Collin Mitchell

Helping People Leave The Rat Race Through Real Estate

You can build four companies. Sell three. Crush quotas. Lead teams.

And still wake up wondering why it doesn't feel like freedom.

I spent over a decade in B2B tech. Built systems. Scaled go-to-market engines. Lived for the rush of leadership and growth.

But behind the wins was a truth I couldn't ignore:

I was successful… and miserable.

Endless Zoom calls. Empty goals. Trading my best hours for a life I didn't want.

I didn't need another promotion. I needed ownership of my time.

That's when I found real estate.

What started as a side hustle turned into a full-time passion—one that finally gave me the autonomy I was chasing in tech but never found.

I went all in:

→ Flips → Rentals → Wholesale deals

I stopped chasing margin and started building real wealth.

✅ 75+ properties wholesaled 
✅ 50 flips completed 
✅ 34 rentals acquired 
✅ $1.5M+ in cash generated 
✅ $1.6M in equity built
✅ $13K/month in cash flow created

⸻

Now, I help SaaS executives and founders turn equity and W-2 income into passive cash flow - averaging 30%+ cash-on-cash returns on turnkey rental properties.

After 4 companies and 3 exits, I learned: equity is exciting, but cash flow is freedom.

No tenant headaches. No property management. No quitting your job.

Just off-market deals that most investors miss, fully managed, cash-flowing from day one.

Our clients are stacking $300–$500/month per property in net cash flow while staying in their SaaS roles.

→ So they can become work-optional 
→ Diversify beyond stock options 
→ And build generational wealth with tangible assets

Most don't want to leave SaaS. They just want freedom when the right moment comes.

That's what I help them build.

Not with hype. Not with overnight promises. With calm, proven execution backed by 4 companies, 3 exits, and hundreds of real estate deals.

We work with a small number of SaaS leaders at a time, so every deal gets the attention it deserves.

DM me "turnkey" if you want to see our latest 30%+ deal breakdown.

Founder/CRO

Monster Technology is a Nationwide Provider of Office Equipment, Imaging Supplies and IT Services


Ryan Staley

I help Chief Revenue Officers & Sales Professionals Leverage AI to work 10 hours less weekly and 2x performance. Follow for cutting-edge cheat codes, prompts, and workflows🎙Scale Up Show Host🔥$0→$30M ARR in 5.5 yrs

Over the last decade, I’ve grown a division from 0-$30M ARR with 4 Sales People and have upskilled over 2,500 GTM executives on AI, Enterprise Sales and GTM Strategy  .

My mission is to inspire 1 million Go To Market Executives to work less and sell more through becoming Superhuman with Artificial Intelligence.

I help revenue leaders transform their teams by acquiring AI skills to escape the operational grind, and accelerate topline revenue.

I’m the founder of Whale Boss and The Scale Up Show.

My portfolio:

→ I’m the Founder of Whale Boss, an AI Sales & Marketing consulting and skill transformation company
→ I’m the Founder of the Scale Up Show, Top 1% Global Podcast
→ I teach Executives, Sales & Marketing teams to implement tools like ChatGPT, Copilot, Claude, etc.   
→ I provide Chief AI Officer Advisory services for human capital.  


My results:

→0-$30M without funding, marketing or SDRs with only 4 Sales people
→Identified and implemented over 500 AI use cases (internally and externally)
→Taught over 800 CROs proprietary selling strategy and tactical execution
→Consulted over 40 Technology companies on custom revenue growth strategies.  
→Voted as a TOP global AI thought leader, Gartner Ambassador & Sales Assembly thought leader. 


If you want to learn more on how to become Superhuman, you can join my newsletter.
⇒ https://superhumanrevenue.beehiiv.com/


If you want to explore AI skill transformation for your organization or Team, apply for an AI Consult.  
=> https://calendly.com/ryanstaleywss/introductory-call-with-ryan-staley-from-whale-boss


Youtube- https://www.youtube.com/channel/UCFGndSHN4KkE89kUP74U7Qg

Podcast-https://ryanstaley.io/podcast/

X-https://x.com/Ryan_Staley1

Podcast Host

I deconstruct how the top SAAS CEOs in the world grow their companies repeatedly and predictably.  

This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak),  Andrew Gazdecki (Founder of Microacquire), Harpaul Sambhi (Founder of Magical with a previous exit to Linkedin) and many more.

We're hiring an AI Transformation Lead.

But here's the thing: I'm not looking for someone who "can" teach AI.

I'm looking for someone who gets genuinely excited when they see the lightbulb moment—when someone realizes AI just gave them their weekends back.

Why this role is different:

Most AI training companies teach and walk away.

We TRAIN → then BUILD.

