Over the past decade, I've built three multimillion-dollar businesses while growing a family and raising four children.

I started with no resources, no connections, and didn’t have access to the playbooks that would have made the journey 10X easier. 

As a kid, I made money garden landscaping for families at church, manufacturing merchandise for private clubs, and then developing websites and running ad campaigns for local companies.

By 21, I was founding companies. In the decade since, I've:

➤ Generated $300M+ in revenue
➤ Built operations in 1,000+ U.S. cities
➤ Served over 3 million customers globally
➤ Helped grow hundreds of small businesses
➤ Raised $30M+ in capital from Angels, VCs, Private Equity, and Family Offices
➤ Successfully navigated both successful and failed multimillion-dollar acquisitions
➤ Been featured in leading publications like Forbes, Bloomberg, Entrepreneur, USA Today and more
➤ Worked with and advised the world's most iconic brands, including Diageo, Mars, Tesco, 7-Eleven, AB-InBev, Molson Coors, and Constellation

BUT, the journey was hard (harder than it needed to be).

I’ve faced many of the things you don't think about when starting a company:

→ Fought off (and won) predatory lawsuits
→ Closed a Seed round days after my wedding
→ Negotiated with demanding government agencies
→ Worked with lobbyists to introduce or change legislation
→ Raised a Series A while in the hospital for my first son's birth
→ Navigated a failed multi-million dollar merger while my daughter was born
→ Survived near-extinction events where we had single-digit weeks or days to save the company

Personal interests: Boxing, strength training, being in the ocean, spending quality time with my wife Danielle and our four little ones.

———

👋 Follow me for daily tips on mindset, systems, lifestyle design, and high-growth habits.

🔥Get my newsletter – Playbook Academy (www.playbook.academy). See why thousands of founders and executives read Playbook Academy every Saturday morning.

Chris Vaughn

Founder of StrategyBreakdowns.com

TLDR: Worked in strategy consulting → Joined strategy team at Atlassian → Started writing strategy case studies → People liked them, so I left my job and went full-timeCheck it out → StrategyBreakdowns.comWe partner with companies like Atlassian, Notion, Intercom, Hubspot, Miro, Vanta, Clay, Mixpanel, and Ahrefs to reach 110k+ tech decision-makers. Click here to explore sponsorships → passionfroot.me/strategybreakdowns

Tom Alder

Apple makes $1 billion+ per year selling adaptors:

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👉 P.S. If you enjoyed this post, you'll love my newsletter - a 3-minute breakdown of the strategy playbooks and growth hacks behind the world’s greatest companies.

Join 110,000+ strategy nerds from companies like Google, Meta, Atlassian, and Netflix: https://lnkd.in/g2FWfXGR

The average enterprise employee spends 31 hours per month in unproductive meetings.

That's almost a full work week. 
Every single month. 
Gone.

And yet - meetings aren't the problem. BAD meetings are the problem.

The best hybrid teams i've seen don't have fewer meetings. 
→ They have better workflows that make every interaction count.

I genuinely think something's shifted in how teams think about productivity.

It used to be about individual output - more hours, more tasks, more hustle.

Now it's about connection quality and output. How seamlessly can 50 people across 12 timezones actually collaborate without losing their minds?

The companies figuring this out are pulling ahead. The ones still optimising for "busy" are falling behind.

--

Zoom is running a free summit on exactly this: how to make collaboration seamless across teams, locations, and timezones.

Feb 24 (EMEA) / Feb 25 (APAC)

If you're leading digital transformation, IT, or workplace strategy at a large org - worth grabbing a spot.

Register here: → https://zm.me/49SCY8r

#ad in partnership with the legends Zoom

Jamming with Rob Hoffman, Lara Acosta, and Tyler Denk 🐝 about our plans for 2026:

A few topics we discussed -

1. The reality of building while traveling the world.
2. Why vlogging is coming back for founders.
3. The timeless psychology of waitlists.
4. The bootstrapped AI SaaS paradigm.
5. Solopreneurship vs small vs big teams.

Honestly so refreshing to get new perspectives on things I’m actively wrestling with.
Also funny to see how the same decisions / problems / strategies resurface in peculiar ways, in such different contexts.

Would highly recommend following what these folks are up to if you haven’t already!

Rob and Lara are building Kleo.
Tyler is building beehiiv.

Incredible businesses powering many of the world's top creators and founders.

Feeling inspired. Let's build.

Every company spent the last 20 years building customer support processes that make people want to hang up.

Press 1 for billing. 
Press 2 for support. 
Press 3 to scream into the void.

Then came the "AI upgrade" - which mostly just replaced the robotic menu with a robotic voice.

Same frustration, different wrapper.

Here's what's actually changing now:
ElevenLabs just shipped Expressive Mode in their Agents platform.

The demo is WILD (video below). 

The agents don't just listen to what you say. 
They detect HOW you say it.

Tone.
Pitch. 
Pacing. 
Humour.
Feelings.

And they respond with the right delivery - using cue cards like [reassuring], [apologetic], and [enthusiastic] to match the moment.

