How a corporate marketer pivoted to consultant and landed a hosting gig for Entrepreneur magazine

Terry Rice left his high-paying tech job to be a creator right before his first daughter was born.

I was worried all the time because I felt that her future was tied to the success of my business, and I had no clue what I was doing. 

Despite having an MBA and working on Wall Street and at top companies in Silicon Valley, Terry learned quickly that what was needed to help a giant global corporation succeed was a lot different than what he needed to do as a creator. 

I was very good at what I did – my technical skills as a digital marketer – but I was horrible at running a business. 

I’d written 20 business plans when I was in business school, but when it was time to actually do it, I just was horrible at it. 

His daughter was born on December 8, 2015. And then his dad died on December 20th. That Christmas, Terry felt lost, his business floundering, caught between the joy of his first child, grief for his father, and confusion about what he really wanted to build.  

 I knew it was time to reassess and make some kind of pivot.

That was seven years ago. Today, Terry’s creator business is going strong. He’s also the Expert in Residence, a staff writer, and podcast host for Entrepreneur magazine. 

Most of the content he creates is meant to speak to the person he was when he started his business seven years ago: a creator (or what he often calls a solopreneur). Now he shares with others exactly what he learned seven years ago that changed everything. 

“When you want something else, it’s confusing.”

Terry didn’t set out to be a creator, but after many years working on Wall Street and for companies like Facebook and Adobe, he looked up from his desk one day at everyone around him and thought, “I don’t want your job, your job, your job…” 

It never felt right. I always felt too constrained. I realized I didn’t even want my job.

But there’s a guilt that goes into that, because everyone’s like, “You’re doing so great and you’re doing better financially than other people.”

When you want something else, it’s confusing. 

Terry tried to push his desire for something else down. 

But then, when he found out his first daughter was on the way, he knew his current work lifestyle wouldn’t allow him to see her that much. 

We got free breakfast, lunch, and dinner; but breakfast ends at 9am and dinner doesn’t start until 6pm, so you’re incentivized to get there early and leave late. And I’m like, if I stay here, my daughter’s gonna call me Terry instead of dad.

He finally came to terms with the idea that there wasn’t anything wrong with the job itself, it just wasn’t right for him. Rooting himself in the idea that “a great job” and “a great job for you” are two very different things, he decided to take a chance and pursue the latter. 

He quit his digital marketing job at the big tech company and started his own consulting business, essentially doing what he did at the company, but as a freelancer: running online ads for people. 

There was only one problem with Terry’s new business. 

He quickly realized he hated running ads for people.  

“I tried it my way and failed, right?”

But that was what he knew how to do, so he kept doing it, and people kept paying him for it. 

He was making ends meet, but he didn’t feel like his business was really working the way he hoped. 

Then one day, a client asked him questions about how she could grow her business beyond running ads. 

He shared everything he knew about that stage of business development (like speaking engagements and content marketing), and what he taught her worked so well that she asked if he would consult with her husband, a graphic designer, who was great at his skillset but didn’t know how to market himself. 

“That was the light switch,” Terry remembers. He didn’t want to run ads anymore. He wanted to help creators with their business development. 

I wanted to focus on helping other solopreneurs like me with their biz dev, branding, pricing, promotion strategy, retention, and all the stuff I had no clue about when I first started. 

And Terry knew how to help them because of all the mistakes he made, like buying tools he didn’t need, cold emailing, and cold calling. He also says when he first started he struggled because he wasn’t on social media, didn’t have a newsletter, and wasn’t building his personal brand at all. 

I would just reach out to people talking about myself the whole time, not seeing how I could help them. Like “Hi I used to work at Facebook and Adobe, I’m an expert, give me money.” 

Everything changed for him when he got help from another creator, Dorie Clark. He read her book Reinventing You, which, Terry says, outlines a clear step-by-step process on how anyone can transition from corporate to creator. 

I tried it my way and failed, right? So I followed the steps in her book.

