The 30 Best Pieces of Advice for Entrepreneurs in 2021

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“Every article will serve up tactics that you can use today to change your company and your career.”

This was one of the three promises we made when we first launched The Review back in 2013. It was a pledge to stay in the tactical weeds, to find the sweet spot of both enduring, evergreen advice and the “I’ve gotta try that out today” kind of read. (Or as one of our readers recently put it, “oddly specific, yet perfectly helpful.”)

There’s power in the specifics, in the counsel that shares the how-to, not just the what-you-should-do. In the story of the CEO who analyzed every 15-minute increment of his calendar for the past two years. In the targeted question set one founder uses to compel others to give her better feedback. In the detailed framework for hiring a VPE. In the advice on how to find a signature topic for your first public speaking keynote. In the case study on how one marketing team secured +100 podcast interviews for their founders in six months. 

If these specific examples sound somewhat familiar, then you’ve been reading along this year, as they were all drawn from articles we’ve penned in the past 365 days. And they’re still top of mind for us right now for a particular reason. 

Since 2013, we’ve committed ourselves to an annual ritual, one that serves as an opportunity to both take stock and remind ourselves of that early promise to stay tactical. Each time we turn the page to the new year, we comb through every article we published over the last one to concentrate the standout tactics into one actionable guide of advice. (To see how this project has evolved over time, check out our installments from 2013, 2014, 2015, 2016, 2017, 2018, 2019 and 2020.) 

As we set about to pluck out the tactics, quotes and frameworks from the previous year that we haven’t stopped thinking about, a few themes invariably start to emerge. It wouldn’t be a 2021 retrospective without a nod to the “Great Resignation” — folks up and down the org chart are reconsidering their career goals and resolving to pour more into their own personal development. It’s a topic we tackled head-on, whether by tapping our First Round community to gather their tips on how ICs can take charge of their own careers, getting therapist Minaa B.’s take on making self-care tactical, or crowd-sourcing ideas for upping your management game.

That very same itch pushed others to try on the founder’s hat for the very first time, which is why we kept a keen focus on lessons for first-time founders this past year — particularly on that messy pre-product/market fit phase, where founders are staring down a lump of clay on the pottery wheel, hoping to sculpt it into an enduring work of art. Given that advice for founders tends to come from those who are many years removed from those early chaotic days, we relished the opportunity to speak to folks who are still early in their founder journey, like Ryan Glasgow of Sprig, Rick Chen of Persona, and Tara Viswanathan of Rupa Health

As always, we hope you find relevance, resonance and few ideas to try out for yourself in the following roundup of the 30 best pieces of advice from our articles last year. Here’s to all the micro-actions and tactics that will transform companies and careers in 2022 — and to the startup leaders who will generously share them.

When it comes to upping your management game, most advice tends to focus on the big tentpole moments — hiring, delivering feedback and checking in regularly. Of course, holding regular 1:1 meetings and honest performance reviews are critical items on your manager checklist to get right, but there are plenty of smaller habits that are just as important to pay attention to. So we sent out a call to startup leaders in the First Round community to crowdsource a list of the small things that make great managers stand out. Here are a few of the highlights: 

“Great managers demonstrate self-awareness and empathy by sharing their working style preferences and development areas. I’ve always appreciated when managers provide an onboarding guide to who they are as a person and a manager. This should include their work styles, expectations of their directs, values and motivations, areas of feedback they are working on and decision-making preferences,” says Dennis Yu, VP of Program Management at Chime.

“I trust you, make the call” might be the six most powerful words you can hear from a supervisor,” says Sean Twersky, VP of Operations at Sprig.

“Bang the drum — literally. A friend of mine loves using props to get her team fired up, like a tambourine she shakes when she’s excited about what someone says. Great managers do small things to help their teams have fun and take the work seriously while not taking themselves too seriously,” says Sunita Mohanty, New Product Experimentation at Meta. 

Each individual person’s strengths are superpowers that lead to an all-star team. Find moments to recognize specific ways that each person’s superpower shines and encourage team practices around sharing gratitude for each other.

Photo of Sam Corcos
Sam Corcos, CEO & co-founder, Levels

“As a startup CEO, being a master at time management should be one of your core competencies. You’re going to have a lot of balls in the air and you need to make sure you don’t drop them — or at the very least, ensure that they don’t drop silently,” says LevelsSam Corcos. As a repeat founder, he’s tinkered with a few time management techniques over the years, but the biggest win came from ditching his to-do list altogether and leveraging his calendar instead. 

The problem with to-do lists is they lead to unrealistic optimism about how much you can accomplish because items on a to-do list are untethered from the constraint of reality: time. 

