Articles on this Page
- 09/18/18--10:58: _I'm an ER doctor wh...
- 09/19/18--08:40: _A Morgan Stanley ex...
- 10/06/18--07:00: _Tech's diversity pr...
- 10/09/18--08:01: _I turned the 3-step...
- 10/11/18--07:10: _The former Google e...
- 10/11/18--11:07: _I've taught more th...
- 10/20/18--08:30: _This Irish CEO expl...
- 10/29/18--06:03: _An entrepreneur who...
- 11/02/18--07:48: _The CEO of a startu...
- 11/07/18--09:14: _A startup founder a...
- 11/08/18--08:56: _The best lesson I'v...
- 11/27/18--08:34: _A business school p...
- 12/01/18--00:00: _Former Google CEO E...
- 12/04/18--19:05: _IEX CEO Brad Katsuy...
- 12/07/18--11:49: _Barbara Corcoran on...
- 12/13/18--06:09: _I started my own bu...
- 12/21/18--06:01: _The 2 traits that h...
- 12/21/18--08:30: _When I decided to c...
- 12/31/18--08:49: _I built my own busi...
- 01/02/19--06:02: _I built a 6-figure ...
- Dr. Sudip Bose is an emergency physician and Cofounder and Chief Medical Officer at liveClinic.
- He's found that many health problems aren't unpredictable — if you track your health data, you'll see warning signs well in advance.
- The same applies to business: Tracking your data can help you spot problems before they become serious.
- He says that to improve any element of life — from health to business — you have to focus on the quantitative, not just the qualitative.
- Carla Harris is a Vice Chairman, Managing Director and Senior Client Advisor at Morgan Stanley.
- She heads Morgan Stanley's Multicultural Innovation Lab, which invests in multicultural and female tech entrepreneurs who have traditionally faced institutional and cultural barriers to funding.
- She considers these investments to be a business opportunity borne of a market inefficiency: underinvestment in female and multicultural tech entrepreneurs.
- This post is part of Business Insider's ongoing series on Better Capitalism.
- Silicon Valley has long had a diversity problem.
- Women, African-Americans, and Latinos are underrepresented in the tech industry and tend to be paid less than their white male counterparts.
- But the diversity problem is even worse than that; a new study found that the gender disparity in equity — or stock ownership — held by tech workers and founders is even worse than the pay gap.
- In Silicon Valley, stock holdings can be much more important and valuable than salaries.
- The disparity is important, because Silicon Valley's ecosystem centers around startup founders who cash in their shares when their companies go public or are acquired.
- Dr. Sudip Bose is an emergency physician and Cofounder and Chief Medical Officer at liveClinic.
- When he was being trained as a doctor, he was taught to check three things on any patient first, regardless of their complaint: airway, breathing, and circulation.
- As the CEO of his own startup, he translated this process into his own version of ABC: assess, break it down, and complete.
- He finds this system helps him prioritize problems without being distracted by anxiety or other emotional reactions.
- Beeswax is an ad-tech startup in New York founded by three former Google executives.
- The founders of Beeswax said they chose their company's name so it would stand out in a crowded industry.
- They deliberately avoided using the word "ad" in their name to distinguish them from their competition.
- Susie Moore is a high-performance coach, consultant, and author who has helped more than 500 people develop and grow side-hustles.
- She's found that she sees some commonalities among the people who can successfully transition their side hustle into a full-time career.
- Among those common traits are the determination to execute, the willingness to be decisive, and comfort being seen and building an audience.
- Eoghan McCabe is the CEO and cofounder of Intercom, one of the fastest growing startups in Silicon Valley.
- Intercom offers services that help companies communicate with their customers.
- McCabe and his partners formed Intercom after being inspired by the personalized service they got at a Dublin coffee shop.
- Intercom is now offering chatbots that can handle customer service.
- One of the best pieces of entrepreneurship advice has to do with hiring top talent.
- Instead of looking for people who can do the job today, look for people who will still be successful two or three years from now.
- That's according to Cesar Carvalho, the cofounder and CEO of corporate fitness program Gympass.
- When he first started Gympass, he hired people with the skills for a small startup, rather than for the large company it became.
- Hinge founder and CEO Justin McLeod tells new entrepreneurs to be both naive and flexible.
- It's important to stay true to your vision, while also taking into account criticisms of your business and changes in the market.
- McLeod learned this lesson firsthand: He believed in Hinge when no one else did, but he also had to make significant changes to the product years later.
- First-time CEO Daniela Corrente said hiring a business coach was the smartest move she's made since founding the personal-finance app Reel.
- Business coaches help executives grow their companies and clarify their visions.
- They're part of a growing industry, but Corrente said hiring one can carry a stigma.
- Taking on too many tasks can drain your energy and negatively impact your career.
- Here, author Charyn Pfeuffer describes how learning to set boundaries in her work and life allowed her to be happier and more successful.
- Most of us try to avoid tough conversations, but the most successful people tackle awkward subjects head on.
- A professor who studied 20,000 startup founders said "going ugly" and addressing uncomfortable issues can help you both in the business world and in romantic relationships.
- From planning for the departure of a company's cofounder to drawing up a prenuptial agreement, "going ugly" tends to benefit all parties in the long run.
- Eric Schmidt, the former CEO of Google, gave the Centre for Entrepreneurs lecture in London this week.
- In a draft of the speech, seen by Business Insider, Schmidt outlined what he sees as the three big market failures holding back tech entrepreneurship today.
- He said tech startups need to be more diverse, less product driven, and more willing to partner early.
- Brad Katsuyama, CEO of IEX and the star of Michael Lewis book "Flash Boys," spoke on Tuesday at Business Insider's IGNITION 2018 conference.
- Katsuyama said successful entrepreneurship means having experienced the problems you're trying to solve.
- He was a trader for years and felt there was a need for an alternative exchange that would prevent predatory trading.
- Katsuyama said, "In the lowest possible moments, where possibly you're even doubting yourself, you have to have a core belief that what you're trying to do is real."
- Ramit Sethi is an entrepreneur and CEO of I Will Teach You To Be Rich and GrowthLab,
- After 15 years building his businesses, he's narrowed down three pieces of entrepreneurship advice to share with people who ask.
- He wishes he had focused on getting paying clients sooner, on moving up the value chain, and being smarter about choosing his heroes.
- Demanding more from students of my courses; and the more I demanded of them, the more they achieved.
- Focusing on the QUALITY of my material. Some of the things that used to keep me up at night — like the visual look of my course — didn’t matter as much as I thought.
- Are they pushing you to be better?
- Are they pushing you to serve your customers?
- Do they have good ethics?
- In order to be wildly successful, you need to be optimistic and overconfident about your chances. But for the average person, being so out of touch with reality can lead to failure.
- That's according to Daniel Kahneman, a Nobel Prize-winning psychologist, who calls it a "paradox" of success.
- Still, in some cases, overconfidence can indeed help you, especially if you're a leader.
- While others were thinking about early retirement, I was thinking about a midlife career change.
- I committed myself to being a writer, even though I wasn't being paid to write.
- I had no choice but to make it work, and I drew on unused skills from my college background in acting to accomplish it.
- Maleeka T. Hollaway is a millennial entrepreneur who teaches small-business owners and entrepreneurs to position themselves to grow sustainable businesses and brands.
- When she started her own business, she knew she wanted to create multiple income streams — but she wasn't sure where to start.
- So she began doing just about everything that came her way, until she realized there was a common thread through all of her business offerings: communication.
- Below, she explains how she built her own streams of income and where she recommends other small-business owners start.
