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.
How to Succeed in 2020
Image credit: Cecilie_Arcurs | Getty Images
15+ min read

This story appears in the December 2019 issue of Entrepreneur. Subscribe »

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. 

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

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.” 


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.”

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.


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 sales, and it means the manager doesn’t have to sit in the back room sifting through 15 reports. 

If I’ve got a small store, what’s a good first step going into 2020?

Really take the time to understand your customer, who she is and why she’s physically going to get in the car, drive to the mall, and come into your store versus shopping online. And then experiment with technology, a lot of which is fairly low-cost. The bigger retailers can’t do it because they have legacy systems that don’t talk to the new ones. In fact, there’s a huge opportunity for entrepreneurs to create platforms that connect all these technologies together -- and then to help companies turn all data into insights. 


Think circularity.

Carbon footprint, renewable energy, and zero waste are familiar buzzwords. But if Nike is any indication, the new movement in sustainability is circularity: using high-quality materials made from fewer resources and with their life cycle in mind. “We’re highly focused on designing waste out of our manufacturing processes, which is a trend that’s growing across sectors,” says Jaycee Pribulsky, VP of sustainable manufacturing and sourcing at Nike. Just within apparel, she points to efforts by companies like Eileen Fisher and Levi’s that used old clothes to create artworks or insulation. In Nike’s case, dedication to sustainability has reliably led to profitable innovations like Nike Air, which contain recycled manufacturing waste. ”If Nike Air were a stand-alone athletic company,” says Pribulsky, “based on revenue, it would be the third-largest in the world.” To further innovation, Nike has launched a challenge where any employee can submit ideas on minimizing carbon and waste. “It will take all of us to get where we need to go,” she says.

Related: 10 Busy C-Suite Executives Share How They Make The Time To Be Great Parents


Keep it real.

When Kylie Jenner does one sponsored post on Instagram, she makes more than $1 million, according to the social media tool Hopper. South of that insane influencer stratosphere, what personalities will matter in 2020 -- and how will the dance between creators and brands play out? According to Justin Osofsky, COO of Instagram and a former VP for Facebook, it’s all about the very niche and the über-authentic. “Quil Lemons is an emerging creator who uses photography to challenge notions of gender and race,” Osofsky points to as an example. And in fact, Lemons’ exposure on Instagram has helped him land gigs and partnerships with everyone from Vogue and Gucci to Target. In-app partnerships between brands and influencers are evolving, too. “We’ve been testing the ability to shop directly from creators,” Osofsky says. “They can tag up to five items and [followers] can click through and order right on Instagram, and branded content ads help companies understand the activity that’s happening [with influencers] and extend their reach to audiences they know are interested. Done well, it’s a win for all sides.”


It’s about to get immersive.

Ted Schilowitz gets paid the big bucks to play video games and fly in VR. He’s Paramount Pictures’ futurist in residence, so when he’s not in an alternate reality, he’s looking into why people adopt certain technology and apps to divine the next chapter in captivating audiences. And that, he says, will be the age of spatial storytelling.   

As VR headsets go mainstream, augmented reality and virtual reality will be transitioning into a new form called mixed reality, or MR -- which means that entertainers can place their audience inside the narrative, giving them the sense of moving through a scene, interacting with objects and characters. In five years, he believes, mixed reality tech will improve so much, “it will really feel like it’s happening to you,” says Schilowitz. “It’s like taking a theme park into your home and being pulled into a simulation-style attraction.” 

Right now MR is mainly appropriate for adrenaline-pumping action, adventure, crime, and horror, but Schilowitz insists that as it develops, it will enhance any good story. “When we learn things in physical space, we learn them differently than if it’s a two-dimensional space,” he says. “That’s why in a hotel, once you put the key in the door that says 317, you know where the room is; it’s much harder to remember the number if someone just told you. That’s the power of mixed reality.” And for brands, Schilowitz warns, “They need to learn how to take advantage of this before they need to know how to.”

MR will also have the power to transform social media, Schilowitz says. People are already meeting in artificial spaces via their avatars. (“I’ve done karaoke in VR, which was just as painful as doing it in real life,” he jokes.) And he predicts that Facebook’s new VR product, Horizon, is only the beginning: “Mark Zuckerberg and his team have a strong affinity for MR, and it’s well-discussed that it’s because of the ability to make it the next social platform. I think they’ll get it right eventually.”


Don’t hunt attention; attract it.

Dean Kamen is known for introducing the Segway back in 2001. But to think of him as a weird gizmo guy would be to miss the genius of a man out to save the world. As the founder of DEKA Research & Development, which now has some 800 engineers, Kamen has innovated everything from a water purifier for developing countries to a kidney dialysis machine for the home to the iBOT, a wheelchair that goes up and down steps and -- surprise! -- is about to pop a wheelie in automating corporate America. 

What will be your biggest challenge in 2020?

I’d be happy to tell you, but we’d have to kill you. 

Let’s say you don’t. How should entrepreneurs of all ages look to the future?

Don’t waste your time making a quick buck on some stupid consumer product. I’m sorry, but we’re in desperate need of better medical outcomes, better ways to give people energy and transportation without destroying the environment. Use your talent to do something good for the world, and that will be good for you as well. 

So, about this iBOT stair-climbing wheelchair of yours...