Tactically, if Corcos has a task that needs to be completed, he now blocks off time for it on his calendar. “I used to have the habit of overcommitting myself, which became a major source of anxiety in my life because I was dropping balls left and right, and it led me to disappoint a lot of people when deadlines would slip,” he says. “When people ask me now, ‘Can you have this done by Friday?’ I can easily look at my calendar and respond, ‘I have exactly two hours open this week, so if it’s going to take more than two hours, we’ll have to change my priorities or I won’t get it done until next week.’ Having this level of clarity on my time has been a huge win,” he says.

Photo of Gagan Biyani
Gagan Biyani, CEO & co-founder, Maven

The typical approach to getting a startup off the ground is to conduct some customer research, throw an MVP out there as fast as possible, and cross your fingers. After being early at three startups that achieved over $1M in run-rate in their first six months of going live, Gagan Biyani has landed on an alternative approach. Here’s a condensed glimpse inside his MVT framework which resonated with so many founders last year. (Be sure to read his article in full to soak up all the tactical nuances.)

The difference between MVTs and MVPs: “An MVP is a basic early version of a product that looks and feels like a simplified version of the eventual vision. An MVT, on the other hand, does not attempt to look like the eventual product. It’s rather a specific test of an assumption that must be true for the business to succeed,” he says.

If you build an MVP, you start to think about the 20 features you might build to make people happy in a market, which takes your eye off the one specific insight that the customer actually cares about. Purity breeds success.

Instead of building a full-on MVP, Biyani proposes running through the MVT framework, repeating these steps until you’ve learned enough to de-risk your biggest hypotheses. 

Find your value proposition. Determine the promise of your idea. Why would users want it? What are you promising them? 

List your risky assumptions. List the primary risks: why might this not work? What breaks your system? 

Test the atomic unit. Determine whether your idea actually works. Focus only on the “atomic unit” of what you plan to sell. For Google, the atomic unit is a search query. For Amazon, it’s ordering a book online. For Coinbase, it’s an easier way to buy and sell crypto. 

“When starting Maven, instead of trying to test everything with an MVP, I picked just one risk to start: Will consumers be satisfied with buying a cohort-based course for a significantly higher price point than video-based courses?” says Biyani. “As a test, I decided to run just one course. It was a hyper-narrow test that achieved the exact result I was looking for: The course had a 9/10 rating from its students and made over $150,000 in revenue in its first cohort.”

Perhaps there’s no interview question quite so dreaded as, “Where do you see yourself in five years?” Career planning is expected to be top-of-mind for folks, particularly when approaching a new job opportunity. But in reality, many often take a much more haphazard approach to plotting the points along their career roadmap.

So we turned to folks in the First Round community for the specific pieces of advice they’ve leaned on to take the driver’s seat in their own career planning. Molly Graham (of “give away your Legos” fame here on The Review) tactically recommends folks start with these four lists:

Things I love doing

Things I am exceptional at

Things I hate doing

Things I’m bad at 

The best version of your career is finding jobs that are in the Venn diagram between what you love doing and what you’re exceptional at. This may sound obvious, but oftentimes as you get more senior, the Venn diagram is often ‘things I’m exceptional at’ overlapping with ‘things I hate doing.’ You have to know yourself well enough to turn those jobs down, even when someone offers you the super sexy role full of things you hate doing. It’s a role that will bring out the worst in you,” says Graham. 

This isn’t a one-time list you make only in the early innings of your career. Every work experience you have — every project, every role — can add more data to the lists. Use these questions as your guide: 

What were my favorite things that I did this last quarter?

What moments or weeks did I feel at my best?

When did I feel like I could keep doing the same set of things over and over again and be happy? 

When did I feel drained or depleted?

When did I feel bored? 

At what moments did I feel like my worst self?

Photo of Minaa B.
Minaa B., psychotherapist and wellness coach

Self-care has taken center stage over the past couple of years, magnified all the more by the wave of isolation, stress and burnout caused by the pandemic. In one of our favorite pieces of the year, therapist Jessmina Archbold (publicly known as Minaa B.) challenged us to go deeper than the well-worn suggestions to indulge in a bubble bath or yoga session.

Self-care is seen as what you can buy yourself, not how you can work on yourself. In my view, self-care is deeper work — there’s a difference between engaging in self-soothing relief from a discomforting emotion, versus tackling the hard work to take care of yourself on a deeper level,” she says.

It’s also about matching the medicine to the moment. “If your body is feeling tight or you’re stressed, working out is a great option. But if you’re feeling depleted more on a social level, doing a workout video by yourself isn’t going to help,” she says.

Archbold offers a three-tiered self-care inventory system to break down the available options, ranging from immediately accessible to bigger investments of your finances, time, and energy. “If I feel dysregulated, I can do some deep breathing in the moment. But if I notice a pattern of often feel