30 best insights and pieces of advice for entrepreneurs

With collective intelligence being a disruptive innovation theme we are investing in. We found these great collective insights from entrepreneurs and annual series from First Round ventures to be a great resources.

The 30 Best Pieces of Advice for Entrepreneurs in 2020

Here on the Review, we have an annual tradition that we look forward to each January. We press pause, pour ourselves a big cup of coffee, and pore over each article we published the previous year, with an eye for the very best pieces of advice that we’re still thinking about, one year on.

Since the Review’s genesis in 2013, we’ve interviewed hundreds of folks who are among the very best at what they do — and 2020 was no exception. We cherish the opportunity to carefully parse through the advice of the experts that were featured on the Review’s digital pages — from repeat successful founders, to events gurus, to top psychologists. (If you’re curious to see how this collection has evolved over time, check out previous editions from 2019, 2018, 2017, 2016, 2015, 2014 and 2013.)

As we leafed through what we published in 2020, a few themes stood out to us. No 2020 retrospective would be complete without a nod to “these unprecedented times” (and we’ve given up combing the thesaurus for any language to replace this rote phrasing). Despite the whirlwind of changes and explosion in content since 2013 — from the rise of Substack newsletters to the endless Twitter threads full of advice for entrepreneurs — our aim has remained consistent over the years. We seek not to chase trends or tackle specific industry verticals, but rather to publish enduring, evergreen company-building advice that both stands out from the crowd and can be put to use right away.

But this past year there was a pressing need to cover unexpected, timely topics where folks were clamoring for guidance. With our editorial plans upended, we quickly shifted gears. More importantly, founders, leaders and experts stepped forward, generously opening up their playbooks to offer wisdom that met the moment, from navigating the lightning-quick shift to virtual work, managing through turmoil, and adjusting your leadership mindset when it feels like you’re running on empty. You may have seen a lot written on these particular subjects across the internet, but as is always our goal, we hope the Review’s takes offered something a bit different.

2020 also 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 — some that you may agree with, and others that may not quite ring true for you. 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 hard-won wisdom 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 must-ask interview questions for candidates.

We even pushed ourselves out of our comfort zone of the written word and launched a brand-new podcast, In Depth, where we deliver the same signature interview style we’ve cultivated on the Review directly to your headphones.

We may not know what 2021 has in store, but as we reflect on the year that’s passed and what’s still to come, our sincere hope is that you continue to find a dose of inspiration, an actionable new tactic to try, or a compelling story to sink into whenever you turn your attention to the Review. We know the time you spend diving into an article or popping in your headphones is more precious than ever, and we continue to be sincerely grateful to all of you for spending it with us. Here are the 30 best pieces of advice from our articles last year — take them with you as we look towards brighter days to come.

1. Bookmark these 40 questions to ask interviewers on your next job hunt.

When it comes to interview advice, there’s plenty to go around for hiring managers. But for candidates, when the tables inevitably turn and the interviewer asks, “Do you have any questions for me?” it’s critical to not only stand out from the crowd, but also unearth some valuable information about whether this prospective company’s a good fit.

That’s why we published a follow-up to one of our most popular Review articles, sourcing ideas for questions candidates should ask from some of the sharpest folks we could find. Our aim? A robust roster of questions that go much deeper than “What’s the culture like?”

We’ll highlight a handful of our favorites below. Our advice? Narrow down your list of must-ask questions to the hiring panel by focusing on your deal-breakers — what would make you walk away?

• What are the top three customers that you’ve won, and the top three customers that you’ve lost? “You get a real sense of how the company is doing in the market, what's working well — and what's not,” says Max Branzburg, VP of Product at Coinbase.

• What’s something that would only happen here but wouldn’t at other organizations? “The culture of a workplace — an organization’s values, norms and practices — has a huge impact on our happiness and success,” says Adam Grant.

• What area of the business would you say this company is behind on, given its stage? “This question can often highlight functions that are not established and areas where you have to fill in cross-functionally that might surprise you,” says Cristina Cordova, Head of Platform and Partnerships at Notion.

• Can you tell me about your founding team’s background and why you’re tackling this particular problem? “More job candidates should think like an investor. After all, joining a company is one of the biggest investments one can make,” says Ryan Hoover, Founder of Product Hunt.

• How would your team describe you? “What’s your management style?” is an all-too-common question, more likely to elicit platitudes than nuggets of wisdom. “Framing it from the perspective of the reports prompts the manager to think beyond their intent and instead consider their actual working relationships with the team,” says Zainab Ghadiyali (alum of Airbnb and Facebook).

• Can I see your calendar for the week? “I believe there’s truth in calendars. If someone tells you in an interview that they really care about the learning, development and mentorship of their employees, their calendar should reflect that,” says Anna Binder, Head of People Operations at Asana.

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by Peter Bordes