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

December 3, 2019

11 Min Read
Holiday season for founders
Reading Time: 11 minutes

December marks the beginning of the festive holiday season. It’s time to relax and have fun. It’s time to connect with family and friends. It’s time to self-reflect on personal strengths and weaknesses and formulate resolutions for the upcoming year. 

For businesses, It’s a hectic, yet fun time.

It’s time for businesses to reassess their achievements and failures during the last year. The holiday season also provides a great opportunity for businesses to redesign the strategies and plans for the next year.

What You Will Get in This Article?

As a budding startup founder, or an entrepreneur looking to learn a few new things, this blog will motivate you to have a life you dream of, without compromising on your dream of becoming a successful business entity.

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.

We surveyed some of the top startup founders to learn what they do during the holiday season; how they plan for the future year; and. What activities they do to keep themselves relaxed.

Without any more ado, enjoy the read!

‘Get Time to Relax’ – Kean Graham, CEO & Founder, MonetizeMore

Kean Graham

Kean Graham, CEO & Founder, MonetizeMore

Despite traveling 12 months of the year while growing MonetizeMore, I always make a point to meet my family for Christmas.This holiday season I will be spending time with my family in Victoria, BC, Canada. It will be a great opportunity to unwind, spend some quality time with them. I plan to read a few books, practice golf and enjoy home cooking! The relaxing two weeks will be just what I need to begin 2020 with greater clarity and motivation.

The Best Part of the Year

For many founders, it would be tough to completely take time off. I recommend taking as much time as you can to relax, enjoy with your family and friends, and reflect on what has transpired.

Tips for Budding Entrepreneurs

When you get outside of your typical week-to-week schedule, some big realizations reveal themselves that could be worth the weight of gold.

‘Focus on Improving Processes’ – Jens Jakob Andersen, Founder, RunRepeat

Jens Jakob Andersen, Founder, Run Repeat

Jens Jakob Andersen, Founder, RunRepeat

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 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 during October.

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

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

Tips for Budding Entrepreneurs

Focus on having quality time with family, travel, and improve processes during the last quarter of the year.

Learn from The Best List of Advice for Young Entrepreneurs

‘Work hard to meet increased demand’ – Iain Wang, Co-Founder, Classbento

Iain Wang Cofounder Classbento

Iain Wang, Co-Founder, Classbento

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

The Best Part of the Year

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

Tips for Budding Entrepreneurs

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

30% Sales Occur In Q4’ – Gaby Roman, Founder, No Code Apps

Gaby Roman No Code Apps

Gaby Roman, Founder, No Code Apps

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

The Best Part of the Year

I spend Q4 to improve 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, it still means I can grow my audience and start nurturing them the right way.

Tips for Budding Entrepreneurs

  • Focus on creating fresh and often free content
  • Update existing resources
  • Give more time to outreach activities
  • Implement sales plans for November and December.

‘Give Thanks to Clients’ – Brenda Della Casa, Founder, BDC Digital Media

Brenda BDC Digital

Brenda Della Casa, Founder, BDC Digital Media

December is a slow month in my business (BDC Digital Media) so I spend the season giving thanks to my clients and focusing on building relationships.

A handwritten card goes a long way as does a small gift, such as a bottle of bubbly or even homemade cookies.

I also begin planning my content for the following year in order to get at least three months head start. This includes planning an editorial calendar, pitching press releases, and setting goals for the quarter ahead.

The Best Part of the Year

I truly believe that a mind is like a body and needs rest in order to grow stronger, so, during the last month of the year, I focus on my family and restore myself through personal connections and just have some fun. It’s only once a year that I get that delicious week where I can forget what day it is and that’s a glorious way to re-energize before the New Year.

‘Avoid Working on Holidays’ – Ben Mirecki, Founder, CarPages

Ben Mireck, Founder, FoCarpages

Ben Mirecki, Founder, CarPages

Founders are always possessive over businesses. As a result, there is always a temptation to work on Christmas and other holidays to maximize success. Of course, during the holiday season, there may be a variety of new issues, which require you to be on call. However, I don’t agree with an intense, last-minute push for sales or anything like that — especially not in the ecommerce industry. I like to rest during the holidays, without the lingering voice in my head saying “make more sales”.

The Best Part of the Year

Preparation for the holiday season at CarPages starts months in advance when we begin to alter our digital marketing strategy to focus on targeting relevant audiences or promoting different seasonal products. This preparation also includes ensuring that the business has the capacity to respond to seasonal changes. A few things we consider: Do we have enough customer service employees? Is there always a developer on-hand to respond to site-wide issues? And many other issues like that.

