Rob Dyrdek is a former pro skateboarder also known for hosting hit TV shows including Rob & Big, Ridiculousness, and Rob Dyrdek’s Fantasy Factory. He founded business incubator Dyrdek Machine and hosts the “Build With Rob” podcast. During our conversation, Rob talked about his journey from being a skateboarder to building his businesses.
In your early 20s, you gained fame as a professional skateboarder and were able to travel the world. Despite your success, why wasn’t skateboarding giving you the purpose and fulfillment you were seeking?
It wasn’t as much about the sport itself not giving me fulfillment, but I began to grow out of it because my true passion was creating and bringing ideas to life, and I had maxed out what was possible within skateboarding itself.
I looked at myself as a brand at a really early age, and turned pro when I was 16. I was around when we created the Alien Workshop, and that was the company I turned pro for. T
You’re part skater, part TV personality, and part entrepreneur. How were you able to turn your success as a skateboarder into a series of TV shows and into multiple businesses and partnerships?
At 14, I skated for a local skate shop whose founders started all of these companies. So even as I was turning pro, tracking all my own finances, and considering myself a brand at that early age, I was still watching companies get created.
I built my first company when I moved to California, when I was 18. My skateboarding career led to launching DC Shoes. And then the DC Shoes video led to a skit for a skate video, and that evolved into a television show on MTV.
That whole time I was constantly creating and building different businesses through the MTV platform, while being a pro skateboarder and creating new television shows. For me, this idea of business has always been the through line, and how do I maximize the opportunity that’s presented to me.
You’ve brought your family and friends with you, much like we saw in HBO’s Entourage series. How has involving your best friend and cousins in your projects deepened your relationship with them, and what have you taught them that has helped improve their careers?
For any business and anything that you create, meaningful relationships are at the core of it being fun. I’ve always been really clear on that. During my diligence period, right before I pull the trigger to decide whether I’m going to create a project with someone, it really boils down to: Do I want to be connected to them for life?
I am passionate. I am driven. I am focused. I am clear. But more than anything, I want to enjoy everything that I do. And any time I get through a process with someone where I can see we’re rubbing each other the wrong way or our energies aren’t connecting, then I just won’t do it. With so many businesses and projects happening simultaneously, how do you manage your time and decide what projects to invest or divest in?
I look at life as this series of interconnected systems that all need to be aligned, integrated, and expanding in the same direction – and that direction is towards your ideal life. But it’s a balanced life, by design. It’s choosing the right projects, and how you actually live in those projects.
My entire existence, from the way I create companies to the way I shoot television, is fully systematized and automated. I have an 80-page document called The Rhythm of Existence that is the operating system for my life. At the end of the day, your energy is basically everything that you have, and that excitement about life and absolutely enjoying everything you’re doing is really what I’m hoping to achieve.
What’s your best piece of career advice? I think the best piece of career advice is that you’re not building a career, you’re building a life. It’s finding the balance between who you are as a person – your passions, your physical strength, your happiness, what fulfills you – and the way that you earn a living, that feeds that purpose and who you are, and then how you want to live.
I think a lot of times, people don’t look at themselves as multidimensional beings that require all of these different aspects in order to be happy and balanced. They think their career is going to be the answer for the life that they want. But your career will never be the answer. It will be a part of the answer, and if it’s integrated into who you are and how you live, then you will truly be balanced and happy.
I’m a risk-taker. But leaving my high-paying job at a tech startup in 2012 with a one-week old baby – with no plan – meant my family’s income went from comfortable to zero overnight.
My husband was developing a wind farm in Chile and not getting paid. But I knew I needed to leave the toxic workplace I’d been in for two years.
Nine years into running my business, a brand story and content strategy firm, I’ve had time to look back on the mistakes I made, the stints of success, and the six things I wish I’d known before going out on my own.
1. Nobody is their strongest alone
Early on, a phone call to my old boss landed me multiple massive content projects for several large companies. So in the first few years, I didn’t have to work hard to get clients – which meant I also became overly confident. Eventually I had nothing in place to help me get more work, but I was stubborn, wouldn’t admit that I was frustrated, and didn’t seek out a mentor because I thought I knew everything or could figure it out on my own. This caused me to lose several years of growth and income.
In the past few years, I’ve joined a mastermind group, read and listened to countless business books and podcasts, and have taken close to a dozen online courses – all part of my quest for mentorship.
2. Normalcy isn’t the goal
Fitting in is the best way to be forgotten. After a client chose not to renew my contract because I “wasn’t 100% necessary” for their growth, I took a business course online. It made me realize everything I was not doing – like differentiating myself .
My first task was to define my “Dream 100” – the list of people I really wanted on my client list. Easy. Then I had to define what my secret sauce was that would make me different. It took me six months to nail down the process I’d used with past clients and put it into a legible framework I could sell to a higher number of different clients.
3. Fail quickly, fail often
My dad used to say, “you never learn less” after anything disappointing happened to me, and it would drive me insane.
But after getting humbled several times as an entrepreneur (ie. losing a job bid), I realized he meant that experimenting is how you find your edge, even when some of those experiments completely bomb. Once I accepted that failure was inevitable, I felt less trapped by perfectionism and more free to try new things, create new programs, and go after my “Dream 100.”
4. Be more interested than interesting
Years into my business, I started listening aggressively to my ideal clients, and moved from trying to be interesting myself to being wholly interested in what they needed. This moved my client roster from start-and-stop to a steady stream, and thus recurring revenue.
