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

Updated on December 3, 2021

16 Min Read

Are you ready for the most awaited time of the year? Yes! The festive holiday season is upon us! And we are extremely excited to simply retreat, be able to breathe, relax, and have all the fun we have been missing out on. It’s time to rekindle our connection and relationship with friends and family. It also gives us all the more reason to reflect on what we did throughout the year and be grateful for every success and milestone achieved! We can take more time to self-reflect to not only grow our strengths but also embrace our weaknesses to work on them and come out better the next year.

As a business owner, we know you have a lot to do! But don’t forget to cherish what you achieved and remember to make resolutions for what you want to achieve next year.

What’s In This Blog For Budding Startup Founders?

We didn’t want you to feel overwhelmed as a startup founder, because we understand the pressure you’re under, and your need to find the time to celebrate the holiday season this year.

This is why we approached 20+ entrepreneurs, who gave us advices and tips on how they spend the holiday season – enjoying and working, all in a light-hearted yet determined way.

We learned some exciting things that they do during the holiday season; the way they plan for the upcoming year; and the activities they do to celebrate the festive season and relax.

So, without further ado, let’s learn some valuable tips and advice on how to go about this holiday season as startup founders!

1. ‘Focus on Building Relationships’ – Charles Cridland, Co-Founder, YourParkingSpace

Charles Cridland

For me, holidays are the perfect time to give back and appreciate the people who keep my business running. So, I spend the holiday season giving thanks to my employees and clients. We send personalized e-cards to our clients signed by my team and me to show our best gratitude for staying with us. I also use holidays to engage my team personally, get to know them better, and inspire them. I believe that life is about helping people, building relationships, and doing something meaningful for others to make their lives better.

Tips for Budding Entrepreneurs

Send personalized e-cards to your clients signed by you and your team to show gratitude and build meaningful relationships.

2. ‘Plan Ahead and Improve Processes’ – Dan, CEO and Founder,


As a startup owner, it is my everyday job to bring value to my employees and customers alike. Whatever the time may be, my work as a business leader does not stop and the satisfaction of doing effective work continues to bring me joy.

Tips for Budding Entrepreneurs

The holidays can be stressful, to say the least. During this time, the practice that has worked the best for me is planning ahead of time. By that, I mean starting your planning in September. Getting a headstart is beneficial for you and your employees. it reduces pressure on your employees during the more critical days around the holidays and also helps bring more finesse to your work. Even throughout the work, I make sure my employees do not overwork themselves so that they can rest and also make the most of the holiday spirit.

As far as the work of a CEO goes, our job never really stops but relaxing is still a necessity to ensure a smooth workflow. I prefer spending quality family time and I ensure that by implementing a strictly no email policy on holidays so that everyone enjoys their off days, stress-free.

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

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3. ‘Take Practical Steps to Conclude the Year’ – David Reid, Sales Director, VEM Group

David Reid Photo

This year has been challenging for small businesses, and the holiday season adds to the mix. While holiday preparation may look different this year, there are practical steps small businesses can take to conclude the year and start the next.

Tips for Budding Entrepreneurs

  • Create a secure and memorable shopping experience for your customers – Customers should like shopping small, especially when compared to giant retail stores. We must create a unique and safe in-store expertise for individuals who prefer to purchase in person this year. Promote what clients can expect when buying with you, so they know it’s safe and fun.
  • Run specials as well as online-only specials – Holiday buyers like special offers. Customers are more likely to buy from you if they know they can get a discount or a bonus service. It’s a terrific approach to attract new consumers and reward old ones. Offering online promotions allows shoppers to support local companies without having to visit them physically. Because fewer people will be shopping in stores, extending your best bargains throughout the shopping season makes sense.
  • Utilize audience segmentation – Customer segmentation is the process of categorizing your users based on their attributes. It can be their location, gender, or anything else. Audience segmentation can benefit you in many ways. By segmenting your users, you can present content that they want to see. It increases conversions and sales.
  • Showcase your best-selling product: The audience prefers your best-selling items. Your customers buy them all year long, and if you put them in front of every visitor, they will at least try them on and possibly buy them. Your best sellers have proven themselves. Showing them frequently will increase holiday sales, conversions, etc.

4. ‘Be Prepared with a Backup Plan’ – Ed Leake, Founder, Adevolver


As a business owner, I think the busiest days in our career are during holidays; well, aside from other individual celebrations and festivities, Christmas and New Year celebrations hit differently. Work stress may be higher these pandemic years, but we all want what’s best for our customers.

