Entrepreneur Office Hours - Issue #73
How to run a startup during the holidays
Here in the US, we’re post-Thanksgiving, and everyone is (or should be) in a Turkey coma. If you’re not in the US, you have my permission to be in a Turkey coma, too. Why not join the fun?
With that in mind, I’m keeping this issue light. It’s focused on two aspects of running a startup during the holidays, which can always be a bit tricky.
The first issue I tackle (in the featured article) is how to fundraise during the holidays. The second issue I tackle (in the Q&A) is how to handle dwindling sales and distracted customers/employees.
By the way, if you feel like giving me a holiday present, you could press this big share button:
Is It Possible to Fundraise During the Holiday Season?
Every entrepreneur knows the holidays are a terrible time to fundraise. But that doesn't mean you can't be productive. Here's some advice in case you're preparing to face the holiday fundraising gauntlet.
Office Hours Q&A
I run a B2B company, and sales always slow down during the holidays. Any advice for keeping sales strong at the end of the 4th quarter, particularly when you’re running a company that doesn’t sell to consumers?
OK… I made up this question. But it introduces a topic I really wanted to cover in this issue to go along with the above article about fundraising during the holidays.
For lots of consumer-facing companies, the holidays are their busiest and most lucrative time of year. But, if you’re running a B2B company (particularly B2B SaaS, which was my specialty back in the day), the holidays are always a killer. Getting sales meetings is like pulling teeth, and nobody is buying. Everyone is “budgeting for next year.” Blech. Plus, your team is more distracted than normal, and the irregularities of everyone’s schedules can grind team progress to a halt.
For anyone in a similar position, I want to share some advice.
Don’t expect magic to happen specifically for you and your company. Instead, expect that your sales (and productivity) will drop in the 4th quarter, and make sure it’s in your revenue projections. It’s harder to be annoyed about something you’ve planned and accounted for.
Avoid gimmicky sales. Your B2B, SaaS company doesn’t need a Black Friday deal. It’s going to cheapen the perception of your product and, honestly, earn you the wrong types of customers.
Despite the general challenge of making sales during the holidays, it’s still possible. You just have to find the right types of customers. In my experience, a lot of the people still buying in December are the ones with “use it or lose it” budgets to spend by the end of the year. At my company, we had our SDRs include a question during our qualification calls to help figure out whether or not the prospect had budget deadlines.
The holidays are not a good time to experiment with new customer acquisition strategies. You’re not going to get good data.
Use the holidays as a time to accomplish major internal projects that might be disruptive to a company’s workflow. For example, if you’re thinking about implementing a new CRM, don’t do it in September when the sales team is firing on all cylinders. Instead, do it during the holidays when half the sales team is on vacation every week anyways.
Embrace the holidays. Seriously. Just do it. As an entrepreneur, you’re surely obsessed about your company and its success. Anything that hampers that success might be frustrating, but try to remember that other things matter in life, too. Things like family, friends, health, and happiness. When I look back on my startup career, those are all things I wish I’d appreciated more. Don’t be like me. And happy holidays!
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!