Frustrated caller? The agent shifts to calm de-escalation.
Excited prospect? It matches the energy.
Confused customer? It slows down.

Previously, agent emotion was shaped entirely through voice selection and system prompts. Static. One-size-fits-all.
Now it's dynamic and contextual. Across 70+ languages (up from 32).
The turn-taking is different too. Their new transcription model captures intent and emotional cues so the agent times responses more like a human would.
The result: customers feel helped, not processed.
That's the gap most people miss about voice AI. The technology was never the bottleneck.

The emotional intelligence was.

Link to try below 👇

#ad #ElevenAgentsPartner

Every AI tool you've used in the last 2 years has the same interface:

A text box with a blinking cursor.

Quarterzip threw it away entirely.

Instead of building another chat wrapper, they built an AI that watches your screen share and guides you visually - like having a colleague sit next to you and point at things.

No SDK installation. 
No browser extension. 
No IT approval ticket.

Just a picture-in-picture window that sees everything you see. Any tool, any tab, any workflow.

Picture this:
- You’re onboarding to a new tool
- You brace yourself for a barrage of forgettable tooltips and painful ‘educational’ flows
- Instead, you click ‘Start Onboarding’ and you’re prompted to share your screen
- You share, and you’re placed directly in the app, with a helpful AI assistant in the corner that sees everything you see
- It’s trained on the help docs, all past onboarding calls, and can guide you through the journey whilst answering any question you might have along the way

They launched a week ago. Already running hundreds of AI-powered onboarding sessions a day with Apollo and Grab.

And the growth loop is elegant - every person who gets onboarded through Quarterzip sees the brand sitting inside the PIP window.

Product usage drives distribution.

I broke down the full strategy in this week's newsletter (link in the comments)

On July 7th, 2025, I added another SaaS idea to the pile:
A Chrome extension. SimilarWeb for builders. Traffic, revenue signals, founder socials, ads - all in a sidebar you can trigger when you visit any company's website.

A 9-bullet sketch of something I'd personally use a dozen times a day, if it existed.

Nothing came of it. Got buried under many more (half-baked) ideas.

Fast-forward 6 months.
The Figma team reached out about a partnership.
They wanted me to try their new prompt-to-app AI tool, Figma Make.

I mulled over the angle for a while, then realised I had the perfect test case.
Could I take a 6-month-old idea that had never left the notes app and turn it into a fully interactive, clickable product prototype? Without writing a single line of code? Without opening a design tool?

The pipeline I came up with:
→ 𝗡𝗼𝘁𝗶𝗼𝗻 (raw idea, 9 bullet points) 
→ 𝗖𝗹𝗮𝘂𝗱𝗲 𝗖𝗼𝗱𝗲 + 𝗪𝗶𝘀𝗽𝗿 𝗙𝗹𝗼𝘄 (interview to flesh it into a full PRD) 
→ 𝗙𝗶𝗴𝗺𝗮 𝗠𝗮𝗸𝗲 (PRD in, interactive prototype out)

One sitting later, I had my answer.
Here’s how it went down (link in the comments 👇)

Most newsletter sponsors get a terrible ROI.

All because they're advertising to the wrong readers.

Here's the thing about audience quality that most marketers miss:

1/ You need readers who make decisions.

This is the #1 mistake I see. Advertising to e.g. 1 million people containing 1k decision-makers, rather than 100k people containing 50k decision-makers.

71% of Strategy Breakdowns readers have meaningful influence over budget and procurement decisions at their company.

You need to get in front of the actual people who sign off on the tools, platforms, and services their teams use.

2/ Open rate is a proxy for trust.

Industry average open-rate is under 40%. Strategy Breakdowns sits at 55%, while earning the trust of 110,000 readers every week. Our sponsors inherit that trust.

3/ Niche is more efficient than broad.

A 110,000-person list of senior strategy and tech leaders doesn’t just contain *more* decision-makers than 500,000-person general business list - it is also costs less to advertise in. The signal-to-noise ratio is what makes our campaigns so efficient for sponsors looking to allocate their marketing budgets strategically.

4/ The seniority and industry breakdown matters.

- 30% Founder / C-level
- 20% VP / Director
- 40% Senior / Manager

Tech, consulting, and finance make up ~80% of our audience. I mean, these are literally the buyers.

5/ One ad isn't a campaign.

The sponsors who see the best results run 4 touchpoints minimum. Decision-makers don't act on first exposure, especially at this seniority level. (Honestly, when was the last time you saw a $100/mo tool for the first time and immediately pulled out a corporate card?) Plus, you need to test, learn, and iterate based on the data from each ad run.

6/ We treat it like a partnership (but actually).

Ad copy collaboration, custom AI tools we’ve built for partners, full 7-day and 14-day performance reports with 100% of the data we have available, ongoing input to optimise the campaign. Nearly every sponsor I work with (Atlassian, Vanta, Clay, Attio, Ahrefs, etc) comes back multiple times. 

Probably the thing I’m most proud of.

We have just 2 slots left before prices go up for Q2.

If your product is built for founders, PMs, engineers, or operators in tech - link to our full media kit in the comments 👇

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