me as far as I thought it would.
  6. Learning a programming language (Ruby on Rails) is very rewarding and cost-effective. When you don’t need outside consultants to fix a bug in your web application, you can use those funds to eat. Since becoming semi-proficient, I’ve done all my own feature work for the Security Journey web app.
  7. Grinding needs to be a way of life. If the startup life was easy, everyone on earth would have one, and nobody would work for anyone else. Grinding is the process of rolling up the sleeves and going to work. Sometimes I dive deep into Marketing or Sales or Social, things I didn’t use enter this game knowing much about.
  8. Startups can be a dark place some days. And a bright place on other days. If you do this, there will be days when you think all hope is lost. Once or twice this past year, I’ve looked at my wife and COO (Deb Romeo) and said, “I need to go back to work.” I’d be lying if I told you this didn’t happen. We are lucky that things have worked out, and now we have a stable income stream, and resources to focus on connecting our product to those who need it.

I’m hoping that this information will help someone, but I know it wouldn’t have helped me. I could have read this stuff on multiple sites, but I wouldn’t have taken it to heart because I had to experience it firsthand for it to change me.

If you experience this in the future or have experienced it in the past, drop me a note and let me know how it went for you.