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20+ Startup Founders on How to Make the Most of the Holiday Season

November 30, 2018

17 Min Read
Reading Time: 17 minutes

The end of the fourth quarter marks the start of the festive holiday season.

Do you know what that means? It’s crunchy, yet fun time for businesses.

Businesses take full advantage of this season. Almost all businesses – online and traditional included – examine the previous year, observe the mistakes they made, the successes they achieved, and their potential to expand. They plan the future year ahead, allocate budget for it, and take a break from all the business activities that had them embroiled.

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What You Will Get in This Article?

As a budding startup founder, or an entrepreneur looking to learn a few new things, this holiday survival guide will help you:

  • Define your future year with much more confidence
  • Plan and allocate budget for holidays
  • Find out what you can learn from the previous year
  • Plan for the upcoming holidays, and if you don’t have them already, add them to your calendar

We did a survey of some of the top startup founders to learn what they do during the holiday season; how they plan for the future year; and the most important question, how do they vent out.

Their responses will provide our readers with an insight into a lighter side of life and how these successful people tend to enjoy the holiday season.

Without any more ado, enjoy the read!

‘Improving Business Processes’ – Jens Jakob Andersen, Founder, Run Repeat


Jens Jakob Founder Run Repeat

Our lead generation websites generate organic phone calls. We experience a drop in phone calls during November and December, so we focus on family, travel, and improving processes during the end of the year season.

The Best Part of the past Year

The Holiday season is the best time to travel. For most of us, the Holiday season means less appreciated weather, and we tend to spend most of our time indoors. As I love the outdoors, I love to travel in October,

November, and December. Flights are at their cheapest, as long as you don’t get too close to Christmas.

Last year, I went to New Zealand, and as it’s on the southern part of the equator, the weather was amazing, and if you get there early (November or start December), there aren’t too many tourists and you can enjoy the natural wonders in peace and harmony.

Tips for Budding Entrepreneurs

Focus on family, travel, and improve processes during the last quarter of the year.

‘Parties and Celebrations’ – Iain Wang, Co-Founder, Classbento

Iain Wang-Classbento

We work hard to keep up with the increased demand. The Christmas week itself is usually quiet so I use that time to enjoy with family.

The Best Part of the past Year

Q4 is the busiest time of year for us. With the Christmas season comes lots of gifting, office parties, and other celebrations, which increase demand for the creative workshops on offer at Classbento.

Tips for Budding Entrepreneurs

Burnout is very common with founders, so it’s really important to take time away from work during the quieter times of the year and to just enjoy those simple moments. It’s also a nice time to catch up on some reading or to do something different (like travel, or maybe a creative workshop) to broaden perspectives and gain insights that you’d miss during the day to day of running a business.

‘A Proper Sum up’ – Alexander Sergeev, CEO & Founder, Hygger


I always prepare my company (Hygger) and all team members to meet. We finalize the whole year of our hard collaboration. Every new success and every new great project is the result of a complex work executed by all the staff.

It is more important for companies that are at a certain stage of their development like startup projects in IT industry, to pay more attention to projects like moms pay attention to their babies and keep them under their care.

The Best Part of the past Year

Except for the final general meeting, the other work at the end of the year is not very different from my daily routine. Within all my company, I continue working hard and doing everything for the company’s success in the future year and I truly believe it is a good tone for every self-respecting founder.

So that’s why it is important to mention every person involved in the company development and emphasize the contribution of every specialist.

Tips for Budding Entrepreneurs

I have a soft spot for holidays, especially the Christmas and New Year seasons. The end of the calendar year is the time for a proper summing up not only of the personal life but also of business development as well.

‘Vacation Trips’ – Oliver Laugsch, Co-founder, Welcome Beyond


It’s actually one of the busiest times of the year for us as people have to plan their next vacations over the holidays so we have to be active at Welcome Beyond.

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The Best Part of the past Year

November is still the pre-season for most accommodation businesses, so we use it to travel and do some location research, and at the same time, to get some sun while it’s dark and cold back home in Berlin.

