How She Did It: Turning A Podcast Into A Full-Time Career

Jenna Kutcher 

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October 22, 2018


Wanna start a podcast? This might be the sign you’ve been waiting for. Our girl, Nicaila Matthews Okome, is the creator and host of Side Hustle Pro Podcast, the first and only podcast to spotlight bold, black women entrepreneurs who have scaled from side hustle to profitable business.

Nicaila is sharing what exactly it takes to be a podcaster, what the financial situation of podcasting looks like, how to land your dream guests, what the early days looked like and how to turn this “hustle” into a full-time job! It’s safe to say, this woman is AN EXPERT on podcasting and how to make a show sustainable, popular, and profitable.

It’s so much more than just sitting in front of a microphone! Yeah, we’re spilling the beans.

Meet Nicaila

Nicaila Matthews Okome is the creator and founder of Side Hustle Pro Podcast. Nicaila was born in Jamaica and grew up in the Bronx. She always knew she wanted to work in the communications field because she loved storytelling. She pursued a career in PR immediately after earning her undergrad degree but after experiencing the field first-hand she realized it really wasn’t for her. Nicaila pivoted into blogging and social media, which lead to a job at a fashion e-commerce startup handling social media. They were making it up as they went along, and Nicaila wanted a broader lens into the world of social and marketing. She accepted a job at Georgetown, still working in social media and getting her feet wet in marketing, but quickly realized that the quant classes she avoided in college were sneaking up on her. Nicaila decided to go back to school and figure out if marketing was something she wanted to continue. But even after an internship at Google and earning her MBA, she graduated without any job prospects.

“For creative souls who have multi-passions and can’t quite put their finger on where their talents best fit, it’s sometimes hard to fit into these boxes that you find when you go to structured places like business school to get your MBA,” she explained.

Nicaila returned to her roots of social media marketing and blogging, and in her words, “the rest is kind of history!”

Side Hustle Pro: The Beginnings

Nicaila’s podcast evolved organically from blogging. She wrote about things that interested her like marketing and strategy. She wanted to impress potential employers with her thought process and frameworks around marketing. She started conducting interviews for her blog because she loved hearing stories about people who worked amazing jobs but were still building out companies on the side. The result was long blog posts that were getting some traffic and likes on social media, but no one was actually reading the content. On top of that, Nicaila had to cut down the interviews on her blog because they became so lengthy. This was around the same time when she was introduced to the Serial podcast. She listened to the show while she was cooking and one night decided she wanted to try her hand at podcasting.

Start with a Clear Vision

When Nicaila started her podcast she knew the theme would center on side hustlers because that’s where she focused her blog content. She also saw an opportunity to bring more attention to diversity and inclusion in the entrepreneurial world, while highlighting that you don’t need to quit your job, move to Silicon Valley, and do whatever it takes to get funding to make your business work. Nicaila launched Side Hustle Pro with the goal of showcasing bold, black women entrepreneurs who were running businesses on the side while working full time jobs.

“It made it much simpler for me to get started because a lot of times we want to talk about so many different things, but when we really hone in on what [the topic] is going to be, you can map out ‘What does a year of content look like?’ and ‘What will my guests be like? What will they talk about? What kinds of questions will I ask?’”

What is YOUR vision for your podcast? Can you narrow it down to an overriding theme that will lend itself to a year or more of content? Get brainstorming!

Smart Investments to Launch Your Podcast

Over the course of a year and a half, Nicaila spent a few thousand dollars investing in her podcast.

Equipment was a fairly minimal investment — A microphone and a laptop that she already owned, a few pieces of software. The greatest investment Nicaila made was in personal and professional development. She attended conferences and networking events, learning as much as she could about entrepreneurship, building a business, and a growing an online brand.

Nicaila is big on learning how other people have done things before her. She says, “We really don’t have to reinvent the wheel. We really just need to sit down and study and reverse engineer.”

Get Past the “First Show” Nerves

I remember when I started The Goal Digger Podcast I did everything for the show except actually record! I was terrified of hitting record and thinking about that first show.

Nicaila had a similar experience before recording her first show. “I almost didn’t do it. I thought it was stupid. I told my husband I wasn’t doing it and he still teases me to this day.”

That cold feet feeling is part of the realization that you’re putting yourself out there, especially when you’re doing a solo show. Nicaila’s first show was all about when she didn’t get the job at Google after interning there, and it was more transparent than she had ever been. In this episode, Nicaila talks about her experience with Imposter Syndrome working at NPR, sitting around the corner from Guy Raz (How I Built This), and asking herself “Who am I to start a podcast?”

Once Nicaila finally published, the feedback on her podcast was overwhelming. Her audience connected with her story and that’s what they wanted to talk about, and that’s what motivated her to keep going. Shedding the fear of publishing and getting over those first show nerves requires a little bit of faith in the future and envisioning the outcome you aim to achieve. Picture your podcast going live, pushing it out to the world, and the positive response you will receive from your audience. Ready, set, record!

Side Hustle to Full Time Job

After about 6 months of working on her podcast, growing her platforms, focusing on the content, and getting to know her audience as much as possible, Nicaila started to pitch sponsors.

“I knew I had great content and one of my guests told me that if you do something well, you shouldn’t do it for free.” She cold-pitched her first sponsor and that’s how she began to monetize her podcast. From there, she created and sold information products like online courses and guides to add another revenue stream.

Nicaila sticks to paid sponsorships as her core revenue stream, but she’s also added some programs that allowed her to convert her podcast from side hustle to a full time job. Nicaila’s courses are geared toward emerging podcasters and audio engineers who want to scale their podcast to become a career.

