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10 Entrepreneurs Give Their Predictions of What 2021 May Bring


Brian Parks, Bigfoot Capital

Continue focusing on what you can control – your own and your team’s effort, focus and execution while recognizing we’re living in crazy times.

While the “traditional” workplace has changed (potentially forever), our professional endeavors can remain a source of inspiration and actually bring some certainty and comfort in these crazy times when so much in the outside world may currently feel (and actually is) beyond our control.

Heather Margolis, Spark Your Channel

I’ve always loved the New Year. It’s a great time to reflect and plan for the future. 2020 has certainly come with a lot of baggage that I’d like it to leave with. I think we’re all going through something right now and I’ve certainly struggled this year. I’m looking forward to 2021 even if it still means not seeing friends or family in person just yet. My plan to start the year off positively is to give my entire team the last week of 2020 off. We could all use this time to relax and truly unplug. It’s a great time to break out a notebook (I know, not environmentally friendly but sometimes I just need to write) and map out a plan for the future professionally and personally. What does success look like? What is standing in your way and what steps can you take to get closer to that goal? I also plan to get back into meditation. I’m horrible at it, can’t sit still, but I see a difference in my productivity, my personal interactions, and my overall happiness when I tune into Headspace or something similar at least once a day.

Danielle Owen Whitford, Pioneera

To start 2021 with a positive can do mindset, I’ll make sure I take a proper break over the Xmas season. I know as founders we’re supposed to work 24/7, but if I don’t have a break I’ll be less productive, less tolerant and less creative. I have also mandated everyone take a break, so they’re replenished too. Before we take a break I’ll do some forward planning with my team so we’re all on the same page for 2021 and then we can start strong. I expect the start of 2021 to be the same as 2020 and we may see some change towards the end of the year when vaccine’s start to become widely safe and available. All I know is that I’ll roll with whatever comes!!

Chris Motley, Mentor Spaces

“We can all agree that 2020 will go down as one of the worst years of our lifetime for a variety of reasons. But while the year has been tough there is much to be optimistic for in 2021. Historically, some of the best innovations happen as a result of tough times. As a child growing up in the church, I remember more than one minister telling us that a tea bag must go through some hot water before it becomes valuable. 2020 has been our “hot water” and has forced all of us to grow and innovate and really ask ourselves, ‘how do we want to show up in the world?’ I think we will see the fruits of that growth in 2021, which should, hopefully, put everyone in a positive mindset going into the year.”

Ben Dowling, IPInfo

It’s hard to predict what 2021 will bring, but I’m hoping it’ll be a calmer year with less uncertainty – and at the very least we’ll all be better equipped to deal with it. If nothing else, 2020 will make us stronger!

Andrew Rinaldi, Defendify

2021 marks the year where cybersecurity goes from a nice-to-have to a must-have, for every organization. Cybersecurity is a term the enterprise has known for a long time, but it’s really just making big waves with small and midsized-business these last couple of years. There is no doubt about it, the time is now. Take, for example, a handful of key realities: (1) A majority of employees are working from home forcing a new IT environment and even more security considerations. (2) Attacks are targeting more than just the big companies, some estimate half or more target small businesses as easy targets and conduits into larger enterprises. (3) Compliancy and regulation continue to increase across many industries, moving the conversation from best practice to legal requirement. (4) Many large customers now enforce cybersecurity standards that must be met by their vendors in order to keep current relationships and win new contracts. (5) While there remains a massive shortage of available security professionals—some report in the millions—companies like Defendify have streamlined cybersecurity tools and best practices to a point of affordability and accessibility for every size business. Three quick tips for taking on cybersecurity in 2021? First, get the right mindset: Like your health, cybersecurity is a posture, not a project. Next, put it in the budget, an actual cybersecurity line item. And finally… don’t wait a minute longer. Cybersecurity can be complicated and expensive, but it doesn’t have to be. There are lots of free resources and even some free tools on the market now that can help get things up and running in no time at all.

Gemma Sole, N.A.Bld & 19th Amendment

Raising? Don’t shy away from the big stuff. Be honest and upfront with how the Pandemic affected your business and let investors know your plans for a super 2021.

Rami Essaid, Finmark

After years of new tooling and  productivity improvement for every other department, 2021 will be the year that the CFO suite will reimagine their software stack. Accounting and finance teams will have access to new tools that improve productivity and visibility.

Ken Rapp, Blustream

The changing retail landscape means that 2021 will be the year that physical goods companies use their “products” to provide an even better customer experience after a sale, thereby exponentially improving the relationship between brands and their customers.”

Joe Raczka, York IE

As we enter into a new year and hopefully some level of normalcy, we should take some time to reflect on what went well and what didn’t go so well with our business. As we do that, we’ll want to take count of the complimentary pieces and people around us. It has never been more important to make sure you have the right team of supporters with diverse skill sets who will also challenge and make us better. That is true of the team at York IE but is also something we ask our Founders and Entrepreneurs to think about when bringing in new investors. At all stages, but especially the early stages of investment, it has never been more important for a founder to think deeply about what type of investor to bring around the table. There are all types- passive, active, spreadsheet junkies, transaction focused, governance only, etc. Focus on investors that have actually rolled up their sleeves in an operational capacity, understands your business model, and has perspective on your market and competitive landscape. Some of those elements can be teased out in a first meeting and can be more impactful than having a brand name legacy investor on the cap table at an early stage.

StartUp Mindset

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