- Jenny Shih is a business coach who has taught more than 25,000 women how to earn a full-time income working 30 hours per week or less as online, service-based entrepreneurs.
- She built her own six-figure business working no more than 30 hours a week.
- She says being an entrepreneur without being a workaholic comes down to getting clear on your values, and setting boundaries.
As an emergency physician working the night shift, I see people with all sorts of health crises.
Gunshot wounds. Broken bones. Severe bleeding. Heart attacks. Strokes. Overdoses. Extreme fevers.
Every night when I walk into the hospital, the waiting room is overcrowded and the hallways are lined with patients. They have one thing in common: None expected to be in the ER today.
Most of the patients began the day like any other. They went to work or school, spent time with family, picked up some groceries. Then, suddenly, a sudden health crisis or a horrible accident hit them from nowhere.
Some might see this as an inevitable part of the human condition. But apart from the random accidents and awful acts of violence, I believe the vast majority of those visits could have been prevented.
Most health crises are not sudden — rather, they are the culmination of a slowly deteriorating health condition. If the patients had monitored their health and taken the proper steps to address their issues, they wouldn’t be in the ER tonight.
For example, nearly one in three people have high blood pressure. The vast majority display no symptoms and are unaware of their condition — until they are suddenly hit by a heart attack or stroke.
The principle is simple: The qualitative sense of “feeling good” is no substitute for obtaining quantitative information on your underlying health and working with a doctor to determine if you’re at risk for a major health issue.
Tracking your physical health isn’t all that different from tracking your business’ health
As an entrepreneur, I take the exactly same approach to running my company, liveClinic. I want data on virtually every measure of financial and operational performance so that I can recognize emerging issues and deal with them in a proactive manner before significant problems develop.
It was analytics drawn from my medical experience that was the inspiration for forming liveClinic in the first place. On a typical ER shift, I noticed that only about 10% of patients could tell me their medical history and the medications they’re taking. We researched over 100 clinics in the US and found similar results. It’s a problem for both patients and their health care providers: people simply do not recall their medical histories and their current medications — nor do they have an efficient way to access the information.
Now, marketing insights derived through various initiatives help us understand our users better. We work to check what our users like about the benefits and functionalities of our application. We conduct qualitative interviews that later help us delve into quantitative information on the values we create for our users to drive business actions.
We frequently use A/B testing, which allows us to assess two similar, but slightly different website features, to determine the best approach to engaging our users.
For example, we initially had direct links for user signup from our website. After qualitative interviews we wanted to experiment with embedding direct signup ability for our users right from the website. We started seeing 20% jump in signups after making that change.
By analyzing user behavior on our website, we discovered people were unlikely to take the trouble of uploading their medical records unless they had a compelling reason to do so. To solve that problem, we developed a system that enabled people to earn and redeem points for rewards, much like airline or credit card rewards, based on their health. As a result, engagement on our site increased dramatically.
I fervently believe that in order to improve any element of life — from health to business — you have to focus on the quantitative, not just the qualitative.
You can’t improve what you don’t measure.
Collect data. Compare. Pivot. Remeasure. Pivot again if needed. It may save your business — or your life.
As I like to say, where there’s a market inefficiency, there’s a commercial opportunity.
We know that only a tiny fraction of venture capital investment flows to women and people of color. Whether because of lack of experience with this demographic, or lack of imagination or understanding, the consequences have had profound societal ramifications. From a financial perspective, underinvestment in female and multicultural tech entrepreneurs represents a market inefficiency.
Because they were overlooked for so long, companies founded by women and people of color represent one of the biggest investment opportunities of our time. They are coming up with ideas that “traditional” founders don’t see, reaching untapped, growing markets, and generating real returns for investors who recognize what they have to offer.
That’s why nine tech entrepreneurs join me every day at Morgan Stanley’s Multicultural Innovation Lab. The Lab is one of the programs we started to change the investment landscape for entrepreneurs who struggle to overcome the institutional and cultural barriers to funding that so many multicultural and female founders face.
This isn’t just something we thought would be nice to do. Morgan Stanley looks to generate returns, and based on our professional market analysis, we feel it is incumbent on us, not as social scientists but as investment advisors, to bring these opportunities to the markets, to our clients.
That’s what’s on my mind when I’m sitting across the table from one of our entrepreneurs like Louise Broni-Mensah, who built Shoobs, a platform for urban nightlife, culture, and entertainment in her native England when she saw there was nothing like it, despite clear demand. When she tried to find investors, however, most of the, well, men, that she spoke to couldn’t imagine or connect with the idea and the market. It took off nonetheless, entirely due to her hard work, and we’re helping her bring Shoobs to the next level. I’m proud to say she’ll soon launch in the United States this fall, in none other than New York City.
Then there’s Tanya Van Court, who earned not one, but two engineering degrees from Stanford before establishing herself as a force in corporate marketing. She saw a gap in the market for services that teach financial literacy and strategies for goal-based savings to children that would stay with them as they grew into adults, so she built Goalsetter. She knew that both low-income and wealthy families could leverage the practice, the former to nurture ambition and financial wherewithal, and the latter to encourage responsible stewardship of family funds. And she persevered when potential investors shrugged, unable to fathom why anyone would need such a service.
Louise and Tanya are part of the second cohort of our Innovation Lab, two of nine companies chosen from more than 300 applications. Morgan Stanley understood their visions, and was willing to bet that if we provided capital and helped them build the kinds of networks many other entrepreneurs have, they could be something special.
The companies in our Lab all struggled to get funding, even when they participated in incubators that routinely connected their counterparts with millions. We provide $200,000, office space, a tailored curriculum, and mentorship from some of our most experienced people — in addition to access to our global network of investors.
Support goes all the way to the top, too. After a chance meeting in the elevator, Param Jaggi, whose company, Hatch Apps, enables businesses to build apps without any coding, emailed our Chairman and CEO James Gorman asking for a meeting. James told him — and the rest of the group — to come on up to his office.
And guess what? These folks are making great progress, and the companies from our first cohort continue to grow as well. One was already acquired. Another has acquisition offers on the table. Another launched a seed round that was oversubscribed and moved up its planning for a Series A.
That’s the kind of promise I see in Rhoden Monrose, whose company, CariClub, helps businesses connect young staff with associate board opportunities at non-profits. Rhoden was raised by a single mother in East Harlem who got help from several non-profits to get him and his sister the best education possible. He got a job at an investment bank after college, and wanted to give back, but didn’t know where to start. From this discovered gap between the desire to give back and the opportunity to do so, he created CariClub.
His clients are corporations that recognize his product as a great tool for cultivating employee engagement, enabling professional development, and demonstrating their own values. He’s in good shape now, but for two “brutal” years, he struggled to convince investors, most of whom were essentially born into networks where these opportunities are plentiful and just didn’t see the market. Morgan Stanley did, and we’re now one of his clients.
At the end of each day, I know that we have invested our time, and our capital, in a way that will be game changing for these companies and for us.
Carla Harris is a Vice Chairman, Managing Director and Senior Client Advisor at Morgan Stanley. She is responsible for increasing client connectivity and penetration to enhance revenue generation across the firm.Learn more about the Multicultural Innovation Lab at Morgan Stanley »
It's no surprise that the tech industry has a diversity problem.
But it turns out that the problem is much bigger than people in Silicon Valley and beyond may have realized.
It's well known that women, blacks, and Latinos are underrepresented in tech companies, particularly in the upper ranks. It's also well known that they tend to get paid less in salary for the same jobs than their white male counterparts. But the tech industry has a far larger divide that's been mostly kept secret until now, having to do with the ownership of companies.