You'll lead 8-week AI Transformation Sprints for Fortune 1,000 companies, then build custom AI teammates (GPTs, Claude Projects, Copilot agents) that turn training into systematized tools people use every day.

The impact:

Our clients report documented results:

→ Demo prep: 2 hrs → 10 min (92% time saved)
→ Account research: 4 hrs → 30 min (87.5% saved)
→ Prospect lists: Days → Minutes (95%+ saved)
→ Competitive intel: Fully automated

"Usually it takes me about two hours to get all the data compiled… 10 seconds done. Copy, paste, move forward." — Sales Ops Leader

That's $14.21M in annual ROI** across a few clients.

You are:

- 5-10 years in Sales Enablement / Customer Education / RevOps
• Expert-level with ChatGPT, Claude, Gemini, Copilot
• Obsessed with AI—you use it daily and can't stop experimenting
• Proven at driving adoption, not just good feedback scores
• Can build custom AI teammates for business use cases
• Executive presence (you'll work with CROs/CMOs)

Why join:

✓ Category-defining work at the center of enterprise AI transformation at an AI native company
✓ Executive access at Fortune 1,000 and AI forward companies
✓ Ground floor at a fast-scaling company (market growing 24-26% CAGR)
✓ Train + build model creates compounding client relationships
✓ Competitive comp + performance bonuses tied to client outcomes

✓ Work directly with the the CEO (me :)) on day to day basis to do work that matters and to create Superhuman outcomes with AI   

Our mission:

Free people from the grind so their genius—and their kids—get their best hours.

Within 10 years, our alumni will add $50B in value and win back a million weekends.

To apply:

Send to [ryan@whalesellingsystem.com](mailto:ryan@whalesellingsystem.com):

1. 2-min video teaching any AI concept
2. Example of training that drove real adoption
3. Why transformation (not just training) matters to you

Know someone perfect for this? Tag them below. 👇

Founder & CEO, Whale Boss | Demystifying AI Agents | Helping revenue leaders 2x team results through AI Led GTM | Trusted by $50M-$20B PE-backed and Publicly Traded Companies | AI ROI for your team in 60 days

I tested Opus 4.6 across 15+ different use cases this weekend.

Here's my honest breakdown of what's actually different.

After 3 years of implementing AI with 3000+ executives, I can spot the difference between marketing hype and real capability shifts. So when Anthropic dropped Opus 4.6 last week, I didn't read the press release. I ran it through the gauntlet.

Long-form strategy docs. Short-form content. Claude Code for building agentic workflows.

Here are the 3 capabilities that matter for knowledge workers:

1. LONG UNSTRUCTURED PROJECT HANDLING
Most models fall apart when the scope gets messy. Opus 4.6 stays coherent across complex, multi-step work and intuitively identifies what you need next before you ask. That's a massive shift for anyone doing real strategic work.


2. CONNECTING UNSTATED DOTS
I gave it partial context on several projects. Instead of asking me to fill gaps, it inferred the connections and surfaced insights I hadn't explicitly identified. This is the difference between a tool that follows orders and one that actually thinks alongside you.


3. PERSISTENT MEMORY
The enhanced memory means the model builds context over time. No more re-explaining your company, your goals, your preferences every single session. This alone changes the ROI equation for daily AI usage.

NOTE: Benchmarks showed modest improvements. But benchmarks measure isolated tasks. 

They don't measure what happens when a model COMPOUNDS its understanding of your work over weeks.

That's where the real value lives.

Are you seeing the same thing with Claude or with other models?

🔥P.S. Try the prompt in the picture.  I was shocked what it came back with and the level of detail.

Hot take: The most underrated AI tool right now isn't a model.

It's a browser extension.

Claude Chrome extension works really well and I expect this to continue to increase in value.

I know that sounds ridiculous.
Browser extensions have been slow, buggy, and frustrating. Most people have written them off.


But here's what happened when I stopped ignoring Claude's Chrome extension:


I built a complete inventory of every AI assistant and agent I've created across ALL platforms in 15 minutes.


This would have taken me 2 hours of manual copying, pasting, and formatting.


And here's why this matters more than you think:


If you've been building AI systems for the past year, you probably have agents scattered across 3 to 5 platforms with no central view of what exists.


That's not an AI strategy. That's digital hoarding.

The extension handled the tedious part. Pulled the data, organized it, formatted it cleanly.


Will these tools get better? Absolutely.


But RIGHT NOW, they already work for the unglamorous work that actually matters. Data transfer. Organization. Structuring information across platforms.


The flashy stuff gets the attention.
The operational stuff gets the results.


What hidden tool has surprised you lately?

I just watched a 2.5 hour interview that changed how I see the next 3 years. And what he said should make every business leader stop and pay attention.