5. Be prolific
A few years back, I went back to my roots and started writing again – this time with a strategy. I began penning blog and guest posts for brands and entrepreneurial magazines, sending weekly emails, and answering HARO requests. This has allowed others to see how I work and think, what frameworks I use, and how I impact others, which has led to even more opportunities. Just recently, an article I wrote got selected to be in a book being published by Thrive Global.
6. The back of the statue matters
When I first started working solo, I hated all the unsexy stuff that needed to happen on the back end of my business. But when I started to have a referral drought, I admitted that having no system (the back of the statue) was impacting my reputation and positioning (the front of the statue that people could see). It took months of toil, late nights, and a full-time virtual assistant to get my systems dialed, but now I communicate my process with clarity.
Lindsay Yaw Rogers coaches high-achieving entrepreneurs and athletes on how to create powerful brand stories to to stand out, create partnerships, and position themselves as a leader.
When I first had the thought seven years ago of starting a business where strangers could hire me to be their bridesmaid, I wasn’t sure if it was a good idea. So before putting any money down, I decided to figure out if people would actually hire a stranger for their wedding day.
I did competitor analysis and couldn’t find any similar businesses online, so I took it a step further and asked my potential audience. After posting an ad on Craigslist, I received hundreds of messages from people all over the world who wanted to hire a professional bridesmaid.
I decided to invest in making a website, build a business plan, and create a list of different services I offered. Fast-forward, I’m now running a successful business that works with hundreds of clients every single year. Here are six ways I recommend fellow aspiring entrepreneurs test out new business ideas.
1. Write out a business plan
Map out a business plan that includes details about your target audience, industry analysis and research, how you could scale the business in six months or a year, and what your competitive advantage would be.
As you go through this process, your idea might pivot as you find out about similar companies or emerging industry trends.If you’re not sure where to start, download a free business plan template and brainstorm how you’d fill in each section.
2. Figure out the problem
Ask yourself two questions: What problems does this business idea solve, and do people actually care enough to spend money to solve these problems?
This a brainstorming gut-check to see how urgent of a business idea you have.
For example, I was thinking about starting a business around a glove for carrying a cup of hot coffee, rather than a cardboard sleeve or a cup that traps the heat that may burn your hand. But after writing down my answers to the two questions, I realized it was unlikely people would buy something new like this when other solutions out there fixed the problem well enough.
3. Research industry trends
As you’re building your business idea, keep a pulse on what’s going on with the industry. What new technology is being introduced? What does customer behavior look like this quarter? What new companies are emerging?
Read industry blogs or publications weekly, subscribe to podcasts from industry experts, and set free Google Alerts to get a daily recap of what’s happening.
4. Eyeball potential competitors
When I was thinking about my coffee glove business, I made a list of competitors who were also solving the problem of coffee cups being too hot to hold.
I researched each company, noting things like their branding, marketing efforts and social media, user design flow on their website, and customer experience. I made a list of what each company did well, what they did that wasn’t so great, what my company could do that was better, and any other competitive advantages.
5. Ask questions to your audience
Getting feedback, suggestions, and even hearing excitement from your potential audience is a great way to gain perspective on your business idea.
Find where your potential audience is having conversations online and join in. For example, I use Quora, Reddit, and Facebook groups to locate my audience, browse the questions they’re asking, and use that insight as a way to enhance my business.
6. Find beta testers to test out your idea
This step requires that you have something for people to test, whether it’s a sample of the product or a soft-launch of the website or mobile app you’re creating.
Set up a way for them to give real-time feedback during every step of the experience. This information will help you fix any holes in your process and get your business ready for more consumers to enjoy.
Having an idea for a business is a powerful and exciting moment. Before you put money behind the idea and launch it, spend time experimenting to see if it’s a viable business that will be as successful as you want it to be.
“It’s a shorter list to tell you what we wouldn’t fund than what we do fund,” Thom Ruhe, NC IDEA’s president and CEO, told Insider.
The Durham, North Carolina-based organization supports entrepreneurship and economic development across the state through grants, seed funding, mentoring, and other programs. Last year, it distributed about $3 million to entrepreneurs – and plans to provide $3.5 million more this year.
Durham is a “national case study for what an entrepreneurial ecosystem can do,” and the region has long been a center for innovation, Ruhe, who previously directed entrepreneurial programs at the Kauffman Foundation, said.
“There’s a lot of collaborative energy here, more than I’ve experienced in other markets,” he said. “It’s refreshing and productive. I know it’s cliche to say, the rising tide argument, but it really has helped here.”
Here’s a look at how NC IDEA invests in entrepreneurs, who the organization believes transform communities and boost local economic development.
Broadening its reach to help more entrepreneurs
NC IDEA is a private foundation that was created in 2006 under the Council for Entrepreneurial Development, a nonprofit connecting North Carolina entrepreneurs to the resources they need. It became independent in 2015.
Unlike other foundations, such as the Gates Foundation or Kauffman Foundation, NC IDEA doesn’t have a benefactor, Ruhe said. The primary source for its endowment came from an equity investment that the state of North Carolina made in the 1990s and liquidated in the early 2000s.
To protect the investment, the private foundation was established to economically empower people through entrepreneurship. NC IDEA’s endowment is invested, and the investment income funds the organization.