Much of the payoff that tech workers get from working in the industry comes in the form of ownership stakes in their companies, whether in the form of founders' shares or stock options or restricted stock. It turns out that distribution of those shares is even more titled in favor of men than pay or representation within companies, a recent study from Carta found. And the underlying value of the shares is even more weighted in favor of men.
Women hold just 9% of the wealth linked to shares in tech startups
Carta offers an online service that helps companies manage their employee-owned shares and options. For its study, it looked at the private, venture-backed companies in its database. It didn't have direct information on employees' gender, but inferred it from their names, excluding those that were ambiguous. By definition, all the people included in the study held some sort of ownership stake in their companies; employees that don't have options or shares in their companies aren't in Carta's database.
Women comprised 33% of the people in the study; in other words, they made up about a third of all employee shareholders. But their shares were worth just 9% of the total value held by all employee owners in the study. Of the $42.6 billion held by the startup founders or workers included in Carta's study, just $4 billion was held by women.
Much of that imbalance is due to the paucity of venture-backed female founders and the value of the firms they lead. Women represent just 13% of all the founders in Carta's database. And their share of the total value of founder-held shares is only 6%.
"There's just a disproportionately low amount of capital going to back women," said Jana Messerschmidt, another member of the #Angels group.
Women do better as employees than as founders, but they still are getting a raw deal when it comes to equity stakes in their companies. Some 35% of non-founder employees in Carta's database are women. But their shares are worth just 20% of the total value held by such employees.
Put another way, women tech workers hold about 47 cents worth of equity for every dollar held by their male counterparts.
Startups don't tend to bring on women until later
Women lag behind men in part because they tend to be a small minority of the early employees at tech companies. At firms with 20 or fewer equity-holding employees, just 29% are women, on average. Even at companies with 101 to 400 equity employees, women make up just 35% to 36% of those workers. It's not until firms get to more than 400 workers that their portion of employee-owners who are women goes north of 40%.
By comparison, women comprise some 47% of workers in the total private US workforce.
Their low representation at early-stage startups is important. Early workers tend to get more valuable share grants than later workers, in part because they get in on the ground floor, when the company is usually worth very little.
Additionally, a disproportionate portion of the early hires at startups are engineers or developers, workers who are typically seen as vital to the startups' success and often paid accordingly. Women tend to be dramatically underrepresented in such positions.
Startups generally wait until later in their development to fill out the departments where women are more prominent, such as marketing, human resources, and sales — and they tend to award them with fewer and less valuable shares.
"The amount of equity that's given to employees decays over time," said Henry Ward, Carta's CEO.
The study had some notable shortcomings. Carta's database doesn't actually include equity holders' gender. The company inferred gender from the holders' names, excluding those from its study that were ambiguous. So the equity disparity could be somewhat bigger or smaller than what Carta found.
Additionally, the database doesn't include any data about holders' race or ethnicity. So, Carta wasn't able to look at the equity differences among different groups. Those too are likely to be significant. African-Americans and Latinos have long been grossly underrepresented in the tech industry. And a recent study indicates that members of those groups tend to be in lower-paying positions on average than their white counterparts and, even accounting for that, tend to be paid less than whites in comparable positions.
This is more than just a problem for the 1%
To be sure, compared with other inequality problems the US faces, disparity in equity compensation and holdings may seem rather trivial. Many workers — particular those in lower-skilled jobs — don't get health care benefits or sick days, much less stock options.
Tech workers, meanwhile, are generally well compensated overall, regardless of how many options they get. And when you're talking about founders, you're often talking about people in the top 1% of income earners.
But the disparity does matter, at least in terms of its downstream consequences. Much of Silicon Valley's ecosystem is built around the equity held by successful startup founders. Those founders often take their payouts when their firms are acquired or go public and use them to create other firms or to fund other entrepreneurs through so-called angel investments.
Many also join venture capital firms, where they help determine which of the next generation of startups get funding, or sit on tech company boards, where they help shape the composition of executive teams. They also often use their startup payouts to set up foundations that give out money to their preferred charities.
Silicon Valley is a clubby place. Founders tend to hire people who look like them, went to college with them, or run in the same social circles. VCs tend to invest in companies with founders that either look like them or look like founders who succeeded in the past. In both cases, the people who get funding or top positions tend to be male and white or, to some extent, Asian.
And that's become something of a cycle. White male VCs fund startups run by white men who, when they cash out, become VCs who fund the next generation of white male entrepreneurs.
So the disparity in equity in Silicon Valley doesn't just affect who's seeing the big bucks when a company goes public, it also affects who gets funded the next time around, who gets hired, what products and services are developed, and what communities see investments.
"In Silicon Valley, money from a successful exit is about more than just wealth," said Sladden. "It's the power to shape and choose the products and institutions that shape Silicon Valley the for next generation."
When a patient arrives in the emergency room, I'm trained to check three things first: airway, breathing, and circulation. In the chaos of the emergency room, when patients are horribly injured and in great pain, it’s tempting to bypass the sequence and immediately treat the injury and pain.
That would be a mistake.
Early in my career, I examined a patient who fractured his ankle so badly that the bone was protruding from the skin. While my first instinct was to immediately address this hideously painful injury, I suppressed this surge of empathy and completed my assessment. I quickly discovered his lung had collapsed.
If I hadn’t followed the sequence and examined his entire body, the patient very likely would have died.
The lesson here: Address the quietly critical before you address the visibly urgent.
Unfortunately, your emotions are usually working against you. The amygdalae are two almond-sized lumps in your brain, one on each side. Their job is to connect a life experience to an emotion. When we encounter an intense situation, the amygdalae go into action and hijack the logical sections of our brains.
They’re responsible for panic. Intense anger. Paralyzing fear. These emotions are a natural part of life, but they are also the enemy of good decision-making and effective performance.
As an emergency room doctor and a soldier, I learned how to deal with my instinctive emotions and perform under pressure. Now that I run my own startup outside of the ER, I’ve found I must exercise the same type of self-control.
In place of the ER protocol of airway, breathing, and circulation, I utilize a process of assess, break it down, and complete to determine the right actions to take in the face of a challenging business or personal situation.
For example, let’s say you’re running a startup business that’s struggling to find customers and is under intense scrutiny from investors who are threatening to sell their stakes if the financial performance doesn’t improve. That’s exactly what happened to me.
One morning, we found a pornography website had hacked our website. Now thousands of physicians seeking our teaching material were getting more than they wished for. Our IT team detected the threat early on and believed the threat could be isolated and contained without taking the entire system offline. As CEO, the obvious temptation was to instruct the team to quietly handle the situation to avoid any harm to our reputation. We had enough problems already.
Instead, we assessed the situation objectively and broke down the possible scenarios.
Using my framework of assess, break it down, and complete, we determined the greatest threat to the life of the business would be to remain silent in the face of possibility that the hacker stole our customer data — and then a customer discovers from another source that their data had been compromised. Our reputation among all our customers would be irreparably harmed and we would be subject to legal action. Our fledgling business could easily be destroyed.
The proper decision: Notify all customers, investors, and law enforcement agencies of the security hack and explain everything we’re doing to contain the damage and set up new protocols to better safeguard our systems.
Sure, it wasn’t pleasant. But by not allowing my amygdalae to hijack my logic, we made the right decision and took the right actions. Sticking with a disciplined process in tough situations helps enormously.
We can’t make panic, fear, and anger disappear from our lives. What we can do is create processes and routines that help us to perform at our best and avoid impulsive actions that may harm ourselves and others.
It works in the ER. It can work in business, too.
One of the most important factors to weigh when choosing the name of a company is how memorable it will be to your customers.
The founders of Beeswax kept that in mind.
