Effective Outsourcing for Your Podcast and Business

Jan 25, 2023

Effective Outsourcing

Nathan Hirsch is a serial entrepreneur – who sold FreeUp back in 2019 – and who’s currently the CEO of EcomBalance and Outsource School

He stops by the show to talk about effective outsourcing for entrepreneurs, from why it’s key and when to know it’s a good time to start hiring to his interview approach and the three types of outside helpers you may need.

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Nathan Has Been a Very Busy Entrepreneur

  • When Lyndsay interviewed Nathan for her first podcast he was running FreeUp – which he grew and then sold in November of 2019.
  • Then, he has had the monthly bookkeeping service eComm Balance.
  • And these days Nathan is busy with Outsource School.
  • Outsource School, which was born during the pandemic, is a membership platform that gives its members access to the hiring process and various SOPs Nathan has used for all of his businesses.


Hiring as an Entrepreneur is Key (But Can Be Challenging)

  • Some entrepreneurs seem to somehow resist getting support and hiring help even though their growth curve has reached a point that would require it.
  • As Nathan puts it, ‘hiring is that really unsexy part of being an entrepreneur.’ However, it’s key.
  • Nathan learned his lesson when he was running his Amazon business while in college – working nights and weekends. He realized that the business wasn’t going to scale unless he hired help.
  • Hiring as an entrepreneur is hard. That’s where a good hiring process plays a crucial role because bad hires are expensive. 
  • Having a good hiring process that results in good hires that stick around for a high percentage of time is a game-changer.
  • Doing it all yourself is hard. There are very few 7-8 figure entrepreneurs doing it all by themselves.


How to Know When It’s a Good Time to Hire Someone

  • Nathan and his team have developed a calculator that tells you, from a money side, when it’s a good time to hire.
  • There are three different types of hires: followers, doers, and experts. 
  • Followers are your virtual assistants, who follow what you teach them. You bring followers in when you’ve mastered a process but are in need of spending your time on other things.
  • Doers are specialists who are doing the same thing 8-10 hours a week – like a graphic designer, for example. Specialists are for you whenever you have a project that needs to get done.
  • Experts are high-level people who have their own processes and systems, and who you can hire to avoid having to learn something (like Facebook ads, for instance). And they should be someone you look at whenever something comes up and it isn’t something you’re an expert in.
  • Understanding the 3 types of hires will really help you understand when it’s the right time to bring someone on board, and who.

Nathan Hirsch 4

Getting Started With Outsourcing

  • Nathan recommends the following way to get started with outsourcing: create a list of all the different things you do in your business, and order them from easiest to hardest. Start hiring people to help you with the easiest tasks for a few hours a week.
  • One of the biggest lessons Nathan learned with FreeUp was the importance of treating people well and getting them motivated. One can do that by sharing goals and creating a thriving company culture where everyone feels part of the family.
  • One of the hardest things Nathan had to do was informing his internal team that they wouldn’t continue with FreeUp after it was going to be sold.
  • A challenge Nathan has faced as an entrepreneur is finding a good balance between finding clients and finding freelancers.
  • As Nathan points out, it’s important to remember that ‘What works at $1M doesn’t at $5M. And what works at $5M doesn’t work at $10M.’ When you hit those benchmarks, you need to learn how to delegate more.


Tips for a Great Interviewing Process

  • Nathan and his team always focus on three key aspects for each candidate: skills, attitude, and communication.
  • A mistake Nathan has noticed many entrepreneurs make is they only focus on the skills and years of experience of potential hires. 
  • At Outsource School, they teach the so-called Care Interview Process, which focuses on communication, attitude, red flags, and experience.
  • Having an SOP is a great starting point, says Nathan. Have a basic process or even a rough draft that breaks down the goals, why you’re doing something, the steps that need to be taken, and the red flags to be aware of.

“Look at these three areas when interviewing new potential hires –  skills, attitude and communication.”


Working With New Hires

  • Everyone learns in different ways – some prefer written guides, others checklists, while others are fans of Loom videos – so you need to keep that in mind.
  • Nathan prefers documents over videos because they don’t get outdated as quickly and they can easily be edited in a few clicks.
  • For Nathan, how you run meetings is key, and it’s important to walk new hires through how you use communication tools like Slack, how you use emails, and setting realistic expectations, among other things.
  • Putting team leaders in place to manage others as you grow is another big component of successful managing and outsourcing.
  • Nathan’s favorite approach for finding team leaders is to promote from within.


Nathan Hirsch is a lifelong entrepreneur and currently the CEO of EcomBalance and Outsource School. Nathan is best known for co-founding FreeUp.net in 2015 with an initial $5,000 investment, scaling it to $12 million in yearly revenue, and having it acquired in 2019. Today, he leads EcomBalance, an online bookkeeping service for eCommerce and digital businesses, and Outsource School, a membership teaching business owners how to hire effectively online. Nathan has appeared on 400+ podcasts, is a social media personality. Him and his wife live in Denver, Colorado with his two dogs where they are foster parents.


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