The 30 Best Pieces of Advice for Entrepreneurs in 2020

Happy 2021 (sure feels good to say that)!

The new year always presents a twofold opportunity: to reflect on the past and then draw from those insights to shape our future. And as we close the chapter on 2020, there's plenty of hard-won lessons to take with us into a brand-new year.

Here on the Review, we have a tradition that we look forward to ever January, and this year was no exception. We pore over every single article we published the previous year, and parse each one to extract the most impactful tactics and key takeaways we can't stop thinking about, one year on. Today, we're pleased to present our eighth edition of this highly-anticipated list.

This time around, a couple themes stood out. 2020 brought the strength of pooling wisdom and leaning on community into sharp focus. No one person has all of the answers, and there’s power in bringing together plenty of different perspectives. We tapped into that impulse more than ever this year, whether it was calling on a slew of recession-era investors and CEOs for their playbooks in the earliest days of the crisis, drawing on the experiences of over a dozen design leaders, or crowdsourcing the best tips on managing up and favorite must-ask interview questions for candidates.

Even our signature profiles, while not explicitly covering the unique challenges of 2020, featured folks who were frank about the not-so-glamourous side of startup life — from Drop's Steve El-Hage admitting he "learned everything the hard way" as a first-time entrepreneur, to Upstart's Dave Girouard on the heels of an IPO reflecting on what it's really like to quietly build a company most aren't paying attention to, and Review favorite Molly Graham's own managerial mishaps.

With all that in mind, here are the standout pieces of advice we heard in 2020. We hope that you can apply them to whatever's this year throws at us.

-The Review editors

Here's a sneak peek at what you'll find on the list:

-Tip #2: Invest in Your Writing Skills. 📝
Dave Girouard, CEO of Upstart, outlined plenty of tactics for shaping up your writing. One particularly simple tip? Eliminate all unnecessary words. “Words fight for your reader’s scarce attention. Thus, every unnecessary word detracts from the important ones."

-Tip #5: Focus on managing the what, not the how. 🤔
“I see so many managers getting really bogged down in the literal process that someone is going through in order to achieve a goal," says Molly Graham, COO of Lambda School. But at the end of the day, there’s only one thing that matters: Did they achieve the goal?”

-Tip #23: Set a cultural North Star to patch up the gaps of remote work. 🌟
“When it comes to working remotely, messaging expectations for deliverables is important, but that’s only half of the equation. It’s just as important to consistently message and reinforce work norms — how you all treat one another,” says Maggie Leung, VP of Content at NerdWallet. 

-Tip #30: Manage up, down and sideways with these tactics. 🔃
“Don’t save up a big topic until you feel you have all the answers—anything worthwhile takes time to build. An old manager had a ‘rule of seven dippings,’ which means anything complex or abstract takes multiple exposures in order for someone to internalize it,” says Ralph Loura, SVP CIO of Lumentum.

Resources worth sharing: 

• Nikhyl Singhal, one of the Review's favorite product leaders, outlines three crucial skills to develop before taking up the executive mantle.
• Scott Galloway's seven business predictions for 2021.
• Airtable's Head of Diversity, Equity and Inclusion, summarized what he learned after talking to 20 DEI experts.
• Tested tactics for unplugging and making time for "life" amidst remote work.

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