Beeswax is a New York ad-tech startup founded by three former Google ad executives. The company pioneered a new way for marketers to bid for ads online. Three years after the startup's launch, its revenue was estimated at $25 million.
So what does beeswax have to do with advertising?
"I really liked the insect metaphors because our customers are very hardworking and industrious, and they're toiling away doing their thing," CEO Ari Paparo told Business Insider. "So we were thinking about hives and ants and bees and it just evolved."
The metaphor doesn't stop there. The names of Beeswax's products are on-brand references like Buzz, Drone, Stinger, Pollinator, and Waggle, the name of a dance bees use to communicate. The walls of Beeswax's Manhattan office are painted with hexagonal, honeycomb-like designs.
"We're doing something really different, we're doing something pretty bold. We want it to be memorable," chief product officer Shamim Samadi told Business Insider.
For the founders, choosing a unique name for their startup was also a way to distinguish them from their competition. In New York City alone, the crowded ad-tech industry includes companies with names like AdRoll, AdHawk, ADstruc, adMarketplace, and xAd, and Paparo said "it was the No. 1 requirement" that their name didn't have "ad" in it.
"Ad tech's been around for a while, and we're coming into the market later than our competition. So we felt like we just had to break through," Paparo said. "If we had another name like AdPotato, everyone would be like, ah, that sounds like those other guys, 'ad' this, 'ad' that."
"So definitely it was a conscious decision to try to do something that would leverage up our awareness and our marketing."
Samadi put it more bluntly.
"No one's asked what our company name is twice," he said.
“Susie, I’m quitting my job this Friday — I can’t believe this day has come!”
This was the second message I got in two weeks from a Side Hustle Made Simple student of mine who had stepped out into being their own boss. It’s always celebratory news because transitioning out of a 9-5 is a goal for a lot of people. And starting a side hustle is their most practical, low-risk path to get there.
After coaching people from jewelry designers to aqua aerobics instructors on how to start and then skyrocket their side hustle, there are five key qualities I observe over and over again in those that take it all the way to full time entrepreneurship (like I did in 2014).
To be your own boss is something you have to really want. It can’t just be a nice idea or sort-of interesting to you. Running a business (even if it’s just one person — you!) has endless ups and downs, so the certainty that it’s the right choice for you matters.
When your clarity about being a CEO is firm, you are more in tune with your own intuition than anyone else’s opinion. This is important because most people are risk averse and prefer job misery to entrepreneurial uncertainty and are happy to convince you to keep your “safe” job. Your creativity fires up, too — when you go “all in,” money-making opportunities become more visible to you because they have to.
Almost every successful side hustler I’ve coached grows leaps and bounds every six months. This is because they constantly ask questions and learn new skills (from using Wordpress to copywriting to Facebook ad execution). Learning never ends.
But learning isn’t enough. Knowledge is only potential power so applying it is where the money-making magic happens. Execution is everything. Better 27 attempts at launching a product or service and one taking off than creating the perfect product that never ships.
The good and bad news about starting out is that there is no right way — or one way — to be successful. There are millions of ways to run a profitable side hustle that can replace and exceed your income.
This means you have to be decisive. You have to choose your product name, your product price, your sales strategy. You need to make a call on when to go to market, how to niche yourself, when to make your first hire.
Indecision will keep you at a standstill, and standing still has the same impact as falling behind.
In her best-selling book “Grit,” Angela Duckworth writes, “Grit has two components: passion and perseverance. This consistent pattern — perseverance scores more often topping passion scores — is a clue that passion and perseverance aren’t exactly the same thing.”
Put simply, passion isn’t enough. You need tenacity and perseverance, too. Being able to bounce back from failures and fostering a healthy growth mindset (“What can I learn from this? Onward!”) is critical. Sensitivity and dwelling on failure or criticism will sink you.
5. Comfort being seen
In order for people to buy your stuff, they have to know about you. This means the hustle applies to building an audience as much as it does build a product that delivers value. This is not easy for a lot of people, but those who push through it, win. It also gets easier with time and there are many methods even an introvert can master to get attention on their business. For example, getting free publicity has been a game-changer for my students and for me.
Instagram, SPANX, and Udemy were all side hustles once upon a time. Starting small doesn’t mean you don’t finish big. So, if you’re hungry for it, are willing to execute, make daily decisions, persevere through obstacles, and be seen by more and more people, your resignation letter may be closer than you think, too.
Susie Moore is a New York-based high-performance coach, consultant, and author of "What If It Does Work Out?: How a Side Hustle Can Change Your Life." She’s been featured on the Today show, Forbes, Oprah.com and more. If you’re curious about starting (or scaling) your side hustle, sign up for her free workshop here.
Eoghan McCabe, CEO and co-founder of Intercom, first came up with the idea for his business in a coffee shop.
In Dublin, where McCabe is from, he and his coworkers would frequent a hipster coffee shop called 3fe and chat with the owner, Colin Harmon. There weren’t many other coffee shops with that vibe in the city, and McCabe appreciated how Harmon connected with his customers. The personalized service Harmon offered ended up inspiring McCabe and his partners.
"We got to meet and appreciate the guy, feel the passion for his craft," McCabe said. "We built a relationship with him and paid more for his overpriced coffee."
He continued: "When we looked at every internet business, they didn’t get to connect with us the way Colin connected with us."
McCabe started thinking about how internet businesses aren't great at interacting with customers. Typically they send customers emails from "donotreply" addresses and then route them through not always helpful "help" desks when they need more support.
"All these products were really impersonal," McCabe said. "With Colin, if you went into his store and asked, 'We have a question about Colombian roast,' he’d say, 'What is it?'"
McCabe and co-founders Des Traynor, Ciaran Lee, and David Barrett, soon got to work on a messaging service for companies that became the foundation of Intercom.
Intercom has become a billion-dollar company and is growing fast
Fast forward seven years to today, and the company has become a $1.3 billion business headquartered in San Francisco with offices in four other cities. It's one of the fastest growing startups in Silicon Valley. In March, it raised $125 million in new funds. And just this month, it launched its new product, the Answer Bot.
When Intercom first began, it focused on creating an instant messaging system to connect companies' customers with their sales, marketing, and support employees. Its next step is to use machine learning and artificial intelligence to create bots that can offer customer support.
"The first chapter was about getting people back into the mix," McCabe said. "This next chapter is to facilitate automation, bots, to achieve the same vision and mission."
That may seem contradictory. After all, Intercom's original goal was to make businesses more personal, and bots are literally not persons at all.
But McCabe says the apparent contradiction goes away if you think about the meaning of "personal."
It's "all about treating the customer as an individual," he said. "It’s about respecting their time and their dignity. It's all about getting them to their ideal outcome.
"We started to realize these bots and automation technology could do all that — sometimes better than humans."
Intercom's bots are designed to help out human workers
Intercom's bots aren't pretending to be humans; they're open about being bots. They're also not intended to completely replace human workers. Instead, they're meant to assist them and allow companies to help more customers than they could before.
If a company only has human workers to handle customer service questions, customers can end up having to wait long periods for someone to handle their queries. Intercom's clients can use Answer Bot to handle some of those questions instead.
The service uses machine learning, relying on previous conversations between employees and customers to figure out how to answer new queries. Intercom clients can even build their own chatbots using Custom Bot, a product the company released in August.
While their bots are handling routine questions, companies can route more complicated ones to their human workers.
"Answer Bot has a deep bank of the questions people ask about that business," McCabe said. "The next time people ask that question, it doesn't get sent to your support team to answer that question for the 2000th damn time. Answer Bot can answer that and say, 'let us know if you need anything else.'"