When Fred Smith [founder and CEO of FedEx] called over a year ago and said, “We want to make the world’s best last-mile delivery bot,” I said, “Fred, I could start from scratch and spend $100 million, but, well, if we pull the seating system off my iBOT and put a cargo pod on top, it will go through doorways and up and down curbs -- and help me get the wheelchairs to all those vets who desperately need it.” He literally said, “Can we get together tonight?” And we now have three of those little demo bots trundling autonomously around Memphis, Dallas, and Manchester, New Hampshire. They call it Roxo.   

The self-driving part must have required a bit more than taking off the seat.

Oh, yeah. No, no, no. We had to put a whole team together to create a very advanced little Roxo that’s learning as it goes everywhere using AI. It is astounding what this puppy will do. 

And FedEx is collaborating with companies like Target, Walgreens, and Walmart on this bot, right? Is the delivery guy toast?

Remember, this is not an alternative to a fleet of 747s flying all night or the trucks that go from the centralized point. This is a totally new and incremental business for them. 

What other automation trends do you see down the pike?

The biggest one we’re working on is building a platform that allows the large-scale manufacture of replacement human organs. With an $80 million jump-off grant from the Department of Defense, we’ve put together a coalition of more than 87 companies and plan to demonstrate a platform in five years. It’s essentially about robotics. 

Can we quickly talk electric scooters? Will the current craze for micromobility continue?

Our first Segway came from the iBOT, a class 3 medical device. Now [electric scooters] are cheap enough that these companies [like Lime and Bird] can afford to throw them all over the place and charge people to use them for a few minutes. I think there’ll be a backlash. And I think their bad behavior will make it hard for well-thought-out, clean, lightweight alternatives [to automobiles] to be adopted.

What problems keep you up at night?

Trying to get my FIRST robotics program [for kids] into every country in the world. We’re in 72,000 schools in the U.S. In October, the FIRST Global event was in Dubai. The game was to make robots able to pull as many of these little objects off the field as possible, which represent plastics taken out of the ocean. I’ve been at this for 30 years. We hire these kids. I’m looking for talent!


Don’t fear the immediate future. 

Economists chatter about a looming recession, and entrepreneurs worry it’ll spook investors. But Ben Horowitz, cofounder and general partner at Andreessen Horowitz (and one of Silicon Valley’s most celebrated VCs), isn’t fazed. “Economists predicted 57 of the last 17 recessions,” he jokes. “It’s entirely unpredictable.” And anyway, Andreessen Horowitz and many firms like it invest on a 10-year horizon, meaning it expects today’s investments to pay out a decade from now. (So what is Horowitz excited about investing in next? He says that in the coming decade, his focus will be AI, crypto, computational biology, device proliferation, Internet of Things, and AR/VR.) With this long-term thinking, Horowitz says, recessions don’t factor into his decisions. And he believes venture-backed entrepreneurs should operate the same way. “You want to have plenty of money in the bank to get to your next milestone, where you can raise more money,” he says, “but I think smart entrepreneurs ought to do that whether there’s a recession coming or not.”


Do it at any scale.

Services like Spotify and Netflix may have popularized the “recommended for you” prompt, but it’s now technologically possible for entrepreneurs to add similar services to their smaller businesses -- and they should, says Jonathan Neman, cofounder and CEO of salad chain Sweetgreen. “This is a big theme for a lot of us,” he says. His company has built an algorithm that learns every time a customer orders on its app -- whether she’s gluten-shy, on keto, into salty, sweet, or creamy -- and then suggests one or two bowls from the two-million-plus variations Sweetgreen can make. “So you get a text message at 11:00 a.m. that says, ‘Hey, do you want this for lunch or this?’” says Neman. (The service should roll out next year.) He sees companies across industries trying out versions of this; one he’s been watching is the gift-box brand FabFitFun. It’s not easy building operations that can deliver personalized service, he says, but he thinks it’s worth the investment. “It’s the joy of choicelessness,” he says.

Related: 8 Ways to Drown Out Disappointment


It’s about to get immersive.

The old way of recruiting doesn’t work anymore,” says Pieter Schalkwijk, head of talent acquisition at Kraft Heinz, who’s responsible for hiring around 500 people a year in Europe, the Middle East, and Africa. He no longer even looks at résumés at the start of the process. “I saw we were hiring a lot of mini-me’s, from similar universities. I also wanted more data-driven decisions, not just ‘I like this person.’ ” 

So in August of 2018 he started using an AI-powered platform called Pymetrics to help select 45 high-potential hires from 12,000 applicants for a special trainee program. Pymetrics uses neuroscience games to test candidates for traits like risk-taking and resilience, and matches them to a customized job-­specific algorithm based on his division’s top performers; then they check for bias with their auditing tool. 

Schalkwijk has seen more diversity in every sense, including “way more creative pioneers versus the logical, driver  types.” And he plans to use the platform for more jobs next year. “Not looking at literally every CV takes a bunch of work off of us,” says Schalkwijk, who predicts that in the future, skills will become more relevant than formal education. The experience has proven to him that technology significantly improves hiring, and he’s not the only one; Pymetrics’ clients include Mastercard, Unilever, and LinkedIn. Schalkwijk only hopes that tech can make the recruiting process better for applicants. “That’s very important, especially for a company like ours, where, if we reject a candidate, I still want them to buy our ketchup.”

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