Dario Amodei, CEO of Anthropic, on the Dwarkesh Podcast. 

Here's the part that hit me hardest:

There are TWO exponentials happening right now. Not one. 

The first is the capability curve. Models getting smarter at research speed. 

The second is economic diffusion. How fast businesses actually ADOPT and deploy AI. Both are fast. Neither is instant. And there's a GAP between them. 

That gap is where careers are being made or destroyed RIGHT NOW. Dario put a number on AGI. 1-3 years for most knowledge work. 90% confidence within a decade. 


He said software engineering gets fully automated FIRST because code is verifiable. It works or it doesn't. But every function is next. Sales. Marketing. Operations. Finance. Strategy. 

The question isn't whether AI will transform your organization. That's settled. 

The question is whether YOU close the gap between what's possible and what your teams are actually doing. 

Anthropic went from $0 to $9-10 BILLION in revenue in 3 years. 

10x growth per year. 
That's not hype. 
That's the market screaming that AI delivers real value. 

I've been implementing AI across leadership teams for 3 years now with 3,100+ executives. 

The pattern is clear. 

The leaders who move during the gap between capability and adoption don't just win. 

They make it nearly impossible for competitors to catch up. 

Whether you're a CEO setting direction, a VP running a division, or a Director leading a team of 15, the window is the same. 


NOTE: I pulled the key visuals and takeaways from the full 2.5 hours so you don't have to watch it all. Link in comments. Where do you think your organization sits on the adoption curve right now?

AGI Transition Strategy

What if the "ruthless" ElevenLabs quota model is actually the most HUMANE way to run a sales team?


Hear me out.


Right now, most sales orgs carry 50+ reps. Half of them miss quota. 

They grind through manual research, data entry, and admin work that has nothing to do with selling.


They burn out. They churn. They blame enablement. Leadership blames them.


Everyone loses.


ElevenLabs flipped the script. 

Micro-teams of 5-10. AI handles the grunt work. 
Reps focus on what they were actually hired to do.

The result? 80% quota attainment.


And if you hit your number? 
You get paid MORE because there are fewer people splitting the pie.


This is the part nobody talks about with AI transformation.


It's not about replacing people.
It's about FREEING the right people to do their best work and paying them what they're actually worth.


The old model punishes A-players by surrounding them with B and C-players who drag down performance, culture, and comp pools.


The new model? Only A-players. Only selling. Only winning.


NOTE: After working with 3,100+ executives on AI transformation, the biggest resistance isn't from reps. It's from leaders who built their identity around managing large teams.


Smaller team = less perceived power.


But the CROs who get over that ego hurdle?


They're the ones building the future.


Would you rather manage 50 reps at 40% attainment or 10 reps at 80%?

Controversial take: The CROs and CMOs who work the MOST hours are often the worst performers.

I know. That's uncomfortable.

But after 23 years in GTM and 3 years of working with 3000+ revenue leaders across Public Traded and PE-backed SaaS, I can't unsee the pattern.

The leaders grinding 80-hour weeks aren't outperforming anyone. They're too exhausted to realize their strategy stopped working 6 weeks ago.
I've been there myself.

I used to wear exhaustion like proof I was committed. 70-hour weeks. Always on. Always grinding. I thought that's what it took to build Whale Boss while delivering for clients.

Then I hit a wall where I couldn't see what was obvious. I was making slower decisions. Recycling old ideas. Running on fumes and calling it discipline.

The moment I started treating rest as a STRATEGIC INPUT instead of a reward, everything changed.

My content got sharper. My client sessions got better. I started seeing patterns in AI implementation I'd been too fried to notice.

Think about Tom Brady.

He didn't become the GOAT by outworking everyone in the weight room. He became the GOAT by obsessing over recovery, nutrition, rest, and how he treated his body. While other quarterbacks were breaking down at 35, Brady played 4-5 years LONGER and at a HIGHER level than his peers.

That wasn't luck. That was a strategic decision to optimize for longevity and peak performance instead of brute force.

Revenue leadership is the same game.

The executives I train who ruthlessly protect recovery time?


They see market shifts faster.
They make pricing decisions with conviction instead of desperation.
They retain their best people because burned-out leaders create burned-out teams.


One CRO told me something I'll never forget:
"I made more strategic progress in 10 days off than I did in the 6 months before. Because I finally had the space to THINK instead of just REACT."

Your brain isn't a machine that performs better with more runtime.
It's a system that performs better with RECOVERY CYCLES.

The same way PE firms don't expect compound returns without reinvestment, you can't expect compound performance without rest.

NOTE: The executives who survive and thrive across multiple PE cycles aren't superhuman. They're the Tom Brady's of leadership. They figured out that strategic rest isn't soft. It's the hardest competitive edge to copy.