McCabe predicts that bots will soon become commonplace. Intercom has over 30,000 paying customers, including Sotheby's, Atlassian, Shopify, and Expensify, and its service facilitates 500 million conversations a month. To improve its bot technology, the company is doubling down on research and development and expanding its product development team.
McCabe and his team learned from past mistakes
But leading a company hasn't always been easy, McCabe said. Intercom isn’t his first startup — he had previously founded two other ones with the company's other cofounders. Those experiences helped, since he and his partners made a lot of mistakes along the way in their prior ventures.
"A lot of the dumbest mistakes we got out of the way," he said.
McCabe and his cofounders learned that to be successful, they needed to figure out how to have their companies do what they're best at while continuing to innovate. Having learned that lesson, he’s ready to face the next chapter in automation. And he thinks his company is primed for a major transition in the industry.
"In the next couple of years, every single business that has invested in trying to accelerate their growth will have simple bots working alongside humans," he said. That will allow them "to have higher quality and faster response to allow humans to do what humans do best."
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When he launched Gympass in summer 2012, Cesar Carvalho never imagined that the company would one day scale to include 38,000 fitness facilities across the globe.
That was a problem.
Gympass is a corporate fitness program similar to ClassPass. Once a company signs up, its employees have access to a range of gyms in different locations, at a discounted rate. Current global clients include Uber, PayPal, and Deloitte.
When Carvalho, the company's cofounder and CEO, started building Gympass, he was a student at Harvard Business School; he dropped out soon after to work full-time on his business.
Carvalho told Business Insider that his inability to envision a bigger future for the company — which currently employs about 800 people worldwide — negatively influenced his hiring strategy. Specifically, he made the mistake of looking for people who could do the job that day, as opposed to people who would still excel in their role years into the future.
"The hiring decisions that we made in the beginning were not optimal," Carvalho said. "We had to continuously bring more senior people to the company. And what I learned from it is that being able to plan for the next two to three years helps a lot on that."
Today, he seeks candidates "who are going to be great [working on] not what has to be done today, but two to three years from now."
You probably won't regret over-investing in hiring top talent
Carvalho's observations about hiring recall those of Patty McCord, the former chief talent officer at Netflix. McCord previously told Business Insider that managers should always be considering whether the team they have now will still be able to push the company forward in six months. If not, the manager may need to replace some people on their team.
To be sure, a stellar candidate may not necessarily want to join your fledgling startup.
"It's actually super challenging to make the decision to hire someone for what the company needs three years from now," Carvalho said. "At the point in time that you're making the decision, you might not have at the bank the cash that you need to support that person."
That means "taking two leaps of faith on the future of the company," Carvalho said. Not only are you assuming that this person will still be a good fit in three years — you're also assuming that the business will still be successful in three years.
That said, Carvalho wishes he'd invested more in the people running his company from the outset: "Had we done it, we would have been at a much better stage today than we currently are."
When Justin McLeod was first pitching his idea for dating app Hinge, few people believed he'd be successful.
Instead, McLeod told Business Insider, they'd say to him, "This is never going to be a thing. Match.com owns the market. No one's ever going to be able to break into it."
This was more than seven years ago, back before dating apps had taken off (Tinder launched in 2012). But McLeod, Hinge's CEO, was relatively certain that the app — which initially matched users with people they were connected to through mutual Facebook friends — would be a hit.
Today, Hinge has raised more than $20 million, according to Crunchbase, and is one of the most popular dating apps in the US.
When McLeod advises early stage entrepreneurs, he mentions his own determination to make Hinge work, even in the face of resistance. But he also cautions those founders to listen to their critics and to be willing to change course if necessary.
As an entrepreneur, McLeod said, you must have "this naiveté and belief that you're going to make this succeed no matter what. But, on the other hand, if you hold too closely to your vision, and you're not flexible, and you're not willing to change it, and you're not willing to evolve over time, then you can just hold onto some vision that's not working."
McLeod knows firsthand about the importance of flexibility. In 2016, he made the decision to "reboot" Hinge, most notably removing the swiping feature so the app could appeal more to users interested in serious relationships.
This decision, McLeod said, was based partly on the publication of a Vanity Fair article about the dating "apocalypse," and partly on McLeod's observation that Hinge had become too similar to other dating apps on the market.
"If you always listen to everyone else, then you'll never do anything new," McLeod said. "And if you never listen to anyone else, then you'll get to the point where you might do something crazy, or you're just banging your head against the wall."
He added that at Hinge, "Doing things the same way we've always done as the company continues to grow and the market continues to change is just a recipe for disaster."
Running a business is harder than it looks, and it pays to have someone show you the ropes.
That's why Daniela Corrente, a first-time CEO who founded the personal-finance app Reel, said the smartest move she's made in her career so far is hiring a business coach.
Business coaches are personal mentors who help executives grow their business and clarify their vision for the company. They're part of a rapidly growing industry, but as Corrente puts it, hiring one still carries something of a stigma for early-stage companies.
"I know plenty of successful people that use a coach, they just don't necessarily admit it or say it out loud," she told Business Insider.
Corrente said she meets with her coach once a week to discuss everything from hiring strategy, fundraising, and establishing company values. The biggest help came with developing measurable benchmarks for her office of six employees, she said.
"Nobody tells you when you have an idea and you want to bring it to life that all of a sudden you have to become an accountant, HR, so many things in the beginning, especially as a first-time founder," she told Business Insider. "There are so many things you have to manage to keep the train running."
On top of that, her coach even recommended she start meditating, something she says has made her more patient and less stressed.
"A big part of being a good CEO is investing time developing your personal skills so you can evolve as your company evolves," she said. "The founder you are when you have one employee has to be fundamentally different to the founder you need to be when you have 50 employees."
Reel, founded in 2016, aims to help users afford big-ticket fashion items. Users select clothing and accessories they want and are prompted to link their bank account and allocate a certain amount of savings to the purchase each day or week. When they hit their target, they can buy the product.
Corrente knew she didn't have the business pedigree other company founders might, having studied industrial design and communications in school. That made hiring a coach an easy decision.
"Most companies fail not for lack of capital, but for lack of good leadership. So I’m highly invested in being the best leader I can be for my team and for the success of Reel," she said.
I've been freelancing for more than two decades. By most standards, I've had a successful career, with bylines in more than 100 publications, including Marie Claire, The Globe and Mail, and The Washington Post. Most years, I've cleared six figures, a feat considering the average national income for a freelance writer is $46,000. I love what I do for a living.
I'm a bit of a professional anomaly. I'm a college dropout who stumbled into a writing career. I didn't go to journalism school or have a mentor. I learned every single thing I know by making mistakes.
The biggest lesson I learned early on, though, was to be kind and empathetic but fiercely protect my boundaries. This strategy has paid dividends in my life, both personally and professionally.
A balancing act
As soon as I learned how to balance being an empathetic human being with my own sense of agency, I became far more successful in life, in general.
I'm a giver by nature (but most definitely not a people-pleaser). If I drop my walls and let you in, you're all in, and I'll go to the mat for you every time. I also try to spread kindness whenever possible, whether it's a smile, some kind words or an intentional act, like a handwritten note or impromptu bouquet of flowers.
I'm a natural born networker and I love connecting people. I believe if you're good and good at what you do, there's always enough to go around. I tirelessly try to build my friends and peers up. That kind of support is invaluable.
The not-so-great thing is I've learned is that people will take advantage of kindness. As a result, I've had to learn how to set hard and fast boundaries. I stopped saying "yes" to things I don't want to do, whether it's a work project or personal engagement. If something doesn't bring positivity into my life, I steer clear.
