2019 was quite a year for Security Journey, as we added additional team members, and are about to double the size of our sales staff. I’ve recounted a startup adage I’ve heard a few times from different places: with startups, you get the highest highs and the lowest lows. What nobody tells you when you start is that sometimes they happen on the same day.

I’m not complaining, as one of the things that I love about the startup world is the constant problem solving and challenges that arise. I’m a problem solver by nature, and could not imagine doing anything else at this stage of my career.

Here is my list of year four lessons learned.

  1. Venture capital is not required to grow a company. My statement is countercultural in the startup world. I’m not saying we will never take money, or that I’m against venture capital. I’m saying that I’ve realized that for us, it is possible and okay to grow more slowly, regardless of what the industry says. Revenue drives growth, and we have it.
  2. The CEO wears many hats and must look for opportunities to shed some hats as the company matures. I mentioned last year about the swim lane analysis and how powerful that exercise is to capture the depth of all the things that I do as CEO. Shedding some hats is more difficult at our current stage, but we have been able to create a Customer Support function. We’ve also built a stack of our next ten hires, based on where we need the most help. I love to develop content and guide the design of our platform, and one of my goals for 2020 is to spend more time on those two things.
  3. Some times an opportunity is the core, and other times its context. For a bootstrapped business, you either invest your own money or you work on other things to cashflow growth. It’s essential to realize what is core and context for your business. We went through this exercise last year. Our growth has allowed us to focus almost exclusively on the core for 2020, but for a bootstrapped company, cutting the context is more complicated and feels much riskier, but it must happen.
  4. Having a booth at events that target our core customers is a splendid way to generate leads. Justin from our team is an excellent salesperson and has a hidden talent for design. He designed and oversaw the construction of our own custom booth, which stands out amongst all the other booths at the events we’ve been to. We’ve found that targeting specific events results in plenty of conversations and demos at the booth. We use a different strategy for more significant security events, where our audience is just a small percentage of available attendees. We built a collection of laptop stickers that are topical and humorous, and they have been well-received worldwide.
  5. Company culture is a difficult thing to quantify. We’ve documented our core “culture” and values at Security Journey, and it was a more complicated process than I would have thought. It’s nice that we have a few years of experience where culture was caught not taught, as we have documented what is typical for Security Journey. Still, if you had asked me four years ago about the difficulty level of recording and building company culture, I would have said “easy.” The advice here is to not stress about the perfect culture document, as culture is a living and breathing thing.
  6. Giving back to others at different stages of the startup journey feels good. I’ve had the opportunity to meet with other entrepreneurs with companies at various stages, and offer advice to them. I initially thought that I would not have much to offer, but I’ve realized that surviving for four years with a startup and still feeding my kids counts for something!
  7. Product pricing is an art and not a science. Pricing is one of the most often written about startup topics. We’ve had multiple different approaches to pricing over the last year. We went innovative, and it was too hard for some to understand. We went back to a classic approach, but that doesn’t have enough upside for security culture growth companies. We’ve landed on a hybrid that serves all our customers well, and I’m sure we’ll continue to tweak for 2020.
  8. When facing a challenging decision, build a company that I’d like to work for. As we’ve grown in the past year, we’ve worked hard to grow up our benefits packages. As I had to contemplate how much to contribute from the company, I landed on a straightforward question: if I choose a specific amount or value, am I creating a company that I’d be excited to work for? If the answer is no, then I need to re-assess my decision.
  9. Interviewing potential employees is a team effort and everyone’s vote matters. As we’ve interviewed folks this year, I remembered something I learned the hard way previously in my career. When hiring, everyone on the team is involved in the process, and everyone gets a say. In the past, I’ve hired at other companies and vetoed my team’s opinion, and paid the price. At Security Journey, everyone from the direct team participates in the interview process, and everyone gets a say in whether we move forward with a candidate.
  10. Hire for competence and cultural fit, and don’t discount the cultural fit. When a company is small, you worry about hiring a person unable to fulfill the job responsibilities and not so much about the cultural fit. I’ve learned the importance of considering both the cultural fit and the added value a person brings to the table outside their core competencies. When you are small, everyone wears multiple hats. Work should be a place to excel, kick butt, and have fun with those around you.

These are my learnings from last year. Please share this far and wide, and reach out if you think Security Journey could help your organization, or to catch up. Here’s to a full and rewarding year five!

If you want a bit of history you can read where this story began with The Day I met John Chambers… and QuitWhat I Learned in Year One of MY “Security Journey”, and What I Learned in Year Two of MY “Security Journey”, and What I Learned in Year Three of MY “Security Journey”.