How Tarra Stubbins’ Take It Easy Group Turns Creative Chaos Into Structure

Repost from my Net Influencer Article:

When influencers become brands, many find themselves unprepared for what comes next: running an actual business. Tarra Stubbins saw that gap in 2017 and founded Take It Easy Group to help creators manage the operational chaos behind their online success. The Toronto-based company provides fractional executive assistant and chief of staff services specifically tailored to influencers, celebrity-backed brands, and creator-led businesses that have outgrown their basic operational systems. “I’m passionate about helping creatives build really great businesses,” says Tarra. The company serves what Tarra describes as “accidental CEOs,” i.e., creative professionals who find themselves running businesses without formal business training. “A lot of people in the creator economy have amazing creative ideas, and then they’re like, ‘Oh no, I run a business now. What do I do?'” Tarra explains.

From Rock Star Roadie to Business Strategist

Tarra’s understanding of operational challenges stems from firsthand experience. For a decade, she worked as a personal assistant to some of music’s biggest names, including the Rolling Stones, Kiss, Nickelback, Lady Gaga, and the Red Hot Chili Peppers. “I chased rock stars around the world for 10 years,” Tarra recalls. The high-pressure environment taught her valuable lessons about creating systems that could accommodate unconventional schedules and specialized needs. Her epiphany came in Shanghai while she was trying to convince the hotel kitchen staff to sanitize a rock star’s toothbrush in an industrial dishwasher. “They looked at me like I had three heads,” Tarra recounts. “I just remember thinking, ‘There’s got to be more to life than this.'” That moment catalyzed her decision to leave tour life behind and help “more than one crazy rock star at a time.” Without any formal business training, Tarra launched her first venture in 2007, focusing on personal concierge services. As she built her network, Tarra noticed that many founders struggled to scale beyond their initial success. “They could reach one level trying to piece it all together,” she says. “But it was hard to get to the next level with their mom doing bookkeeping and their aunt being their salesperson.”

Recognizing this gap, Tarra began offering strategic assistance, initially at no cost. Demand grew as businesses achieved breakthrough results, leading to the formation of Take It Easy Group as her second venture.

The Take It Easy Group Approach

Take It Easy Group’s services prioritize strategic thinking over task completion. “We’re a strategic, proactive partner rather than a task doer,” Tarra says. “We’ll do tasks, but we’re really your partner on the side.” The company’s service model begins with a discovery month, during which they familiarize themselves with a client’s operations to identify needs and develop a tailored solution. “We embed ourselves in your system as if we’re full-time and help figure out what package you need,” Tarra explains. At the end of this period, clients receive a detailed 30-, 60-, 90-day plan outlining how Take It Easy Group will support their growth. Unlike typical hourly-based services, Take It Easy Group operates on a subscription model. Tarra believes such an approach removes the stress many first-time delegators feel about maximizing billable hours. “A lot of people coming to us have never delegated before,” Tarra says. “They think, ‘I can do this faster’ or ‘I can just do this better myself.’” The subscription model also accommodates the reality that creators rarely operate on standard nine-to-five schedules. “Creators, former athletes, celebrities don’t run on a nine-to-five day,” Tarra points out. “It’s hard to have someone say, ‘I’m only available between 1 and 3 Monday, Wednesday, and Friday.’” According to Tarra, this approach can help clients free up 15 hours or more per week and achieve 20-30% revenue growth within six months.

The Costly Gap in Creator Operations

For Tarra, understanding the challenges facing creator businesses isn’t theoretical, but personal. Prior to establishing Take It Easy Group’s current model, she scaled a previous business to $750,000 in monthly recurring revenue (MRR), only to watch it collapse to $20,000 MRR in four months. “We were chasing the wrong metrics,” Tarra admits. “We were bringing in clients just to bring them in and hiring team members because we thought it was cool to have a bigger team.” This painful experience taught Tarra what many creators learn too late: impressive numbers on paper don’t translate to sustainable business operations. Without proper systems, even successful creators struggle to scale. “They start a business without realizing it,” she says. “Then it grows quickly, and they don’t have systems in place to sustain or scale it.” The consequences extend beyond missed opportunities. Many creators face burnout trying to manage every aspect of their growing businesses. “They barely have time to maintain what they’re already doing,” Tarra says.

Creating Operational Infrastructure

While many creator economy services help influencers secure brand partnerships, Take It Easy Group focuses on building the operational foundation for diversification beyond sponsored content. “We’ve helped creators start podcasts, merch lines, books, and courses instead of just focusing on brand deals,” Tarra says. For former athletes, this has included launching children’s books and non-profits. The company provides support across a wide range of areas. “We can help align team roadmaps and goals, handle minor bookkeeping, scheduling, travel, brand deals, whatever’s needed,” Tarra explains. For creators, Take It Easy Group has helped clients secure appearances on shows such as “Shark Tank” and “Dragon’s Den,” then manage the subsequent surge in interest. “After that, whether you get a deal or not, your business usually explodes,” Tarra notes. “But the founder is the one handling everything from product placement, deliverables, and packaging.” The value of this approach, Tarra adds, is that it allows creators to focus on what she calls “the biggest ROI [Return on Investment] in the business” while delegating all other tasks. “I’m passionate about helping founders focus on what brings the biggest ROI and delete what doesn’t,” she emphasizes.

The Philosophy Behind “F*ck the Fluff”

Tarra’s business philosophy is direct: “F*ck the fluff. Real talk, real impact.” It emerged from her frustration with the lack of concrete advice available when she was recovering from her own business failure. “I was facing personal bankruptcy because of loans I took to keep the business afloat, even though we looked great on paper,” she recalls. While trying to rebuild, she found that most success stories overlooked the real strategies used to overcome failure. “I tried listening to podcasts and reading books from successful people,” Tarra says. “But no one actually shared their thought process or how they got through the hard times. It’s always glossed over.” After hearing a top female entrepreneur credit her success to taking Sunday bubble baths, Tarra decided to build a brand focused on actionable insights. “I wanted to start something that shared my story, how I crawled out of the lowest lows, and help others by cutting the fluff.” This commitment to transparency extends to free resources for creators and founders. “Free resources help brands grow,” she says. “I try to share as much knowledge as I can so others don’t make the same mistakes I did.”

Challenges Facing ‘Accidental CEOs’

Tarra identifies several consistent patterns that prevent creative entrepreneurs from realizing their potential: “Holding on to everything themselves and not knowing what moves the needle,” is one, she says. “Another one is trying to have really big goals, but trying to ‘cheap’ their way to success, not invest in their success,” Tarra adds. “I’ve been there, trying to do everything for free or being scared to invest in myself.” Perhaps most essential is the lack of operational systems. “They don’t have systems for hiring or delegating. How will they manage six brand deals, a podcast, and a merch line?”

According to Tarra, the solution isn’t simply hiring more people. It’s implementing the right systems with strategic support. “If you have big goals, you need to invest in them. Investing in your team matters,” she says.

Professionalizing Creator Businesses

Tarra envisions a creator economy where influencers embrace professional structures. “I’d love to see more creators lean into it,” she says. “They can build better businesses faster if they treat their brands like real companies and themselves like CEOs.” This vision aligns with broader trends toward professionalization. The influencers who establish proper business operations today will be better positioned to adjust to changing market conditions tomorrow. For Tarra, this is both a mission and a business opportunity. Her goal is to turn Take It Easy Group into “the go-to spot for influencers building businesses and operational practices.” “I can’t wait till that trend takes off,” she concludes. “We’ll see so many more great creative businesses out there.”