Recently, the organization began fundraising, which Ruhe said is “very unusual for private foundations because we’re considered self-funded.” NC IDEA wants to increase its budget so it can fund more companies and cover the administrative cost of reviewing additional applications.
“We could see a greater return if we simply had more budget to allocate,” Ruhe said. “We’re trying to take that message out into the economic development and philanthropic communities within North Carolina to say, ‘If you think there’s value to North Carolina and the activity that we do, you can help us increase the yield by just increasing our programmatic budget.'”
Giving grants to businesses and organizations helping startups
Many foundations either operate programs or provide funding. NC IDEA is unique in that it does both, Ruhe explained.
“Our grant-making is better for what we learn in our programmatic activities, and vice versa,” he said. “All of our programs and grants are targeted at helping people live up to their entrepreneurial potential, and in a broader context, make North Carolina the best state in the nation for people to start and grow firms of economic impact.”
NC IDEA operates two categories of grants. Seed grants and micro-grants of $50,000 and $10,000 are provided directly to entrepreneurs or startup founders.
Grants are awarded to founders to whom the money would “at this particular time be very impactful in their ultimate success,” Ruhe said. It provides assistance to get ideas off the ground or help companies scale to the next level so they can create jobs and generate tax revenue for the state. The grants don’t need to be paid back, and the organization doesn’t receive equity in the business.
Another category of grants is what Ruhe calls B2B, where NC IDEA supports other organizations that help entrepreneurs, such as universities, two-year colleges, cities, counties, and others. The organization has about 60 partners in its network.
Supporting underserved communities
NC IDEA recognizes that economic development in North Carolina is not a one-size-fits-all approach, and the organization strives to support underserved communities. Grants are distributed based on what’s relevant in different parts of the state, whether it’s educational programs, access to capital, or mentoring.
“We have to meet people where they are and help them from that starting point,” Ruhe said. “The best way we could do that was the creation of this ecosystem partner program where organizations that are on the front lines in various parts of the state say, ‘Here in our corner of the state, this is what’s most needed.'”
NC IDEA also created the North Carolina Black Entrepreneurship Council and has committed $1 million to advance Black entrepreneurs in the state. The council and foundation will work together to identify and recommend programs, grant recipients, and partners.
Another program, NC IDEA SOAR, aims to support women in entrepreneurship. The program offers networking, professional development, and connections to resources to help female founders grow their businesses. There’s also a four-week program called NC IDEA LABS that’s open to anyone wanting to take their business to the next level.
SOAR and LABS are “traditional accelerator”-type programs, Ruhe said. “It’s specific business-growth assistance around market valuation, customer discovery, lead generation, revenue generation – all the nuts and bolts,” he added.
NC IDEA delivers its programs at no cost, but Ruhe said there’s a competitive application process that involves companies providing details about its founders, the company as a whole, revenue, funding, and the type of grants they’re seeking. The organization receives hundreds of applications during each application period.
Growing North Carolina’s innovation footprint
Since its beginning, NC IDEA has provided about $15 million to companies and partners throughout North Carolina. Ruhe added they’ve supported nearly 500 companies, which have created more than 3,300 jobs and brought many benefits to communities.
Marrying innovation and entrepreneurship offers the biggest economic impact, and he said the state of North Carolina does well cultivating both. As word gets out about the state’s entrepreneurial ecosystem and it keeps attracting major tech companies like Apple and Google, the region has even more potential for up-and-coming entrepreneurs.
“The greatest natural resource that exists is the entrepreneurial spirit of people,” Ruhe said. “It’ll be entrepreneurs who will solve our biggest problems. It’s entrepreneurs who are creating the companies that create the jobs we so desperately need. That’s why we do what we do.”
In the movie “Sliding Doors,” Gwyneth Paltrow’s character follows two parallel storylines.
If she catches a train, her life takes one path. If she doesn’t, it leads in another direction. The film shows how a small, seemingly inconsequential change can drastically alter the course of your life.
Startups have sliding door moments, too. Over the course of building your company, you face several divergent paths. Some are obvious at the time, some only become clear in hindsight.
At Bleacher Report, we faced many such decision points. Two in particular stick out.
In the early days, our approach to content moderation was lax to non-existent. While everything published to B/R needed a sports angle, we took a loose interpretation of that lens.
As a result, the site had its fair share of unsavory content. This included posts and photo galleries that objectified women in sports. They had headlines like “Hottest WAGs (wives and girlfriends) in the NHL” or “25 Hot Cheerleader Pics.”
Looking back, I’m not proud to have contributed to the already misogynistic culture of sports. We accepted these posts as part of the “authentic fan conversation” encouraged within our community. In a development that should surprise nobody, they became some of our biggest traffic drivers.
So in a regrettable move, we took it a step further by launching a standalone section for this content called “Barely Sports.” Cringeworthy, I know.
According to our logic, giving this content its own section separated it from our more sports-focused coverage. After all, we told ourselves, if Sports Illustrated had a swimsuit issue, why shouldn’t we have Barely Sports?
But we failed to recognize that by creating the section, we encouraged and legitimized more of this content. When Barely Sports launched, we got some notes from disappointed readers. And while I’d like to say that negative audience feedback was enough to sway us, the reality is a bit different. We changed our minds about Barely Sports not because of morals, but for money.
Our newly hired head of ad sales made nixing Barely Sports his first priority. To land deals with major brand advertisers, B/R needed to clean up our image. And that meant getting rid of the T&A.