Tips for Budding Entrepreneurs

I assume it depends on the type of business but, if possible, use it to recharge and plan the next year while you have some time to think.

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‘Reflecting On The Past’ – Tomer Aharon, Co-founder, Poptin

Tomer Aharon-Poptin

For me, Q4 is a time to reflect on the past. It is the time to be more with family and friends. From a business point of view, Black Friday and Cyber Monday are a great opportunity for us at Poptin, as a platform that helps website and e-commerce businesses increase sales with smart pop-ups, to get a high volume of new customers.

The Best Part of the past Year

In December people save their money for Christmas, so we can take a step back and relax a bit from the shopping madness. Usually, at the end of the year, I try to take a vacation abroad and visit my wife’s family in Canada and Florida.

Tips for Budding Entrepreneurs

Other than taking a vacation from time to time, I’d advise entrepreneurs to reflect on their achievements from the past year, and celebrate all the small victories. As entrepreneurs, we always tend to be hard on ourselves and use any free minute we have to work, but we have to remember that we do this for the family and also a relaxed mind can lead to better ideas and productivity.

‘Choosing Our Priorities’ – Santiago Valdés M., Co-founder, Vestua


We keep doing almost the same as we do always i.e. choosing our priorities depending on our current status. In particular, we at Vestua are focusing on increasing our inventory due to the nature of our business, but we are not 100 percent focused on Christmas sales. Actually, it’s not that much of a peak for us, so we keep doing things almost the same as always.

The Best Part of the past Year

Q4 is a great sales season, mainly because of Christmas and other sales like Black Friday and Cyber Monday

Tips for Budding Entrepreneurs

If you are betting 30 percent of your sales, just put everything you have this month and sell as much as you can. On those special days, just try to relax, enjoy with family and have a nice holiday. We know the to-do list is never-ending, so just take it easy for some hours and enjoy it.

‘Great time for discounts’ – Alejandro Rioja, Founder, Flux Ventures


It’s an exciting time for company founders because we get to think about the goals for the following year and how to best strategize them. The holidays might not be the best time to squeeze in a deal because things tend to move slower with the long weekends and breaks. As an e-commerce company (Flux Ventures) selling a portable charger, the holiday season represents our largest influx of revenue of the year. This is a great time to run discounts, special promotions and to connect with customers.

The Best Part of the past Year

On the days leading up to Black Friday and Christmas, I work hard on our marketing campaigns to make sure we meet our Q4 revenue goals. After that, I spend a few days from Christmas to New Years with my family and friends back in Bolivia. This is the only time I get to travel home, so I like to cherish it. I try to make sure things are running smoothly without me so that I can take some time off and truly relax. I also use this time to rap a few songs.

Tips for Budding Entrepreneurs

I think there’s a fine balance between just working all day and having some time off to enjoy how far you’ve come. I suggest entrepreneurs to start planning for the holiday season a few months in advance so that they can take a short and much-needed break around Christmas to enjoy some quality time with their loved ones. At the end of the day, more revenue won’t make you happy. Instead, a great time with friends and family definitely will.

‘Create Fresh Content, Update Resources’ – Gaby Roman, Founder, No Code Apps

I’ve read that around 30 percent of business sales tend to happen between November and December or rather during Black Friday season and Christmas.

The Best Part of the past Year

I spend the Q4 working to focus on business growth. People are happier to spend money during those times because they’re aware of brands. Even if I’m not running a big sale that still means I can grow my audience and start nurturing them right away.

Tips for Budding Entrepreneurs

Focus time on creating fresh and often free content, update existing resources, give more time to outreach activities, and implement sales plans for November and December.

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‘Pause and look around’ – Maksym Podsolonko, Founder, Eazyplan


The holiday season is different from the rest of the year. All other trips and vacations through the year are mostly focused on occasional family and common activities. Winter is my favorite season and these holidays are always special.

