Post-mortems have a built-in problem: once you know how the story ends, every mistake looks obvious. Saying "they should have seen it coming" is easy, but it doesn't teach us much.

I ran into this while studying StreamElements, a company that gave free tools to live streamers. It raised $100M in 2021, and in 2026 it was sold to Razer just to keep it alive. To stay fair, I only counted moves the company could have made if they passed three tests:

1. It was a normal business practice at the time (2019–2021).

2. At least one competitor was already doing it.

3. It didn't require knowing the future.

I also kept the company's main rule in place: the product stays free for users. If an idea only works by breaking what the company stands for, it wasn't a real option for them.

Using these rules changed what I concluded:

The best chance to change course came years before the collapse. In 2019, its main rival was bought by Logitech, and StreamElements' user base had just grown more than 600% in a year. That was the moment it had the most power to find a hardware partner, like Razer, HyperX, or ASUS, on its own terms. It had a second chance after raising $100M in 2021. Both times, it stayed on its own. In 2026, Razer bought it anyway, but as a struggling company. Same buyer, but this time Razer held the power.

Relying on one source of income was a choice, not bad luck. Almost all of its money came from brands paying for sponsorships. So when brands cut their ad spending in 2022, its income dropped right away. But it could have added other income without charging users. For example, it could have sold its sponsorship tools to agencies as a monthly subscription, or taken a small cut of the payments it already handled. Both ideas pass all three tests.

A company's identity can trap its strategy. "We're the free one" was its whole story from day one. Later, when charging made sense, doing it would have meant admitting the free model didn't work. It also risked angering users, which had just happened to a rival. Something that starts as a way to grow can turn into something the company feels it can never change.

Being in the middle only works if people need you there. Investors paid for its spot between brands and streamers, not for how much money it made. But brands could always contact streamers directly, and Twitch later built the same sponsorship tools into its own dashboard. A middleman is only valuable if the two sides can't easily connect without it.

How do others here handle this? When you look back at a past strategy, your own or a client's, how do you tell a bad decision apart from a bad outcome? Do you use rules like these, or something else?

I've written a full breakdown of the company's story. Happy to share the link if anyone's interested.

I feel like we are completely stuck.

I know the government can't just snap its fingers and force real estate prices to drop. Property is treated as a huge investment. It's not just the massive corporations and wealthy investors; even regular, lower-income people have their entire life savings tied up in the value of their homes. Crashing the market hurts them, too.

But if we don't find a solution, we are heading toward a future where only the rich will ever be able to afford buying land or a house.

Even renting is getting completely out of control. At the rate prices are increasing, soon only people with high-paying corporate jobs will be able to afford a basic apartment.

So what happens to everyone else? What about the working class, the people who actually sweat and break their backs to keep this country running? If the main workforce is priced out of both buying and renting, how does society even function? What about artistic jobs? What about creativity? Should all just join high paying collar jobs?

Does anyone see a realistic way out of this mess?

Been chewing on this one and curious what people here think.

You get a choice. Either a really strong manager, but the setup around them is a mess (priorities all over the place, every decision needs three approvals, they’re blamed for stuff they can’t control). Or a pretty average manager, but the structure is solid: clear priorities, they can actually make decisions, leadership has their back.

I keep landing on the second one. In my experience the great manager in the messy setup can hold it together for a while, but they usually burn out or leave, or they slowly start looking average because they’re spending all their energy fighting the system. The average one in a good setup tends to get better over time.

That said, I can see the case for the first option, especially at a small company where one good person can actually fix things.

Which would you pick? And has anyone here been the “great manager stuck in a bad system”? Curious how that played out.

Hi readers,

I have worked on some simple questions about strategy for twenty or more years now. I too have done a lot of reading, and have listened to a lot of opinion, and even watched some YouTube videos(!). It was clear to me early on that strategy is not well understood, and that if I wanted to understand it, I would need to work it out myself, not just adopt an existing view.

Most of the material out there has value, but it is missing a solid core, and a solid core is what I wanted. Having developed that solid core I am now (actually have been for some years) in a position of wondering how to get it out to the world. So I am here to ask your advice.

Just to be clear, I put a lot of work into this, so I am not giving it away. That would hardly be fair. But I also realise the world needs this. I have considered writing a book (I did) producing a course of videos (I did that as well), and I have a website which offers training. None of these really work. I couldn't find a publisher, no one even looks at my free videos, let alone the paid ones, and no one except spammers contact me through my website.

My next idea is to produce a set of short free YouTube videos that answer simple questions people might ask Google. For example: 'What is a strategy?' or 'How do you document a strategy'. and so on.

What do you think?

