Hi, it’s me again. Actually me, back from vacation. 

In July 2006, I moved from Chicago to San Francisco. Soon after, I bought my first car, a zippy Volkswagen GTI, and promptly embarked on a road trip down the coast to Los Angeles over a delightful week. 

Earlier in the year, my kiddo pointed out that amidst all the stamps in his passport, he had never been to Northern California. Oops! 

So we slapped together a 6-hour shared playlist and re-created my roadtrip in reverse. We visited seven California missions (his pick), drove the Big Sur section of PCH (my pick, not his favorite), played a round of golf at The Hay Pebble Beach (his choice, not my favorite), and resurrected the North Face fleece jacket that’s lived in my trunk for 19 years, way too warm for LA but ideal for battling Karl the Fog.

🔎 Read more: When AI makes sense for your business (and when it doesn’t)

My wandering spirit is sated, for now. I’ve also operated an EV over distance, which deserves its own summary of lessons learned. And don’t fear for woke: thanks to the National Parks Service’s Alcatraz tour, I got to explain syphilis and its long-term effects to a ten-year-old. These are the memories you just can’t replace.

Thanks to Liz and John for their guest writing stints on brand messaging and business valuation, and to my team for holding down the fort. There’s not a finer test of how your team and systems are doing than taking a vacation at the end of a quarter, leaving a list of multistate compliance and payroll tasks. 

Like you, I’m now back at work and staring down the second half of the year:

You may be asking yourself some version of the same questions. If so, a free 20-minute strategy session with me might come in handy. 

But I get asked often what actually happens during one of these sessions, which is fair. “Strategy session” can cover a lot of ground, from genuinely useful conversation to a thinly veiled Trojan Horse-sales pitch. So let’s talk about what mine is, what it isn’t, and what you can expect when we sit down together.

Before I fully shut off my work brain, one of the things I was thinking about from our 2Q review was, why aren’t more of you calling me? 

You’ve likely noticed that, in each issue, there’s a link for you to book a free 20-minute strategy session with me. 

Which, of course, begs the question:

“Since nothing in this world is actually free, what’s the catch?”

Fair. 

You’re grown people. It’s not your first rodeo. You have your own marketing programs and you know what “free” means. Yet, you show up hopeful that, maybe, finally, you’ve found a human who will help you with a frustrating problem. 

🔎 Read more: How to run a quarterly business review that works

But within 10 minutes, some “expert” (or worse, their bait-and-switch account rep) is trying to stuff you into a program, a package, or a “limited time opportunity” that somehow expires at midnight. 

I, too, have repeatedly reached out hopefully for promised help. And it sucks when that promise is gated by a payment and a wait. If you had money and time, you would have solved this already.

But I do want to be transparent about what a strategy session with me entails, and how to prepare for it.

Think of a strategy session with me like business urgent care. You don’t need to arrive with a polished agenda or a perfectly organized business problem. 

You can bring the two or three questions that have been sitting in your brain for months, the one decision you keep circling, or the thing you’ve already asked your accountant, your entrepreneur friend, Google, and Claude, and still don’t know what to do. We’ll look at what’s actually going on, sort out what matters, and figure out the next right step.

🔎 Read more: What I do as a business strategist for my clients

In 20 minutes, we’ll focus on what brought you there, what you’re trying to resolve, and what the next useful step looks like: 

If you want more information on what you can expect, and how to prepare for it to get the most value, I’ve got you covered with this new comprehensive resource on strategy sessions with me:

You are not blowing your one shot to ask me something. I appreciate that you and my other readers are respectful of my time. Sometimes, you’re being too respectful, to your own detriment. I offer strategy sessions because often, you just need a thought partner to help you get unstuck. 

If you’re interested in working with me, and you say that, of course, I will absolutely talk to you about that. 

But, if you’ve been here for a bit, you may have noticed that there isn’t a CTA or activation in this newsletter to buy stuff. In my consulting business, we have the capacity to work with about ten clients annually, and some founders work with us for multiple years. That’s all I do. I’ve offered communities, programs, and courses, and I did not like it. I do not want to puke a personal brand all over social media. I am 100% in on Old Money Face.

🔎 Read more: Yes, you can afford to pay yourself (here’s how)

I do three things: growth consulting, fractional management, and this free weekly newsletter. I know that most of you are never going to pay me $5-$10k a month for the first two. I do not care. I am happy that you’re here and that you are trying to build a healthy, sustainable, cash-flowing business of any size that works for you. 

I write this newsletter because I want to help as many people as I can to find their version of entrepreneurial success. If you are stuck, and you don’t know who to call, just book the 20-minute call. I’m not going to be mad if you do it again in a few months.

You may not see a spot open today. Because this is not a sales call, I am not trying to feast on your urgency. We have many options over the next two weeks. Please put some info into the intake form so I know what you want to talk about. And if you don’t see a time that works for you, reply to this email and we’ll work with you to schedule.

Thank you for subscribing and continuing to read this newsletter most weeks, even in the summer. Even when I write about boring but necessary stuff. As this list grows, 55-60% of you read this email every week. Many of you share it with your network. 

That means a lot to me, and I appreciate you.

Uptick in small business activity. While all eyes are on trillion dollar AI IPOs, small businesses are actually doing pretty well in the last 12 months. Small cap stocks are outperforming the S&P this year and had the best first half since 1991. If you’ve been of the mind that the US has been in a quiet recession since 2023, small cap performance is a sign that overall economic recovery has begun, albeit with loads of day-to-day volatility.

Interest rates. So…the US’s not-war with Iran is back on. The Fed has swung from a possible 3 interest rate cuts this year to a bias toward raising rates at least once to control inflation. Plan accordingly.

Fancy names for doing nothing. Old Money Face. Quiet luxury nude nails. Quiet Silver hair color. Capsule wardrobes. You can trend it up all you want -- basic and doing less is in. Welcome to my level of participating in trends, i.e., not.

ICYMI, here are resources you should know about:

If you’re relying on AI for any type of candidate screening, keep an eye on the ongoing Workday lawsuit. We’ve talked before about how AI can be a benefit to your business -- under the right conditions and with a clear strategy. But Mobley v. Workday Inc., a class action lawsuit that alleges Workday’s AI hiring tools discriminated against applicants, is a cautionary tale of how more tech can equal more problems. Yes, so many AI platforms promise you can outsource your messiest business problems to them. But when the problem involves judgment, bias, and real consequences for real people, you’re also importing the vendor’s assumptions, blind spots, and failures into your business.