The Best Part of the past Year

It all starts with Christmas decorations of the house that we do together with kids. We always plan a long road trip for this period that combines shopping in a large shopping village, sightseeing in some new cities that we haven’t visited before, and skiing. Every member of the family is looking forward to one of the elements most, but there’s something for each of us. And this is the only time of the year when I completely disconnect from all my emails, messengers and project management apps for several days in a row to focus on my close ones.

Tips for Budding Entrepreneurs

While each person is different, it is crucial to stay connected with your close ones and friends. Being an entrepreneur, we often lose track of time and get swamped by our tasks. The festive season is a perfect moment to pause and look around, enjoy simple pleasures with your family and friends, clear our heads. Besides, if we will all do it during the same period, we will not face too many unread emails and notes in our inboxes when we come back to work.

‘Relax after a stressful year’ – David Kovalevski, Founder, Waka Coffee

David Kovalevski

The holiday season is the biggest time for online coffee products like ours (Waka Coffee), so I definitely look for this time of the year.

The Best Part of the past Year

People were literally buying our boxes as gifts starting from early October. Knowing that I can’t imagine myself leaving the company for a vacation anytime until the end of the year.

This will be my first holiday season as a founder, and I believe I will have to work even harder than my regular schedule to generate as many sales as we can.

I do have a short vacation planned, but right at the end of the year so I hope it will be mostly for relaxing after a stressful (and rewarding) time.

Tips for Budding Entrepreneurs

Work harder than your regular schedule to generate as many sales as you can.

‘Share Revenue with the Team’ – Eric Hobbs, Founder, Technology Associates

During the last quarter of the year, people want to enjoy the holidays. But as a business owner, I also understand that businesses want to tap into the additional revenue offered by holiday sales opportunities. This is especially evident in what I do. I built a company on the premise that businesses won’t have to worry about IT because we can take care of everything for them. But while we’re solving their needs so they can enjoy the holidays, I have to find ways to keep my team motivated.

The Best Part of the past Year

Through the years I’ve been in business, I’ve learned that it’s best to find a good balance between work and leisure. For added motivation, I try to provide additional incentives for my team during one of our busiest times of the year. I make sure to share my year-end objectives with them and get them onboard. I make it a point to be transparent—if I want to leverage on the additional revenue, I let my team know and inform them that whatever is gained through our additional efforts will be shared across the board. When everyone is on the same page, it becomes so much easier to work towards and achieve a concrete year-end goal, and then have your efforts culminate with a much-deserved holiday or celebration.

Tips for Budding Entrepreneurs

My advice for young entrepreneurs is the same. To share the benefits across the board because this way you can win their trust and keep them motivated.

‘Remote Working’ – Alexia Bregman, Founder, Vuka Sparkling Energy Drinks


Over the last 10 years in business, I and my husband have realized that we should really embrace the benefits of being a founder and entrepreneur.

While in the early days we would slog all through the year. But for the past couple of years, we have really relished in the freedom that being a business owner can give – especially, as a reward for the hard work we put in all through the year.

The Best Part of the past Year

The benefits of technology mean that we can still monitor our business (Vuka) from anywhere in the world. And so every December we pack up our three kids and adventure to somewhere in the world. This year we’ll be going back to our home country of South Africa, but previous trips have included Australia and our all-time favorite, a catamaran around the Caribbean.

‘Work & Plan’ – Ali Payani, Co-founder, LookinLA


The Best Part of the past Year

I had important meetings at LookinLA during Christmas in 2017. When I went to San Francisco for a meeting, the CEO opened the door for me and all his employees were on holiday break!

So it’s mostly like that only CEOs and entrepreneurs don’t take a break, during new years eve, and other holiday seasons.

Tips for Budding Entrepreneurs

Spend most of the time in the office working and planning. I see this time of the year as an opportunity to take my companies forward. Especially in strategic planning, I will go out with friends or fellow entrepreneurs for a drink or dinner, but definitely, I can not take a break for more than one day!