What's your actual recovery strategy right now? Or are you still telling yourself you'll rest after this quarter?

AI isn't plateauing.

It's doing the opposite.

Here's the data that should change how every CRO and CMO plans for 2026:

Humanity's Last Exam is a benchmark built by 2,000+ world experts to test what AI CAN'T do.

December 2024: 6%
February 2025: 27%
GPT-5: 42%

7x improvement. 8 months.

Here's what that means for your team:

1. The AI workflows you tested and dismissed 6 months ago? They work now. The quality gap has closed DRAMATICALLY.
2. Your competitors aren't waiting. The ones embedding AI into their revenue motions today are building compound advantages that get harder to close every quarter.
3. The ROI math has fundamentally shifted. What cost you 3 hours now takes 10 minutes. That's not incremental improvement. That's a category shift.

I've seen this firsthand across 2,400+ executives.

The ones who started 12 months ago aren't just ahead.

They're UNREACHABLE.

How are you adjusting your AI strategy for this pace of change?

A special Thanks to @Cliff Simon for hosting me at the Polaris Roadshow.

Founder & CEO, Whale Boss | Demystifying AI Agents | Helping revenue leaders 2x team results through AI Led GTM | Trusted by PE-backed SaaS | Transform your team in 60 days

Canary in the coal mine, here’s why this happened…


This is going to be common moving forward if you don’t take this seriously.

I repeat, if you don’t adapt and AI upskill, companies you work for will adapt for you.

If you don’t adapt your workforce to be AI unskilled you will be disrupted by companies like this that will put you out of business.



This is an exact quote from the CEO.

“we're not making this decision because we're in trouble. our business is strong. gross profit continues to grow, we continue to serve more and more customers, and profitability is improving. but something has changed. we're already seeing that the intelligence tools we’re creating and using, paired with smaller and flatter teams, are enabling a new way of working which fundamentally changes what it means to build and run a company. and that's accelerating rapidly.”

I took inventory of every AI agent and assistant I've built for my business.

Here's a some of what my "Agent/Assistant org chart" looks like:

Operating Systems:
• CEO OS (strategy, planning, reviews)
• Sales OS (pipeline, deal coaching, forecasting)
• Product OS (curriculum, delivery, design)

C-Suite Agents:
• Chief Counsel (legal review, contracts)
• CHRO (hiring, candidate scoring, team design)
• CMO (Content, Creative, Strategy, team design)

Sales:
• Deal Coach with Next Best Action
• Research assistant

Productivity:
• Email management
• Proposal design

Marketing:
• LinkedIn content teammate

Product:
• Program design
• Agent designer
• Customer artifact designer

That's 15 agents across 6 functions. Built in 3 months. No engineering team. No dev budget.

Here's what I've learned:

The mistake most people make with AI agents is building them one at a time, like isolated tools.

The unlock is designing them like an organization.

Just like a company has:
→ Leadership (Operating Systems)
→ Departments (Sales, Marketing, Product)
→ Communication layers (how agents share context)
→ Reporting structure (which agent leads which workflow)

When you architect assistants or agents as a system instead of individual tools, every new agent you add makes the whole thing more powerful.

Not additive. Multiplicative.

The question for every leader right now:

What does YOUR agent org chart look like?

If the answer is "we don't have one" — that's your biggest AI blind spot.

No one is talking about the number one leadership skill needed for 2026 and beyond.

The difference in managing agents vs. people. This framework unlocks a 10-100x differential in terms of results when working with agents. 

Here’s how to think differently

Scarcity Management (Human Labor)

- You delegate carefully because every task you assign costs real capacity
- You prioritize ruthlessly — your team can only do 3-5 things well
- You write minimal specs because the human fills in gaps with judgment and context
- You manage by exception because you can't review everything
- You accept "good enough" because rework costs real time from real people
- You batch work into projects because coordination overhead is high



Abundance Management (Agentic AI)

- You can delegate liberally because spinning up another agent costs nearly nothing
- You can pursue parallel paths — run 5 approaches simultaneously and pick the best
- You write comprehensive specs because thoroughness directly improves output quality, and the agent will actually read all 10 pages
- You can review everything because the agent can also generate its own quality checks
- You can decompose into micro-tasks because coordination overhead is low



Once I dove into this and actually gave myself some space in to think about what's possible, I was really shocked with how different the two worlds are and how much of a change there's going to need to happen at a leadership level to be able to work with both continuously. 

Anything I missed or you see as an opportunity?

taplio

The Battle

Collin Mitchell

Ryan Staley

Followers

Posts

Engagements

Likes

Performance ScoreRyan Staley's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Collin Mitchell

Ryan Staley

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Ryan Staley's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreRyan Staley's LinkedIn Performance