The benefits of boundaries
Some people interpret my boundaries as a way of keeping people out, but they make my life easier and free up the space to give more of myself to things that actually matter to me. I choose to invest my time in creating a happy and prosperous life and don't make room for people or projects that drain my energy.
You're never going to please anyone 100% of the time, and you should never apologize for putting yourself first, especially if it puts you in a better position to help others.
Establishing boundaries allows you to prioritize your well-being while creating the space to be kind and take care of others. I've found that striking this magic balance makes it so much easier to be positive and productive and live an unapologetically authentic and successful life.
It's human nature to want to avoid tough conversations.
But the most successful people know that skirting around uncomfortable subjects just makes things worse in the long run.
That's what Noam Wasserman, a professor of clinical entrepreneurship at the University of Southern California, discovered after almost 20 years of studying 20,000 startup founders.
Wasserman wrote about the lessons he learned from his research in The Wall Street Journal on Sunday, and he said they apply to both business and life itself.
The professor wrote that the best startup founders he studied had a tendency to approach tough discussions head on — "going ugly," as he calls it.
"In a hypercompetitive environment, there is little wiggle room for balky products or ineffective team members," Wasserman wrote for The Journal. "As a result, the best founders move quickly to identify and deal with any problem areas they see, despite the natural inclination to avoid tension-filled issues."
In one case he studied, two of the three cofounders of a software startup had doubts that the third founder would remain with the company. The third founder had just become a father, and they suspected he might take his ownership stake in the startup and leave for a more stable job, leaving the company unable to attract a good replacement.
To cover their bases, the founders "went ugly" and drafted a plan about what would happen in such a scenario.
"It was a tough conversation, but it paid off," Wasserman wrote. "When the new father decided that he couldn't found a venture while founding a family, the company had a deal ready to go. The co-founders reclaimed his ownership stake, used his shares to lure a replacement executive and, down the road, attracted a buyer."
But "going ugly" is more than just good business advice — it can help in personal relationships, too.
Wasserman said one of his students had a habit of "going ugly" on first dates, refusing to tiptoe around awkward topics like income prospects and where he wants to live.
Prenuptial agreements are another example of how "going ugly" can benefit both parties in a relationship.
"Just as in the entrepreneurial world, agreements like these can strengthen relationships by surfacing issues early, revealing people's true intentions and motivations and clarifying expectations while adjustments can still be made easily," Wasserman said.
Former Google CEO Eric Schmidt has listed the three "big failures" in tech entrepreneurship around the world.
Schmidt outlined the failings in a speech he gave at the Centre for Entrepreneurs in London this week. He later expanded on his thoughts in an interview with former BBC News boss James Harding.
Below are the three mistakes he outlined, with quotes taken from both a draft of his speech seen by Business Insider, and comments he delivered on the night.
1. People stick to who and what they know
"Far too often, we invest mostly in people we already know, who are working in very narrow disciplines," Schmidt wrote in his draft.
In his speech, Schmidt pegged this point closely to a need for diversity and inclusion. He said companies need to be open to bringing in people from other countries and backgrounds.
He said entrepreneurship won't flourish if people are "going to one institution, hiring only those people, and only — if I can be blunt — only white males."
During the Q&A, Schmidt specifically addressed the gender imbalance in the tech industry. He said there's a reason to be optimistic about women's representation in tech improving, predicting that tech's gender imbalance will vanish in one generation.
2. Too much focus on product and not on platforms
"We frequently don't build the best technology platforms to tackle big social challenges, because often there is no immediate promise of commercial return," Schmidt wrote in his draft.
"There are a million e-commerce apps but not enough speciality platforms for safely sharing and analyzing data on homelessness, climate change or refugees."
Schmidt's omitted this mention of socially conscious tech from his final speech, but did say that he sees a lot of innovation coming out of network platforms, which allow people to connect and pool data, because "the barrier to entry for these startups is very, very low."
3. Companies aren't partnering up early enough
Finally, Schmidt wrote in his draft that tech startups don't partner enough with other companies in the modern, hyper-connected world. "It's impossible to think about any major challenge for society in a silo," he wrote.
He said in his speech that tech firms have to be ready to partner "fairly early." He gave the example of a startup that wants to build homecare robots.
"The market for homecare robots is going to be very, very large. The problem is that you need visual systems, and machine learning systems, and listening systems, and motor systems, and so forth. You're not going to be able to do it with three people," he said.
After detailing his failures in tech entrepreneurship, Schmidt laid out what he views as the solution. He referred back to the Renaissance in Europe, saying people turned their hand to all sorts of disciplines, from science, to art, to business.
"No one tried to put Leonardo da Vinci in a silo," he said.
You can watch Schmidt's full lecture and Q&A here:
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Brad Katsuyama has one "critical" piece of advice for other entrepreneurs: "You have to have experienced the problems that you're trying to solve."
Katsuyama is the CEO of upstart stock exchange IEX, and is best known as the star of Michael Lewis' 2014 bestseller, "Flash Boys."
At Business Insider's IGNITION conference in New York Tuesday, Katsuyama said, "If you're doing something controversial, there's going to be a lot of people fighting against you. In the lowest possible moments, where possibly you're even doubting yourself, you have to have a core belief that what you're trying to do is real. It's a problem that needs to be solved."
Katsuyama added, "When your back's against the wall, you have to firmly believe that, or you're never going to make it through."
IEX was born out of Katsuyama's experience as a trader at Royal Bank of Canada: He founded the company in 2012 as a new exchange that would prevent the predatory trading that took place on traditional US exchanges.
In September 2018, IEX snagged its first listing from Nasdaq, Business Insider's Frank Chaparro reported.
"I lived the story," Katsuyama said of the "Flash Boys" plot. "Never for a second have I doubted what I lived through."
Katsuyama's memory of his experiences as a trader kept him going through the ups and downs of launching IEX.
Some other successful entrepreneurs have similar advice. Neil Blumenthal, CEO of Warby Parker said the best way to discover a solid business idea is to write down your frustrations every day.
Interestingly, Blumenthal also said that many entrepreneurs "needed to live a little and experience a little bit of life to identify where there are problems that need solving."
As for Katsuyama, he said, "At the end of the day, when no one believes in your idea, you have to be the one who believes in it."
At IGNITION 2018, Barbara Corcoran, founder of The Corcoran Group and investor on ABC's "Shark Tank," spoke with Insider US editor-in-chief, Julie Zeveloff West, about entrepreneurship. She explained the key to a good business partnership, why she fired 25% of her sales staff, and the roles gender and wealth play in career success.
I often get people in their 20s and 30s that ask how I would start entrepreneurship if I were to start from scratch again.
Looking back to my 15-plus years of starting and building businesses, I want to share with you three primary things that I would focus on.
The first thing I would do is focus on getting paying clients
All these young entrepreneurs get sucked into what I call “vanity metrics” — the number of followers or subscribers they have or how many likes they’ve gotten on a single picture of them doing a hand stand on a mountaintop during a sunset. But in the end, the best Instagram account with hundreds of thousands of followers or the coolest copy in the world matters far less than paying customers when you’re trying to grow a business.
Because those things — Instagram followers and likes — don’t necessarily mean you are providing value to your market.
The ultimate sign that you are providing value is when someone pulls out their credit card and pays you.
After all, you have to be really good at what you do for people to want to pay you and stick with you.
The second thing I would focus on is to move up the value chain
What I mean by that is, I see a lot of entrepreneurs stunt their growth because they sell products for $19 or charge $30 per hour. While that’s amazing in the beginning, eventually you want to keep moving up the value chain to flex your skills and set yourself apart. For example, I started out with an ebook that cost $4.95, which was a BIG DEAL to me at the time.
