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

Updated on October 9, 2023

14 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 advice 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. ‘You Should Market to Clients Who Are Loyal’ – Andrew Johnson, Owner and CEO, Prime Seamless

Andrew Jhonson

As a startup owner, it is my everyday job to bring value to my employees and customers alike.

Tips for Budding Entrepreneurs

The Christmas season is one of the busiest times of the year for businesses, and as a result, acquiring new consumers typically takes more effort and costs more money than retaining existing customers. 

Existing customers might be enticed to make Holiday purchases; by providing them with targeted discounts and promotions, in-store events, and unique online offerings, you can boost sales.

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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. ‘Show Your Personality’ – Alex Constantinou, Managing Director, the Fitness Circle

Alex Constantinou

Enjoying your work is important if you want to succeed. I’m all for being professional but being serious all the time isn’t a wise strategy.

Tips for Budding Entrepreneurs

Keep in mind that the holidays are a wonderful time. Have fun, and don’t be scared to let your hair down. Even though you can’t party with your clients, you can have fun with them, be yourself, and develop a genuine connection that will last well into the current Christmas season.

Whatever holidays you celebrate, the season is open to everyone. During these months, adding a little holiday cheer to your marketing efforts will help you stand out from the competition and become more relatable to your target market. Make sure you and your team won’t miss the best chance to engage customers more authentically by taking the time and doing the additional work.

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. ‘Enhance Your Website to Attract More Visitors’ – Adam Crossling, Head of Marketing, Zenzero

Jon Bennion

If your website isn’t prepared for a surge of traffic, it may slow down or even crash during peak times. For this reason, it is recommended that you reduce your site’s loading time so that it can accommodate a rise in traffic during the peak season. If a website takes too long to load,
visitors will likely leave without purchasing anything.

Tips for Budding Entrepreneurs

Customers are more likely to leave your site for a rival if it takes more than a few seconds to load. That’s why it’s crucial that you make your site mobile-friendly, bug-free, and user-friendly so that people can purchase from their phones. These modifications to the mobile purchasing experience can boost conversions and revenue.

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. ‘Incorporate Both Online and Offline Channels Into One Streamlined Shopping Experience’ – Robin Antill, Director, Leisure Buildings


Robin Antill

Traditional organizations often fail to see the importance of establishing a robust online identity.

Tips for Budding Entrepreneurs

If you don’t already have a web store, you should at least have your company listed in Google’s business directory. Doing so will lend credibility to your company in the eyes of such an online shopper, who may then decide to visit your physical location. To do so requires simply a short amount of time.

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 Upgrade Technology’ – Steve Pogson, Founder and E-commerce Strategy Lead, Firstpier

Steve Pogson

Make sure your website can handle heavy traffic, especially if it is not used to receiving a lot of visitors at once. Before major shopping days, conduct tests, and prepare a response strategy in case of downtime or crashes.

Tips for Budding Entrepreneurs

Particularly this year, ensure that technology is prepared and capable of handling the influx of online holiday customers. If your website is down or you are having trouble processing credit card orders, you’ll lose potential clients. This calls for investing time in security software upgrades earlier in the year, testing checkout and payment procedures, evaluating the usability of search features, and ensuring that your website is user-friendly and ready to handle an increase in traffic.
this might also be a good time to hire a CTO for your organization if you don’t have one yet.

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.

Here Are Some Tips for Black Friday Email Campaigns to Skyrocket Your Holiday Sales

15.‘Stock up on Holiday Inventory’ – Dan Close Here, Founder & CEO, We Buy Houses in Kentucky

Dan Close

Nothing is worse than having to turn away a new client because you are out of the in-demand present. Make sure your online business is adequately supplied and that you have lots of your bestsellers on hand to prevent this situation.

Tips for Budding Entrepreneurs

Stock up on your best-selling products, the newest trends in your sector, and uniquely branded or handcrafted presents that stand out from the competition. Ask for discounts from suppliers or longer payment terms if you can buy in greater volumes.

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. ‘Visualizing’ – Bram Jansen, Chief Editor & Co-Founder, VPNAlert

Bram Jansen

Building a story for your clients and potential customers will be really helpful for your startup.

Tips for Budding Entrepreneurs

Consider your channels before creating Christmas pictures and holiday season campaigns. Be creative with your images. Keep your visuals contemporary and festive by including snowflakes, bows, gifts, and pine trees. Increase the font size of any text in the visual to make it simple to read.


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

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 Degree

Grant 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. ‘Ask People to Share Your Content’ – Zephyr Chan, Founder, Living the Good Life


Providing a great product and creating a nice experience for customers is the ideal way to encourage them to share your content and spread the word about your brand.

Tips for Budding Entrepreneurs

Urge your consumers to share your content and product information with other interested prospects. Numerous new organizations have adopted this marketing technique, which aims to acquire a higher number of customers in a shorter amount of time. 

Giving away free items to clients as a way of saying thank you is also one of the most effective ways to market a product online.


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 and 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! 

Share your opinion in the comment section. COMMENT NOW

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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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