Money talks. Barely Sports bit the dust.
We were all in on brand advertising as our business model. And we knew deep down that the B/R brand would be stronger if we took a more inclusive approach to sports fandom.
Around the same time, another digital sports publisher picked up traction by taking things further than we ever did. I’m talking, of course, about Barstool Sports. As B/R took a more centrist approach to covering sports fandom, Barstool leaned into the extremes. And they built an incredible business doing so.
Barstool pulled off the strategy that B/R abandoned by making two critical innovations:
Barstool avoided depending on advertising as their only business model. Instead, their DTC approach cultivated an army of hardcore fans and monetized them directly.
To buttress the brand against controversy, Barstool put the personas of their creators front and center. Rather than journalists or commentators, they branded them as outrageous characters straight out of pro wrestling storylines. If Barstool is the WWE, then Dave Portnoy is their Vince McMahon.
They played their game, we played ours.
Almost The Athletic
A bit later down the road, B/R faced another crossroads that could have altered our journey.
From early on, we viewed B/R as the sports fan’s replacement for declining local media. We talked about it in our very first fundraising pitch. With local newspapers collapsing and sports pages contracting, we planned to fill the void by empowering fans, bloggers, and up-and-coming writers to cover their teams.
But as the future we predicted played out, we saw a new opportunity: What if we hired displaced writers from local sports sections?
Many well-known beat reporters and columnists were losing their jobs and looking for new homes for their bylines. Hiring them could improve the quality of our coverage, bring some of their audience over, and boost our legitimacy. We seriously considered the idea. But after debate, we decided it wasn’t for us. Again, our business model was a major consideration.
These sports journalists were well-known in their local markets. But their name value didn’t register with the national advertisers we worked with. On top of that, our positioning in the market placed B/R as a fresh, young voice in sports. Hiring away experienced writers from the sports media establishment would dilute that story.
So instead we doubled down on hiring web-native writers who fit our mold. By establishing B/R as the place for fresh new voices in sports, we cemented our status as the place for big brands to reach younger sports fans. Of course, we weren’t the only ones to recognize the opportunity in realigning local sportswriting talent. I wasn’t surprised when a few years later, The Athletic emerged and gained momentum.
What made The Athletic’s approach to the opportunity work? It’s the business model, stupid.
Rather than advertising, they built everything around paid subscription. By quantifying the number of subscribers each new writer could bring, they knew exactly how much they could pay for talent. And their market positioning as the replacement for the local sports page was crystal clear.
It’s fun to reflect back on these moments. In an alternate timeline, Bleacher Report could have ended up more like Barstool. Or The Athletic. But, as far as we know, we only have one timeline.
Everything worked out great for Bleacher Report. So I guess you could say we made the right choices.
When startups face these big decisions, they’re often framed in the most high-stakes way possible. One path could lead to success and riches. The other to failure and ruin.
The reality is a bit more nuanced. In most cases, both paths are viable. The key is heading in the direction that makes the most sense for your mission and business model. And remembering, too, that your competitors face their own forks in the road. Depending on the choices they make, they may cease to be competitors at all.
The internet contains multitudes. Even for digital sports publications, there are many paths to success. So don’t worry about the paths not taken. Focus on the one you’re on.
Dave Nemetz is the founder of Bleacher Report and Inverse and an expert on growing audiences and building communities. He writes a weekly newsletter about building and selling startups, growing audiences, and the mindset and creative processes employed by prolific makers.
Even the website for the streetwear brand and creative agency, where you’ll see much of the merch mentioned above is sold out, is a play on the gossip website TMZ, filled with satirical articles and ads.
“Sometimes we’re not even sure if it’s going to connect with people all the time,” said Nick “Stove” Santiago, one of the brand’s millennial cofounders. “We’re trying and having a good time with it. And it works.”
Work it does. Pizzaslime has gained traction among Gen Z and DJs alike, appearing on influencers Emma Chamberlain and Addison Rae and on Diplo and Skrillex. While Pizzaslime found cult fandom in its early days, cofounder Matthew Hwang said it exploded during the pandemic thanks to the rise of TikTok, where Pizzaslime has 1 million followers.
The merchandise line, founded in 2013, has acted as both a sly observer and ironic commenter on political, economic, and cultural moments that have gone viral. By offering an implicit critique on media consumption and internet and celebrity obsession, the merch itself tends to go viral.
In 2020 alone, the clothing side of Pizzaslime raked in $2 million in sales, peaking in April, according to screen shots verified by Insider (they declined to share total business revenue overall). That’s a lot of stonk for a brand with only two employees: the 33-year-old Stove and 34-year-old Hwang.
The pandemic has only thrown up more memes for Pizzaslime fodder. “When all the WallStreetBets stuff was happening, it was energetic,” Stove said. “Me and Matt were waking up at six in the morning to text each other about stocks. Like we were in it, you know, it’s real and authentic to us. And that was the [thing] we thought would be funny to make.”
The result: a typically Pizzaslimish graphic tee featuring a mashup of things easily identifiable by the young and internet-savvy: the logos of Reddit, WallStreetBets, and Gamestop; a fat pile of money; a stock board; and Elon Musk’s famous tweet, “Gamestonk!!”
Pizzaslime’s success has propelled them to new ventures: the launch of a record label with Diplo last spring, their New York Fashion Week debut in February, and an expansion into film television. At the center of it all is the internet.