Tips for Budding Entrepreneurs

In our company, since we work with google ads, we cope up with the new normal changes by strengthening the number of our reach and since holidays are the season where clients are overflowing we live by this number one tip, ALWAYS BE PREPARED AND HAVE A BACKUP PLAN, we are always planning ahead of time, what concept to work on, what more offers and services can be introduced and most importantly always have plan B when plan A fails to work. Since we discovered and applied that tip, our holidays were never the same; we worked smoothly and learned to prioritize tasks.

5. ‘Leverage Your Email Campaigns’ – Gerald Lombardo, Co-Founder, The Word Counter


My #1 piece of advice for startups during the holidays is to leverage your email campaigns. Most startups go big for the holiday season with digital advertising. And, in theory, they should: everyone is looking for gifts, customers are more reactive, and the holiday season is the highest-selling time of year.

However, digital advertising has a low conversion rate, is expensive, and requires constant A/B testing. If you’re looking for an effective and financially intelligent way to increase sales this holiday season, consider spending time prepping and optimizing your email marketing campaigns. As most email marketing has a typical success rate of well over 50%, it is by far the most effective way at garnering sales.

Tips for Budding Entrepreneurs

My recommendation: segment your email marketing list in three buckets: (1) returning customers, (2) old customers that have not purchased in the last 60 days, and (3) new subscribers that have yet to purchase. Create personalized messaging around each bucket, and give discounts + incentives to each.

With email marketing, you can optimize your holiday sales at a fraction of the cost of digital ads.

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6. ‘Take Out Time to Rest and Recharge’ – Jon Bennion, CEO, Online Marketing Gurus

Jon Bennion

The end of the year is the optimal time to relax, so I always take a vacation over Christmas to recharge after a long 12-month period. It’s an opportunity to spend quality time with my family and friends and reflect on what has happened so that I can begin a new year with greater clarity and motivation. With the right system in place, every startup founder can take time off to relax during holidays and have the full awareness that all operations run smoothly and most things are OK.

Tips for Budding Entrepreneurs

Have the right system in place so that work processes are running as per the norm while you make the most of the holiday season.

7. ‘Create Your Social Commerce Stores’ – Lauren Petrullo, CEO and Founder, Mongoose Media

Lauren Milan

Create and optimize your social commerce stores. 10000%. It’s the best way to leverage what you’ve already created for your online store into an ecosystem with buyers and little competition. There are millions of Shopify stores in various niches and only hundreds of thousands of those same stores with Facebook Shops and even fewer numbers represented that are optimized for social shoppers. There is very little competition right now.

Tips for Budding Entrepreneurs

Some of the biggest brands that you can think of that are doing hundreds of thousands of dollars in ad spend, have not set up these social commerce shops. I am telling you, there is no competition right now among social commerce. It’s shocking. Now is the time to take advantage. Startup founders need to create social commerce stores immediately.

8. ‘Relinquish Control’ – James Harford Tyrer, Serial Entrepreneur and Founder, Cudoni


I think it’s a real badge of honor to walk into a room and be the stupidest person because what is the point of hiring a CTO, a web developer or a CMO or any of these other people if you believe you can do the job better than them? I think it’s understanding that there are people out there who have got specialist skillsets and then giving them the autonomy to tell you what they need to do and allowing that culture to be embodied throughout the organization.

Tips for Budding Entrepreneurs

My physical well-being suffered when I first started because you put everything into the business. I think as the business matures, you have an obligation to your staff to look after yourself, especially during the holiday season. For me, it’s about looking after your mental well-being by putting the right mentor and advisors around you who have been on the same journey. Having the right support mechanisms in place is how you look after yourself. I’m told I need to take more holidays, I think that’s where the pasty white skin comes in and I probably need some sunshine. But I’m doing a little bit more of the reading, the giving back. I even do some exercise these days but I really think mental wellbeing trumps all else.

9. ‘Do Not Bring Your Work Home’ – Tyler Garns, CEO and Founder, Box Out Marketing


Do not bring your work home. The holiday season is the busiest season for all businesses, and as a CEO, 24 hours might not be enough. Hence, we tend to bring our work-related activities at home, which will not be beneficial for us. Our home should be our haven where we can relax and be stress-free. It should be a place where we can rest our minds and bodies to face another demanding workday. When our bodies aren’t well-rested, our productivity and efficiency tend to be lessened, affecting the people around us.

Tips for Budding Entrepreneurs

Ensure that when it’s your resting time, REST. You might be losing more money if your body gives up and is sick rather than skipping some work-related task to rest.

10. ‘Use the Time Appropriately!’ – Tudor Armand Ciuleanu, CEO and Founder, RebelDot

Tudor Armand Ciuleanu

The lead-up, during and after the holiday season, is business as usual for companies like RebelDot. At this time of the year, you should have all your features operating on all cylinders and you shouldn’t be making too many tweaks in the days leading up to the holiday season – and during.