Tips for Budding Entrepreneurs

My aim has always been to have the right systems in place so that operations run smoothly and I can spend precious time relaxing with friends and family with the full awareness that most things are in order.

‘Take vacation’ – Matthew Ross, Co-founder, The Slumber Yard

Matthew Ross, Co-founder, The Slumber Yard

Matthew Ross, Co-founder, The Slumber Yard

I always take a two-week vacation every year over Christmas and New Year to recharge and refocus my mind after a long 12-month period.

The Best Part of the Year

I choose this specific time period specifically because it’s a slow time of the year and our employees are on holiday.  As such, I feel it’s an optimal time to relax since I’m not needed as much to answer questions and run the day-to-day operations. For example, last year I went to Thailand because I wanted a beach vacation that offered a different type of culture. After a long, hard year, I thought it might be nice to get away from the typical American lifestyle for a little while. This year I’m heading off to New Zealand.

‘Work Long Days On Weekends’ – Calloway Cook, Founder, Illuminate Labs

Calloway Cook, Founder, Illuminate Labs

Calloway Cook, Founder, Illuminate Labs

Since my business was just incorporated earlier this year, I have to work rather than go on vacation during the holiday season. I work remotely on my ecommerce company. And, I don’t get as much done when I’m out of town. I have figured out that I can get a competitive advantage on other startups by working for long hours over the holiday season.

The Best Part of the Year

The fourth quarter is when it gets the busiest for an ecommerce business as everyone is shopping for the holidays. And, I have too many responsibilities to manage before the year ends.

‘Retrospection’ – Dmytro Okunyev, Founder, Chanty

Dmytro Okunyev, Founder, Chanty

Dmytro Okunyev, Founder, Chanty

In the fourth quarter, I look back at what we’ve done in the previous months. What goals we were able to achieve and where we failed. Instead of blaming ourselves for not meeting our desired goals, we do something different – we double down on what works. For example, we did a really good job with the marketing in 2019, so we use fourth-quarter to maximize our marketing efforts and end 2019 with a bang.

The Best Part of the Year

At the beginning of the New Year, we sit down and reset our goals for the year ahead, knowing what worked in the year before and what needs to be improved further.

‘Family Comes First!’ – Kerry Mellin, Founder,

 Kerry Mellin, Founder,

Kerry Mellin, Founder,

Holidays are fun for founders like myself, who are running a family-owned ecommerce business. Marketing and selling products during gift-giving seasons will have you work overtime to advertise, secure listings in gift blogs and newsletters, arrange partnerships for giveaways, do holiday collaborations with nonprofits, attend special events and seasonal expos, and send all the promotional items and gifts that you want to offer to your customers to encourage sales – in advance – for the season.

On the other hand, running our family business, with three sisters, everyone knows that family comes first.  Making time for personal shopping, and taking time or days off for preparations, is encouraged.

Tips for Budding Entrepreneurs

Since we are working hard for our families, so we make it our motto to always remember that life is happening while you are planning something else, so pen in your time with family.

‘Plan for the future’ – Chane Steiner, CEO, Crediful

Chane Steiner, CEO, Crediful

Chane Steiner, CEO, Crediful

The last part of the year should be about wrapping up and making a list.

The Best Part of the Year

Figure out what you did right this past year and figure out what you need to improve on, then make a plan for the upcoming year to do it better. You should always strive to improve.

Tips for Budding Entrepreneurs

I think everyone should be able to have some vacation time and some unwind time, so if you can front-load your work year so that you have time to travel and relax, all the better. But if you do nothing else, you should at least take stock of what you’ve been doing for this past year and plan for the future to come.

‘Hows & Whys’ – Brandon Amoroso, Founder electrIQ Marketing

Brandon Amoroso, Founder electrIQ marketing

Brandon Amoroso, Founder electrIQ Marketing

During the holiday season, I focus on how we are going to execute what we are going to execute in Q1.

The Best Part of the Year

As an agency, most of our prospect companies focus on execution in Q4, so we have tons of follow-ups and proposals coming in Q1 that we need to prepare for. In addition, it’s important to create a strategy for our clients on Q1 initiatives and 2020 outlook as a whole. There’s typically a lull in consumer shopping after the Black Friday/Holiday craze. But at the same time, it is important that we spend some time out of the office with family and friends.