Gradually I moved myself up the value chain 100X with my Earn 1K course. I knew people were getting great results from my course five years after starting my site I Will Teach You To Be Rich. And I was able to do this by:
Of course, moving up the value chain is a slow, gradual, and imperfect process. It took me a lot of baby steps and mistakes.
The third suggestion I would give to beginning entrepreneurs is to choose your heroes carefully
There are internet marketers out there that seemingly brag about how much money they could extract, what type of weird “trip wire” tactic they did, or how they analyzed these shrouded “hacks” in the backend to make 19 cents more out of every transaction. I remember attending a conference where people introduced themselves by saying:
“Hi, I’m <insert name> and I make $400K a year and work only two days per week.”
Ick. I felt like I needed to take a shower afterward.
People bragging about how much money they make and how little they work are just not the type of people I want to surround myself with.
The heroes I celebrate are those who have built businesses that last, offer amazing value, and have good ethics — someone like Howard Schultz from Starbucks.
I would encourage you to think carefully about the type of people around you:
Be cognizant of the people you surround yourself with, because those values will rub off on you.
Ramit Sethi is the author of the New York Times bestseller, "I Will Teach You To Be Rich," and writes for more than 1 million readers on his websites, iwillteachyoutoberich.com and GrowthLab.com. His work on personal finance and entrepreneurship have been featured in The New York Times, Wall Street Journal, and Business Insider.
Since I heard Daniel Kahneman speak at the World Business Forum this year, I haven't stopped thinking about one particular point he raised.
Kahneman is a Nobel Prize-winning psychologist and the author of the 2011 bestseller "Thinking, Fast and Slow," in which he outlined a series of cognitive biases that affect our everyday decisions.
At WBF, Kahneman spoke about a "paradox" of success: You probably can't be wildly successful unless you're optimistic and overconfident about your chances. But generally speaking, optimism (the belief that you're less likely than others to experience bad events and more likely to experience positive events) and overconfidence (an inflated sense of accuracy or ability in a specific area) are career saboteurs.
It's the difference between, say, the Elon Musks and Jeff Bezoses of the world and the rest of us.
"To be optimistic on average — it's not favorable," Kahneman said. But "extreme success is impossible without optimism."
Kahneman pointed to a 2007 paper published in the Journal of Behavioral Decision Making.
Researchers looked at a group of inventors in Canada and found that above-average optimists who were advised not to pursue their project ended up spending 166% more money than below-average optimists did when they received the same advice. (The researchers found that overconfidence didn't have an effect on the inventors' spending behavior, but that may have been because they didn't specifically measure the inventors' confidence in their abilities.)
Based on their findings, the researchers surmise that "a high level of optimism may act to keep inventors going in the face of adversity"— which is either a laudable or completely impractical behavior depending on your perspective.
As Kahneman described it, the average inventor would have been better off financially heeding the negative advice and taking a more traditional job; but the most successful inventors would not have.
In some circumstances, overconfidence can be beneficial
A more recent study provides some preliminary evidence that, at least among entrepreneurs, optimism can backfire.
The study, which was published in the journal European Economic Review, found that above-average optimists who are self-employed earn 30% less than below-average optimists who are self-employed. Interestingly, however, the study also found that optimists who work for companies earn more than their more pessimistic peers.
Still, there are some circumstances in which overconfidence in particular can work to your benefit. An article in the Harvard Business Review describes a study that found, at firms led by overconfident CEOs, there tends to be lower employee turnover and employees allocate a greater share of the assets in their retirement benefit plans to company stock.
The authors write in The Harvard Business Review, "At least in the corporate world, there may be a bright side to overconfidence: it can increase the commitment of other people to your venture."
As for Kahneman, he called optimism the "engine of capitalism." He said, "When you have lots of people trying things against the odds, it's not very good for most of them. Most of them will fail. But it's very good for society at large to have a lot of people competing and a few of them succeed."
It's in their 50s that some people start to think about early retirement, but for me, it was when I decided to start a new career.
For over two decades, I worked as an account manager for the independent video store Vidiots, even though I had a degree in theater arts. I had taken the job as something temporary that I could do "until my acting career took off." But the problem was, deep down, I didn't see myself as an actress, and I did nothing to pursue it — I didn't go on auditions, I didn't participate in showcases, and I sent out zero resumes and headshots.
I may have called myself an actress, but the truth was, I was more of an accounts-receivable clerk than anything.
Since I was all talk, I ended up staying at my "just-for-now" job for 21 years. When I left that job, I knew that I didn't want to be an actress or work in retail any longer. Although I loved my time at Vidiots and the people I worked with, I knew that I was meant to do more.
Becoming a writer
I decided to become a freelance writer. I'd always loved storytelling, and writing was the perfect outlet for me to tell stories and get paid for doing so. I knew that I had to do things differently this time. I couldn't just pretend I was a writer; I had to take actual steps to make it happen.
The one thing I needed to do to make writing more than a dream was that I had to commit to being a writer 100%.
I was lucky because I did have a small safety net. I lived with my boyfriend, Andy who worked as an IT consultant. But he didn't make a ton of money, and because of the nature of the tech industry, his job wasn't always secure. So, the pressure was on me not to fail.
"Are you going to get a job?" Andy would ask.
"I have a job," I'd say. "I'm a writer." The more I audibly confirmed my writer status to him, the more I believed it myself.
Since sitting around and waiting to be discovered hadn't worked for my acting career, I knew that I needed to be proactive and so I put my belief that I was a writer into practice. I lived my life as I thought a professional writer would since that's what I believed I could be.
I got up every morning and got ready for work, the same way I would if I was going into an office. Once I was finished with my chores and morning rituals, I sat down at my desk — the dining room table — and started my day. I pledged to write at least five hours per session. I wrote about many different subjects: women's issues, relationships, mental health, and pets.
While the bulk of a writer's life is writing, writers have other tasks to do, too. I spent my days pitching publications with story ideas, writing articles on spec (writing a piece before actually having the job), being active on social media, and doing unpaid pieces for literary magazines.
'Acting as if'
When I was studying acting in school, we learned to"act as if"— meaning, if our character was a banker, then we acted like a banker and truly believed we were a banker. I used that technique in my real life and acted as if I was a writer.
I decided to do something every day that advanced my writing career, even if it was only having coffee with an established writer and asking for their advice. You've got to keep moving towards a goal — even if you're moving at a snail's pace.
Then, after five months of struggling, I got my first paid piece accepted by the now-defunct women's site, XoJane. The payment was only $50, but it felt like a huge amount of money to me — it was the first money I had ever made from writing. Then I got another piece on that site, and soon after, I had an essay published in The Los Angeles Times. There was no denying it: I was being paid to write.
The takeaway? Since labeling myself as a writer, I've had thousands of articles published on many different kinds of venues, from Women's Day to Salon, and I've gotten steady writing gigs that help provide the bulk of my income. I'm paying a larger portion of our household expenses than I used to, and while I'm not taking lavish vacations, I don't have to live as frugally as I did before.
I've learned that it's never too late to start a new career as long as you're passionate about it and can fully commit to it. And if you're anything like me, your second career may end up being much more fulfilling and creatively challenging than your first.
My office is still the dining room table, but now, people know not to ask, "When are you going to get a job?" Writing isn't my hobby — it's my job.
When I started my own business about four years ago, I had no clue what I really wanted to do.
I knew that I could not build a sustainable business doing one-off projects. I needed to diversify my offerings and extend my professional reach. I needed to be one of those people who made money in my sleep.
