A Holiday Fundraising Pro Tip

Jason Yeh
December 17, 2021

With the end of the year approaching, a lot of founders are reaching out to me via email, blog comments, social media, etc. There's a lot of anxiety around ongoing raises that are not doing well. There's pressure to prepare and decide whether or not to launch a raise right now. And, there's pressure to prepare for raises in 2022. 

On top of all that, there's life. The end of the year is a holiday season and is for most people, a joyous time.  Unfortunately, the responsibilities of running a business don’t pause because Santa is coming to town. Between landing fundraises and closing out Q4 sales, the end of the year can be a pressure-packed time.

With all those professional responsibilities, the whole “life” thing can easily take a back seat. Around this time of year, I try to balance my fundraising advice with advice that applies to family life, overall health, and relationships. That's why I'm excited to share this holiday pro tip! It's fundraising-related but combined with guidance that is helpful in any situation, not just in a professional context.

When it comes to fundraising, the power of someone's network has such an outsized impact on the outcome. I often reference the fact that before I raised money for my last company, I had essentially spent 10 years slowly building a network and credibility. If I didn't have those 10 years, I probably wouldn't have done so well because I'm not naturally a great networker or the best at keeping in touch.

The founder and CEO of Journey Meditation Stephen Sokoler is a good friend of mine. Over the years, I would receive a text message from him around the new year saying “Happy New Year” and expressing how much he appreciated having me in his life.

A few years ago I was fortunate enough to spend New Year’s with Stephen and see firsthand how he did it. On New Year's Day he would spend three to six hours going through his phone book and sending personal text messages, expressing his gratitude and wishing people a Happy New Year. I loved seeing this. As a natural introvert with my own collection of peculiarities, I was uncomfortable with the idea of texting people that I may not have talked to over the last year or even for multiple years. But after seeing how much people appreciated Stephen’s outreach and how effective it was at nurturing important relationships, I started adopting a similar practice. At the end of every year, I spend time looking through my contacts and finding opportunities to send personal notes to people.

The motivation is purely personal, but many people I consider to be close friends also happen to be business people. They’re people I've worked alongside, helped in a professional context, or admired for their business accomplishments. More than once, my annual check-in to say hi and express gratitude has led to interesting catch-ups related to business. 

This is the context for my holiday pro tip for you. Whether or not you're a founder who's fundraising, but especially if so: take stock of your personal and professional network and set aside time to reach out as personally as you can. Awareness is crucial when it comes to fundraising. People can't invest in you or help you if they don't remember you. A short note saying hi, expressing gratitude, or wishing people the best can lead to great conversations and make it much easier to reach out again in the new year as you start a fundraise. The additional physiological and psychological benefits of gratitude don’t hurt either…

So how should you do it? 

Think about balancing a personal touch with scale. It would be best to talk to everyone live, but that’s likely impossible given your other commitments. Of the scalable tools, text messaging is the most personal but still a fairly manual process.  For the people closest to you, I think the juice is worth the squeeze because it feels that much better.  

For text messaging:

  1. Write out a generic message setting aside room to add personal touches and of course their first name
  2. Use your desktop texting tool like iMessage (apple) or Google Voice and copy that message
  3. Go one by one through your address book and send the message with personal touches to those you feel comfortable texting
  4. When you text someone track their name in a spreadsheet (to be used in the next step)

Text messaging is highly personal. There are some people who you could get in touch with, but you don’t have their phone number or feel uncomfortable texting them. For those, email works great.

Here’s my email process:

  1. First, create a list of people you would prefer to contact over email.  Email allows you to cast a much wider net and my favorite approach for this is to look at all the emails you sent over the last 1-2 years.  If you emailed someone or they emailed you, they are probably a candidate for a Happy New Year email. Go through all your emails quickly (honestly won’t take as long as it might sound) and jot them down in a spreadsheet. 

    Be sure to cross reference the list of people you texted so you don’t accidentally email them too!
  2. Next, write an email template. You can use similar language to your text message.
  3. Set up a mail merge program to help you send all the emails at once. My tool of choice is YAMM because of how easy it is to use with google sheets and gmail.
  4. Since you’re using mail merge, you can use variables to personalize your messages. The most obvious is including a variable for their first name. Besides that, I also like including a placeholder variable for an optional personal blurb for those you have something extra to say to. I usually include it at the end so the template makes sense whether or not you include the extra blurb.

There you have it- my favorite holiday fundraising pro tip. Dedicating just an hour away from your parents, aunts/uncles, and nieces/nephews to do this will activate your network, drive more awareness, and deliver some really positive personal benefits. Expressing your gratitude and keeping in better touch with friends and family are important things to aspire to, regardless of your fundraising status. The catch-ups and conversations that would have otherwise not materialized just might create momentum for your fundraise as well!

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