Tips for Budding Entrepreneurs

For me, the most important thing to do during the holiday season is to recharge, refocus, re-energize, and prepare for when things pick up again. There’s no sense in dragging yourself down during a time where other people’s minds are elsewhere and they might not be acting normally as consumers.

Bottom line: take some time to refresh and focus on after the holiday season in order to succeed in the long-term, not just during a time that can be difficult to crack.

11. ‘Meditate and Reflect on Accomplishments and Goals’ – Thomas Jepsen, CEO, Passion Plans

Thomas Jepsen

My main thing during holidays is a lot of guided meditation. I’ve been at it for 3 years now, and make it something I do whenever there’s a holiday coming around. There’s nothing better than really returning after 2 hours of meditation. It is a special, rejuvenating feeling.

Tips for Budding Entrepreneurs

Holidays are the time when I take some time to really reflect on my accomplishments and personal goals. I’ll write down when I am looking to achieve in the year to come, and what actions I am taking to make it happen.

12. ‘Maximize Holiday Season Through Customer Relationship’ – Sonya Schwartz, Founder, Her Norm

Sonya Schwartz

As a founder, I spend my time giving to my customer or client and start focusing on creating connections because the Christmas season is a slow month in my business, starting in November and ending in December.

Tips for Budding Entrepreneurs

To create trust with them, it will be great to maximize it by appreciating them through handwritten cards, little presents, and even handcrafted items. Even during this holiday season, when having a major sale, you must spend time considering methods to boost business development. To keep you calm, you must keep your plans simple by thinking about your goals for the coming year, new methods, and ways to enhance your goods. But, ultimately, I believe the most essential piece of advice I could give you for this holiday season, not just for yourself but also for your business, is to give yourself time to grow stronger in preparation for the new year.

13. ‘Review and Set Targets’ – Rahul Mohanachandran, Founder, Kasera

Rahul Mohanachandran

A regular activity I do during the holiday season is to take a break for 2 weeks and out of the 2 weeks use a day to review my goals from the previous year and set the goal for next year.

Tips for Budding Entrepreneurs

I try doing this from not my regular setting like home or office to give me a different perspective and scenery. I only do this once a year and I try to be ambitious with it as well and try not to factor in failure. This will be written down in my notepad and I make sure I share it with people who are close to me so I commit to the goals and hold myself accountable.

14. ‘Balance Between Your Family and Business’ – Melanie Hanson, CEO, EducationData Loan Finance

Melanie Hanson

If you work for a startup, you’re probably used to rarely seeing your family, but especially around that first truly busy holiday season, missing time with your family and friends can create a lot of friction if you don’t take the time to prepare them for it beforehand. The last thing you need when you’re trying to get your brand new business in the black for the first time is hurt and disappointed relatives asking why you won’t be coming to Grandma’s house for Christmas eve.

Tips for Budding Entrepreneurs

Nobody can keep up a startup level of work forever, and our families are why we do this at the end of the day, but it’s important to prepare them for your absence during these special times when it is necessary to keep working to keep your business afloat.

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15. ‘Rest, Recharge, and Focus on Human Interactions’ – Paige Arnof-Fenn, CEO and Founder, Mavens & Moguls

Paige Arnof

The holidays are stressful/exhausting, a mentor once told me that to stay sane and be successful at year end “me time” is not a luxury or pampering, it is maintenance, respecting my time on the calendar and taking myself as seriously as I take my most important clients is the most important act I can do to care for myself because if I am not at my peak performance I am not going to be useful to anyone else either so I have learned the following.

Tips for Budding Entrepreneurs

Give yourself permission to say no. Whether it means sleeping in (no to an alarm clock), meditating, taking a walk, delegating more work, or just turning off your phone and computer (no I will respond later on my own schedule), simple acts of letting yourself relax and enjoy the moment are the very best gifts you can give yourself. It is about touching people in meaningful ways which may mean being less busy not more.

Disconnect from technology periodically and focus on cultivating human, face-to-face relationships (when not social distancing). Even meeting for virtual coffee or drinks can accomplish so much more than e-mail exchanges, social media posts, etc. I have found that building relationships is what drives my business and technology supports them once they are solidified. Technology helps advance the conversation but it will never replace the human interaction that builds trust over time.

16. ‘Prepare Supplies and Facilitate Payments’ – Marques Thomas, CEO and Founder, QuerySprout

Marques Thomas

Businesses are indeed preparing as the holiday season is finally approaching again. They have planned numerous strategies to make their products and services attractive to their target customers. Startup founders are somehow new in this phase. Hence, they need tips on how they can maximize their business in this season.

Tips for Budding Entrepreneurs

The first thing you should do is prepare your supplies. As much as possible, do not prepare a lot when there is no survey conducted among your potential clients. Doing so will help you to know what they are looking for in the upcoming season. You will not lose a lot once people do not want to buy your products or consider your services.