The art of meme fashion
Stove and Hwang met as coworkers, doing marketing and creative direction at a music management company, but not all their merch ideas fit the artists they were working with. So they decided to make T-shirts for themselves, wearing them backstage at concerts or events, and the entertainment crowd gravitated toward their designs.
As they tell it, the Kardashians were wearing Pizzaslime’s Gucci-Versace-Louis Vuitton mash-up at a Kanye West concert. “Kris Jenner just turns around, and is like, ‘I love that shirt,'” Hwang said. “So I was like, ‘Oh, OK. Let us contact you.'”
These organic moments of “being in the right place at the right time,” as Santiago describes it, put Pizzaslime on track to being the internet-savvy brand it is today. They count the Gucci-Versace shirt as their first big streetwear hit. Since then, their merch has flown off the site, from their Crocs collab that repurposed the shoes into crossbody bags for $300 to their “Stop looking at my” line, famously worn by Billie Eilish.
Pizzaslime has tapped into the emerging trend of meme fashion before the powerhouses caught on, with major players from Balenciaga to Maison Margiela now in the space, Morgane Le Caer, content lead at global fashion shopping platform Lyst, told Insider.
“Virality has become one of the key factors in determining the success of fashion products,” she said. “What matters to younger consumers is what captures their attention and has the ability to spread like wildfire across social networks – and this is exactly why meme fashion is so popular.”
Santiago was hesitant to use a buzzword like “authenticity” but acknowledged he couldn’t find a better term. “There’s a real rawness and authenticity to what we do,” he said. “We aren’t afraid to make a statement or post something and lose 1,000 followers.” He added that this caught on with Gen Z because it relates to authenticity more than his own generation, which he finds a bit more susceptible to marketing.
“It’s hard to define what Pizzaslime is,” he said. “For some people, it’s sort of like a barrier of entry they find confusing. At the same time, it’s given us the ability to build all these verticals and do everything and try everything.”
But that’s not to say Pizzaslime lacks strategy. “We’re not just sort of like throwing darts to the wall,” Santiago said. “The strategy really comes in with like, OK, now, how do we present the idea? How do we get this out there?”
The power of being undefined
Pizzaslime’s greatest strength is its lack of definition.
The verticalization allows them to move in all sorts of spaces differently. The work, Santiago said, is figuring out how all of these verticals intertwine to fit into the Pizzaslime ecosystem.
“We don’t have to think like a traditional clothing brand because we also act as an agency and we’re developing TV shows,” he said. “It’s just all feeding each other and having a division for that, so what we’re really doing is building our Willy Wonka factory.”
While the internet informs and inspires its creative decisions, it also helps them figure out what sort of strategies and mechanisms they want to try with clients like Crocs or Paramount Pictures for their marketing arm. Santiago likened it to a proof of concept – trying things with their own brand, only to apply those discoveries to the agency side.
Building out these verticals has put Hwang and Santiago at full speed. When asked for some of Pizzaslime’s key turning points over the years, they took pause.
“We’re going like a billion miles per hour because we’re doing so many different things at the same time,” Santiago said. “These are interesting reflection points where like, ‘Oh, right now I feel like I’m slowing down and processing this.’ It’s hard to pinpoint those moments because I’m always onto the next thing right away.'”
That they are. They’re currently working on a TV project that Santiago described as an “internetty” version of “American Idol,” all while collaborating with Amazon on a new animated TV series called “Fairfax.” And the first song of their record label, they said, just crossed 75 million streams on Spotify.
They plan to start plugging more into the label, looking at how they can tie music to products and build trends through products and sounds on social media, such as incorporate music from their record label into their TV show or collaborating with artists to put merch on Instagram. “If we’re working with a client and they want to make a TikTok campaign, we have the record label and the ability to make that TikTok song also a real song released through our record label,” Santiago said.
While they’ve been approached by venture capitalists, they said they’re taking the time to find the right strategic partners that would help scale up Pizzaslime.
“We want to jump into spaces and places that don’t have strong internet voices or tones like we do,” Santiago said, adding that he wouldn’t be surprised if you can find Pizzaslime skincare at some point. “We want to do some pretty unexpected stuff.”
On March 29, Tino Masaya posted a tweet that sparked a debate on Twitter.
“A 9-to-5 job is not slavery. Leave us alone. Not everybody wants or can be an entrepreneur,” the 30-year-old UK native tweeted.
Masaya, who works for her local city council, told Insider that she tweeted her statement because she was tired of the narrative, especially peddled on social media, that everyone has to be an entrepreneurial “hustler” with multiple streams of income.
It got over 11,000 likes, nearly 2,500 retweets, and over 200 comments. “Somebody had to say it,” one person replied. “Entrepreneurship isn’t for everyone.”
“When entrepreneurs say this, it tells me a lot about how they treat their own employees,” another commented.
Weeks later, the conversation was sparked again by an April 17 video in which a group of people debated which was better: a more traditional job or the path of entrepreneurship. “Your nine-to-five cannot sustain you,” one person said in the clip.
But Masaya said her nine-to-five does sustain her. She’s fine with having a boss and waking up at 8 a.m.
So is Simone Noble, who ran her own consulting company for about a year before moving to it part time. She loved the freedom it gave her, allowing her to set her own schedule and spend more time with her family.
But she didn’t like having to chase down money from her clients to pay the bills. Relying on this income, she was plagued by anxiety: Would she be able to pay for food, for her car, for her home? Eventually, she decided it was too much.
