Entrepreneurial Takeaways From 2020 to Guide Your Next Big Move Examining the unexpected and unprecedented challenges of the past year can show the path for a successful 2021.

For many of us, this has been the most unpredictable and difficult year of our lives. Only 11 months ago, we rang in the new year and new decade in a world that looked and felt far different and far more certain than the world we've experienced since — and it was hard to imagine at that time how vastly our lives would collectively change in just a short period of time.

Now though, as we look back on 2020 and our personal and collective experiences living through the COVID-19 pandemic, we have the ability to reflect on takeaways and better prepare ourselves mentally, personally and professionally for the challenges that may lie ahead. For as much as 2020 has taken from us — loved ones, social contact, daily routine and basic freedoms — it has also left us with invaluable lessons.

Here are my top entrepreneurial takeaways from my experience navigating the startup landscape this past year:

Plan for the unexpected

When we launched Punch List back in January, we were living in completely different circumstances — and while COVID-19 was clearly becoming widespread in parts of the world, it was almost unfathomable at the time to think that it would become a global pandemic that would halt life as we know it. But it did, and quickly. In the first week of February, I personally spoke to over 120 contractors interested in using Punch List on remodel projects. By the second week, demand was cut in half. And by the time 80% of the country was under some sort of stay at home order a week later, our adoption rate mirrored that grim reality. This is a pandemic unlike any that we've seen in our lifetimes, of a magnitude that we'd only seen (up until this year) on the silver screen.

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Looking back it seems surreal, like an all too realistic adaptation of the movie Contagion. The lesson is ingrained in each of us — this type of life-altering global situation is possible and as entrepreneurs, we need to be prepared for anything. We quickly adapted to make sure our team was set up for successful remote work. That meant providing everyone with a small stipend to make their homes more "work friendly" - the wrong equipment can result in everything from muscle fatigue to ergonomic injury.

During periods where construction activity and customer acquisition were down due to increased restrictions, our team focused on what we could control — our product and user experience — knowing that once restrictions were lifted, we would be a vital tool to enable contractors to safely, efficiently and effectively complete remodels with homeowners while maintaining social distance. We even designed a brand new app, Specialist, from scratch. Using Specialist, any expert (including contractors + handymen, plumbers, personal trainers, hairstylists and cosmetologists, chefs, etc) could monetize their time by connecting to their customers over video chat from home to help solve a problem, learn a new skill, or accomplish a task. The app combined contact sharing & appointment scheduling, point-and-record video calls, and automatic digital payments to empower small businesses to safely, simply, and transparently interact with customers face-to-face. The launch was such a success that we sold Specialist to a competitor just a week after launching it and four weeks after beginning development.

I'm extremely proud of the team for recognizing the problem, developing a quick solution, and building a product that could help millions of people affected by the pandemic. Now as we look to 2021 with our focus solely on Punch List, we are aware that we need to plan for the expected, while being ready to adapt to whatever is thrown at us.

Build a culture of trust

With remote work becoming the norm amidst the pandemic, it's more important than ever to lead with trust. Have faith in your employees' abilities and allow them the space and freedom to create a work environment, and even schedule, that allows for maximum productivity — especially in such strange times when it's important to account for differences in everyone's situation. Avoid micromanaging as much as possible and build a connection to your company culture through trust. To combat isolation, my brilliant Co-founder, Andy Vella, suggested scheduling a 1 hour "Water Cooler" calendar entry each day. During WC, the entire company gathers together on video to chat about any topic, work-related or not, that's relevant that day. Not only does this combat isolation, but it results in real human connection when we couldn't be farther apart.

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Promote financial wellness

During a period where so many companies have been forced to make difficult decisions regarding employment and record numbers of Americans have been furloughed or laid off, it's more important than ever for organizations to promote the financial wellness of employees. Look ahead and offer resources to help educate your employees to help them save, invest and plan wisely to better account for periods of uncertainty and change ahead. Even though we recently moved into a beautiful office in San Francisco's financial district, Andy and I made the difficult decision to sublease the space and make Punch List a remote-first company. The monthly rent, combined with reduced usage, no longer made it a smart financial investment for the company. Instead, we shifted some of those funds to the employees in the form of home office stipends and company-funded internet/phone plans.

Always have a safety net

There's no question that 2020 has been a financial catastrophe for many companies, as businesses were sent reeling by a pandemic that forced businesses to shut down for prolonged periods, spurred unemployment and seriously impacted consumer spending. The situation highlights the importance of always working to build a safety net, as an entrepreneur, to hold your business above water during prolonged downturns.

Make sure to fully understand and consider your overhead costs and work towards building a cash safety net that could cover those costs for six to twelve months in the event of a disaster. And, when needed, cut your losses to avoid ongoing expenses (bye-bye office!)

Don't hesitate to adapt

This year, in the face of unprecedented challenges, many typical business strategies have proven ineffective. It's important to not remain fixed in one way of thinking or seeing a situation, and instead be able to efficiently adapt to different circumstances and scenarios. Your business may need to restructure operations quickly, as many did this year facing the pandemic - being able to do so quickly, and without hesitation, is imperative to survival. If you told me that we would have built Specialist, a video app to help experts make extra money (by the session or by the minute) from the safety of their own home, during a global pandemic in 2020, I would have laughed at you. However, with remodeling projects paused, our team had to refocus on where the need was most - and I couldn't be prouder of the results.

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Invest time in relationships

People are important, and investing time in people and in relationships is of paramount importance for entrepreneurs. Whether face-to-face contact is possible or not, make sure to dedicate time to connect with people - your employees, partners, customers, investors and fellow entrepreneurs. Make a goal of connecting with or checking in with a few people each day. It could be during planned sessions or during random Slack/Zoom calls, just as long as you take time for those important to you.

Take pride in building those relationships and leverage them, and the knowledge you gain from them, to help your business flourish. 2021 will be here soon enough!