I think most successful entrepreneurs do not take a long break, but for those who feel exhausted and tired, I recommend to take on a day trip to relax and start fresh on the next day. This is a holiday season that most employees are taking a break so you have more time to spend on planning for Q1 & Q2. Also, analyze the past performance of your company.

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‘Reset Yourself for the New Year’ – MaryBeth Hyland, Founder, SparkVision


As a founder, I have found the holiday season to be particularly essential in intentionally reflecting and resetting for the year to come. Naturally, it’s a period where business (Spark Vision) is slower because most of my clients are taking off during that time.

So it’s the perfect window to be intentional about looking at the year’s highs and lows to further learn how any wounds could become wisdom.

Tips for Budding Entrepreneurs

My best tip for building entrepreneurs would be to carve out time to go on a retreat and do this reflection to better prepare yourself for the new year. Personally, I go to a lake house with several other female business owners and we do a combination of group sharing and independent planning. We always come back together to get feedback and support on how to execute the essential next steps.

It’s wonderful to have both times independently but also the warmth of company – knowing that you’re not alone as a founder, even though it can often feel that way. So grab some fellow business owners, find a calming space, and honor the past year to align the next one!

‘Well-deserved wind-down time’ – Sabry Macher, Founder, 3dfyme


This is a busy time of the year for us. People are looking for that very special gift that will create a lasting memory with their loved ones. This is when one of our services will come in handy. Our Mini-Yous and Mini-Buddies are a wonderful way of capturing special moments forever in gorgeous, colorful 3D.

The Best Part of the past Year

As a startup (3dfyme) working hard, with relentless and laser focus is the default mode of operation. We are all hoping for a bit of well deserved wind-down time between XMAS and New Year. We are in the final stages of completing a major customer project and have just launched our new site in Indonesia as well. So, YES, it’s been pretty intense but rewarding as well for the team.

Tips for Budding Entrepreneurs

Depending on where you are on your entrepreneurial journey, you should take the time to reflect on your achievements and show gratitude to all the people in your team, friends, and family who helped you get where you are.

‘Question your strategy’ – Kean Graham Founder, MonetizeMore


Despite traveling 12 months of the year while growing MonetizeMore, I always make a point to meet my family for Christmas. Last year, I convinced them to meet in Mexico rather than celebrate at home in freezing Canada.

The trip went so well, we decided to do it again in another part of Mexico. On day 1, we rented a car and traveled around each city of the area of Mexico while staying in Airbnb spaces.

The Best Part of the past Year

Christmas is a good opportunity for me to relax, enjoy quality time with my family and reflect on what has transpired over the past year. During this time of the year, I take the opportunity to question our strategy, reflect on the direction of the industry and make grandiose predictions for the next year. I tend to come across some important realizations or conjure up new ideas that affect the strategy of MonetizeMore in a positive way.

Tips for Budding Entrepreneurs

For many founders, it would be tough to completely take this time off. I recommend taking as much time as you can to relax, enjoy your family and friend time and reflect on what has transpired. When you get outside of your typical week-to-week, some big realizations become much clearer which could be worth its weight in gold. The holiday season is the best opportunity for this.

‘Turn off your cell phone’ – Will Craig, Managing Founder of LeaseFetcher


The holiday season is probably the only time of year that I really take a break from leading my company (LeaseFetcher). For a week, I delegate all of my responsibilities to my deputy. I turn off my work cell-phone, stop checking emails and catch up on some much-needed family time. I’m a keen cycler and hiker when I get the chance, so inevitably, I end up doing that among other things.

I’m very suspicious of entrepreneurs who say they don’t need a break – everyone needs a break sometimes, otherwise, you’ll get burnout and have to spend months doing

nothing to recover.

Tips for Budding Entrepreneurs

My top tip to budding entrepreneurs would be to always make time for breaks and vacations – your mental health will thank you in the long-term.

‘Time for self-reflection’ – Ketan Kapoor, co-founder, Mettl

Ketan Kapoor

Co-Founder Mettl

In my experience, I have found holidays to be the leanest part of the business year as most of our clients are closed. Since I know I can’t make the most of my time available for business prospects, I make the most of it for the personal front.