Before he read Reinventing You, his business was making about $3,000 a month. Slowly but surely, as he implemented what he learned, things changed.

The moment he realized it was working was when, for the first time, a big client sought him out (versus the other way around) and offered him a $20,000 per month retainer. 

The only catch was, they wanted him to come to their office every day. 

I said no, because the reason why I started my own company was to spend more time with my family and have more autonomy. 

It would be another year before I ever made $20,000 in a month. But it happened, and it happened on my own terms and with me doing it remotely.

Once he realized how much easier (and more fun) it was to have people coming to you because of the brand you built online and the helpful content you give away, the more he became hooked on growing his own business and teaching other creators who were going out on their own for the first time. 

Terry started an email list and wrote his first book (called Start Your Own Consulting Business) to start building a relationship with the audience he was excited about helping. 

And little did he know that taking his daughter to a free gymnastics class in 2018 would give him an opportunity and platform to connect with creators beyond what he could’ve ever dreamed. 

“It’s not by asking, it’s by giving”

By 2018, Terry had two kids, and one morning, he took his daughter Lena to a free gymnastics class in Brooklyn. When he walked in, he immediately recognized one of the other parents– Jason Pfeifer, the editor in Chief of Entrepreneur magazine. Terry recognized him because he’d been reading his work and listening to his podcast for years. 

He wanted to talk to him, but was nervous. 

But, he just couldn’t shake the feeling that he needed to say something to this person whose content had had such a positive impact on his life and business. Terry went up to Jason before he could change his mind and told him how much he liked his podcast.  

Jason was floored, “You actually know who I am?” 

They had a friendly exchange in person and then kept the conversation going on social media, where Jason suggested they meet for coffee.

All Terry remembers about that first coffee is how nervous he was and how he drank too much coffee and was shaking the whole time. But Jason didn’t seem to notice. He told Terry about some of the new things Entrepreneur was working on, like a program for people to book experts for specific business advice. 

Terry checked out the website for the new program and noticed there were some things they could add to improve the conversion rate for the site. He made a quick Loom and sent it to Jason in case it might help. 

They’d built a solid relationship at this point, and Terry knew from their conversation this was something that would be helpful to Jason. Gone were his old habits of cold emailing or imposing.

Jason did find the video helpful. In fact, Terry could see that Jason had shared it via Loom’s view analytics. And sure enough, Jason reached out saying, “Thanks for making this video. The team would like to meet with you about some marketing needs we have. Can you come in next week?”

Terry tells me that he still has imposter syndrome sometimes, a little voice saying “all I did was walk into a gymnastics studio.” But that voice seems to ignore the work he did to turn that chance encounter into something more, and that his own deep engagement in the content he loved is what made it possible for him to even recognize Jason and start that relationship in the first place. 

But most of all, what that experience taught him, something he teaches the solopreneurs he works with, is: “That’s how you start relationships. It’s not by asking, it’s by giving.”

“Do I deserve to be here?”

To date Terry has written 60+ articles for Entrepreneur magazine and hosted 15 podcast episodes.

He was terrified at first, but found strength in a line from the film Defiant Ones. One character talks about questioning, “How am I here?” then replaces that with, “Well, I’m here now, so let’s do it.”

If you spend any of your energy thinking “How am I here? Do I deserve to be here?”, you’re in trouble. So I encourage people to jot down what I call “epic thoughts,” which is just reminding yourself of difficult things you’ve done in the past.

Confidence comes from past experience, not pep talks or motivational posters. 

As his confidence grew, so did his business, and his email list. And in 2020  he switched to Kit.

In the early days he says he bought too many tools he didn’t need and shares how he changed the way he vetted creator business tools:

I look for people I respect and see what program they’re using; I use them as the filters to block out all the noise. So I looked at Pat Flynn and Dorie Clark: these very smart, very successful people are using Kit, so that’s what I’m going to do.

Years ago, if you wanted to do email marketing you had to hire someone. Whereas now, tools like Kit democratize access to entrepreneurship by making it so easy that anyone can do it.