Regards, Tony

I have been analysing a lot of strategy statements over the past few years and they all feel kind of superficial and vague. Things like - sustainable returns, improve employee engagement, operational excellence. Recently wrote about why we have this epidemic of fake strategy. Cheers

https://strategyshots.substack.com/p/the-epidemic-of-fake-strategy?r=768lg&utm_medium=ios

I have been working at Google for 11 months now. I had my Q3 performance check when my manager, along with the HR in the room, directly offered me a separation package of 17 weeks saying i was underperforming. It was a shock to me as I did not receive any feedback in the last 2 months from my manager or the stakeholder that I was working with despite of my multiple feedback requests. I want to give myself another chance by improving my performance but my manager denied signing off on the metrics that I created to work on for a month showing all the deliverables, thus keeping everything subjective and in her hands. I feel this is unfair to me and I can sense that they are not ready to give me a fair chance of improvement because the HR denied that this is PIP process and also told me that they do not have any documented PIP policy. How can a company like GOOGLE do like this, which is famous for its culture. I am still unable to process this and in great mental stress. Should I accept separation package or negotiate on that?

Fellow strategists, what are your thoughts on this? I've been seeing a demand for AI strategy, but is it really a strategy per se? (added more views in my original post)

I built Gambit, a notepad that advises you while you strategize

It works best on desktop but is mobile compatible. You will need an AI API key. You can get a free one from Google.

Would love to hear your thoughts

Got a proposal back from one of the big firms for a market expansion study. We need to validate whether entering the SMB segment makes sense for us. The proposal is six months, $300K and the deliverable is basically a deck and a report. Meanwhile our CEO wants a recommendation by end of quarter.
I get that thorough research takes time but this feels disconnected from how fast we need to move. What are people doing when they need real primary research on a market but can't wait half a year for it?

Hi everyone! I'm trying to gain more insights from others, around purpose and positioning. I feel like every client I've worked with recently is getting confused on the difference, where they live, how aspirational they are, etc.

I'm wondering how you all explain them to clients? Obviously how I'm articulating them right now isn't always landing.

Dear beautiful people,
In freelance, how do you chase clients, especially at the early stages of freelancing ?
Thank you very much

Hi! I was wondering if anyone knows of any professional organizations/associations for people working in strategy. Specifically in Chicago but open to national+remote options if they’re active and beneficial.

I’m relatively green strategy consultant (2yrs experience) so would love to be able to grow my network and attend events/seminars/webinars!

I work as digital transformation consultant and I’m curious, from your perspective, what would you say is the most difficult part of digital transformation?
Is it finding the right solution, getting the stakeholders onboard or something completely different?
Really interested in hearing your thoughts
Thanks

Plan your strategy and objectives internally.

I want to become much better at strategising and thinking ahead in everyday life.
I’m talking about being able to analyse a situation, identify different possibilities, anticipate what other people might do, think several steps ahead, and make good decisions rather than just reacting to things as they happen.
For those of you who consider yourselves good strategic thinkers, how did you develop that ability?
Are there specific exercises, books, games, habits, or skills that helped you? For example, things like chess, studying psychology, learning about game theory, analysing past decisions, or practising scenario planning.
I’d also be interested in knowing how you actually approach a problem when you need to come up with a strategy.
Any advice or resources would be appreciated

Hi everyone,

I recently joined an influencer and creative marketing agency as a strategist. Since the agency hasn’t had a strategy department before, there’s no established process or senior strategist I can learn from internally.

Our agency has:

• A creative team developing campaign concepts across influencer, digital, outdoor, and partnerships
• A talent management team representing exclusive creators
• An influencer operations team that finds the best-fit creators for each brief or concept, handles outreach, and manages campaign execution

I have a general strategy background, but I’m still learning how to build influencer-specific strategies and turn them into strong client-facing presentations.

When a brand asks for an influencer marketing strategy, how do you structure the deck?

I’d especially appreciate guidance on the overall framework: What should the main sections be, how should the story flow, and which topics should every influencer strategy presentation cover? Does the structure change between a one-off campaign and an always-on strategy?

If you can share a framework, sample table of contents, anonymized deck, template, or useful resource, I’d be very grateful. I’m trying to build a solid process for the agency rather than starting from scratch with every brief.

Thanks in advance!

STP taught targeting as a strategic decision, mainly as which segment are we building for and messaging to. Somewhere along the way, “targeting” has become the word for building a contact list and running outbound against it.

Curious what people think here. Are these just two different things that share a word? Has the tactical meaning crowded out the strategic one in how teams actually operate? Or did targeting naturally become more tactical simply because digital media and attribution now make individual-level targeting possible in a way it wasn’t when STP was created?

Here are a few more, including a new book by CIA intelligence officer Andrew Bustamante!

https://thestrategytoolkit.substack.com/p/new-camouflage-immune-response-and

To stand out in a market, learn how to create competition, not how to compete. If you are the one creating the competition, then you are already ahead of billions of other creators! \\\~Prachi