This Founder Struck Marketing Gold When He Built a White-Glove Podcasting Service That Now Generates $100,000+ MRR

According to a July report from Insider Intelligence, 60 percent of US adults aged 18 to 34 will listen to podcasts monthly in 2021. But you probably didn’t need the stats to know podcasts are everywhere and people love them. 

Surprisingly, though every company seems to have its own podcast these days, few besides Spotify have dared to try creating them at scale. Today, however, there is a new contender in the podcast space that may just dominate the market in the next few years.

Jake Jorgovan created Content Allies to tap into the new wave of content marketing triggered in the late 2010s. After writing thought leadership pieces and realizing they couldn’t scale, he pivoted to podcasts and now has a business with over $100,000 in monthly recurring revenue.

When it comes to expert marketers, Jake’s the real deal. He’s spoken at prestigious events like SXSW and was awarded Nashville, Tennessee’s Youth Entrepreneur of the Year award. He’s also founded and run six different businesses. A large number of them simultaneously and one or two of them still run to this day. Besides that, he is a visual artist and music producer to boot.

Here’s how trial and error helped this serial entrepreneur become one of the foremost marketers in his field.

Is Marketing Punk Rock?

Jake believes he was born to be in marketing and his career is proof of that.

“I enjoyed the psychology of marketing from a young age,” he says. “I always enjoyed punk rock and fighting against ‘the system’, and I think that young attitude made me look at marketing as ‘how it all is.’ I didn’t want to be the one that was being marketed to, but instead the one that was putting that out there.”

Even while studying entrepreneurship and audio engineering at Belmont University, Jake had created his first agency with some friends called Rabbit Hole Creative. They specialized in video production and live event video design (the things you see playing behind musicians in concerts). You might say they were doing well: they were working with artists like Paramore, CeeLo Green, and Dolly Parton.

Content Allies started as a LinkedIn thought leadership service and pivoted to podcasts.

But Jake wasn’t content to be the average CEO-slash-founder. He had read the highly influential The 4-Hour Workweek and became obsessed with finding a role where he didn’t need to come into an office and grind for hours every day. Working from various locations abroad, he moved Rabbit Hole Creative to the backseat in 2014 and created a couple of failed agencies over the course of the next year.

Finally, in 2017, Jake found success with his new marketing agency, Lead Cookie. Lead Cookie specialized in business lead generation, specifically on LinkedIn. They created systems helping businesses reach out to prospective clients and partners more easily. After seeing decent growth in the following years, Jake became increasingly concerned about growing it further.

“I’d been running Lead Cookie for four-and-a-half to five years and I didn’t need to spend a lot of time on it,” he says. “I thought, ‘Why don’t I build a new company that is a better long-term viable business?’ I wanted a scalable low-churn service in the content marketing space so I pivoted to a virtual assistant for content marketers.”

Jake pulled a couple of team members including Belmont University buddy, Jeff Markle, over from Lead Cookie to a new company called Content Allies. 

Finding Podcasts Through Trial and Error

To begin landing clients for Content Allies, Jake used a LinkedIn content service to create email lists of his contacts from his decade in the field. Then, using his team’s extensive knowledge of marketing, Content Allies soon was airborne and revenue positive.

“We were able to give our clients pretty good results and that gave us cash flow we needed to iterate,” says Jake.

Initially, Content Allies was a virtual assistant service for content teams, but it quickly pivoted into what Jake thought was the next big content growth area: thought leadership articles on LinkedIn. These are pieces ghost-written for business founders to drive conversations and promote brand authority. Content Allies picked up its first ten clients quickly and started seeing great results, however, Jake realized he was still spending way more time than he wanted.

“The problem with thought leadership articles was clients felt such a drive to make it ‘perfect,’” says Jake. “We would need to do a slog of revisions every time. The amount of work required and timelines just didn’t add up to a scalable business model.”

Wary about making a hard pivot immediately, Jake backed Content Allies into a more general content service while he looked for a new avenue. In 2020 he then stumbled on what ended up being a million-dollar pivot: podcasts.

A Boutique Media Agency Is Born

Jake decided podcasting was the right course because it was the form of content that made both his clients and staff happy.

“Eventually we looked around and asked, ‘Who are our happiest clients?’ and ‘Who do we enjoy working with the most?’ It was clear that podcasting was where our clients were getting the best results and where we were having a lot of fun,” says Jake. “I had already been podcasting for seven or eight years myself at that point and was quite familiar with that whole process.”

The podcasts were a hit, and with the help of a pandemic driving customers to online media in 2020 and 2021, the business began growing as fast as it could book new shows.