To be that person, I knew I needed multiple streams of income. For as long as I can remember, I've heard people say that the average millionaire has seven streams of income — so that was a good place to start.
So I started digging into what it took to start a successful business, and I started seeing articles suggesting that the best thing to do was to market every skill I had that people would pay me for.
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Before I knew it, I was editing, ghostwriting, managing social-media accounts, coaching freelancers, consulting on building brands, pitching myself and others for media features, and getting paid to write for publications. It seemed like I was all over the place. Sure, I had multiple streams of income, but there was too much going on.
I took a step back and realized a thread joined all of these tasks together: I am a communicator. Everything I did then and that I do now in my business revolves around communicating.
Now I'm a publicist, a writer, a coach, and a consultant. I've created a small arsenal of digital products including workbooks and masterclasses that teach my customers about productivity, marketing, branding, and public relations. I collaborate with other business owners whose products or services complement mine, and I promote their products as an affiliate. I've also created a stream of income speaking and training. While the income isn't passive like the affiliate income, it doesn't feel like work because I speak about things that excite me and that I am passionate about sharing.
When you are looking to diversify your service and product offerings, consider all the things you can teach others about your area of expertise. Try these three steps:
Condense your knowledge into an informative e-book and create a mini-course teaching a specific tactic someone can use
Not only do you have to write the e-book or create the course only one time, but once it's out there it can sell while you're sleeping! Imagine putting in the work to develop your content one time and then being able to watch it sell repeatedly.
Google became my best friend as I read a few articles on how to set up my course or sell my e-books from platforms like Thinkific and Teachable. I did a bit of on-the-job training by trying both platforms before I made my decision based on ease of use.
I learned quickly that having digital products available for sale at all times increases your chances of establishing your credibility and allows you to "make money in your sleep." Not every stream of income you have needs to be attached to your immediate attention. The creation of passive-income products allows you to reach people without taking time out of your day.
Consider being an ambassador (aka affiliate) for the products and services you already use
Affiliate marketing is where you get a commission for selling someone else's products. The first time I saw the power of affiliate marketing was when I noticed that my email-marketing platform sent me an email that said "Get a free month for everyone you recommend to use our platform!" And though I was paying only $15 a month, I figured that if one person started using the platform, it would be $15 I could save.
I started looking at every tool I was using to see whether it offered the same type of promotion, and most did. Some offered a free month of service, while others offered 20% residual of every service sold. Email-marketing platforms, scheduling apps, e-commerce platforms, and more typically have a form of affiliate marketing to offer. It's not a lot, but if you leverage the power of your network, it adds up.
If you like public speaking or teaching, turn your expertise into signature talks or workshops
Joining your local Toastmasters program can help you build a foundation for public speaking. If you are a member of any professional associations, chamber-of-commerce clubs, or business groups, find out their process for speaker selection at their meetings or events.
To get my feet wet, I started searching Facebook for business owners who were hosting events and needed speakers. I did about seven free events before I started packaging my talks to get paid to speak.
There are organizations that will pay for your genius, so position yourself to share it. Even if you don't get paid up front for speaking, learn to master the art of selling from the stage or the back of the room. Either way, you'll grow your influence and reach by leveraging your expertise and connecting with more people, and you'll have an additional avenue of earning extra income.
Maleeka T. Hollaway is a millennial, entrepreneur, speaker, and writer obsessed with personal development, leadership, and small-business growth. Her goal is to teach small-business owners and entrepreneurs to position themselves to grow sustainable businesses and brands. Meet her on www.MaleekaHollaway.com.
I’m an unconventional business owner. I’m never going to tell you that you “have” to do something. I’m never going to insist there’s a “right” answer. And I’m never going to ask you to work 60-plus hours a week. I certainly don’t.
While I totally respect the hustle, that all-in, go-big-or-go-home attitude isn’t for me. I tried it 20 years ago, and it almost killed me. Since then, I’ve found that success doesn’t have to come from a self-sacrificing grind and built a multiple six-figure business working no more than 30 hours a week.
Here’s my best advice creating a thriving business without letting it run your life.
Get clear on what you value
One of the most amazing things about creating your own company is your ability to design something that aligns with your values. Whether you value massive financial success, tons of free time to spend with your family or traveling the world, a creative outlet, or the opportunity to make a huge impact on the world, at the end of the day, you get to choose.
This means the first step to creating what you want is identifying your top two, overall life values — and you can only have two. When you have more than two, you’re no longer focused enough to work and live according what truly matters. Your right two values are the ones that are true to you, not ones that you’ve been told you should have or believe are expected of you.
Deliberately create your schedule
When you pinpoint your top two values, your next step is to be ruthless about structuring your work and life around these values. After all, if you’re not spending your time in ways that reflect your values, then you aren’t truly living those values.
This means, if you value time with family, your desired family time goes in your schedule first. If you value health as I do, time for self-care and time not working are essential. If you value travel, put time in your schedule for that.
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There is no one right way to schedule your life other than however reflects your values. Give yourself permission to do things your own way. This means not following a morning routine, four-hour work week, or workation schedule that some so-called expert has declared is the secret to success. Your secret to success is whatever reflects your values.
Hold yourself accountable
Although this may sound harsh, the truth is, the rest of the world does not care about your values or your schedule. This means you hold yourself accountable to both.
One of the best ways to do this is to create a schedule that plans each day in 15-minute increments. I realize this sounds extreme, and it’s always met with a lot of pushback from my clients. The results, however, are undeniable.
When you deliberately plan and track your time, you quickly see how easily you give in to distractions and procrastination, how much time you spend doing busy work, and that you ultimately have more control over your schedule than you’ve ever realized. This epiphany might sting at first, but once you get over the ego hit, you can take back control and truly live and work according to your values.
In time, you won’t need to plan or track your schedule so closely. You’ll develop habits of focus, anti-procrastination, and routines that reflect your values. You’ll naturally manage your schedule in a way that reflects your values.
Get really good at saying no
To hold yourself accountable to living your values, you have to say “no” a whole lot more than you do right now. You’ll be saying no to everyone — from friends and family, to coworkers and employees, to new opportunities. The world is going to keep asking for more from you, and you have to hold the boundaries set by your values.
The good news is, when you are 100% sold on your own values and how essential they are to your life and work, it becomes easier to say no. Sure, the person on the receiving end might not be thrilled with your response response, but the alternative is sacrificing your own values — and this is exactly what you’re trying to stop doing.
Create systems for everything and delegate
Once you’re operating on a schedule that reflects your values and armed with the ability to say no to everything that tries to pull you from those values, you’re primed to achieve greater success. This is when it gets fun.
With a slimmed-down, focused schedule, you can easily see what work helps you achieve the maximum results you’re looking for without sacrificing your values. From here, you can create effective systems, delegate more, and free up your time to do the work that grows your company. In a nutshell, you can achieve greater success without sacrificing what matters most to you.
Working but not hustling — forever
With each phase of business growth comes further refinement at each step. Revisit your values, your schedule, everything pulling you from your values and schedule, your systems, and your team. Update and fine-tune each area to help you achieve your next level of success. It’s part of a never-ending spiral of upward growth, helping you create a successful business without ever sacrificing that which truly matters to you.
All of this means you don’t have to be a workaholic ever again— unless that’s something you value.
Jenny Shih is a business coach who has taught more than 25,000 women how to earn a full-time income working 30 hours per week or less as online, service-based entrepreneurs.
Drawing on her decade of experience in high tech and her training with Martha Beck and spiritual teacher Byron Katie, Jenny guides her clients through a no-fluff, step-by-step approach to creating thriving businesses they love without having to work long hours or make huge sacrifices.