On Tuesday, I joined a fantastic webinar from Michigan’s Ross School of Business  about leading in uncertain environments, with economist Justin Wolfers and journalist Stacey Vanek-Smith. When asked what small businesses should do now, Wolfers said this:

“Your competition isn’t big businesses. It continues to be other small businesses. You don’t have to outrun the bear, you just need to not be the slowest human.” 

Unless you’re challenging a larger or more established company for business, most of you are trying not to be the slowest human. But you might spend a lot of time thinking about that bear.  

If you’re reading this newsletter, you’re probably further ahead of the bear than you think. For example, I tend to think I’m behind on AI adoption. But as one of my former b-school professors pointed out last week, in the business world, I’m an early adopter. My peer group happens to include a lot of cutting edge folks. So I feel urgency to act, even when I’m nowhere close to being eaten by the bear. 

In an uncertain economy, the idea of investing in anything might be No or Not Right Now. In your future planning, think about where not investing would cause you to fall permanently behind. That’s you, the bunny, getting batted around by the bear claws. If that’s real, you need to make the best choice you can right now. 

On the flip side, if you know that lots of people are sitting on their hands with their wallets closed, perhaps it’s a good time to make a bigger bet, to put even more ground between you and that grizzly. 

Some other webinar takeaways, with editorial notes from me:

• Keep a regular eye on regulatory and political changes, but don’t feel like you have to hit refresh every hour. That can lead to being overly reactive. And it will definitely disregulate you.

• Have a holistic view of your current market, including the economy and policy conditions, so you can take in new data and evaluate whether it changes your outlook.

• Stay on top of your cash flow. If you’ve been reviewing quarterly, start doing it monthly. 

• No amount of drop in interest rates can offset a desire for more certainty around tariffs, Fed independence, and political stability before investing. But, even in this economy, you can’t skip over investments if it means you’ll fall permanently behind. 

• You’re over-incentivized by tax changes and rebates. Focus on profitability first and you’ll be lucky enough to have tax issues (and the money to pay experts to help you). 

• Use a range of reliable news sources. Consider one paid business news subscription to reduce the impact of screaming headlines that entice you to click for social views and advertising dollars. (Addition from me: have one news source you trust from outside the US.)

But seriously…less reactivity to social media and every single policy change. The current administration’s policy of “flooding the zone” is a different kind of bear. Keep a healthy balance so you can stay well out in front.

As you read this, you may also be learning the US government has shut down. If that happened, that means the Democrats have so far been unsuccessful in reinstating the 2026 ACA subsidies cancelled by the OBBB. 

Whether you’re an open enrollment rodeo veteran or it’s your first year buying your own health insurance, your options and costs will be substantially different for 2026, especially by state. With that in mind, I am developing two resources for you:

• By October 24, my 2026 open enrollment guide for self-employed and small business owners will be available on my blog.

• On October 28 at 12 PM PT, I’ll host a free webinar with expert guests to talk about using the marketplace, accessing small group plans, and finding other options for coverage. 

Both resources should help you update your policies and determine what you want to offer by the time the marketplace opens on November 1. Look for the RSVP link in next week’s newsletter.

October 15

• 2024 personal tax filing deadline

• Expiration of LA fires FEMA tax amnesty

October 22 - My 10 Weeks to Close series returns, to guide you through end of year benefits, strategy, and tax decisions

November 1  - Health insurance open enrollment starts on healthcare.gov and state exchanges

“It’s the same shell but the vibe is totally different”: Last week, I watched the WNBA playoffs at a women’s sports bar, in a group that included a first-timer man. (That’s his quote about how it felt.) Women’s sports continue their massive growth in both fan engagement and franchise value. Globally, women control $31.8 trillion in assets and 75% of discretionary spending. And 66% of women sports fans say they don’t feel understood by their favorite franchises. Seems like a lucrative opportunity. Download theWasserman The Collective^Ⓡ Global Fan Report here, and the Global Women’s Buying Power report here.

The invisible women: One more tidbit from the buying power report: women over 45, 30% of the global population who control 45% of that spending, ask merely that you stand for something and see them. That is a cohort with almost US$11 trillion, just asking not to be invisible. Seems like a lucrative opportunity.

A country for old men: The US version of TikTok shall live on, with a whole pile of old white dudes getting access to a wildly underpriced US deal organized by another old white dude who is supposed to be good at this. The joint venture bid is led by Larry Ellison, owner of Oracle and Paramount, Rupert Murdoch of Fox, Silverlake Partners, and venture capitalist / victimized billionaire Marc Andreesen. As of the time of writing, the US government is not taking a financial stake. TikTok’s US operations have been independently valued at about US$40-$50B, but this deal is for US$14B. Unfortunately, seems like a lucrative opportunity.

Does Amazon owe you?: Amazon agreed to a $2.5 billion settlement over predatory Prime subscription practices. Of the settlement, the US government gets $1 billion as a civil penalty, and the rest goes to up to 35 million defrauded people for $51 each. Find out if you qualify. Seems like…well, it’s free money.