How to Succeed in 2020

How to Succeed in 2020

Twelve entrepreneurs and industry experts talked us through the trends to come in the next year — and offered advice on how to navigate your way to a successful future.

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22 min read

This story appears in the
December 2019

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We’re not just about to enter a new year. We’re heading into a whole new decade. That means plenty of fresh opportunities, new chellenges, and the chance to build businesses that will create a better tomorrow. Trust the advice of these 12 experts and entrepreneurs — who highlight the trends and topics that will impact the year ahead — and get ready for a successful 2020, and beyond. 

How to Succeed in 2020

Digital Reputation

Start playing defense — now!

True story: A CEO gets a call from his boss asking him to wire transfer $243,000, which he does. Only it’s not his boss; it’s an astonishingly convincing deepfake, slight German accent and all. Made with AI-based technology that allows you to alter — or entirely fabricate — audio and video, deepfakes can “document” someone saying or doing something they never said or did. If managing digital reputation has become an entire industry, these synthesized clips promise to send even the pros scrambling, says 2019 MacArthur Fellow Danielle Citron, a law professor at Boston University Law School and leading cyberprivacy expert. She predicts all kinds of economic sabotage: a deepfake video showing the CEO drunk the day before his company’s IPO; an outspoken businesswoman naked in a sex tape; an R&D guy admitting he hid studies showing a product was cancerous. Right now, the best way to protect yourself may be to keep a ready log of your whereabouts to debunk these frauds. “Every day, deepfakes are getting easier to make and harder to distinguish from real footage,” she says. “Brace yourself.” 

Related: The 7 Strengths and Habits That Successful People Possess

How to Succeed in 2020

Employee Benefits

Your team wants more than just free snacks. 

As the founder and CEO of national staffing, recruiting, and culture firm LaSalle Network, Tom Gimbel knows a thing or two about what employees want — and that they have more options than ever. “Unemployment is just so low,” he says. “It’s an employee’s market.” To stay competitive, Gimbel urges business owners to offer true benefits rather than flashy perks. “Everyone has free food and fun games in the office,” he says. “But what employees really want is a 401(k) and match.” Yes, Gimbel says,  plenty of entrepreneurs just can’t afford to offer that benefit — but it’s about meeting in the middle. “Tell a candidate, ‘Based on our business, we start matching your 401(k) at x percent after you’ve been here two years, and after three years, it’s dollar for dollar,’” he says. And when that coveted talent asks about growth opportunities in an interview, don’t mistake their ambition for greed. “This is the age of validation, and people want to know in no uncertain terms: What’s my path? The best managers can provide answers. It’s just about clear communication.” 

How to Succeed in 2020


It’s time to pick sides.

In 2020, California’s new bill AB 5 threatens to kneecap the booming ride-sharing industry. Come January, it will be harder for companies like Uber and Lyft to classify their drivers as contractors versus more expensive employees. Although Uber, Lyft, and DoorDash have pledged $90 million to fight back,  “It’s very hard to see how they will avert this,” says Bradley Tusk, whose company, Tusk Ventures, invests in startups with growth potential if they can clear those regulatory hurdles; then a separate division of the company works with them to do that. “They need to redefine the narrative from ‘big, evil Silicon Valley companies versus hardworking people who are getting screwed over’ to telling consumers, ‘Your DoorDash delivery time is going to take longer, and Uber will cost more per trip.’ ”   

For startups in the space, “I would lean into it,” suggests Tusk, who helped Uber take on the Taxi Commission in New York. “Say to employees, ‘You want healthcare? We’ll provide it. You want to organize? Go for it. We believe a happier workforce will make us more money.’ Let Uber be the bad guy.” 

Elsewhere on the regulatory horizon: Telemedicine startups, which have so far operated under the radar, are now being noticed by entrenched interests and face state pushback next year, but ultimately will be a great growth area. Tusk believes barriers will come down for autonomous trucking, self-driving cars, and eSports betting a little more slowly. “We’re really psyched about eSports,” says Tusk. “That’s the biggest opportunity out there by far.”

How to Succeed in 2020

New Tech

Futuristic tech will shape everything you do.

Futurist Amy Webb doesn’t make predictions. She calculates probabilities of upcoming scenarios for clients like Microsoft and Chevron, using data and other insights as her crystal ball. She’s the founder of the Future Today Institute and a professor of strategic foresight at NYU Stern School of Business, and her latest book, The Big Nine, examines how tech giants are shaping the future of AI. No matter what your business, she stresses, you can’t ignore these new technologies.