“I think we’ve been so successful because we struck a nerve. We’re riding a huge wave of podcasting,” says Jake. “Partly due to COVID, events were no longer a thing and digital marketing has exploded as a whole. Podcasts lie right in the middle of that change.”

What Content Allies provides that its competitors don’t is a service covering every aspect of podcasting. While other podcasting services begin and end with production and maybe some audio editing, Content Allies takes care of everything else too – from scheduling guests to marketing to social media content.

A small section from the Content Allies website listing some of their podcasts

“There are a lot of basic podcast services out there and lots of piece-together podcast services,” says Jake. “For a larger entity to do a podcast there are a lot of aspects they’d rather just pay for than learn themselves. We entered the market as a full-service white glove agency that does everything. You just show up, say your piece, and we do the rest.”

Besides being great standalone content, podcasts provide a glut of media that can be repurposed for other marketing.

“We don’t just edit podcasts,” says Jake. “We turn those into video clips, audiograms, quilt blocks for social media, and blog posts.”

Their successful product is only one-half of Content Allies profitability equation. They keep costs down by running a very small core team and hiring contractors as needed.

“All of our audio editors, writers, and video editors are on a contract basis. Our project managers and designers are in-house,” says Jake.

One of the biggest contractors for Content Allies is a whitelabel agency they use for closing and optimizing sales called Add1Zero. Jake believes they really did add a zero to his businesses’ revenue and wants to get the word out about their service to more founders.

The Content Allies team today is totally remote and spans the US, Canada, Spain, the Philippines, and Zambia with most clients from the US and Europe. On the back of COVID, they’ve grown more than 600 percent since December of 2020. Their most successful shows include an internal podcast called Leaders of B2B as well as popular client podcasts for Siemens Energy and even Facebook.

The Content Allies Process

“For most of our small-to-mid-sized businesses we have a very streamlined process,” says Jake. “Most of our clients say once they get started with our service they only need one to two hours a week for interviews plus a little more for prep.” 

First, the Content Allies team gives their client a questionnaire to define business goals. Then they do a kickoff call to better align with the business’ strategy and finalize final details like the show name. Once they’ve set up a show idea and name, Content Allies begins performing guest outreach. After the podcast episode is finished, Content Allies takes the recording, turns it into content, and completes backend steps like editing audio and video files.

“Big companies tend to use a podcasting series as a way of relationship-building and networking,” says Jake. “We usually do podcasts that both feature and ego-boost their customers. Right now we do one podcast with the CEO of a company called Talent Acquisition Leaders. His show allows him to interview his ideal clients and this creates a media property that is completely relevant to the customers he’s targeting.”

With the traction he’s seen recently, Jake is very optimistic about the future of Content Allies.

“I think we’ll continue to grow at a fast pace,” he says. “Now we’re probably in the top three podcast production teams in the business. I’m actively trying to reduce work hours so I want to hire an external CEO. My goal is to build a 20-year business that just keeps going and provides a great quality of life and freedom for myself, my team members, and our customers,”

Tips For Founders From a Successful Serial Entrepreneur

When it comes to his thoughts on bootstrapping Jake says this:

“I never sought out venture capital — I always wanted to bootstrap. At one point at an earlier company I took on an investor and didn’t like it,” he says. “It created a dynamic where I felt I had to please this guy and it was uncomfortable. I think bootstrapping forces you to figure things out and improve.”

Jake Jorgovan is a veteran podcaster and runs his own podcast on the side.

Though it may not be as big a hit with the VCs, he strongly believes his service model for starting businesses is a superior model for finding product-market fit.

“For anyone starting at any level of a services business: don’t start incurring costs until you do the work. Just find a website and create an offer and then don’t fulfill it until you can do it yourself. Put it out there and make it happen. Also, software makes it hard to pivot whereas with services you can change fast,” he says.

Jake’s an inspiring guy and he knows it, that’s why he runs a personal podcast on his website called Working Without Pants. On his podcast, he discusses his quest for creating profitable and time-effective businesses and interviews founders who do the same.

Success stories like this are a reminder that great ideas are often right under our noses, we just need to try them out. Jake’s strength is that he’s the type of person who tries without fear of failure. Today his successes eclipse his occasional flops. Each attempt was a building block for what he has accomplished today.

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Andrew Gazdecki
Andrew Gazdecki
Andrew is an award-winning serial entrepreneur with three exits. He’s the founder and CEO of MicroAcquire, the world’s most founder-friendly startup marketplace, and its rebellious child, Bootstrappers, which gives voice to the entrepreneurial underdog. When not building businesses, he writes for Forbes, Entrepreneur, and now, Bootstrappers.

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