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Today, we are joined by Steve Krakower, who knew from a young age that he always wanted to be an entrepreneur. After failing at a few startups ideas, Steve realized he needed to get a full-time job when graduating from Loyola University. He was able to secure a job at a local Baltimore startup called Hunter A Killer.

As one of the early employees, Steve was able to take on a hands on role to help the company grow. He learned about the different phases of a company lifecycle and how to scale a startup. He had always been open with the CEO that he would leave to start his own business. After a year and a half, Steve officially quit to start Harbor Marketing Agency.

The first year was extremely difficult for Steve. He fell tens of thousands of dollars into debt, started suffering from high blood pressure, and was struggling to grow the business. However, he had no plan b and decided he would do whatever it took to make the business work. He joined a mastermind group with other successful digital agency owners, which was a turning point for him. People who had already been successful taught him how to sell, how to hire, how to create processes, etc.

The most important change that Steve made was that he decided to focus on offering digital marketing services for only subscription box companies. This allowed him and his team to become experts in that specific niche. Even thought they narrowed their services and type of client, they drove better results and continually saw sales increase year over year.

Fast forward to today, Steve has scaled Harbor Marketing agency over the past 5 years and is focused on continuing to grow the team moving forward. If anyone has a subscription box company or knows anyone who dies, Steve is your guy. Please reach out to him here!

Check out the conversation as we dive into the following:

  • How he always knew he wanted to be an entrepreneur
  • How joining a mastermind group helped him learn from other successful entrepreneurs
  • How aligning core values is the most important piece to building company culture
  • Why he stopped chasing work life balance
  • How to focus on adopting habits that help unplugging from work

Listen to Steve share his story and get inspired with his amazing advice to people thinking about following a similar path. Check out the full conversation on YouTube or Spotify by clicking the links below.

Listen on Spotify

Listen on Apple Podcasts

Know someone who should be on Why I Quit? We’re looking for all types of stories and people to feature at the top of the show. To nominate yourself or someone else, email and tell us your name, where you’re from and what you want to talk about.