Entrepreneurs—Winter is Coming: Here’s How to Prepare

While almost no one is admitting it publicly, behind closed doors, most entrepreneurs tell me they’re struggling lately. And I’m not just talking about tiny businesses—I’m hearing this from entrepreneurs running businesses of all sizes, from the one man show all the way up to large companies with hundreds of employees. 

It’s not a matter of competence. It’s not even a matter of having a product or service that’s in high demand. 

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It’s a matter of today’s economy. 

Everyone is stretched to their financial limit. Inflation has driven costs for everything to near record highs, which means fewer customers are buying, and most aren’t willing to spend as much as in previous years, and tariffs have driven costs further.  This is creating a ripple effect throughout the economy, impacting all sectors. 

Add the recent layoffs driven by cost cutting efforts and implementation of AI and the coming storm becomes obvious. 

For the business community, winter is coming. 

As an entrepreneur with over two decades of experience, I’ve seen my share of good and bad economies. The dot com boom in the late 1990s followed by its crash just a few years later. The real estate boom in the early 2000s followed by the 2008 collapse. And the 2020 pandemic lockdowns that destroyed some industries while driving massive growth in others, to highlight just a few examples. 

Having lived through these, I’ve learned what it takes to survive, or better yet, thrive through economic uncertainty. 

Treat business finances like triage

Most entrepreneurs wait until it’s too late to adjust their budgets to changing economic conditions. They often keep spending as if this is just a blip that will rerun to normal any day. That’s a recipe for disaster. 

When revenue slows down, it’s critical to start cutting expenses for non-revenue generating activities. Travel, entertainment, and company retreats are good examples of this. While these can be useful for morale and team building, they’re not essential. Marketing, on the other hand, is essential and is one of the last things you should consider cutting. More on that shortly. 

Software is another area you should review closely. We’ve all subscribed to various software platforms to improve efficiency and productivity only to later find out they aren’t really a fit for our workflow or even forget we subscribed in the first place. I can’t tell you how many times I’ve paid for years for software I never used. The same applies for subscriptions for audiobooks, media outlets, data, and professional associations. Keep what you absolutely need, and cut the rest.

It’s also important to make sure you have access to business credit before you need it. As someone who has been in the position of not having enough money in the bank to make payroll or pay vendors on more than one occasion, I can assure you that credit can be a critical lifeline that keeps you afloat during a cash crunch. But it’s also just as critical to use this responsibly. 

You should never use it speculatively, especially in a slow economy. I generally treat it as a bridge over tough times for things that are absolutely essential to generating revenue. Payroll is just one example. You need to be able to pay your employees so you can complete the work your clients are paying you for. Materials and infrastructure needed for work you’ve already secured is another expense credit can be useful for. And scaling a proven marketing channel, if approached incrementally, may be another. The key is to use it conservatively and follow a plan to pay it off quickly. I suggest following the writing of Ari Page, one of the top business credit experts in America, for deeper insight on leveraging business credit effectively.

Double down on marketing

One of the biggest mistakes I see business owners make is cutting marketing when times get tough. I understand the thought process, but it’s a kneejerk reaction driven by shortsighted fear.

The unfortunate reality is that you keep your business afloat by simply cutting costs. Marketing drives revenue, and that revenue is essential to your business. Cut marketing and your revenue will decline.

In fact, I propose the opposite. During a down economy, most of your competitors will cut their marketing, so when you increase yours, you’ll gobble up the market share they foolishly gave up. We see this during every crash. Companies that previously led their industry cut their marketing, expecting their dominant position to keep new clients flocking to them. Meanwhile, other companies, seeing the opportunity amidst the chaos, doubled down more aggressively in their marketing. The end result is often a significant paradigm shift where industry titans fall while smaller companies grow to take their place.

The secret here is to approach marketing with the goal of building authority status and positioning your company as the only logical choice for your target market. Don’t try to compete by being the cheapest option though. That’s a race to the bottom and incredibly dangerous in a soft economy. Don’t get me wrong—you may need to lower your prices to meet market demands, but that should never be your primary focus.

During periods of economic uncertainty, trust wins. Consumers obviously want to spend less, but not at the expense of getting an inferior product or service. What’s most important during times like these is certainty. Consumers are looking for what will best solve their problem at a cost they can afford. They’re worried about costly delays, mistakes, and products and services that simply don’t meet their needs because that’s what puts their own businesses or households at risk.

So lean in on marketing instead of cutting it. Highlight what makes you best in class and then overdeliver. Align with trusted partners. Leverage public relations, SEO, and social media to show up everywhere your prospects are, demonstrate authority status, and nurture relationships through all channels.

If you do this aggressively and consistently, you’ll start to gain the market share your competitors give up, and end up in an even stronger position when the economy starts roaring again.

Lean heavily into self improvement 

I’ve always been a huge advocate of self improvement because I grew up poor and people didn’t expect me to succeed. 

When I was younger, I knew I didn’t have what it took to build the life I wanted, so I went on a lifelong mission to fill in the gaps. I analyzed the lives of successful people—both the celebrity entrepreneurs we all look up to and the smaller ones in my own circle. I asked about their lives, their journeys, and what made them tick. I wanted to understand what made two seemingly intelligent and driven people end up with dramatically different outcomes.

Then I started attending workshops to uncover what I was missing and learn what I needed to know to become better. Not just in business, but also in my personal life. One in particular was the Landmark Forum, where I was first an attendee, and then after significant growth, a leader guiding and supporting other attendees.

As terrible as it sounds, I’ve never been a fan of reading, so instead I started consuming audio books and podcasts at every opportunity. This expanded my mind even further, giving me a broader and deeper base of knowledge to make better decisions.

I even worked with several psychologists and coaches for more intense and personalized improvement.

As an entrepreneur, this is absolutely nonnegotiable. You must expand your thinking, identify your weaknesses, and consistently work to improve yourself.

And as a leader, which is a key part of being an entrepreneur, you also need to nurture this mindset in your employees, and give them an environment that fosters their own self improvement.

But there is a potential drawback to this. Well, a couple, actually. One is that it’s easy to take it too far by focusing more on self improvement than on running your business. That’s pretty easy to identify by paying attention to your KPIs. The other one is a bit tougher. 

When you help your employees become a better version of themselves, some will outgrow their role with you and move on to other opportunities. It can be frustrating to invest so much into people you genuinely care about only to have them leave you, but think about your own journey. It’s probably pretty similar, right? Remember, people have to do what’s best for them. But also remember that moving on doesn’t necessarily mean the end of the relationship. 

You may never cross paths with them again, but it’s also just as likely that they end up in a role that benefits you in some way. So don’t burn a bridge if some decide to move on.

In my experience, the entrepreneurs who not only become successful, but continue building on that success, evolving over the years, are the ones who consistently invest in self improvement.