‘Reflect on the Past’ – Shaun Savage, CEO, GoShare

Shaun Savage, CEO, GoShare

Shaun Savage, CEO, GoShare

The end of Q4 is all about reflecting on the past year, spending time with coworkers, and planning for the next year.

The BIG question: Did we hit our stated goals for the year?

If so, all the more reason to celebrate it.

If not, why did we fall short?

It’s also a good time to plan for the upcoming year. I like to review our strategy, budget, and create new annual goals. This year, I’m taking more time off than usual to spend with my daughter, Vivian, and the rest of my family.

‘Take a Break’ – Saurabh Jindal, Founder, Talk Travel

Saurabh Jindal, Founder, Talk Travel

Saurabh Jindal, Founder, Talk Travel

As a startup founder, I try to manage vacations and work. During the holidays, I focus on my work. At the same time, I love to spend time with my family.

Since I run an internet-based business, I can work without location constraints and also coordinate with my team through Slack or Skype.

Before vacations, I make a detailed plan of action for my whole team and assign duties. I look at their performance reports at the end of the day. This makes sure that the business is running smoothly while I am away.

In case there is something urgent that needs my immediate attention, I am always there – something which my family also accepts and agrees to. So, it is kind of a balance between work and vacation, which I try to achieve with the support of my teammates and family members.

‘Rest and Recharge’ – Stefan Chekanov, CEO, Brosix

Stefan Chekanov, CEO, Brosix-20191204-185206

Stefan Chekanov, CEO, Brosix

I’ve always believed that to lead, you need to be your best self. That means you must be able to rest and recharge, which is why I take time off for one of my passions during the holidays – skiing.

I typically head to the Alps. It’s a pleasant experience as I spend time reflecting on the past year, I tend to look forward to the upcoming year.  For me, changing my surroundings is a great way to provoke deep reflection and fresh thinking. Some of my best insights come to me while looking at the beautiful scenery.

‘Working Remotely’ – Antti Alatalo, Co-Founder, Cash Cow

Antti Alatalo, Co-Founder, Cash Cow

Antti Alatalo, Co-Founder, Cash Cow

Working remotely while enjoying my time is how I spend the holiday season. I was born in Northern Finland, but for the last four years, I have lived in Malta. The weather in Malta is beautiful, and it is a hub for the gaming industry. The slogan of Malta is, ‘enjoy 300 days of sunshine’. The remaining 64 days are quite harsh. It’s rainy, humid and not pleasant at all. Malta is a small island unless it’s sunny there isn’t much to do.

The Best Part of the Year

The holiday season is not the busiest for our business. It slows down a bit from the B2B perspective. I love to travel to some foreign countries.

Tips for Budding Entrepreneurs

During the holiday season, I don’t work full-days. Instead, I keep a check on my email, and some other issues, that might require my attention. I usually work between 2-4 hours a day, do some sightseeing, eat great food and train in Brazilian Jiu-Jitsu.

One of my favorite things to do abroad is to visit local Jiu-Jitsu clubs. I like to combine working on holidays. Moreover, I enjoy the flexibility that I have been a business owner.

‘Decompress & Ramp Up’ – Kristin Marquet, Founder, &

Kristin Marquet, Founder, &

I usually spend the first three months of Q4 working on plans for each brand for the following year. December is for family and vacation.

The Best Part of the Year

For me, December is a BIG month because it’s my birthday, Hanukkah, and Christmas. I like to use the month as a way to decompress and ramp up for the new year.

‘Busiest Time Of Year’ – Angela Rucci, CEO, Tego

Angela Rucci, CEO, Tego

Angela Rucci, CEO, Tego

My company is focused on tracking and safety, so this time of the year is the busiest for us. We launch a new product every quarter, but the Q4 product is the most popular one.

The Best Part of the Year

I  spend most of November and December marketing our products and attending trade shows. I do take a few days off for Christmas and Thanksgiving. Since we are a startup, we enjoy the hustle. Once our company matures, we will have a set routine.

Final Words

The holiday season doesn’t last long. Therefore, take advantage of the opportunities it has to offer. Follow the words of wisdom offered by startup owners so that you can take charge of your startup business and grow it with minimum hassles.

Let’s know what are you upto during the holiday season. Also, share some of your best tips for startup owners on how to spend the holiday season. 

Share your opinion in the comment section. COMMENT NOW

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Arsalan Sajid

Arsalan, a Digital Marketer by profession, works as a Startups and Digital Agencies 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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