Lessons after Year 2 in a Start-up

In 2015, I left my secure, highly paid, senior position as Head of Marketing Technology at Aetna to build my own company. I wrote a post about it at that time. As I pass Year 2 in this start-up world, I thought I would write down some of what I have experienced.

  1. What you thought you would do, is not the same as where you will end up after Year 1 or Year 2. If you are building a SaaS product like we did, your product road map will morph from where you thought you were headed. If you are adding new services, also something we did later on, you will require a different skill-set on the team that you didn’t think you would need when you started on your journey. Being able to quickly adapt and adjust is key to making this work.
  2. Don’t assume that you will be able to leverage your relationships from your past. I made quite a few assumptions about this when I started and it didn’t work out like I thought it would. That is absolutely normal. Again, most of this is not done out of malice. People are busy, have their own work issues (you remember those right?) and don’t have time to spend with you. However, when you do find those people, be grateful because they will help you and you find out that you are helping them as well.
  3. You need to define a direction early on of where you want your company to go. Do you want to build something that replaces your salary and allows you to be your own boss, or do you want to quickly expand the company and make scale and growth your focus? Don’t listen to the hype of what we hear non-stop from the VC news in the media. Not everyone needs to get VC funding and not everyone needs to build a company that grows 200% YoY. Neither decision is wrong. Always remember that you get to make the choice. Don’t let others bully you into changing how you want your company to operate.
  4. Sign up to be a mentor for students at your alma mater. I do this at Depaul University and helping these kids think through some of what they want to do is incredibly gratifying. You might not think of yourself as the mentoring type but we all need help and the kids trying to get their degrees are hungry for information.
  5. Doing the start-up thing solo can be harder initially but there is value in being able to drive the direction in the way you see fit. You can always add people as time goes on if you are successful without the extra overhead. In some ways I wish I had started with a partner, but looking back from Year 2, I am glad I went the way I did.
  6. Don’t worry about being self-promoting. As I used to tell my teams in corporate, no one is going to sell yourself better or more accurately than yourself. In start-ups it is 10 times that. There is a fine line between being irritating and selling yourself but you will find the right balance after a while. Don’t let anyone quiet you down. If they don’t like to hear it, be rid of them. Life is too short.
  7. Read and ingest what others have done but don’t try to mirror them. Your personality, strategy, character, product idea and philosophy are different. Use the lessons they learned as a compass but you don’t need to follow their path. Most of us take different paths. There are many lessons to be learned on every path.

Reach out if you want to chat about your experiences or if you are thinking about starting your own company and want feedback/advice. You can reach me at joseph at 249labs.com.

249Labs is a marketing technology start-up based in Tampa. Our large enterprise SaaS platform for marketers, Open Lantern, is used by many large brands globally and can be found at openlantern.com. Our consulting practice focuses on the regulated verticals of healthcare and financial services. Our senior team brings over 50 years of executive, large corporate, digital experience to the table.