But of course that doesn’t mean it’s all easy. Terry struggled with email early on.

I was just promoting my events and saying, “Hey, here’s this thing I’m selling.” I wasn’t building relationships.

But two things changed for me. One: I realized I would not read my own newsletter. So I said, “Look, go back to that guy you were seven years ago. You just wanted information that would help you save time, make money, and avoid burnout.”

Now my newsletter is structured in a way where every week you get one thought, one tactic, and one time saver to help you save time, make money, and avoid burnout. 

People look forward to it. And it also helps me write it because I can just kind of plug in each module. So it goes a lot quicker. But what I’ve also done is shared my personal stories more. 

He judges the success of his emails by the quality of the responses he gets back. 

For me, that’s a main KPI that I think many creators don’t really consider enough. They think, “Oh, am I getting opens, clicks, likes, follows.”

Are you getting responses? Are you starting conversations? 

He loves those quality responses, because it’s turned email into something he enjoys now.

I just look forward to it. It’s an integration into my life, not an interruption. 

If you can just find that alignment with your content you’re in a good spot, because then it doesn’t feel like a chore, it feels like an opportunity to express yourself. 

“You’re not burning bridges, you’re just taking a break.”

Once Terry had four kids, he realized his work life would almost always have some kind of interruption; there would be no “going back to normal.”  Getting interrupted was his new normal, so how could he make that work? 

That’s when I knew I had to build my passive revenue streams.

But to have time to create something valuable enough to be recurring passive income, he realized he’d need more time than he currently had. 

I was doing very lucrative things like contracts that were $25K a month, but I realized, I can’t do this anymore. Because I need to work on my online course. And as a result of that, over the long run, I’ll make much more money and have more time with my kids.

Of course, there is no guarantee, and he remembers the sheer panic he felt the first time he let go of some of his biggest client work and saw his revenue dip.

But in those moments he always reminds himself that he’s done this before, and that he can always go back to what he did before. “You’re not burning bridges,” he’ll remind himself, “you’re just taking a break.”

Terry shut down his most lucrative contracts and focused for six weeks on building his online course.

Not too long after creating and then launching that course, he got a notification that he made course sales from an automated email that went out while he was at the playground with his kids. 

He got his kids ice cream that day.

“If you’re always busy doing, you don’t have time to be present.”

In the corporate world, success was defined by profit and loss statements. Today, Terry defines success by the time he spends with his kids and the freedom he has to focus on work that he cares about. 

Terry could (and did for a time) make a lot of money working for well-known global corporations, but he made a decision a while back to stop working for those clients and focus almost exclusively on working with solopreneurs.

He enjoys making a direct impact on other people’s lives (and their family lives), the same way Jason Pfeifer made an impact on him. 

He also appreciates the opportunity to design his schedule the way he chooses. Spending time with his kids is an obvious part of that, but now he also has the chance to meet his full creative capacity, doing things like scheduling in lots of margin. 

He references a Forbes study done of corporate executives that said 97% got their best ideas during white space in their calendars, but only 4% blocked off time to create margin.  

As a creator, I think sometimes it can be feast or famine, especially initially, so when you get work, you’re like, “Okay, I’m gonna go all in.”

But now I protect that white space, that 2-4 hours a week where I’m just existing, and don’t need to fill it just because I have it available. Because the results from that time can be exponential. 

If you’re always busy doing, you don’t have time to be present and focus on who you are and what you want to do.

Terry’s ultimate dream-come-true, he says, happens on the weekends when he’s hanging out with his kids, actively playing with them on the playground, totally present.

Though one time he was taken out of the moment when someone came up to him while picking up one of his kids from daycare asking, “Are you Terry?” 

“Yeah,” Terry answered, a little confused.

“I follow you online!” the guy said happily, thrilled to meet someone whose content had made a difference in his life. 

You can connect with Terry on LinkedIn, subscribe to his newsletter, or learn more at terryrice.co.