A business strategy session is a short, focused conversation — typically 15–30 minutes — where a founder brings an unresolved decision or problem to an advisor. Unlike a sales call, the goal isn’t to pitch a program; it’s to identify what’s actually going on and what the next useful step is.
I’m back from vacation
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.
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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:
- What have we accomplished?
- What’s still off track?
- What needs to change in order to make the rest of this year as successful and productive as possible?
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.
So, what happens in a 20-minute strategy session?
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.
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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.
Good news: that’s not what happens in a strategy session with me
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.
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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:
- Sometimes I can answer the question.
- Sometimes I can tell you what kind of person you need to ask.
- Sometimes the answer depends on information you don’t have yet, and I can give you an “if this, then that” frame so you’re not stuck waiting until the data is perfect. (PS, it will never be perfect.)
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:
And one more thing: you are not wasting my time
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.
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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.