I let my hair down and enjoy thoroughly with my family for the entire two weeks, knowing it would be another complete year before I get to this point in time. It’s refreshing in the way that I remove all the complaints of my near and extended family members of not being available for the rest of the year.

I reflect on a lot of things – how far I have come, where I want to be in the next year and how all that I achieve in next year will take me a step closer to the future, and all those things I need to learn and unlearn.

Tips for Budding Entrepreneurs

A busy entrepreneur who has been busy around the year, can utilize this time of the year to meet the extended family or friends which you don’t get to see often because of the hustle and bustle of the business life.. Since you are free from any distraction, you can use the holiday time for self-reflection of what went right and wrong for your business. Moreover, leverage the time to think about the business strategies that you need to implement for the holistic organizational development.

‘Re-evaluate our direction and priorities’ – Fiona Adler, Founder, Actioned

christmas tree-fiona-adler

For me, the end of the year is the perfect time to step back from the business and re-evaluate our direction and priorities. To do this properly, we need to get some distance away from the business – perhaps physically away on holiday, or perhaps just allowing myself to be preoccupied with family and festivities for a few days. By switching the brain away from the business, you can actually come back with a lot more clarity of thought.

I also know that it’s good to talk about my business (Actioned) with family and friends. It’s tempting to think they won’t understand as they operate in very different spheres, but that’s exactly the point!

When your aunt asks you how something works or how you plan to do something, it gives you insight into the way other types of people think. Perhaps it’s the naive questions that will turn out to be illuminating, or it might be someone explaining how they operate in a different industry that can spark an idea.

The Best Part of the past Year

I like to spend a few days revising the business plan and mapping out the next few months. This starts with reconnecting with the vision statement and making sure this is still relevant and inspiring. Then I think forward and decide where I’d like the business to be 12 months from now.

How do I want it to look from the perspectives of customers, product, financials, processes, and people? Working backward from this, I think to write down all the big things that need to happen during the year, e.g. what new hires do we need to make, what markets do we need to enter, do we need to change our pricing, what product improvements need to be made, etc.

I’ll then create a roadmap which shows the key milestones month by month. Using this system, I can easily decide what the day-to-day priorities are for the business.

‘Finalize Budget for 2019’ – Reuben Yonatan, Founder, GetVOIP


While I appreciate family time like the rest of the year, I do have specific tasks at GetVOIP which I need to accomplish each Q4. Because we have already formulated next year’s plan of operations, Q4 is the time to start laying the foundation.

We use Q4 to:

  • Complete initial networking:

These connections will build project capacity, or facilitate exposure to prospects.

  • Build teams:

It’s time to form teams, layout and assign project briefs, and begin jointly road mapping how we will achieve our 2019 tasks.

  • Finalize 2019 budgets:

This may seem out of order, but after completing the above tasks, we will have a more accurate understanding of next year’s estimated operating costs.

‘Take a Break’ – Will Cannon, Founder, UpLead


It’s time to take a break from work and spend time with family and focus on what matters most – your loved ones.

Tips for Budding Entrepreneurs

Run some Black Friday and holiday promotions to drive growth during the holidays, but take time to enjoy your family and loved ones.

Final Word

That’s the whole list.

The holiday season doesn’t last long. Therefore, take advantage of the opportunities it has to offer to your startup. Do ensure to follow the pieces of advice offered in this holiday survival guide for startup founders, because soon enough you will be back to the grinding work.

We have tried to keep it as simple as we could have, by highlighting tips for aspiring entrepreneurs and future leaders.

Let’s know what do you do during the holiday season or what is your best tip to spend the holiday season for the startup founders.

Related Article: 20 Experts Share Their Best Tips for Bootstrapping a Business

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Arsalan Sajid

Arsalan, a Digital Marketer by profession, works as a Startup Community Manager at Cloudways. He loves all things entrepreneurial and wakes up every day with the desire to enable the dreams of aspiring entrepreneurs through his work!

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