Are You Ready for Sponsors?

Monetizing your podcast is exciting — Who doesn’t love turning their hard work into cash flow? But sponsors don’t just start rolling in from day one, at least, that’s not the typical story. The best time to start adding sponsors is after you’ve launched and you know more about your audience.

Sponsors care about numbers, yes, but Nicaila doesn’t believe in the arbitrary threshold of followers or downloads to start pitching sponsors. It’s important to be aware with the CPM equation and how sponsors look at those numbers, but also know that niching down and partnering with sponsors who want to reach your niche audience can also lead to success.

Look at your social insights, do a survey, read your reviews, and when you feel like you have enough information about your audience, that’s when you’re ready to add sponsors to your show.

Nicaila is now at a point in her podcasting journey were most companies approach her about sponsorship opportunities because she continues to show up and create quality work. Occasionally Nicaila will pitch a brand she really wants to work with and that aligns perfectly with her audience or the episode content. When she’s approached by a brand that doesn’t align with her audience, she is honest about the poor fit so she can continue to tailor the best possible content for her dedicated audience.

For The Goal Digger Podcast, we work with an ad agency to pitch our show to brands and they take a cut of the earnings as commission. This extra investment was important for Goal Digger because the podcast manager role already had so much to handle, that the ad portion was best handled by an outside agency who could specialize in monetizing the show.

At first, adding sponsors to Goal Digger worried me. Would people roll their eyes? Would they stop tuning in? But at the very core of what I teach is you should never work free. If your sponsors are carefully chosen to align with your audience and the content, and you truly believe in the product or service you’re advertising, the addition of advertisements can be very organic for the listener.

How to Select Your Guests

Nicaila’s process for selecting interview guests is extremely effective and dialed-in for finding the best content for her audience. Where does she start her research? How does she use a “casting call” format to get the best guests? How does the audience profile of her perfect listener come into play? For the full scoop, you’ve got to tune in to the episode.

What Makes a Good Host?

It’s easy to listen to your favorite podcast hosts and feel intimidated by their greatness, but be kind to yourself. Your favorite hosts sound great because they have more experience, they’re further along in their podcasting journey, and maybe they even have a team of audio engineers and producers to ensure the show sounds it’s best. Everyone has to start somewhere and you will grow into the hosting role if it’s something you truly want to pursue and improve.

What do you like about your favorite hosts? For Nicaila, her favorite hosts are 100-percent themselves on the air. They don’t sound completely poised and perfect like they’re reading the nightly news. They are funny and they feel like a “friend in your head”. For Nicaila, that’s the exact type of feel she wanted her Side Hustle Pro listeners to have, so that’s the approach she took as she started hosting her own podcast.

It was important for me, too, to host The Goal Digger Podcast with an authentic voice and let you get to know the real Jenna Kutcher. People connect with people, and I knew this was the best approach to take when I launched Gold Digger, recording episodes in my car so the dogs wouldn’t bark and ruin a take!

Podcasting is A Lot of Work

Unless you’re joining the podcasting world with a skillset of an audio engineer, journalist, and social media pro all packed into one, podcasting is a learning curve for most beginners. Nicaila shared her early stories of doing her own audio editing and the long nights editing out “ums” from the interview tracks.

“It’s not brain surgery, anyone can do it for sure, it’s just a matter of someone showing you how to do it and then you getting comfortable with whichever editing software you prefer.”

Nicaila has since outsourced the editing task, which is an added expense for the podcast, especially if you’re just starting out. It’s hard to pay into a project that isn’t yet making money, but these kinds of investments in your podcast can free up your time to grow the podcast in other areas like social media marketing, content creation, and more.

Establishing a workflow early on can help you stay organized and effective when planning, scheduling, recording, producing, and finally releasing and promoting your show. In the full episode, Nicaila shares her workflow, including how she uses a platform called Airtable, to organize and track the entire podcasting process from start to finish. Start listening now.

If She Could Start Over, What Would She Change?

Nicaila wishes she had included more opportunities to share her own stories. Nicaila loves to interview people, but her solo show episodes are always a hit with the Side Hustle Pro audience. At the beginning, she didn’t include as many stories from her own life and journey. Now that Nicaila knows her audience loves a peek into her life, she’s building in more solo shows to check in and share her story of her first year as an entrepreneur.

The Best Part About Podcasting

I share in Nicaila’s sentiment about the best part of podcasting. It’s all about that feeling we get when that new episode drops and people start listening and the feedback is just so positive. When we’re in the trenches and working on the show it’s easy to ask why I’m putting in so much work and if it’s even worth it. But then the show is released and the audience tunes in and we hear stories of how the content helped motivate or inspire people all across the country and world. That’s the best part. That’s why we keep producing.

Nicaila’s Final Advice

“If you’re thinking about starting a podcast, really tap into the ‘why?’ Sit down and think about if this is something that you want to do for the next year. If you can picture a year from now, two years from now what the podcast will look like, then you know you’ll still connect with it when it’s not fun.”

And most of all, “Do not talk yourself out of it.”

Wow. We really covered all the nitty-gritty of podcasting in this episode. For an even deeper look into the world of podcasting, how to monetize, what it’s really like to host your own show, tune into the full episode. What’s YOUR vision for your podcast?


Thank You to Goal Digger’s Amazing Sponsors

Get $5 Off Your First Poshmark Purchase with Code: GOALDIGGER5

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  1. Wow, what a great Podcast interview and there are so many parallels of how I got started and hope to obtain the same sort of success as an Encore Entrepreneur.


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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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