“Having to run around looking for ways to make money – that’s not for me,” she said. Noble went back into the full-time flow of a nine-to-five, where she has a boss and a more reliable income. Her business partner still runs the consultancy full time.
Entrepreneurship is glamorized on social media, where a crop of self-made creators document their lifestyles and career successes in real time. To the outsider, they appear to make quick money from their endeavors, but social media paints an overly rosy portrait of the true entrepreneurial experience, which is often gritty and unrewarding. Almost half of entrepreneurs reported struggling with mental health – and the true number is likely much higher.
Current and former entrepreneurs, as well as work coaches, told Insider that social media places undue pressure on people to become self-made by pursuing their passion. They agreed that a nine-to-five can provide a stable career path and also be rewarding, despite the online narrative. They added that the pandemic is redefining traditional work to be more flexible for employees, thanks to a widespread desire for a more entrepreneurial life and changes in work life.
Social media glamorizes what the life of an entrepreneur is like
Ruiz, an entrepreneur in Atlanta, makes six figures a year from her cosmetic companies Fash N’ Lash and Curl Candi, which she started at the age of 24. But these days, she’s dealing with what she calls “entrepreneurial depression” from trying to keep up with supply and demand, and from the pressures of running her own company. “It’s an emotional roller coaster,” Ruiz said.
“Social media can make everyone feel like they have to be this boss entrepreneur, but businesses are not for everybody,” she said.
Ruiz is referring to messaging from groups such as “LLC Twitter” or “Roc Nation Brunch Twitter,” where a flood of followers – many of whom were inspired by the success of the mogul Jay Z – encourages others to chase an entrepreneurial life and invest any gains for the chance to seek higher returns. But it takes courage and patience to launch a business, Ruiz said – not to mention capital.
“Social media can make everyone feel like they have to be this boss entrepreneur, but businesses are not for everybody,” she said.
As her own employer, Ruiz has no fixed schedule, and making payroll is solely dependent upon customers, rather than a corporate enterprise. This means there are good months, but there are also months where she’s left worrying.
Entrepreneurial depression is “real, and it’s not talked about enough,” Ruiz said.
Despite this, she has been earning six figures. But social media makes that success feel inadequate. “It makes us feel like we aren’t doing enough,” Ruiz said. “I’ve been an entrepreneur for three years, and I haven’t made a million dollars yet.”
There are benefits to having a 9-to-5
Michael Greenberg, a serial entrepreneur in Denver, said social media has made it easier than ever to make money by equating an online persona with a moneymaking business.
“There’s a media machine built around the idea that you have to be hyperproductive to succeed, and that if you’re not hyperproductive, you’re somehow falling behind,” Greenberg said. “We are productivity-obsessed in the worst possible way.”
“We are productivity-obsessed in the worst possible way.”
Greenberg has never worked a traditional nine-to-five, but he’s now on the hunt for a more stable gig as he continues to run his side hustles. Specifically, he wants his baseline income to be handled by a job that takes “between 25 to 40 hours a week.”
In his own Twitter thread, Greenberg called entrepreneurship lonely and hard. He loved being able to work everywhere, but didn’t like not having a team of peers. He loved having control over the budget and hiring, but not that he had to often pay for mentorship opportunities. “Don’t let the entrepreneurship, startup, hustle porn fool you,” Greenberg tweeted. “The only right choice is the one you choose to make.”
After all, working a nine-to-five has its perks and practicalities. Masaya, the UK native who tweeted about the pressure of entrepreneurship, said paid sick leave and maternity leave were two major benefits to working a traditional job. Noble, who gave up her own consulting business for a nine-to-five, liked knowing that there would be money for the bills each month.
In the United States, healthcare benefits – as well as dental, vision, and retirement – are tied to employment. In 2011, the Employee Benefit Research Institute found that there were over 20 million self-employed people in the US, 30% of whom lacked health insurance. And a study published in November of last year, by Agnieszka Kwapisz of Montana State University, found self-employed men were 62% less likely to be insured, and self-employed women 83% less likely, compared to the general public.
Paid sick leave and disability benefits are also tied to employment. Even to qualify for unemployment benefits – as over 50 million Americans did during the height of the pandemic last year – one must prove they had been employed recently.
“There are certain companies out there that do care about their employees and have amazing benefits,” said Heaven Williams, who works for a Sacramento homeless shelter during the day and runs a candle business on the side. “If you find something that you love to do and it’s a nine-to-five, there is nothing wrong with it.”
The structure of day jobs can learn a thing or two from entrepreneurship
One main part of entrepreneurship that most people like is flexibility and having agency over their time. Over 40% of those surveyed in 2017 for a report done by the accounting organization FreshBooks said becoming self-employed had given them better working hours, improved the quality of their childcare, and allowed them to spend more time with their families.
This is a trend that is looking more likely to be adopted into the traditional working environment, especially in a post-pandemic world. Insider’s reporting on the future of work has suggested the nine-to-five may not be the same after the crisis passes. Ashley Whillans, a professor at Harvard Business School, believed the traditional workweek could become more flexible, where workers come to the office three days a week, spend two days at home, and have two days off.
Microsoft is now allowing employees to work from home for less than 50% of their workweek. Both Twitter and Spotify are allowing employees to work from anywhere.
