How to scale your business by coaching your teams with jake jorgovan

Subscribe To The Podcast

On today’s episode, I am talking with Jake Jorgovan. He is one of the elite few that have returned to the show for a second time because they have something that I just think is so interesting that I just had to bring him back again so we can dig a little bit deeper. We are talking about coaching skills as a way to uplift and enhance your team.    


Jake is a creator and entrepreneur, and he enjoys building things. He has two companies, Lead Cookie and Content Allies. Lead Cookie is a done for you human-powered outreach company. They run LinkedIn email and phone outreach campaigns to set appointments for their customers with their target prospects. Content Allies is a content marketing agency focused on thought leadership content. He runs his businesses and works on many other projects all while traveling the world.

Jake shares some incredible insights that have helped me, my business, and how I personally lead. I know that it will help many other leaders out there as well. 

We discuss:

  • [01:47] Jake shares about his turning point about three years ago when he decided to build his business and team again.
  • [02:53] To lead others and be a coach you have to lead yourself first and be a quality person and individual that people want to work for and follow.
  • [03:44] Jake has two companies, Lead Cookie and Content Allies.
  • [06:07] He coached one of his employees, Jeff, how to lead, manage virtual assistants, advise, hire, and fire.
  • [08:12] When he first started out, Jake held weekly 1-1 meetings for 30 minutes where he could invest in people, see where they were struggling, give feedback and look and see what their blind spots were.
  • [09:24] Jake teaches his team members and gives them frameworks on how to think.
  • [12:09] As an employer it would be risky and not wise to go too deep into personal coaching. You have to draw that line and not get too far into the personal side.
  • [13:24] They offer $50 per quarter education reimbursements for their team. It is not a whole lot of money, but it provides them with educational resources.
  • [14:59] It is important to learn your team’s strengths so they understand their strengths, but also you understand how you can best work with them.
  • [18:13] As a leader you need to focus on good character. Jake does this through mediation, being mindful, conscious, and transparent.
  • [18:28] Your business is a reflection of yourself. If you are steady, show up, do what you say you will do, you’re honest and open, people learn to trust you.
  • [19:42] To be able to go to your team and speak on hard topics, letting someone go, or cutting hours are difficult things as a leader.
  • [20:41] Transparency is really key and helps a ton to create a team that trusts you.
  • [22:46] Jake’s team has access to overall revenue numbers and profit margins they are targeting.
  • [24:01] They use the Entrepreneur Operating System (EOS) Traction Framework for their vision planning.
  • [24:55] They hardly have any turnover because they create a super fun culture and let people know that their goal is to give them freedom and a good work-life balance.
  • [27:50] The biggest thing is that you have to work on yourself first. Then start by having 1-1 meetings on a weekly basis with the people you are directly managing or you can level up.
  • [29:41] In full transparency Kyle shares about the earthquake and aftershocks happening in his area.

Connect with Jake

Connect with Kyle + The Story Engine

Scroll to Top