Next is, you have to prepare email templates to help you connect with your customers. Doing so can help you to build a relationship with the clients. You can do this with just a click, so it allows you to save time and budget as well.

Lastly, create many modes of payments as much as possible because it is one of the factors customers are looking for. Consider the people who will order inside and outside the country if you open the business internationally. Make sure that the packaging is safe so the products will not get broken once received.

17. ‘Unify Your Employees’ – Marilyn Gaskell, Founder, TruePeopleSearch

marilyn gaskell

Right before our employees leave for their Christmas break, we announce the goals we want to achieve the next year so that our employees know what to expect when they return from the holidays. The purpose of announcing our goals to our employees is not that we expect our employees to single-handedly achieve them — we simply do it so that all our employees can be on the same page and aware of what the business is working toward.

Tips for Budding Entrepreneurs

Having a unified workplace environment and a common goal always does wonders for our employees’ productivity and the best part of announcing it right before Christmas break is that it gives your employees time to digest the information, take a break, and return refreshed and ready to the workplace.

18. ‘Embrace the Change and Be Innovative’ – Jaya Aiyar, CEO and Founder, Créatif

Jaya Aiyar Creatif

The global pandemic makes it harder for business owners to thrive and catch up with holiday orders as we approach the most wonderful time of the year.

Tips for Budding Entrepreneurs

The number one piece of advice I can give to my fellow managers and start-up leaders is that you need to embrace the change and be innovative. Since customers cannot come to us, we must go to them. We cannot hold our physical stores, and some restrictions are still applied. We have turned to technology and social media like Facebook, Instagram, and the like. Of course, we needed to pay extra to endorse our brand, but I am telling you, it was all worth it.

19. “Consider Uncertainties” – Grant Aldrich, CEO and Founder, Online DegreeGrant Aldrich

You should start planning for the holiday early. And with a year like this? The earlier the better.

Tips for Budding Entrepreneurs

When you’re a retail startup, this is going to be especially important. You will want to make sure you start planning months ahead to make sure inventory is ready to go before it hits rush season. The reason why that is even more relevant this year (and possibly in the future) is that there are port delays and container shortages. Everyone is also trying to get ahead of the game as well.

With startups, it’s likely you have a small team. Vacation Time can be tricky.

This is more of an issue for startups that hit peaks during the holidays, such as a retail startup. You’ll want to keep the team working around the holiday and not taking a ton of time off. Then maybe a breather is needed right before Christmas.

For B2B startups, it’s usually the opposite. December is when business usually starts winding down. A good time for prospecting, but a lot of businesses are going to want to wait till January when they start a fresh budget to sign any dotted lines. That means it may be easier to be lenient during the end of December so that the team can be fresh the beginning of January.

20. “Maximize Sales Using the Bundle Strategy” – Michelle Devani, Founder, Love Devani

Devani Architecture

As a business person, this holiday season is an advantage for us. Businesses could formulate strategies to maximize the sales that they could gain this season. One piece of advice that I could suggest to everyone is to utilize the bundle strategy.

Tips for Budding Entrepreneurs

Since people are acquiring items as presents for their loved ones this season, entities should take advantage of it. They must package their items in a bundle to give customers an idea that their offered products can be used as gifts. The market prefers this type of item because it eliminates the need to think extensively about a gift.

21. “Invest Time in Networking” – Christian Velitchkov, Co-Founder, Twiz LLC

Christian Velitchkov

The holiday season is the ideal time for networking. Hence, as an entrepreneur, to make the most out of your holiday season, start leveraging your networks during this time.

Tips for Budding Entrepreneurs

Regularly connect with your prospects or regular clients and let them know about the ongoing offers in your business. It can also help in fostering better relationships and making them stronger over time. You can also start a conversation with a community of prospects and indulge in a conversation with them while subtly promoting your business regarding its advantages. These ways, you can reach a wider audience base and build a better brand authority as you connect with more people and share your valuable insights with them. Some of the best spaces to connect are Quora, LinkedIn, Reddit, etc. You can also leverage your email marketing campaigns to send out valuable resources of content during these times to your prospects and build a good connection with them.

Final Words

The festive season is almost here. Therefore, do your best and grab every opportunity you can. Take inspiration from and work on the tips and advice of these 20+ startup founders to grow your business, make larger sales, with minimum yet smart efforts this holiday season.

So, what are your activities during the holiday season? Share what you do for yourself and your startup this time of the year, and how you make the best of it, in the comment section below! 

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Sadia Zia

I work as a Senior Digital Content Producer at Cloudways. Creating content keeps me busy for the most part, but I relish discovery, adventure, and thrive in challenging situations and environments.


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