What’s more, Greenberg believed most people don’t even want to be entrepreneurs – they just hate the jobs they’re in. Matching workers with jobs they like could see an increase in employee satisfaction.
Joe Sanok, a podcast host and the author of the professional help book “Thursday Is the New Friday,” said he was a supporter of the four-day workweek, and that the concept of “summer Fridays” – the practice of giving employees part or full time off to enjoy the warmer months – should be more prevalent in modern workplaces.
Meanwhile, Paula Davis, a burnout consultant, said workplaces will be able to attract more people by offering more flexibility, such as the option for remote work and giving employees more free time.
“I also think a sense of meaning, impact, and purpose is something companies are really going to have to step their game up,” said Davis, who experienced burnout both as an entrepreneur and as a commercial lawyer. “You’re going to have to explain to people how this is changing the greater good.”
Even if the workweek is redefined and social media gets the story straight on entrepreneurship, society is still playing a dangerous game with productivity as more people seek to monetize their time and personas.
Burnout is at an all-time high, along with the number of side hustles. said she knew of many people who had started to work traditional jobs alongside side hustles, seeking to juggle both on their quests for uncertain success.
“That’s not productivity,” she said. “More, exhaustion.”
Payal Kadakia launched ClassPass in 2013 as a service to search for fitness options. Today, it’s an international membership booking platform for classes and services, from Pilates to haircuts to, recently, Covid-19 vaccinations – and is valued at $1 billion. Prior to founding her company, Kadakia was a Bain & Company analyst with a passion for Indian folk dance, which she began practicing at age 3. Her parents immigrated in the late 1970s from Gujarat, India, raising her in a rich culture – though she felt ostracized from her broader community at times. The duality she cultivated and later broke away from shaped her entrepreneurial journey.
– As told to Christine Lagorio-Chafkin
I grew up in Randolph, New Jersey, where I was one of the only Indian girls. We were one of the only Indian families. People didn’t understand who I was, or where I came from. I definitely got made fun of. People didn’t want to be around the person who was different. When you’re a kid, that makes a very big impression on you.
I had been bullied for so long I tried to hide my cultural heritage.
For example, I was a cheerleader. And I would have Friday night football games. There was a huge Indian festival called Navratri, which is my favorite festival of the year. The whole next town nearby would get together. And we would dance until two or three in the morning. I literally rushed from the football game and changed in my car into full-on Indian garb to go to the festival. This was the duality I lived with.
In a town down the road, there was another Indian community. There, I started doing Indian folk dance, and I found a group of people who were like me. I found a place in this community where I could connect with people because they looked like me and understood me. My cultural heritage had been so positive at home. Seeing how my mom and dad lived their lives, being in a country where they didn’t always understand everything, had been inspirational. My mom never took the idea that she couldn’t do something just because she didn’t understand it. She worked the night shift, and my dad worked during the day, because they couldn’t afford childcare. There was never a dead end.
When I went to college, a beautiful thing happened where I started really feeling OK in both skins.
I began seeing other people who were Indian – who kind of fit in. Dance was a huge part of it for me. It allowed me to care about who I was even more. I stopped feeling like I was different and started owning who I was.
I started a dance company called Sa Dance. I was inspired by watching Alvin Ailey, one of the greatest African-American dance companies in the world. I saw that the messages of your people can be represented through dance. Art is such a beautiful way of sharing messages of culture. Let me show you the beauty of it, the richness of it, how ancient it is, who my ancestors are. I started feeling like I was creating and leading and communicating about my culture. Dance became a vehicle for my coping.
When I started working on ClassPass, simply by building a company in fitness, I was in a roomful of men, most of the time.
Investors didn’t really know what I was talking about. I was just so unique in so many of the rooms I was in. But I’m also 4-foot-11. I’m a very petite Indian woman. I didn’t look like anyone I was ever in a room with. It took me three years to get my product right. When it worked, all of these investors and individuals who I had talked to in the previous three years were all of a sudden saying, “Hey, let me give you money!” And I’m thinking, “Why didn’t you bet on me before?” That’s the conversation that I sometimes have with myself about it: I didn’t fit their mold.
One of the biggest reasons I became an entrepreneur is I felt like I never fit into those environments – even my job in corporate America. Part of it was my cultural background, part was because of my artistic background. I needed to create an environment where I knew I could be like all colors of who I am. We obviously see this problem in the female-male dynamic that’s happening right now where capital is being deployed. But it’s the same thing when it comes to messages of culture.
I remember needing to hide. I remember needing to hide dance, being scared of sharing that part of myself with people. I realized over time that it has made me only stronger in everything I do. But other people need to have that ability to be their whole selves as well. In the press, people who look like me are not always represented. I didn’t see Indian people on the cover of magazines or on billboards. This is America, you know what I mean? We are a part of the population! And I think we’re really proud of who we are, and we’ve accomplished a lot. I want people to know that.
Many entrepreneurs are using newfound time at home to finally write down their unique ideas and stories to be published in book form. The Internet is rife with contradicting information about self-publishing and traditional book publishing, so which path should an entrepreneur – or writer in general – use for book publication?
As the owner and founder of MindStir Media, I’m confident in saying that self-publishing is the proper route in many cases. Here are three main reasons why:
1.You’re guaranteed to get your book published
With traditional publishing, you’ll generally need to find a literary agent to represent you and your work. But finding agent representation can be a long and arduous journey. I know writers who’ve spent upwards of a year or two sending out query letters and still haven’t been able to land an agent. Most traditional publishers will only look at a manuscript if it comes in through an agent, so literary agents are a valuable resource and contact when going the traditional publishing route.