What’s one of the most interesting developments in AI right now?

I would say scoring. Our behavior online and offline is being tracked — and companies big and small are collecting all this data and using algorithms to parse that data and calculate a score. The score can determine everything from how likely we are to break the law to how much we’re willing to pay for a roll of toilet paper. But there’s a bunch of new issues they will have to wrestle with, certainly, next year. 

Like what?

I’ll give you a draconian example. China’s social credit score system adds or subtracts points based on what a person does — like if they speed, what they say about the Chinese Communist Party. High scorers get discounts and other rewards. But last year, 17.5 million people weren’t allowed to buy plane tickets because they didn’t have enough points. And now China has started scoring companies based on their behavior. We may disagree with the process. But at least they’re transparent. In the United States, often scoring is intentionally obfuscated. Does that open you up to legal scrutiny in new ways? It may. So businesses need to think about: What data are you going to access? And how do you make sure that you’re being transparent to both your vendors and customers? 

According to your annual Tech Trends Report, global sales of consumer wearables are estimated to top $38 billion this year. But is the watch really catching on? Are we heading for a post-smartphone era?

The smartwatch market is actually quite robust, and new smartphone sales are flat or receding. You could say Google Glass failed, and Spectacles was a failure. But bear in mind there was Friendster and MySpace before Facebook — it was the third iteration that took off. Now, what does this mean to a business? Well, everything. Basically, once you can wear glasses that let you see data and import people, it shifts how we talk to each other. Imagine calling a help desk and talking to a face versus just hearing this random voice — and with AI detecting emotion, there’s a new kind of customer service waiting to be born. Or, if you’re a retailer, you may no longer need physical store associates, because you’ve got somebody working in a remote call center who looks like they’re there. I know this sounds sci-fi, but I’ve already seen a version of it. 

Your latest report also suggests voice search optimization is the new SEO.

With people speaking more and more to their devices, voice search optimization — which content shows up first when you ask questions, whose brand, and under what heading — is going to be something we’re all talking about.

How can the average person stay up on all these complicated tech trends?

We have to pay attention, because the constellation of all these technologies will shape everything we do. And the best possible preparation is something that is incredibly easy and can be done today: Spend a couple of minutes reading up on what’s happening in technology. If you can learn enough to explain what AI or Blockchain is to your friend over coffee, you can start to tell signal from noise. And you’ll wind up being either a first mover who is smart or somebody who is patient and calculating. Either way, that is how you think like a futurist.

How to Succeed in 2020


Create better experiences (with data).

Stores are closing by the thousands. Chains like Forever 21 are going bankrupt. How many times have we heard that we’re living in the retail apocalypse? “I don’t believe it,” says Praveen Adhi, retail operations lead and partner in the Chicago office of consulting giant McKinsey & Company, which has set up a lab in Minneapolis’s Mall of America to test how stores need to reimagine their future.

So, really, brick-and-mortar is here to stay?

Our research shows that, overall, retail companies have been doing very well, actually, in delivering shareholder returns, but there’s a huge disparity between winners and losers, especially for apparel, compared with other sectors. And I think you’re going to see that continue — or get even worse. So what are winners doing? And what does that mean going forward? That’s why we did the store. 

It’s called the Modern Retail Collective and is a hive of selected brands and new technologies that will rotate every few months. What’s the first curation like?   

We have a smart mirror where a shopper can customize Kendra Scott jewelry to see what it would actually look like, and there’s another tool that helps you find the best-fitting ThirdLove bra. I think over the next year or two, you’ll see retailers invest in this kind of technology because customers want a more personalized experience in stores, like they get online. Ultimately, we’re all trying to figure out why they buy. 

How do you figure that out?

Through the use of cameras and sensors, we can tell what a customer is doing in the store and what it has to do with whether she purchases something. Does it matter if there’s an associate nearby? What does it do if she walks to certain parts of the store? And it’s all anonymized data, but it’s powerful in helping brands understand the best way to lay out their stores and where to put their labor. 

What about the operations side?

You’re going to have to transform the cost structure of the store and shift dollars to customer service. So you’re going to have to automate operations that don’t impact the customer experience. There are new technologies, for example, to tell you that a product is missing on the shelf and it’s costing you $50 right now. That immediately fixes an issue that is hurting customer service and hurting s

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