Jake Jorgovan always wanted to inspire others, but unlike most entrepreneurs he isn't doing so by selling a product; he's sharing a service. Established in 2013, Jorgovan's "Working Without Pants" weekly podcast showcases entrepreneurs who are making a difference, and they share how you can, too.

By Courtney Fishman
February 18, 2016

What interested you about starting a podcast? Why this medium?

I first started as a podcast listener and saw the impact that these shows can have on an individual's life. After months and months of listening, I decided to give it a shot and start my own. What I love about the medium is you get to have conversations with other people and share them with the world. You know those conversations that you have with your smartest friends or mentors where you learn invaluable things? Well with podcasting you have a platform to share those conversations.

How did you decide to feature agency owners and entrepreneurs? 

The show evolved over the course of the past two years along with the audience. My decision to focus on the audience was based partially on my own experiences running an agency, as well as the kind of people who I was interested in talking to. By focusing on that niche of audience, it enables me to go a lot deeper and create meaningful conversations that provide real value for my audience. 

What was your entrepreneur moment -- when you knew you wanted to be an entrepreneur?

Growing up I always had a dislike in working for others. I got annoyed at bosses and the political issues that were in all of the workplaces I was in. I knew I wanted something different, and my entrepreneurial surge kind of happened by accident when I got an opportunity to do my first paid project. At the time I was doing audio and it was a simple assignment of $175 to record a local band's concert, but I will never forget that day because as soon as I got home from that project I immediately started thinking "What if I recorded a band five nights a week?" That was the start of a long and twisted journey through many different businesses that led me to where I am today.

What do you know now that you wish you knew when you first started?

Start with a service business, not a product business. This is the No. 1 mistake I see new entrepreneurs make when they start out. Products are hard and many entrepreneurs who have been at it for years still struggle to get products off the ground. When you start a service business, you are basically just taking your skills and charging for them. This is similar to having a job, except you are working for yourself instead of a full-time employer. Keep it simple: Start with a service.

Complete this sentence: I can't work without …

My focus sheet. This productivity system sits next to my desk at all times and is how I manage my daily, weekly, monthly, and quarterly goals. I have been using it for almost three years now and without it I would be useless.

What was your biggest surprise when you started your podcast (good or bad)?

When I started a podcast, I thought it would be great for the content and the audience I gathered, but to be honest the biggest benefit has come from the people I have met. Many of my good friends started as guests on my podcasts. Many of my customers and clients I met through my podcast. The podcast has become an invaluable source of networking and meeting new people.

What's been your favorite podcast to produce? 

Well they are all pretty fun, although one of my favorites has been with Allie Lehman of Death to the Stock Photo. We chatted about authenticity and staying true to yourself in your creative career. 

How do you choose people to feature?

I look for people who I find interesting and want to know more about. If someone has a great business, I want to learn how they built it up and what was successful. If I am interested in my guests, then I know my audience will be, as well.

Do you have a mentor? If so, who? 

Yes, I have quite a few. One is Jeff Cornwall of The Entrepreneurial Mind. He was my college professor and has been invaluable in helping me find my way through my entrepreneurial career. Marcus Blankenship is another great mentor of mine who has helped me learn how to build an actual company that runs smoothly.

Do you have one single tip for success? Focus and determination. There is a great idea from Napoleon Hill where he says that one of the differentiating factors between those that succeed and those that don't are that successful people choose a goal and then pursue that goal with focused determination. It's not easy building a business, but it's even harder when you keep jumping from idea to idea. 

Is your podcast a full-time job? If not, what is your day job?

The podcast is a tool for brand building and networking, which indirectly feeds into my primary business. My main business is Outbound Creative, which is where I help agencies win their dream clients through creating eye-catching outreach campaigns.

Do you think podcasts can become a profitable business? Was this ever the intention?

Too many people think the route to a profitable podcast is sponsorship. The truth is, it is very hard to get an audience big enough to be worth big sponsorship dollars. Instead, look at podcasting as a means of marketing, thought leadership, and lead generation for your business. My audience for my podcast is agency owners and creative entrepreneurs. My business serves that exact audience. By connecting my podcast in an authentic way to my business, the podcast becomes a source of growth for Outbound Creative.


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