The major problem with this approach is that nothing is guaranteed. You could be one of those people who spend years trying to find an agent, or you could land an agent, only to get rejected by the traditional publishers anyways.
With self-publishing, the ball is in your court. There are no literary gatekeepers holding you back. The consumer will be the final judge of your book.
2. You’ll keep control over your book
Writers don’t always consider the topic of rights when comparing self-publishing and traditional publishing. With a traditional publisher, it’s common for you to relinquish your publishing rights to that company, meaning that you’ll lose control over your publishing rights as well as any creative control. If you get to the point where an agent pitches your book to a publisher and said publisher accepts your manuscript for publication, the publisher will own the rights to your book and will ultimately have final say over the content of your published book.
Self-publishing is the complete opposite in every way. The self-publishing author keeps their publishing rights and all creative control, from the cover design to the editing and book production. In fact, you can research and select your own book designer, professional editor, printer, distributor, and more.
3. You’ll enjoy much higher royalty rates
It’s a bit of a dirty little secret in the publishing industry that traditional book deals only payout about 10% – 15% royalties to authors. Some traditional publishing advocates tend to argue that it’s worth giving up 85% to 90% royalties in exchange for superior support and distribution. But with physical bookshelf space dwindling and most consumers buying books through Amazon and other online retailers, that argument doesn’t hold much water in 2021.
An author can simply self-publish online and reach a large network of online retailers through a distributor such as Ingram. In turn, the self-published author can keep 70% t0 100% royalties. If your book sells 10,000 copies, for example, you could see tens of thousands of dollars in your bank account from those sales through self-publishing, whereas traditional publishing royalties might only reach $10,000 or less from those same 10,000 copies sold.
Entrepreneurship is challenging. Some days, it’s downright exhausting. For many entrepreneurs, there comes a “last straw” breaking point where the conditions are too stressful or too overwhelming to continue.
But for most others, the eventual loss of passion for entrepreneurship – better known as burnout – is something slower and more gradual. It’s a creeping feeling that grows from day to day and eventually begins to affect your work performance.
You won’t go from happy-go-lucky to ready to quit overnight. One day, you might be a little extra irritable. The next, you might wake up and dread the idea of going to work. Not long after, you might make worse decisions, rushing through projects, or you might seriously contemplate leaving.
It’s not a position any entrepreneur wants to find themselves in. The good news is, it’s mostly preventable.
Why it’s important to stop burnout
There’s nothing wrong with changing jobs, selling your business, or retiring. But burnout itself can be devastating. Not only will it force you to leave your business prematurely, it can also leave you feeling despair and exhaustion. Even more importantly, it can negatively affect you on a physical level; burnout is associated with higher stress, higher susceptibility to illness, and even a higher risk of heart disease.
These effects compound with time, so acknowledging and stopping burnout early can put you in a much more favorable position long-term.
The trouble is, burnout is difficult to catch, especially early on.
How to identify entrepreneurial burnout
We all feel stress. We all get nervous. We all experience anxiety or dread sometimes. So how do you know when this is just part of the job and when it’s an early sign of burnout?
You dread going to work consistently. One of the hallmark signs is dreading going to work. Everyone dreads going to work some of the time; there might be an awful client to deal with or negative consequences from a bad decision to manage. But if you dread going to work on a consistent basis, it’s a sign of developing burnout.
Your mood and personality have changed (according to others). It’s hard to notice the changes in your own personality since they often unfold gradually and beneath our notice. However, burnout often leads people to experience mood and personality changes. Talk to the people around you; do they notice that you’re more irritable, angrier, or less pleasant than you used to be? Chances are, something external is responsible for this.
You’re experiencing physical symptoms. As burnout develops, it tends to be associated with more and more physical symptoms. For example, you might feel more stress headaches. You might have trouble getting to sleep (or getting enough sleep). And you might even be more susceptible to contagious illnesses. Keep an eye out for these developments.
You always feel tired. No matter how much sleep you get, burnout will leave you feeling tired. You’ll be physically and mentally exhausted most of the time, even after a good night of sleep or a break away from work. It’s almost impossible to feel full of energy.
Solving the burnout problem
It’s tough to make a one-size-fits-all recommendation for how to get rid of burnout because there are many different types of professionals and many different types of burnout.
For example, your burnout might stem from your own over-investment, in which case, delegating more and reducing your workload could help. You might also be worn out from a specific type of stress, which might require you to change up your daily responsibilities. You might even feel under challenged due to excessive predictability and routine, in which case the solution is finding new ways to be stimulated, like learning a new skill.
In any case, one of the best steps to take to address your burnout is to take some time away. Use up a few vacation days or take an extended hiatus from your work; it’s a great opportunity to de-stress and get away from the burden of work. It’s also a chance to get some perspective. Once you’re away from the office, you’ll have a much keener sense of what’s actually stressing you out (and what you might be able to do about it).
You can also talk to the people around you for advice. They may have a better perspective on your work style than you do. Once you have a better understanding of your current position, you can invest time and energy into making an action plan. How can you change your environment and your approach to work in a way that relieves your stress?
The action plan will look different for everyone. But as long as you’re consistent and proactive, you’ll have a good chance of reversing the effects of entrepreneurial burnout in your career.