26 Comments
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Dennis Berry's avatar

If you're not built to last... you won't last.

Those hockey stick growth curves are sweet! Substack did that too :-)

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Chris Tottman's avatar

Totally - Substack has to convert the $100m Round into compounding cashflows 📈

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ToxSec's avatar

“Governance has a reputation problem.

It conjures images of binders, committees, and consensus-driven paralysis”

so true Chris!

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Chris Tottman's avatar

“the world we live in with all the rules, forms, clicks to confirm, lines, signs, queues, kyc, notary, lights, guardrail, soft floors in playgrounds, reports, checks, sign-offs, etc” are the long term affect of flowing from the “1000s of risk and compliance committees” around the world 🤮 I love the thought process of considering in the UK “all the rules, regulations and procedures to wade thru in protecting the heritage of a old property that is falling into decay that was built when there were no rules, regulations and procedures” 😂 clip board land 2025 ✅✅✅✅✅✅❌❌❌❌🥵

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Karen Spinner's avatar

Chaotic structures are the bane of service companies, too!

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Chris Tottman's avatar

Which are about to go through the Software AI wave 🌊huge disruption coming. Services is 100x bigger than software 🤯 massive opportunity

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Cris Cafiero's avatar

Talent notices if you’re cutting corners… built to sell companies are typically looking for a fast exit, not longevity. A person’s career won’t typically align with that (unless they have meaningful equity at play)

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Chris Tottman's avatar

Quite possibly true and particularly true in the US where the examples of peers winning via epos sales/exits are abundant (less so in Europe). I think as you enter the exiting window (say 18mths out) there are some shifts in strategy ie leaner decisions & ROI becoming more focused but your comments holds very true I would say. Thanks for sharing your experience Cris ✨✅

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Nazanin Bigdeli's avatar

The best companies don’t choose between scaling and selling. They’re engineered to do both without flinching.

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Chris Tottman's avatar

Love that framing Nazanin 🌟

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Dennis Hedenskog's avatar

As a founder of several companies, focusing on building a solid foundation is always a good idea. The world changes fast and what looked like a sure thing yesterday, might not happen today. Setting yourself up for choices, instead of being forced into making decisions, is the way to go in my opinion

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Chris Tottman's avatar

Wise words 👏 congratulations on your success. I'm also a fan of being super plural with many many companies. I love the collaboration with others and the variety - particularly when the companies are synergistic 🤝

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Dennis Hedenskog's avatar

Thanks. I'm too curious to stay in just the one lane. I might not master anything, but I love to many topics 😆

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Chris Tottman's avatar

Me too. I'm known for saying that "I build companies that I don't want to work in" - because they're too scalable, repeatable and programmaticable ie boring to me. I like the chaotic wikdow at the beginning. So I hand them off to my collaborators or management because I'm creating others simultaneously 😬

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Dennis Hedenskog's avatar

You nailed me to. I love the early “anything is possible"-phase

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Chris Tottman's avatar

Brilliant

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James's avatar

This read like the moment you realise the ground has been slowly shifting under your feet, not because of one big shock, but because of many small, ignored signals.

By the time it’s obvious, it’s already been happening for a while.

Through the 5 Voices lens, this blind spot shows up differently:

Nurturers feel the emotional weight building first.

Guardians notice cracks in process and consistency.

Creatives sense misalignment but struggle to name it.

Connectors feel conversations thinning out.

Pioneers keep pushing forward, assuming momentum will carry things through.

When these signals aren’t shared early, the cost compounds quietly.

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Chris Tottman's avatar

Thanks James. As a creative I hear you !

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Bob DePasquale's avatar

I remember the first time I felt that smoothness of the business. It was still chaotic but certain things were clicking.

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Chris Tottman's avatar

I love it when the "flow state" kicks in for the company. 💙 Congratulations on your success 👏

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Trisha DePasquale's avatar

best to have a clearly articulated story and idea from the beginning

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Chris Tottman's avatar

Working on the "why", the "who cares", the "what we optimising for" ie whats in (very little )and what's out (almost everything) and then crafting that into a clearly articulated story over a few horizons 🎆 Magic !

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Passport Inspiration's avatar

you have to start this early and often, easy to get off track when you're building

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Chris Tottman's avatar

"off track" "back on track" "off track" "back on track" - repeat, repeat, repeat...like watching a todler going from crawling to walking to hopefully running wildly 📈

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John Brewton's avatar

Companies that can explain themselves cleanly tend to have more choices later.

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Chris Tottman's avatar

They have more gravity as " those who they're for find them more easily " - thanks for the wisdom John ! ✨

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