About the Episode:

In this episode, we’re chatting with Jake Jorgovan, an entrepreneur and founder at Outbound Creative where he’s a sales and marketing consultant for agencies, helping them land their dream clients.

Over the years, Jake has run his own video production agency, he’s been a freelancer, and he has his own podcast for agencies and consultants called Working Without Pants.

Jake is a pro at coming up with creative strategies for landing freelance clients—and he’s won business for both himself and his clients with Fortune 500 companies & A-list touring artists.

In Today’s Episode, We Talk About:

03:26 We start off by learning how Jake began his entrepreneurial career.
04:50 How his first agency business got it’s first “big” client.
[07:42] His best piece of business advice for starters on figuring out how to price your services.

09:08 What he did after leaving his first agency business.
11:13 He talks about his biggest failure – launching a startup that ultimately failed.
12:57 His best piece of advice on how to identify potential opportunities and disasters.
13:56 How he recovered after an opportunity that crashed and burned.
15:29 His tactical advice for landing your first high-paying freelance clients.
17:13 An out of the box idea to attract the attention of potential freelance clients.
22:46 How he identifies potential clients and other strategies he uses to land more clients for his consultancy.
26:57 How to start your own side hustle consulting business while working your 9-to-5 job.
28:01 Jake introduces us to his most recent side project, Agency Scout and talks about how it works.
33:39 What sacrifices he’s had to make in order to create the time needed to run his business.
35:46 How to find time for your side hustle while balancing a busy schedule.
36:53 His biggest piece of advice on how to hit your first “big win”.
38:37 How to figure out your next move when your business isn’t getting the results you want.

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Resources Mentioned:



Commerce Hero

Connect with My Guest:


Jake Jorgovan on TwitterFacebook and LinkedIn


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In today's episode, we're talking about how to land six-figure freelance clients (on the side) with experienced freelancer and consultant, Jake Jorgovan. We cover the most creative outreach campaigns he's seen and launched, including mailing cakes & hot sauce to prospective clients, we're diving into what makes the perfect freelance pitch, and much more...

For those of you that love Pinterest, here's an image I put together that plays nicely over there 😊

In this episode, we're talking about how to land six-figure freelance clients (on the side) with experienced freelancer and consultant, Jake Jorgovan.

Ryan Robinson
Ryan Robinson

Full-time blogger, podcaster and side project aficionado. Join me here, on ryrob.com to learn how to start a blog, make money blogging and grow a profitable side business. I also write for publications like Fast Company, Forbes, Entrepreneur, Inc, Business Insider and more. Let’s chat on Twitter about business and side projects.

    4 replies to "#13: Landing Six-Figure Freelance Clients (on the Side) and Perfecting Your Pitch with Jake Jorgovan"

    • Tanya Williams

      Loved this interview with Jake 👏

      The biggest takeaway for me was the power of just asking for referrals from your best client(s). So simple, but something I feel like most freelancers never do.

      • Ryan Robinson

        Right?! Huge takeaway for me too.. that’s not something I do enough of either. Always learning!

    • Max Chiossi

      What Jake says about when to know to move on and when to change your aim is quite strong. Not many talk about this out there, but I believe it’s something we should all be aware of.
      Thanks for this episode, Ryan!

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